# US 5,708,058 A · Aqueous coating composition based on low-solvent modified epoxy resin dispersions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,058 A - Document ID: US5708058A - Status: Granted - Kind: A - Application number: 08/719,647 - Filed: 1996-09-25 - Granted: 1998-01-13 - Earliest claimed: 1995-09-29 - Assignees: Vianova Resins GmbH - Inventors: Armin Pfeil; Bernhard Stengel-Rutkowski; Claus Godau - Web page: https://patentgrep.com/patent/US5708058A ## CPC - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - C08G 59/04: of polyhydroxy compounds with epihalohydrins or precursors thereof - C08G 59/066: {with chain extension or advancing agents} - C08G 59/145: {Compounds containing one epoxy group} - C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 - Y10T 428/31511: Of epoxy ether - 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Aqueous low-solvent coating compositions comprising a modified epoxy resin dispersion comprising an epoxy resin which is prepared by condensation of one or more epoxide compounds having at least two epoxide groups per molecule with an aromatic polyol; a dispersant comprising a condensation product of an aliphatic polyol and an epoxide compound having at least two epoxide groups per molecule; a diluent consisting of ethylenically unsaturated otherwise inert or, if desired, functional monomers capable of free-radical polymerization or copolymerization, and water, and also an aqueous curing agent for the modified epoxy resin (I), which is suitable for curing at room temperature or at elevated temperatures (forced drying), components (I) and (II) being employed in proportions by mass such that the ratio of the number of epoxide groups which are capable of reaction to the number of amine hydrogen atoms is between 1:0.75 and 1:2. The coating compositions can be employed to produce matt coatings and in adhesives. ## Claims ### Claim 1 An aqueous, low-solvent coating composition comprising: (I) a modified epoxy resin dispersion comprising (A) an epoxy resin which is a condensation product of mass fractions of the following starting materials, (A-1) from 50 to 95% of one or more epoxide compounds having at least two epoxide groups per molecule (A-2) from 5 to 50% of an aromatic polyol; (B) a dispersant comprising (B-1) a condensation product of (B-11) an aliphatic polyol having a weight-average molar mass M.sub.W of from 200 to 20,000 g/mol, and (B-12) an epoxide compound having at least two epoxide groups per molecule; (C) a diluent comprising (C-1) ethylenically unsaturated, otherwise inert or, functional monomers capable of free-radical polymerization or copolymerization, (D) and water, and (II) an aqueous curing agent for the modified epoxy resin (I), which is suitable for curing at room temperature or at elevated temperatures which curing agent is selected from the group consisting of polyamines, Mannich bases, epoxy-amine adducts with free amino groups, polyamidoamines, and latent curing agents, components (I) and (II) being employed in mass fractions such that the ratio of the number of epoxide groups which are capable of reaction to the number of amine hydrogen atoms is between 1:0.75 and 1:2. ### Claim 2 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the epoxy resin (A) is a condensation product of mass fractions of the following starting materials (A-1) from 55 to 85% of one or more epoxide compounds having at least two epoxide groups per molecule, and (A-2) from 15 to 45% of an aromatic polyol. ### Claim 3 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the mixture of starting materials used to prepare the epoxy resin (A) further comprises a mass fraction of (A-3) from 1 to 25% of a modifying compound having at least two epoxide-reactive groups. ### Claim 4 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein in the starting materials for preparing the dispersant (B1) the ratio of the number of OH groups to that of the epoxide groups is from 1:0.5 to 1:3.5, and the epoxide group content of this condensation product (B1) is between 2.5 and 200 mmol/kg. ### Claim 5 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the dispersant (B) additionally comprises a nonionic surfactant (B2). ### Claim 6 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the diluent (C) additionally comprises a low molar mass liquid epoxide compound (C-2). ### Claim 7 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the dispersion comprises a mass fraction of up to 10% of an organic solvent. ### Claim 8 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the epoxide compounds according to (A-1) and (B-12) can be identical or different and are selected from the group consisting of polyglycidyl ethers of polyhydric alcohols, phenols, hydrogenated phenols and novolaks, and polyglycidyl esters of aliphatic, cycloaliphatic and aromatic polycarboxylic acids having 2 to 40 carbon atoms with an epoxide group content of between 300 and 12,000 mmol/kg. ### Claim 9 (depends on 8) An aqueous, low-solvent coating composition as claimed in claim 8, wherein the epoxide group content of (A-1) and (B-12), in each case independently of one another, is between 500 and 11,000 mmol/kg. ### Claim 10 (depends on 8) An aqueous, low-solvent coating composition as claimed in claim 8, wherein the epoxide group content of (A-1) and (B-12), in each case independently of one another, is between 2800 and 10,000 mmol/kg. ### Claim 11 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the aromatic polyol (A-2) is selected from the group consisting of dihydric and polyhydric mono- and polycyclic phenols, their halogenation products, and novolaks. ### Claim 12 (depends on 3) An aqueous, low-solvent coating composition as claimed in claim 3, wherein the modifying compound (A-3) is a substance other than aromatic polyols and has at least two functional groups which are reactive toward epoxide groups. ### Claim 13 (depends on 3) An aqueous, low-solvent coating composition as claimed in claim 3, wherein the modifying compound (A-3) is selected from the group consisting of aliphatic polyamines, polyoxyalkylene mono- and polyoxyalkylene di-amines, aliphatic and aromatic polycarboxylic acids having 2 to 60 carbon atoms, and aliphatic polyols. ### Claim 14 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the compound (B-11) selected from polyoxyalkylene polyglycols having a weight-average molar mass of from 600 to 1200 g/mol. ### Claim 15 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the compound (C-1) is selected from the group consisting of esters of .alpha.,.beta.-olefinically unsaturated carboxylic acids with aliphatic alcohols having 1 to 18 carbon atoms, aromatic vinyl compounds, vinyl esters and vinyl halides, .alpha.,.beta.-olefinically unsaturated carboxylic acids and their amides and nitriles. ### Claim 16 (depends on 6) An aqueous, low-solvent coating composition as claimed in claim 6, wherein the compound (C-2) is an ether of glycidyl alcohol and compounds selected from the group consisting of mono-and polyhydric phenols, alkyl-substituted phenols, and mono- and polyhydric branched and unbranched alcohols, and an ester of glycidyl alcohol with branched or unbranched aliphatic carboxylic acids having 2 to 40 carbon atoms. ### Claim 17 (depends on 1) An aqueous, low-solvent coating composition as claimed in claim 1, wherein the latent curing agent is selected from the group consisting of urea, dicyandiamide, imidazole, imidazoles, imidazolines, substituted imidazoles, substituted imidazolines, guanidine, acetoguanamine and benzoguanamine. ### Claim 18 A process for preparing an aqueous, low-solvent coating composition, which comprises (I) a modified epoxy resin dispersion comprising (A) an epoxy resin which is a condensation product of mass fractions of the following starting materials: (A-1) from 50 to 95% of one or more epoxide compounds having at least two epoxide groups per molecule (A-2) from 5 to 50% of an aromatic polyol; (B) a dispersant comprising (B-1) a condensation product of (B-11) an aliphatic polyol having a weight-average molar mass M.sub.W of from 200 to 20,000 g/mol, and (B-12) an epoxide compound having at least two epoxide groups per molecule; (C) a diluent comprising (C-1) ethylenically unsaturated, otherwise inert or, functional monomers capable of free-radical polymerization or copolymerization, (D) and water, and (II) an aqueous curing agent for the modified epoxy resin (I), which is suitable for curing at room temperature or at elevated temperatures which curing agent is selected from the group consisting of polyamines, Mannich bases, epoxy-amine adducts with free amino groups, polyamidoamines, and latent curing agents, wherein said process comprising the following steps: first preparing the epoxy resin (A) by condensation of components (A-1) and (A-2) at an elevated temperature in the presence of a condensation catalyst, then adding at least a portion of the diluent (C) at a lower temperature and, optionally, carrying out a partial reaction of the monomers (C-1) with the epoxy resin (A), subsequently incorporating the dispersant (B) by homogenization and obtaining an aqueous dispersion by portionwise addition of water (D), after which the monomers (C-1) are polymerized with the aid of an initiator system and, optionally, with the addition of the remaining diluent (C), and adding the aqueous curing agent (II) before the modified epoxy resin dispersion (I) is used. ### Claim 19 (depends on 18) An aqueous, low-solvent coating composition prepared by the process of claim 18. ### Claim 20 (depends on 1) A coated article, comprising a substrate and a coating from a coating composition as claimed in claim 1. ### Claim 21 (depends on 20) A coated article as claimed in claim 20, wherein the coating comprises a matt clearcoat. ### Claim 22 (depends on 21) A coated article as claimed in claim 21, comprising a single layer matt clearcoat coating. ### Claim 23 (depends on 1) A water-dilutable adhesive comprising an aqueous dispersion as claimed in claim 1. ### Claim 24 (depends on 1) An aqueous coating composition as claimed in claim 1 which is substantially free of organic solvent. ### Claim 25 (depends on 18) A process according to claim 18, wherein the curing agent is in an aqueous system. ### Claim 26 (depends on 18) A process according to claim 18, wherein the curing agent is selected from the group consisting of polyamines, Mannich bases, epoxy-amine adducts with free amino groups, and polyamidoamines. ### Claim 27 (depends on 1) An aqueous, low-solvent coating composition according to claim 1, wherein the curing agent is selected from the group consisting of polyamines, Mannich bases, epoxy-amine adducts with free amino groups, and polyamidoamines.