US4263366A
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Radiation curable coating composition comprising an oligomer and a copolymerizable ultra-violet absorber
Assignee: ISP Investments LLC
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Filing: 1979-09-27
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Granted: 1981-04-21
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Expires: 1999-09-27
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 ethylenic ether of Formula IV: ##STR2## where (Ar) 1 and (Ar) 2 are aromatic carbocylic nuclei of the benzene and naphthalene series; X is alkylene, C 2 -C 17 , unsubstituted or substituted; R is alkylene, C 1 -C 10 , oxyalkylene, C 1 -C 10 , alkyleneoxyalkylene, C 1 -C 10 or phenylene, C 1 -C 10 , unsubstituted or substituted with hydroxy, and R' and R" are independently hydrogen or alkyl, C 1 -C 6 . 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
- 👤 Donald H. Lorenz
- 👤 Bruce A. Gruber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:02
CPC Classifications
C; C07; C07C; C07C255/00; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C09; C09D; C09D4/00; Y; Y10; Y10S; Y10S525/00; Y10S525/92; Y10T; Y10T428/00; Y10T428/26; Y10T428/31504; Y10T428/31551; Y10T428/31573; Y10T428/3158
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
169 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: ##STR8## wherein: R 1 is hydrogen or methyl; and Y is a divalent urethane residue; and B. a copolymerizable ultra-violet light absorber compound of Formula IV: ##STR9## 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, C 2 -C 17 , unsubstituted or substituted with halo, cyano, alkyl, C 1 -C 6 , alkoxy, C 1 -C 6 alkoxyalkyl, C 1 -C 6 , or alkoxyalkyleneoxy, C 1 -C 6 ; R is alkylene, C 1 -C 10 , oxyalkylene, C 1 -C 10 alkyleneoxyalkylene, C 1 -C 10 phenylene, C 1 -C 10 , unsubstituted or substituted with hydroxy; and R' and R" are independently hydrogen or alkyl, C 1 -C 6 .
Claim 2
Dependent Claim
169 words
A radiation curable coating composition comprising: A. An oligomer of Formula I: ##STR8## wherein: R 1 is hydrogen or methyl; and Y is a divalent urethane residue; and B. a copolymerizable ultra-violet light absorber compound of Formula IV: ##STR9## 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, C 2 -C 17 , unsubstituted or substituted with halo, cyano, alkyl, C 1 -C 6 , alkoxy, C 1 -C 6 alkoxyalkyl, C 1 -C 6 , or alkoxyalkyleneoxy, C 1 -C 6 ; R is alkylene, C 1 -C 10 , oxyalkylene, C 1 -C 10 alkyleneoxyalkylene, C 1 -C 10 phenylene, C 1 -C 10 , unsubstituted or substituted with hydroxy; and R' and R" are independently hydrogen or alkyl, C 1 -C 6 .
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-inhibitor 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
19 words
A composition according to claim 1 in which in Formula IV, X is alkylene, C 2 -C 6 .
Claim 11
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.
Claim 12
Dependent Claim
30 words
A composition according to claim 1 in which in formula, IV (Ar) 1 and (Ar) 2 are phenyl, X is alkylene, C 2 -C 6 , and --RCR'═CHR" is allyl.
Claim 13
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl allyl ether.
Claim 14
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl 2-methyl-2-propenyl ether.
Claim 15
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl 2-methyl-2-propenyl ether.
Claim 16
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloxy) ethyl vinylbenzyl ether.
Claim 17
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloyloxy) ethyl 3-allyloxy-2-hydroxypropyl ether.
Claim 18
Dependent Claim
15 words
A composition according to claim 1 in which Formula IV is 2-(2-cyano-3,3-diphenylacryloyloxy) ethyl 2-hydroxy-3-butenyl ether.
Claim 19
Dependent Claim
179 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: ##STR10## 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 allyl ether 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
179 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: ##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 allyl ether 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.
References Cited (Backward Citations)
US3644466A
Cited
US4129709A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-20 | 1984-10-20 | 1985-04-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-20 | 1988-10-20 | 1989-04-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-20 | 1992-10-20 | 1993-04-21 | $7700.00 | Window Closed / Lapsed |