COMPOSITION OF BIOCIDE, AND, METHOD OF CONTROLING THE PROLIFERATION OF MICROBES IN A SYSTEM USED IN

专利摘要:
composition of biocide, and, method of controlling the proliferation of microbes in a system used in the production, transportation, storage and separation of crude oil and natural gas. biocide compositions are described. the compositions are used in applications with respect to the production, transportation, storage and separation of crude oil and natural gas. methods of using the compositions are also described, particularly in applications with respect to the production, transportation, storage and separation of crude oil and natural gas.
公开号:BR112016002166B1
申请号:R112016002166-5
申请日:2014-07-31
公开日:2020-08-18
发明作者:Victor Keasler；Jeffrey Caleb Clark；Carrie Keller-Schultz；Brian Michael Bennett
申请人:Ecolab Usa Inc；
IPC主号:

专利说明:

FIELD OF THE INVENTION
[001] The present description, in general, refers to biocides, and more particularly, to biocides including an imidazoline (for example, acrylated imidazoline), a quaternary amine and a phosphonium compound (for example, tetracis- (hydroxymethyl sulfate) ) phosphonium). BACKGROUND OF THE INVENTION
[002] Oil field systems are subject to greater risks associated with microbial control, including: ELS production, microbial-influenced corrosion (MIC) and biofilm formation. When MIC is suspected in a system, the main area of concern becomes biofilm, or sessile organisms, on the pipe surface. It is widely perceived in the industry that in order to be effective in controlling bacteria in a system, there must be a focus on minimizing the biofilm redevelopment kinetics after treatment (sessile control), in addition to providing sufficient planktonic death. While tetracis- (hydroxymethyl) phosphonium sulfate, glutaraldehyde and quaternary ammonium compounds are widely used as biocides, their effectiveness is limited when considering their ability to delay biofilm redevelopment kinetics after biocide treatment. Thus, there is a greater need, in the oil field industry, to provide microbial death and biofilm control, and, in particular, to penetrate and delay biofilm redevelopment kinetics. SUMMARY OF THE INVENTION
[003] In one aspect, a biocide composition is described including: an imidazoline compound; a quaternary amine; and a phosphonium compound.
[004] The imidazoline compound has the formula (I),
wherein each of R1, R4, and R5 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle, each of said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle independently, at each occurrence, is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, -COR6, -CO2R7, -SO3R8, -PO3H2, -CON (R9) (R10), -OR11e -N (R12 ) (R13); R2 is a radical derived from a fatty acid; R3 is selected from a radical derived from an unsaturated acid; each of R6, R7, R8, R9, R10 and R11 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl; each of R12 and R13 is independently, in each occurrence, selected from hydrogen, alkyl, -COR14, -CO2R15, -alkyl-COR16 and -alkyl-CO2R17; and each of R14, R15, R16 and R17 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl.
[005] For compounds of the formula (I), R1 can be unsubstituted C2-C6 alkyl; R2 is -CI7H35, -C17H33, or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen, CI-CÓ alkyl, or Re is absent; R4 is hydrogen; and R it's hydrogen.
[006] For the compounds of the formula (I), R1 can be linear C-2 alkyl, substituted with a substituent which is a -N (R12) terminal (R13), where R12 is hydrogen and R13 is -COR14, in that R14 is -C17H35, -C17H33, or -C17H31; R2 is -C17H35, -C17H33, or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen, CI-CÓ alkyl, or Re is absent; R4 is hydrogen; and R5 is hydrogen.
[007] For the compounds of the formula (I), R1 can be linear C-2 alkyl, substituted with a substituent which is a -N (R12) (R13) terminal, where each of R12 and R13 is -alkyl- C2-CO2R17, where R17 is hydrogen or is absent; R2 is -C17H35, -C17H33, or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen, CI-CÓ alkyl, or Re is absent; R4 is hydrogen; and R5 is hydrogen.
[008] Additionally, the imidazoline compound can have the formula (II),
wherein each of R1, R4 and R5 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle, each of said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle independently, at each occurrence, is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, -COR6, -CO2R7, -SO3R8, -PO3H2, -CON (R9) (R10), -OR11e -N (R12) (R13); R2 is a radical derived from a fatty acid; each of R3 and Rx is independently selected from a radical derived from an unsaturated acid; each of R6, R7, R8, R9, R10 and R11 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl; each of R12 and R13 is independently, in each occurrence, selected from hydrogen, alkyl, -COR14, -CO2R15, -alkyl-COR16 and -alkyl-CO2R17; and each of R14, R15, R16 and R17 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl.
[009] For a compound of formula (2), R1 can be unsubstituted C2-C6 alkyl; R2 is -C17H35, -C17H33, or -C17H31; R3 is -CfbCfbCCbR6, where Re is hydrogen, CI-CÓ alkyl, or Re is absent; Rx is -CfbCfbCChR6, where Re is hydrogen, CI-CÓ alkyl, or Re is absent; R4 is hydrogen; and R5 is hydrogen.
[0010] For a compound of the formula (2), R1 can be linear C-2 alkyl, substituted with a substituent that is a -N (R12) terminal (R13), where R12 is hydrogen and R13 is -COR14, in that R14 is -C17H35, -C17H33, or -C17H31; R2 is -C17H35, -C17H33, or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen, CI-CÓ alkyl, OR Re is absent; Rx is -CPLCI / hCChR6, where Re is hydrogen, C1-6 alkyl, or Re is absent; R4 is hydrogen; and R5 is hydrogen.
[0011] For a compound of the formula (2), R1 can be linear C-2 alkyl, substituted with a substituent that is a -N (R12) (R13) terminal, where each of R12 and R13 is -alkyl- C2-CO2R17, where R17 is hydrogen or is absent; R2 is -C17H35, -C17H33, or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen, CI-CÓ alkyl, OR Re is absent; Rx is -CHiCbhCChR6, where Re is hydrogen, C1-6 alkyl, or Re is absent; R4 is hydrogen; and R5 is hydrogen.
[0012] Additionally, the imidazoline compound can have a structure of formula (III),
wherein each of R1, R4 and R5 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle, each of said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle independently, at each occurrence, is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, -COR6, -CO2R7, -SO3R8, -PO3H2, -CON (R9) (R10), -OR11e -N (R12) (R13); R2 is a radical derived from a fatty acid; each of R6, R7, R8, R9, R10 and R11 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl; each of R12 and R13 is independently, in each occurrence, selected from hydrogen, alkyl, -COR14, -CO2R15, -alkyl-COR16 and -alkyl-CO2R17; and each of R14, R15, R16 and R17 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl.
[0013] For the compounds of the formula (3), R1 can be unsubstituted C2-CÓ alkyl; R2 is -C17H35, -C17H33, or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[0014] For a compound of the formula (3), R1 can be linear C-2 alkyl, substituted with a substituent that is a -N (R12) (R13) terminal, where R12 is hydrogen and R13 is -COR14, in that R14 is -C17H35, -C17H33, or -C17H31; R2 is -C17H35, -C17H33, or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[0015] For a compound of the formula (3), R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, where each of R12 and R13 is -C2-alkyl -CO2R17, where R17 is hydrogen or is absent; R2 is -C17H35, -C17H33, or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[0016] The quaternary amine can have the formula [N + R5aR6aR7aR8a] [X “] where each of R5a, R6a, R7a and R8a is independently selected from substituted or unsubstituted C1-6 alkyl; and X is Cl, Br or I.
[0017] For the quaternary amine, each of R5a, R6a, R7a and R8a can, independently, be selected from the group consisting of unsubstituted C 1 -Cis alkyl, C 1 -Cis hydroxyalkyl and benzyl.
[0018] The quaternary amine can be selected from the group consisting of tetramethyl ammonium chloride, tetraethyl ammonium chloride, tetrapropyl ammonium chloride, tetrabutyl ammonium chloride, tetrahexyl ammonium chloride, tetraoctyl ammonium chloride, benzyltrimethyl ammonium chloride , benzylatriethyl ammonium chloride, phenyltrimethyl ammonium chloride, phenyltriethyl ammonium chloride, cetyl benzyladimethyl ammonium chloride, hexadecyl trimethyl ammonium chloride, C12-16 benzyl ammonium dimethyl chloride, C12-16 benzyl ammonium monomethyl chloride quaternary, benzyl chloride triethanolamine ammonium quaternary, benzyl chloride dimethylaminoethanolamine quaternary ammonium, cocoalkyl dimethyl benzyl ammonium chloride and combinations thereof.
[0019] The phosphonium compound can be selected from the group consisting of alkyltris (hydroxiorgan) phosphonium salts, alkenyltris (hydroxyiorgan) phosphonium salts, tetracis (hydroxyiorgan) phosphonium salts and combinations thereof.
[0020] Additionally, the phosphonium compound can be selected from the group consisting of C1-C3-tris (hydroxymethyl) phosphonium salts, C2-C3-tris (hydroxymethyl) alkenyl salts, tetracis (hydroxymethyl) salts ) phosphonium and combinations thereof.
[0021] Additionally, the phosphonium compound can be selected from the group consisting of tetracis (hydroxymethyl) phosphonium (THPS), tetracis (hydroxymethyl) phosphonium chloride, tetracis (hydroxymethyl) phosphonium, tetracis (hydroxymethyl) format phosphonium, acetate, (hydroxymethyl) phosphonium, tetracis oxalate (hydroxymethyl) phosphonium and combinations thereof.
[0022] The composition may additionally include a demulsifier. The demulsifier can be selected from the group consisting of dodecylbenzylsulfonic acid (DDBSA), the sodium salt of xylenesulfonic acid (NAXSA), epoxylated and propoxylated compounds, surfactants and anionic, cationic and non-ionic resins, phenolic resins and epoxides and combinations thereof. .
[0023] The composition may additionally comprise one or more additional components, each component independently selected from the group consisting of corrosion inhibitors, solvents, asphaltene inhibitors, paraffin inhibitors, incrustation inhibitors, emulsifiers, water clarifiers, dispersants, inhibitors of gas hydrate, biocides, pH modifiers and surfactants.
[0024] In another aspect, a method for controlling biofilm formation is described, the method comprising providing an effective amount of a composition of the invention in a system. The method may include controlling the proliferation of microbes in a system used in the production, transportation, storage and separation of crude oil and natural gas. The method may include controlling the proliferation of microbes in a system used in a coal-fired power generation process, a wastewater process, a farm, a slaughterhouse, a landfill, a municipal wastewater plant, a process coal cokeification or a biofuel process.
[0025] The compounds, compositions, methods and processes are further described herein. BRIEF DESCRIPTION OF THE DRAWINGS
[0026] Figure 1 shows biocidal activity of the compositions including a quaternary amine and an imidazoline.
[0027] Figure 2 shows biocidal activity of the compositions including one or more of an imidazoline, a quaternary amine and a phosphonium salt.
[0028] Figure 3 shows biocidal activity of the compositions including various ratios of components imidazoline, quaternary amine and phosphonium salt.
[0029] Figure 4 shows an emulsion trend study.
[0030] Figures 5A, 5B and 5C show graphs of the corrosion rate as a function of concentration for V08, THPS and glutaraldehyde. DETAILED DESCRIPTION
[0031] Biocide compositions, methods of using said compositions and processes for their preparation are described here. The compositions include a synergistic combination of at least one imidazoline compound, at least one quaternary amine and at least one phosphonium compound. The compositions can additionally include an emulsion breaker to facilitate the oil / water separation in the system to be treated.
[0032] The compositions are particularly used to control the proliferation of microbes in equipment used in the production, transportation, storage and separation of crude oil and natural gas. The compositions kill planktonic and sessile microorganisms and provide better control of biofilm kinetic redevelopment (sessile control). The compositions are effective against common microbes in the oil field (for example, sulfate reduction and acid-producing bacteria), including genera, such as Desulfovibrio, Desulfomicrobium, Shewanella, Clostridiume Pseudomonas, among others. The compositions thus reduce the required biocide treatment rate and treatment frequency, compared to biocides currently on the market. 1. Definition of the Terms
[0033] Unless otherwise defined, all technical and scientific terms used herein have the same meaning commonly understood by one skilled in the art. In case of conflict, this document, including definitions, will be monitored. Preferred methods and materials are described below, although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All publications, patent applications, patents and other references mentioned here are incorporated by the reference in full. The materials, methods and examples described here are illustrative only and should not be limiting.
[0034] The terms "comprises (m)", "includes (in)", "having", "has", "can (m)", "contains (ê) m", and variants thereof, as follows used, open transitional phrases, terms or words should be considered, which do not exclude the possibility of additional actions or structures. The singular forms "one", "one", "e", "o" and "a" include references in the plural, unless the context clearly indicates otherwise. The present description also contemplates other modalities, "comprising", "consisting of" and "consisting essentially of", of the modalities or elements presented here, whether explicitly presented or not.
[0035] The term "suitable substituent", from the form used here, should mean a chemically acceptable functional group, preferably a fraction that does not cancel the activity of the inventive compounds. Such suitable substituents include, but are not limited to, halo groups, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxy groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, groups aryloxy or heteroaryloxy, aralkyl or heteroaralkyl groups, aralkoxy or heteroaralkoxy groups, HO— (C = O) - groups, heterocyclic groups, cycloalkyl groups, amino groups, alkyl- and dialkylamino groups, carbamoyl groups, alkylcarbonyl groups, alkyloxycarbonyl groups, alkyloxycarbonyl groups , dialkylamino carbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups and arylsulfonyl groups. Those skilled in the art will realize that many substituents can be replaced by additional substituents.
[0036] The term "alkyl", as used herein, refers to a straight or branched hydrocarbon radical, preferably having 1 to 32 carbon atoms (ie, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 or 32 carbons ). Alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl and tertiary butyl. Alkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0037] The term "alkenyl", as used herein, refers to a straight or branched hydrocarbon radical, preferably having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 or 32 carbons and having one or more carbon-carbon double bonds. Alkenyl groups include, but are not limited to, ethylene, 1-propenyl, 2-propenyl (allyl), isopropenyl, 2-methyl-1-propenyl, 1-butenyl and 2-butenyl. Alkenyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0038] The term "alkenyl", as used herein, refers to a straight or branched hydrocarbon radical, preferably having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 or 32 carbons and having one or more carbon-carbon triple bonds. Alquinyl groups include, but are not limited to, ethynyl, propynyl and butynyl. Alkynyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0039] The term "alkoxy", as used herein, refers to an alkyl group, as defined herein, attached to the parent molecular fraction through an oxygen atom.
[0040] The tenuous "aryl", as used here, means monocyclic, bicyclic or aromatic tricyclic radicals, such as phenyl, naphthyl, tetrahydronaftyl, indanyl and the like; optionally substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
[0041] The term "arylalkyl", as used here, refers to an aryl group attached to the parent molecular fraction through an alkyl group. Arylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0042] The term "alkylarylalkyl", as used herein, refers to an alkylaryl group attached to the parent molecular fraction through an alkyl group. Alkylarylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0043] The term "carbonyl", "(C = O)", or "-C (O) -" (as used in phrases, such as alkylcarbonyl, alkyl - (C = O) - or alkoxycarbonyl) refers to at the junction of the fraction> C = O to a second fraction, such as an alkyl or amino group (i.e. a starch group). Alkoxycarbonylamino (i.e., alkoxy (C = O) —NH—) refers to an alkyl carbamate group. The carbonyl group is also equivalently defined here as (C = O). Alkylcarbonylamino refers to groups, such as acetamide.
[0044] The term "cycloalkyl", as used herein, refers to a monocyclic, bicyclic or tricyclic carbocyclic radical (for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclopentenyl , cyclohexenyl, bicycles [2.2.1] heptanyl, bicycles [3.2.1] octanyl and bicycles [5.2.0] nonanyl, etc.); optionally containing 1 or 2 double bonds. Cycloalkyl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
[0045] The term "cycloalkylalkyl", as used here, refers to a cycloalkyl group attached to the parent molecular fraction through an alkyl group. Cycloalkylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0046] The term "alkylcycloalkylalkyl", as used herein, refers to a cycloalkylalkyl group substituted by one or more alkyl groups. Alkylcycloalkylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0047] The term "halo" or "halogen", as used here, refers to a fluorine, chlorine, bromine or iodine radical.
[0048] The term "heteroaryl", as used herein, refers to a monocyclic, bicyclic or tricyclic aromatic heterocyclic group containing one or more heteroatoms (for example, 1 to 3 heteroatoms) selected from O, S and N in the ring ( s). Heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, furyl, imidazolyl, pyrrolyl, oxazolyl (eg 1,3-oxazolyl, 1,2-oxazolyl), thiazolyl (eg 1 , 2-thiazolyl, 1,3-thiazolyl), pyrazolyl, tetrazolyl, triazolyl (eg 1,2,3-triazolyl, 1,2,4-triazolyl), oxadiazolyl (eg 1,2,3-oxadiazolyl ), thiadiazolyl (e.g. 1,3,4-thiadiazolyl), quinolyl, isoquinolyl, benzothienyl, benzofuryl and indolyl. Heteroaryl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
[0049] The term "heteroarylalkyl", as used here, refers to a heteroaryl group attached to the parent molecular fraction through an alkyl group. Heteroarylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0050] The term "alkyl-heteroarylalkyl", as used herein, refers to a heteroarylalkyl group substituted by one or more alkyl groups. Alkyl-heteroarylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0051] The term "heterocycle" or "heterocyclyl", as used herein, refers to a monocyclic, bicyclic or tricyclic group containing 1 to 4 heteroatoms selected from N, O, S (O) n, P (O) n , PRZ, NH or NRZ, where Rz is a suitable substituent. Heterocyclic groups optionally contain 1 or 2 double bonds. Heterocyclic groups include, but are not limited to, azetidinyl, tetrahydrofuranyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydrothiazinyl, tetrahydro, tetrahydrinin, oxyinin, tetrahydrinin, oxyzin, tetraazinyl, oxyzin, tetrahydrin, oxyzin, tetrahydrin, oxyzin, tetrahydrin, tetrahydrin, oxyzine quinuclidinyl, chromanyl, isochromanyl and benzoxazinyl. Examples of saturated or partially saturated monocyclic ring systems are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidin-l-yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-l-yl, pyrrolidin-2 -yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, 1,3-oxazolidin -3-yl, isothiazolidine, 1,3-thiazolidin-3-yl, 1,2-pyrazolidin-2-yl, 1,3-pyrazolidin-1-yl, thiomorpholin-yl, 1,2-tetrahydrothiazin-2-yl , 1,3-tetrahydrothiazin-3-yl, tetrahydrothiadiazin-yl, morpholin-yl, 1,2-tetrahydrodiazin-2-yl, 1,3-tetrahydrodiazin-1-yl, 1,4-oxazin-2-yl and 1 , 2,5-oxatiazin-4-yl. Heterocyclic groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 3 suitable substituents, as defined above.
[0052] The term "heterocyclylalkyl", as used herein, refers to a heterocycle group attached to the parent molecular fraction through an alkyl group. Heterocyclylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0053] The term "alkyl-heterocyclylalkyl" as used herein refers to a heterocyclylalkyl group substituted by one or more alkyl groups. Alkyl-heterocyclylalkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
[0054] The term "hydroxy", as used herein, refers to a group - OH.
[0055] The term "oxo", as used here, refers to an oxygen radical with double bond (= O) in which the bonded pair is a carbon atom. A radical like this can also be considered as a carbonyl group.
[0056] The term "acrylate", as used here, refers to the material that results from Michael's addition of acrylic acid to an imidazoline. The addition of this chemical fraction to imidazoline increases its solubility in water, allowing it to reach metal surfaces, which are submerged below an aqueous layer.
[0057] The term “TOFA”, as used herein, refers to a tall oil fatty acid which is a derivative of the distilled product from trees and includes a mixture of fatty acids, C17H31-35 COOH with a CAS No. 61790-12-3. It is a mixture of oleic acid as a main component, linoleic acid and saturated fatty acids (for example, about 46% oleic acid, about 41% linoleic acid, about 4% stearic acid and about 9% other acids).
[0058] The term "decila", as used here, means an alkyl radical -C10H21, also referred to as "caprila".
[0059] The term "dodecyl", as used here, means an alkyl radical -C12H25, also referred to as "lauryl".
[0060] The term "hexadecyl", as used herein, means an alkyl-CióHss radical, also referred to as "palmitilla"
[0061] The term "hexyl", as used herein, means an alkyl-CóH i s radical, also referred to as "caproila".
[0062] The term "octadecadienila", as used here, means a cis radical, cis-9,12-octadecadienila, also referred to as "linoleyl".
[0063] The term "octadecenyl", as used herein, means a cis-9-octadecenyl radical, also referred to as "oleyl".
[0064] The term "octadecyl", as used herein, means an alkyl radical -C18H37, also referred to as "stearyl"
[0065] The term "octyl", as used herein, means an alkyl-CgHn radical, also referred to as "caprylil".
[0066] The term "tetradecyl", as used here, means an alkyl radical -C14H29, also referred to as "myristyl".
[0067] The term "myristoleic acid" or "(Z) - tetradec-9-enoic acid", as used herein, refers to

[0068] The term "palmitoleic acid" or "(Z) - hexadec-9-enoic acid", as used herein, refers to

[0069] The term "sapienic acid" or "(Z) - hexadec-6-enoic acid", as used herein, refers to

[0070] The term "oleic acid" or "(Z) - octadec-9-enoic acid", as used herein, refers to

[0071] The term “elaidic acid” or “(E) - octadec-9-enoic acid”, as used herein, refers to

[0072] The term “vaccenic acid” or “(E) - octadec-11-enoic acid”, as used herein, refers to

[0073] The term “linoleic acid” or “(9Z, 12Z) - octadeca-9,12-dienoic acid”, as used herein, refers to

[0074] The term "linoelaidic acid" or "(9E, 12E) - octadeca-9,12-dienoic acid", as used herein, refers to

[0075] The term “a-linolenic acid” or “(9Z, 12Z, 15Z) - octadeca-9,12,15-trienico acid”, as used herein, refers to

[0076] The term "arachidonic acid" or "(5Z, 8Z, 11Z, 14Z) - icosa-5,8, ll, 14-tetraenoic acid", as used herein, refers to

[0077] The term "eicosapentaenoic acid" or "(5Z, 8Z, 11Z, 14Z, 17Z) - icosa-5,8, ll, 14,17-pentaenoic acid", as used herein, refers to

[0078] The term “erucic acid” or “(Z) - docos-13-enoic acid”, as used herein, refers to

[0079] The term docosahexaenoic acid or “(4Z, 7Z, 10Z, 13Z, 16Z, 19Z) - docosa-4,7,10,13,16,19-hexaenoic acid”, as used herein, refers to

[0080] The term “hexadecatrienoic acid” or “(7Z, 10Z, 13Z) - hexadeca-7,10,13-trienoic”, as used herein, refers to

[0081] The term "stearidonic acid" or "(6Z, 9Z, 12Z, 15Z) - octadeca-6,9,12,15-tetraenoic", as used herein, refers to

[0082] The term "eicosatrienoic acid" or "(11Z, 14Z, 17Z) - icosa-11,14,17-trienoic acid", as used herein, refers to

[0083] The term "eicosatetraenoic acid" or "(5Z, 8Z, 11Z, 14Z, 17Z) - icosa-5,8, ll, 14,17-pentaenoic acid", as used herein, refers to

[0084] The term "henicosapentaenoic acid" or "(6Z, 9Z, 12Z, 15Z, 18Z) - henicosa-6,9,12,15,18-pentaenoic acid", as used herein, refers to

[0085] The term "clupadonic acid" or "(7Z, 10Z, 13Z, 16Z, 19Z) - docosa-7,10,13,16,19-pentaenoic acid", as used herein, refers to

[0086] The term "osbond acid" or "(4Z, 7Z, 10Z, 13Z, 16Z) - docosa-4,7,10,13,16-pentaenoic acid", as used herein, refers to

[0087] The term “(9Z, 12Z, 15Z, 18Z, 21Z) - tetracosa- 9,12,15,18,21-pentaenoic acid”, as used herein, refers to

[0088] The term "nisinic acid" or "(6Z, 9Z, 12Z, 15Z, 18Z, 21Z) - tetracosa-6,9,12,15,18,21-hexaenoic acid", as used herein, refers to The

[0089] The term “y-linolenic acid” or “(6Z, 9Z, 12Z) - octadeca-6,9,12-trenoic acid”, as used herein, refers to

[0090] The term "eicosadienic acid" or "(11Z, 14Z) - icosa- 11,14-dienoic acid", as used herein, refers to

[0091] The term "di-homo-y-linolenic acid" or "(8Z, 11Z, 14Z) - icosa-8,11,14-trenoic acid", as used herein, refers to

[0092] The term “docosadienic acid” or “(13Z, 16Z) - docosa-13,16-dienoic acid”, as used herein, refers to

[0093] The term “adrenic acid” or “(7Z, 10Z, 13Z, 16Z) -docosa- 7,10,13,16-tetraenoic acid”, as used herein, refers to

[0094] The term "tetracosatetraenoic acid" or "(9Z, 12Z, 15Z, 18Z) - tetracosa-9,12,15,18-tetraenoic acid", as used herein, refers to

[0095] The term "(6Z, 9Z, 12Z, 15Z, 18Z) - tetracosa-6,9,12,15,18-pentaenoic acid", as used herein, refers to

[0096] The term "(Z) - Eicos-11-enoic acid" or "(Z) -icos-ll-enoic acid", as used herein, refers to

[0097] The term "paulinic acid" or "(Z) - icos-13-enoic acid", as used herein, refers to

[0098] The term "mead acid" or "(5Z, 8Z, 11Z) - Eicosa-5,8,11- trienic acid", as used herein, refers to

[0099] The term "nervous acid", or "(Z) - tetracos-15-enoic acid", as used here, refers to

[00100] The term “rumenic acid” or “(9Z, 1 IE) - octadeca-9,11- dienoic acid”, as used herein, refers to

[00101] The term “a-calendic acid” or “(8E, 10E, 12Z) - octadeca-8,10,12-trienico acid”, as used herein, refers to

[00102] The term "β-caWndico acid" or "(8E, 10E, 12E) - octadeca-8,10,12-trienoic acid", as used herein, refers to

[00103] The term “jacaric acid” or “(8E, 10Z, 12E) - octadeca-8,10,12-trienoic acid”,

[00104] The term “a-eleoesteáricoic acid” or “(9Z, 11E, 13E) - octadeca-9,11,13-trienóico acid”, as used here, refers to

[00105] The term "P-eleoesteárico acid" or "(9E, 11E, 13E) - octadeca-9,11,13-trienóico acid", as used here, refers to

[00106] The term "catpalic acid" or "(9E, 11E, 13Z) - octadeca-9,11,13-trienico acid", as used herein, refers to

[00107] The term "punicic acid" or "(9Z, 11E, 13Z) - octadeca-9,11,13-trienoic acid", as used herein, refers to

[00108] The term “rumelenic acid” or “(9E, 11Z, 15E) - octadeca-9,11,15-trienoic”, as used herein, refers to

[00109] The term "a-parinic acid" or "(9Z, 11E, 13E, 15Z) - octadeca-9,11,13,15-tetraenoic", as used herein, refers to

[00110] The term "P-parinic acid" or "(9E, 11E, 13E, 15E) - octadeca-9,11,13,15-tetraenoic", as used herein, refers to

[00111] The term "bosseopentaenoic acid" (5Z, 8Z, 10E, 12E, 14Z) - icosa-5,8,10,12,14-pentaenoic acid, as used herein, refers to

[00112] The term “pinolenic acid” or “(5Z, 9Z, 12Z) - octadeca-5,9,12-trenoic acid”, as used herein, refers to

[00113] The term “podocápric acid” or “(5Z, 11Z, 14Z) - icosa- 5,11,14-trenoic acid”, as used herein, refers to

[00114] Q Vgtoq "áekfq rtqrk» pkeq ", as used here, refers to CH3CH2COOH.
[00115] Q Vgtoq "áekfq dwVítkeq", as used here, refers to CH3 (CH2) 2COOH.
[00116] The term “áekfq xcnfitkeq”, as used here, refers to CH3 (CH2) 3COOH.
[00117] Q vgtoq “áekfq ecrt„ keq ”, as used here, refers to CH3 (CH2) 4COOH.
[00118] Q Vgtoq "áekfq gpâpVkeq", as used herein, refers to CH3 (CH2) 5COOH.
[00119] Q Vgtoq "áekfq ecrtínkeq", as used herein, refers to CH3 (CH2) 6COOH.
[00120] Q Vgtoq "áekfq rgncti» pkeq ", as used herein, refers to CH3 (CH2) 7COOH.
[00121] Q Vgtoq "áekfq eártkeq", as used herein, refers to CH3 (CH2) 8COOH.
[00122] Q Vgtoq "áekfq wpfgeínkeq", as used herein, refers to CH3 (CH2) 9COOH.
[00123] Q Vgtoq "áekfq náwtkeq", as used herein, refers to CH3 (CH2) 10COOH.
[00124] Q Vgtoq "áekfq Vtkfgeínkeq", as used herein, refers to CH3 (CH2) 11COOH.
[00125] Q Vgtoq "áekfq oktíuVkeq", as used herein, refers to CH3 (CH2) 12COOH.
[00126] Q Vgtoq "áekfq rgpVcfgeínkeq", as used herein, refers to CH3 (CH2) 13COOH.
[00127] Q Vgtoq "áekfq rcnoíVkeq", as used herein, refers to CH3 (CH2) 14COOH.
[00128] The term "margárico acid", as used here, refers to CH3 (CH2) I5COOH.
[00129] The term "stearic acid", as used herein, refers to CH3 (CH2) I6COOH.
[00130] The term "nonadecyl acid", as used herein, refers to CH3 (CH2) I7COOH.
[00131] The term "arachidic acid", as used herein, refers to CH3 (CH2) I8COOH.
[00132] The term "henicosilic acid", as used herein, refers to CH3 (CH2) i9COOH.
[00133] The term "behenic acid", as used herein, refers to CH3 (CH2) 20COOH.
[00134] The term "tricyclic acid", as used herein, refers to CH3 (CH2) 2ICOOH.
[00135] The term "lignoceric acid", as used herein, refers to CH3 (CH2) 22COOH.
[00136] The term "pentacosylic acid", as used herein, refers to CH3 (CH2) 23COOH.
[00137] The term "kerotic acid", as used herein, refers to CH3 (CH2) 24COOH.
[00138] The term "heptacosylic acid", as used herein, refers to CH3 (CH2) 25COOH.
[00139] The term "montanic acid", as used herein, refers to CH3 (CH2) 26COOH.
[00140] The term "nonacosylic acid", as used herein, refers to CH3 (CH2) 27COOH.
[00141] The term "melissic acid", as used herein, refers to CH3 (CH2) 28COOH.
[00142] The term "henatriacontylic acid", as used herein, refers to CH3 (CH2) 29COOH.
[00143] The term "laceróico acid", as used here, refers to CH3 (CH2) 30COOH.
[00144] The term "psyllic acid", as used herein, refers to CH3 (CH2) 3ICOOH.
[00145] The term "geddic acid", as used herein, refers to CH3 (CH2) 32COOH.
[00146] The term "ceroplastic acid", as used herein, refers to CH3 (CH2) 33COOH.
[00147] The term "hexatriacontylic acid", as used herein, refers to CH3 (CH2) 34COOH. 2. Compositions
[00148] The compositions described herein include an imidazoline compound, a quaternary amine and a phosphonium compound. The compositions can additionally include a demulsifier. The compositions can additionally include a synergetic. The compositions can additionally include a solvent. The compositions can additionally include one or more additional components.
[00149] The composition can include an imidazoline compound, a quaternary amine, a phosphonium compound and a demulsifier.
[00150] Additionally, the composition can include an imidazoline compound, a quaternary amine, a phosphonium compound, a demulsifier and a synergetic.
[00151] Additionally, the composition can include an imidazoline compound, a quaternary amine, a phosphonium compound, a demulsifier and a solvent.
[00152] Still further, the composition can include an imidazoline compound, a quaternary amine, a phosphonium compound and a solvent.
[00153] Additionally, the composition can include an imidazoline compound, a quaternary amine, a phosphonium compound, a synergetic and a solvent.
[00154] Additionally, the composition can include an imidazoline compound, a quaternary amine, a phosphonium compound, a demulsifier, a synergetic and a solvent. The. Compound of imidazolines
[00155] The compositions described herein include at least one imidazoline compound. The imidazoline compound can have the formula (I), (II) or (III),


wherein each of R1, R4 and R3 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle, each of said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl and heterocycle independently, at each occurrence, is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, -COR6, -CO2R7, -SO3R8, -PO3H2, -CON (R9) (R10), -OR11e -N (R12) (R13); R2 is a radical derived from a fatty acid; each of R3 and Rx is independently selected from a radical derived from an unsaturated acid; each of R6, R7, R8, R9, R10 and R11 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl; each of R12 and R13 is independently, in each occurrence, selected from hydrogen, alkyl, -COR14, -CO2R15, -alkyl-COR16 and -alkyl-CO2R17; and each of R14, R15, R16 and R17 is independently, in each occurrence, selected from hydrogen, alkyl and alkenyl.
[00156] For these imidazolines, R groups of carboxylic acid fractions may be absent where R = H and the carboxylic acid fraction are deprotonated. For example, R15 and / or R17 may be absent where R12 and / or R13 is a fraction of deprotonated carboxylic acid (for example, where R12 is -CH2CH2CO2).
[00157] For an imidazoline compound, R1 can be unsubstituted alkyl. For example, R1 may be unsubstituted C 1 -C 6 alkyl (eg, methyl, ethyl, propyl (eg, w-propyl, isopropyl), butyl (eg, w-butyl, isobutyl, ich-butyl, sec-butyl ), pentyl (e.g., n-pentyl, isopentyl, tert-pentyl, neopentyl, vec-pentyl, 3-pentyl), hexyl, heptyl, octyl, nonyl or decyl). In addition, R1 may be unsubstituted C2-Cw alkyl. For these imidazoline compounds, R1 may be unsubstituted C2-Cs alkyl. In addition, R1 may be unsubstituted C2-CÓ alkyl. Preferably, R1 is propyl, butyl or hexyl.
[00158] For these imidazolines, R1 is substituted alkyl. For example, R1 is substituted C1-Cw alkyl, substituted C2-Cw alkyl, substituted C2-Cg alkyl or substituted C2-C6 alkyl. Additionally, R1 is C1 -C10 alkyl, C2-Cw alkyl, C2-Cg alkyl or C2-CÓ alkyl, substituted with a substituent selected from -COR6, -CO2R7, -SO3R8, -PO3H2, -CON (R9) (R10) , -OR11e -N (R12) (R13), where R6, R7, R8, R9, R10, R11, R12 and R13 are as previously defined. More specifically, R1 is C2-CÓ alkyl, substituted with a substituent selected from -N (R12) (R13), where each of R12 and R13 is independently selected from hydrogen, alkyl, -COR14, - CO2R15, -alkyl- COR16 and -alkyl-CO2R17, where R14, R15, R16 and R17 are as previously defined. Additionally, R1 is C2-CÓ alkyl, substituted with a substituent selected from -N (R12) (R13), where each of R12 and R13 is independently selected from hydrogen, C2-C6 alkyl, -COR14, -CO2R15, - C2-C6-COR16 alkyl and -C2-C6-CO2R17 alkyl, where R14, R15, R16 and R17 are selected from hydrogen and C1-C34 alkyl. For these imidazolines, R1 is linear C2-CÓ alkyl, substituted with a substituent which is a -N (R12) (R13) terminal, where each of R12 and R13 is independently selected from hydrogen, -COR14, -CO2R15, -alkyl C2-C6-COR16 and -C2-C6-CO2R17 alkyl, where R14, R13, R16 and R17 are selected from hydrogen and C1-C34 alkyl. For example, R1 is linear C-2 alkyl, substituted with a substituent that is a -N (R12) (R13) terminal, where R12 is hydrogen and R13 is -COR14, where R14 is -C17H35, -C17H33 or - C17H31. In addition, R1 is linear C-2 alkyl, substituted with a substituent which is a -N (R12) (R13) terminal, where each of R12 and R13 is a -C2-alkyl-CO2R17, where R17 is hydrogen.
[00159] For the imidazolines of formulas (I), (II) and (III), R2 is C4-C34 alkyl or C4-C34 alkenyl. For example, R2 is - (CH2) 3CH3; - (CH2) 4CH3; - (CH2) 5CH3; - (CH2) 6CH3; - (CH2) 7CH3; - (CH2) 8CH3; - (CH2) 9CH3; - (CH2) ioCH3; - (CH2) hCH3; - (CH2) i2CH3; - (CH2) i3CH3; - (CH2) i4CH3; - (CH2) 15CH3; - (CH2) i6CH3; - (CH2) i7CH3; - (CH2) i8CH3; - (CH2), 9CH3; - (CH2) 2oCH3; - (CH2) 2iCH3; - (CH2) 22CH3; - (CH2) 23CH3; - (CH2) 24CH3; - (CH2) 25CH3; - (CH2) 26CH3; - (CH2) 27CH3; - (CH2) 28CH3; - (CH2) 29CH3; - (CH2) 3CH3; - (CH2) 3iCH3; - (CH2) 32CH3; - (CH2) 33CH3; - (CH2) 34CH3; - (CH2) 2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = C HCH2CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CH (CH2) 7CH3; - (CH2) 3CH = CHCH2CH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CH (CH2) 4CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 3CH = CHCH = CHCH = CHCH = CHCH = CH (CH2) 4CH3; - (CH2) 4CH = CH (CH2) 8CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = C HCH2CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 6CH = CHCH = CHCH = CH (CH2) 4CH3; - (CH2) 6CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CH (CH2) 3CH3; - (CH2) 7CH = CH (CH2) 5CH3; - (CH2) 7CH = CH (CH2) 7CH3; - (CH2) 7CH = CHCH = CHCH = CH (CH2) 3CH3; - (CH2) 7CH = CHCH = CH (CH2) 5CH3; - (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH = CHCH2CH2CH = CHCH2CH3; - (CH2) 7CH = CHCH = CHCH = CHCH = CHCH2CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 9CH = CH (CH2) 5CH3; - (CH2) 9CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 9CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 9CH = CH (CH2) 7CH3; - (CH2) hCH = CH (CH2) 5CH3; - (CH2) iiCH = CH (CH2) 7CH3;
[00160] For imidazolines, R2 can be a radical derived from a saturated or unsaturated fatty acid. Saturated fatty acids include, but are not limited to, butyric acid, valeric acid, caprylic acid, enanic acid, caprylic acid, pelargonic acid, capric acid, undecyl acid, lauric acid, tridecyl acid, myristic acid, pentadecyl acid, palmitic acid, margárico acid, stearic acid, nonadecylic acid, arachidic acid, henicosilic acid, behenic acid, tricosilic acid, lignoceric acid, pentacosylic acid, cerotic acid, heptacosylic acid, montanic acid, nonacosylic acid, melisic acid, henatriacontylic acid, laceric acid, psycho , geddic acid, ceroplastic acid and hexatriacontylic acid. Suitable unsaturated fatty acids include, but are not limited to, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vacenic acid, linoleic acid, linoelaidoco acid, a-linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexenic acid, hexadecatrienoic acid, stearidonic acid, eicosatrienoic acid, eicosatetraenoic acid, heneicosapentaenoic acid, clupadonic acid, osbond acid, (9Z, 12Z, 15Z, 18Z, 21Z) -tetracosa- 9,12,15,18,28,21,21 , nisinic acid, y-linolenic acid, eicosadienic acid, di-homo-y-linolenic acid, docosadienic acid, adrenic acid, tetracosatetraenoic acid, (6Z, 9Z, 12Z, 15Z, 18Z) -tetracous acid- 6,9,12 , 15,18-pentaenoic, (Z) -Eicos-ll-enoic acid, mead acid, erucic acid, nerve acid, rumenic acid, a-calendic acid, β-calendic acid, alligator acid, a-eleoesteearic acid, β -eleoestric acid, catelic acid, punicic acid, rumelenic acid, a-parinar acid ico, β-parinic acid, bosseopentaenoic acid, pinolenic acid and podocápric acid. Preferably, R2 is derived from coconut oil, beef fat or tall oil fatty acids (TOFA).
[00161] For imidazoline, R3 is -C (RaRb) -C (RcRd) -CO2Re, where each of Ra, Rb, Rc and Rd is independently selected from the group consisting of hydrogen (-H), halogen and alkyl and where Re is hydrogen (- H) or alkyl. For example, R3 is -C (RaRb) -C (RcRd) -CC> 2Re, where each of Ra, Rb, Rc and Rd is independently selected from the group consisting of hydrogen (-H), halogen and CI alkyl -CÓ and where Re is hydrogen (-H) or CI-CÓ alkyl. Additionally, R3 is -CH2CH2CO2Re, where Re is hydrogen (-H) or CI-COC alkyl. In addition, Re may be absent where R3 is a deprotonated fraction of carboxylic acid (for example, where R3 is - CH2CH2CO2).
[00162] For imidazolines, R3 can be derived from an acrylic acid. Suitable acrylic acids include, but are not limited to, acrylic acid, methacrylic acid, 2-ethylacrylic acid, 2-propyl acrylic acid and 2- (trifluoromethyl) acrylic acid. For example, R3 can be derived from acrylic acid (H2C = CHCO2H).
[00163] Imidazolines of formulas (I), (II) or (III) can have Rx is - C (RaRb) -C (RcRd) -CO2Re, where each of Ra, Rb, Rc and Rd is independently selected from group consisting of hydrogen (-H), halogen and alkyl and where Re is hydrogen (-H) or alkyl. Additionally, Rx can be -C (RaRb) -C (RcRd) -CO2Re, where each of Ra, Rb, Rc and Rd is independently selected from the group consisting of hydrogen (-H), halogen and alkyl CI-CÓ and where Re is hydrogen (-H) or CI-CÓ alkyl. Additionally, Rx is -CH2CH2CO2Re, where Re is hydrogen (-H) or CI-COC alkyl. In addition, Re may be absent where Rx is a fraction of deprotonated carboxylic acid (for example, where Rx is -CH2CH2CO2).
[00164] For the imidazolines described here, Rx can be derived from an acrylic acid. Suitable acrylic acids include, but are not limited to, acrylic acid, methacrylic acid, 2-ethylacrylic acid, 2-propyl acrylic acid and 2- (trifluoromethyl) acrylic acid. For example, Rx can be derived from acrylic acid (H2C = CHCO2H).
[00165] Imidazolines of formulas (I), (II) or (III) can each have R4 and R independently, and is unsubstituted C 1 -C 6 alkyl (e.g., methyl, ethyl, propyl (e.g. w-propyl, isopropyl), butyl (for example, w-butyl, isobutyl, forc-butyl, sec-butyl), pentyl (for example, n-pentyl, isopentyl, forc-pentyl, neopentyl, svc-pentyl, 3- pentyl), hexyl, heptyl, octyl, nonyl or decyl) or hydrogen. In addition, each of R4 and R5 may, independently, be an unsubstituted C1-6 alkyl group or hydrogen. Preferably, each of R4 and R5 is hydrogen (-H).
[00166] Imidazolines of formulas (I), (II) or (III) can have R6, R7, R8, R9, R10 and R11 each independently being, in each occurrence, selected from hydrogen, unsubstituted alkyl and unsubstituted alkenyl . For example, each of R6, R7, R8, R9, R10 and R11 can be independently selected for each occurrence from hydrogen, unsubstituted C1-C34 alkyl and unsubstituted C2-C34 alkenyl. Additionally, R6, R7, R8, R9, R10 and R11 can each be independently selected at each occurrence from hydrogen, unsubstituted C1-C10 alkyl and unsubstituted C2-C10 alkenyl.
[00167] Additionally, each of R6, R7, R8, R9, R10 and R11 can be independently selected in each occurrence from hydrogen and a radical derived from a fatty acid.
[00168] For the imidazoline compounds, each of R12 and R13 can, independently, in each occurrence, be selected from hydrogen, C1-C10 alkyl, -COR14, -CO2R15, -C1-Cio-COR16 alkyl and -C1 alkyl -C10- CO2R17. In addition, each of R12 and R13 can be independently selected for each occurrence from hydrogen, unsubstituted C1-C10 alkyl, -COR14, -CO2R15, -C1-Cw-COR16 alkyl and -C1-C10-CO2R17 alkyl.
[00169] For imidazolines, each of R14, R15, R16 and R17 can be independently selected in each occurrence from hydrogen, unsubstituted alkyl and unsubstituted alkenyl. Additionally, each of R14, R15, R16 and R17 can be independently selected for each occurrence from hydrogen, C1-C34 unsubstituted alkyl and C2-C34 unsubstituted alkenyl. In addition, R14, R15, R16 and R17 can each be independently selected at each occurrence from hydrogen, unsubstituted C1-C10 alkyl and unsubstituted C2-C10 alkenyl. In addition, R15 and / or R17 may be absent where the carboxylic acid fraction is deprotonated.
[00170] Imidazoline compounds can each have R14, R15, R16 and R17, and independently, in each occurrence, be selected from hydrogen and a radical derived from a fatty acid. Additionally, each of R14, R15, R16 and R17 can be independently selected for each occurrence from hydrogen, C4-C34 alkyl and C4-C34 alkenyl. Additionally, each of R14, R15, R16 and R17 can be, independently, in each occurrence, selected from hydrogen; - (CH2) 3CH3; - (CH2) 4CH3; - (CH2) 5CH3; - (CH2) 6CH3; - (CH2) 7CH3; - (CH2) 8CH3; - (CH,), ®; - (CH2) 10 CH3; - (CH2) hCH3; - (CH2) i2CH3; - (CH2) i3CH3; - (CH2) i4CH3; - (CH2) 15CH3; - (CH2) i6CH3; - (CH2) i7CH3; - (CH2) i8CH3; - (CH2) i9CH3; - (CH2) 20CH3; - (CH2) 2iCH3; - (CH2) 22CH3; - (CH2) 23CH3; - (CH2) 24CH3; - (CH2) 25CH3; - (CH2) 26CH3; - (CH2) 27CH3; - (CH2) 28CH3; - (CH2) 29CH3; - (CH2) 30CH3; - (CH2) 31CH3; - (CH2) 32CH3; - (CH2) 33CH3; - (CH2) 34CH3; - (CH2) 2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = C HCH2CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CH (CH2) 7CH3; - (CH2) 3CH = CHCH2CH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CH (CH2) 4CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 3CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 3CH = CHCH = CHCH = CHCH = CHCH = CH (CH2) 4CH3; - (CH2) 4CH = CH (CH2) 8CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 4CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = C HCH2CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 5CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 6CH = CHCH = CHCH = CH (CH2) 4CH3; - (CH2) 6CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CH (CH2) 3CH3; - (CH2) 7CH = CH (CH2) 5CH3; - (CH2) 7CH = CH (CH2) 7CH3; - (CH2) 7CH = CHCH = CHCH = CH (CH2) 3CH3; - (CH2) 7CH = CHCH = CH (CH2) 5CH3; - (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH = CHCH2CH2CH = CHCH2CH3; - (CH2) 7CH = CHCH = CHCH = CHCH = CHCH2CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 7CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 9CH = CH (CH2) 5CH3; - (CH2) 9CH = CHCH2CH = CH (CH2) 4CH3; - (CH2) 9CH = CHCH2CH = CHCH2CH = CHCH2CH3; - (CH2) 9CH = CH (CH2) 7CH3; - (CH2) hCH = CH (CH2) 5CH3; - (CH2) iiCH = CH (CH2) 7CH3; - (CH2) hCH = CHCH2CH = CH (CH2) 4CH3; e - (CH2) i3CH = CH (CH2) 7CH3
[00171] For the imidazolines of formulas (I), (II) and (III), each of R14, R13, R16 and R17 can be independently, in each occurrence, selected from hydrogen, a radical derived from a fatty acid saturated and a radical derived from an unsaturated fatty acid. Suitable saturated fatty acids include, but are not limited to, butyric acid, valeric acid, caprylic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecyl acid, lauric acid, tridecyl acid, myristic acid, pentadecyl acid, palmitic acid , margárico acid, stearic acid, nonadecylic acid, arachidic acid, henicosilic acid, behenic acid, tricosilic acid, lignoceric acid, pentacosylic acid, cerotic acid, heptacosylic acid, montanic acid, nonacosylic acid, melacosic acid, henatriacontylic acid, laceróico acid psyllic, geddic acid, ceroplastic acid and hexatriacontylic acid. Suitable unsaturated fatty acids include, but are not limited to, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vacenic acid, linoleic acid, linoelaidoco acid, a-linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexenic acid, hexadecatrienoic acid, stearidonic acid, eicosatrienoic acid, eicosatetraenoic acid, heneicosapentaenoic acid, clupadonic acid, osbond acid, (9Z, 12Z, 15Z, 18Z, 21 Z) -tetracosa-9,12,15,18,21 - pentaenoic acid, nisinic acid, y-linolenic acid, eicosadienic acid, di-homo-y-linolenic acid, docosadienic acid, adrenic acid, tetracosatetraenoic acid, (6Z, 9Z, 12Z, 15Z, 18Z) -tetracosa-6,9, 12,15,18-pentaenoic, (Z) -Eicos-ll-enoic acid, mead acid, erucic acid, nervonic acid, rumenic acid, a-calendic acid, P-calendic acid, alligator acid, a-ellanoic acid, P-eleoesteárico, catálpico acid, punícic acid, rumelenic acid, a-par inaric acid, P-parinic acid, bosseopentaenoic acid, pinolenic acid and podocápric acid. In addition, each of R14, R15, R16 and R17 is independently, in each occurrence, hydrogen or a radical derived from coconut oil, beef fat or tall oil fatty acids (TOFA).
[00172] Preferably, imidazoline is a compound of formula (I), wherein R1 is unsubstituted C2-C6 alkyl; R2 is -C17H35, -C17H33 or -C17H31; R3 is -CFhCHiCChR6, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, R3 is -CH2CH2CO2); R4 is hydrogen; and R5 is hydrogen.
[00173] Alternatively, imidazoline is a compound of the formula (I), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, in which R12 is hydrogen and R13 is -COR14, where R14 is -C17H35, -C17H33 or -C17H31; R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, R3 is -CH2CH2CO2); R4 is hydrogen; and R3 is hydrogen.
[00174] Additionally, imidazoline is a compound of the formula (I), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, where each of R12 and R13 is -alkyl-C2-CO2R17, where R17 is hydrogen or is absent (for example, R12 is -alkyl-C2-CO2 '); R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-COC alkyl or Re is absent (for example, R3 is -CH2CH2CO2); R4 is hydrogen; and R5 is hydrogen.
[00175] Additionally, imidazoline is a compound of the formula (II), wherein R1 is unsubstituted C2-C6 alkyl; R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), C1-6 alkyl or Re is absent (for example, R3 is -CH2CH2CO2); Rx is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, Rx is - CH2CH2CO2); R4 is hydrogen; and R5 is hydrogen.
[00176] Imidazoline can be a compound of the formula (II), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, where R12 is hydrogen and R13 is -COR14, where R14 is -C17H35, - C17H33 or -C17H31; R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, R3 is -CH2CH2CO2); Rx is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-CÓ alkyl or Re is absent (for example, Rx is -CH2CH2CO2 ‘); R4 is hydrogen; and R5 is hydrogen.
[00177] Imidazoline can be a compound of formula (II), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, in which each of R12 and R13 is -alkyl-C2-CO2R17, where R17 is hydrogen or is absent (for example, R12 is -alkyl-C2-CO2); R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, R3 is -CH2CH2CO2); Rx is - CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, Rx is -CH2CH2CO2); R4 is hydrogen; and R5 is hydrogen.
[00178] Imidazoline can be a compound of the formula (III), wherein R1 is unsubstituted C2-COCalkyl; R2 is -C17H35, -C17H33 or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[00179] Imidazoline can be a compound of the formula (III), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, in which R12 is hydrogen and R13 is -COR14, where R14 is -C17H35, - C17H33 or -C17H31; R2 is -C17H35, -C17H33 or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[00180] Imidazoline can be a compound of the formula (III), in which R1 is linear C-2 alkyl, substituted with a substituent which is an -N (R12) (R13) terminal, in which each of R12 and R13 is -alkyl-Ci-CChR17, where R17 is hydrogen or is absent (for example, R12 is -alkyl-Ci-CCE); R2 is -C17H35, -C17H33 or -C17H31; R4 is hydrogen; and R5 is hydrogen.
[00181] It is understood, where explicitly presented or not, that formula (I), formula (II) and formula (III) are each intended to encompass tautomeric, racemic, enantiomeric, diastereomeric, zwiterionic and salt forms of said formulas. Imidazolines can exist in a zwitterionic form where R3 and / or Rx is derived from an acrylic acid.
[00182] The imidazoline compound can be present in the compositions in an amount of 1% by weight to 50% by weight, 2% by weight to 40% by weight, 3% by weight to 30% by weight, 4% by weight to 20% by weight, 5% by weight to 17% by weight, 6% by weight to 16% by weight, 7% by weight to 15% by weight, 8% by weight to 14% by weight, 9% by weight to 13% by weight or 10% by weight to 12% by weight, based on the total weight of the composition. The imidazoline compound can make up about 1% by weight, about 2% by weight, about 3% by weight, about 4% by weight, about 5% by weight, about 6% by weight, about 7% by weight, about 8% by weight, about 9% by weight, about 10% by weight, about 11% by weight, about 12% by weight, about 13% by weight, about 14 % by weight, about 15% by weight, about 16% by weight, about 17% by weight, about 18% by weight, about 19% by weight or about 20% by weight of the composition, based in the total weight of the composition. The composition can comprise about 11% by weight of the imidazoline compound, based on the total weight of the composition. The composition can comprise 11% by weight of the imidazoline compound, based on the total weight of the composition. B. Quaternary amines
[00183] The compositions described herein include a quaternary amine. Suitable quaternary amines include, but are not limited to, quaternary alkyl, hydroxyalkyl, alkylaryl, arylalkyl or arylamine salts.
[00184] Suitable alkyl, hydroxyalkyl, alkylaryl arylalkyl or arylamine quaternary salts include the alkylaryl, arylalkyl and arylamine quaternary salts of the formula [N + R3aR6aR7aR8a] [X "], where R5a, R6a, R7a and R8a contain a 18 carbon atoms and X is Cl, Br or I. For the quaternary amine, each of R5a, R6a, R7a and R8a can, independently, be selected from the group consisting of alkyl (for example, C1-6 alkyl), hydroxyalkyl (for example, C1-6 hydroxyalkyl) and arylalkyl (for example, benzyl). The mono or polycyclic aromatic amine salt with an alkyl or alkylaryl halide includes salts of the formula [N + R3aR6aR7aR8a] [X-] where R5a, R6a, R7a and R8a contain from one to 18 carbon atoms and X is Cl, Br or I.
[00185] Suitable quaternary ammonium salts include, but are not limited to, tetramethyl ammonium chloride, tetraethyl ammonium chloride, tetrapropyl ammonium chloride, tetrabutyl ammonium chloride, tetrahexyl ammonium chloride, tetraoctyl ammonium chloride benzyltrimethyl ammonium, benzylatriethyl ammonium chloride, phenyltrimethyl ammonium chloride, phenyltriethyl ammonium chloride, cetyl benzyladimethyl ammonium chloride, hexadecyl trimethyl ammonium chloride, dimethyl alkyl benzyl quaternary ammonium compounds, quaternary ammonium quaternary ammonium compounds trimethyl benzyl and trialkyl benzyl quaternary ammonium compounds, where the alkyl group may contain between about 1 and about 24 carbon atoms, about 10 and about 18 carbon atoms, or about 12 to about 16 carbon atoms , such as, for example, benzyl chloride C12-16 dimethyl ammonium. Suitable quaternary ammonium compounds (quats) include, but are not limited to, quaternary ammonium compounds of trialkyl, dialkyl, dialkoxy alkyl, monoalkoxy, benzyl and imidazolinium, salts thereof, the like and combinations thereof. The quaternary ammonium salt can be a quaternary amyl amine alkylamino salt, a quaternary ammonium amine benzyl triethanolamine salt or a quaternary ammonium benzyl salt dimethylaminoethanolamine.
[00186] Quaternary amine can be a benzalkonium salt represented by the formula:
where n is 8, 10, 12, 14, 16 or 18; and X is Cl, Br or I.
[00187] The quaternary amine can be a mixture of benzalkonium salts where n is 8, 10, 12, 14, 16 and 18.
[00188] The quaternary amine can be a mixture of benzalkonium salts where n is 12.14, 16 and 18.
[00189] The quaternary amine can be a mixture of benzalkonium salts where n is 12.14 and 16.
[00190] The quaternary amine can be a mixture of benzalkonium salts where n is 12.14, 16 and 18 and X is Cl.
[00191] The quaternary amine can be a mixture of benzalkonium salts where n is 12.14 and 16 and X is Cl.
[00192] The quaternary amine can be a quaternary alkyl pyridinium salt, such as those represented by the general formula:
where R9a is an alkyl group, an aryl group or an arylalkyl group, wherein said alkyl groups have from 1 to about 18 carbon atoms and B is Cl, Br or I. Among these compounds are alkyl pyridinium salts and alkyl benzyl pyridinium quats. Exemplary compounds include methyl pyridinium chloride, ethyl pyridinium chloride, propyl pyridinium chloride, butyl pyridinium chloride, octyl pyridinium chloride, decyl pyridinium chloride, lauryl pyridinium chloride, cetyl pyridinium chloride, benzyl pyridinium chloride and an alkyl pyridinium chloride benzyl pyridinium, preferably wherein the alkyl is a CI-CÓ hydrocarbyl group.
[00193] Quaternary amine can be present in the compositions in an amount of 0.1% by weight to 80% by weight, 1% by weight to 40% by weight, 5% by weight to 35% by weight, 10% by weight weight at 30% by weight, 15% by weight at 25% by weight, 16% by weight at 24% by weight, 17% by weight at 23% by weight, 18% by weight at 22% by weight or 19% by weight weight at 21% by weight, based on the total weight of the composition. The quaternary amine constitutes about 5% by weight, about 6% by weight, about 7% by weight, about 8% by weight, about 9% by weight, about 10% by weight, about 11% by weight, about 12% by weight, about 13% by weight, about 14% by weight, about 15% by weight, about 16% by weight, about 17% by weight, about 18% by weight. weight, about 19% by weight, about 20% by weight, about 21% by weight, about 22% by weight, about 23% by weight, about 24% by weight, about 25% by weight , about 26% by weight, about 27% by weight, about 28% by weight, about 29% by weight, about 30% by weight, about 31% by weight, about 32% by weight, about 33% by weight, about 34% by weight or about 35% by weight of the composition, based on the total weight of the composition. The quaternary amine is present in an amount of about 20% by weight or about 21% by weight, based on the total weight of the composition. The quaternary amine is present in an amount of 20.5% by weight, based on the total weight of the composition.
[00194] The composition may include 5% by weight to 35% by weight of the quaternary amine comprising benzyl C12 dimethyl ammonium chloride (e.g., 4% by weight to 20% by weight, based on the total weight of the composition), chloride benzyl Cu dimethyl ammonium (for example, 1% by weight to 10% by weight, based on the total weight of the composition), benzyl chloride CIÓ dimethyl ammonium (for example, 0.1% by weight to 5% by weight, based on the total weight of the composition) and benzyl Cis dimethyl ammonium chloride (e.g. 0.5% by weight or less, based on the total weight of the composition). The composition can include about 20% by weight or about 21% by weight of quaternary amine comprising benzyl chloride Cn dimethyl ammonium (e.g., 14.5% by weight, based on the total weight of the composition), benzyl chloride CM dimethyl ammonium (for example, 5% by weight, based on the total weight of the composition), benzyl chloride CM dimethyl ammonium (for example, 1% by weight, based on the total weight of the composition) and benzyl chloride CM dimethyl ammonium (for example, 0.2% by weight or less, based on the total weight of the composition). ç. Phosphonium compounds
[00195] The compositions described herein include at least one phosphonium compound and, in particular, a phosphonium salt. Suitable phosphonium salts include, but are not limited to, alkyltris (hydroxiorgan) phosphonium salts, alkenyltris (hydroxyiorgan) phosphonium salts and tetracis (hydroxyiorgan) phosphonium salts. The alkyltris (hydroxyiorgan) phosphonium salts can be C1-C3-alkyl tris (hydroxymethyl) phosphonium salts. Alkenyltris (hydroxyiorgan) phosphonium salts can be C2-C3-tris (hydroxymethyl) phosphonium alkenyl salts. The tetracis (hydroxyiorgan) phosphonium salts can be tetracis (hydroxymethyl) phosphonium salts including, but not limited to, tetracis (hydroxymethyl) phosphonium (THPS), tetracis (hydroxymethyl) phosphonium chloride, tetracis (hydroxymethyl) phosphate phosphonium, tetracis (hydroxymethyl) phosphonium format, tetracis (hydroxymethyl) phosphonium and tetracis (hydroxymethyl) phosphonium oxalate. The phosphonium salt can be tetracis (hydroxymethyl) phosphonium (THPS) sulfate.
[00196] The phosphonium salt can be present in the compositions in an amount of 0.1% by weight to 80% by weight, 0.5% by weight to 50% by weight, 1% by weight to 14% by weight, 2% by weight to 13% by weight, 3% by weight to 12% by weight, 4% by weight to 11% by weight, 5% by weight to 10% by weight, 6% by weight to 9% by weight or 7% by weight to 8% by weight, based on the total weight of the composition. The phosphonium salt constitutes about 1% by weight, about 2% by weight, about 3% by weight, about 4% by weight, about 5% by weight, about 6% by weight, about 7 % by weight, about 8% by weight, about 9% by weight, about 10% by weight, about 11% by weight, about 12% by weight, about 13% by weight or about 14% weight of the composition, based on the total weight of the composition. The phosphonium salt can be present in an amount of about 7% by weight, based on the total weight of the composition. The phosphonium salt can be present in an amount of 7.5% by weight, based on the total weight of the composition. d. Demulsifiers
[00197] The compositions described herein may include a demulsifier (also referred to as an emulsion breaker). Suitable emulsion breakers include, but are not limited to, dodecylbenzylsulfonic acid (DDBSA), the sodium salt of xylenesulfonic acid (NAXSA), epoxylated and propoxylated compounds, surfactants and anionic, cationic and non-ionic resins, such as polyoxyalkylenes, polymers of vinyl, polyamines, polyamides, phenolics and silicone polyethers. The emulsion breaker can be a vinyl polymer, such as: acrylic acid, polymer with t-butylphenol, phonnaldehyde, maleic anhydride, propylene oxide and ethylene oxide (CAS registration number: 178603-70-8).
[00198] The demulsifier may be present in an amount of 0.1% by weight to 30% by weight, 0.5% by weight to 10% by weight or 1% by weight to 5% by weight, based on weight total composition. The demulsifier constitutes about 1% by weight, about 2% by weight, about 3% by weight, about 4% by weight or about 5% by weight of the composition, based on the total weight of the composition. The compositions comprise about 2% by weight or about 3% by weight of the demulsifier, based on the total weight of the composition. The composition comprises 2.6% by weight of the demulsifier, based on the total weight of the composition. and. Synergistic
[00199] The compositions described herein may include a synergistic component. Suitable synergistic compounds include, but are not limited to, thioglycolic acid, 3,3'-dithiodipropionic acid, thiosulfate, thiourea, 2-mercaptoethanol, L-cysteine and tert-butyl mercaptane. The synergistic compound can be 2-mercaptoethanol.
[00200] The synergetic can be present in an amount of 0.01% by weight to 10% by weight, 0.1% by weight to 8% by weight, 0.5% by weight to 7% by weight, 1% by weight at 6% by weight, 2% by weight at 5% by weight or 3% by weight at 4% by weight, based on the total weight of the composition. The synergetic can make up about 0.5% by weight, about 1% by weight, about 1.5% by weight, about 2.0% by weight, about 2.5% by weight, about 3 , 0% by weight, about 3.5% by weight, about 4.0% by weight, about 4.5% by weight, about 5.0% by weight, about 5.5% by weight or about 6.0% by weight of the composition, based on the total weight of the composition. The composition can comprise about 3.5% by weight of the synergetic, based on the total weight of the composition. The composition can comprise 3.5% by weight of the synergetic, based on the total weight of the composition. f. Solvents
[00201] The compositions described herein may include a solvent. Suitable solvents include, but are not limited to, alcohols, hydrocarbons, ketones, ethers, aromatics, amides, nitriles, sulfoxides, esters, glycol ethers, aqueous systems and combinations thereof. The solvent can be water, isopropanol, methanol, ethanol, 2-ethylhexanol, heavy aromatic naphtha, toluene, ethylene glycol, ethylene glycol monobutyl ether (EGMBE), diethylene glycol monoethyl ether or xylene. Representative polar solvents suitable for formulation with the composition include water, brine, seawater, alcohols (including straight or branched aliphatic, such as methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, etc.), glycols and derivatives (ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, ethylene glycol monobutyl ether, etc.), ketones (cyclohexanone, diisobutyl ketone), N -methylpyrrolidinone (NMP), N, N-dimethylformamide and the like. Representative non-polar solvents suitable for formulation with the composition include aliphatics, such as pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel and the like; aromatics, such as toluene, xylene, heavy aromatic naphtha, fatty acid derivatives (acids, esters, amides) and the like.
[00202] The solvent can be methanol, isopropanol, 2-ethylhexanol or a combination thereof. In addition, the solvent can be methanol, isopropanol, 2-ethylhexanol, water or a combination thereof.
[00203] A composition of the invention may comprise 0 to 99 percent, 1 to 98 percent, 10 to 80 percent, 20 to 70 percent, 30 to 60 percent or 40 to 55 percent by weight of one or more more solvents, based on the total weight of the composition.
[00204] A composition of the invention can comprise about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90% or about 95% by weight of one or more solvents, based on weight total composition. A composition of the invention comprises about 40% of one or more alcoholic solvents and about 15% of water. A composition of the invention can comprise about 40% of a methanol / isopropanol mixture and about 15% of water. A composition of the invention can comprise 40% of a methanol / isopropanol mixture and 14.9% of water.
[00205] The compositions of the invention optionally include one or more additional additives. Suitable additives include, but are not limited to, corrosion inhibitors, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, hydrogen sulfite removers, gas hydrate inhibitors, biocides, modifiers of pH and surfactants. g. Corrosion inhibitors
[00206] Corrosion inhibitors suitable for inclusion in the compositions include, but are not limited to, mono-, di- or trialkyl or alkylaryl phosphate esters; phosphate esters of hydroxylamines; phosphate esters of polyols; and monomeric or oligomeric fatty acids.
[00207] Suitable mono-, di- and trialkyls, as well as phosphate esters of alkylaryl and phosphate esters of mono, di and triethanolamine typically contain between 1 to about 18 carbon atoms. Preferred mono-, di- and trialkyl phosphate esters, alkylaryl or arylalkyl phosphate esters are those prepared by reacting a C3-C18 aliphatic alcohol with phosphorus pentoxide. The phosphate intermediate exchanges its ester groups with triethyl phosphate with triethyl phosphate producing a wider distribution of alkyl phosphate esters. Alternatively, the phosphate ester can be prepared by mixing with an alkyl diester, a mixture of lower alkyl alcohols or diols. Low molecular weight alkyl alcohols or diols preferably include COC to C11 alcohols or diols. In addition, phosphate esters of polyols and their salts containing one or more 2-hydroxyethyl groups and phosphate esters of hydroxylamine obtained by reacting polyphosphoric acid or phosphorus pentoxide with hydroxylamines, such as diethanolamine or triethanolamine are preferred.
[00208] The corrosion inhibitor can be a monomeric or oligomeric fatty acid. Preferred are saturated and unsaturated C14-C22 fatty acids, as well as dimer products, trimers and oligomers obtained by polymerizing one or more of such fatty acids. H. Asphaltene inhibitors
[00209] Suitable asphaltene inhibitors include, but are not limited to, aliphatic sulfonic acids; alkyl aryl sulfonic acids; aryl sulfonates; lignosulfonates; alkylphenol / aldehyde resins and similar sulfonated resins; polyolefin esters; polyolefin imides; polyolefin esters with alkyl, alkylenophenyl or alkylenopyridyl functional groups; polyolefin amides; polyolefin amides with alkyl, alkylenophenyl or alkylenopyridyl functional groups; polyolefin imides with alkyl, alkenophenyl or alkylenopyridyl functional groups alkenyl / vinyl pyrrolidone copolymers; polyolefin graft polymers with maleic anhydride or imidazole vinyl; hyper-branched polyester amides; polyalkoxylated asphaltenes, amphoteric fatty acids, alkyl succinate salts, sorbitan monooleate and siccinic polyisobutylene anhydride. i. Paraffin inhibitors
[00210] Suitable paraffin inhibitors include, but are not limited to, paraffin crystal modifiers and dispersant / crystal modifier combinations. Suitable paraffin crystal modifiers include, but are not limited to, alkyl acrylate copolymers, vinyl pyridine acrylate copolymers, ethylene vinyl acetate copolymers, maleic ester anhydride, branched polyethylenes, naphthalene, anthracene, microcrystalline wax and / or asphaltenes. Suitable dispersants include, but are not limited to, dodecyl benzene sulfonate, oxyalkylated alkylphenols and oxyalkylated alkylphenolic resins. j. Fouling inhibitors
[00211] Suitable scale inhibitors include, but are not limited to, phosphates, phosphate esters, phosphoric acids, phosphonates, phosphonic acids, polyacrylamides, acrylamide-methyl propane sulfonate / acrylic acid (AMPS / AA) copolymer salts, phosphinated maleic copolymer (PHOS / MA) and salts of a polymeric acid / acrylic acid / acrylamido-methyl propane sulfonate terpolymer (PMA / AMPS). k. Emulsifiers
Suitable emulsifiers include, but are not limited to, salts of carboxylic acids, products of acylation reactions between carboxylic acids or carboxylic anhydrides and amines and alkyl, acyl derivatives and saccharide amide (alkyl saccharide emulsifiers). l. Water clarifiers
[00213] Suitable water clarifiers include, but are not limited to, inorganic metal salts, such as alum, aluminum chloride and aluminum hydrochloride or organic polymers, such as acrylic acid-based polymers, acrylamide-based polymers, polymerized amines, alkanolamines, thiocarbamates and cationic polymers, such as diallyldimethylammonium chloride (DADMAC). m. Dispersants
[00214] Suitable dispersants include, but are not limited to, aliphatic phosphonic acids with 2 to 50 carbons, such as hydroxyethyl diphosphonic acid and phosphonic aminoalkyl acids, for example, polyamine methylene phosphonates with 2 to 10 N atoms, for example, each carrying at least one group of phosphonic methylene acid; examples of the latter are ethylenediamine tetra (methylene phosphonate), diethylene triamine penta (methylene phosphonate) and triamine- and tetramine-polymethylene phosphonates with 2 to 4 methylene groups between each N atom, at least 2 of the numbers of methylene groups in each phosphonate being different. Other suitable dispersing agents include lignin or lignin derivatives, such as lignosulfonate and naphthalene sulfonic acid and derivatives. H. Hydrogen sulfite removers
[00215] Suitable additional hydrogen sulfite removers include, but are not limited to, oxidizers (eg, inorganic peroxides, such as sodium peroxide or chlorine dioxide), aldehydes (eg, 1 to 10 carbons, such as formaldehyde or glutaraldehyde or (meth) acrolein), triazines (for example, monoethanol amine triazine, monomethylamine triazine and triazines of multiple amines or mixtures thereof) and glyoxal. The. Gas hydrate inhibitors
[00216] Suitable gas hydrate inhibitors include, but are not limited to, thermodynamic hydrate inhibitors (THI), kinetic hydrate inhibitors (KHI) and anti-agglomerates (AA). Suitable thermodynamic hydrate inhibitors include, but are not limited to, NaCl salt, KC1 salt, CaCh salt, MgCC salt, NaBn salt, format pickles (eg, potassium format), polyols (such as glucose , sucrose, fructose, maltose, lactose, gluconate, monoethylene glycol, diethylene glycol, triethylene glycol, mono-propylene glycol, dipropylene glycol, tripropylene glycols, tetrapropylene glycol, monobutylene glycol, dibutylene glycol, tributylene glycol, glycerol, diglycerol, triglycerol and triglycerol and triglycerol sugar (eg, sorbitol, mannitol)), methanol, propanol, ethanol, glycol ethers (such as diethylene glycol monomethyl, ethylene glycol monobutyl ether) and alkyl or cyclic alcohol esters (such as ethyl lactate, butyl lactate, methyl ethyl benzoate ). Suitable kinetic hydrate inhibitors and anti-agglomerates include, but are not limited to, polymers and copolymers, polysaccharides (such as hydroxyethylcellulose (HEC), carboxymethylcellulose (CMC), starch, starch and xanthan derivatives), lactams (such as polyvinylcaprolactam, polyvinyl lactam), pyrrolidones (such as polyvinyl pyrrolidone of various molecular weights), surfactants (such as fatty acid salts, ethoxylated alcohols, propoxylated alcohols, sorbitan esters, ethoxylated sorbitan esters, polyglycerides and polyglycerides alkyl polyglycosides, alkyl sulfates, alkyl sulfonates, alkyl sulfonates ester, aromatic alkyl sulfonates, alkyl betaine, alkyl starch betaine), hydrocarbon based dispersants (such as lignosulfonates, iminodisuccinates, polyaspartates), amino acids and proteins. P. Biocides
[00217] Suitable additional biocides include, but are not limited to, oxidizing and non-oxidizing biocides. Suitable non-oxidizing biocides include, for example, aldehydes (for example, formaldehyde, glutaraldehyde and acrolein), amine-like compounds (for example, quaternary amine compounds and cocodiamine), halogenated compounds (for example, bronopol and 2-2-dibromo- 3-nitrilopropionamide (DBNPA)), sulfur compounds (for example, isothiazolone, carbamates and metronidazole) and quaternary phosphonium salts (for example, tetracis (hydroxymethyl) phosphonium (THPS) sulfate). Suitable oxidizing biocides include, for example, sodium hypochlorite, trichloroisocyanuric acids, dichloroisocyanuric acid, calcium hypochlorite, lithium hypochlorite, chlorinated hydantoins, stabilized sodium hypobromide, activated sodium bromide, brominated hydantoins, chlorine dioxide, ozone and peroxides. q. pH modifiers
[00218] Suitable pH modifiers include, but are not limited to, alkali hydroxides, alkaline carbonates, alkaline bicarbonates, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal bicarbonates and mixtures or combinations thereof. Exemplary pH modifiers include NaOH, KOH, Ca (OH) 2, CaO, Na2CO3, KHCO3, K2CO3, NaHCO3, MgO and Mg (OH) 2j r. Surfactants
[00219] Suitable surfactants include, but are not limited to, anionic surfactants, cationic surfactants, zwitterionic surfactants and non-ionic surfactants. Anionic surfactants include alkyl aryl sulfonates, olefin sulfonates, paraffin sulfonates, alcohol sulfates, alcohol sulfate ethers, alkyl carboxylates and alkyl carboxylates and phosphate ethoxylated alkyl and alkyl esters and sulfosuccinates and sulfosuccinates and monosulfate dihydrates. Cationic surfactants include quaternary alkyl trimethyl ammonium salts, quaternary alkyl dimethyl benzyl ammonium salts, quaternary dialkyl dimethyl ammonium salts and imidazoline salts. Nonionic surfactants include alkoxylated alcohols, alkoxylated alkylphenol, ethylene block copolymers, propylene and butylene oxides, alkyl dimethyl amine oxides, alkyl-bis (2-hydroxyethyl) amine oxides, alkyl amidopropyl dimethyl amine oxides, 2-alkylamidopropyl-bis-amidopropyl hydroxyethyl) amine oxides, alkyl polyglycosides, polyalkoxylated glycerides, sorbitan esters and polyalkoxylated sorbitan esters and alkyl polyethylene glycol esters and diesters. Also included are betaines and sultans, amphoteric surfactants, such as alkyl amfoacetates and amphodiacetates, alkyl amphopropripionates and amphodipropionates and alkyliminodiproprionate.
[00220] The surfactant can be a compound of quaternary ammonium, an amine oxide, an ionic or non-ionic surfactant or any combination thereof. Suitable quaternary amine compounds include, but are not limited to, alkyl benzyl ammonium chloride, benzyl cocoalkyl (C 2 -C 8) dimethylammonium chloride, dicocoalkyl (C 12 -C 8) dimethylammonium chloride, dichloro dimethylammonium chloride, methyl di ( hydrogenated alkyl tea) quaternary dimethyl ammonium, methyl bis (2-hydroxyethyl cocoalkyl (C1 -Cis) ammonium chloride, dimethyl (2-ethyl) sulfate methyl ammonium, ammonium chloride, n-dodecylbenzyldimethylammonium chloride, n-octadecylbenzimildyl chloride, n-dodecyltrimethylammonium sulfate, soybean alkyltrimethylammonium chloride and alkyl (2-ethylhexyl) dimethyl ammonium methylated quaternary ammonium hydrogenated cap. s. Additional components
[00221] Compositions prepared according to the invention may additionally include additional functional agents or additives that provide a beneficial property. Additional agents or additives will vary according to the particular composition being manufactured and its intended use, as perceived by one skilled in the art.
[00222] Alternatively, the compositions do not contain any additional agents or additives. 3. Summary
[00223] The compounds and compositions of the invention can be better understood in conjunction with the following synthetic schemes and methods which illustrate a means by which the compounds can be prepared. Layout 1

[00224] As shown in scheme 1, compounds of formula (1) can be prepared by reacting an imidazoline of formula (2) with an acrylic acid of formula (3), wherein each of R1, R2, R3, R4, R5 , Ra, Rb, Rc and Re is as previously defined. The imidazoline of formula (2) can be prepared from the reaction of a diamine, such as ethylene diamine (EDA), diethylene triamine (DETA) or triethylene tetramine (TETA) with a long-chain fatty acid, such as tall (TOFA). The compound of formula (3) introduced in the representative reaction schemes, in general, includes unsaturated α, β-carboxylic fatty acids and amide and ester derivatives thereof; unsaturated sulfonic and phosphonic fatty acids; and their combinations. The compound of formula (3) can be selected from the group consisting of substituted and unsubstituted α, unsaturated β-carboxylic acids and amide and ester derivatives thereof, having from 3 to about 11 carbon atoms or a salt of the same; substituted and unsubstituted α, β-unsaturated fatty acids having from 2 to about 11 carbon atoms or a salt thereof; and combinations thereof.
[00225] For scheme 1, each of R4, R5, Ra, Rb, Rc and Re is hydrogen. In addition, R1 is C2-C10 alkyl, C2-C8 alkyl or C2-COC alkyl; and each of R4, R Ra, Rb, Rc and Re is hydrogen. In addition, R1 is C2-C10 alkyl, C2-C8 alkyl or C2-C6 alkyl; R2 is a radical Cp; and each of R4, R5, Ra, Rb, Rc and Re is hydrogen. Also, R1 is C2-C10 alkyl, C2-C8 alkyl or C2-C6 alkyl; R2 is a radical derived from coconut oil, beef fat or tall oil fatty acids (TOFA); and each of R4, R5, Ra, Rb, Rc and Re is hydrogen. Layout 2

[00226] As shown in scheme 2, compounds of formula (4) can be prepared by reacting an imidazoline of formula (2) with an acrylic acid of formula (3), wherein each of R1, R2, R3, Rx, R4 , R5, Ra, Rb, Rce Re is as previously defined.
[00227] For scheme 2, each of R4, R5, Ra, Rb, Rc and Re is hydrogen. Additionally, R1 is linear C-2 alkyl, substituted with a substituent that is a -N (R12) (R13) terminal, where R12 is hydrogen and R13 is -COR14, where R14 is -C17H35, -C17H33 or -C17H31 ; R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), C1-6 alkyl or Re is absent (for example, R3 is -CH2CH2CO2); Rx is -CH2CH2CO2Re, where Re is hydrogen (-H), C1-6 alkyl or Re is absent (for example, Rx is -CH2CH2CO2 ‘); R4 is hydrogen; and R5 is hydrogen. In addition, R1 is linear C-2 alkyl, substituted with a substituent that is a -N (R12) (R13) terminal, where each of R12 and R13 is -C2-CO2-CO2R17, where R17 is hydrogen or is absent (for example, R12 is -C2-alkyl-CO2;); R2 is -C17H35, -C17H33 or -C17H31; R3 is -CH2CH2CO2Re, where Re is hydrogen (-H), CI-C6 alkyl OR Re is absent (for example, R3 is -CH2CH2CO2); Rx is - CH2CH2CO2Re, where Re is hydrogen (-H), C1-6 alkyl or Re is absent (for example, Rx is -CH2CH2CO2); R4 is hydrogen; and R5 is hydrogen.
[00228] Imidazolines for use with compositions of the invention may also be commercially available.
[00229] The compounds can be further modified, for example, by manipulating the substituents. These manipulations may include, but are not limited to, reduction reactions, oxidation, organometallic cross-coupling, alkylation, acylation and hydrolysis which are commonly known to those skilled in the art. In some cases, the order of carrying out the previous reaction schemes may vary to facilitate the reaction or to avoid unwanted reaction products. 4. Methods of Use
[00230] The compositions of the invention can be used in any industry where it is desirable to control the formation of biofilm and / or inhibit corrosion on a surface. The compositions can preferably be used as biocides for use in oil and gas applications. By treating a stream of gas or liquid with an effective amount of a composition of the invention, the compositions can provide significant planktonic death and better control of the biofilm by slowing the biofilm redevelopment kinetics.
[00231] The compositions can be used in water systems, condensate / oil / gas systems or any combination thereof.
[00232] The compositions can be applied to a gas or liquid produced or used in the production, transportation, storage and / or separation of crude oil or natural gas.
[00233] The compositions can be applied to a gas stream used or produced in a coal-fired power generation process, such as a coal-fired power plant.
[00234] The compositions can be applied to a gas or liquid produced or used in a waste water process, a farm, an abattoir, a landfill, a municipal waste water plant, a coal coking process or a biofuel.
[00235] A fluid into which the compositions can be introduced can be an aqueous medium. The aqueous medium can comprise water, gas and optionally liquid hydrocarbon. A fluid into which the compositions can be introduced can be a liquid hydrocarbon. The liquid hydrocarbon can be any type of liquid hydrocarbon including, but not limited to, crude oil, heavy oil, processed residual oil, bituminous oil, coking oil, coking gas oil, fluid catalytic cracker feeds, gas, naphtha, fluid catalytic cracking sludge, diesel fuel, fuel oil, jet fuel, gasoline and kerosene. The fluid or gas can be a refined hydrocarbon product.
[00236] A fluid or gas treated with a composition of the invention can be at any selected temperature, such as room temperature or an elevated temperature. The fluid (for example, liquid hydrocarbon) or gas can be at a temperature of about 40 ° C to about 250 ° C. The fluid or gas can be at a temperature of -50 ° C to 300 ° C, 0 ° C to 200 ° C, 10 ° C to 100 ° C or 20 ° C to 90 ° C.
[00237] The compositions of the invention can be added to a fluid in various percent water levels. For example, the percentage of water can be from 0% to 100% volume / volume (v / v), from 1% to 80% v / v or from 1% to 60% v / v. The fluid can be an aqueous medium that contains various levels of salinity. The fluid can have a salinity of 0% to 25%, about 1% to 24%, or about 10% to 25% weight / weight (w / w) of total dissolved solids (TDS).
[00238] The fluid or gas into which the compositions of the invention are introduced may be contained in and / or exposed to many different types of apparatus. For example, the fluid or gas may be contained in an apparatus that transports fluid or gas from one point to another, such as an oil and / or gas pipeline. The apparatus may be part of an oil and / or gas refinery, such as a pipe, a separation vessel, a dehydration unit or a gas line. The fluid can be contained in and / or exposed to an apparatus used in the extraction and / or production of oil, such as a spring. The device can be part of a coal-fired power plant. The apparatus may be a remover (for example, a wet exhaust gas desulfurizer, a dust-dried absorbent, a dry sorbent injector, a dusting tower, a contact tower or bubble or the like). The device can be a cargo vessel, a storage vessel, a support tank or a pipe that connects the tanks, vessels or processing units. The fluid or gas can be contained in water systems, condensate / oil systems / gas systems or any combination thereof.
[00239] The compositions of the invention can be introduced into a fluid or gas by any appropriate method to ensure dispersion through the fluid or gas. The inhibitory composition is added at one point in a flow line upstream of the point at which corrosion prevention is desired. The compositions can be injected using mechanical equipment, such as chemical injection pumps, T connections, injection accessories, atomizers, feathers and the like. The compositions of the invention can be introduced with or without one or more additional polar or non-polar solvents, depending on the application and requirements. The compositions of the invention can be pumped into an oil and / or gas pipeline using an umbilical line. Capillary injection systems can be used to dispense the compositions to a selected fluid. The compositions can be introduced into a liquid and mixed. The compositions can be injected into a gas stream as an aqueous or non-aqueous solution, mixture or slurry. The fluid or gas can be passed through an absorption tower comprising a compound or composition of the invention.
[00240] The compositions can be applied to a fluid or gas to provide any selected concentration. In practice, the compositions of the invention are typically added to a flow line to provide an effective treatment dose of the described compositions from about 0.01 to about 10,000 ppm. The compositions can be applied to a fluid or gas to provide a total active concentration (eg, imidazoline, quaternary amine, phosphonium salt, demulsifier and synergetic) from about 1 parts per million (ppm) to about 1,000,000 ppm, about 1 ppm to about 100,000 ppm, about 10 ppm to about 75,000 ppm, about 10 ppm to about 10,000 ppm, about 50 ppm to about 10,000 ppm or about 100 ppm to about 500 ppm. The compositions can be applied to a fluid to provide an active concentration of about 10 ppm to about 10,000 ppm, about 10 ppm to about 500 ppm, about 50 ppm to about 500 ppm or about 100 ppm at about 500 ppm. The compositions are applied to a fluid or gas to provide an active concentration of about 50 ppm, about 100 ppm, about 150 ppm, about 200 ppm, about 250 ppm, about 300 ppm, about 350 ppm , about 400 ppm, about 450 ppm, about 500 ppm, about 550 ppm, about 600 ppm, about 650 ppm, about 700 ppm, about 750 ppm, about 800 ppm, about 800 ppm, about 850 ppm , about 900 ppm, about 950 ppm, or about 1,000 ppm. Each system may have its own dose level requirements, and the effective dose level of a composition to sufficiently reduce the rate of corrosion may vary with the system in which it is used.
[00241] The compositions can be applied continuously, in batch or a combination thereof. The doses of the composition can be continuous.
[00242] The doses of the composition may be intermittent (i.e. batch treatment).
[00243] The doses of the composition can be continuous / maintained and / or intermittent.
[00244] Dosage rates for continuous treatments typically range from about 10 to about 500 ppm or about 10 to about 200 ppm.
[00245] Dosage rates for batch treatments typically range from about 10 to about 10,000 ppm.
[00246] The composition can be applied as a pill to a pipe, providing a high dose (for example, 10,000 ppm) of the composition.
[00247] The flow rate of a flow line in which the composition is used can be between 0 and 100 feet per second or between 0.1 and 50 feet per second. In some cases, the compositions can be formulated with water in order to facilitate addition to the flow line.
[00248] The compositions can provide 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, 99%, 99.1 %, 99.2%, 99.3%, 99.4%, 99.5%, 99.6%, 99.7%, 99.8%, 99.9% or 100% planktonic death. The compositions can provide 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, 99%, 99.1%, 99.2 %, 99.3%, 99.4%, 99.5%, 99.6%, 99.7%, 99.8%, 99.9% or 100% of planktonic death in a dynamic flow mesh test after a 4-hour contact period with the biocide composition .
[00249] The dynamic flow mesh can be characterized by a test system that supports approximately a selected volume of fluid (for example, 1.5 liters) that are continuously circulated over 1018 carbon steel bio-studies (for example, located in the 6 o'clock position of a modified Robbin device). The test fluid can be pumped through the system at a selected rate (for example, approximately 3.1 gallons per minute), which allows the deposition of microorganisms and solids in the bio-studies. The health of the microbial population can be monitored (for example, weekly) during the biofilm growth period (for example, 7 weeks) using ATP quantification. After completing the establishment of a mature biofilm, a study of the biocide's effectiveness can be started. During the study, samples of solid and fluid can be collected before and after biocide treatment at scheduled intervals (eg, 4 hours, 24 hours, 72 hours or 120 hours). A baseline reading (for example, solid and fluid samples) can be taken before adding the biocide to the individual flow mesh. To study how quickly a biofilm is able to redevelop itself after batch biocide treatment, the fluid treated with total biocide in each loop of the fluid can be removed from the system and untreated production fluid added back into the system. Additional solid samples (for example, biostudies) can be removed at selected time intervals (for example, 24, 48 and both 72 and 120 hours) after the new fluid has been added, in order to determine how quickly the biofilm was able to redevelop to their pre-treatment size.
[00250] The compounds, compositions, methods and processes of the invention will be better understood by reference to the following examples, which are intended for illustration and not to limit the scope of the invention. 5. Examples
[00251] The foregoing can be better understood by reference to the following examples, which are presented for the purposes of illustration and should not limit the scope of the invention.
[00252] Imidazolines can be prepared as described in examples 1 to 5 and as described in US patents Nos. 6,488,868, 7,057,050 and 7,951,754, the contents of which are incorporated by reference in full. Imidazolines can also be commercially available. Example 1

[00253] To prepare the previous imidazoline in which R2 is -C17H35, -C17H33 or -C17H31, six grams of tall oil fatty acid (TOFA) were placed in a 4-neck, 250 mL bottle equipped with a suspended shaker , thermocouple, addition funnel and a Dean-Stark pickup. TOFA was heated to 60 ° C and then 25 grams of N-propyl ethylenediamine were added in drops quickly. The resulting mixture turned from light yellow to dark red and became exothermic at 100 ° C. The mixture was then heated to 120 to 140 ° C for 3 hours. The hydrocarbon collected in the pickup returned to the bottle. The mixture was thereafter heated to 160 ° C for 1 hour, allowing water to be collected in the Dean-Stark pickup.
[00254] The resulting mixture was then heated to 165 ° C for 2 hours and then to 225 ° C for an additional hour, during which any additional evolved water was collected. A nitrogen sweep was applied and the speed of the suspended agitator was increased to facilitate the removal of water. After further heating the mixture to 225 ° C for an additional 1.5 hours, the reaction mixture was cooled and 65.9 grams of the resulting imidazoline mixture then reacted with 18.7 grams of acrylic acid which was carefully added in drops to the imidazoline product. A temperature increase of about 70 to 89 ° C was observed. After the exotherm ceased, the reaction temperature was raised to about 100 ° C for 2 hours. The resulting N-propyl-2-heptadecenyl imidazoline acrylate was recovered. Example 2

[00255] To prepare the previous imidazoline in which R2 is -C17H35, -C17H33 or -C17H31, six grams of tall oil fatty acid (TOFA) were placed in a 250-neck 4-neck flask equipped with a suspended stirrer , thermocouple, addition funnel and a Dean-Stark pickup. TOFA was heated to 60 ° C and then 28.5 grams (0.245 mol) of N-butylethylenediamine was added in drops quickly. The resulting mixture turned from light yellow to dark red and became exothermic at 84 ° C. The mixture was then heated to 160 ° C for 3.5 hours until no additional water had evolved. The hydrocarbon collected in the pickup returned to the bottle. The mixture was thereafter heated to 160 ° C for 1 hour, allowing water to be collected in the Dean-Stark pickup.
[00256] Fifty grams (0.132 mol) of the resulting mixture was then heated to 225 ° C for an additional hour, during which any further evolved water was collected. A nitrogen sweep was applied and the speed of the suspended agitator was increased to facilitate the removal of water. After further heating the mixture at 225 ° C for an additional 1.5 hours, the reaction mixture was cooled and 45.25 grams of the resulting imidazoline mixture then reacted with 10.4 grams of acrylic acid which was carefully added in drops to the imidazoline product. A temperature rise at about 88 ° C was observed. After the exotherm ceased, the reaction temperature was raised to about 120 ° C for 2 hours. The resulting N-butyl-2-heptadecenyl imidazoline acrylate was recovered. Example 3

[00257] To prepare the previous imidazoline in which R2 is -C17H35, -C17H33 or -C17H31, six grams of tall oil fatty acid (TOFA) were placed in a 4-neck, 250 mL bottle equipped with a suspended shaker , thermocouple, addition funnel and a Dean-Stark pickup. TOFA was heated to 60 ° C and 35.3 grams (0.265 mol) of N-hexylethylenediamine were added in drops quickly. The resulting mixture turned from light yellow to dark red and became exothermic at 87 ° C. The mixture was heated to 160 ° C for 3.5 hours until no additional water had evolved. The hydrocarbon collected in the pickup returned to the bottle. The mixture was thereafter heated to 160 ° C for 1 hour, allowing water to be collected in the Dean-Stark pickup.
[00258] Sixty-one grams of the resulting mixture was then heated to 225 to 230 ° C for an hour and then to 225 ° C for an additional hour, during which any further evolved water was collected. A nitrogen sweep was applied and the speed of the suspended agitator was increased to facilitate the removal of water. After further heating the mixture at 225 ° C for an additional 1.5 hours, the reaction mixture was cooled and 55.93 grams of the resulting imidazoline mixture then reacted in a 3-ml, 250-neck flask with 18.7 grams of acrylic acid that was carefully added in drops to the imidazoline product. A temperature rise at about 92 ° C was observed. After the exotherm ceased, the reaction temperature was raised to about 120 ° C for 2 hours. The resulting N-hexyl-2-heptadecenyl imidazoline acrylate was recovered. Example 4

[00259] To prepare the above imidazoline compound in which R2 and R14 are independently -C17H35, -C17H33 or -C17H31, 220.4 grams (0.78 moles) of a tall oil fatty acid mixture ("TOFA" -composed of about 46% oleic acid, about 41% linoleic acid, about 4% stearic acid and about 9% other acids) were weighed and placed in a four-necked, round-base flask of 500 mL equipped with a suspended stirrer, thermocouple, addition funnel and Dean-Stark pickup. TOFA was heated to about 70 ° C and 38.8 grams (0.38 moles) of diethylenetriamine were added in drops, with stirring. An exotherm of about 35 ° C was observed. The mixture was further heated to 130 ° C for 1 hour and 160 ° C for 2 hours. The mixture was then maintained at 250 ° C for 2 hours with a nitrogen gas sweep. 17.6 mL (about 86% of theoretical water for 100% of imidazoline formation) of water were collected. The mixture was cooled and 60.8 grams (0.84 moles) of glacial acrylic acid were added in drops, with stirring, which had an exotherm between 47 and 67 ° C. This final mixture was heated at 120 to 125 ° C for 2 hours to ensure a complete reaction. Example 5

[00260] To prepare the above imidazoline, where R2 is -C17H35, -C17H33 or -C17H31, 175 g (0.62 mol) of TOFA was placed in a 500-ml round neck four-neck flask equipped with a stirrer suspended, addition funnel, thermocouple and Dean-Stark pickup. The acid was heated to 60 ° C and a nitrogen gas sweep was maintained on the liquid's surface throughout the reaction. When the temperature reached 60 ° C, 82 g (0.8 mol) of DETA were added in drops quickly. An exotherm of about 40 ° C was observed. The mixture was heated to 175 ° C with stirring, until the theoretical amount of water for formation of amide (11 g) was collected. The infrared spectrum of the mixture at this point indicated the presence of amide (absorption at about 1630 and 1550 cm-1) and free N-H (absorption at about 3315 cm-1). The temperature was increased to 225 ° C and kept in it for 2 hours (84% of the theoretical amount of water for 100% of imidazoline formation was collected). The infrared spectrum showed the same two broad bands noted above and a sharper band, intense between them around 1,610 nm, indicating imidazoline.
[00261] 69.8 g (0.2 mol, assuming the composite molecular weight of the imidazoline amine is 349 g / mol) of the resulting imidazoline amine mixture were weighed in a 250-ml round neck four-neck flask equipped with a stirrer suspended, addition funnel and thermocouple. To this was added 43.2 g (0.6 mol) of acrylic acid via the addition funnel. The exotherm was noted and the mixture heated to 120 ° C for 2 hours. Biocide Test
[00262] The evaluation of the biocide compositions described here was carried out through a dynamic flow manipulation test where both planktonic and sessile organisms could be monitored. To begin this test, fluid from the field, as well as organisms grown from the field, were placed in the system and grown for approximately 7 weeks, providing a mature biofilm that can then be challenged by biocide treatment.
[00263] The test system supports approximately 1.5 liters of fluid, which are continuously circulated over 1018 carbon steel biostudies located at the 6 o'clock position of a modified Robbin device. The device supports a maximum of eight biostudies at the 6 o'clock position. The production fluid was pumped through the system at a rate of approximately 3.1 gallons per minute, which allows the deposition of microorganisms and solids in the biostudies. The health of the microbial population was monitored weekly during the growth period of the biofilm using ATP quantification.
[00264] After the completion of the establishment of a mature biofilm, the sessile death study was started. During the study, solid and fluid samples were collected before and after biocide treatment at scheduled intervals. The following chemicals were tested in the system: (study 1) THPS was tested against THPS / quat # 2, (study 2) THPS / quat # 1 and (study 3) THPS / quat / imidazoline. A baseline reading was taken, during all studies, before adding the chemical to the individual flow loop. This consisted of a fluid sample, as well as two biostudies. After removing the sample from the baseline, both (study 1) THPS and THPS / quat # 2, (study 2) THPS / quat # 1, (study 3) THPS / quat / imidazoline were added to a flow loop at predetermined concentration with a contact time of 4 hours. After 4 hours of treatment, a second sample of fluid and two coupons were removed from each loop of the flow. The total fluid in each loop of the stream was then removed from the system and untreated production fluid added back to mimic a batch biocide treatment followed by continued production. Additional biostudies were removed at 24, 48 and both 72 and 120 hours after the new fluid was added to determine how quickly the biofilm was capable of redevelopment at its pre-treatment size.
[00265] One of the characteristics of this chemistry is the best death of the biofilm that a formulation has when imidazoline is present, even if imidazoline itself does not have a better death in planktonic organisms. Figure 1 shows a death study of planktonic biocide efficacy where various amounts of imidazoline were mixed with a quaternary biocide. As the amount of imidazoline increased, microbial death decreased, as shown in figure 1.
[00266] Figure 2 is a compilation of three separate experiments that illustrate the ability to kill microbes present in a biofilm using THPS alone, THPS in combination with one of two different quats or THPS with one quat plus acrylated imidazoline. The initial data point before treatment is adjusted to 100% and all other readings are reported as a percentage change compared to the baseline. THPS alone provides death from the initial biofilm, but the biofilm is longer than it was before treatment in 24 hours. THPS plus quats provided better control with quat # 2, compared to THPS alone, but no improved control with quat # 1, Quat # 2 was N, N-dimethyl, N-alkyl-benzylammonium chloride in which the alkyl was a mixture alkyl groups C12, Ci4 and Ci6. The imidazoline used was commercially available under the brand name Clean N Cor from Nalco. THPS / quat / imidazoline provided a synergistic effect where growth of the biofilm was reduced to less than 0.3% of the initial size and maintained for at least 120 hours when the test was stopped.
[00267] Planktonic death in dynamic flow loops was also evaluated immediately after a contact time of 4 hours with the biocide. The results of this test are shown in Table 1. Compared to THPS alone, the addition of a quat does not provide any improved death. The addition of a quat plus imidazoline to THPS provided a synergistic effect where planktonic death was significantly improved, compared to THPS or THPS plus quat only. Table 1

quat # 1 = benzyl chloride- (linear C12-C16 alkyl) -dimethyl-ammonium quat # 2 = same quat as the THPS / quat / imidazoline mixture (without 0 imidazole)
[00268] Based on these results, a planktonic death study as described above and a static sessile death study were employed to determine the THPS / quat / imidazoline ratio that produces the most synergistic effect. The results indicated that the formulations entitled N-HF # 2 and N-HF # 3 provided the best overall death for both planktonic and sessile tests, as shown in Figure 3. N-HF # 2 contained 45% by weight of Clean N Cor and N-HF # 3 contained 40% by weight of Clean N Cor.c
[00269] Additional formulations were prepared with an emulsion breaker to improve oil / water separation using synergistic biocide formulations. For this test, synthetic and raw brine from the field were added to a 250 mL flask. After the addition of the designated chemistry, the flask was mixed for 30 seconds at 2,000 rpm. Once the mixing was completed, the height of each layer was recorded after 5, 20 and 60 minutes.
[00270] Figure 4 shows the white or negative control, against the synergistic biocidal formulation without the emulsion breaker and the synergistic biocidal formulation with the emulsion breaker in concentrations of 100 ppm, 500 ppm and 1,000 ppm, after 20 minutes. Observations revealed that the crude emulsion appears to be tighter with the formulation that includes the emulsion breaker than the formulation without the emulsion breaker. This provides an additional benefit to biocide formulations.
[00271] After determining the reason that produces the most synergistic effects and the addition of the emulsion breaker, an exemplary biocide formulation, according to table 2 was prepared. A sessile death study was conducted to determine the effectiveness of the formulation in Table 2. This test revealed a 98.6% reduction in the planktonic community and a 95.2% reduction in the sessile community after a contact time of 4 hours . Table 2
Example 6
[00272] A study was conducted to estimate the corrosivity of the biocide and two other commonly used biocide products. In this evaluation, the corrosion rates of carbon steel Cio 18 in brine saturated with CO2 at 100% water were monitored in the presence of various biocides in concentrations up to 5,000 ppm, using the wheel box corrosion test at 80 ° C . The results for the three types of biocide, V08, 75% THPS and 50% glutaraldehyde, are provided in figure 5 (A to C). All samples were run in triplicate. The corrosion rate of white or baseline in the 24-hour wheelbox test provided an average corrosion rate of 58.60 mpy (penetration in mils per year), whereas biocides 75% THPS and 50% of glutaraldehyde resulted in corrosion rates of 53.78 and 30.07 mpy, respectively. Similar trends emerged for THPS and glutaraldehyde as the concentration of each increased. However, V08 produced a corrosion rate of 5.14 mpy at 100 ppm. The data indicated that the V08 concentration is inversely proportional to the corrosion rate. The V08 product included water, 2-ethylhexanol, isopropyl alcohol, Nalco Clean N Cor, THPS and acrylic acid, polymer with t-butylphenol, formaldehyde, maleic anhydride, propylene oxide and ethylene oxide (CAS number: 178603-70-8). Overall, the data revealed that V08 can provide protection against corrosion.
[00273] Any ranges given, both in absolute terms and in approximate terms, must encompass both, and any definitions used here are intended for clarification and not limitation. Despite the fact that the numerical ranges and parameters that present the broad scope of the invention are approximations, the numerical values presented in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective test measurements. In addition, all ranges described herein must include any and all sub-ranges (including all fractional and total values) included in them.
[00274] Furthermore, the invention encompasses any and all possible combinations of the same or all of the various modalities described herein. Any and all patents, patent applications, scientific papers and other references cited in this patent application, as well as any references cited herein, are hereby incorporated by reference in full.

权利要求:
Claims (3)
[0001]
1. Biocide composition, characterized by the fact that it comprises: an imidazoline compound; a quaternary amine; and a phosphonium compound in which the imidazoline compound has the formula (I),
[0002]
2. Composition according to claim 1, characterized by the fact that it comprises a demulsifier, in which the demulsifier is selected from the group consisting of dodecylbenzylsulfonic acid (DDBSA), the sodium salt of xylenesulfonic acid (NAXSA), epoxylated compounds and propoxylates, surfactants and anionic, cationic and non-ionic resins, phenolic resins and epoxies and combinations thereof.
[0003]
3. Method of controlling the proliferation of microbes in a system used in the production, transportation, storage and separation of crude oil and natural gas, characterized by the fact that the method comprises putting the system in contact with an effective amount of a composition as defined in claim 1

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法律状态:
2018-02-27| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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2019-05-21| B06T| Formal requirements before examination [chapter 6.20 patent gazette]|

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2020-06-23| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-08-18| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 31/07/2014, OBSERVADAS AS CONDICOES LEGAIS. |

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2020-09-01| B16C| Correction of notification of the grant [chapter 16.3 patent gazette]|Free format text: REF. RPI 2589 DE 18/08/2020 QUANTO AO ENDERECO. |

优先权:

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申请号 | 申请日 | 专利标题

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US201361861803P| true| 2013-08-02|2013-08-02|

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US61/861,803|2013-08-02|

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PCT/US2014/049243|WO2015017705A1|2013-08-02|2014-07-31|Biocide compositions|

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