# US 4,394,490 A · Water dispersible polyester compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,490 A - Document ID: US4394490A - Status: Granted - Kind: A - Application number: 06/425,146 - Filed: 1982-09-28 - Granted: 1983-07-19 - Earliest claimed: 1982-09-28 - Assignees: The Goodyear Tire & Rubber Company - Inventors: William C. T. Tung - Web page: https://patentgrep.com/patent/US4394490A ## CPC - C08G 63/688: containing sulfur - C08G 63/685: containing nitrogen - C09D 167/00: Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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) ## Abstract Water soluble polyester compositions which, upon cure, are water insoluble. These water-based polyesters are made utilizing hydantoin compounds with salts of a compound containing a sulfo acid group therein. Such compositions are useful as coatings, paints, and the like and eliminate any recovery problems or toxicity problems normally related with many organic solvents. ## Claims ### Claim 1 A water dispersible polyester, comprising: a polyester, said polyester comprising a mixture of units in the polymer chain made from the reaction product of a diacid component and a diol, said diacid component comprising up to 30 mole percent by weight of a compound selected from the group consisting of an alkyl dicarboxylic acid having from 4 to 20 carbon atoms, a diester of an alkyl dicarboxylic acid having from 6 to 20 carbon atoms, and combinations thereof, at least 70 mole percent of an aromatic dicarboxylic acid or ester thereof selected from the group consisting of an aryl dicarboxylic acid having from 8 to 20 carbon atoms, an alkyl substituted aryl dicarboxylic acid having from 9 to 20 carbon atoms, a diester of an alkyl substituted aryl dicarboxylic acid having from 11 to 20 carbon atoms, a diester of an aryl dicarboxylic acid having from 10 to 20 carbon atoms, and combinations thereof; said diol comprising up to 30 mole percent of a diol selected from the group consisting of a glycol having from 2 to 12 carbon atoms, a glycol ether having from 4 to 12 carbon atoms, or combinations thereof, said diol component also having at least 70 mole percent of a hydantoin compound having the formula ##STR3## wherein R.sub.1 and R.sub.2 can be the same or different and is an alkyl having from 1 to 2 carbon atoms, and where R.sub.3 and R.sub.4 can be the same or different and is an alkyl having from 1 to 4 carbon atoms. ### Claim 2 (depends on 1) A water dispersible polyester according to claim 1, including reacting from about 0.1 to about 10 mole percent of an alkali salt of a sulfo alkyl isophthalate based upon the total amount of said acid or diester, said alkyl having from 1 to 5 carbon atoms, said polymer chain containing units of said sulfo compound therein. ### Claim 3 (depends on 2) A water dispersible polyester according to claim 2, wherein said alkyl dicarboxylic acid has from 4 to 12 carbon atoms, wherein said diester of said alkyl dicarboxylic acid has from 6 to 12 carbon atoms, wherein said aryl dicarboxylic acid has from 8 to 16 carbon atoms, wherein said alkyl substituted aryl dicarboxylic acid has from 9 to 16 carbon atoms, wherein said diester of said alkyl substituted aryl dicarboxylic acid has from 11 to 15 carbon atoms, wherein said diester of said aryl dicarboxylic acid has from 10 to 14 carbon atoms, wherein said glycol has from 2 to 8 carbon atoms, wherein said glycol ether has from 4 to 8 carbon atoms, wherein said R.sub.1 and R.sub.2 of said hydantoin compound is methyl, and wherein R.sub.3 and R.sub.4, of said hydantoin compound is ethyl. ### Claim 4 (depends on 3) A water dispersible polyester according to claim 3, wherein said acid is terephthalic acid or isophthalic acid, wherein said ester is dimethylterephthalate or dimethyl isophthalate, and wherein said diol is ethylene glycol. ### Claim 5 (depends on 4) A water dispersible polyester according to claim 4, including reacting during third stage of the reaction from about 1 to about 30 mole percent of an acid anhydride having from 4 to 20 carbon atoms based upon the total amount of said acid or diester thereof. ### Claim 6 (depends on 5) A water dispersible polyester according to claim 5, wherein the amount of said hydantoin compound is at least 80 mole percent based upon the total amount of said diols, and wherein the intrinsic viscosity of said polyester ranges from about 0.15 to about 0.3 dl/g in a 60/40 solution of phenol/tetrachloroethane. ### Claim 7 (depends on 6) A water dispersible polyester according to claim 6, wherein said sulfo salt compound is the sodium salt of sulfo dimethyl isophthalate in an amount ranging from about 1 to about 10 mole percent wherein said hydantoin compound is Di(2-hydroxyethyl) dimethylhydantion, and wherein said acid anhydride is phthalic anhydride or trimellitic anhydride, wherein said addition of said anhydride is from about S3.7 to S3.9, and wherein said amount of said anhydride added is from about 5 to about 25 mole percent. ### Claim 8 (depends on 1, 2, 4, 5) A water dispersible polyester according to claim 1, 2, 4, 5, or 7, wherein said dispersible polyester has been cured by a curing agent, so that said polyester is water insoluble. ### Claim 9 (depends on 8) A water dispersible polyester according to claim 8, wherein said curing agent is an epoxy compound. ### Claim 10 (depends on 8) A water dispersible polyester according to claim 8, wherein said curing agent is hexamethoxymethyl melamine.