KR900701714A - Polymerizable Surfactants - Google Patents

Abstract

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Description

Polymerizable Surfactants

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Claims (35)

The compound represented by the following general formula. RO- (R ¹ O) _m (E0) _n-1 , -CH ₂ CH ₂ -X Wherein R is C ₂ -C ₈ alkenyl, acrylyl, acrylyl (C ₁ -C ₁₀ ) alkyl, methacrylyl, ethacylyl (C ₁ -C ₁₀ ) alkyl, vinylphenyl and vinylphenylene ( C ₁ -C ₆ ) alkyl, R′O is selected from the group consisting of divalent alkyleneoxy groups derived from cyclic ethers other than ethylene oxide and mixtures of these alkyleneoxy groups, E is Divalent ethylene radicals, m and n are each a number from 5 to about 100, the ratio of m: n is from about 20: 1 to about 1: 20, and X is hydroxyl, chloride, tertiary amino, and anionic Group selected from the group consisting of sulfonates, sulfate phosphates, acetates, isethionates (and alkali metal salts of these anionic groups). The compound of claim 1, wherein the alkyleneoxy group R′O is of the formula —CH ₂ CH (R ″) — O—, wherein R ″ is methyl, ethyl, phenyl, phenyloxymethyl and —CH ₂ — (CH ₂ ) is represented by ₂ -CH ₂ -O-] a, m and n is a number from about 5 to about 50, respectively, X represents chloride, hydroxyl, tertiary amino, and the anionic group of sulfonate, sulfate, phosphate , Acetates, isethionates (and compounds selected from the group consisting of alkali metal salts of these anionic groups.) The compound of claim 1, wherein R is selected from the group consisting of vinyl and allyl, and R'O is a divalent epoxy 2 group derived from propylene oxide, butylene oxide and a mixture of propylene oxide and butylene oxide, m And n are each a number from about 5 to about 50 and X is chloride. Compounds selected from the group consisting of hydroxyl, tertiary amino and anionic groups sulfonates, sulfates, phosphate acetates, isethionates (and alkali metal salts of these anionic groups). The compound of claim 3, wherein the tertiary amino group is of the formula —N ″ (R ₂ ) (R ₃ ) R ₄ , wherein R ₂ , R ₃ and R ₄ are each C ₁ -C ₅ alkyl and hydroxy (C _It is selected from the group consisting of ₁ -C ₅ ) alkyl. 4. The compound of claim 3, wherein R is allyl and R'O is a divalent epoxy group derived from butylene oxide. 6. The compound of claim 5, wherein X is selected from the group consisting of sulfates, sulfonates, phosphates (and alkali metal salts of these anionic groups) wherein X is chloride, hydroxyl, and an anionic group. A process for carrying out free-radical initiated polymerization of ethylenically unsaturated reactant monomers, wherein the polymerization is carried out in the presence of about 1 to about 25 weight percent of a compound represented by the following general formula based on the total amount of reactant monomers: . RO- (R ¹ O) _m (E0) _n-1 , -CH ₂ CH ₂ -X Wherein R is C ₂ -C ₁₈ alkenyl, acrylyl, acrylyl (C ₁ -C ₁₀ ) alkyl, methacrylyl, methacrylyl (C ₁ -C ₆ ) alkyl, vinylphenyl and vinylphenylene ( C ₁ -C ₆ ) alkyl, R′O is selected from the group consisting of divalent alkyleneoxy groups derived from cyclic ethers other than ethylene oxide and mixtures of these alkyleneoxy groups, E is Divalent ethylene radical, m and n are each a number from about 5 to about 100, the ratio of m: n is from about 20: 1 to about 1:20, and X is hydroxyl, chloride, tertiary amino, and an anion Is a group selected from the group consisting of sulfonates, sulfates, phosphates, acetates, isethionates (and alkylimetal salts of these anionic groups). 8. The method of claim 7, wherein said polymerization is emulsion polymerization. The method of claim 8, wherein a nonpolymerizable surfactant is present during the polymerization. The method of claim 8, wherein the ethylenically unsaturated monomers are mono- and polyunsaturated hydrocarbon monomers, vinyl esters, vinyl ethers, monoethylenically unsaturated mono- and polycarboxylic acids and their alkyl esters, nitriles, vinyl halides, vinylidene halides. , Amides of unsaturated carboxylic acids, amino monomers and mixtures of said monomers. The method of claim 10 wherein said monoethylenically unsaturated monocarboxylic acid is acrylic acid or methacrylic acid and their alkyl esters are C ₁ -C ₁₂ alkyl esters. The method of claim 8, wherein the ethylenically unsaturated monomer is a vinyl acetate-acrylic monomer mixture, vinyl acetate, styrene-acrylic monomer mixture, styrene-butadiene monomer mixture, vinyl chloride, vinyl fluoride, vinylidene chloride, vinylidene fluorine. Lide and an acrylic monomer mixture. A process for carrying out free-radical initiated emulsion polymerization of ethylenically unsaturated reactant monomers, wherein the polymerization is carried out in the presence of about 1 to about 25 weight percent of a compound represented by the following general formula based on the total amount of reactant monomers Way. RO- (R ¹ O) _m (EO) _n-1 -CH ₂ CH ₂ -X Wherein R is C ₂ -C ₁₈ alkenyl, acrylyl, acrylyl (C ₁ -C ₁₀ ) alkyl, methacrylyl, methacrylyl (C ₁ -C ₆ ) alkyl, vinylphenyl and vinylphenylene ( C ₁ -C ₆ ) alkyl, R′O is selected from the group of the formula —CH ₂ CH (R ″) — O—, where R ″ is methyl, ethyl phenyl, phenyloxyethyl and —CH ₂ — Divalent alkyleneoxy group represented by (CH ₂ ) ₂ -CH ₂ -O-) and a mixture of such alkyleneoxy groups, E is a divalent ethylene radical, m and n are each A number from about 5 to about 50, and the ratio of m: n is from about 20: 1 to about 1: 20, and X is a chloride, hydroxyl, tertiary amino, and an anionic group sulfonate, sulfate, phosphate, acetate , Isethionate (and alkali metal salts of these anionic groups). The method of claim 13, wherein the compound represented by the general formula RO— (R′O) _m − (EO) _{n −1} , —CH ₂ CH ₂ —X is present in an amount of about 1 to about 10 weight percent. The method of claim 14, wherein a nonpolymerizable surfactant is present during the polymerization process. 15. The compound of claim 14, wherein R is selected from the group consisting of vinyl and allyl, and R'O is a divalent epoxy group derived from propylene oxide, mutylene oxide and a mixture of propylene oxide and butylene oxide, m and n Are each a number from about 5 to about 50 and X is a chloride, hydroxyl, tertiary amino, and an anionic group. Sulphate, phosphate, acetate, isethionate (and alkali metal salts of these anionic groups). 17. The process of claim 16 wherein the ethylenically unsaturated monomers are mono- and polyunsaturated hydrocarbon monomers, vinyl esters, vinyl ethers, monoethylenically unsaturated mono- and polycarboxylic acids and their alkyl esters, nitriles, vinyl halides, vinylidene halides. , Amides of unsaturated carboxylic acids, amino monomers and mixtures of said monomers. 18. The method of claim 17, wherein said monoethylenically unsaturated monocarboxylic acid is acrylic acid or methacrylic acid and their alkyl esters are C ₁ -C ₁₂ alkyl esters. The method of claim 16, wherein the ethylenically unsaturated monomer is a vinyl acetate-acrylic monomer mixture, vinyl acetate, styrene-acrylic monomer mixture, styrene-butadiene monomer mixture, vinyl chloride, vinyl fluoride, vinylidene chloride, vinylidene Fluoride and acrylic monomer mixture. 20. The method of claim 19, wherein R is allyl and R'O is a divalent epoxy group derived from butylene oxide. 21. The method of claim 20, wherein the X is chloride, hydroxyl, and anionic groups are selected from the group consisting of sulfates, sulfonates, phosphates (and alkali metal salts of these anionic groups). A substantially water-soluble surfactant free polymer product prepared by free-radical initiating polymerization of an ethylenically unsaturated reactant monomer in the presence of about 1 to about 25 weight percent of a compound represented by the following general formula based on the total amount of reactant monomers. RO- (R′O) _m- (E0) _n-1 -CH ₂ CH ₂ -X Wherein R is C ₂ -C ₁₈ alkenyl, acrylyl, acrylyl (C ₁ -C ₁₀ ) alkyl, methacrylyl, methacrylyl (C ₁ -C ₆ ) alkyl, vinylphenyl and vinylphenylene ( Is selected from the group consisting of C ₁ -C ₆ ) alkyl, R′O is selected from the group consisting of divalent alkyleneoxy groups derived from cyclic ethers other than ethylene oxides and mixtures of such alkyleneoxy groups, E is Divalent ethylene radical, m and n are each a number from about 5 to about 50, the ratio of m: n is from about 20: 1 to about 1:20, and X is hydroxyl, chloride, tertiary amino, and an anion Sex group is selected from the group consisting of sulfonates, sulfates, phosphates, acetates, isethionates (and alkali metal salts of these anionic groups). The polymer product of claim 22 wherein the polymer is in the form of a latex. 23. The compound of claim 22 wherein R is selected from the group consisting of vinyl and allyl, and R'O is a divalent epoxy group derived from a mixture of propylene oxide, butylene oxide and propylene oxide and butylene oxide, m and n is a number from about 5 to about 50O, respectively, and X is a chloride, hydroxyl, tertiary amino, and anionic groups sulfonates, sulfates, phosphates, acetates, isethionates (and alkali metal salts of these anionic groups) A polymer product selected from the group consisting of. The method of claim 24, wherein the ethylenically unsaturated monomers are mono- and polyunsaturated hydrocarbon monomers, vinyl esters, vinyl ethers, monoethylenically unsaturated mono- and polycarboxylic acids and their alkyl esters, nitriles, vinyl halides, vinylidene halides. , Amides of unsaturated carboxylic acids, amino monomers and mixtures of said monomers. 27. The polymer product of claim 25, wherein said monoethylenically unsaturated monocarboxylic acid is acrylic acid or methacrylic acid and their alkyl esters are C ₁ -C ₁₂ alkyl esters. The method of claim 24, wherein the ethylenically unsaturated monomer is a vinyl acetate-acrylic monomer mixture, vinyl acetate, styrene-acrylic monomer mixture, styrene-butadiene monomer mixture, vinyl chloride, vinyl fluoride, vinylidene chloride, vinylidene A polymer product selected from the group consisting of fluorides and acrylic monomer mixtures. The polymer product of claim 27, wherein R is allyl and R'O is a divalent epoxy group derived from butylene oxide. A substantially water free surfactant polymer product prepared by free-radical initiated emulsion polymerization of an ethylenically unsaturated reactant monomer in the presence of about 1 to about 10 weight percent of a compound represented by the following general formula based on the total amount of reactant monomers. RO- (R′O) _m- (E0) _n-1 -CH ₂ CH ₂ -X Wherein R is C ₂ -C ₁₈ alkenyl, acrylyl, acrylyl (C ₁ -C ₁₀ ) alkyl, methacrylyl, methacrylyl (C ₁ -C ₁₀ ) alkyl, vinylphenyl and vinylphenylene ( C ₁ -C ₆ ) alkyl, wherein R′O is selected from the formula —CH ₂ CH (R ″) — O—, wherein R ″ is methyl, ethyl, phenyl, phenyloxymethyl and —CH ₂ Divalent alkyleneoxy group represented by-(CH ₂ ) ₂ -CH ₂ -O-) and a mixture of such alkyleneoxy groups, E is a divalent ethylene radical, m and n are Each having a number from about 5 to about 50, and the ratio of m: n is from about 20: 1 to about 1: 20, where X is chloride, hydroxyl, tertiary amino, and anionic groups sulfonates, sulfates, phosphates, Acetates, isethionates (and alkali metal salts of these anionic groups). 30. The compound of claim 29, wherein R is selected from the group consisting of vinyl and allyl, R'O is a divalent epoxy group derived from a mixture of propylene oxide, butylene oxide and propylene oxide with butylene oxide, m and n is a number from about 5 to about 50 each, and X is a chloride, hydroxyl, tertiary amino, and anionic groups sulfonates, sulfates, phosphates, acetates, isethionates (and alkali metal salts of these anionic groups) A polymer product selected from the group consisting of. 31. The method of claim 30, wherein the ethylenically unsaturated monomers are mono- and polyunsaturated hydrocarbon monomers, vinyl esters, vinyl ethers, monoethylenically unsaturated mono- and polycarboxylic acids and their alkyl esters, nitriles, vinyl halides, vinylidene halides, A polymer product selected from the group consisting of amides of unsaturated carboxylic acids, amino monomers and mixtures of these monomers. 32. The polymer product of claim 31, wherein said monoethylenically unsaturated monocarboxylic acid is acrylic acid or methacrylic acid and their alkyl esters are C ₁ -C ₁₂ alkyl esters. The method of claim 31, wherein the ethylenically unsaturated monomer is a vinyl acetate-acrylic monomer mixture, vinyl acetate, styrene-acrylic monomer mixture, styrene-butadiene monomer mixture, vinyl chloride, vinyl fluoride, vinylidene chloride, vinylidene fluorine A polymer product selected from the group consisting of a lide and an acrylic monomer mixture. 34. The polymer product of claim 33, wherein R is allyl and R'O is a divalent epoxy group derived from butylene oxide. A coating prepared from the polymer product of claim 33 having a water sensitivity such that the contact angle of water droplets placed on the coating is less than 5 °. ※ Note: The disclosure is based on the initial application.