US4284485A
Expired / Lapsed
US
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Photocurable compositions
Assignee: BASF Corp
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Filing: 1979-07-05
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Granted: 1981-08-18
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Expires: 1999-07-05
Abstract
Abstract The use of photo-initiators of the formula I or II ##STR1## in which n is 1 or 2, Ar is a monovalent or divalent aromatic radical, X is a tertiary amino group, a hydroxyl or ether group or a siloxy group, R 1 and R 2 are alkyl, substituted alkyl, alkenyl, cycloalkyl or phenylalkyl or together are alkylene or oxa- or aza-alkylene and R 3 is a direct bond or a divalent aliphatic, cycloaliphatic or aromatic radical, in combination with light stabilizers from the category of the polyalkylpiperidine derivatives in the photopolymerization of ethylenically unsaturated compounds results in polymers with high stability to light and low yellowing.
Inventors
- 👤 Godwin Berner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:37
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031; C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C09; C09D; C09D175/00; C09D175/04; C09D175/14; C09D175/16
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
439 words
A photocurable composition consisting of (a) one or more ethylenically unsaturated, photocurable compounds, (b) at least one photo-initiator of the formula I or II ##STR4## in which n is 1 or 2 and, if n is 1, Ar is unsubstituted phenyl or phenyl substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 alkyl, -OAlk, phenyl, -Ophenyl, --SAlk, --SCH 2 CH 2 OH or -Sphenyl, or indanyl or tetrahydronaphthyl, and Alk is a lower alkyl radical having 1-4 C atoms, and if n is 2 Ar is C 6 -C 12 arylene or a group -phenylene-T-phenylene-, in which T is --O--, --S--, --CH 2 -- or --CH 2 CH 2 --, X is one of the groups --NR 4 R 5 , --OR 6 or --OSiR 7 (R 8 ) 2 , R 1 is unsubstituted C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by --OH, OAlk, C 2 -C 8 acyloxy, --NR 4 R 5 , --COOAlk or --CN, or C 3 -C 4 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 phenylalkyl, R 2 has one of the meanings defined for R 1 or together with R 1 is C 2 -C 8 alkylene or C 3 -C 9 oxa- or aza-alkylene, R 3 is a direct bond, C 1 -C 6 alkylene, C 2 -C 6 oxa-alkylene, C 2 -C 6 thia-, S-oxothia- or S-dioxothiaalkylene, phenylene, diphenylene or a group -phenylene-T-phenylene-, or together with the two substituents R 2 and the two C atoms to which these substituents are bonded forms a cyclopentane, cyclohexane, endomethylenecyclohexane or cyclohexane ring, R 4 is C 1 -C 12 alkyl or C 2 -C 4 alkyl which is substituted by --OH or OAlk, R 5 is C 1 -C 12 alkyl or C 2 -C 4 alkyl which is substituted by OH or OAlk, or together with R 4 is C 4 -C 5 alkylene, which can be interrupted by --O-- or --NR 9 --, R 6 is hydrogen, C 1 -C 12 alkyl, C 1 -C 8 alkyl substituted by Cl, Br, OH, OAlk, SAlk, C 2 -C 8 acyloxy, --COOAlk, --CONHAlk, --CON(Alk) 2 or CN, or C 3 -C 5 alkenyl, cyclohexyl, benzyl, unsubstituted phenyl or phenyl substituted by Cl or Alk, or 2-tetrahydropyranyl, R 7 and R 8 are identical or different and are C 1 -C 4 alkyl or phenyl and R 9 is C 1 -C 4 alkyl, --CH 2 CH 2 CN or --CH 2 CH 2 COOAlk, and (c) at least one light stabiliser from the category of the polyalkylpiperidine derivatives.
Claim 2
Dependent Claim
439 words
A photocurable composition consisting of (a) one or more ethylenically unsaturated, photocurable compounds, (b) at least one photo-initiator of the formula I or II ##STR4## in which n is 1 or 2 and, if n is 1, Ar is unsubstituted phenyl or phenyl substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 alkyl, -OAlk, phenyl, -Ophenyl, --SAlk, --SCH 2 CH 2 OH or -Sphenyl, or indanyl or tetrahydronaphthyl, and Alk is a lower alkyl radical having 1-4 C atoms, and if n is 2 Ar is C 6 -C 12 arylene or a group -phenylene-T-phenylene-, in which T is --O--, --S--, --CH 2 -- or --CH 2 CH 2 --, X is one of the groups --NR 4 R 5 , --OR 6 or --OSiR 7 (R 8 ) 2 , R 1 is unsubstituted C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by --OH, OAlk, C 2 -C 8 acyloxy, --NR 4 R 5 , --COOAlk or --CN, or C 3 -C 4 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 phenylalkyl, R 2 has one of the meanings defined for R 1 or together with R 1 is C 2 -C 8 alkylene or C 3 -C 9 oxa- or aza-alkylene, R 3 is a direct bond, C 1 -C 6 alkylene, C 2 -C 6 oxa-alkylene, C 2 -C 6 thia-, S-oxothia- or S-dioxothiaalkylene, phenylene, diphenylene or a group -phenylene-T-phenylene-, or together with the two substituents R 2 and the two C atoms to which these substituents are bonded forms a cyclopentane, cyclohexane, endomethylenecyclohexane or cyclohexane ring, R 4 is C 1 -C 12 alkyl or C 2 -C 4 alkyl which is substituted by --OH or OAlk, R 5 is C 1 -C 12 alkyl or C 2 -C 4 alkyl which is substituted by OH or OAlk, or together with R 4 is C 4 -C 5 alkylene, which can be interrupted by --O-- or --NR 9 --, R 6 is hydrogen, C 1 -C 12 alkyl, C 1 -C 8 alkyl substituted by Cl, Br, OH, OAlk, SAlk, C 2 -C 8 acyloxy, --COOAlk, --CONHAlk, --CON(Alk) 2 or CN, or C 3 -C 5 alkenyl, cyclohexyl, benzyl, unsubstituted phenyl or phenyl substituted by Cl or Alk, or 2-tetrahydropyranyl, R 7 and R 8 are identical or different and are C 1 -C 4 alkyl or phenyl and R 9 is C 1 -C 4 alkyl, --CH 2 CH 2 CN or --CH 2 CH 2 COOAlk, and (c) at least one light stabiliser from the category of the polyalkylpiperidine derivatives.
Claim 3
Dependent Claim
62 words
A composition according to claim 1, wherein component (b) is a photocuring agent of the formula I or II in which n is 1 or 2, X is --OR 6 or --OSiR 7 (R 8 ) 2 and Ar, R 1 , R 2 , R 3 , R 6 , R 7 and R 8 are as defined in claim 1.
Claim 4
Dependent Claim
102 words
A composition according to claim 1, wherein component (b) is a photocuring agent of the formula I or II in which n is 1, X is a hydroxyl group, Ar is an unsubstituted phenyl radical or a phenyl radical monosubstituted or disubstituted by C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, phenoxy, C 1 -C 4 -alkylthio, phenylthio or halogen, and R 1 and R 2 independently of one another are C 1 -C 5 -alkyl, or R 1 and R 2 together are tetramethylene or pentamethylene, and R 3 is a direct bond or C 1 -C 8 -alkylene.
Claim 5
Dependent Claim
80 words
A composition according to claim 1, consisting of (a) one or more photopolymerisable compounds of the series comprising the acrylic and methacrylic acid derivatives, (b) a photo-initiator of the formula I, in which n=1, X is --OH or --OSi(CH 3 ) 3 , Ar is phenyl, alkylphenyl, alkoxyphenyl or chlorophenyl and R 1 and R 2 are methyl, or R 1 and R 2 together are tetramethylene or pentamethylene, and (c) a light stabiliser from the category of the polyalkylpiperidines.
Claim 6
Dependent Claim
21 words
A composition according to claim 4, wherein the light stabiliser (c) is an acrylic or methacrylic acid derivative of a polyalkylpiperidine.
Claim 7
Dependent Claim
24 words
A composition according to claim 4, wherein component (a) is a polyurethane acrylate or a mixture thereof with other acrylic or methacrylic acid derivatives.
Claim 8
Dependent Claim
16 words
A composition according to claim 1, which contains 0.1 to 10% by weight of component (b).
Claim 9
Dependent Claim
16 words
A composition according to claim 1, which contains 0.02 to 5% by weight of component (c).
References Cited (Backward Citations)
US3639321A
Cited
DE1694149C2
Cited
DE1694253A1
Cited
US3982942A
Cited
US4089762A
Cited
US4139520A
Cited
US4048034A
Cited
US4169167A
Cited
US4201642A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-17 | 1985-02-16 | 1985-08-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-17 | 1989-02-16 | 1989-08-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-17 | 1993-02-16 | 1993-08-18 | $7700.00 | Window Closed / Lapsed |