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US4437836A
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Photopolymerizable dental compositions
Assignee: Kulzer GmbH
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Filing: 1982-09-01
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Granted: 1984-03-20
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Expires: 2002-09-01
Abstract
Abstract In a photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer. (b) at least one photoinitiator selected from organic mono- and/or di-carbonyl compounds and (c) a photoactivator, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR1## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ether of ether group, or R 1 and R 2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR2## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR3## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 . The compositions are especially useful for dental prostheses, fillings and coatings since they are not irritating to human tissue.
Inventors
- 👤 Robert Schmitz-Josten
- 👤 Carlhans Suling
- 👤 Wolfgang Podszun
- 👤 Bruno Bomer
- 👤 Manfred Borgardt
- 👤 Michael Walkowiak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 15:49
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; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/12
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
256 words
A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from organic mono- or di-carbonyl compounds and (c) as a photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR42## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR43## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR44## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
Claim 2
Dependent Claim
256 words
A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from organic mono- or di-carbonyl compounds and (c) as a photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR42## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR43## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR44## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
Claim 3
Dependent Claim
16 words
A composition according to claim 1, containing as a further component at least one fine-particled filler.
Claim 4
Dependent Claim
18 words
A composition according to claim 1, in which R 1 is a hydrogen atom or a methyl group.
Claim 5
Dependent Claim
14 words
A composition according to claim 1, in which R 2 is a hydrogen atom.
Claim 6
Dependent Claim
14 words
A composition according to claim 1, in which R 3 is a methyl group.
Claim 7
Dependent Claim
16 words
A composition according to claim 1, in which R 4 and R 5 each is hydrogen.
Claim 8
Dependent Claim
19 words
A composition according to claim 1, in which X contains at least one, hydroxyl, epoxy or ethylenically unsaturated group.
Claim 9
Dependent Claim
28 words
A composition according to claim 1, in which X is a radical of the formula ##STR45## and contains at least one allyl, acrylamide, methacrylamide, acrylate or methacrylate group.
Claim 10
Dependent Claim
29 words
A composition according to claim 1 in which the moiety containing radicals R 1 to R 3 is in the meta- or para-position to the --SO 2 X group.
Claim 11
Dependent Claim
39 words
A composition according to claim 2, in which R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom, R 3 is a methyl group, and R 4 and R 5 each is hydrogen.
Claim 12
Dependent Claim
264 words
In a photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from organic mono- or di-carbonyl compounds and (c) a photoactivator, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR46## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR47## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR48## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
Claim 13
Dependent Claim
264 words
In a photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from organic mono- or di-carbonyl compounds and (c) a photoactivator, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR46## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR47## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR48## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
Claim 14
Dependent Claim
33 words
A composition according to claim 11, wherein (b) is present in about 0.001 to 10% by weight of (a) and the molar ratio of (b) to (c) is from about 0.01:1 to 10:1.
Claim 15
Dependent Claim
288 words
In the formation of a dental prosthesis, filling or coating comprising forming a composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from the organic mono- or di-carbonyl compounds and (c) a photoactivator, shaping said composition and then polymerizing said composition under the influence of light, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR49## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together from a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR50## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR51## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
Claim 16
Dependent Claim
288 words
In the formation of a dental prosthesis, filling or coating comprising forming a composition comprising (a) at least one ethylenically unsaturated photopolymerizable monomer, (b) at least one photoinitiator selected from the organic mono- or di-carbonyl compounds and (c) a photoactivator, shaping said composition and then polymerizing said composition under the influence of light, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR49## in which R 1 and R 2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ester or ether group, or R 1 and R 2 together from a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom, R 3 independently of R 1 , has any of the meanings given for R 1 or is a group of the formula ##STR50## R 4 and R 5 each independently is a hydrogen atom, an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by halogen, or a halogen atom, or R 4 and R 5 are in ortho-positions relative to one another and, together with the aromatic nucleus, form a 4- to 8-membered ring, and X is an alkyl or alkenyl group which has 1 to 10 carbon atoms and is optionally substituted by a hydroxyl, amino, urethane, urea or ester group, or is a group of the formula ##STR51## wherein R 6 and R 7 , independently of R 1 and R 2 , have any of the meanings given above for R 1 and R 2 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-20 | 1987-09-19 | 1988-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-20 | 1991-09-19 | 1992-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-20 | 1995-09-19 | 1996-03-20 | $7700.00 | Window Closed / Lapsed |