US4548689A
Expired / Lapsed
US
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Photocurable resin composition
Assignee: Mitsui Chemicals Inc
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Filing: 1984-09-25
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Granted: 1985-10-22
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Expires: 2004-09-25
Abstract
Abstract Disclosed is a photocurable composition comprising (a) a radical-polymerizable monomer, (b) an alpha -ketocarbonyl compound and (c) a derivative of mercaptobenzimidazole, mercaptobenzothiazole or mercaptobenzoxazole or an aromatic amine nucleus-substituted with an electron-attractive group. This composition has a high photocuring speed at a temperature close to normal temperature and gives a cured product excellent in various physical properties. This composition is valuable as a dental adhesive or resin.
Inventors
- 👤 Takeshi Sakashita
- 👤 Takayuki Nakano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 06:18
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031; A; A61; A61K; A61K6/00; A61K6/60; A61K6/62; A61K6/80; A61K6/884; A61K6/887; C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
225 words
A photocurable composition comprising (a) a radical-polymerizable monomer, (b) an α-ketocarbonyl compound and (c) an amine, wherein the amine (c) is at least one member selected from the group consisting of compounds represented by the following general formula: ##STR11## wherein X stands for >NR 2 , an oxygen atom or a sulfur atom, Y stands for a hydrogen atom, --SR 3 or a monovalent, divalent or trivalent metal, R 1 stands for an alkyl group, an aryl group, an aralkyl group or a halogen atom, n is an integer of from 0 to 4 with the proviso that when n is 2 or larger, a plurality of groups R 1 may be the same or different, R 2 stands for a hydrogen atom, an alkyl group, an aryl group or an aralkyl group, and R 3 stands for an alkyl group or an aryl group, or a group represented by the following general formula: ##STR12## wherein X, R 1 and n are as defined above, and substituted amines represented by the following general formula: ##STR13## wherein R 4 stands for a hydrogen atom or an alkyl group, R 5 stands for a hydrogen atom, an alkyl group, a hydroxyalkyl group of an aryl group, R 6 stands for a monovalent, electron-attractive atom or organic group, and n is an integer of from 0 to 4.
Claim 2
Dependent Claim
225 words
A photocurable composition comprising (a) a radical-polymerizable monomer, (b) an α-ketocarbonyl compound and (c) an amine, wherein the amine (c) is at least one member selected from the group consisting of compounds represented by the following general formula: ##STR11## wherein X stands for >NR 2 , an oxygen atom or a sulfur atom, Y stands for a hydrogen atom, --SR 3 or a monovalent, divalent or trivalent metal, R 1 stands for an alkyl group, an aryl group, an aralkyl group or a halogen atom, n is an integer of from 0 to 4 with the proviso that when n is 2 or larger, a plurality of groups R 1 may be the same or different, R 2 stands for a hydrogen atom, an alkyl group, an aryl group or an aralkyl group, and R 3 stands for an alkyl group or an aryl group, or a group represented by the following general formula: ##STR12## wherein X, R 1 and n are as defined above, and substituted amines represented by the following general formula: ##STR13## wherein R 4 stands for a hydrogen atom or an alkyl group, R 5 stands for a hydrogen atom, an alkyl group, a hydroxyalkyl group of an aryl group, R 6 stands for a monovalent, electron-attractive atom or organic group, and n is an integer of from 0 to 4.
Claim 3
Dependent Claim
22 words
A composition as set forth in claim 1, wherein the amine (c) is 2-mercaptobenzothiazole, 2-mercaptomethylbenzothiazole, zinc (II) 2-mercaptobenzothiazole or zinc (II) 2-mercaptomethylbenzothiazole.
Claim 4
Dependent Claim
108 words
A composition as set forth in claim 1, wherein the amine (C) is a substituted aromatic amine represented by the following general formula: ##STR14## wherein R 4 stands for a hydrogen atom or an alkyl group, R 5 stands for a hydrogen atom, an alkyl group,, a hydroxyalkyl group or an aryl group, R 7 stands for a hydrogen atom, an alkyl group, a hydroxyl group, an alkoxyl group, a hydroxyalkyl group, an aryl group or a group --NR 8 R 9 in which R 8 and R 9 stand for a hydrogen atom or an alkyl group, and n is an integer of from 0 to 4.
Claim 5
Dependent Claim
20 words
A composition as set forth in claim 3, wherein the substituted aromatic amine is 4-dimethylaminobenzaldehyde, 4-dimethylaminobenzoic acid or methyl 4-dimethylaminobenzoate.
Claim 6
Dependent Claim
24 words
A composition as set forth in claim 1,wherein the amine (c) is a substituted aromatic amine in which R 6 is a cyano group.
Claim 7
Dependent Claim
17 words
A composition as set forth in claim 5, wherein the substituted aromatic amine is N,N-dimethyl-p-cyanoaniline or N,N-diethyl-p-cyanoaniline.
Claim 8
Dependent Claim
23 words
A composition as set forth in claim 1, wherein the radical-polymerizable monomer is a monomer having at least one acryloyl or methacryloyl group.
Claim 9
Dependent Claim
69 words
A composition as set forth in claim 1, wherein the radical-polymerizable monomer is a combination of (i) an ester monomer of an aliphatic alcohol or aliphatic polyol with methacrylic acid and (ii) at least one monomer selected from the group consisting of an ester monomer of a polyol having a bisphenol skeleton or dihydric phenol skeleton with methacrylic acid and a methacryloyloxyl group-containing aromatic polycarboxylic acid or its anhydride.
Claim 10
Dependent Claim
26 words
A composition as set forth in claim 8, wherein the monomers (i) and (ii) are present at a (i)/(ii) weight ratio of from 5/95 to 95/5.
Claim 11
Dependent Claim
16 words
A composition as set forth in claim 1, wherein the α-ketocarbonyl compound (b) is an α-diketone.
Claim 12
Dependent Claim
17 words
A composition as set forth in claim 1, wherein the α-ketocarbonyl compound (b) is benzil or camphorquinone.
Claim 13
Dependent Claim
61 words
A composition as set forth in claim 1, wherein the α-ketocarbonyl compound (b) is present in an amount of 0.01 to 15 parts by weight per 100 parts by weight of the radical-polymerizable monomer (a) and the amine (c) is present in an amount of 0.01 to 15 parts by weight per 100 parts by weight of the radical-polymerizable monomer (a).
Claim 14
Dependent Claim
13 words
A dental treatment material comprising a composition as set forth in claim 1.
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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) | 1988-10-21 | 1989-04-22 | 1989-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-21 | 1993-04-22 | 1993-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-21 | 1997-04-22 | 1997-10-22 | $7700.00 | Window Closed / Lapsed |