• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention is useful as a surfactant per se, and can be used for any use where a corresponding pure surfactant is used, and in which the estrogenity is reduced or does not show estrogenity in the compound itself and its degradation products. 1-4 -D- (OC 2 H 4 ) x- (O-Alk) y- (OC 2 H 4 ) z -OR (wherein A is a straight or branched chain alkyl of 1 to 18 carbon atoms) Or alkenyl group, phenyl group, phenyl alkenyl group having 1 to 4 carbon atoms of alkenyl component, polycyclic group having 8 to 14 carbon atoms, polyol, alkoxy group or hydrogen; D is phenoxy, oxy, phenyl, Linear or branched alkyl or alkenyl groups, amino groups or carboxy groups; x is 0-10, y is 1-10; z is 0-100; each (O-Alk) is a straight or branched chain propoxy, butoxy Or substituted oxiranes; and R is hydrogen, sulfate, sulfonate, Mono and / or disulfosuccinate or salts thereof).
    公开号:KR19990036176A
    申请号:KR1019980700844
    申请日:1996-08-02
    公开日:1999-05-25
    发明作者:엠. 와인 메도우즈；크리스티 베르거；폴 베르거；로드니 크래비；찰스 데이비스；킴 프리럭스；찰스 그린；잉 다우-루；지아오 귀옌
    申请人:에드거 제이. 스미스 2세；위트코 코포레이션；
    IPC主号:
    专利说明:

    Alkoxylated compounds and their products having reduced estrogenity.
    The present invention relates to phenolic compounds such as branched and linear alcoholphenols, naphthol and naphthol derivatives, bisphenols, branched and linear dialkyl phenols, benzenediol, benzenetriols, phenol resins, stilbenes and derivatives thereof and phenyl phenols. It relates to alkoxylates and to, but not limited to, alkoxylates comprising the same. The invention also relates to alkoxylates of alcohols, polyols, fatty acids, amines, carboxylic acids and other alkoxylatable materials and more specifically to various industrially applied surfactants and industries, for example. And some alkoxylate derivatives useful as intermediates that can be prepared from other related compounds having various uses in the industry.
    Alkylphenol alkoxylates, especially alkylphenol ethoxylates, have been used extensively in many applications. Such use is generally due to the surfactant properties of these compounds. Conversely, this surfactant property can be adjusted by the appropriate choice of alkyl substituents on the phenyl group and the number of repeating ethoxy units that form the poly (ethoxy) chain attached to the oxygen atom bonded to the phenyl group. . Nonyl phenol ethoxylates, for example, are well known as surfactants with a wide range of uses. Such compounds are generally known as "nonoxynol" compounds and contain 1 to 100 (optionally more) repeating ethoxy units in the molecular structure. Alkylphenol alkoxylates are used in a variety of industrial sectors such as cosmetics, toiletries, oil silk dispersants, deinking surfactants, metal treatments, fiber treatments, emulsion formations, emulsion polymerizations, detergents and related cleaning agents. It has been widely used.
    Recently, the fact that a number of phenolic derivatives, including nonylphenol and nonylphenol ethoxylate, exhibit estrogenity has attracted interest among scientists (Jobling, S. et al., "Detergent Components in Sewage Effluent Are Weakly Oestrogenic to Fish: An In-vitro Study Using Rainbow Trout (Oncorhynchus mykiss) Hepatocytes, "Aquatic Toxicology, Vol. 27 (1993), pp. 361-372; Soto, AM et al.," P-Nonyl-Phenol: An Estrogenic Xenobiotic Released from "Modified Polystyrene" Env. Health Perspectives, Vol. 92 (1991), pp. 167-173.An undesirable side effect of many phenolic compounds, their derivatives, and their biodegradation products. The possibility of being associated with is of interest to all manufacturers and users of these materials.Today, many of the ethoxylates and derivatives thereof that have been proven to be estrogenous, various nonionics, Ionic, cationic and amphoteric surfactants should be treated as carefully as a potential source of these substances in the environment and responsibility behavior.
    Thus, it is possible to identify substances that have a variety of useful properties exhibited by the alkoxylated materials currently in use, but which are capable of synthesizing end objects that do not produce estrogens upon biodegradation and which do not risk estrogens when used. It is desirable to.
    Potential estrogens in terms of widespread and widespread use of alkylphenol ethoxylates, in connection with the possibility that ethoxylates can be degraded, in particular biodegraded, to corresponding alkyl phenol compounds or derivatives thereof that exhibit estrogenity. It is natural that the search for acceptable alternatives proving that it is not a precursor of an active substance has led the field of alkyl phenol alkoxylates.
    Brief summary of the invention
    Despite the fairly reasonable expectation that the alkoxylated homologues of alkyl phenol alkoxylates will decompose into estrogenic alkyl phenols and derivatives thereof, these compounds may contain hydrophobic and hydrophilic components that are polyethoxy components such as alkyl phenol alkoxylates. 3) a short block of propoxy and / or butoxy units extend from the hydrophobic component and present before the ethoxy chain, or 2) propoxy and / or butoxy units are inserted into the ethoxy chain, or 3) Propoxy and / or butoxy units are optionally inserted into the ethoxy chain or 4) propoxy and / or butoxy units are added to the ethoxy chain ends or 5) propoxy and / or butoxy units are ethoxy chains It is characterized in that the substitution instead, these compounds themselves and their degradation products are estrogen sensitive Or estrogenic were confirmed to exhibit a very desirable property does not appear at all.
    Thus, one aspect of the invention consists of compounds of the general formula
    A 1-4 -D- (OC 2 H 4 ) x- (O-Alk) y- (OC 2 H 4 ) z -OR (1)
    Wherein A is a C1-18 straight or branched alkyl or alkenyl group, a phenyl group, a phenyl alkenyl group having 1 to 4 carbon atoms of an alkenyl component, a C8 to C14 polycyclic group, polyol, alkoxy Group or hydrogen; D is a phenoxy, oxy, phenyl, linear or branched alkyl or alkenyl group, amino group or carboxy group; x is 0-10, y is 1-10; z is 0-100; Each (O-Alk) is a straight or branched chain propoxy, butoxy or substituted oxirane; And R represents hydrogen, sulfate, sulfonate, mono and / or disulfosuccinate or a salt thereof.
    Another aspect of the present invention is a compound of formula AD- (O-Alk) y -OH, wherein A, D, (O-Alk) and y are as defined above, and a compound of formula (1) Their use as starting material in the synthesis of
    Products and methods having the above formulas as defined herein have all the desired utility as surfactants, while these compounds themselves and their degradation products are highly reduced in estrogen properties or exhibit no estrogen properties. Characterized by the formation of alkoxylated compounds exhibiting desirable properties.
    Compounds according to formula (1) A 1-4 -D- (OC 2 H 4 ) x- (O-Alk) y- (OC 2 H 4 ) z -OR are useful in many commercial applications, including surfactants Do. Thus, the present invention can be extended not only to such compounds per se, but also to many end-use formulations that may contain one or more compounds of the above formula. Such formulations include, but are not limited to, oil field emulsifiers and demulsifiers, oil silk dispersants, deinking surfactants, metal treated surfactants, textile treated surfactants. , Paper debonding compositions, emulsion polymerization surfactants, surfactants for cosmetics, toiletries and other personal transformations, solid surface cleaning formulations, low-foaming cleaning formulations, emulsifiers and dispersants, wetting agents, agricultural emulsifiers, paint surfactants and Emulsifiers are included.
    Returning to the compound of formula (1) above, component A 1-4 -D- more generally represents the hydrophobic component of the compound in which D is substituted with 1 to 4 groups represented by A. Thus, A 1-4 -D- represents a wide range of possible structures. For example, A may be straight or branched chain alkyl or alkenyl having 1 to 18 carbon atoms such as methyl, preferably straight chain or branched chain alkyl or alkenyl having 4 to 10 carbon atoms such as nonyl; Phenyl; Phenyl-alkenyl, for example benzyl, having 1 to 4 carbon atoms in alkenyl; Fully saturated, fully unsaturated, or partially saturated, such as indanyl, naphthalene, dihydronaphthalene, tetrahydronaphthalene and their homologues containing cyclohexyl, cyclohexenyl, cyclopentyl or cyclopentenyl instead of phenyl ring And partially unsaturated polycyclic groups having 8 to 14 carbon atoms; Hydroxyl or polyol, preferably hydroxyl or polyol containing 2 to 6 carbons and 2 to 6 hydroxyl groups; Or alkoxy, preferably straight or branched alkoxy containing 1 to 20 carbons.
    For example, D can be phenoxy, oxy (ie -O-), phenyl, straight or branched chain alkyl or alkenyl, amino group or carbonyl (ie -C (O)-) having 1 to 18 carbon atoms have.
    Preferred A 1-4 -D-groups include residues from hydroxy benzylphenyl, ie bisphenol A. Other preferred embodiments of the molecules so indicated may be phenyl rings substituted with one, two or three straight or branched chain alkyl and / or alkenyl groups of 1 to 18 carbon atoms or other groups described in the present specification. Preferably A may be 4 to 12 carbon atoms.
    Of course, the present invention also includes two compositions, such as compositions containing one or more structural isomers of compounds having a certain number of carbon atoms, as well as compositions containing compounds corresponding to two or more different versions of formula (1). It can be extended to the above compound of different general formula (1). Compounds of formula (1) also contain 1 to 10 chains of alkoxy units wherein each (O-Alk) is represented by a formula (O-Alk) representing a straight or branched propyl, butyl, or substituted oxirane component. It also contains. Although segments containing short blocks of poly (propoxy) and / or poly (butoxy) moieties or any sequence of propoxy and / or butoxy groups are within the scope of the present invention, It is preferable that each (O-Alk) unit is the same in the predetermined molecule | numerator corresponding to General formula (1).
    In formula (1), the chain consisting of repeating (O-Alk) units can be terminated with 1-100 segments of ethoxy units which are themselves optionally substituted. In the case of nonyl phenol ethoxylates, commonly known as "nonoxynol", the desired degree of solubility and the desired HLB (hydrophilic-lipophilic balance (Griffin, WC, J. Soc. Cosmetic Chmists, To provide vol. 1 (1949), p. 311, the number of repeating ethoxy units can be selected in combination with the number of carbon atoms in segment A. Blocks and propoxy and / or butoxy of ethoxy Any mixture of units may also fall within the scope of the present invention.
    As indicated in formula (1), the poly (ethoxy) capped alkyl phenol alkoxylates can simply be capped with the -H group, thereby providing a useful nonionic surfactant. Alternatively, compounds of formula (1) may be capped with sulfates, sulfonates, carboxylates, phosphate groups or sulfosuccinates and salts thereof, thereby forming a useful series of anionic surfactants. have.
    The anionic group can be balanced in charge by cations M such as sodium, potassium, lithium, ammonium or amine salts remaining in the acid form or in other forms. Certain choices of nonionic and anionic surfactants are within the capabilities of the formulator. Nonionic surfactants and anionic surfactants according to formula (1) include those known for alkyl phenol ethoxylates as well as alkyl phenol ethoxylate carboxylates, sulfates, sulfonates, phosphates and sulfosuccinates. It has a wide range of uses which can all be used for.
    An important aspect of the present invention is that the applicant has found a way to synthesize alkyl phenol alkoxylates of general formula (1), which themselves or their degradation products have reduced or no estrogenity. .
    As mentioned, the synthesis method involves the inclusion of propoxy and / or butoxy units into poly (ethoxy) segments. Of course, it can be appreciated that there are several different synthetic routes in which the desired insertion can be performed. For example, in one preferred embodiment, a precursor of the general formula AD- (O-Alk) y-OH, wherein A, D, (O-Alk) and y are as defined above, is prepared. And then ethoxylated to the desired degree, followed by further reaction of the alkoxylate to provide the desired sulfate, carboxylate, sulfonate, phosphate or sulfosuccinate. In another preferred embodiment, the starting material AD-OH is reacted with a segment H (OAlk) y (OC2H4) zOH already formed or with H (OAlk) y OH followed by H (OC 2 H 4 ) z OH To form a final product.
    In this aspect, it will be apparent to those skilled in the art that the result is a synthetic method that indicates the successful production of surfactant compounds that exhibit significantly reduced estrogen properties or no estrogen properties in the compounds themselves and their degradation products.
    The synthesis of certain preferred compounds according to formula (1) uses conventional synthetic techniques that are quite non-circumventive and are adopted from known methods to form alkoxylates. The choice of raw materials and appropriate reaction conditions of the precursor material can be readily determined by one skilled in the art. As shown, in general, alkylphenols of the preferred composition, preferably positionally substituted, are alkoxylated in such a way as to include propoxy and / or butoxy units into the ethoxy chain to produce a product having the desired properties. The alkoxylate is then recovered or, if desired, further processed to produce sulfonates, phosphates, sulfates, sulfosuccinates or carboxylates according to known techniques. In general, it is preferable to use stoichiometric excess of propylene oxide and / or butylene oxide to ensure that the alkyl phenol is fully alkoxylated.
    The invention will be illustrated by the following examples which are intended to illustrate the invention and not to limit the scope of the invention.
    Example 1
    (p-nonylphenol + 2 EO)
    2.558 g of nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 1.026 kg of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. Stimulation testing of vitellogenin gene expression in trout hepatocytes as well as standard test methods recognized in the art (see Jobling et al., "Detergent Components in Sewage Effluent ..." (see above)) and White , R. et al., "Environmentally Persistent Alkylphenolic Compounds Are Estrogenic," Endocrinology, Vol. 135, No. 1, pp.175-182) demonstrated that this material is estrogenous.
    Example 2
    (p-nonylphenol + 4 EO)
    1.989 kg of p-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 1.595 kg of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. Although high concentrations are required to elicit the same estrogen effect as the material of Example 1, the material proved to be estrogenous from the results of the standard test method described above.
    Example 3
    (p-nonylphenol + 2 PO)
    2.345 kg of nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated for two hours at this temperature and 1.239 kg of propylene oxide (PO) was added to the reactor and allowed to react at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. The standard test method described above was used to demonstrate that this product, nonylphenolpropoxylate, was non-estrogenic.
    Example 4
    (p-nonylphenol + 2 PO + 4 EO)
    2.345 kg of nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 812.5 g of propylene oxide was added to the reactor and reacted at 125 ° C. for one hour. After the propylene oxide was fully reacted, the reactor was vented and 1.233 kg of ethylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor. The estrogenity of this product, nonylphenolpropoxylate, was tested using the standard test method described above and found not to be estrogenic. Degradation studies have also demonstrated that this substance does not degrade to estrogenically active substances.
    Example 5
    (p-octylphenol + 4 EO)
    1.932 kg of octylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 1.652 kg of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. The results from the standard test method described above indicate that this material is estrogenous.
    Example 6
    (p-octylphenol + 2 PO + 4 EO)
    1.481 kg of octylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 836 g of propylene oxide was added to the reactor and reacted at 125 ° C. for one hour. After the propylene oxide was fully reacted, the reactor was vented and 1.266 kg of ethylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor. The results of the standard test method described above indicate that this material is in fact less estrogenic than the ethoxylated control.
    Example 7
    (o-nonylphenol + 4 EO)
    1.989 kg of o-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor and then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 1.5959 kg of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. From the results of the standard test method described above, this material proved to be estrogenous.
    Example 8
    (2-methyl, 4-nonylphenol + 4 EO)
    2.043 kg of 2-methyl, 4-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 1.5409 kg of ethylene oxide (EO) was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. From the results of the standard test method described above, this material proved to be estrogenous.
    Examples 9-12 additionally describe the synthesis of compounds with reduced estrogenity and reduced tendency to degrade to estrogenous products.
    Example 9
    (2-methyl, 4-nonylphenol + 2 PO + 4 EO)
    1.592 kg of 2-methyl, 4-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 790.9 g of propylene oxide was added to the reactor and reacted at 125 ° C. for one hour. After the propylene oxide was fully reacted, the reactor was vented and 1.201 kg of ethylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor.
    Example 10
    (p-nonylphenol + 1 EO + 2 PO)
    2.073 kg p-nonylphenol and 10.8 g sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 416 g of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. After the ethylene oxide was completely reacted, the reactor was vented and 1.201 kg of propylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor.
    Example 11
    (p-nonylphenol + 1 EO + 2 PO + 3EO)
    1.538 kg of p-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 308 g of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. After the ethylene oxide was completely reacted, the reactor was vented and 812 g of propylene oxide was added to the reactor and allowed to react for one hour. After the propylene oxide was fully reacted, the reactor was vented and 925 g of ethylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor.
    Example 12
    (p-nonylphenol + 2 PO / 4 EO)
    2.345 kg of nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 812.5 g of propylene oxide and 1.233 kg of ethylene oxide were added to the reactor as "mixed" oxide and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor.
    Examples 13 and 14 were carried out to allow comparative evaluation of the estrogenity of the materials produced.
    Example 13
    (p-nonylphenol + 2 PO + 10 EO)
    1.193 kg of p-nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 2.391 kg of ethylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor.
    Example 14
    (p-nonylphenol + 2 PO + 10 EO)
    1.104 kg of nonylphenol and 10.8 g of sodium hydroxide 50% aqueous solution were placed in a reactor, then purged and heated to 125 ° C. The mixture was dehydrated at this temperature for two hours and 536 g of propylene oxide was added to the reactor and reacted at 125 ° C. for one hour. The resulting mixture was neutralized and removed from the reactor. After the propylene oxide was completely reacted, the reactor was vented and 2.034 kg of ethylene oxide was added to the reactor and allowed to react for one hour. The resulting mixture was neutralized and removed from the reactor. Degradation studies comparing to Mulnil prepared in Examples 13 and 14 showed that the methods described for preparing the aforementioned materials also reduced the estrogenity of their degradation products.
    Evaluation of the functional and physical properties of nonoxynol-4 and its non-estrogenic counterparts indicates that modifications made to produce non-estrogen homologs do not adversely affect functional properties such as the surfactant properties of the foreign materials. .
    权利要求:
    Claims (11)
    [1" claim-type="Currently amended] Compounds of the general formula (1) below wherein the estrogenity of the compound itself and its degradation products is reduced or does not show estrogenity as compared to homologues where y is zero.
    A 1-4 -D- (OC 2 H 4 ) x- (O-Alk) y- (OC 2 H 4 ) z -OR (1)
    Wherein A is a C1-18 straight or branched alkyl or alkenyl group, a phenyl group, a phenyl alkenyl group having 1 to 4 carbon atoms of an alkenyl component, a polycyclic group having 8 to 14 carbon atoms, a polyol, a carbon number 1 to 20 alkoxy groups or hydrogen; D is phenoxy, oxy, phenyl, linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, amino group or carboxy group; x is 0-10; y is 1-10; z is 0-100; Each (O-Alk) is a straight or branched chain propoxy, butoxy or substituted oxirane; And R represents hydrogen, sulfate, sulfonate, mono sulfosuccinate, disulfosuccinate or hydrogen, ammonium, or alkali metal cation salts thereof.
    [2" claim-type="Currently amended] The compound of claim 1, wherein A is a straight or branched chain alkyl or alkenyl group having 1 to 18 carbon atoms and D is phenyl.
    [3" claim-type="Currently amended] The compound of claim 1, wherein x is zero.
    [4" claim-type="Currently amended] 4. A compound according to claim 3, wherein A is a straight or branched chain alkyl or alkenyl group having 1 to 18 carbon atoms and D is phenyl.
    [5" claim-type="Currently amended] The compound of claim 4, wherein A is nonyl.
    [6" claim-type="Currently amended] In an improved method for synthesizing compounds having a hydrophobic component and a hydrophilic component and the hydrophilic component consists of a polyethoxy component, between the hydrophobic and hydrophilic components, y is 1 to 10 and each y Alk unit is propyl or butyl. An improved synthesis method wherein the inclusion of a segment of formula (O-Alk) y reduces the tendency to biodegrade into estrogen and estrogen by-products of the compound.
    [7" claim-type="Currently amended] The method according to claim 6, wherein the compound is a compound of the following general formula (1).
    A 1-4 -D- (OC 2 H 4 ) x- (O-Alk) y- (OC 2 H 4 ) z -OR (1)
    Wherein A is a C1-18 straight or branched alkyl or alkenyl group, a phenyl group, a phenyl alkenyl group having 1 to 4 carbon atoms of an alkenyl component, a polycyclic group having 8 to 14 carbon atoms, a polyol, a carbon number 1 to 20 alkoxy groups or hydrogen; D is phenoxy, oxy, phenyl, linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, amino group or carboxy group; x is 0-10; y is 1-10; z is 0-100; Each (O-Alk) is a straight or branched chain propoxy, butoxy or substituted oxirane; And R represents hydrogen, sulfate, sulfonate, mono sulfosuccinate, disulfosuccinate or hydrogen, ammonium or alkali metal salts thereof.
    [8" claim-type="Currently amended] 8. An alkyl phenol compound of the general formula AC 6 H 4 -OH, wherein A is a straight alkyl group of 1 to 18 carbon atoms, comprising at least one compound selected from the group consisting of propylene oxide, butylene oxide and substituted oxides; Reactions to produce intermediates of the general formula AC 6 H 4- (O-Alk) y OH, wherein y is 1 to 10 and each y Alk unit is propyl or butyl, and the intermediate is reacted with ethylene oxide so that z is 1 to 100 To form the product of phosphorus AC 6 H 4- (O-Alk) y- (OC 2 H 4 ) z OH.
    [9" claim-type="Currently amended] The method of claim 8, wherein A is nonyl.
    [10" claim-type="Currently amended] 8. An alkyl phenol compound of the general formula AC 6 H 4 -OH, wherein A is a C1-C18 straight chain alkyl group, is a compound of formula H- (O-Alk) wherein y is 1-10 and z is 1-100. ) y - (OC 2 H 4 ) z OH react with the compound by the formula AC 6 H 4 - a method of forming a (OC 2 H 4) z OH - (O-Alk) y.
    [11" claim-type="Currently amended] The method of claim 10, wherein A is nonyl.
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    同族专利:
    公开号 | 公开日
    WO1997006125A1|1997-02-20|
    MX9800979A|1998-04-30|
    CZ28898A3|1998-07-15|
    TW340110B|1998-09-11|
    BR9610073A|1999-03-02|
    NO980462L|1998-03-24|
    EP0848694A1|1998-06-24|
    AR003190A1|1998-07-08|
    CN1197449A|1998-10-28|
    EP0848694A4|1999-08-25|
    NO980462D0|1998-02-03|
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    CA2228133A1|1997-02-20|
    JPH11510189A|1999-09-07|
    ZA9606604B|1997-02-18|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    1995-08-04|Priority to US51113095A
    1995-08-04|Priority to US8/511130
    1996-08-02|Application filed by 에드거 제이. 스미스 2세, 위트코 코포레이션
    1999-05-25|Publication of KR19990036176A
    优先权:
    申请号 | 申请日 | 专利标题
    US51113095A| true| 1995-08-04|1995-08-04|
    US8/511130|1995-08-04|
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