Container coating compositions

• US 10,703,931 B2
• Filed: 02/09/2016
• Issued: 07/07/2020
• Est. Priority Date: 05/23/2011
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Seneker, Carl, Williamson, Jessica, Knotts, Claudia, Moussa, Youssef
• Primary Examiner(s): Higgins, Gerard
• Assistant Examiner(s): Ortman, Jr., Kevin C
• Application Number:
  US15/018,882
• Publication Number:
  US 20160160075A1
• Time in Patent Office: Days
• Field of Search: 428 358
• CPC Class Codes: C08G 63/54 the acids or hydroxy compounds containing carbocyclic rings
• CPC Class Codes: C08G 63/6928 Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C08L 85/02 containing phosphorus
• CPC Class Codes: C09D 167/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C09D167/06 takes precedence
• CPC Class Codes: C09D 167/06 Unsaturated polyesters having carbon-to-carbon unsaturation
• CPC Class Codes: C09D 5/00 Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced electrically insulating plastics, resins or waxes H01B3/30; Filling pastes
• CPC Class Codes: C09D 7/65 macromolecular C09D7/41-C09D7/48 take precedence
• CPC Class Codes: Y10T 428/1352 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

A coating composition comprising a polyester resin binder and a phosphatized polyester. The compositions are useful for coating containers such as food and beverage containers. The compositions have excellent hydrolytic stability upon storage at high temperature. The compositions are formulated to be substantially free of bisphenol A (BPA) and bisphenol A diglycidyl ether (BADGE).

Claims

1. A coated article comprising:

(a) a metal container for food or beverages,

(b) a cured coating applied to the interior surface of the container, the cured coating being derived from a liquid coating composition comprising;

(A) 70 to 90 percent by weight of a hydroxyl functional polyester resin prepared from;

(i) 1 to 8 mole percent of an alpha, beta-ethylenically unsaturated dicarboxylic acid containing from 4 to 5 carbon atoms,

(ii) 10 to 30 mole percent of naphthalene dicarboxylic acid including alkyl esters having 1-4 carbon atoms thereof,

(iii) 10 to 30 mole percent of an aromatic dicarboxylic acid different from (ii),

(iv) 40 to 60 mole percent of an aliphatic diol containing branched alkyl groups and being free of neopentyl glycol, and

(v) 0.2 to 4 mole percent of a triol,

the mole percentages being based on total moles of (i)-(v);

(B) 5 to 25 percent by weight of an aminoplast curing agent,

(C) 0.1 to 20 percent by weight of a phosphatized polyester,

(A), (B) and (C) being dissolved in organic solvent;

the percentages by weight of (A), (B) and (C) being based on weight of resin solids in the coating composition, wherein the hydroxyl functional polyester resin has a number average molecular weight of 9,000 to 16,000 g/mole.

2. The coated article of claim 1 in which (ii) is the alkyl ester of naphthalene dicarboxylic acid having 1-4 carbon atoms.

3. The coated article of claim 1 in which (iii) is selected from the group consisting of isophthalic acid and terephthalic acid.

4. The coated article of claim 1 in which (iv) is selected from the group consisting of 2-methyl-1,3-propanediol and 2-butyl-2-ethyl-1,3-propanediol.

5. The coated article of claim 1 in which (v) is trimethylolpropane.

6. The coated article of claim 1 further comprising up to 15 mole percent of a saturated aliphatic dicarboxylic acid containing from 4 to 12 carbon atoms.

7. The coated article of claim 1 further comprising up to 5 mole percent of a cycloaliphatic diol.

8. The coated article of claim 1 further comprising up to 15 mole percent of a linear diol.

9. The coated article of claim 1 in which the alpha, beta-ethylenically unsaturated dicarboxylic acid is maleic acid.

10. The coated article of claim 1 in which the hydroxyl functional polyester resin has a hydroxyl number less than 15.

11. The coated article of claim 1 in which the phosphatized polyester is the reaction product of a phosphorus acid with a hydroxyl functional polyester.

12. The coated article of claim 1 in which the phosphatized polyester is present in amounts of 3 to 12 percent by weight based on weight of resin solids.

13. The coated article of claim 1 in which the phosphatized polyester comprises a reaction product comprising:

(i) a polyester having an Mn of 2,000 to 5,000, a hydroxyl number of 20 to 75, and an acid value of 15 to 25;

the polyester comprising a polycondensate of;

(A) a polyol component comprising a mixture of diols and triols,

(B) a polyacid component comprising an alpha, beta-ethylenically unsaturated polycarboxylic acid, and

(ii) a phosphorus acid.

14. The coated article of claim 13 in which the polyol component comprises an aliphatic polyol optionally with alkyl branching.

15. The coated article of claim 13 in which the triol of the polyol component comprises trimethylolpropane.

16. The coated article of claim 13 in which the polyacid component comprises a mixture of an aliphatic and/or an aromatic polycarboxylic acid and an alpha, beta-ethylenically unsaturated polycarboxylic acid.

17. The coated article of claim 13 in which the alpha, beta-ethylenically unsaturated polycarboxylic acid of the polyacid component comprises maleic acid.

18. The coated article of claim 13 in which the phosphorus acid comprises phosphoric acid.

19. The coated article of claim 13 in which the phosphorus acid is used in amounts of 0.2 to 0.5 equivalents per equivalent of hydroxyl, that is, 0.2 to 0.5 P-OH for each hydroxyl.

20. The coated article of claim 1 in which the container is a can.

21. The coated article of claim 20 in which the coating composition is deposited on the interior walls of the can.

22. The coated article of claim 20 in which the interior surface of the container is a can end.

23. The coated article of claim 1 in which the coating composition (b) is substantially free of bisphenol A and derivatives thereof.

24. The coated article of claim 1 in which the coating composition (b) is completely free of bisphenol A and derivatives thereof.

25. The coated article of claim 1 in which the coating is cured by heating the metal to 205-255°

C. peak metal temperature for about 5 to 30 seconds.