# US 10,767,000 B2 · BPA-free coatings > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,000 B2 - Document ID: US10767000B2 - Status: Granted - Kind: B2 - Application number: 15/565,616 - Filed: 2016-04-10 - Published: 2018-03-15 - Granted: 2020-09-08 - Earliest claimed: 2015-04-10 - Assignees: Battelle Memorial Institute - Applicants: Battelle Memorial Institute - Inventors: Ramanathan S. Lalgudi; Robert J. Cain - Web page: https://patentgrep.com/patent/US10767000B2 ## CPC - C08G 59/1455: {Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof} - B65D 23/02: Linings or internal coatings - B65D 25/14: Linings or internal coatings (of containers made by folding or erecting blanks made of paper B65D5/56 {; linings for domestic water storage heaters F24H1/183}) - C08G 59/32: Epoxy compounds containing three or more epoxy groups - C08G 65/3322: {acyclic} - C09D 177/00: Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain (based on polyhydrazides C09D179/06; based on polyamide-imides C09D179/08); Coating compositions based on derivatives of such polymers - C09D 179/02: Polyamines - B05D 7/14: to metal, e.g. car bodies (involving a chemical reaction between the metal and the coating C23) - B05D 7/227: {of containers, cans or the like} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B65D: CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES - 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) - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) ## Abstract Provided are poly(AAG)-compositions, and corresponding coatings, foams, and coated articles. Also provided are methods for preparing the poly(AAG)-compositions and corresponding reagents including. e.g., polyol-AAG compositions. Coatings using the poly(AAG)-compositions may be useful for, e.g., replacing bisphenol-A cross-linked coatings used in food and beverage containers, coating metal articles, and the like. ## Claims ### Claim 1 A method for preparing an acetoacetyl group (AAG) composition comprising: providing a poly-functional compound comprising two or more functional groups, each functional group independently being hydroxy, amino, or alkenyl, at least a portion of the poly-functional compound being a polyol derived from one or more of a pyrolyzed bio-oil and an alkoxylated pyrolyzed bio-oil, provided that the poly-functional compound is not a triglyceride-derived oil; and reacting the poly-functional compound under conditions effective to form the AAG composition by one or more of: contacting the poly-functional compound with a ketene compound, wherein the poly-functional compound comprises at least one hydroxy group; contacting the poly-functional compound with a β-ketoester, wherein the poly-functional compound comprises at least one hydroxy or amino group; contacting the poly-functional compound with a peroxo reagent and one or more of: a β-ketoimide, a β-ketoester, and a β-ketoacid, wherein the poly-functional compound comprises at least one alkenyl group; and contacting the poly-functional compound with a mercaptoalkanol in the presence of an initiator effective to form a mercaptoalkanol-substituted compound; the poly-functional compound comprising at least one alkenyl group; and further reacting the mercaptoalkanol-substituted compound with one or more of: the β-ketoester and the β-ketoacid. ### Claim 2 (depends on 1) The method of claim 1, comprising conducting the method substantially in the absence of solvent. ### Claim 3 (depends on 1) The method of claim 1, one or more of the ketene compound: comprising one or more of: 4-methyleneoxetan-2-one, 4-ethylidene-3-methyloxetan-2-one, and 4-benzylidene-3-phenyloxetane-2-one; being derived from one or more of: an α-diazo ketone and an α-halo acyl halide; and being optionally substituted with one or more of: C1-C8 alkyl and C6-C10 aryl. ### Claim 4 (depends on 1) The method of claim 1, the β-ketoester being represented by Formula XIV: wherein: R″ is C1-C8 alkyl or C6-C10 aryl; R5 is C1-C8 alkyl, C2-C8 alkenyl, C6-C10 aryl, or C4-C8 heteroaryl, optionally substituted with —OH or —NH2; and R8 is H, C1-C8 alkyl, or C6-C10 aryl. ### Claim 5 (depends on 1) The method of claim 1, the β-ketomide being represented by one of: wherein: R5 is optionally hydroxylated C1-C8 alkyl, C2-C8 alkenyl, C6-C10 aryl, or C4-C8 heteroaryl; R9 is C1-C8 alkyl or C6 aryl optionally substituted with one or more of: nitro, carbonyl, haloalkyl, and halogen; and R10 is a C2-C6 alkyl, C3-C5 heteroaryl, or C6 aryl optionally substituted with one or more of: nitro, carbonyl, halogen, and haloalkyl. ### Claim 6 (depends on 1) The method of claim 1, the β-ketoacid being represented by Formula III: wherein: R5 is optionally hydroxylated C1-C8 alkyl, C2-C8 alkenyl, C6-C10 aryl, or C4-C10 heteroaryl; and R8 is H, or optionally hydroxylated C1-C8 alkyl or C6-C10 aryl. ### Claim 7 (depends on 1) The method of claim 1, wherein the poly-functional compound comprises an unsaturated non-triglyceride oil derived from a marine organism, a mammal, and an insect. ### Claim 8 (depends on 1) The method of claim 1, wherein the polyfunctional compound comprises a petroleum derived polyol, a petroleum-derived polyamine, a petroleum-derived polyalkene, or a composite or combination thereof.