Patent CA1179094A successfully refreshed from Google Patents.
CA1179094A
Expired / Lapsed
CA
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Radiation curable coating composition comprising an oligomer and a copolymerizable ultra-violet absorber
Assignee: GAF Corp
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Filing: 1980-08-11
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Granted: 1984-12-04
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Expires: 2000-08-11
Abstract
Abstract ABSTRACT What is described herein is a radiation curable coating composition comprising: A. An oligomer of Formula I: wherein: R1 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: (IV) where (Ar)1 and (Ar)2 are aromatic carbocyclic nuclei of the benzene and naphthalene series; X is alkylene, C2-C17, unsubstituted or substituted; and Y is a copolymerizable radical selected from acryloyl, alkylacryloyl, acryloxyalkyl, acryloxyhydroxyalkyl, or alkylacryloxyhydroxyalkyl, having from C3-C12 carbon atoms, or -RCR'=CHR', where R is alkylene C1-C10, oxyalkyene, C1-C10, alkyleneoxyalkylene, C1-C10 or phenylene, C1-C10, unsubstituted or substituted with hydroxy, and R' and R'' are independently hydrogen or alkyl, C1-C6.
Inventors
- 👤 Bruce A. Gruber
- 👤 Donald H. Lorenz
Bibliographic Details
Application Number
—
Jurisdiction
CA
Data Source
google_patents
Last Synchronized
2026-11-04 14:14
CPC Classifications
C; C09; C09D; C09D4/00
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
153 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: (I) wherein: R1 is hydrogen or methyl; and Y is a divalent urethane residue; and B, a copolymerizable ultra-violet light absorber compounds of Formula IV: (IV) where: (Ar)1 and (Ar)2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from 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 alkylene, C2-C17, unsubstituted or substituted with halo, cyano, alkyl, C1-C6, alkoxy, C1-C6 alkoxyalkyl, C1-C6, or alkoxyalkyleneoxy, C1-C6; and Y is a copolymerizable radical selected from acryloyl, C3-C12, alkylacryoyl, C3-C12, acryloxyalkyl, C3-C12, acryloxyhydroxyalkyl, C3-C12, and alkylacryloxyhydroxyalkyl, C3-C12; or -RCR' = CHR', where R is alkylene, C1-C10, oxyalkylene, C1-C10 alkyleneoxyalkylene, C1-C10 phenylene, C1-C10, unsubstituted or substituted with hydroxy; and R' and R'' are independently hydrogen or alkyl, C1-C6.
Claim 2
Dependent Claim
153 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: (I) wherein: R1 is hydrogen or methyl; and Y is a divalent urethane residue; and B, a copolymerizable ultra-violet light absorber compounds of Formula IV: (IV) where: (Ar)1 and (Ar)2 are aromatic carbocyclic nuclei of the benzene and naphthalene series and are independently selected from 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 alkylene, C2-C17, unsubstituted or substituted with halo, cyano, alkyl, C1-C6, alkoxy, C1-C6 alkoxyalkyl, C1-C6, or alkoxyalkyleneoxy, C1-C6; and Y is a copolymerizable radical selected from acryloyl, C3-C12, alkylacryoyl, C3-C12, acryloxyalkyl, C3-C12, acryloxyhydroxyalkyl, C3-C12, and alkylacryloxyhydroxyalkyl, C3-C12; or -RCR' = CHR', where R is alkylene, C1-C10, oxyalkylene, C1-C10 alkyleneoxyalkylene, C1-C10 phenylene, C1-C10, unsubstituted or substituted with hydroxy; and R' and R'' are independently hydrogen or alkyl, C1-C6.
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
28 words
The coating composition of Claim 3 wherein the addition polymerization inhibitor is present in an amount from 100-300 PPM 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
17 words
A composition according to Claim 1 in which in Formula IV both (Ar)1 and (Ar)2 are phenyl.
Claim 10
Dependent Claim
15 words
A composition according to Claim 1 in which in Formula IV X is alkylene, C2-C6.
Claim 11
Dependent Claim
22 words
A composition according to Claim 1 in which in Formula IV, Y is acryloyl, C3-C12, methacryloyl, C3-C12, 3-acryloxy-2-hydroxypropyl, C3-C12 or 3-methacryloxy-2-hydroxypropyl, C3-C12.
Claim 12
Dependent Claim
32 words
A composition according to Claim 1 in which in formula IV (Ar) and (Ar)2 are phenyl, X is alkylene, C2-C6 and Y is acryloyl, C3-C12, methacryloyl, C3-C12, 3-acryloxy-2-hydroxypropyl C3-C12, or 3-methacryloxy-2-hydroxypropyl, C3-C12.
Claim 13
Dependent Claim
14 words
A composition according to Claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl acrylate.
Claim 14
Dependent Claim
14 words
A composition according to Claim ] in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl methacrylate.
Claim 15
Dependent Claim
14 words
A composition according to Claim 1 in which Formula IV is 3-(2-cyano-3,3-diphenylacryloxy) propyl acrylate.
Claim 16
Dependent Claim
14 words
A composition according to Claim 1 in which Formula IV is 4-(2-cyano-3,3-diphenylacryloxy) butyl acrylate.
Claim 17
Dependent Claim
13 words
A composition according to Claim 1 in which Formula IV is 3-(2-cyano-3,3-diphenylacryloyloxy)-2-hydroxypropyl acrylate.
Claim 18
Dependent Claim
13 words
A composition according to Claim 1 in which Formula IV is 3-(2-cyano-3,3-diphenylacryloyloxy)-2-hydroxypropyl methacrylate.
Claim 19
Dependent Claim
175 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: (II) wherein: R1 is hydrogen or methyl; R2 is lower alkylene; R3 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
175 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: (III) wherein: R1 is hydrogen or methyl; R2 is lower alkylene; R3 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.
Claim 21
Dependent Claim
63 words
A process for coating a substrate comprising in sequence the steps of: I. contacting the substrate with a coating composition according to Claim 6, wherein the amount of B. is 0.5 to 5 weight percent based on the weight of the composition; and, II. exposing the coated substrate to actinic radiation until an adherent dry polymerized weather-resistant coating is formed on the substrate.
Claim 22
Dependent Claim
28 words
A laminate comprising a planar sheet of clear polyvinyl chloride with a film coating 0.1 to 10 mils in thickness comprising a cured coating composition of Claim 1.
Claim 23
Dependent Claim
21 words
A composition according to Claim 1 in which in Formula IV, RCR'=CHR" is allyl, crotyl, methylpropenyl, vinylbenzyl, vinyloxyether, allyloxy-2-hydroxypropyl or 2-hydroxy-3-butenyl.
References Cited (Backward Citations)
No citation records indexed.
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