Photocurable acrylic coating composition

• US 4,902,724 A
• Filed: 04/21/1989
• Issued: 02/20/1990
• Est. Priority Date: 12/22/1986
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Moore, James E.
• Primary Examiner(s): Jacobs, Lewis T.
• Assistant Examiner(s): BUTTNER, DAVID J
• Application Number:
  US07/342,607
• Time in Patent Office: 305 Days
• Field of Search: 522/42, 522/44, 522/78, 522/79, 522/75, 522/77, 522/40, 522/43
• US Class Current: 522/40
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/103 of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• 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 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• 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: C08J 7/18 using wave energy or particle radiation
• 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: Y10T 428/31507 Of polycarbonate

Abstract

A photocured acrylic coating comprised of the photoreaction products of:

(i) at least one photocurable polyfunctional acrylate monomer;

(ii) at least one acetophenone photoinitiator; and

(iii) at least one active ultraviolet radiation absorber selected from benzotriazoles, cyanoacrylate, and hydroxybenzophenones. The coating is substantially or completely cured and provides improved protection to the substrate against ultraviolet radiation.

Claims

1. An ultraviolet radiation curable coating composition for plastic substrates consisting of:

(i) at least one polyfunctional acrylate monomer represented by the formula ##STR13## wherein;

R³ is either a methyl radical or hydrogen;

R² is a c functional hydrocarbon residue, a c functional substituted hydrocarbon residue, a c functional hydrocarbon residue containing at least one ether linkage, or a c functional substituted hydrocarbon residue containing at least one ether linkage, said substituted hydrocarbon residue having from 1 to 4 substituent groups; and

c is an integer having a value of from 2 up to the number of replacable hydrogen atoms present on R² ;

(ii) at least one acetophenone photoinitiator present at a level selected from between about 0.05 to about 10 weight percent based on the total amounts of polyfunctional acrylate monomer and said photoinitiator present in said coating composition, said acetophenone photoinitiator being represented by the formula ##STR14## R⁴ being selected from lower alkyl radicals, R⁵ being selected from hydrogen and alkyl radicals, R⁶ being a --OR" radical wherein R" is selected from hydrogen and lower alkyl radicals, R⁷ being independently selected from halogen radicals, monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, d having a value of from 0 to 5 inclusive, said substituted monovalent hydrocarbon radicals having from 1 to 4 substituent groups, said substituent groups being selected from hydroxyl, halogens, amino, nitro, --COOH, and --COOR'"'"' wherein R'"'"' is selected from alkyl groups of 1 to 6 carbon atoms and aryl group of from 6 to 12 ring carbon atoms; and

(iii) at least one active ultraviolate radiation absorber selected from benzotriazoles, cyanoacrylates, and hydroxybenophenones and mixtures thereof, said absorber being present at a level selected from between 5 and 15 weight percent based on the total weight of said polyfunctional acrylate monomer, photoinitiator and absorber in said composition.

2. The composition of claim 1 which contains from about 0.1 to about 5 weight percent of said photoinitiator.

3. The composition of claim 1 which contains from 5 to about 12 weight percent of said ultraviolet radiation absorber.

4. The composition of claim 1 which contains from 5 to about 10 weight percent of said ultraviolet radiation absorber.

5. The composition of claim 1 wherein said ultraviolet radiation absorber is a cyanoacrylate.

6. The composition of claim 1 wherein said ultraviolet radiation absorber is a benzotriazole.

7. The composition of claim 1 wherein said ultraviolet radiation absorber is a hydroxybenzophenone.

8. The composition of claim 1 wherein R³ is hydrogen.

9. The composition of claim 8 wherein c has a value of from 2 to about 8.

10. The composition of claim 9 wherein c has a value of from 2 to about 6.

11. The composition of claim 10 wherein c has a value of from 2 to 4.

12. The composition of claim 11 wherein said polyfunctional acrylate monomer is comprised of at least one diacrylate and at least one triacrylate monomer.

13. The composition of claim 1 wherein the monovalent hydrocarbon radicals represented by R" and R⁴ are alkyl radicals.

14. The composition of claim 13 wherein R⁵ is an alkyl radical.

15. The composition of claim 14 wherein d is zero.

16. An ultraviolet radiation curable coating composition for plastic substrates consisting of:

(i) at least one polyfunctional acrylate monomer represented by the formula ##STR15## wherein;

R³ is either a methyl radical or hydrogen;

R² is a c functional hydrocarbon residue, a c functional substituted hydrocarbon residue, a c functional hydrocarbon residue containing at least one ether linkage, or a c functional substituted hydrocarbon residue containing at least one ether linkage, said substituted hydrocarbon residue having from 1 to 4 substituent groups; and

c is an integer having a value of from 2 up to the number of replacable hydrogen atoms present on R² ;

(ii) at least one acetophenone photoinitiator present at a level selected from between about 0.05 to about 10 weight percent based on the total amounts of polyfunctional acrylate monomer and said photoinitiator present in said coating composition, said acetophenone photoinitiator being represented by the formula ##STR16## R⁴ being selected from lower alkyl radicals, R⁵ being selected from hydrogen and alkyl radicals, R⁶ being a --OR" radical wherein R" is selected from hydrogen and lower alkyl radicals, R⁷ being independently selected from halogen radicals, monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, d having a value of from 0 to 5 inclusive, said substituted monovalent hydrocarbon radicals having from 1 to 4 substituent groups, said substituent groups being selected from hydroxyl, halogens, amino, nitro, --COOH, and --COOR'"'"' wherein R'"'"' is selected from alkyl groups of 1 to 6 carbon atoms and aryl group of from 6 to 12 ring carbon atoms;

(iii) at least one active ultraviolate radiation absorber selected from benzotriazoles, cyanoacrylates, and hydroxybenophenones and mixtures thereof, said absorber being present at a level selected from between 5 and 15 weight percent based on the total weight of said polyfunctional acrylate monomer, photoinitiator and absorber in said composition; and

(iv) at least one silicone surfactant present at a level of from about 0.05 to about 3 percent by weight based on the total weight of the polyfunctional acrylate monomer.