Dental composition comprising biphenyl di(meth)acrylate monomer comprising urethane moieties
View Patent ↗Dental compositions and biphenyl di(meth)acrylate monomers are described. The dental compositions comprise at least one biphenyl di(meth)acrylate monomer comprising two aromatic rings connected with a C—C bond wherein the rings each comprise a substituent comprising a urethane moiety and a (meth)acrylate end group.
1. A hardenable dental composition comprising
at least one biphenyl monomer having the general structure
wherein R 2 is independently a halogen or a C 1 to C 4 alkyl group;
m ranges from 0 to 4;
z is an aromatic ring;
t is independently 0;
Q is independently O or S;
L is independently a C 2 to C 12 alkylene group optionally substituted with one or more hydroxyl groups;
n independently ranges from 0 to 10;
L′ is independently a C 2 to C 12 alkylene group; and
R 1 is independently H or methyl.
2. The hardenable dental composition of claim 1 wherein each substituent has a molecular weight of less than 500 g/mole.
3. The hardenable dental composition of claim 1 wherein the substituents further comprise an alkoxy group.
4. The hardenable dental composition of claim 1 wherein the substituents are bonded at an ortho position of the aromatic rings.
5. The hardenable dental composition of claim 1 wherein the biphenyl monomer is a solid at 25° C.
6. The hardenable dental composition of claim 5 wherein the dental composition further comprises at least one other ethylenically unsaturated monomer that is a liquid at 25° C.
7. The hardenable dental composition of claim 1 wherein the biphenyl monomer is a liquid at 25° C.
8. The hardenable dental composition of claim 1 wherein the composition further comprises at least one filler.
9. The hardenable dental composition of claim 8 wherein the filler comprises inorganic nanoparticles.
10. The hardenable dental composition of claim 9 wherein the inorganic nanoparticles comprise silica, zirconia, or mixtures thereof.
11. The hardenable dental composition of claim 9 wherein the nanoparticles are in the form of nanoclusters.
12. The hardenable dental composition of claim 1 wherein Q is oxygen.
13. The hardenable dental composition of claim 1 wherein m is 0.
14. The hardenable dental composition of claim 1 wherein n is 1 and L ranges from C2 to C8.
15. A dental article comprising the hardenable dental composition of claim 1 at least partially hardened.
16. A dental article comprising the hardenable dental composition of claim 1 wherein the composition is in the form self-supporting, malleable structure having a first semi-finished shape.
17. A method of treating a tooth surface, the method comprising providing a hardenable dental composition according to claim 1 , wherein the composition is in the form self-supporting, malleable structure having a first semi-finished shape;
placing the hardenable dental composition on a tooth surface in the mouth of a subject;
customizing the shape of the hardenable dental composition; and
hardening or partially hardening the hardenable dental composition.
18. A biphenyl di(meth)acrylate monomer having the general structure
wherein R 2 is independently Br or a C 1 to C 4 alkyl group;
m ranges from 0 to 4;
z is an aromatic ring;
t is independently 0;
Q is independently O or S;
L is independently a C 2 to C 12 alkylene group optionally substituted with one or more hydroxyl groups;
n independently ranges from 0 to 10; and
wherein R 1 is independently H or methyl.
19. The biphenyl di(meth)acrylate monomer of claim 1 wherein the biphenyl di(meth)acrylate monomer is a liquid at 25° C.