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    • 专利摘要:
    Polymeric quaternary ammonium salts are provided in which the cationic units correspond to the formula in which R1, R2, R3 and R4 are identical or different from one another and denote optionally substituted alkyl, cycloalkyl or alkenyl with at most 20 carbon atoms, aryl or aralkyl, or (R1 and R2) and/or (R3 and R4), together with the nitrogen atom to which they are bonded, form an optionally substituted heterocyclic ring with 3 to 6 ring members, A1 is -(CH2)m-, in which m is a number from 1 to 20, which is optionally interrupted by at least one -S-, or -CH=CH- grouping or substituted by at least one hydroxyl, halogen, nitrile, alkyl, hydroxyalkyl, alkoxy, carboxyl or carbalkoxy or optionally by at least one substituted aryl or aralkyl radical; polyoxyalkylene;an aryl,aralkyl or cycloalkyl radical; or A1 forms together with the nitrogen atoms and at least one of the subst??uents bonded to each nitrogen atom a piperazine, 1,4-diaralicyclo-(2,2,2)-octane or dipyridyl grouping, and A2 is a diphenylene or a tetrahydronaphtha ?e radical. The new compounds can be used as dyeing and finishing agents, especially for dyeing textile materials, as dispersing agents and emulsifiers, as antistatic, antimicrobial and flocculating agents and as precipitants.
    公开号:SU890981A3
    申请号:SU762430502
    申请日:1976-12-23
    公开日:1981-12-15
    发明作者:Хорн Ульрих；Берендт Ханс-Ульрих；Лихти Петер；Вегмюллер Ханс
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    where R., Rrt, Rq 4 are the same or different and mean methyl; alkyl (C (, substituted by hydroxyl, alkenyl (Cij), benzyl or R / j and / or RnH R together with the nitrogen atom to which they are bound, form a 6-membered heterocyclic ring; A is radical- (CH | j) (m 1-12), which may be interrupted by the group —O— or, or may be substituted by hydroxyl or methyl, the group
    - (in- ut2 - o - Neeles Sn, SNs
    (L1r) „, 1 where B is a simple bond, -0-, methylene, p 1,2 or A together with nitrogen atoms means the residue of the formula

    -HN NHr -ir N-,
    h-w
    -one/
    where R (3 is equal to R and denotes the radical -CHO COOCHO or -CHQCOOCrj Hj, and a compound of the formula
     ,
    where X is halogen; and Yas-represents
    -eng SNGS1Ng,
    -eNg-C-CHg0
    -NgS1
    As a result of the process, polymers of the formula
    .e

    KAL BC
    where .RrtR, A and R - have the indicated values.
    All the usual inorganic or organic anions that do not form any sparingly soluble complexes with cations are suitable as anions for the proposed polymeric quaternary ammonium salts, since ammonium salts should preferably be soluble in water. Anions of mineral acids or low-molecular organic acids should be mentioned. Suitable, for example, are halogen anions, such as 1, Br, and especially CP or methyl sulfate (CHnSO), ethyl sulfate
     (СЛНе504) and toluene sulfonate or nitrate and sulfate.
    The resulting polymeric quaternary ammonium salts can have molecular weights (weights) of 400-50000,
     preferably 25,000.
    The preparation of ammonium salts can be carried out by known methods, for example, by reacting the diamines with the corresponding dihalide compounds in molar ratios of 1: 2-2: 1, preferably in equimolar amounts. The preparation of ammonium salts can be carried out in inert with respect to the components.
    5 solvent reactions, for example
    alcohols, glycols, ketones, such as acetone, or cyclic ethers, dioxane or tetrahydrofuran. From alcohols
    lower alcohols are preferred, especially methanol. At Boi6ope, the reaction temperatures are usually governed by the boiling points of the solvents used, which may be 20ISO C, preferably ZO-SUO C. Synthesis can also be carried out in water or water-alcohol mixtures, with or without solvent,
    When using cheap and readily available dichloro-containing compounds in the preparation of polymeric quaternary ammonium salts, the latter contain chlorine ions as anions. The introduction of other anions can be effected, for example, by ion exchange. The resulting polymeric quaternary ammonium salts precipitate upon receipt, as a rule, in the form of mixtures, and not in the form of pure compounds.
    The resulting polymeric quaternary ammonium salts can be used in finishing baths, which can be neutral, acidic or alkaline. They are useful as dyeing aids, especially as leveling agents, in dyeing and printing methods for textile materials made from natural or synthetic fibers. As natural fiber textiles materials are used from cellulosic fibers, especially cotton, wool and silk, textile materials from synthetic fibers are, for example, materials from high molecular weight polyesters, for example polyethylene terephthalate or polycyclohexanedimethyl terephthalate; polyamides (based on hexamethylenediamine, poly-E-Capralactam or ii-aminoundecanoic acid); polyolefins or polyacrylonitriles, from polyurethanes, poly vinyl chlorides, polyvinyl acetates, and also from cellulose diacetate and cellulose triacetate. These synthetic fibers can also be used as mixtures with each other or in a mixture with natural fibers, for example cellulose fibers or wool. These fibrous materials can be in all suitable for the continuous way of working conditions, such as, for example, in the form of a cable, combed batt, yarn, yarn, fabric, knitwear or non-woven products.
    909816
    Dye compositions can be in the form of aqueous or aqueous organic solutions or dispersions or in the form of printing pastes, which, in addition to dye and polymeric quaternary ammonium salts prepared according to the invention, also contain other additives, for example acids, salts, urea and other auxiliary substances.
    agents, for example, oxyalkylation products of fatty amines, fatty alcohols, alkylphenols, fatty acids and fatty acid amides.
    Polymeric quaternary ammonium salts are particularly suitable as moderators in dyeing polyacrylonitrile fibrous materials with cationic dyes and also in dyeing with anion-modified polyester fibrous materials. Cationic dyes that are used can belong to the most diverse groups. Suitable colors are, for example,
    25 diphenylmethane, triphenylmethane, rhodamine dyes and azo- and / or anthraquinone dyes containing onium groups, triazine, oxyazine, methine and azomethine dyes,
    thirty
    Dyeing of polyacrylonitrile fibrous materials can be carried out in the usual way, for this the material to be painted is introduced into an aqueous bath heated to about 50-60 ° C, which contains a cationic dye, a polymeric quaternary ammonium salt, salts like sodium acetate and sodium sulfate, as well as
    acids, such as acetic acid or formic acid, then the temperature of the dyebath rises to about 100 ° C for about 30 minutes and then the dyebath is kept at this temperature until it is depleted. However, it is also possible, first, to add a basic dye in addition to the dyebath, for example, when the bath temperature rises to about 60 ° C. The material to be painted can also be pretreated at 0-100 ° C with a bath that contains common salts and acids, as well as a polymeric ammonium salt, but does not contain any dye, then just add the colorant and dyeing is carried out at 100 ° C. Finally, it is also possible to inject the material to be dyed directly into the dyebath that is heated to about the dye bath, which contains the ammonium polymer salt. Under polyacrylonitrile fibrous materials, you need to understand such materials, for the manufacture of which other vinyl compounds are also used, other vinyl compounds, for example, vinyl chloride, vinyl acetate, vinyldene dane, in addition, also used vinyl. and alkyl esters of acrylic acid, and the proportion of these vinyl compounds is not. more than 20 in relation to the weight of the materials. the amounts of polymeric quaternary ammonium salts which are used according to this dyeing method are in total 0.01-2% by weight, in particular 0.05-1 or 0.1-1% by weight, relative to the weight of the fibrous materials. ammonium salts as colorants, polyacrylonitrile fibers have a very good evenness of color and are simultaneously observed. Good yield of dye on the fiber. Other uses of the resulting polymeric quaternary ammonium salts are reserving agents for dyeing polyacrylonitrile fibers; dispersants, for example for pigments; emulsifiers; cationic fixatives to improve the wet handling properties of cellulosic textile fibrous materials or paper dyed with direct and dispersed dyes; antistatic
    Ciha
    I
    Si g
    -Tsr -
    to,
    Viscosity 0, DL / g (25 ° C, methanol). The average molecular weight (mass) is 7900 ..
    The viscosity in this and the following examples is the reduced viscosity. Measured values refer to 0, (g / vol) solutions in methanol. Average molecular weights are determined based on these viscosities.
    Example 16, In the second preparation with the same ingredients.
    2Cil
    SN.-
    reactions receive the reaction product with a viscosity vj of 0.52 dl / l. (, methanol) and with an average molecular weight of 7600i
    Example 1c, In the preparation with the same components of the reaction (molar ratio of diamine to halide 2: 1), the reaction product is obtained, it reacts with a viscosity i 0.10 dl / l (25-С, methanol) and with an average a molecular weight of 1500, which means, especially for textiles containing synthetic organic fibers; antimicrobial agents; precipitating agents, for example, in wastewater treatment, or flocculating agents, for example, dye dispersions. Polymeric quaternary ammonium salts in particular are used in dyeing and printing methods containing natural or synthetic fibers of textile materials, for example, when dyeing polyacrylonitrile fibers; fixing dyes; finishes, in particular. to impart antistatic properties to textile materials containing synthetic organic fibers; wastewater treatment plants, where they can be used as precipitants, as well as in a method of coagulating, for example, colloidal aqueous disleneses as a flocculating agent. Example 1a 109g (0.435 mol) of 4,4-bis- (chloromethyl) -diphenyl and 111 g (0, t35 mol) of N, N, M, M-tetramethyl-1.12-diaminododecane in kkQ ml of methanol is heated for 2k h at boiling point with reflux. Then the solvent is distilled off and the residue is removed. dried at. The product is soluble in water to form a clear solution. Output 220 g (100 from theory) of the product of interaction with repeating units of the formula. By analogous interaction +, 4-bis - (- chlorometi,) - diphenyl with N, N, N, N-tetramethyl-substituted ethylenediamine, 1,3 diaminopropane , 1, -diaminobutane, 1,6-diaminohexa-ZD- () ciH2 - SND
    Table 1 shows the values, viscosity and average molecular weight for examples 1g-1i.
    Example 2, 12.7 g (0.05 mol) of N, N, NJN-tetramethyl-4, -diaminodiffe nilmethane and 11.5 g- (0, mol), C-bis (chloromethyl) -diphenyl in 100 ml of methanol boil under reflux for 2k hours. Then the solvent is distilled off, the residue is treated with 150 ml of ether and stirred, then filtered and dried in vacuo at. A powder is obtained which is soluble in water to form a clear solution.
    The yield is 23.7 g (EV% of theory) of the product of interaction with the repeating units of the formula 81 n., 1, 8-diaminooggan and 1,10-diaminodecane. Also obtained in quantitative yields are products of the interaction with the repeating units of the general form, ly
    Thanol viscosity), with At. Obtained with quantitative yields. product 1 interaction with replay u
     WengSn.
    HH,
     f (Hg) Y @ CiH2- /
    with: nz SNZ "iHa
     VI /
    eNg + gf
    v / t) It is 0.13 dl / l (25 ° C, the average molecular weight of measure D3). Follow the procedure for n- (englie-1 (nd: n: g) enGs3 and -z (CH CH-CH) CH - NICH iVj) of Example 1 and equimolar amounts of 4, -bis- (chloromethyl) -biphenyl with the diamines of the following formulas are introduced into the interaction:
    .Ng
    y
    /
    CKz- r dHffJ
    CiHa Viscosity, dl / g: a. equal to 0.23; b.t - 0.19; at. t - О J2 (25С, methanol). The average molecular weights are respectively equal to a. b. 280 at .1700. Example ta. 88.15 g (0.5 mol) of N, N, N, N-tetramethyldiaminohexane and 125.5 g (0.5 mol) of tj-eHC- (chloromethyl) -diphenyl in 300 ml of methanol boiling water ) СНзСНз The product is soluble in water to form a clear solution. Viscosity t 1.5t DL / g (25 ° C, methanol); average molecular weight 23000, Example 4: 25.12 g (0.1 mol) +, -bis- (chloromethyl) -biphenyl is dissolved in 80 ml of acetone and heated to reflux (5b ° C). While stirring, 17.23 g (0.1 mol) of 1,6-bis- (dimethylamino) hexane, dissolved in 20 ml of acetone, are added over a minute. An exothermic reaction starts and a colorless precipitate starts at the same time. After boiling for k hours at reflux temperature, the reaction ends, the precipitate is filtered and dried. 2.3 g (100% of theory) are obtained under reflux with stirring. To the reaction mixture, which becomes more viscous with an increase in reaction time, 200 ml of methanol are added. After refluxing for 2 hours, the reaction is completed and the solvent is distilled off. 212 g (100% of theory) of the product is obtained by reacting with repeating units of the formula CIS - ecii interacting with repeating units of the formula 5Go. The product is a white, hygroscopic powder that dissolves in water to form a clear solution. Viscosity 0.30 dl / g (, methanol). The average molecular weight of AOO. Example 5ao 12.5b g (0.05 mol) i, 4-6Mc- (chloromethyl) -diphenyl and 13 g (0.1 mol) 1, (dimethylamino) propane with stirring, is heated for 30 hours at the liquid reaction mixture, which is suspended in 50 ml of water and clarified by filtration. The filtrate is evaporated to dryness. 16 g of product are obtained by reacting with repeating units of the formula
     ciH5snz
    -1T (SNg), - - SNg
    CH.J
    CJH,
    Output 62.2% of theory. Viscosity 0.1 dl / g (25 ° C, methanol). The average molecular weight is 2000.
    . Similarly, however, when using a solvent, reaction products are obtained from +, -bis (chloromethyl) diphenyl and the indicated
    in tabLo 2 diamines. The conditions of the reaction, the yield and characteristics of the products are given in table. 2
    EXAMPLE 6 Follow the procedure of Example k and equimolecular amounts, 4-bis13890981, are introduced into the interaction.
    - (chloromethyl) diphenyl and one of the products of the interaction of examples
    diamines. The diamines used in reaction-6g can be represented by the following, the conditions of the reaction, the characteristic structural formulas (product tests are listed in Table 3. 3. links)
    G1 G1
    -ABOUT
    ) V (ciHe) 2 -V (iHe-f VVeH, 2I1
    X //
    ® .., d® Sne L / LCh-SNg doodzH CoodzHs
     A a§ d,
    -N - (FW-FN-CJ nM LnM Lnz
    ® / EngOO V- /
    0
    . zdi
    X // I
    zdr v.
    .0
    zdi
    Xv
    ©
    -OOU-
    0
    2Br
    XVI
    SNGXV
    ONGZdl
    Sh
    SNGO C)
    W- (te, l ,,
    Zbr
    Xx
    (iH.7. Exit 30 from theory. Viscosity, 0.06 dl / g, methanol). Average molecular weight 900 °
    Example 8 “Equimolar amounts of a diamine of the formula
    9 “1am
    pi (cH-sn-of-OH -on-N HU-1
    СНО, с.н „.OHij СНО, ОНз lch | -N - (Sn-s; Ng-o) n C 1 H. - BesNE. Cjhj
    The characteristics of the reaction products are given in Table k.
    Example 9. Equimolar amounts indicated in Table. 5 dichlorides of and p-bis- (dimethylaminomethyl) -biphenyl are heated in acetone for 2 hours at reflux temperature. During the reaction, the reaction product precipitates. At the end of the reaction, C-bis- (chloromethyl} diphenyl is reacted, in methanol, for 2 hours at reflux temperature. After removing the solvent, reaction products are obtained with repeating units of the formula
    geg
    x; (| 1
    the mixture is cooled, the separated product is filtered and dried, the dichlorides used in the reaction and the characteristics of the reaction products are given in tbal. five.
    The products of the interaction of examples 9a-9d can be represented by the following structural formulas (repeating units) CH, I N
    zdi
    XXI //
    ЪCjHj
    N-dHz - V ciHz-N eH2- / / c: ii2 Cn, Bnz
    d.tM.S isomerers as 40:60)
    e
    zdi
    dHe-j CHrTVYeil, BH
    2 (l
    Xxv
     .
    , SNg - bNg
    HH,
    Xxw
    (n.
    ©
    N - CHj- С
    Example 10, Equimolar amounts of a diamine of the formula
    NzONs1Nz
    to-SNG-CK-SNG-i
    ilH
    CHi and
     xxv / i
    ciHj and ", -bis- (chloromethyl) -diphenyl are refluxed (5b ° C) with 1.1 equivalents of sodium iodide
    10 in acetone "8 hours. Then the reaction solution is filtered. The solvent from XYI / l is chased and a colorless reaction product is obtained as a residue with repeating units of the formula
    Nz OH h, L5 J. J F1
    -K - s1Ng - CH-SNg -N - SNg
    - Snthe.
    XXIX
    CH,
    Output 72.7% of theory.
    The iodide can be converted to the corresponding chloride by reacting with freshly precipitated silver chloride (2 hours in methanol at 64 ° C, then filtered, otdH 7 CH2-one
    SNGCN YNS H2 -N
    l
    and C, α-bis- (chloromethyl) diphenyl are boiled in acetone under reflux (5 ° C) h. Upon completion of the reaction, the solvent is distilled off and the residue JH-I - CH 2 CH 2 Exit 7.7 from theory. Viscosity ij 0.1 dl / g (, methanol). The average molecular weight of T + OO. An IR spectrum (KBG) shows absorption bands at 3310, 3050, 29 bO, 2620, 1970, 1925, 1835, 1660, 1615, 1590, 1505, 1 + bO, 1220, 109.0 ,. 1055, 1010, 960, 930, 815. 755, 705 and 665 cm-1
    drive the solvent and dry the remaining product). Viscosity, 0.38 dl / g (25 ° C, methanol). The average molecular weight of filOO.
    Example 11, Equimolar amounts of a diamine of the formula
    CIS-SNG he
    XXX
    C1Hg-C1bH5 is extracted with hot water. From the aqueous solution, after removing water, a colorless reaction product is obtained with repeating units of the formula Zdl XXX /, grimer 12, Equimolar amounts of a dichloro-containing compound of the formula C1 XXXII and 4-bis (dimethylaminomethyl) dif19
    Nile is introduced into the reaction as described in Example 9. Pro890981 is obtained.
    20
    interaction with repeating formulas
    zdi xxxiK
    Yield 23% of theory.
    The product is not sufficiently soluble in methanol, so the viscosities in this solvent could not be determined. IR spectrum (KBG) shows absorption bands at 3 + 70, 3280, 1615, 1565, U65,,, 1120, 1075,, 995, 970, 82, 735, 600, 575, 505, +75 and see
    Example 13 25.5 g (0.1 mol) of 4,4-bis- (chloromethyl) diphenyl and 8.88 g (0.1 mol) of piperazine, together with 11.7 g of sodium carbonate, are dissolved in 200 ml of benzene and heated with stirring for 20 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature. (20-25C), filtered, the residue is washed with tOO ml
    © / -V® J
    -K 1G-sng
    SNGCOOCHN CiHgCOOdH,
    Viscosity 0.17 dl / g (25 ° C, methanol). The average molecular weight is 2500.
    Example C. 50.23 g (o, 2 mol) of 4,4-bis- (chloromethyl) diphenyl and 26.05 g (0.2 mol) of N, N, N, N-TeTpaMetil-1, 3-diaminopropane heated for 2 h in 200 ml of water at 95 ° C. Reactivates and then dried. Obtain O k, J g (55.6 from theory) compounds with repeating units of the formula
    -eng
    -K1
    3.97 g (0.015 mol) of this product, with 13.0 g (0.12 mol) of chloroacetic acid methyl ester, are heated for 15 hours while stirring at 80-90 ° C. Upon completion of the reaction, the reaction mixture is cooled and extracted with 100 ml of water. After evaporation of the aqueous solution, 101 g (H of theory) of the product are obtained, which reacts with the repeating units of the formula
    z (ir
    XXXV
    After cooling the reaction mixture to room temperature (C), the resulting mixture can be further diluted with water, for example 100 ml, and thus can be directly used for various purposes. The resulting reaction product contains
    link formula
    -ГГ- (е11г)
    2Cll XXXVI
    (1NG dry matter content in aqueous solution (after diluting with 100 ml of water), weight:
    Calculated 21.6.
    Found 22.6.
    Chlorine content (titration), weight .:
    Calculated (full quartering) C, 0,
    Found 3.9
    By removing water or precipitating with acetone, the product of the reaction of the formula XXXVI can be obtained as a substance.
    Exit 100 from theory. Viscosity
    ij 0, A2 dl / g (25 ° C, methanol). The average molecular weight is bsOO
    Instead of water, you can use mixtures of water with other solvents as a solvent.
    especially those that are homogeneously mixed with water, for example isopropanol, and thus improve the homogeneity of the reaction mixture. 2189P98 Thus, it is possible to obtain similar products with an average molecular weight of 8800-15200, Example 15. 5 g of polyacrylonitrile tissue (Orlon 42-Dupont) s is treated for 20 minutes at 98 ° C in a dyeing apparatus in a 200 ml bath, which contains 0, 01 g of an auxiliary agent of the formula t (Example 1a) and in which the pH value of k is adjusted with 80 ° C acetic acid, with the tissue constantly moving. A bath consisting of the following dye mixture is then added: 0.007 g of the dye of the formula 5 0.007 g of the dye of the formula P-and-Enz Hz, J N-CHj 0.01 g of the dye of the formula 238 acetic acid establish a pH value of 6. Thus subjected to subsequent processing, the color is significantly improved, as compared with the color that was not subjected to subsequent processing, when testing the resistance of conductors in water (SNV norm 195819 DIN). Subsequent processing (fixation of the dye) can also be carried out using the rest of the interaction products indicated in the examples. Moreover, clear improvements in the color stability are also achieved. Example 19 Fabric (Orlon A2-Dupont) is plus with a bath, which contains 15 g of auxiliary agent in a liter in example 1e, squeeze until weight increases by 110 and dry for 30 minutes at 80 ° C. Then the fabric is fixed for 30 s. After drying, the surface resistance of the fabric is measured. In the second experiment, the measurement is repeated according to le 5 washes. The surface resistance of untreated and treated tissues before and after 5 washes are given in Table 6. Due to the described treatment, using a specified aid, a distinct decrease in the surface resistance is achieved; these effects show good washability (permanent antistatic). The applied adjuvant has virtually no effect on the nature (properties) of the tissue contamination. Similarly, other interaction products can be used in the same way as in Examples 1-14, and the result is also good antistatic effects. Example 20 In the sump of a sewage treatment plant together with industrial waste water, which contains about 100 MoDo (ppm) mixture reactive dyes and acid dyes; an aqueous solution of the product of the reaction is introduced as in Example 1c. The amount of interaction product that is introduced into the wastewater is 60 ppm. Spontaneous (spontaneous) precipitating of the dye occurs. After 30 minutes the precipitated dye can be separated by filtration, and the remaining wastewater (filtrate), completely bleached, can be thrown into the sewer. As a rule, it is not necessary to filter, but it is possible to sediment precipitates. In the present case, the precipitated dye collects at the bottom for about an hour and the completely discolored water above it can be pumped to the sewage system. With an excessive dosage of the precipitant, no dissolution of the precipitates is observed. Instead of the product of the reaction according to Example 1b, the others mentioned in examples 1-1 can also be used. The products of interaction with the same good success. Example 21 about 20 g of polyacrylonitrile fabric (Orlon 42-Dupont) is treated for 60 minutes at 98 ° C in a dyeing apparatus in a 800 ml bath, which contains 0.02 aids in Example 1g, in which the pH value of k is adjusted with acetic acid. Then the bath is cooled and the fabric is rinsed. Pretreated fabric together with the same amount of untreated fabric is dyed as follows: 10 g of pre-treated and 10 g of pre-treated fabric are added to a dyeing apparatus in a 800 ml bath which contains 0.03 g of a dye mixture mixture (1: 1) formulas
    ACI
    and basic red 22 (C.I. 11055) and in which the pH value of k is established with acetic acid, and treated for 60 minutes at After
    55 THIS bath is cooled, the fabric is rinsed as usual and brought to the ready state. The pretreated fabric is well reserved and shows only a weak (light red) color, while not pretreated the fabric shows a dark red color. Similar redundant effects can also be achieved using other products of the interaction of examples 1-1. Example 22 Determination of bactericidal action. The bacterial inhibiting effect of the polymeric quaternary ammonium salts is determined in the suspension experiment. Solutions are prepared in water with a substance content of 1-30 ppm. Approximately 10 microorganisms per ml of suspension are added to B5 ml of the resulting solutions. Testing microorganisms: 1; Staphilococcus aurens SG 5t1 Z / Escherichia coli NCTC 8196 3.Pseudomonas aerug.inosa NCTC 8060
    (CH3) (CH5,) (, N (CH3) .i: 1 h,
    (CH ,,). N (CH,) feN (CHo)) Q f h,
    Table
     H,
    acetone, 56 ° C 100 0.26 3800
    AIIPT
    acetone, 5b ° С 100 0.30 00 After a certain amount of time, 0.1 ml of the mixture is contaminated with a solid nutrient medium that contains a blocking agent (for example, polyoxyethylene sorbitan monooleate). The number of living microorganisms is determined. The test results are shown in Table. 7-9o The interaction products show good antibacterial (antimicrobial) activity against the three test microorganisms. Thus, the polymer compounds prepared according to the invention can be successfully used as auxiliary materials in dyeing textiles and as substances possessing antimicrobial activity blitz 1
    (CHj), N (CH3,), N (CH, i, h.
    (CH3) (CH2) feN (CH). i h
    (CH,.) NN (CHfsUN (CHj. 2Ah,
      - methanol, 63 ° C
    {CH) N (CH) N (CHo), 2 h,
    T1 diamine supplement for 1.5 hours
    s ° l
    1Т- (с1Нг) г HI / ЪЗН / Н 27 h, 1 Г- I / -Ч ТТ - ч V-с- (VN methanol N L V- / L bo ° с 1 / N
    Continued table. 2
    acetone,
    0.26 3300
    acetone, 20 ° С 0.31 tSOO 1, 5 23000 0.11 1600
    methanol
    acetone, v / v „1: 1,,
    Table 3
    0.06 900
    25 27 h, methanol acetone, m, acetonitrile, BZ-UO S, 600, 35 5100, 05 700 DiЬ
    based on elemental analysis, IR spectroscopy and NMR spectrum
     Used C, C-bis- (bromomethyl) -diphenyl,
    The quaternary product is extracted with water from the reaction mixture,
    Used, 4-bis- (iodomethyl) -diphenyl,
    The reaction product was then quaternized with ethyl chloroacetic acid.
     SNg- (1

    about
    SNg- (1 (Jl-CJUz
    Continued table. 3
    Table
    Table 5
    0.36
    5300
    88.3
    300
    9.3
    0.29
    Continued table. five
    2800
    100
    0.10
    (the ratio of 1.4: 1.5 isomers is tO: 60)
    g OYNG SNU-s /
    d di-dHj-d-ciKz-clL
    o Reaction conditions: 2 hours in a dose (20-25 s).
    The test microorganism Staphyloccus aureaus SG 511
    100
    0.22
    3200
    0.07
    1000
    70.5
    Table 7 acetone at room temperatureTable 6
    33
    bg, 5-10 mo “yu-th 0.5-10 th-th o
    8a MO 1.5-10 5-10 2-10 О 9ИО О Test microorganism Escherichia co) i NCTC 8196 Test microorganism Pseudomonas
    8909813
    Continued table. 7
    Table 8 Table 9 aeruginosa NCTC 80bO
    权利要求:
    Claims (1)
    [1]
    Claim
    A method for producing polymer quaternary ammonium salts by reacting tertiary diamines with di- 5 halogen compounds, characterized in that, in order to obtain polymers having high rates when used as auxiliary agents for dyeing, compounds of the formula are used as tertiary diamines
    Ri R a ί ί Ώ 15
    Ν-Α-Ν
    I ®
    R ^ Hell where R ^, Rq_, Rj, R4 are the same or different and mean methyl, alkyl (Cq ~ $),. 20 substituted with hydroxyl, alkenyl (Cq), benzyl, or A ^ and Rq. and / or R 3 and R v together with the nitrogen atom to which they are attached form a 6-membered heterocyclic ring; A - radical 2 5
    - (CH ^) W - (w = 1t12), which may be interrupted by the group -0- or -CH = CH-, or may be substituted with hydroxyl.
    or methyl, group
    —CH — CHg — 0 —0 and g —0CHCH 3 or a residue of the formula where B is a single bond, —0—, methylene, p = 1.2 or A together with nitrogen atoms means the remainder of the formulas * 5 where Re is A 7 and mean the radical —CH ^ COOCHj or CH ^ COOC ^ H ^, and a compound of the formula is used as the dihaloid compound
    X-R5-X where X is halogen and A ^ represents
    类似技术:
    公开号 | 公开日 | 专利标题
    SU890981A3|1981-12-15|Method of preparing polymeric quaternary ammonium salts
    DE3048122C2|1994-05-11|Polycationic polymers, their preparation and their use
    CH638362A|1983-09-30|
    EP0113856B1|1986-09-24|Process for improving the fastness to light of polyamide dyeings
    US4668273A|1987-05-26|Quaternary ammonium salts of diepoxides and diamines, their preparation and use
    EP0259251B1|1991-02-27|Cationic compounds from the reaction of carbamides with epihalogen hydrines
    EP0221855B1|1990-07-11|Diquaternary ammonium salts, their preparation and their use as textile finishing agents
    EP0431423A2|1991-06-12|Basic polycondensation products as well as their use as dye additives
    EP0242577A2|1987-10-28|Process for the treatment of fibre materials
    DE4101822A1|1992-07-30|PIGMENT PRESSURE ON FIBROUS MATERIALS
    EP0238948A2|1987-09-30|Basic polycondensate
    EP0038299B1|1984-11-14|Cationic compounds
    DE1906709B2|1974-03-07|Process for the preparation of basic azo dyes and their use
    DE2924471C2|1986-10-30|Quaternized polyamines and their preparation
    CH457662A|1968-06-15|Process for the preparation of basic dyes
    EP0438380B1|1996-05-22|Polymerized quaternary diallylammonium compounds
    US4087247A|1978-05-02|Process for the dyeing of polyacrylonitrile fibers
    EP0166242A1|1986-01-02|Water soluble cation-active polyelectrolytes, their preparation and their use
    EP0103274A2|1984-03-21|Perfluoroalkylmaleic amides and perfluorofumaric amides, process for their preparation and their use as stain repellent agents
    DE3525104C2|1988-05-26|
    EP0248356A1|1987-12-09|Naphthalimides containing sulfuric-acid ester groups, process for their preparation and their use
    DE2442250A1|1975-03-13|PROCESS FOR EQUIPMENT OF NATURAL AND SYNTHETIC FIBER MATERIALS
    DE2527792A1|1976-01-29|ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE
    US3574515A|1971-04-13|Process for dyeing and printing of cellulose fibre materials using a copper ammine complex of trimethylamine-tricarboxylic acid
    EP0013540A1|1980-07-23|Process for the dyeing and printing of fibrous material with polymerized quaternary ammonium salts as auxiliary agents
    同族专利:
    公开号 | 公开日
    DK580476A|1977-06-24|
    BE849728A|1977-06-22|
    DD129075A5|1977-12-28|
    FR2336434A1|1977-07-22|
    ZA767612B|1977-11-30|
    CH1669775A4|1977-06-30|
    GB1546809A|1979-05-31|
    SE7614450L|1977-06-24|
    PL108409B1|1980-04-30|
    FR2336434B1|1980-10-31|
    AU2082076A|1978-06-29|
    CA1069522A|1980-01-08|
    ES454490A1|1978-03-01|
    AU511139B2|1980-07-31|
    NL7613931A|1977-06-27|
    DE2657582A1|1977-07-07|
    CH599389B5|1978-05-31|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH1669775A|CH599389B5|1975-12-23|1975-12-23|
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