Ultra-low shrinkage composite resins based on blended nematic liquid crystal monomers
First Claim
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1. A resin blend comprising inorganic filler and primary liquid crystal monomer at a ratio to secondary monomer, said ratio and said secondary monomer being adapted to maintain said resin blend in a nematic liquid crystalline state for about 4 hours or more after addition of said inorganic filler at a temperature of 20°
- C., wherein said blend exhibits about 2 vol. % or less polymerization shrinkage, wherein said liquid crystal monomer has the following general structure;
wherein;
R2 is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups;
A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 10 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
R and R4 are acryloyl groups and methacryloyl groups;
wherein said secondary monomer has the following general structure;
whereinn and m independently are selected from the group consisting of from about 2 to about 12; and
R is selected from the group consisting of H and CH3.
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Abstract
Resin blends comprising liquid crystal monomers and secondary monomers useful to blend with liquid crystal monomers to maintain a nematic state under processing conditions while maintaining low cute shrinkage, particularly suitable for use in dental resin composites.
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Citations
91 Claims
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1. A resin blend comprising inorganic filler and primary liquid crystal monomer at a ratio to secondary monomer, said ratio and said secondary monomer being adapted to maintain said resin blend in a nematic liquid crystalline state for about 4 hours or more after addition of said inorganic filler at a temperature of 20°
- C., wherein said blend exhibits about 2 vol. % or less polymerization shrinkage, wherein said liquid crystal monomer has the following general structure;
wherein; R2 is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups;
A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 10 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
R and R4 are acryloyl groups and methacryloyl groups;
wherein said secondary monomer has the following general structure;
wherein n and m independently are selected from the group consisting of from about 2 to about 12; and
R is selected from the group consisting of H and CH3. - View Dependent Claims (2, 3, 4)
- C., wherein said blend exhibits about 2 vol. % or less polymerization shrinkage, wherein said liquid crystal monomer has the following general structure;
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5. A resin blend comprising inorganic filler and primary liquid crystal monomer at a ratio to secondary monomer, said ratio and said secondary monomer being adapted to maintain said resin blend in a nematic liquid crystalline state for about 4 hours or more after addition of said inorganic filler at a temperature of 20°
- C., wherein said blend exhibits about 2 vol. % or less polymerization shrinkage, wherein said liquid crystal monomer has the following general structure;
wherein; R2 is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups;
A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 10 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
R and R4 are acryloyl groups and methacryloyl groups;
wherein said secondary monomer has the following general structure;
- C., wherein said blend exhibits about 2 vol. % or less polymerization shrinkage, wherein said liquid crystal monomer has the following general structure;
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6. A resin blend comprising:
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quantity of primary liquid crystal monomer having the following general structure;
wherein A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 12 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
a quantity of secondary monomer having the following structure;
wherein; X, Y, and Z independently are selected from the group consisting of linear and branched alkyl groups having from about 2 to about 12 carbon atoms;
R1, R3, R6, and R8 are selected from the group consisting of hydrogen atoms and methyl groups;
R2 and R7 independently are selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups; and
,R, R4, R5 and R9 are polymerizable groups selected from the group consisting of nucleophiles and electron deficient alkenes. - View Dependent Claims (7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26)
wherein n and m independently are selected from the group consisting of from about 2 to about 11.
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25. The resin blend of claim 6 wherein the resin blend has a nematic to isotopic transition temperature of about 50°
- C., or more.
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26. The blend of claim 25 wherein the nematic to isotopic transition temperature is about 60°
- C., or more.
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27. A resin blend comprising:
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an amount of primary liquid crystal monomer having the following structure;
wherein A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 12 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
a quantity of secondary monomer having the following structure;
wherein; X, Y, and Z independently are selected from the group consisting of linear and branched alkyl groups having from about 2 to about 12 carbon atoms;
R1, R3, R6, and R8 are selected from the group consisting of hydrogen atoms and methyl groups;
R2 and R7 independently are selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups; and
,R, R4, R5 and R9 are polymerizable groups selected from the group consisting of nucleophiles and electron deficient alkenes. - View Dependent Claims (28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47)
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48. A resin blend comprising:
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an amount of primary liquid crystal monomer having the following general structure;
wherein A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 12 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
a quantity of secondary monomer having the following structure;
wherein; X, Y, and Z independently are selected from the group consisting of linear and branched alkyl groups having from about 2 to about 12 carbon atoms;
R1, R3, R6, and R8 are selected from the group consisting of hydrogen atoms and methyl groups;
R2 and R7 independently are selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups; and
,R, R4, R5 and R9 are polymerizable groups selected from the group consisting of nucleophiles and electron deficient alkenes. - View Dependent Claims (49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69)
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70. A resin blend comprising:
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an amount of primary liquid crystal monomer having the following general structure;
wherein A is selected from the group consisting of branched and linear alkyl groups having from about 2 to about 12 carbon atoms, wherein said branched alkyl groups comprise branches having from about 1 to about 4 carbon atoms; and
a quantity of secondary monomer having the following structure;
wherein; X, Y, and Z independently are selected from the group consisting of linear and branched alkyl groups having from about 2 to about 12 carbon atoms;
R1, R3, R6, and R8 are selected from the group consisting of hydrogen atoms and methyl groups;
R2 and R7 independently are selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups; and
,R, R4, R5 and R9 are polymerizable groups selected from the group consisting of nucleophiles and electron deficient alkenes. - View Dependent Claims (71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91)
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Specification