# US 4,396,732 A · Water soluble amine resins which are Mannich bases > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,396,732 A - Document ID: US4396732A - Status: Granted - Kind: A - Application number: 06/282,512 - Filed: 1981-07-13 - Granted: 1983-08-02 - Earliest claimed: 1981-07-13 - Assignees: DeSoto, Inc. - Inventors: Kazys Sekmakas; Raj Shah - Web page: https://patentgrep.com/patent/US4396732A ## CPC - C09D 5/4419: {with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds} - C08G 14/06: and monomers containing hydrogen attached to nitrogen - C08G 14/14: Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds - C08G 59/623: {Aminophenols} - 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 ## Abstract An amine resin soluble in water with the aid of an acid is produced by reacting a dihydric phenolic compound, such as a bisphenol, with a stoichiometric deficiency of preferably aromatic diepoxide, and then reacting the product containing less than -0.3 part of unreacted dihydric phenolic compound per part of reaction product with at least about 3.25 mol of formaldehyde per mol of said reaction product and with monosecondary amine to produce a Mannich base. This Mannich base is then reacted with additional diepoxide in an amount of from 0.5 to 2 epoxy equivalents per epoxy equivalent in the initially used diepoxide. ## Claims ### Claim 1 An amine resin which is soluble in water with the aid of an acid, produced by reacting a dihydric phenolic compound with diepoxide having a 1,2-epoxy equivalency of at least about 1.4 and providing from 0.3 to 0.6 equivalents of epoxide in said diepoxide per equivalent of phenolic OH in said phenolic compound, and then reacting the reaction product containing less than 0.3 part of unreacted dihydric phenolic compound per part of said reaction product with at least about 3.25 mols of formaldehyde per mol of reaction product and with monosecondary amine to produce Mannich base groups, and then reacting with additional diepoxide in an amount of from 0.5 to 2 epoxy equivalents per epoxy equivalent in the initially used diepoxide. ### Claim 2 (depends on 1) An amine resin as recited in claim 1 in which said dihydric phenolic compound is a bisphenol and said diepoxide is aromatic. ### Claim 3 (depends on 2) An amine resin as recited in claim 2 in which more than 3.5 moles of formaldehyde are used per mol of starting bisphenol. ### Claim 4 (depends on 3) An amine resin as recited in claim 3 in which the only unreacted bisphenol present during the reaction with formaldehyde and monosecondary amine is that which was present during the reaction with aromatic diepoxide. ### Claim 5 (depends on 2) An amine resin as recited in claim 2 in which a diglycidyl ether of a bisphenol having a molecular weight of about 350 to about 5000 is reacted with a bisphenol in an amount of 0.3 to 0.6 equivalents of epoxide in said diglycidyl ether per equivalent of phenolic OH in said bisphenol. ### Claim 6 (depends on 5) An amine resin as recited in claim 5 in which said monosecondary amine component is a mixture of C.sub.1 -C.sub.8 dialkyl amine and diethanol amine. ### Claim 7 An amine resin which is soluble in water with the aid of an acid produced by reacting a bisphenol with a diglycidyl ether of a bisphenol having a molecular weight in the range of 350 to 600 in an amount of 0.3 to 0.6 equivalents of epoxide per equivalent of phenolic OH in said bisphenol, then reacting the product containing less than 0.3 part of unreacted bisphenol per part of said reaction product with more than 3.5 moles of formaldehyde per mol of starting bisphenol to solubilize the formaldehyde, and then reacting with a mixture of C.sub.1 -C.sub.8 dialkyl amine and diethanol amine to produce a Mannich base, and then reacting with additional diepoxide in an amount of from 1 to 1.5 epoxy equivalents per epoxy equivalent in the initially used diglycidyl ether. ### Claim 8 (depends on 1) A amine resin as recited in claim 1 dispersed in water with the aid of an acid to provide a bath having a pH in the range of 5-9. ### Claim 9 (depends on 8) A water dispersion as recited in claim 8 in which an aminoplast or phenoplast resin is present in admixture with said amine resin to enhance the cure thereof. ### Claim 10 (depends on 7) An amine resin as recited in claim 7 dispersed in water with the aid of an acid to provide a bath having a pH in the range of 6-8.5, said amine resin being in admixture with an aminoplast resin.