US5808108A
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US
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Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers
Assignee: University of Missouri System
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Filing: 1997-01-15
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Granted: 1998-09-15
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Expires: 2017-01-15
Abstract
Abstract Polymeric compositions are provided which are the reaction product of spiroorthocarbonates and epoxy resins and undergo reduced bulk polymerization shrinkage. The spiroorthocarbonates are of the general formula: <IMAGE> wherein X=O or S; R1, and R2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R3 and R4=-(CH2)n-O-R5; n=1 or 2; R5=alkyl, aryl, substituted aryl, substituted alkyl, <IMAGE> R6=H, alkyl, aryl, substituted alkyl, or substituted aryl; and R7=alkyl, aryl, substituted alkyl, or substituted aryl.
Inventors
- 👤 Cecil C. Chappelow
- 👤 J. David Eick
- 👤 Charles S. Pinzino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:53
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/10; A; A61; A61K; A61K6/00; A61K6/20; A61K6/30; A61K6/80; A61K6/884; A61K6/891; C07D495/00; C07D495/02; C07D495/10; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; G; G03; G03F; G03F7/00; G03F7/004; G03F7/038
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
75 words
A compound of the formula: ##STR13## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR14## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
Claim 2
Dependent Claim
75 words
A compound of the formula: ##STR13## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR14## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
Claim 3
Dependent Claim
25 words
The compound of claim 1, wherein R 1 and R 2 are ethyl and R 3 and R 4 are --CH 2 OCOCH 3 .
Claim 4
Dependent Claim
29 words
The compound of claim 1, wherein R 1 and R 2 are methyl and R 3 and R 4 are --CH 2 OCH 2 C 6 H 5 .
Claim 5
Dependent Claim
25 words
The compound of claim 1, wherein R 1 and R 2 are phenyl and R 3 and R 4 are --CH 2 OOCCH 3 .
Claim 6
Dependent Claim
25 words
The compound of claim 1, wherein R 1 and R 2 are methyl and R 3 and R 4 are --CH 2 OOCCH 3 .
Claim 7
Dependent Claim
27 words
The compound of claim 1, wherein R 1 and R 2 are ethyl and R 3 and R 4 are --CH 2 OOCCH 2 CH 3 .
Claim 8
Dependent Claim
29 words
The compound of claim 1, wherein R 1 and R 2 are ethyl and R 3 and R 4 are --CH 2 OSOOCH 2 CH 2 CH 3 .
Claim 9
Dependent Claim
103 words
A polymeric composition comprising a cationic initiated reaction product of: a spiroorthocarbonate compound, a cationically polymerizable epoxy resin, and a hydroxyl-containing material; said spiroorthiocarbonate compound comprising one or more compounds of the formula: ##STR15## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR16## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
Claim 10
Dependent Claim
103 words
A polymeric composition comprising a cationic initiated reaction product of: a spiroorthocarbonate compound, a cationically polymerizable epoxy resin, and a hydroxyl-containing material; said spiroorthiocarbonate compound comprising one or more compounds of the formula: ##STR15## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR16## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
Claim 11
Dependent Claim
37 words
The composition of claim 8, wherein the hydroxyl-containing material is selected from the group consisting of polyoxyethylene glycols, polyoxypropylene glycols, polytetramethylene oxide glycols, hydroxyethylated cellulose, hydroxypropylated cellulose, hydroxy-terminated polyesters, hydroxy-terminated polyactones, ethoxylated bis-phenol A and hydroxy-terminated polyalkadienes.
Claim 12
Dependent Claim
23 words
The composition of claim 8, wherein said hydroxyl-containing material is selected from the group consisting of 3,4-epoxycyclohexanemethyl-3,4-epoxycyclohexane carboxylate, bis(3,4-epoxycyclohexylmethyleneoxy)adipate, and vinyl cyclohexene dioxide.
Claim 13
Dependent Claim
134 words
A dental composite comprising: a matrix comprising a cationic initiated reaction product of a spiroorthocarbonate compound, a cationically polymerizable epoxy resin, and a hydroxyl-containing material; and a dental filler material dispersed in said matrix in an amount of between about 10 to 90% by weight based on the total weight of the composite, said spiroorthocarbonate compound comprising one or more compounds of the formula: ##STR17## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR18## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
Claim 14
Dependent Claim
134 words
A dental composite comprising: a matrix comprising a cationic initiated reaction product of a spiroorthocarbonate compound, a cationically polymerizable epoxy resin, and a hydroxyl-containing material; and a dental filler material dispersed in said matrix in an amount of between about 10 to 90% by weight based on the total weight of the composite, said spiroorthocarbonate compound comprising one or more compounds of the formula: ##STR17## wherein X=O or S; R 1 and R 2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; R 3 and R 4 =--(CH 2 ) n --O--R 5 ; n=1 or 2; R 5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR18## R 6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R 7 =alkyl, aryl, substituted alkyl, or substituted aryl.
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