Radiation curable coating compositions

• US 10,407,573 B2
• Filed: 06/14/2010
• Issued: 09/10/2019
• Est. Priority Date: 06/12/2009
• Status: Active Grant

• Current Assignee: Axalta Coating Systems Ip Co Llc (Axalta Coating Systems Ltd.)
• Original Assignee: Axalta Coating Systems Ip Co Llc (Axalta Coating Systems Ltd.)
• Inventors: Loeffler, Helmut
• Primary Examiner(s): Roswell, Jessica M
• Application Number:
  US13/377,190
• Publication Number:
  US 20120083548A1
• Time in Patent Office: 3,375 Days
• Field of Search: 522 76, 522 18, 522 38, 522139-140
• CPC Class Codes: C09D 4/00 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

Abstract

This invention relates to coating compositions curable by radical polymerization by means of high energy radiation and by at least one additional chemical curing reaction, comprising:

• • A) at least one compound capable of free-radical polymerization having at least one olefinically unsaturated group,
  • B) at least one photoinitiator and
  • C) at least one organic phosphine derivative, preferably at least one triaryl phosphine, most preferred triphenyl phosphine.

Claims

1. A solvent-borne coating composition comprising:

A) at least one compound capable of free-radical polymerization having at least one olefinically unsaturated group comprising a (meth)acrylic acid ester group and at least one functional group a′

) comprising a hydroxyl group that is reactive towards at least one functional group b) of compound A1) and A3),

A1) at least one compound with at least one functional group b) comprising an isocyanate group curable by addition and/or condensation reaction, with the proviso that A1) is free of radically polymerizable olefinically unsaturated groups,

A2) at least one binder with at least one functional group a″

) comprising a thiol group that is reactive towards the at least one functional group b) of compound A1) and A3), with the proviso that A2) is free of radically polymerizable olefinically unsaturated groups,

A3) at least one further compound capable of free-radical polymerization having at least one olefinically unsaturated group comprising a (meth)acrylic acid ester group and at least one functional group b) comprising an isocyanate group that is reactive towards the at least one functional group a) of compound A) and A2), wherein A), A1), A2), and A3) are all present and are different components with respect to one another,

B) at least one photoinitiator, and

C) at least one organic phosphine derivative provided as triphenyl phosphine, with the proviso that the component B) is different from the component C), wherein the component C) is present in an amount from 0.5% to 45% by weight solids, based on the total amount of weight solids of components A) and A3), and wherein the coating composition is free of phosphites.

3. The coating composition of claim 1, wherein said composition is a clear coat composition or pigmented top coat composition of a multilayer coating.

4. The coating composition of claim 1, wherein the component B) comprises an acyl phosphine oxide.

5. The coating composition of claim 4, wherein the acyl phosphine oxide comprises diphenyl (2,4,6-trimethylbenzoyl)-phosphine oxide.

6. The coating composition of claim 5, wherein the component B) is present in an amount of from 0.4% to 3.0% by weight solids.

7. The coating composition of claim 6, wherein the component C) is present in an amount from 5.0% to 30% by weight solids, based on the total amount of weight solids of components A) and A3).

8. The coating composition of claim 7, consisting of components A), A1), A2), A3), B), and C), and optionally one or more of:

a solvent, a pigment, a flow control agent, an anti-settling agent, an adhesion promoting agent, and a light stabilizer.

2. A method, comprising:

1) providing or preparing a solvent-borne coating composition comprising;

A) at least one compound capable of free-radical polymerization having at least one olefinically unsaturated group comprising a (meth)acrylic acid ester group and at least one functional group a′

) comprising a hydroxyl group that is reactive towards at least one functional group b) of compound A1) and A3),

A1) at least one compound with at least one functional group b) comprising an isocyanate group curable by addition and/or condensation reaction, with the proviso that A1) is free of radically polymerizable olefinically unsaturated groups,

A2) at least one binder with at least one functional group a″

) comprising a thiol group that is reactive towards the at least one functional group b) of compound A1) and A3), with the proviso that A2) is free of radically polymerizable olefinically unsaturated groups,

A3) at least one further compound capable of free-radical polymerization having at least one olefinically unsaturated group comprising a (meth)acrylic acid ester group and at least one functional group b) comprising an isocyanate group that is reactive towards the at least one functional group a) of compound A) and A2), wherein A), A1), A2), and A3) are all present and are different components with respect to one another,

B) at least one photoinitiator, and

C) at least one organic phosphine derivative provided as triphenyl phosphine, with the proviso that the component B) is different from the component C), wherein the component C) is present in an amount from 0.5% to 45% by weight solids, based on the total amount of weight solids of components A) and A3), and wherein the coating composition is free of phosphites; and

2) using the coating composition as a clear coat composition or a pigmented top coat composition in a multilayer coating application to a substrate.