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    • 10. 发明授权
    • Liquid crystalline (meth)acrylate compounds, composition and method
    • US06339114B1
    • 2002-01-15
    • US09391539
    • 1999-09-08
    • Joachim E. KleeHolger FreyDirk HolterRolf Mulhaupt
    • Joachim E. KleeHolger FreyDirk HolterRolf Mulhaupt
    • A61K6083
    • A61K6/0017A61K6/0023A61K6/0038A61K6/083A61K6/09C07C69/712C07C255/54C08F290/06C08F290/061C08F290/064C08G18/835C08G59/10C08G59/12C08G59/1466C08G59/1494C08G59/4292C08G63/52C08G2270/00C08L67/07C09K19/2028C09K19/3068C09K2019/0448C08L33/00C08L75/16C08L43/02
    • Liquid crystalline (meth)acrylates of the invention include at least three rigid rod-like moieties. One of these moieties is comprised between the (meth)acrylate rests and further two moieties are bonded as side chains. The liquid crystalline (meth)acrylates polymerizable using redox initiators and/or photo initiators. The (meth)acrylates of the invention polymerize quantitative and with very low volume shrinkage of less than 2.5 percent. The invention provides a polymerizable compound within the scope of the general formula: wherein R1 is a group of the general formula —A—, —A—Y1—B—, —A—Y1—B—Y2—C—, or a steroidal moiety, preferably selected of the group of cholesteryl compounds, wherein each A, B and C independently is a substituted or unsubstituted aromatic moiety having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 2 to 24 carbon atoms or a substituted or unsubstituted cycloalkylene moiety having 5 to 30 carbon atoms, a substituted or unsubstituted alkylene moiety having 2 to 20 carbon atoms, each Y1 and Y2 independently is a covalent bond, OCO, N═N, CH═N, C═C, CO, O, S, SO2, O(CO)O, OCS, CH2—O, CH2—S, each L1 and L2 independently is a hydrogen, a alkylene having 1 to 20 carbon atoms or CN, R3 is a covalent bond or a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, oxyalkylene having 1 to 20 carbon atoms, thioalkylene having 1 to 20 carbon atoms or a carboxyalkylene having 1 to 20 carbon atoms, R4 is hydrogen, a substituted or an unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, or aryl rest having 6 to 20 carbon atoms, M is a mesogenic group of the general formula —A—Z, —A—Y1—B—Z, —A—Y1—B—Y2—C—Z, or a steroidal moiety, preferably selected of the group of cholesteryl compounds, wherein each A, B and C independently is a substituted or unsubstituted aromatic moiety having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 2 to 24 carbon atoms or a substituted or unsubstituted cycloalkylene moiety having 5 to 30 carbon atoms, each Y1 and Y2 independently is a covalent bond, OCO, N═N, CH═N, C═C, CO, O, S, SO2, O(CO)O, OCS, CH2—O, CH2—S, each L1 and L2 independently is a hydrogen, a alkylene having 1 to 20 carbon atoms or CN, Z is a hydrogen, halogen, CN, —OR, COOR, NO2, a halogen substituted or unsubstituted alkylene or alkenyl having 1 to 20 carbon atoms, a halogen substituted or unsubstituted oxyalkylene or oxyalkenyl having 1 to 20 carbon atoms, a halogen substituted or unsubstituted thioalkylene or thioalkenyl having 1 to 20 carbon atoms, a halogen substituted or unsubstituted carboxyalkylene or alkanoylenoxy having 1 to 20 carbon atoms, X is a covalent bond, CO, NHCO, OCO and n is an integer from 1 to 10. These compounds are used in dental compositions and methods of use thereof.