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US5364890A Expired / Lapsed US ⏱️ 0.0 years remaining

Dental adhesive composition

Assignee: GC Corp
•
Filing: 1993-05-26
•
Granted: 1994-11-15
•
Expires: 2013-05-26
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Abstract

Abstract A compound having a carbodiimide in its molecule is incorporated in a dental adhesive composition. With this composition, dental composite material can be firmly bonded to the enamel and dentin of a tooth, thereby avoiding formation of a gap which may otherwise cause secondary caries.

Inventors

  • 👤 Tetsuro Sakuma
  • 👤 Junichi Okada

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 02:10
CPC Classifications
A; A61; A61K; A61K6/00; A61K6/30

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 169 words
A dental adhesive composition comprising (a) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (b) at least one methacrylate or acrylate selected from the group consisting of methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, 2-hydroxyethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, glycidyl methacrylate, 2-methoxyethyl methacrylate, 2-ethylhexyl methacrylate, 2,2-bis(methacryloxyphenyl)propane, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, 2,2-bis(4-methacryloxydiethoxyphenyl)propane, 2,2-bis(4-methacryloxypropoxy-phenyl)propane, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,3-butanediol methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol methacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol trimethacrylate, trimethylolmethane trimethacrylate, pentaerythritol tetramethacrylate, methacrylates and acrylates containing a urethane bond in their molecules, di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate or its acrylate and compounds having the following structural formula: ##STR3## wherein: R, which may be identical or different from each other is H or CH 3 , and A is --(CH 2 ) 6 --, ##STR4## and (c) a photopolymerization or a chemical polymerization initiator which chemical polymerization initiator is selected from the group consisting of the following combinations: 1) N-phenylglycine and benzoyl peroxide; 2) p-toluenesulfinate and benzoyl peroxide; and 3) p-toluenesulfinate, an aromatic tertiary amine and benzoyl peroxide.
Claim 2
Dependent Claim 169 words
A dental adhesive composition comprising (a) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (b) at least one methacrylate or acrylate selected from the group consisting of methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, 2-hydroxyethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, glycidyl methacrylate, 2-methoxyethyl methacrylate, 2-ethylhexyl methacrylate, 2,2-bis(methacryloxyphenyl)propane, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, 2,2-bis(4-methacryloxydiethoxyphenyl)propane, 2,2-bis(4-methacryloxypropoxy-phenyl)propane, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,3-butanediol methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol methacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol trimethacrylate, trimethylolmethane trimethacrylate, pentaerythritol tetramethacrylate, methacrylates and acrylates containing a urethane bond in their molecules, di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate or its acrylate and compounds having the following structural formula: ##STR3## wherein: R, which may be identical or different from each other is H or CH 3 , and A is --(CH 2 ) 6 --, ##STR4## and (c) a photopolymerization or a chemical polymerization initiator which chemical polymerization initiator is selected from the group consisting of the following combinations: 1) N-phenylglycine and benzoyl peroxide; 2) p-toluenesulfinate and benzoyl peroxide; and 3) p-toluenesulfinate, an aromatic tertiary amine and benzoyl peroxide.
Claim 3
Dependent Claim 31 words
A dental adhesive composition as claimed in claim 1, wherein said 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide is present in an amount of from 0.1 to 20.0% with respect to the total weight of the composition.
Claim 4
Dependent Claim 33 words
A dental adhesive composition as claimed in claim 1, wherein said methacrylate or acrylate is present in an amount of from 50 to 97.4% with respect to the total weight of the composition.
Claim 5
Dependent Claim 15 words
A dental adhesive composition as claimed in claim 1, which further comprises an organic solvent.
Claim 6
Dependent Claim 14 words
A dental adhesive composition as claimed in claim 1, which further comprises a filler.
Claim 7
Dependent Claim 31 words
A dental adhesive composition as claimed in claim 1, wherein said 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide is present in an amount of from 0.5 to 10.0% with respect to the total weight of the composition.
Claim 8
Dependent Claim 20 words
A dental adhesive composition as claimed in claim 1, wherein said methacrylate or acrylate is 2-hydroxyethylmethacrylate or triethylene glycol dimethacrylate.
Claim 9
Dependent Claim 18 words
A dental adhesive composition as claimed in claim 1, wherein said photopolymerization initiator consists of a sensitizer-reducer combination.
Claim 10
Dependent Claim 35 words
A dental adhesive composition as claimed in claim 1, wherein said at least one methacrylate or acrylate is selected from the group consisting of methyl methacrylate, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, 2-hydroxyethyl methacrylate, triethylene glycol dimethacrylate and di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate.
Claim 11
Dependent Claim 14 words
A dental adhesive composition as claimed in claim 1, comprising a chemical polymerization initiator.
Claim 12
Dependent Claim 22 words
A dental adhesive composition as claimed in claim 10, wherein said chemical polymerization initiator is a combination of N-phenylglycine and benzoyl peroxide.
Claim 13
Dependent Claim 24 words
A dental adhesive composition as claimed in claim 1, which provides a bonding strength of greater than or equal to 150 kg/cm 2 .
Claim 14
Dependent Claim 13 words
A dental adhesive composition as claimed in claim 1 comprising a photopolymerization initiator.
Claim 15
Dependent Claim 16 words
A dental adhesive composition as claimed in claim 13, wherein said photopolymerization initiator is camphor quinone.
Claim 16
Dependent Claim 170 words
A dental adhesive composition consisting of (a) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (b) at least one methacrylate or acrylate selected from the group consisting of methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, 2-hydroxyethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, glycidyl methacrylate, 2-methoxyethyl methacrylate, 2-ethylhexyl methacrylate, 2,2-bis(methacryloxyphenyl)propane, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, 2,2-bis(4-methacryloxydiethoxyphenyl)propane, 2,2-bis(4-methacryloxypropoxy-phenyl)propane, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,3-butanediol methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol methacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol trimethacrylate, trimethylolmethane trimethacrylate, pentaerythritol tetramethacrylate, methacrylates and acrylates containing a urethane bond in their molecules, di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate or its acrylate and compounds having the following structural formula: ##STR5## wherein: R, which may be identical or different from each other is H or CH 3 , and A is --(CH 2 ) 6 --, ##STR6## and (c) a photopolymerization or a chemical polymerization initiator which chemical polymerization initiator is selected from the group consisting of the following combinations: 1) N-phenylglycine and benzoyl peroxide; 2) p-toluenesulfinate and benzoyl peroxide; and 3) p-toluenesulfinate, an aromatic tertiary amine and benzoyl peroxide.
Claim 17
Dependent Claim 170 words
A dental adhesive composition consisting of (a) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (b) at least one methacrylate or acrylate selected from the group consisting of methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, 2-hydroxyethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, glycidyl methacrylate, 2-methoxyethyl methacrylate, 2-ethylhexyl methacrylate, 2,2-bis(methacryloxyphenyl)propane, 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, 2,2-bis(4-methacryloxydiethoxyphenyl)propane, 2,2-bis(4-methacryloxypropoxy-phenyl)propane, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,3-butanediol methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol methacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol trimethacrylate, trimethylolmethane trimethacrylate, pentaerythritol tetramethacrylate, methacrylates and acrylates containing a urethane bond in their molecules, di-2-methacryloxyethyl-2,2,4-trimethylhexamethylene dicarbamate or its acrylate and compounds having the following structural formula: ##STR5## wherein: R, which may be identical or different from each other is H or CH 3 , and A is --(CH 2 ) 6 --, ##STR6## and (c) a photopolymerization or a chemical polymerization initiator which chemical polymerization initiator is selected from the group consisting of the following combinations: 1) N-phenylglycine and benzoyl peroxide; 2) p-toluenesulfinate and benzoyl peroxide; and 3) p-toluenesulfinate, an aromatic tertiary amine and benzoyl peroxide.
Claim 18
Dependent Claim 14 words
A dental adhesive composition as claimed in claim 15, comprising a chemical polymerization initiator.
Claim 19
Dependent Claim 22 words
A dental adhesive composition as claimed in claim 16, wherein said chemical polymerization initiator is a combination of N-phenylglycine and benzoyl peroxide.
Claim 20
Dependent Claim 24 words
A dental adhesive composition as claimed in claim 15, which provides a bonding strength of greater than or equal to 150 kg/cm 2 .
Claim 21
Dependent Claim 13 words
A dental adhesive composition as claimed in claim 15 comprising a photopolymerization initiator.
Claim 22
Dependent Claim 16 words
A dental adhesive composition as claimed in claim 19, wherein said photopolymerization initiator is camphor quinone.

References Cited (Backward Citations)

JPS55164611A Cited
US4525493A Cited
US4778471A Cited
US5105010A Cited
US5136006A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-11-14 1998-05-16 1998-11-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-11-14 2002-05-16 2002-11-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-11-14 2006-05-16 2006-11-15 $7700.00 Window Closed / Lapsed

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