US4581389A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for photopolymerization of vinyl compounds and photopolymerizable materials used in said process using 1-aryl-2,5 dialkypyrrole as reducing agent
Assignee: Kulzer GmbH
•
Filing: 1984-01-05
•
Granted: 1986-04-08
•
Expires: 2004-01-05
Abstract
Abstract A method for the production of a polymer composition comprising photopolymerizing at least one vinyl compound in the presence of at least one photoinitiator, said photoinitiator comprising at least one photosensitizer and at least one reducing agent selected from compounds of formula I and II. Polymerizable materials containing said photoinitiators and said at least one vinyl compound are also disclosed. The polymerizable materials are particularly suited for use as dental materials.
Inventors
- 👤 Roland Schaefer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 23:17
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; Y; Y10; Y10S; Y10S522/00; Y10S522/91
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
155 words
In a method for the production of a polymer composition comprising photopolymerizing at least one polymerizable ethylenically unsaturated compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one compound in the presence of a photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR6## wherein X is selected from the group consisting of CO, C(R 1 )(R 2 ) and C(R 3 )(OR 4 ) and wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of a hydrogen atom and a hydrocarbon radical; n is 0 or 1; 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, then A is an aromatic radical; and (b) at least one 1-aryl-2,5-dialkylpyrrole as a reducing agent.
Claim 2
Dependent Claim
155 words
In a method for the production of a polymer composition comprising photopolymerizing at least one polymerizable ethylenically unsaturated compound in the presence of a photoinitiator, the improvement comprising polymerizing said at least one compound in the presence of a photoinitiator comprising: (a) at least one photosensitizer of the formula ##STR6## wherein X is selected from the group consisting of CO, C(R 1 )(R 2 ) and C(R 3 )(OR 4 ) and wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of a hydrogen atom and a hydrocarbon radical; n is 0 or 1; 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, then A is an aromatic radical; and (b) at least one 1-aryl-2,5-dialkylpyrrole as a reducing agent.
Claim 3
Dependent Claim
19 words
The method of claim 1 wherein said reducing agent is selected from the group consisting of 1-(3,4-dimethylphenyl)-2,5-dimethylpyrrole, and 1-(4-ethoxycarbonylphenyl)-2,5-dimethylpyrrole.
Claim 4
Dependent Claim
13 words
The method of claim 1 wherein said photosensitizer is a benzoin alkyl ether.
Claim 5
Dependent Claim
18 words
The method of claim 1 wherein said photosensitizer is selected from the group consisting of benzil and camphorquinone.
Claim 6
Dependent Claim
11 words
The method of claim 4 wherein said photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 7
Dependent Claim
11 words
The method of claim 3 wherein said photosensitizer further comprises 2,2-dimethoxy-1,2-diphenylethanone.
Claim 8
Dependent Claim
19 words
The method of claim 4 wherein said reducing agent is selected from the group consisting of 1-(3,4-dimethylphenyl)-2,5-dimethylpyrrole, and 1-(4-ethoxycarbonylphenyl)-2,5-dimethylpyrrole.
Claim 9
Dependent Claim
11 words
The method of claim 7 wherein said photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 10
Dependent Claim
44 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 polymerizable ethylenically unsaturated compound.
Claim 11
Dependent Claim
43 words
The method of claim 9 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 polymerizable ethylenically unsaturated compound.
Claim 12
Dependent Claim
131 words
A photopolymerizable material comprising at least one polymerizable ethylenically unsaturated compound and a photoinitiator, said 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 ) and wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of a hydrogen atom and a hydrocarbon radical; n is 0 or 1; 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, then A is an aromatic radical; and (b) at least one 1-aryl-2,5-dialkylpyrrole as a reducing agent.
Claim 13
Dependent Claim
131 words
A photopolymerizable material comprising at least one polymerizable ethylenically unsaturated compound and a photoinitiator, said 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 ) and wherein R 1 , R 2 , R 3 , R 4 are each selected from the group consisting of a hydrogen atom and a hydrocarbon radical; n is 0 or 1; 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, then A is an aromatic radical; and (b) at least one 1-aryl-2,5-dialkylpyrrole as a reducing agent.
Claim 14
Dependent Claim
43 words
The photopolymerizable material of claim 11 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 polymerizable ethylenically unsaturated compound.
Claim 15
Dependent Claim
20 words
The photopolymerizable material of claim 11 wherein said reducing agent is selected from the group consisting of 1-(3,4-dimethylphenyl)-2,5-dimethylpyrrole, and 1-(4-ethoxycarbonylphenyl)-2,5-dimethylpyrrole.
Claim 16
Dependent Claim
14 words
The photopolymerizable material of claim 11 wherein said photosensitizer is a benzoin alkyl ether.
Claim 17
Dependent Claim
19 words
The photopolymerizable material of claim 14 wherein said photosensitizer is selected from the group consisting of benzil and camphorquinone.
Claim 18
Dependent Claim
12 words
The photopolymerizable material of claim 15 wherein said photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 19
Dependent Claim
12 words
The photopolymerizable material of claim 15 wherein said photosensitizer further comprises 2,2-dimethoxy-1,2-diphenylethanone.
Claim 20
Dependent Claim
20 words
The photopolymerizable material of claim 15 wherein said reducing agent is selected from the group consisting of 1-(3,4-dimethylphenyl)-2,5-dimethylpyrrole, and 1-(4-ethoxycarbonylphenyl)-2,5-dimethylpyrrole.
Claim 21
Dependent Claim
12 words
The photopolymerizable material of claim 18 wherein said photosensitizer further comprises 2,2-dialkoxy-1,2-diphenylethanone.
Claim 22
Dependent Claim
45 words
The photopolymerizable material of claim 11 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 polymerizable polymerizable ethylenically unsaturated compound.
Claim 23
Dependent Claim
43 words
The photopolymerizable material of claim 18 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 at least one polymerizable polymerizable ethylenically unsaturated compound.
References Cited (Backward Citations)
GB569974A
Cited
US3066112A
Cited
US4071424A
Cited
GB1408265A
Cited
US4071424B1
Cited
GB1428672A
Cited
US4243578A
Cited
US4025347A
Cited
US4008085A
Cited
US4197120A
Cited
US4267133A
Cited
GB2018666A
Cited
US4307182A
Cited
EP0049922A2
Cited
US4382102A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-04-07 | 1989-10-07 | 1990-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-07 | 1993-10-07 | 1994-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-07 | 1997-10-07 | 1998-04-08 | $7700.00 | Window Closed / Lapsed |