Synergistic catalyst combination for the preparation of radiation curable oligomers

Patent metadata

Field	Value
Publication number	US-9493674-B2
Application number	US-201514837946-A
Country	US
Kind code	B2
Filing date	Aug 27, 2015
Priority date	Mar 12, 2013
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

Radiation curable 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 may have a (meth)acrylate functional polyether polyol prepared by reacting an epoxidized vegetable oil in the presence of a phosphoric acid compound to form an epoxy phosphate, and reacting the epoxy phosphate with a hydroxyl functional (meth)acrylate in the presence of an acid catalyst to form the (meth)acrylate functional polyether polyol.

First claim

What is claimed is:

1. A radiation curable coating composition comprising a (meth)acrylate functional polyether polyol that is an acid catalyzed reaction product of an epoxy phosphate and a hydroxyl functional (meth)acrylate, wherein the epoxy phosphate is a reaction product of an epoxidized vegetable oil and a phosphoric acid compound.

2. The coating composition of claim 1 , wherein the epoxy phosphate is formed in the presence of a hydroxyl functional material.

3. The coating composition of claim 1 , wherein the hydroxyl functional (meth)acrylate is blended with a hydroxyl functional material.

4. The coating composition of claim 1 , wherein the acid catalyst is at least one of a triflic acid, 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), or a mixture of the triflate salts.

5. The coating composition of claim 1 , wherein the hydroxyl functional (meth)acrylate is at least one of 4-hydroxy butyl (meth)acrylate, hydroxy ethyl (meth)acrylate, or hydroxyl propyl (meth)acrylate.

6. The coating composition of claim 1 , wherein the phosphoric acid compound is at least one of phosphoric acid, super phosphoric acid, or an aqueous solution of the foregoing.

7. The coating composition of claim 1 , wherein the phosphoric acid compound is present in an amount from about 0.001 to about 25 wt % of the (meth)acrylate functional polyether polyol.

8. A method of forming a (meth)acrylate functional polyether polyol, the method comprising:
a) reacting an epoxidized vegetable oil with a phosphoric acid compound to form an epoxy phosphate; and
b) reacting the epoxy phosphate with a hydroxyl functional (meth)acrylate in the presence of an acid catalyst to form a (meth)acrylate functional polyether polyol.

9. The method of claim 8 , wherein the epoxy phosphate is formed in the presence of a hydroxyl functional material.

10. The method of claim 8 , wherein the hydroxyl functional (meth)acrylate is blended with a hydroxyl functional material.

11. The method of claim 8 , wherein the acid catalyst is at least one of a triflic acid, 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), or a mixture of the triflates salts.

12. The method of claim 8 , wherein the hydroxyl functional (meth)acrylate is at least one of 4-hydroxy butyl (meth)acrylate, hydroxy ethyl (meth)acrylate, or hydroxyl propyl (meth)acrylate.

13. The method of claim 8 , wherein the phosphoric acid compound is at least one of phosphoric acid, super phosphoric acid, or an aqueous solution of the foregoing.

14. The method of claim 8 , wherein the phosphoric acid compound is present in an amount from about 0.01 to about 25 wt % of the (meth)acrylate functional polyether polyol.

15. A substrate coated with the coating composition of claim 1 .

16. A radiation curable coating composition including the (meth)acrylate functional polyether polyol of claim 8 .

17. A method of coating a substrate comprising the steps of:
a) applying the coating composition of claim 1 to the substrate; and
b) curing the coating composition with electron beam or ultraviolet radiation.

18. A substrate coated with the coating composition of claim 1 .

Assignees

• Akzo Nobel Coatings Int Bv

Inventors

• Craun Gary Pierce
• Pompignano Gary Charles

Classifications

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08L2312/06

  by radiation · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• C09D193/00

  Coating compositions based on natural resins; Coating compositions based on derivatives thereof (based on polysaccharides C09D101/00 - C09D105/00; based on natural rubber C09D107/00; polishing compositions C09G) · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title