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US4522694A
Expired / Lapsed
US
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Process for the photopolymerization of vinyl compounds and photopolymerizable materials used in said process
Assignee: Kulzer GmbH
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Filing: 1984-01-05
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Granted: 1985-06-11
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Expires: 2004-01-05
Abstract
Abstract A process for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of a photoinitiator comprising at least one photosensitizer and at least one reducing agent selected from N-alkyl-pyrazole, N-alkyl-triazole, N-alkyl-tetrazole, N-aryl-benzotriazole, N-aryl-pyrazole, N-aryl-triazole, and N-aryl-tetrazole. Polymerizable materials and products produced by the process are also disclosed which are particularly suited as dental materials.
Inventors
- 👤 Roland Schaefer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 08:46
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; A; A61; A61K; A61K6/00; A61K6/80; A61K6/884; A61K6/887; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
163 words
In a method for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one vinyl compound in the presence of a photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR7## wherein X is selected from the group consisting of CO, C(R 1 ) (R 2 ) and C(R 3 )(OR 4 ), wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of hydrogen and a hydrocarbon radical; n is 0 or 1; and A are hydrocarbon radicals which may be substituted and which may be bonded together with the proviso that when n is 1 and X is C(R 1 )(R 2 ), and when n is 0, A is an aromatic radical; and (b) at least one reducing agent selected from the group consisting of N-alkyl-pyrazole, N-alkyl-triazole, N-alkyl-tetrazole, N-aryl-benzotriazole, N-aryl-pyrazole, N-aryl-tetrazole, and N-aryl-triazole.
Claim 2
Dependent Claim
163 words
In a method for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one vinyl compound in the presence of a photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR7## wherein X is selected from the group consisting of CO, C(R 1 ) (R 2 ) and C(R 3 )(OR 4 ), wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of hydrogen and a hydrocarbon radical; n is 0 or 1; and A are hydrocarbon radicals which may be substituted and which may be bonded together with the proviso that when n is 1 and X is C(R 1 )(R 2 ), and when n is 0, A is an aromatic radical; and (b) at least one reducing agent selected from the group consisting of N-alkyl-pyrazole, N-alkyl-triazole, N-alkyl-tetrazole, N-aryl-benzotriazole, N-aryl-pyrazole, N-aryl-tetrazole, and N-aryl-triazole.
Claim 3
Dependent Claim
21 words
The method of claim 1, wherein said reducing agent is selected from the group consisting of 1-aryl-pyrazolone-(5) 2-aryl-2H-benzotriazole, 1-alkyl-1H-tetrazole, and 1-aryl-1H-tetrazole.
Claim 4
Dependent Claim
15 words
The method of claim 1 wherein said at least one photosensitizer is a diketone compound.
Claim 5
Dependent Claim
10 words
The method of claim 3, wherein the photosensitizer comprises camphorquinone.
Claim 6
Dependent Claim
11 words
The method of claim 4, wherein the photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 7
Dependent Claim
11 words
The method of claim 5, wherein the photosensitizer further comprises 2,2-dimethoxy-1,2-diphenylethanone.
Claim 8
Dependent Claim
22 words
The method of claim 2, wherein said reducing agent is selected from the group consisting of 1-phenyl-3-methylpyrazolone-(5), 1-phenyl-3,4-dimethyl-pyrazolone-(5), 2-(2-acetoxy-3,5-di-tert.-pentyl-phenyl)-2H-benzotriazole, 1,5-dimethyl-1H-tetrazole and 1-phenyl-5-acetylthio-1H-tetrazole.
Claim 9
Dependent Claim
42 words
The method of claim 1, wherein said at least one photosensitizer and said at least one reducing agent are each present in an amount of between 0.01 and 10% by weight based on the weight of said at least one vinyl compound.
Claim 10
Dependent Claim
40 words
The method of claim 8, wherein said at least one photosensitizer and said at least one reducing agent are present in an amount between 0.1 and 5% by weight based on the weight of said at least one vinyl compound.
Claim 11
Dependent Claim
93 words
In a method for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one vinyl compound in the presence of at least one diketone compound and at least one reducing agent selected from the group consisting of 1-aryl-pyrazolone-(5), 2-aryl-2H-benzotriazole, 1-alkyl-1H-tetrazole, and 1-aryl-1H-tetrazole, wherein said diketone compound and said at least one reducing agent are each present in an amount between 0.01 and 10% by weight based on the weight of said at least one vinyl compound.
Claim 12
Dependent Claim
93 words
In a method for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one vinyl compound in the presence of at least one diketone compound and at least one reducing agent selected from the group consisting of 1-aryl-pyrazolone-(5), 2-aryl-2H-benzotriazole, 1-alkyl-1H-tetrazole, and 1-aryl-1H-tetrazole, wherein said diketone compound and said at least one reducing agent are each present in an amount between 0.01 and 10% by weight based on the weight of said at least one vinyl compound.
Claim 13
Dependent Claim
10 words
The method of claim 10, wherein the photosensitizer comprises camphorquinone.
Claim 14
Dependent Claim
11 words
The method of claim 11, wherein the photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 15
Dependent Claim
11 words
The method of claim 12, wherein the photosensitizer further comprises 2,2-dimethoxy-1,2-diphenylethanone.
Claim 16
Dependent Claim
22 words
The method of claim 11, wherein said reducing agent is selected from the group consisting of 1-phenyl-3-methylpyrazolone-(5), 1-phenyl-3,4-dimethyl-pyrazolone-(5), 2-(2-acetoxy-3,5-di-tert.-pentyl-phenyl)-2H-benzotriazole, 1,5-dimethyl-1H-tetrazole and 1-phenyl-5-acetylthio-1H-tetrazole.
Claim 17
Dependent Claim
41 words
The method of claim 14, wherein said at least one photosensitizer and said at least one reducing agent are each present in an amount between 0.1 and 5% by weight based on the weight of said at least one vinyl compound.
Claim 18
Dependent Claim
10 words
The polymer composition produced by the method of claim 1.
Claim 19
Dependent Claim
137 words
A photopolymerizable material comprising at least one vinyl compound and a photoinitiator, said photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR8## wherein X is selected from the group consisting of CO,C(R 1 ) (R 2 ) and C(R 3 )(OR 4 ), wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of hydrogen and a hydrocarbon radical; n is 0 or 1; and A are hydrocarbon radicals which may be substituted and which may be bonded together with the proviso that when n is 1 and X is C(R 1 )(R 2 ), and when n is 0, A is an aromatic radical; and (b) at least one reducing agent selected from the group consisting of N-alkyl-pyrazole, N-alkyl-triazole, N-alkyl-tetrazole, N-aryl-benzotriazole, N-aryl-pyrazole, N-aryl-tetrazole, and N-aryl-triazole.
Claim 20
Dependent Claim
137 words
A photopolymerizable material comprising at least one vinyl compound and a photoinitiator, said photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR8## wherein X is selected from the group consisting of CO,C(R 1 ) (R 2 ) and C(R 3 )(OR 4 ), wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of hydrogen and a hydrocarbon radical; n is 0 or 1; and A are hydrocarbon radicals which may be substituted and which may be bonded together with the proviso that when n is 1 and X is C(R 1 )(R 2 ), and when n is 0, A is an aromatic radical; and (b) at least one reducing agent selected from the group consisting of N-alkyl-pyrazole, N-alkyl-triazole, N-alkyl-tetrazole, N-aryl-benzotriazole, N-aryl-pyrazole, N-aryl-tetrazole, and N-aryl-triazole.
Claim 21
Dependent Claim
22 words
The photopolymerizable material of claim 17, wherein said reducing agent is selected from the group consisting of 1-aryl-pyrazolone-(5), 2-aryl-2H-benzotriazole, 1-alkyl-1H-tetrazole, and 1-aryl-1H-tetrazole.
Claim 22
Dependent Claim
16 words
The photopolymerizable material of claim 17, wherein said at least one photosensitizer is a diketone compound.
Claim 23
Dependent Claim
11 words
The photopolymerizable material of claim 19, wherein the photosensitizer comprises camphorquinone.
Claim 24
Dependent Claim
12 words
The photopolymerizable material of claim 20, wherein the photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 25
Dependent Claim
12 words
The photopolymerizable material of claim 21, wherein the photosensitizer further comprises 2,2-dimethoxy-1,2-diphenylethanone.
Claim 26
Dependent Claim
23 words
The photopolymerizable material of claim 18, wherein said reducing agent is selected from the group consisting of 1-phenyl-3-methyl-pyrazolone-(5), 1-phenyl-3,4-dimethyl-pyrazolone-(5), 2-(2-acetoxy-3,5-di-tert.-pentylphenyl)-2H-benzotriazole, 1,5-dimethyl-1H-tetrazole and 1-phenyl-5-acetylthio-1H-tetrazole.
Claim 27
Dependent Claim
42 words
The photopolymerizable material of claim 17, wherein said at least one photosensitizer and said at least one reducing agent are present in an amount of between 0.01 and 10% by weight based on the weight of said at least one vinyl compound.
Claim 28
Dependent Claim
41 words
The photopolymerizable material of claim 24, wherein said at least one photosensitizer and said at least one reducing agent are present in an amount between 0.1 and 5% by weight based on the weight of said at least one vinyl compound.
Claim 29
Dependent Claim
27 words
The photopolymerizable material of claim 25, wherein said at least one vinyl compound is selected from the group consisting of acrylic acid esters and methacrylic acid esters.
Claim 30
Dependent Claim
20 words
The photopolymerizable material of claim 26, wherein said reducing agent is selected from the group consisting of 1-aryl-pyrazolone-(5) and 2-aryl-2H-benzotriazole.
Claim 31
Dependent Claim
20 words
The photopolymerizable material of claim 26, wherein said reducing agent is selected from the group consisting of 1-phenyl-3-methyl-pyrazolone-(5) and 1-phenyl-3,4-dimethyl-pyrazolone-(5).
Claim 32
Dependent Claim
79 words
The method of claim 11, wherein said at least one photosensitizer and said at least one reducing agent are each present in an amount between 0.1 and 5% by weight based on the weight of said at least one vinyl compound; wherein said at least one vinyl compound is selected from the group consisting of acrylic acid esters and methacrylic acid esters; and wherein said reducing agent is selected from the group consisting of N-alkyl pyrazole and N-aryl pyrazole.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-06-10 | 1988-12-10 | 1989-06-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-10 | 1992-12-10 | 1993-06-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-10 | 1996-12-10 | 1997-06-11 | $7700.00 | Window Closed / Lapsed |