Novel spiroorthocarbonates

A dental restorative material, comprising:

• (A) a matrix comprising a resin comprised of:
• (a) a vinyl ether;
• and
• (b) a photoinitiator system comprising:
• (i) an iodonium salt;
• (ii) a visible light sensitizer;
• and
• (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential greater than or equal to that of N,N-dimethylaniline in a standard solution of 2.9×10−5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×10−5 moles/g camphorquinone in 2-butanone;
• and
• (B) a dental filler dispersed in said matrix in an amount of between about 10 to 90% by weight based on the total weight of the dental restorative material.

A compound of the formula:

• 45
• wherein
• R1-R8 are independently selected from the group consisting of hydrogen;
• alkyl;
• aryl;
• substituted alkyl;
• substituted aryl;
• 6-oxabicyclo[3.1.0]hex-2-yl;
• 6-oxabicyclo[3.1.0]hex-3-yl;
• (6-oxabicyclo[3.1.0]hex-2-yl)methyl;
• (6-oxabicyclo[3.1.0]hex-3-yl)methyl;
• (6-oxabicyclo[3.1.0]hex-2-yl)methoxy;
• (6-oxabicyclo[3.1.0]hex-3-yl)methoxy;
• 7-oxabicyclo[4.1.0]hept-2-yl;
• 7-oxabicyclo[4.1.0]hept-3-yl;
• (7-oxabicyclo[4.1.0]hept-2-yl)methyl;
• (7-oxabicyclo[4.1.0]hept-3-yl)methyl;
• (7-oxabicyclo[4.1.0]hept-2-yl)methoxy;
• (7-oxabicyclo[4.1.0]hept-3-yl)methoxy;
• and —(CH2)n—O—(O═C)—R9, where n=1 through 9 and R9=H, alkyl, aryl, substituted alkyl and substituted aryl, or
• R1•R2, R2•R3, R5•R6, and R6•R7 are independently selected from the group consisting of —CH2(CH2)nCH2— where n=3, 4, 5, and 6 and —CH2-epoxy-(CH2)n—CH2— where n=0, 1, and 2, and —O— so as to form an alicyclic ring or an oxirane ring between R1 and R2, R2 and R3, R5 and R6, or R6 and R7;
• provided that
• R1, R4, R5, and R8 are hydrogen when R2 is independently selected from the group consisting of 6-oxabicyclo[3.1.0]hex-2-yl, 6-oxabicyclo[3.1.0]hex-3-yl, (6-oxabicyclo[3.1.0]hex-2-yl)methyl, (6-oxabicyclo[3.1.0]hex-3-yl)methyl, (6-oxabicyclo[3.1.0]hex-2-yl)methoxy, (6-oxabicyclo[3.1.0]hex-3-yl)methoxy, 7-oxabicyclo[4.1.0]hept-2-yl, 7-oxabicyclo[4.1.0]hept-3-yl, (7-oxabicyclo[4.1.0]hept-2-yl)methyl, (7-oxabicyclo[4.1.0]hept-3-yl)methyl, (7-oxabicyclo[4.1.0]hept-2-yl)methoxy, (7-oxabicyclo[4.1.0]hept-3-yl)methoxy, and R3, R6, and R7 are independently selected from the group consisting of hydrogen, alkyl, aryl, substituted alkyl, and substituted aryl;
• R1, R4, R5, and R8 are hydrogen when R2 and R3 are independently selected from the group consisting of 6-oxabicyclo[3.1.0]hex-2-yl, 6-oxabicyclo[3.1.0]hex-3-yl, (6-oxabicyclo[3.1.0]hex-2-yl)methyl, (6-oxabicyclo[3.1.0]hex-3-yl)methyl, (6-oxabicyclo[3.1.0]hex-2-yl)methoxy, (6-oxabicyclo[3.1.0]hex-3-yl)methoxy, 7-oxabicyclo[4.1.0]hept-2-yl, 7-oxabicyclo[4.1.0]hept-3-yl, (7-oxabicyclo[4.1.0]hept-2-yl)methyl, (7-oxabicyclo[4.1.0]hept-3-yl)methyl, (7-oxabicyclo[4.1.0]hept-2-yl)methoxy, (7-oxabicyclo[4.1.0]hept-3-yl)methoxy, and R3 and R7 are independently selected from the group consisting of hydrogen, alkyl, aryl, substituted alkyl, and substituted aryl;
• R3, R4, R5, R6, R7, and R8 are independently selected from the group consisting of the group consisting of hydrogen, alkyl, aryl, substituted alkyl, and substituted aryl, when R1•R2 =—O— so as to form an oxirane ring between R1 and R2;
• R3, R4, R7, and R8 are independently selected from the group consisting of the group consisting of hydrogen, alkyl, aryl, substituted alkyl, and substituted aryl, when R1•R2 and R5•R6=—O— so as to form an oxirane ring between R1 and R2 and between R5 and R6;
• R1, R4, R5, and R8 are hydrogen when R2 and R3 are ethyl and R6•R7 are —CH2-epoxy-(CH2)n—CH2— where n=1 and 2 so as to form an alicyclic ring between R6and R7;
• and
• R1, R4, R5, and R8 are hydrogen when R2•R3 and R6•R7 are —CH2-epoxy-(CH2)n—CH2— where n=1 and 2 so as to form an alicyclic ring between R2 and R3 and R6 and R7.