Patent CH594418A5 successfully refreshed from Google Patents.
US4544467A
Expired / Lapsed
US
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Light-curable dentin and enamel adhesive
Assignee: 3M Co
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Filing: 1983-06-28
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Granted: 1985-10-01
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Expires: 2003-06-28
Abstract
Abstract Light-curable dentin and enamel adhesives comprising phosphorus-containing polymerizable monomer, sulfur compound having sulfur in the +2 or +4 oxidation state, selected photoinitiators, and an optional peroxide compound, as well as one-step and two-step curing methods.
Inventors
- 👤 James E. Bunker
- 👤 Richard P. Fields
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:56
CPC Classifications
A; A61; A61K; A61K6/00; A61K6/60; A61K6/62; A61K6/30; C; C08; C08L; C08L33/00; C08L33/04; C08L33/06; C08L33/062; C08L33/068
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
197 words
A visible light cure dentin and enamel primer composition, comprising: (a) as a first component, phosphorous-containing free-radically polymerizable monomer suitable for use in the oral environment; (b) as a second component, sulfur compound having sulfur in the +2 or +4 oxidation state, said second component acting as a polymerization activator for said first component and enhancing adhesion of said composition to dentin; and (c) as a third component, photoinitiator selected from substituted and unsubstituted alkylphenones, substituted and unsubstituted benzilidene acetophenones, and compounds of the formula: ##STR2## wherein: X is nothing, a carbon-carbon bond, CR 2 , C═ 1 , C═O, S, SO, SO 2 , O, or NR where each R is independently H or a lower alkyl or substituted alkyl group and R 1 is a tetravalent unsaturated aliphatic radical doubly bonded to said C of C═R 1 and bonded to the 4 or 5 position of said Formula I to form a fused ring structure; Y and Z are independently lower alkyl, substituted alkyl, a divalent unsaturated radical bonded to adjacent positions of said Formula I to form a fused ring structure, alkoxy, halogen, or nitro; and m and n are independently zero to 4.
Claim 2
Dependent Claim
197 words
A visible light cure dentin and enamel primer composition, comprising: (a) as a first component, phosphorous-containing free-radically polymerizable monomer suitable for use in the oral environment; (b) as a second component, sulfur compound having sulfur in the +2 or +4 oxidation state, said second component acting as a polymerization activator for said first component and enhancing adhesion of said composition to dentin; and (c) as a third component, photoinitiator selected from substituted and unsubstituted alkylphenones, substituted and unsubstituted benzilidene acetophenones, and compounds of the formula: ##STR2## wherein: X is nothing, a carbon-carbon bond, CR 2 , C═ 1 , C═O, S, SO, SO 2 , O, or NR where each R is independently H or a lower alkyl or substituted alkyl group and R 1 is a tetravalent unsaturated aliphatic radical doubly bonded to said C of C═R 1 and bonded to the 4 or 5 position of said Formula I to form a fused ring structure; Y and Z are independently lower alkyl, substituted alkyl, a divalent unsaturated radical bonded to adjacent positions of said Formula I to form a fused ring structure, alkoxy, halogen, or nitro; and m and n are independently zero to 4.
Claim 3
Dependent Claim
43 words
A composition according to claim 1, wherein said polymerizable monomer contains phosphorus atoms bonded to one or more olefinically unsaturated groups and bonded to one or more chlorine atoms, bromine atoms, active hydrogen atoms, or alkyl, substituted alkyl, allyl, or substituted allyl groups.
Claim 4
Dependent Claim
47 words
A composition according to claim 1, wherein said polymerizable monomer comprises an organic ester of one or more acids of phosphorus, the organic radical of said ester containing at least one free-radically polymerizable functional group, and wherein said ester has chlorine or bromine bonded directly to phosphorus.
Claim 5
Dependent Claim
74 words
A composition according to claim 1, wherein said polymerizable monomer is selected from (a) 2-methacryloxyethyl phenyl phosphate, and (b) halophosphorus ester wherein the organic radical of said ester is the residue remaining after removal of one or more hydroxyl hydrogen atoms from BIS-GMA, phosphorus is doubly bonded to an oxygen atom, is bonded to at least one chlorine atom, and the ratio of said phosphorus to said BIS-GMA is between about 0.015:1 and 1:1.
Claim 6
Dependent Claim
34 words
A composition according to claim 1, wherein said sulfur compound comprises an alkali metal salt or ammonium salt of a sulfinate, sulfite, sulfonate, bisulfite, metabisulfite, or hydrosulfite anion, or the free acid counterpart thereof.
Claim 7
Dependent Claim
17 words
A composition according to claim 1, wherein said sulfur compound comprises sodium benzene sulfinate or para-toluene sulfinate.
Claim 8
Dependent Claim
16 words
A composition according to claim 1, wherein said photoinitiator comprises an alkylphenone or a benzilidene acetophenone.
Claim 9
Dependent Claim
16 words
A composition according to claim 1, wherein said photoinitiator comprises a compound of said Formula I.
Claim 10
Dependent Claim
14 words
A composition according to claim 1, wherein said photoinitiator comprises a xanthone or thioxanthone.
Claim 11
Dependent Claim
11 words
A composition according to claim 1, wherein said photoinitiator comprises 2-chlorothioxanthone.
Claim 12
Dependent Claim
21 words
A composition according to claim 1, further comprising an acyl or alkyl peroxide or hydroperoxide, or a diacyl or dialkyl peroxide.
Claim 13
Dependent Claim
10 words
A composition according to claim 1, further comprising benzoyl peroxide.
Claim 14
Dependent Claim
108 words
A composition according to claim 11, wherein said composition is in two parts, the first of said two parts containing said polymerizable monomer and said peroxide or hydroperoxide, the second of said two parts containing said sulfur compound, and either or both of said two parts containing said photoinitiator, and wherein said polymerizable monomer is about 5 to 95 percent by weight of said composition after said two parts are mixed, said sulfur compound is about 0.5 to 10 percent by weight of said polymerizable monomer, and said photoinitiator and said peroxide or hydroperoxide are each independently about 0.05 to 10 percent by weight of said polymerizable monomer.
Claim 15
Dependent Claim
58 words
A two-part visible light cure dentin primer, one part of which comprises a peroxide compound and the reaction product of BIS-GMA in a diluent with about 0.25 to 10 percent by weight, based on the weight of said BIS-GMA, of phosphorus oxychloride, and the second part of which is a liquid solution comprising alkali benzene sulfinate and 2-chlorothioxanthone.
Claim 16
Dependent Claim
58 words
A two-part visible light cure dentin primer, one part of which comprises a peroxide compound and the reaction product of BIS-GMA in a diluent with about 0.25 to 10 percent by weight, based on the weight of said BIS-GMA, of phosphorus oxychloride, and the second part of which is a liquid solution comprising alkali benzene sulfinate and 2-chlorothioxanthone.
Claim 17
Dependent Claim
64 words
A two-part visible light cure cavity liner, crown preparation or adhesive, one part of which comprises radioopaque filler, a peroxide compound, and the reaction product of BIS-GMA in a diluent with about 0.25 to 10 percent by weight, based on the weight of said BIS-GMA, of phosphorus oxychloride, and the second part of which is a liquid solution comprising alkali benzene sulfinate and 2-chlorothioxanthone.
Claim 18
Dependent Claim
64 words
A two-part visible light cure cavity liner, crown preparation or adhesive, one part of which comprises radioopaque filler, a peroxide compound, and the reaction product of BIS-GMA in a diluent with about 0.25 to 10 percent by weight, based on the weight of said BIS-GMA, of phosphorus oxychloride, and the second part of which is a liquid solution comprising alkali benzene sulfinate and 2-chlorothioxanthone.
References Cited (Backward Citations)
US3066112A
Cited
US3759807A
Cited
US3709866A
Cited
US4071424A
Cited
US4071424B1
Cited
US3827957A
Cited
US3827958A
Cited
US3827956A
Cited
US4110184A
Cited
US3926643A
Cited
US4089762A
Cited
US4368043A
Cited
US4259117A
Cited
US4259075A
Cited
US4182035A
Cited
US4222780A
Cited
US4235633A
Cited
JPS56120610A
Cited
EP0037677A2
Cited
DE3133008A1
Cited
US4350532A
Cited
EP0058483A2
Cited
JPS57143372A
Cited
EP0059649A2
Cited
JPS57167364A
Cited
EP0070634A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-30 | 1989-04-01 | 1989-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-30 | 1993-04-01 | 1993-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-30 | 1997-04-01 | 1997-10-01 | $7700.00 | Window Closed / Lapsed |