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US4276136A
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Radiation curable coating composition comprising an ethylenically unsaturated oligomer and an ethylenically unsaturated copolymerizable ultra-violet absorber
Assignee: ISP Investments LLC
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Filing: 1979-08-30
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Granted: 1981-06-30
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Expires: 1999-08-30
Abstract
Abstract What is described herein is a radiation curable coating composition comprising: A. An oligomer of Formula I: ##STR1## wherein: R 1 is hydrogen or methyl; and Y is a divalent urethane residue; and B. a copolymerizable ultra-violet light absorber which is a copolymerizable (2-cyano-3,3-diphenylacryloxy) alkylene acrylic acid ester of Formula IV: ##STR2## where (Ar) 1 and (Ar) 2 are aromatic carbocylic nuclei of the benzene and naphthalene series; X is C 2 -C 17 alkylene, unsubstituted or substituted; and Z is a copolymerizable radical selected from acryloyl, alkylacryloyl, acryloxyalkyl, acryloxyhydroxyalkyl, or alkylacryloxyhydroxyalkyl, having from C 3 -C 12 carbon atoms. Preferably the coating composition contains a vinyl monomer, such as N-vinyl-2-pyrrolidone or an acrylic acid ester, which is copolymerizable with the oligomer. The process for curing the composition also is disclosed.
Inventors
- 👤 Bruce A. Gruber
- 👤 Donald H. Lorenz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:33
CPC Classifications
C; C07; C07C; C07C255/00; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C09; C09D; C09D4/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
168 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: ##STR9## wherein: R 1 is hydrogen or methyl; and Y is a divalent urethane containing radical produced from a polyol and a diisocyanate; and B. a copolymerizable ultra-violet light absorber compounds of Formula IV: ##STR10## where: (Ar) 1 and (Ar) 2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from the group consisting of phenyl or phenyl substituted with alkyl, halo, alkoxy, carboxy, carbalkoxy, cyano, acetyl, benzoyl, phenyl, alkyl phenyl, phenoxy phenyl, alkyl substituted phenoxy, or alkoxy phenyl substituted phenyl and naphthyl; X is C 2 -C 17 alkylene, unsubstituted or substituted with halo, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyalkyl, or C 1 -C 6 alkoxyalkyleneoxy; and Z is a copolymerizable radical selected from the group consisting of acryloyl, C 3 -C 12 alkylacryoyl, C 3 -C 12 acryloxyalkyl, C 3 -C 12 acryloxyhydroxyalkyl, and C 3 -C 12 alkylacryloxyhydroxyalkyl.
Claim 2
Dependent Claim
168 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: ##STR9## wherein: R 1 is hydrogen or methyl; and Y is a divalent urethane containing radical produced from a polyol and a diisocyanate; and B. a copolymerizable ultra-violet light absorber compounds of Formula IV: ##STR10## where: (Ar) 1 and (Ar) 2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from the group consisting of phenyl or phenyl substituted with alkyl, halo, alkoxy, carboxy, carbalkoxy, cyano, acetyl, benzoyl, phenyl, alkyl phenyl, phenoxy phenyl, alkyl substituted phenoxy, or alkoxy phenyl substituted phenyl and naphthyl; X is C 2 -C 17 alkylene, unsubstituted or substituted with halo, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyalkyl, or C 1 -C 6 alkoxyalkyleneoxy; and Z is a copolymerizable radical selected from the group consisting of acryloyl, C 3 -C 12 alkylacryoyl, C 3 -C 12 acryloxyalkyl, C 3 -C 12 acryloxyhydroxyalkyl, and C 3 -C 12 alkylacryloxyhydroxyalkyl.
Claim 3
Dependent Claim
15 words
The coating composition of claim 1 further comprising a vinyl monomer copolymerizable with the oligomer.
Claim 4
Dependent Claim
26 words
The coating composition of claim 1 further comprising an addition polymerization inhibitor present in an amount sufficient to avoid the auto-polymerization of the composition during storage.
Claim 5
Dependent Claim
30 words
The coating composition of claim 3 wherein the addition polymerization inhibitor is present in an amount from 100-300 parts per million weight percent based upon the weight of the composition.
Claim 6
Dependent Claim
20 words
The coating composition of claim 3 wherein the weight ratio of oligomer to vinyl monomer is from 1:9 to 9:1.
Claim 7
Dependent Claim
31 words
The coating composition of claim 1 further comprising a photo-initiator present in an amount sufficient to initiate the desired polymerization under the influence of the amount of actinic light energy absorbed.
Claim 8
Dependent Claim
29 words
The coating composition of claim 1 wherein the ultra-violet light absorber is present in an amount from 0.5 to 5 weight percent based on the weight of the composition.
Claim 9
Dependent Claim
19 words
A composition according to claim 1 in which in Formula IV both (Ar) 1 and (Ar) 2 are phenyl.
Claim 10
Dependent Claim
18 words
A composition according to claim 1 in which in Formula IV X is C 2 -C 6 alkylene.
Claim 11
Dependent Claim
18 words
A composition according to claim 1 in which in Formula IV, Z is acryloyl, methacryloyl, 3-acryloxy-2-hydroxypropyl, or 3-methacryloxy-2-hydroxypropyl.
Claim 12
Dependent Claim
33 words
A composition according to claim 1 in which in formula IV (Ar) 1 and (Ar) 2 are phenyl, X is C 2 -C 6 alkylene, and Z is acryloyl, methacryloyl, 3-acryoxy-2-hydroxypropyl, or 3-methacryloxy-2-hydroxypropyl.
Claim 13
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 2-(2-cyano-3,3-diphenylacryloxy)ethyl acrylate.
Claim 14
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 2-(2-cyano-3,3-diphenylacryloxy)ethyl methacrylate.
Claim 15
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 3-(2-cyano-3,3-diphenylacryloxy)propyl acrylate.
Claim 16
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 4-(2-cyano-3,3-diphenylacryloxy)butyl acrylate.
Claim 17
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 3-(2-cyano-3,3-diphenylacryloyloxy)-2-hydroxypropyl acrylate.
Claim 18
Dependent Claim
14 words
A composition according to claim 1 in which the absorber compound is 3-(2-cyano-3,3-diphenylacryloyloxy)-2-hydroxypropyl methacrylate.
Claim 19
Dependent Claim
177 words
A coating composition of claim 1 which is photopolymerizable in the presence of ultra-violet light to produce an adherent coating that is weather-resistant, flexible, scratch-resistant, stain-resistant, abrasion-resistant, and solvent-resistant, said coating composition consisting essentially of: A. an oligomer of Formula II: ##STR11## wherein: R 1 is hydrogen or methyl; R 2 is lower alkylene; R 3 is aliphatic or cycloaliphatic; X is --O-- or --NH--; n is an integer from 2 to 50 inclusive; B. N-vinyl-2-pyrrolidone; C. hexanediol diacrylate; D. 2-(2-cyano-3,3-diphenylacryloxy)ethyl acrylate present in an amount from 0.5 to 5 weight percent based on the weight of the composition; E. a photo-initiator present in an amount from 0.01 to 5 weight percent based on the weight of the composition; F. an addition polymerization inhibitor present in an amount from 100-300 PPM based on the weight of the composition; G. a silicone surfactant present in an amount from 0.1 to 5 percent based on the weight of the composition, wherein the ratio A:B is from 1:3 to 3:1, and wherein the ratio A:C is from 1:3 to 3:1.
Claim 20
Dependent Claim
177 words
A coating composition of claim 1 which is photopolymerizable in the presence of ultra-violet light to produce an adherent coating that is weather-resistant, flexible, scratch-resistant, stain-resistant, abrasion-resistant and solvent-resistant, said coating composition consisting essentially of: A. an oligomer of Formula III: ##STR12## wherein: R 1 is hydrogen or methyl; R 2 is lower alkylene; R 3 is aliphatic or cycloaliphatic; X is --O-- or --NH--; n is an integer from 2 to 50 inclusive; B. N-vinyl-2-pyrrolidone; C. hexanediol diacrylate; D. 2-(2-cyano-3,3-diphenylacryloxy)ethyl methacrylate, present in an amount from 0.5 to 3 weight percent based on the weight of the composition. E. a photo-initiator present in an amount from 0.01 to 5 weight percent based on the weight of the composition; F. an addition polymerization inhibitor present in an amount from 100-300 PPM based on the weight of the composition; G. a silicone surfactant present in an amount from 0.1 to 5 percent based on the weight of the composition, wherein the ratio A:B is from 1:3 to 3:1; and wherein the ratio A:C is from 1:3 to 3:1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-06-29 | 1984-12-29 | 1985-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-29 | 1988-12-29 | 1989-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-29 | 1992-12-29 | 1993-06-30 | $7700.00 | Window Closed / Lapsed |