# US 11,306,218 B2 · Container coating system > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,306,218 B2 - Document ID: US11306218B2 - Status: Granted - Kind: B2 - Application number: 16/713,764 - Filed: 2019-12-13 - Published: 2020-04-16 - Granted: 2022-04-19 - Earliest claimed: 2012-08-09 - Assignees: Swimc LLC - Applicants: Swimc LLC - Inventors: Jeffrey Niederst; Richard H. Evans; Robert M. O'Brien; Kevin Romagnoli; Mark S. Von Maier; Mary E. Tishey; Gregory M. Paulson - Web page: https://patentgrep.com/patent/US11306218B2 ## CPC - C09D 127/06: Homopolymers or copolymers of vinyl chloride - 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}) - B65D 85/70: {for materials not otherwise provided for} - C08G 59/063: {with epihalohydrins} - C08G 59/066: {with chain extension or advancing agents} - C08G 65/485: {Polyphenylene oxides} - C09D 5/002: {Priming paints (C09D5/08 takes precedence)} - C09D 5/08: Anti-corrosive paints - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - 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 - C09D 171/00: Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers - C09D 171/12: Polyphenylene oxides - B05D 7/227: {of containers, cans or the like} - B05D 7/544: {the first layer is let to dry at least partially before applying the second layer} - B05D 2202/00: Metallic substrate - C08G 2650/56: Polyhydroxyethers, e.g. phenoxy resins - Y10T 428/1379: Contains vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit - Y10T 428/31786: Of polyester [e.g., alkyd, etc.] - 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) - 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 - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A multi-coat coating system having an undercoat composition and an overcoat composition, wherein the undercoat, overcoat or both the undercoat and overcoat contain a polymer having segments of a specified formula and are substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S. The coating system is suitable for use on a food-contact surface of food or beverage containers. ## Claims ### Claim 1 A multi-coat coating system comprising: an undercoat composition comprising: a polymer having two or more aryl or heteroaryl groups joined by a linking group having a molecular weight of about 125 Daltons to about 500 Daltons; and an overcoat composition comprising at least one thermoplastic material or a polyester polymer, wherein the polymer is derived from polyhydric phenols having a logarithmic Relative Proliferative Effect (RPE) of −2 or less. ### Claim 2 (depends on 1) The multi-coat coating system according to claim 1, wherein the polymer of the undercoat composition has one or more segments of the below Formula IA: wherein: i. H denotes a hydrogen atom, if present; ii. each R1 is independently an atom or group having an atomic weight of at least 15 Daltons; iii. v is independently 0 to 4; iv. w is 4; v. n is 1; vi. R2 is the linking group having a molecular weight of about 125 Daltons to about 500 Daltons; and vii. two or more R1 or R2 groups can join to form one or more cyclic groups. ### Claim 3 (depends on 2) The multi-coat coating system according to claim 2, wherein R2 has a molecular weight of at least 150 Daltons. ### Claim 4 (depends on 2) The multi-coat coating system according to claim 2, wherein R2 is a polar linking group. ### Claim 5 (depends on 4) The multi-coat coating system according to claim 4, wherein R2 includes one or more ketone, carboxyl, carbonate, hydroxyl, phosphate, or sulfoxide groups. ### Claim 6 (depends on 2) The multi-coat coating system according to claim 2, wherein R2 is a polar linking group and includes at least one aryl or heteroaryl group. ### Claim 7 (depends on 2) The multi-coat coating system according to claim 2, wherein R2 is a polar linking group and includes at least one cyclic group. ### Claim 8 (depends on 2) The multi-coat coating system according to claim 2, wherein for at least one of the phenylene rings depicted in Formula IA, v is 1 to 4. ### Claim 9 (depends on 2) The multi-coat coating system according to claim 2, wherein for at least one of the phenylene rings depicted in Formula IA, v is 1 to 4 and at least one R1 is attached to the ring at an ortho or meta position relative to the oxygen atom depicted in Formula IA. ### Claim 10 (depends on 2) The multi-coat coating system according to claim 2, wherein the segments of Formula IA are derived from at least one of the diglycidyl ether of 2,2-bis(4-hydroxyphenyl)propanoic acid, the diglycidyl ether of 4,4′,4″-(ethane-1,1,1-triyl)triphenol, or the diglycidyl ether of 4,4′-(1,4-phenylenebis(propane-2,2-diyl))polyhydric phenol. ### Claim 11 (depends on 2) The multi-coat coating system according to claim 2, wherein the segments of Formula IA are derived from one or more of: ### Claim 12 (depends on 1) The multi-coat coating system according to claim 1, wherein the undercoat composition comprises a non-aqueous liquid carrier. ### Claim 13 (depends on 1) The multi-coat coating system according to claim 1, wherein the multi-coat coating system is substantially free of polyhydric phenols that exhibit an RPE logarithmic value of greater than about −3.0. ### Claim 14 (depends on 1) The multi-coat coating system according to claim 1, wherein the multi-coat coating system is substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of 4,4′-(ethane-1,2-diyl)bis(2,6-dimethylphenol). ### Claim 15 (depends on 1) The multi-coat coating system according to claim 1, wherein the multi-coat coating system is substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of 4,4′,4″(ethane-1,1,1-triyl)triphenol. ### Claim 16 (depends on 1) The multi-coat coating system according to claim 1, wherein the polymer is derived from reactants including a polyhydric phenol and a non-bisphenol diepoxide. ### Claim 17 (depends on 16) The multi-coat coating system according to claim 16, wherein the non-bisphenol diepoxide comprises an aliphatic or cycloaliphatic diepoxide. ### Claim 18 (depends on 17) The multi-coat coating system according to claim 17, wherein the non-bisphenol diepoxide is at least one of 1,4-cyclohexanedimethanol diglycidyl ether, neopentyl glycol diglycidyl ether, 2-methy-1,3-propanediol diglycidyl ether, or tricyclodecane dimethanol diglycidyl ether. ### Claim 19 (depends on 16) The multi-coat coating system according to claim 16, wherein the polyhydric phenol is at least one of catechol, substituted catechol, hydroquinone, substituted hydroquinone, resorcinol, or substituted resorcinol. ### Claim 20 (depends on 1) The multi-coat coating system according to claim 1, wherein the overcoat comprises a thermoplastic material, and wherein the thermoplastic material comprises polyvinyl chloride, an organosol, or plastisol. ### Claim 21 (depends on 20) The multi-coat coating system according to claim 20, wherein the thermoplastic material is dispersed in a liquid carrier. ### Claim 22 (depends on 21) The multi-coat coating system according to claim 21, wherein the liquid carrier is non-aqueous. ### Claim 23 (depends on 1) The multi-coat coating system according to claim 1, wherein the overcoat comprises a polyester polymer. ### Claim 24 (depends on 1) The multi-coat coating system according to claim 1, wherein the overcoat comprises at least 30 present by weight of the polyester polymer or the thermoplastic material. ### Claim 25 (depends on 1) The multi-coat coating system according to claim 1, wherein the polymer constitutes at least 30 present by weight of the undercoat composition based on the total weight of resin solids in the undercoat composition. ### Claim 26 An article comprising: a container, or a portion thereof, comprising a metal substrate; and a multi-coat coating system applied on at least a portion of the metal substrate, the multi-coat coating system comprising: an undercoat composition comprising a polymer having two or more aryl or heteroaryl groups joined by a linking group having a molecular weight of about 125 Daltons to about 500 Daltons; and an overcoat composition comprising at least one thermoplastic material or a polyester polymer, wherein the polymer is derived from polyhydric phenols having a logarithmic Relative Proliferative Effect (RPE) of −2 or less. ### Claim 27 (depends on 26) The article according to claim 26, wherein the polymer of the undercoat composition comprising has one or more segments of the below Formula IA: wherein: i. H denotes a hydrogen atom, if present; ii. each R1 is independently an atom or group having an atomic weight of at least 15 Daltons; iii. v is independently 0 to 4; iv. w is 4; v. n is 1; vi. R2 is the linking group having a molecular weight of about 125 Daltons to about 500 Daltons; and vii. two or more R1 or R2 groups can join to form one or more cyclic groups. ### Claim 28 (depends on 26) The article according to claim 26, wherein the container comprises a food or beverage container. ### Claim 29 (depends on 28) The article according to claim 28, wherein the undercoat is on a food-contact surface of the food or beverage container. ### Claim 30 (depends on 26) The article according to claim 26, wherein the container or a portion thereof comprises a closure for a food or beverage container, wherein the closure is an easy open closure with at least a portion of an interior surface of the easy open closure coated with the multi-coat coating system. ### Claim 31 (depends on 26) The article according to claim 26, wherein the container or a portion thereof comprises a closure for a food or beverage container, wherein the closure is twist off closure with at least a portion of an interior surface of the twist off closure coated with the multi-coat coating system. ### Claim 32 A method comprising: applying an undercoat composition on at least a portion of a metal substrate prior to or after forming the metal substrate into a container; drying or at least partially curing the undercoat composition; and applying and curing an overcoat composition on the undercoat composition to produce a cured multi-coat coating adhered to the metal substrate, wherein the undercoat composition comprises a polymer having two or more aryl or heteroaryl groups joined by a linking group having a molecular weight of about 125 Daltons to about 500 Daltons, wherein the overcoat composition comprises at least one thermoplastic material or a polyester polymer, and wherein the polymer is derived from polyhydric phenols having a logarithmic Relative Proliferative Effect (RPE) of −2 or less.