# US 5,708,059 A · Stable, aqueous epoxy resin dispersions, processes for their preparation, and their use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,059 A - Document ID: US5708059A - Status: Granted - Kind: A - Application number: 08/798,759 - Filed: 1997-02-11 - Granted: 1998-01-13 - Earliest claimed: 1994-06-30 - Assignees: Hoechst Aktiengesellschaft - Inventors: Armin Pfeil; Michael Hoenel; Uwe Neumann - Web page: https://patentgrep.com/patent/US5708059A ## CPC - C09D 11/10: based on artificial resins - C08F 283/10: on to polymers containing more than one epoxy radical per molecule {(C08F283/004 takes precedence)} - C08F 290/064: {Polymers containing more than one epoxy group per molecule} - C08F 290/144: {Polymers containing more than one epoxy group per molecule} - C08G 18/0814: {containing ammonium groups or groups forming them} - C08G 18/581: {Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component (with amines C08G18/584)} - C08G 18/8029: {Masked aromatic polyisocyanates} - C08G 59/066: {with chain extension or advancing agents} - C08G 59/50: Amines - C08G 59/56: together with other curing agents - C08L 51/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A stable, aqueous epoxy resin dispersion including: (A) an epoxy resin prepared by condensation of at least one epoxide compound having on average at least two epoxide groups per molecule, with an aralkylated polyhydroxy aromatic compound obtained by reaction of a polyhydroxy aromatic compound with an aromatic compound which carries an alkenyl group; (B) a dispersant; and water, is useful, for example, in a coating or adhesive. ## Claims ### Claim 1 A stable, aqueous epoxy resin dispersion comprising: (A) an epoxy resin formed by condensation of (A-1) at least one epoxide compound having on average at least two epoxide groups per molecule, with (A-2) an aralkylated or alkylated polyhydroxy aromatic compound formed by reacting (A-2a) a polyhydroxy aromatic compound with (A-2b) an aromatic or aliphatic compound which carried an alkenyl group; (B) a dispersant; (C) a diluent selected from one or more low molecular weight, liquid, epoxy-functional compounds (C2); and (D) water. ### Claim 2 (depends on 1) A stable aqueous epoxy resin dispersion as claimed in claim 1, where (A-2) comprises an aralkylated polyhydroxy aromatic compound. ### Claim 3 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, wherein component (A1) comprises an epoxide compound which has an epoxide equivalent weight of from 100 to 2000 g/mol. ### Claim 4 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, wherein the dispersant (B) comprises a condensation product (B1) of a polyol (B1a) and an epoxide compound (B1b) having at least two epoxide groups per molecule. ### Claim 5 (depends on 4) A stable, aqueous epoxy resin dispersion as claimed in claim 4, wherein the dispersant (B) additionally comprises at least one surfactant (B2). ### Claim 6 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, which is free from organic solvent. ### Claim 7 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, wherein the average particle size of the dispersed resin is less than 1 .mu.m. ### Claim 8 (depends on 4) A stable, aqueous epoxy resin dispersion as claimed in claim 4, wherein the dispersant comprises a condensation product (B1) of a polyetherpolyol (B1a) and a polyglycidyl ether (B1b). ### Claim 9 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, which further comprises an addition polymer formed from olefinically unsaturated monomers. ### Claim 10 (depends on 1) A stable, aqueous epoxy resin dispersion as claimed in claim 1, which additionally comprises one or more organic solvents. ### Claim 11 A stable, aqueous epoxy resin dispersion comprising: (A) an epoxy resin formed by condensation of (A-1) at least one epoxide compound having on average at least two epoxide groups per molecule, with (A-2) an aralkylated or alkylated polyhydroxy aromatic compound formed by reacting (A-2a) a polyhydroxy aromatic compound with (A-2b) an aromatic or aliphatic compound which carried an alkenyl group; (B) a dispersant; (C) an addition polymer prepared by free-radical polymerization of olefinically unsaturated monomers (C1) in the presence of epoxy resin (A); (D) water. ### Claim 12 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, wherein the polymer (C) is prepared by the polymerization of monomers (C1) with one or more free-radical initiators in the presence of a dispersion of the epoxy resin (A) in water (D). ### Claim 13 (depends on 11) A stable, aqueous epoxy resin dispersion as claimed in claim 11, wherein the ratio by mass of epoxy resin (A) to the addition polymer (C) is from 99.5:0.5 to 20:80. ### Claim 14 (depends on 11) A process for the preparation of a stable, aqueous epoxy resin dispersion as claimed in claim 11, which comprises: preparing an epoxy resin (A) from the epoxide compound (A1) and the aralkylated polyhydroxy aromatic compound (A2), dispersing the modified epoxy resin (A) in water with the addition of a dispersant (B) and of at least one olefinically unsaturated monomer (C1), and polymerizing (C1) by adding a radical-forming initiator to form addition polymer (C). ### Claim 15 (depends on 14) A process as claimed in claim 14, where in addition to the monomers (C1), at least one substance is added to epoxy resin (A) which is selected from low molecular weight, liquid epoxide compounds (C2) and inert organic solvents (C3), conjointly with, prior to, or following the addition of the monomer (C1). ### Claim 16 (depends on 11) A stable, aqueous epoxy resin dispersion as claimed in claim 11, wherein the dispersant (B) comprises a condensation product (B1) of a polyol (B1a) and an epoxide compound (B1b) having at least two epoxide groups per molecule. ### Claim 17 (depends on 16) A stable, aqueous epoxy resin dispersion as claimed in claim 16, wherein the dispersant comprises a condensation product (B1) of a polyetherpolyol (B1a) and a polyglycidyl ether (B1b). ### Claim 18 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, where (A-2) comprises an aralkylated polyhydroxy aromatic compound. ### Claim 19 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, where the olefinically unsaturated monomers (C1) contain functional groups capable of curing the epoxy resin (A). ### Claim 20 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, wherein the epoxy resin (A) is cured. ### Claim 21 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, wherein (A-2b) is an aromatic compound which carried an alkenyl group. ### Claim 22 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, wherein (A-2b) is an aromatic compound which carried an alkenyl group. ### Claim 23 (depends on 1) A stable aqueous epoxy resin dispersion as claimed in claim 1, wherein (A-2b) comprises an aliphatic compound selected from vinyl esters, vinyl ethers, esters of acrylic or methacrylic acid with monoalcohols having 1 to 18 carbon atoms, or hydroxyl C.sub.2 - to C.sub.4 - alkyl (meth)acrylates. ### Claim 24 (depends on 11) A stable aqueous epoxy resin dispersion as claimed in claim 11, wherein (A-2b) comprises an aliphatic compound selected from vinyl esters, vinyl ethers, esters of acrylic or methacrylic acid with monoalcohols having 1 to 18 carbon atoms, or hydroxyl C.sub.2 - to C.sub.4 - alkyl (meth)acrylates. ### Claim 25 (depends on 1) A stable epoxy resin dispersion as claimed in claim 1, wherein the mass of component (C2) is from 1 to 25% based on the sum of the masses of components (A) and (C). ### Claim 26 (depends on 1) A stable epoxy resin dispersion as claimed in claim 1, wherein the diluents (C2) are selected from the group consisting of para-tert, butylphenyl glycidyl ether, n-butyl glycidyl ether, phenyl glycidyl ether, ortho-cresyl glycidyl ether, butanediol diglycidyl ether, hexanediol diglycidyl ether, neopentylglycol diglycidyl ether, dimethylolcyclohexane diglycidyl ether, 2-ethylhexyl glycidyl ether, versatic acid glycidyl ester, and the diglycidyl ethers of bisphenol A and bisphenol F.