Liquid crystalline (meth)acrylate compounds, composition and method

US6339114B1 · kind B1 · utility

Assignee

• DENTSPLY DETREY GMBH · DE

Inventors

• Joachim E. Klee · Radolfzell, DE
• Holger Frey · Emmendingen, DE
• Dirk Hölter · Emmendingen, DE
• Rolf Mulhaupt · Marly, CH

Key dates

• Filing date: Sep 8, 1999
• Grant date: Jan 15, 2002
• Expiry date: Sep 8, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C09K2019/0448
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

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&boxH…