Food or beverage containers coated with polymers of di(amido(alkyl)phenol) compounds

• US 10,526,277 B2
• Filed: 10/16/2014
• Issued: 01/07/2020
• Est. Priority Date: 10/17/2013
• Status: Active Grant

• Current Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Original Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Inventors: Gibanel, Sebastien, Prouvost, Benoit, Boutevin, Bernard
• Primary Examiner(s): Khatri, Prashant J
• Assistant Examiner(s): Davis, Zachary M
• Application Number:
  US15/029,439
• Publication Number:
  US 20160272576A1
• Time in Patent Office: 1,909 Days
• CPC Class Codes: B65D 85/72 for edible or potable liquids, semiliquids, or plastic or pasty materials
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C07C 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 235/50 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C08G 2650/50 containing nitrogen, e.g. polyetheramines or Jeffamines(r)
• CPC Class Codes: C08G 63/685 containing nitrogen
• CPC Class Codes: C08G 64/1641 containing nitrogen
• CPC Class Codes: C08G 65/3317 phenolic
• CPC Class Codes: C08G 65/3326 aromatic
• CPC Class Codes: C08G 65/40 from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
• CPC Class Codes: C08G 71/04 Polyurethanes
• CPC Class Codes: 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
• CPC Class Codes: C09D 169/00 Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
• CPC Class Codes: 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
• CPC Class Codes: C09D 171/02 Polyalkylene oxides
• CPC Class Codes: C09D 171/08 Polyethers derived from hydroxy compounds or from their metallic derivatives C09D171/02 takes precedence
• CPC Class Codes: C09D 175/12 from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group

Abstract

Di(amido(alkyl)phenol) compounds and upgraded molecular weight polymers made from such compounds have particular utility in coating compositions, especially for use on food and beverage contact substrates that are formed into or will be formed into containers or container components.

Claims

1. An article comprising:

a. a food or beverage packaging container, or portion thereof, having a food or beverage contact surface comprising a metal substrate; and

b. a coating formed from a coating composition disposed in powdered form on the food or beverage contact surface;

the coating composition comprising a polymer made from an α

, Ω

telechelic di(amido(alkyl)phenol) and a material that reacts with hydroxyl groups on phenol rings, and being substantially free of bisphenol A and bisphenol F, and wherein the polymer is a polyester, polyurethane, polycarbonate or phenolic resin.

2. The article according to claim 1, wherein the material that reacts with hydroxyl groups on phenol rings is an epoxide.

3. The article according claim 2, wherein the material that reacts with hydroxyl groups on phenol rings is epichlorohydrin.

4. The article according to claim 2, wherein the epoxide is a diepoxide and the polymer includes —

CH₂—

CH(OH)—

CH₂—

or —

CH₂—

CH₂—

CH(OH)—

segments.

5. The article according to claim 1, wherein the polymer is an epoxy-terminated or phenoxy-terminated polyether.

6. The article according to claim 1, wherein the polymer has air oxidizable unsaturated groups.

7. The article according to claim 1, wherein the polymer is free radically curable.

8. The article according to claim 1, wherein the coating composition further comprises a lubricant that facilitates manufacture of fabricated metal articles by imparting lubricity to the coated metal substrate, a pigment, a curing agent and a catalyst to increase the rate of cure.

9. The article according to claim 1, wherein the food or beverage packaging container comprises a two-piece drawn food can, a three-piece food can, a food can end, a drawn and ironed food or beverage can, a beverage can end, an easy open can end, or a twist-off closure lid.

10. An article comprising:

a. a food or beverage packaging container, or portion thereof, having a food or beverage contact surface comprising a metal substrate; and

b. a coating formed from a coating composition disposed in liquid or powdered form on the food or beverage contact surface;

the coating composition comprising a polymer made from a polyphenol and a material that reacts with hydroxyl groups on phenol rings, and wherein the polyphenol has the formula;

11. The article according to claim 10, wherein the polyphenol has Formula I.

12. The article according to claim 10, wherein the polyphenol has Formula II.

13. The article according to claim 10, wherein x and y are 1 and R¹ and R⁵ are hydrogen.

14. The article according to claim 10, wherein R³ is a divalent linear aliphatic group.

15. The article according to claim 10, wherein the polymer is made from a para-cresol-terminated diamide of Formula I having the formula:

16. The article according to claim 10, wherein the coating composition further comprises a lubricant that facilitates manufacture of fabricated metal articles by imparting lubricity to the coated metal substrate, a pigment, a curing agent and a catalyst to increase the rate of cure.

17. The article according to claim 10, wherein the food or beverage packaging container comprises a two-piece drawn food can, a three-piece food can, a food can end, a drawn and ironed food or beverage can, a beverage can end, an easy open can end, or twist-off closure lid.

18. The article according to claim 10, wherein the coating composition comprises the polymer in the liquid carrier, and wherein the liquid carrier comprises one or more organic solvents.

19. The article according to claim 10, wherein the coating composition comprises the polymer in the liquid carrier, and wherein the liquid carrier comprises water.

20. The article according to claim 10, wherein the coating composition is in powdered form.

21. The article according to claim 10, wherein the coating composition is substantially free of bisphenol A and bisphenol F.

22. A method for making a coated food or beverage packaging container, the method comprising:

applying to a food or beverage contact surface of a metal substrate a liquid or powdered coating composition comprising a polymer made from a polyphenol and a material that reacts with hydroxyl groups on phenol rings, wherein the polyphenol has the formula;