US4904750A
Expired / Lapsed
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Ester-urethane derivatives of (meth)-acrylic acid for dental materials
Assignee: Bayer AG
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Filing: 1988-12-20
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Granted: 1990-02-27
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Expires: 2008-12-20
Abstract
Abstract Dental fillings, coatings and teeth are formed of polymers and copolymers of a polyfunctional ester-urethane derivative of (meth)-acrylic acid of the formula ##STR1## in which A is a straight-chain or branched aliphatic radical which has 2 to 20 carbon atoms and optionally contains 1 to 3 oxygen bridges, an aromatic radical with 6 to 24 carbon atoms, an araliphatic radical with 7 to 26 carbon atoms or a cycloaliphatic radical with 6 to 26 carbon atoms, r denotes the number of chains starting from A and denotes a number from 2 to 6, R 1 and R 2 are identical and denote hydrogen or are different and denote hydrogen and methyl, n denotes a number from 0 to 5 independently for each chain starting from A, X stands for the group ##STR2## in which Y denotes a divalent (cyclo)aliphatic radical which has 2 to 15 carbon atoms and optionally contains ester, ether or urethane groups, Z denotes a divalent straight-chain or branched aliphatic hydrocarbon radical which has 3 to 15 carbon atoms and can optionally contain 1 to 3 oxygen bridges and can optionally be substituted by 1 to 4 additional (meth)-acrylate radicals and R 3 denotes hydrogen or methyl independently for each chain starting from A.
Inventors
- 👤 Jurgen Reiners
- 👤 Carlhans Suling
- 👤 Walter Schafer
- 👤 Hanns P. Muller
- 👤 Wolfgang Podszun
- 👤 Jens Winkel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 21:33
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; A; A61; A61K; A61K6/00; A61K6/20; A61K6/80; A61K6/884; A61K6/891; A61K6/893; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; C08G18/70; C08G18/72
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
195 words
A polyfunctional ester-urethane derivative of (meth)acrylic acid of the formula ##STR23## in which A is a straight-chain or branched aliphatic radical which has 2 to 20 carbon atoms and optionally contains 1 to 3 oxygen bridges, an aromatic radical with 6 to 24 carbon atoms, an araliphatic radical with 7 to 26 carbon atoms or a cycloaliphatic radical with 6 to 26 carbon atoms, r dentotes the number of chains starting from A and denotes a number from 2 to 6, R 1 and R 2 are identical and denote hydrogen or are different and denote hydrogen and methyl, n denotes a number from 0 to 5 independently for each chain starting from A, X stands for the group ##STR24## in which Y denotes a divalent (cyclo)aliphatic radical which has 2 to 15 carbon atoms and optionally contains ester, ether or urethane groups, Z denotes a divalent straight-chain or branched aliphatic hydrocarbon radical which has 3 to 15 carbon atoms and can optionally contain 1 to 3 oxygen bridges and can optionally be substituted by 1 to 4 additional (meth)-acrylate radicals and R 3 denotes hydrogen or methyl independently for each chain starting from A.
Claim 2
Dependent Claim
195 words
A polyfunctional ester-urethane derivative of (meth)acrylic acid of the formula ##STR23## in which A is a straight-chain or branched aliphatic radical which has 2 to 20 carbon atoms and optionally contains 1 to 3 oxygen bridges, an aromatic radical with 6 to 24 carbon atoms, an araliphatic radical with 7 to 26 carbon atoms or a cycloaliphatic radical with 6 to 26 carbon atoms, r dentotes the number of chains starting from A and denotes a number from 2 to 6, R 1 and R 2 are identical and denote hydrogen or are different and denote hydrogen and methyl, n denotes a number from 0 to 5 independently for each chain starting from A, X stands for the group ##STR24## in which Y denotes a divalent (cyclo)aliphatic radical which has 2 to 15 carbon atoms and optionally contains ester, ether or urethane groups, Z denotes a divalent straight-chain or branched aliphatic hydrocarbon radical which has 3 to 15 carbon atoms and can optionally contain 1 to 3 oxygen bridges and can optionally be substituted by 1 to 4 additional (meth)-acrylate radicals and R 3 denotes hydrogen or methyl independently for each chain starting from A.
Claim 3
Dependent Claim
181 words
A polyfunctional ester-urethane derivative of (meth)acrylic acid according to claim 1, wherein A is a straight-chain or branched aliphatic radical which has 3 to 12 carbon atoms and optionally contains 1 to 3 oxygen bridges, an aromatic radical with 6 to 14 carbon atoms, an araliphatic radical with 7 to 26 carbon atoms or a cycloaliphatic radical with 6 to 14 carbon atoms, r denotes the number of chains starting from A and denotes a number from 2 to 6, R 1 and R 2 are identical and denote hydrogen or are different and denote hydrogen and methyl, n denotes a number from 0 to 5 independently for each chain starting from A, X denotes the group ##STR25## in which Y denotes an alkylene radical with 2 to 10 carbon atoms, Z denotes a divalent straight-chain or branched aliphatic hydrocarbon which has 3 to 10 carbon atoms and can optionally contain 1 or 2 oxygen bridges and can optionally be substituted by 1 or 2 (meth)acrylate radicals and R 3 denotes hydrogen or methyl independently for each chain starting from A.
Claim 4
Dependent Claim
129 words
A polyfunctional ester-urethane derivative of (meth)acrylic acid according to claim 1, wherein A denotes the 2,2-bismethylene-butan-1-yl radical, propane-1,2,3-triyl radical, 2,2-bismethylenepropane-1,3-diyl radical or 3(4), 8(9)-bismethylenetricyclo[5.2.1.0 2 .6 ]decane radical, r denotes the number of chains starting from A and denotes the number 3 or 4, R 1 and R 2 are identical and denote hydrogen or are different and denote hydrogen and methyl, n denotes a number from 0 to 5 independently for each chain starting from A, X denotes the group ##STR26## Z denotes a divalent straight-chain or branched aliphatic hydrocarbon radical which has 3 to 10 carbon atoms and can optinally contain 1 oxygen bridge and can optionally be substituted by 1 (meth)-acrylate radical and R 3 denotes hydrogen or methyl independently for each chain starting from A.
Claim 5
Dependent Claim
100 words
A process for the preparation of a polyfunctional ester-urethane derivative of (meth)-acrylic acid according to claim 1, which comprises reacting a trialkylsilyl ether of a polyol of the formula ##STR27## in which R 4 to R 6 stand for an alkyl radical with 1 to 4 carbon atoms, with an isocyanatocarboxylic acid chloride of the formula ##STR28## in a molar ratio of about 1:1 thereby to form an isocyanato ester, and reacting the isocyanato ester with a (meth)acrylic acid hydroxyalkyl ester of the formula ##STR29## in a molar ratio of OH groups to NCO groups of about 0.98:1 to 1.05:1.
Claim 6
Dependent Claim
31 words
A process according to claim 4, wherein the reaction of the silyl ether with the isocyanato carboxylic acid chloride is carried out at a temperature from about 80° to 150° C.
Claim 7
Dependent Claim
29 words
A process according to claim 4, wherein the reaction of the isocyanato ester with the hydroxyl compound is carried out at a temperature from about 0° to 100° C.
Claim 8
Dependent Claim
14 words
A polymer of a polyfunctional ester-urethane derivative of (meth)-acrylic acid according to claim 1.
Claim 9
Dependent Claim
14 words
A dental filling, coating or tooth formed of a polymer according to claim 7.
Claim 10
Dependent Claim
21 words
A dental filling, coating or tooth according to claim 8, formed of a monomer according to claim 1 and a comonomer.
References Cited (Backward Citations)
US4820745A
Cited
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