Photopolymerizable compositions that include alicyclic/aromatic dioxiranes and novel dioxiranyl tetraoxaspiro [5.5] undecanes
AssigneeThe Curators of the University of Missouri
InventorsCecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
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Abstract
A visible light cationically photopolymerizable composition is provided. This composition includes an expanding monomer and a dioxirane. More specifically, the expanding monomer used in this composition is one or more dioxiranyl tetraoxaspiro[5.5]undecanes. The composition of the present invention may be used as a matrix resin for dental restorative materials. Another embodiment of the present invention is various novel dioxiranyl tetraoxaspiro[5.5]undecanes.
Claims16
A dental matrix resin, comprising the mixture of:
- (a) a dioxiranyl 1,5,7,11-tetraoxaspiro[5.5]undecane;
- (b) a dioxirane;
- and
- (c) an initiator capable of initiating cationic polymerization of said resin.
A dental restorative material, comprising the mixture of:
- (a) a dioxiranyl 1,5,7,11-tetraoxaspiro[5.5]undecane;
- (b) a dioxirane;
- (c) an initiator capable of initiating cationic polymerization;
- and
- (d) a dental filler that does not substantially interfere with cationic polymerization.
A method of making a dioxiranyl 1,5,7,11-tetraoxaspiro[5.5]undecane, comprising:
- providing an alkyl substituted unsaturated cyclohexenyl group bonded to a propane diol by a flexible linkage selected from the group consisting of alkylene, oxyalkylene, and alkyleneoxy linkages;
- subjecting said alkyl substituted cyclo to transesterification with a tetra-alkyl-orthocarbonate to obtain an unsaturated 1,5,7,11-tetraoxaspiro[5.5]undecane;
- and
- epoxidizing said unsaturated 1,5,7,11-tetraoxaspiro[5.5]undecane with an organic per-acid to obtain a 1,5,7,11-dioxiranyl tetraoxaspiro[5.5]undecane.
A dioxiranyl 1,5,7,11-tetraoxaspiro[5,5]undecane selected from the group consisting of 3,9-bis(cyclohex-3-enylmethyl)-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[(7-oxabicyclo[4.1.0]hept-3-yl)methyl]-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[(6-methylcyclohex-3-enyl)methyl]-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[(4-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methyl]-1,5,7,11-tetraoxaspiro[5.5]undecane, 8,10,19,20-tetraoxatrispiro[5.2.2.5.2.2]henicosa-2,14-diene, 7,26-dioxatrispiro[bicycle[4.1.0]heptane-3,5′-1,3-dioxane-2′2″-1,3-dioxane-5″,4′″-bicyclo[4.1.0]heptane], 3,9-bis(cyclohex-3-enylmethoxy) -1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[(7-oxabicyclo[4.1.0]hept-3-yl)methoxy]-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[2-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methoxy]-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis[(4-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methoxy]-1,5,7,11-tetraoxaspiro[5.5]undecane, 3,9-bis(cyclohex-3-enyloxymethyl)-1,5,7,11-tetraoxaspiro[5.5]undecane, and 3,9-bis[7-oxabicyclo[4.1.0]hept-3-yl)oxymethyl]-1,5,7,11-tetraoxaspiro[5.5]undecane.
Dependencies are inferred from the claim text.