Solvent-based coating compositions

Patent metadata

Field	Value
Publication number	US-9273226-B2
Application number	US-201214366029-A
Country	US
Kind code	B2
Filing date	Dec 18, 2012
Priority date	Dec 21, 2011
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

Coating compositions are disclosed. In some embodiments, the coating compositions are used to coat substrates such as packaging materials and the like for the storage of food and beverages. The coating compositions can be prepared by reacting an epoxidized vegetable oil and a hydroxyl functional material in the presence of an acid catalyst to form a hydroxyl functional oil polyol, mixing the hydroxyl functional oil polyol (with or without epoxidized polybutadiene) with a functional polyolefin copolymer to form a mixture, reacting the mixture with an ethylenically unsaturated monomer component in the presence of an initiator to form a graft copolymer, and crosslinking the graft copolymer with a crosslinker to form the coating composition.

First claim

What is claimed is:

1. A method for preparing a coating composition, the method comprising:
a) reacting an epoxidized vegetable oil with a hydroxyl functional material in the presence of an acid catalyst to form a hydroxyl functional oil polyol;
b) mixing the hydroxyl functional oil polyol with a functional polyolefin copolymer to form a mixture;
c) reacting the mixture with an ethylenically unsaturated monomer component in the presence of an initiator to form a graft copolymer; and
d) mixing the graft copolymer with a crosslinker to form the coating composition.

2. The method of claim 1 , wherein the epoxidized vegetable oil is derived from an unsaturated fatty acid glyceride.

3. The method of claim 1 , wherein the hydroxyl functional material is at least one of propylene glycol, 1,3-propane diol, ethylene glycol, neopentyl glycol, trimethylol propane, diethylene glycol, a polyether glycol, benzyl alcohol, 2-ethyl hexanol, a polyester, a polycarbonate, or a hydroxyl functional polyolefin.

4. The method of claim 1 , wherein the hydroxyl functional material is present in an amount of from about 1 to about 95 parts of the epoxidized vegetable oil.

5. The method of claim 1 , wherein the weight ratio of the hydroxyl functional oil polyol to the functional polyolefin copolymer is from about 80:20 to about 20:80 based on total solids.

6. The method of claim 1 , wherein the acid catalyst includes at least one of a sulfonic acid, a triflic acid, or a triflate salt of a metal of Group IIA, IIB, IIIA, IIIB or VIIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention).

7. The method of claim 1 , wherein the weight ratio of the ethylenically unsaturated monomer component to the hydroxyl functional oil polyol to functional polyolefin copolymer is from about 10:60:30 to about 80:10:10.

8. The method of claim 1 , wherein mixing the hydroxyl functional oil polyol and the functional polyolefin copolymer includes reacting the hydroxyl functional oil polyol with the functional polyolefin and epoxidized polybutadiene.

9. The method of claim 8 , wherein the weight ratio of the hydroxyl functional oil polyol to the functional polyolefin copolymer to the epoxidized polybutadiene is from about 50:40:10 to about 89:10:1.

10. The method of claim 8 , wherein the weight ratio of the ethylenically unsaturated monomer component to the hydroxyl functional oil polyol to the functional polyolefin copolymer to the epoxidized polybutadiene is from about 70:19:10:1 to about 20:40:30:10.

11. The method of claim 1 , wherein the ethylenically unsaturated monomer component includes at least one of butyl acrylate, methyl methacrylate, styrene, benzyl methacrylate, hydroxy propyl methacrylate, hydroxy ethyl acrylate, glycidyl methacrylate, acrylic acid, methacrylic acid, acetoacetoxy ethyl methacrylate, or a phosphate ester monomethacrylate.

12. The method of claim 1 , wherein the initiator is at least one of t-butyl peroxy benzoate or t-butyl peroctoate, dibenzoyl peroxide, 1,1,3,3-tetramethylbutyl-peroxy-2-ethylhexanoate.

13. The method of claim 1 , wherein the initiator is present in an amount from about 0.1 to about 15 wt % of the ethylenically unsaturated monomer component.

14. The method of claim 1 , wherein the solvent comprises up to about 90% based on the total weight of the reaction mixture.

15. The method of claim 1 , wherein the crosslinker includes at least one of phenol-formaldehyde, melamine formaldehyde, urea formaldehyde, benzoguanamine formaldehyde, an isocyanate, a blocked isocyanate, a bisphenol-A free epoxide, a phenolic crosslinker, a glycidyl(meth)acrylate copolymer, epoxidized sorbitol, benzoguanamine, or glycoluril.

16. The method of claim 1 , wherein the functional polyolefin copolymer is at least one of a copolymer of ethylene and methacrylic acid, a copolymer of ethylene and acrylic acid, a copolymer of ethylene and maleic anhydride, or a copolymer of propylene and maleic anhydride.

17. The method of claim 1 , further comprising inverting the graft copolymer into water.

18. The method of claim 1 , wherein reacting the epoxidized vegetable oil with the hydroxyl functional material in the presence of an acid catalyst includes reacting the epoxidized vegetable oil with the hydroxyl functional material in the presence of an acid catalyst and a solvent.

19. A substrate coated by spray coating or roll coating thereon a coating composition prepared by the method of claim 1 .

Assignees

• Akzo Nobel Coatings Int Bv

Inventors

• Li Cathy
• Memmer Timothy I
• Bode Daniel
• Posakiwsky Stefan

Classifications

• C08L91/00

  Compositions of oils, fats or waxes; Compositions of derivatives thereof · CPC title

• C08F289/00 Primary

  Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00 · CPC title

• C09D191/00 Primary

  Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof (polishing compositions, ski waxes C09G) · CPC title

• C09D151/08

  grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C09D163/00 Primary

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title