Patent US4515930A successfully refreshed from Google Patents.
US4515930A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Highly water-resistant adhesive
Assignee: Kuraray Co Ltd
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Filing: 1984-01-20
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Granted: 1985-05-07
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Expires: 2004-01-20
Abstract
Abstract An adhesive which comprises (a) 1 part by weight of a polymerizable monomer represented by the formula <IMAGE> (where R1 denotes H or CH3; Ra denotes a C6-40 organic residue having a valence of m+1; X1 and X2 denote O, S, or NR' [where R' denotes H or a C1-6 hydrocarbon group], two of X1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), and (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a). This adhesive firmly adheres to hard tissues of the living body such as teeth and bones, metallic materials, organic polymeric materials, and ceramics. It keeps the high adhesive strength for a long period of time under a wet condition. This adhesive is useful particularly in dentistry.
Inventors
- 👤 Ikuo Omura
- 👤 Junichi Yamauchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 17:54
CPC Classifications
C; C08; C08F; C08F246/00; A; A61; A61K; A61K6/00; A61K6/70; A61K6/71; A61K6/76; A61K6/77; C08F230/00; C08F230/02
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
150 words
An adhesive which comprises a polymerizable composition consisting of (a) 1 part by weight of a monomer represented by the formula ##STR28## where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', (where R' denotes H or a C 1-6 hydrocarbon group), two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1, and (b) 0 to 199 parts by weight of a monomer selected from the group consisting of mono-, di-, tri-, and tetrafunctional (meth)acrylates, styrene, divinyl benzene, p-chlorostyrene, (meth)acrylamide or derivatives thereof, N-(hydroxymethyl)acrylamide, (meth)acrylic acid, isobutylvinyl ether, vinyl acetate, diethyl fumarate, diethyl maleate, maleic anhydride, methyl vinyl ketone, allyl chloride, vinyl naphthalene and vinylpyridine or combinations thereof.
Claim 2
Dependent Claim
150 words
An adhesive which comprises a polymerizable composition consisting of (a) 1 part by weight of a monomer represented by the formula ##STR28## where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', (where R' denotes H or a C 1-6 hydrocarbon group), two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1, and (b) 0 to 199 parts by weight of a monomer selected from the group consisting of mono-, di-, tri-, and tetrafunctional (meth)acrylates, styrene, divinyl benzene, p-chlorostyrene, (meth)acrylamide or derivatives thereof, N-(hydroxymethyl)acrylamide, (meth)acrylic acid, isobutylvinyl ether, vinyl acetate, diethyl fumarate, diethyl maleate, maleic anhydride, methyl vinyl ketone, allyl chloride, vinyl naphthalene and vinylpyridine or combinations thereof.
Claim 3
Dependent Claim
12 words
An adhesive as set forth in claim 1, wherein m is 1.
Claim 4
Dependent Claim
22 words
An adhesive as set forth in claim 1, wherein m and k are 1, and X 1 and X 2 are --O--.
Claim 5
Dependent Claim
18 words
An adhesive as set forth in claim 3, wherein the R a is --CH 2 -- n .
Claim 6
Dependent Claim
14 words
An adhesive as set forth in claim 3, wherein the R a is ##STR29##
Claim 7
Dependent Claim
14 words
An adhesive as set forth in claim 3, wherein the R a is ##STR30##
Claim 8
Dependent Claim
14 words
An adhesive as set forth in claim 3, wherein the R a is ##STR31##
Claim 9
Dependent Claim
33 words
An adhesive as set forth in claim 1, wherein a curing agent is incorporated in an amount of 0.01 to 20 parts by weight for 100 parts by weight of the polymerizable monomers.
Claim 10
Dependent Claim
18 words
An adhesive as set forth in claim 8, wherein the curing agent is a redox type polymerization initiator.
Claim 11
Dependent Claim
15 words
An adhesive as set forth in claim 8, wherein the curing agent is a photosensitizer.
Claim 12
Dependent Claim
42 words
An adhesive as set forth in claim 1, wherein a volatile organic solvent having a boiling point lower than 150° C. at 760 Torr is incorporated in an amount of less than 300 times (by weight) the weight of the polymerizable monomers.
Claim 13
Dependent Claim
32 words
An adhesive as set forth in claim 1, wherein a filler is incorporated in an amount of 20 to 500 parts by weight for 100 parts by weight of the polymerizable monomers.
Claim 14
Dependent Claim
28 words
An adhesive as set forth in claim 1, wherein the vinyl monomer (b) is a mono-, di-, tri- or tetra-functional (meth)acrylate, styrene or derivatives thereof or vinyl acetate.
Claim 15
Independent Claim
153 words
A method for restoring a decayed tooth which comprises applying an adhesive to the surface of the tooth cavity and subsequently filling the cavity with a dental filling material composed of a polymerizable monomer, filler and curing agent, said adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR32## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), and (c) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 16
Independent Claim
153 words
A method for restoring a decayed tooth which comprises applying an adhesive to the surface of the tooth cavity and subsequently filling the cavity with a dental filling material composed of a polymerizable monomer, filler and curing agent, said adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR32## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), and (c) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 17
Dependent Claim
45 words
A method as set forth in claim 14, wherein the adhesive is incorporated with a volatile organic solvent having a boiling point lower than 150° C. at 760 Torr in an amount of less than 300 times (by weight) the weight of the polymerizable monomers.
Claim 18
Independent Claim
149 words
A method for restoring a decayed tooth which comprises filling an adhesive in the tooth cavity, said adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR33## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), (c) 20 to 500 parts by weight of filler for 100 parts by weight of the polymerizable monomers, and (d) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 19
Independent Claim
149 words
A method for restoring a decayed tooth which comprises filling an adhesive in the tooth cavity, said adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR33## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), (c) 20 to 500 parts by weight of filler for 100 parts by weight of the polymerizable monomers, and (d) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 20
Independent Claim
156 words
A method of dental treatment which comprises bonding a dental restorative material to teeth or bonding dental restorative materials to each other with an adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR34## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), (c) 20 to 500 parts by weight of filler for 100 parts by weight of the polymerizable monomers, and (d) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 21
Independent Claim
156 words
A method of dental treatment which comprises bonding a dental restorative material to teeth or bonding dental restorative materials to each other with an adhesive comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR34## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), (c) 20 to 500 parts by weight of filler for 100 parts by weight of the polymerizable monomers, and (d) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 22
Independent Claim
135 words
A method for preventing tooth decay which comprises coating the tooth surface with a composition which adheres to the tooth, said composition comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR35## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), and (c) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
Claim 23
Independent Claim
135 words
A method for preventing tooth decay which comprises coating the tooth surface with a composition which adheres to the tooth, said composition comprising (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR35## (where R 1 denotes H or CH 3 ; R a denotes a C 6-40 organic residue having a valence of m+1; X 1 and X 2 denote O, S, or NR', two of X 1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a), and (c) 0.01 to 20 parts by weight of curing agent for 100 parts by weight of the polymerizable monomers.
References Cited (Backward Citations)
US3884864A
Cited
US3809685A
Cited
US4044044A
Cited
US4259117A
Cited
US4222780A
Cited
US4277565A
Cited
US4322509A
Cited
US4442239A
Cited
EP0058483A2
Cited
US4443197A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-05-06 | 1988-11-05 | 1989-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-06 | 1992-11-05 | 1993-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-06 | 1996-11-05 | 1997-05-07 | $7700.00 | Window Closed / Lapsed |