Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom

Patent metadata

Field	Value
Publication number	US-10961344-B2
Application number	US-202016792428-A
Country	US
Kind code	B2
Filing date	Feb 17, 2020
Priority date	Apr 9, 2009
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

A polymer is provided that preferably includes at least one unsaturated cycloaliphatic group. In one embodiment, the polymer is combined with an optional crosslinker and an optional carrier to form a coating composition suitable for use in coating articles such as packaging articles. In one embodiment, the polymer has at least one unsaturated cycloaliphatic group that is at least bicyclic.

First claim

What is claimed is:

1. An article comprising:
a metal substrate of a food or beverage container or a portion thereof; and
a coating applied on at least a portion of a major surface of the metal substrate, wherein the coating is formed from a coating composition comprising: a water-dispersible polyester polymer obtained by grafting acid-functional ethylenically unsaturated monomers to a polyester polymer;
the polyester polymer formed from reactants that include one or more polycarboxylic acid reactants and one or more polyol reactants, wherein the reactants include a dimer fatty acid and an unsaturated reactant having a reactive group capable of participating in a step-growth reaction; and
wherein the unsaturated reactants having a reactive group capable of participating in a step-growth reaction provide the grafting of the acid-functional ethylenically unsaturated monomers to the polyester polymer.

2. The article of claim 1 , wherein the water-dispersible polyester polymer comprises an aromatic polyester polymer that includes at least 5 weight percent of aromatic groups.

3. The article of claim 1 , further comprising a lubricant.

4. The article of claim 1 , wherein the article comprises a metal food or beverage can or portion thereof and the coating is applied to an interior surface.

5. The article of claim 1 , wherein the polyester polymer has a number average molecular weight of about 1,000 to about 20,000.

6. The article of claim 1 , wherein the polyester polymer has a hydroxyl number of about 5 to about 150 mg KOH/gram.

7. The article of claim 1 , wherein the polyester polymer has an acid number less than about 40 mg KOH/gram.

8. The article of claim 1 , wherein the water-dispersible polyester polymer is present in the coating composition in an amount greater than about 50 weight percent based on the total nonvolatile weight of the coating composition.

9. The article of claim 1 , wherein the coating composition further comprises a crosslinker selected from a resole phenolic crosslinker, amino crosslinkers, blocked isocyanate crosslinkers, epoxy-functional crosslinkers, or combinations thereof.

10. The article of claim 9 , wherein the crosslinker is a benzoguanamine-formaldehyde-based resin.

11. The article of claim 1 , wherein the unsaturated reactant of water-dispersible polyester polymer capable of participating in a step-growth reaction is maleic acid fumaric acid, nadic acid, methylnadic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, anhydride derivatives thereof, or combinations thereof.

12. The article of claim 11 , wherein the polyester polymer is formed from reactants including, based on resin solids, up to about 30 weight percent of the unsaturated reactant having a reactive group capable of participating in a step-growth reaction.

13. The article of claim 11 , wherein the unsaturated reactant capable of participating in a step-growth reaction is maleic anhydride.

14. The article of claim 1 , wherein the one or more polycarboxylic acid reactants include phthalic acid; isophthalic acid; terephthalic acid; tetrahydrophthalic acid; hexahydrophthalic acid; endomethylene tetrahydrophthalic acid; dimethylterephthalate; maleic acid; 2-methyl maleic acid; pyromellitic acid; adipic acid; succinic acid; sebacic acid; glutaric acid; methyleneglutaric acid; glutaconic acid; azelaic acid; aconitic acid; itaconic acid; 2-methyl itaconic acid; sebacic acid; lauric acid; fumaric acid; citraconic acid; 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid; muconic acid; mesaconic acid; camphoric acid; trimellitic acid; tricarballylic acid; tricarboxyethylene; dimethylolpropionic acid; beta-acryloxypropionic acid; esters and anhydrides of all the aforementioned acids and combinations thereof.

15. The article of claim 14 , wherein the polyester polymer is formed from reactants including, based on total resin solids, less than about 80 weight percent of the one or more polycarboxylic acids.

16. The article of claim 1 , wherein the one or more polyol reactants include one or more of ethylene glycol; polyethylene glycol; diethylene glycol; triethyleneglycol; tetraethyleneglycol; hexaethyleneglycol; neopentyl glycol; 1,3- or 1,2-propyleneglycol; polypropylene glycol; 1,4-butanediol; 1,5-pentanediol; 2,2-dimethyl propanediol; 1,6-hexanediol; 1,2-cyclohexanediol; 1,4-cyclohexanedimethanol; trimethylol propane; pentaerythritol; tricyclodecane dimethanol; glycerol; or combinations thereof.

17. The article of claim 16 , wherein the polyester polymer is formed from reactants including, based on resin solids, at least about 20 weight percent of the one or more polyol reactants.

18. The article of claim 1 , wherein the acid-functional ethylenically unsaturated monomers include ethylenically unsaturated mono- or multi-functional acids(s) selected from (meth)acrylic acid; vinylsulfonic acid; crotonic acid; alpha,beta-ethylenically unsaturated carboxylic acids such as maleic acid, 2-methyl maleic acid, fumaric acid, itaconic acid, and 2-methyl itaconic acid; alpha-chloroacrylic acid; alpha-cyano acrylic acid; alpha-phenylacrylic acid; beta-stearylacrylic acid; sorbic acid; alpha-chlorosorbic acid; angelic acid; cinnamic acid; p-chlorocinnamic acid; citraconic acid; mesaconic acid; aconitic acid; derivatives thereof, anhydrides thereof, or any combination thereof.

19. The article of claim 18 , wherein the polyester polymer is obtained from grafted monomers including up to about 40 weight percent of the acid-functional ethylenically unsaturated monomers based on the total weight of reactants allowed to react with the polyester polymer.

20. The article of claim 1 , wherein the one or more polycarboxylic acid reactants include isophthalic acid, hexahydrophthalic acid, anhydride derivatives thereof, and combinations thereof and wherein the one or more polyol reactants include cyclohexane dimethanol, trimethylol propane, propane diol, derivatives thereof, and combinations thereof.

21. The article of claim 20 , wherein the acid-functional ethylenically unsaturated monomers include (meth)acrylic acid, alkyl (meth)acrylates, hydroxyalkyl (meth)acrylates, derivatives thereof, and combinations thereof.

22. The article of claim 1 , wherein at least a portion of acid-functional groups on the acid-functional ethylenically unsaturated monomers are neutralized with a base.

23. The article of claim 22 , wherein the base is selected from trimethyl amine, dimethyl ethanol amine, methyl diethanol amine, triethanolamine, ethyl methyl ethanol amine, dimethyl ethyl amine, dimethyl propyl amine, dimethyl 3-hydroxy-1-propyl amine, dimethylbenzyl amine, dimethyl 2-hydroxy-1-propyl amine, diethyl methyl amine, dimethyl 1-hydroxy-2-propyl amine, triethyl amine, tributyl amine, N-methyl morpholine, or combinations thereof.

Assignees

• Sherwin Williams Co

Inventors

• Skillman Charles
• Share Paul E
• Paulson Greg
• Evans Richard H
• Prouvost Benoit
• Stenson Paul
• Killilea T Howard
• Cavallin Carl L
• Hartinger Danny
• Brandenburger Larry B

Classifications

• B65D23/02 Primary

  Linings or internal coatings · CPC title

• B65D1/12

  Cans, casks, barrels, or drums · CPC title

• B05D1/00

  Processes for applying liquids or other fluent materials (B05D5/00, B05D7/00 take precedence) · CPC title

• C08L2203/10

  used for bottles · CPC title

• C08G63/553 Primary

  Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts · CPC title