US4539382A
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Adhesive composition
Assignee: Kuraray Co Ltd
•
Filing: 1983-08-22
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Granted: 1985-09-03
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Expires: 2003-08-22
Abstract
Abstract An adhesive composition comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 100 parts by weight of a compound represented by general formula I or II: <IMAGE> (I) <IMAGE> (II) where R1 and R1' each stand for hydrogen or a methyl group, R2 stands for a divalent organic residue having 4 to 40 carbon atoms, X1 and X2 each stand for -O-, -S- or -NH-, a is 0 or 1, and R3 stands for a group of the formula <IMAGE> having 6 to 40 carbon atoms, where R4 and R4' each stand for a hydrocarbon group having 1 to 29 carbon atoms, and optionally replaced by a halogen atom, or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for -O-, -COO- or -NH-, a plurality of R4' (when b is 2 or 3) being the same or different, at least one of R4 and R4' having at least three carbon atoms, and (b) 0 to 98.5 parts by weight of a vinyl monomer copolymerizable with the above compound; and 0.01 to 20 parts by weight of a curing agent. It shows a superior adhesive strength on any of hard tissues in a living body, such as teeth and bones, metals, organic polymers and ceramics. It maintains a high adhesive strength for a long time even if it is exposed to moisture, or immersed in water. It is particularly effective for use in dentistry, though it is useful for a variety of other purposes, too.
Inventors
- 👤 Ikuo Omura
- 👤 Junichi Yamauchi
- 👤 Yoshinori Nagase
- 👤 Fumiko Uemura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 06:22
CPC Classifications
C; C09; C09J; C09J4/00; A; A61; A61K; A61K6/00; A61K6/70; A61K6/71; A61K6/76; A61K6/77; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091
Claims Analysis
Total Claims: 94
Claim 1
Independent Claim
241 words
A method of restoring a carious tooth, comprising: applying to the wall surface of a cavity in a carious tooth an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I and II: ##STR155## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR156## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 50 to 98.5 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent; and filling said cavity with a dental filling composition comprising a polymerizable monomer, a filler and a curing agent.
Claim 2
Independent Claim
241 words
A method of restoring a carious tooth, comprising: applying to the wall surface of a cavity in a carious tooth an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I and II: ##STR155## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR156## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 50 to 98.5 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent; and filling said cavity with a dental filling composition comprising a polymerizable monomer, a filler and a curing agent.
Claim 3
Dependent Claim
18 words
A method as set forth in claim 1, wherein said compound is a compound represented by formula I.
Claim 4
Dependent Claim
126 words
A method as set forth in claim 2, wherein R 2 stands for (a) a hydrocarbon group having 4 to 30 carbon atoms which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, or (b) a group having 4 to 30 carbon atoms, and comprising two to seven hydrocarbon groups bonded to one another by a linkage selected from the group consisting of ether, thioether, ester, thioester, thiocarbonyl, amide, urethane, carbonyl and sulfonyl linkages, each of said two to seven hydrocarbon group having 1 to 29 carbon atoms, being unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, wherein at least one of said two to seven hydrocarbon groups having at least three carbon atoms.
Claim 5
Dependent Claim
97 words
A method as set forth in claim 3, wherein R 2 is represented by the formula --R 5 --Y--R 5 ')-- c where R 5 and R 5 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, at least one of R 5 and R 5 ' having at least three carbon atoms, Y stands for ##STR157## and c is an integer of 1 to 6, a plurality of R 5 ' being the same or different.
Claim 6
Dependent Claim
69 words
A method as set forth in claim 3, wherein R 2 is represented by the formula ##STR158## where Y and and Y' each stand for ##STR159## d is an integer of 0 to 3, and R 6 and R 6 ' each stand for a hydrocarbon group having 1 to 27 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group.
Claim 7
Dependent Claim
22 words
A method as set forth in claim 3, wherein X 1 and X 2 both stand for --O--, and a is 1.
Claim 8
Dependent Claim
22 words
A method as set forth in claim 4, wherein X 1 and X 2 both stand for --O--, and a is 1.
Claim 9
Dependent Claim
22 words
A method as set forth in claim 5, wherein X 1 and X 2 both stand for --O--, and a is 1.
Claim 10
Dependent Claim
49 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR160## where R 7 and R 7 ' each stand for a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 11
Dependent Claim
50 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR161## where R 8 stands for hydrogen or a methyl group, and R 9 stands for a hydrocarbon group having 3 to 28 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 12
Dependent Claim
46 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR162## where R 10 stands for a hydrocarbon group having 1 to 12 carbon atoms, which is unsubstituted or substituted by a halogen atom, and e is 0 or 1.
Claim 13
Dependent Claim
29 words
A method as set forth in claim 6, wherein R 2 is represented by the formula --CH 2 -- f where f is an integer of 4 to 20.
Claim 14
Dependent Claim
35 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR163## where h is an integer of 1 to 5, and i is an integer of 0 to 3.
Claim 15
Dependent Claim
17 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR164##
Claim 16
Dependent Claim
40 words
A method as set forth in claim 6, wherein R 2 is represented by the formula ##STR165## where R 11 stands for a hydrocarbon group having 2 to 6 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 17
Dependent Claim
17 words
A method as set forth in claim 6, wherein R 2 is represented by the formula: ##STR166##
Claim 18
Dependent Claim
30 words
A method as set forth in claim 10, wherein R 2 is represented by the formula ##STR167## where g is an integer of 1 to 20, or the formula ##STR168##
Claim 19
Dependent Claim
29 words
A method as set forth in claim 12, wherein R 2 is represented by the formula --CH 2 -- j where j is an integer of 5 to 12.
Claim 20
Dependent Claim
17 words
A method as set forth in claim 14, wherein R 2 is represented by the formula ##STR169##
Claim 21
Independent Claim
20 words
A method as set forth in any of claims 9 to 19, wherein R 1 stands for a methyl group.
Claim 22
Dependent Claim
40 words
A method as set forth in claim 7, wherein R 2 is represented by the formula ##STR170## where R 12 stands for a hydrocarbon group having 1 to 12 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 23
Dependent Claim
15 words
A method as set forth in claim 21, wherein Y stands for --O-- or --COO--.
Claim 24
Dependent Claim
45 words
A method as set forth in claim 7, wherein R 2 is represented by the formula ##STR171## where R 13 and R 13 ' each stand for a hydrocarbon group having 1 to 6 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 25
Dependent Claim
50 words
A method as set forth in claim 7, wherein R 2 is represented by the formula: ##STR172## where R 14 and R 14 ' each stand for hydrogen or a methyl group, and k and k' are both a real number greater than 1, and up to and including 3.
Claim 26
Dependent Claim
29 words
A method as set forth in claim 7, wherein R 2 is represented by the formula ##STR173## where r and r' are both an integer of 2 to 6.
Claim 27
Dependent Claim
17 words
A method as set forth in claim 23, wherein R 2 is represented by the formula: ##STR174##
Claim 28
Dependent Claim
17 words
A method as set forth in claim 23, wherein R 2 is represented by the formula: ##STR175##
Claim 29
Dependent Claim
23 words
A method as set forth in claim 23, wherein R 2 is represented by the formula: ##STR176## where l is 3 or 4.
Claim 30
Independent Claim
20 words
A method as set forth in any of claims 21 to 28, wherein R 1 stands for a methyl group.
Claim 31
Dependent Claim
42 words
A method as set forth in claim 8, wherein R 2 is represented by the formula: ##STR177## where R 6 and R 6 ' are as defined above, m is 0 or 1, and n is an integer of 0 to 3.
Claim 32
Dependent Claim
24 words
A method as set forth in claim 30, wherein at least one of R 6 and R 6 ' is an aromatic hydrocarbon group.
Claim 33
Dependent Claim
17 words
A method as set forth in claim 30 or 31, wherein R 1 is a methyl group.
Claim 34
Dependent Claim
18 words
A method as set forth in claim 1, wherein said compound is a compound represented by formula II.
Claim 35
Dependent Claim
21 words
A method as set forth in claim 33, wherein R 4 is represented by the formula --CH 2 CHCH 2 --.
Claim 36
Dependent Claim
28 words
A method as set forth in claim 1, wherein said vinyl monomer is a monomer selected from the group consisting of (meth)acrylate monomers, styrene monomers and vinyl acetate.
Claim 37
Dependent Claim
23 words
A method as set forth in claim 35, wherein said (meth)acrylate monomers are mono- to tetrafunctional (meth)acrylates having 1 to 66 carbon atoms.
Claim 38
Dependent Claim
35 words
A method as set forth in claim 35, wherein said styrene monomers are represented by the formula ##STR178## where Q stands for a halogen atom, or a hydrocarbon group having 1 to 6 carbon atoms.
Claim 39
Dependent Claim
50 words
A method as set forth in claim 1, wherein said adhesive composition further contains a volatile organic solvent having a boiling point up to 150° C. at 760 Torr, said solvent having a proportion by weight which is a maximum of 300 times greater than that of said polymerizable monomer.
Claim 40
Dependent Claim
19 words
A method as set forth in claim 1, wherein said curing agent is an agent of the redox type.
Claim 41
Dependent Claim
37 words
A method as set forth in claim 39, wherein said curing agent is a ternary agent composed of (a) a salt of an organic sulfinic acid, (b) an amine or a salt thereof, and (c) a peroxide.
Claim 42
Independent Claim
222 words
A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I and II: ##STR179## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR180## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and (b) 50 to 98.5 parts by weight of a vinyl monomer copolymerizable with said compound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 43
Independent Claim
222 words
A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I and II: ##STR179## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR180## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and (b) 50 to 98.5 parts by weight of a vinyl monomer copolymerizable with said compound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 44
Dependent Claim
18 words
A method as set forth in claim 41, wherein said compound is a compound represented by formula I.
Claim 45
Dependent Claim
127 words
A method as set forth in claim 42, wherein R 2 stands for (a) a hydrocarbon group having 4 to 30 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, or (b) a group having 4 to 30 carbon atoms, and composed of two to seven hydrocarbon groups bonded to one another by a linkage selected from the group consisting of ether, thioether, ester, thioester, thiocarbonyl, amide, urethane, carbonyl and sulfonyl linkages, each of said two to seven hydrocarbon groups having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, at least one of said two to seven hydrocarbon groups having at least three carbon atoms.
Claim 46
Dependent Claim
97 words
A method as set forth in claim 43, wherein R 2 is represented by the formula --R 5 --Y--R 5 '-- c where R 5 and R 5 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, at least one of R 5 and R 5 ' having at least three carbon atoms, Y stands for ##STR181## and c is an integer of 1 to 6, a plurality of R 5 ' being the same or different.
Claim 47
Dependent Claim
68 words
A method as set forth in claim 43, wherein R 2 is represented by the formula ##STR182## where Y and Y' each stand for ##STR183## d is an integer of 0 to 3, and R 6 and R 6 ' each stand for a hydrocarbon group having 1 to 27 carbon atoms which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group.
Claim 48
Dependent Claim
22 words
A method as set forth in claim 43, wherein both X 1 and X 2 stand for --O--, and a is 1.
Claim 49
Dependent Claim
22 words
A method as set forth in claim 44, wherein both X 1 and X 2 stand for --O--, and a is 1.
Claim 50
Dependent Claim
22 words
A method as set forth in claim 45, wherein both X 1 and X 2 stand for --O--, and a is 1.
Claim 51
Dependent Claim
51 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR184## where R 7 and R 7 ' each stand for a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, which is unsubstituted or substituted by a hydrogen or halogen atom.
Claim 52
Dependent Claim
50 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR185## where R 8 stands for hydrogen or a methyl group, and R 9 stands for a hydrocarbon group having 3 to 28 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 53
Dependent Claim
46 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR186## where R 10 stands for a hydrocarbon group having 1 to 12 carbon atoms, which is unsubstituted or substituted by a halogen atom, and e is 0 or 1.
Claim 54
Dependent Claim
29 words
A method as set forth in claim 46, wherein R 2 is represented by the formula --CH 2 -- f where f is an integer of 4 to 20.
Claim 55
Dependent Claim
35 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR187## where h is an integer of 1 to 5, and i is an integer of 0 to 3.
Claim 56
Dependent Claim
17 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR188##
Claim 57
Dependent Claim
40 words
A method as set forth in claim 46, wherein R 2 is represented by the formula ##STR189## where R 11 stands for a hydrocarbon group having 2 to 6 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 58
Dependent Claim
17 words
A method as set forth in claim 46, wherein R 2 is represented by the formula: ##STR190##
Claim 59
Dependent Claim
30 words
A method as set forth in claim 50, wherein R 2 is represented by the formula ##STR191## where g is an integer of 1 to 20, or the formula ##STR192##
Claim 60
Dependent Claim
29 words
A method as set forth in claim 52, wherein R 2 is represented by the formula --CH 2 -- j where j is an integer of 5 to 12.
Claim 61
Dependent Claim
17 words
A method as set forth in claim 54, wherein R 2 is represented by the formula ##STR193##
Claim 62
Independent Claim
20 words
A method as set forth in any of claims 49 to 59, wherein R 1 stands for a methyl group.
Claim 63
Dependent Claim
40 words
A method as set forth in claim 47, wherein R 2 is represented by the formula ##STR194## where R 12 stands for a hydrocarbon group having 1 to 12 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 64
Dependent Claim
16 words
A method as set forth in claim 61, where in Y stands for --O-- or --COO--.
Claim 65
Dependent Claim
45 words
A method as set forth in claim 47, wherein R 2 is represented by the formula ##STR195## where R 13 and R 13 ' each stand for a hydrocarbon group having 1 to 6 carbon atoms, which is unsubstituted or substituted by a halogen atom.
Claim 66
Dependent Claim
49 words
A method as set forth in claim 47, wherein R 2 is represented by the formula: ##STR196## where R 14 and R 14 ' stand for hydrogen or a methyl group, and k and k' are both a real number greater than 1, and up to and including 3.
Claim 67
Dependent Claim
28 words
A method as set forth in claim 47, where R 2 is represented by the formula ##STR197## where r and r' are an integer of 2 to 6.
Claim 68
Dependent Claim
17 words
A method as set forth in claim 63, wherein R 2 is represented by the formula: ##STR198##
Claim 69
Dependent Claim
16 words
A method as set forth in claim 63, wherein R 2 is represented by formula: ##STR199##
Claim 70
Dependent Claim
23 words
A method as set forth in claim 63, wherein R 2 is represented by the formula: ##STR200## where l is 3 or 4.
Claim 71
Independent Claim
20 words
A method as set forth in any of claims 61 to 68, wherein R 1 stands for a methyl group.
Claim 72
Dependent Claim
42 words
A method as set forth in claim 48, wherein R 2 is represented by the formula: ##STR201## where R 6 and R 6 ' are as defined above, m is 0 or 1, and n is an integer of 0 to 3.
Claim 73
Dependent Claim
24 words
A method as set forth in claim 70, wherein at least one of R 6 and R 6 ' is an aromatic hydrocarbon group.
Claim 74
Dependent Claim
17 words
A method as set forth in claim 70 or 71, wherein R 1 is a methyl group.
Claim 75
Dependent Claim
18 words
A method as set forth in claim 41, wherein said compound is a compound represented by formula II.
Claim 76
Dependent Claim
21 words
A method as set forth in claim 73, wherein R 4 is represented by the formula --CH 2 CHCH 2 --.
Claim 77
Dependent Claim
28 words
A method as set forth in claim 41, wherein said vinyl monomer is a monomer selected from the group consisting of (meth)acrylate monomers, styrene monomers and vinyl acetate.
Claim 78
Dependent Claim
23 words
A method as set forth in claim 75, wherein said (meth)acrylate momomers are mono- to tetrafunctional (meth)acrylates having 1 to 66 carbon atoms.
Claim 79
Dependent Claim
35 words
A method as set forth in claim 75, wherein said styrene monomers are represented by the formula ##STR202## where Q stands for a halogen atom, or a hydrocarbon group having 1 to 6 carbon atoms.
Claim 80
Dependent Claim
21 words
A method as set forth in claim 41, wherein said filler is a silanated inorganic filler, or an organic-inorganic composite filler.
Claim 81
Dependent Claim
19 words
A method as set forth in claim 41, wherein said curing agent is an agent of the redox type.
Claim 82
Dependent Claim
37 words
A method as set forth in claim 79, wherein said curing agent is a ternary agent composed of (a) a salt of an organic sulfinic acid, (b) an amine or a salt thereof, and (c) a peroxide.
Claim 83
Independent Claim
240 words
A method of restoring a carious tooth, comprising: applying to the wall surface of a cavity in a carious tooth an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I and II: ##STR203## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR204## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent; and filling said cavity with a dental filling composition comprising a polymerizable monomer, a filler and a curing agent.
Claim 84
Independent Claim
240 words
A method of restoring a carious tooth, comprising: applying to the wall surface of a cavity in a carious tooth an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I and II: ##STR203## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR204## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent; and filling said cavity with a dental filling composition comprising a polymerizable monomer, a filler and a curing agent.
Claim 85
Independent Claim
230 words
A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I and II: ##STR205## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR206## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compoound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 86
Independent Claim
230 words
A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I and II: ##STR205## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR206## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compoound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 87
Independent Claim
233 words
A method for dental treatment which comprises bonding either a tooth and a dental restorative material or dental restorative materials to each other by employing an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II: ##STR207## wherein R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR208## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 88
Independent Claim
233 words
A method for dental treatment which comprises bonding either a tooth and a dental restorative material or dental restorative materials to each other by employing an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II: ##STR207## wherein R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR208## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound; 20 to 500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 89
Independent Claim
239 words
A method for dental treatment which comprises bonding either a tooth and a dental restorative material or dental restorative materials to each other by employing an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II: ##STR209## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR210## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound; 20-500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 90
Independent Claim
239 words
A method for dental treatment which comprises bonding either a tooth and a dental restorative material or dental restorative materials to each other by employing an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II: ##STR209## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR210## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R 4 ' being the same or different, at least one R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound; 20-500 parts by weight of a filler; and 0.01 to 20 parts by weight of a curing agent.
Claim 91
Independent Claim
222 words
A method for protecting teeth against dental caries which comprises coating the tooth surface using a pit and a fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II: ##STR211## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR212## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.
Claim 92
Independent Claim
222 words
A method for protecting teeth against dental caries which comprises coating the tooth surface using a pit and a fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II: ##STR211## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR212## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.
Claim 93
Independent Claim
222 words
A method protecting teeth against dental caries which comprises coating the tooth surface using a pit and fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II: ##STR213## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR214## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.
Claim 94
Independent Claim
222 words
A method protecting teeth against dental caries which comprises coating the tooth surface using a pit and fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II: ##STR213## where R 1 and R 1 ' each stand for hydrogen or a methyl group, R 2 stands for a divalent organic residue having 4 to 40 carbon atoms, X 1 and X 2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R 3 stands for a group of the formula ##STR214## having 6 to 40 carbon atoms, where R 4 and R 4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R 4 ' being the same or different, at least one of R 4 and R 4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.
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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) | 1988-09-02 | 1989-03-04 | 1989-09-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-02 | 1993-03-04 | 1993-09-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-02 | 1997-03-04 | 1997-09-03 | $7700.00 | Window Closed / Lapsed |