Outdoor weatherable photopolymerizable coatings

• US 6,974,850 B2
• Filed: 05/30/2003
• Issued: 12/13/2005
• Est. Priority Date: 05/30/2003
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Goenner, Emily S., Nelson, Eric W., Jones, Clinton L., Johnson, Stephen A., McMan, Steven J.
• Primary Examiner(s): Wu, David W.
• Assistant Examiner(s): Sastri, Satya B
• Application Number:
  US10/448,895
• Publication Number:
  US 20040242735A1
• Time in Patent Office: 928 Days
• Field of Search: 524/556, 524/91, 524/492, 524/558, 524/559, 548/259, 428/411.1
• US Class Current: 524/556
• CPC Class Codes: C08J 2375/04 Polyurethanes
• CPC Class Codes: C08J 2433/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
• CPC Class Codes: C08J 7/042 with two or more layers, where at least one layer of a composition contains a polymer binder
• CPC Class Codes: C08J 7/043 Improving the adhesiveness of the coatings per se, e.g. forming primers adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds
• 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
• CPC Class Codes: G02B 5/0808 having a single reflecting layer G02B5/0883, G02B5/0891 take precedence
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]

Abstract

Plastic articles can be coated with polymerizable compositions containing a vinyl-functional crosslinkable film former, a large amount of benzotriazole and a copolymerizable monomer that solubilizes the benzotriazole. The cured compositions help protect the article from UV exposure and other weathering effects.

Claims

1. A homogeneous coating composition comprising:

a) at least one vinyl-functional crosslinkable film former;

b) more than 15 weight percent benzotriazole UV absorber; and

c) at least one copolymerizable monomer that solubilizes the benzotriazole.

2. A composition according to claim 1 wherein the film former comprises a di-, tri- or higher functional acrylate or methacrylate.

3. A composition according to claim 1 wherein the film former comprises butanediol diacrylate.

4. A composition according to claim 1 wherein the film former comprises hexanediol diacrylate, butanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate or trimethylolpropane triacrylate.

5. A composition according to claim 1 wherein the film former contains urethane functionality.

6. A composition according to claim 1 wherein the benzotriazole is substituted in the 5-position of the benzo ring by a thio ether, alkyl sulfonyl or phenyl sulfonyl moiety.

7. A composition according to claim 1 wherein the benzotriazole is substituted in the 5-position of the benzo ring by an electron withdrawing group.

8. A composition according to claim 1 wherein the benzotriazole comprises 2-(2-hydroxy-3,5-di-tert-amyl-phenyl)-2H-benzotriazole.

9. A composition according to claim 1 wherein the benzotriazole comprises 2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole.

10. A composition according to claim 1 wherein the benzotriazole comprises 5-trifluoromethyl-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole.

11. A composition according to claim 1 wherein the monomer comprises isooctyl acrylate, 2-ethylhexyl acrylate, t-butyl acrylate, glycidyl methacrylate, benzyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylcyclohexyl acrylate, cyclohexyl acrylate, n-octyldecyl acrylate, butanediol diacrylate, 1-adamantyl acrylate, dicyclopentenyl acrylate or n-vinyl caprolactam.

12. A composition according to claim 1 wherein the monomer comprises isobornyl acrylate.

14. A composition according to claim 1 wherein the film former and monomer are chemically distinct species.

15. A composition according to claim 1 wherein the film former and monomer are the same species.

16. A composition according to claim 1 comprising about 16 to about 35 weight percent benzotriazole based on the total weight of solids in the composition.

17. A composition according to claim 1 comprising about 20 to about 35 weight percent benzothiazole based on the total weight of solids in the composition.

18. A composition according to claim 1 comprising about 21 to about 35 weight percent benzotriazole based on the total weight of solids in the composition.

19. A composition according to claim 1 further comprising submicron inorganic particles.

13. A homogeneous coating composition comprising:

(a) at least one vinyl-functional crosslinkable film former;

(b) more than 15 weight percent benzotriazole UV absorber; and

(c) at least one copolymerizable monomer that solubilizes the benzotriazole wherein the monomer comprises t-butylcyclohexyl acrylate.