Photopolymerizable resin compositions for durable dental prosthetic and restorative articles

A photopolymerizable resin composition for the production and/or repair of dental prosthetic and/or restorative articles, the composition comprising:

• (a) from about 45% to about 70% by weight of one or more first polymerizable acrylic compounds, wherein the one or more first polymerizable acrylic compounds is a urethane di or multi(meth)acrylate derivative of 1,3-bis(isocyanatomethyl)cyclohexane characterized by one of the following formulas:
• in which:
• X is oxygen, nitrogen, or NR1, where:
• R1 is hydrogen, a C1-C14 alkyl group, a C6-C14 cyclic group, C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof;
• R2, R3, R4 and R5 is hydrogen, a C1-C14 alkyl group, a C6-C14 cyclic group, C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof;
• Y is a C1-C14 alkyl group, a C6-C14 cyclic group, a C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof;
• A and B independently of each other stand for one of the following formulas:
• where:
• R6 and R7 is hydrogen, a C1-C14 alkyl group, a C6-C14 cyclic group, a C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof, which can be interrupted by oxygen, sulfur, or otherwise atoms;
• R8 and R9 is a C1-C12 difunctional alkylene, a C1-C12 alkyl group, a C6-C12 cyclic group, a C1-C12 cyclic alkyl group, a C6-C12 aromatic group, a C1-C12 aromatic alkyl group, or any combination thereof, which can be interrupted by oxygen, sulfur, or otherwise atoms;
• R10 is hydrogen, a C1-C14 alkyl group, a C6-C14 cyclic group, a C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof, which can be interrupted by oxygen, sulfur, or otherwise atoms;
• R11 represents a C1-C14 difunctional alkylene, a C1-C14 alkyl group, a C6-C14 cyclic group, a C1-C14 cyclic alkyl group, a C6-C14 aromatic group, a C1-C14 aromatic alkyl group, or any combination thereof, which can be interrupted by oxygen, sulfur, or otherwise atoms;
• and
• R12 represents a C1-C8 trifunctional alkyl group, which can be interrupted by oxygen, sulfur, or otherwise atoms;
• (b) from about 15% to about 40% by weight of one or more second polymerizable acrylic compounds, the one or more second polymerizable acrylic compounds being different from the first polymerizable acrylic compounds;
• (c) from about 2% to about 15% by weight of one or more third polymerizable acrylic compounds, wherein the one or more third polymerizable acrylic compounds is a methacrylate or acrylate compound prepared by reaction of a urethane pre-oligomer with an ethylenically unsaturated monomer;
• (d) from about 2% to about 18% by weight of one or more resin-modifying particles, wherein the one or more resin-modifying particles is selected from the group consisting of organic core-shell impact modifiers and organic-inorganic hybrid core-shell impact modifiers;
• and
• (e) at least about 0.1% by weight of one or more photopolymerization initiators,
• wherein the total composition does not exceed 100% by weight.