Dental compositions comprising nanoparticles providing a refractive index differential between polymerizable resin and filler

Patent metadata

Field	Value
Publication number	US-11246808-B2
Application number	US-201716074655-A
Country	US
Kind code	B2
Filing date	Feb 1, 2017
Priority date	Feb 5, 2016
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

Dental compositions and methods of formulating a dental composition are described. In one embodiment, the dental composition comprises a polymerizable resin comprising one or more ethylenically unsaturated monomers or oligomers and nano-particles. The nanoparticles have a refractive index of at least 1.600 and an average discrete or aggregate particle size of no greater than 100 nm. The dental composition further comprises inorganic metal oxide filler having a discrete or aggregate average particle size of at least 200 nm. The nanoparticles are present at a concentration to provide a refractive index differential between the cured polymerizable resin and inorganic metal oxide filler such that the contrast ratio of the dental composition is at least 40.

First claim

What is claimed is:

1. A dental composition comprising:
a polymerizable resin comprising:
an organic phase comprising:
one or more ethylenically unsaturated polymerizable monomers or oligomers,
wherein the organic phase is homogenous, and

nanoparticles having a refractive index of at least 1.600 and an average discrete or aggregate particle size of no greater than 100 nm; and
inorganic metal oxide filler having a discrete or aggregate average particle size of at least 200 nm,
wherein the nanoparticles are present at a concentration effective to provide a refractive index differential between the polymerizable resin in a cured state and inorganic metal oxide filler such that the contrast ratio of the dental composition is at least 40 and no greater than 70, and
wherein the dental composition is a one-part system comprising the polymerizable resin and inorganic metal oxide filler premixed in the same container.

2. The dental composition of claim 1 wherein the dental composition has a depth of cure of at least 3.5 mm after photocuring at an intensity of 1000 mW/cm 2 for 20 seconds.

3. The dental composition of claim 1 wherein the inorganic metal oxide filler has a refractive index greater than the refractive index of the one or more ethylenically unsaturated monomers or oligomers.

4. The dental composition of claim 1 wherein the inorganic metal oxide filler has a refractive index of at least 1.520.

5. The dental composition of claim 1 wherein the inorganic metal oxide filler comprises nanocluster filler.

6. The dental composition of claim 5 wherein the nanocluster filler comprises aggregated particles of silica nanoparticles and a heavy metal oxide having a refractive index of at least 1.600.

7. The dental composition of claim 1 wherein the dental composition comprises at least 2 wt.-% of the nanoparticles having a refractive index of at least 1.600.

8. The dental composition of claim 1 wherein the nanoparticles comprise an inorganic metal oxide.

9. The dental composition of claim 1 wherein the dental composition comprises an inorganic metal oxide content of at least 70 wt.-%.

10. The dental composition of claim 1 wherein the polymerizable resin comprises at least one monomer comprising at least two (meth)acrylate groups.

11. The dental composition of claim 1 wherein the polymerizable resin further comprises a free-radically cleavable addition-fragmentation agent.

12. The dental composition of claim 11 wherein the addition-fragmentation agent has the formula:

wherein
R 1 , R 2 and R 3 are each independently Z m -Q-, a (hetero)alkyl group or a (hetero)aryl group with the proviso that at least one of R 1 , R 2 and R 3 is Z m -Q-;
Q is a linking group have a valence of m+1;
Z is an ethylenically unsaturated polymerizable group;
m is 1 to 6;
each X 1 is independently —O— or —NR 4 —, where R 4 is H or C 1 -C 4 alkyl; and
n is 0 or 1.

13. The dental composition of claim 12 wherein Z is selected from vinyl, vinyloxy, (meth)acryloxy, (meth)acrylamido, styrenic and acetylenic functional groups.

14. The dental composition of claim 1 wherein the polymerizable resin is substantially free of bisphenol-derived monomers and the cured polymerizable resin inclusive of the nanoparticles has a refractive index that differs from the filler by at least 0.005.

15. The dental composition of claim 14 wherein the composition comprises no greater than 0.05 wt-% of high refractive index pigment particles, the pigment particles having a discrete or aggregate particle size of at least 150 nm.

16. The dental composition of claim 1 wherein the polymerizable resin comprises at least one bisphenol-derived monomers and the cured polymerizable resin inclusive of the nanoparticles has a refractive index that differs from the filler by at least 0.010.

17. The dental composition of claim 16 wherein the composition comprises
no greater than 0.06 wt-% of high refractive index pigment particles, the pigment particles having a discrete or aggregate particle size of at least 150 nm.

18. The dental composition of claim 1 wherein the hardened dental composition exhibits any one or combination of the following properties:
i) a Watts Shrinkage of less than 2%;
ii) a flexural strength of at least 120 MPa;
iii) a flexural modulus of at least 8 GPa; and
v) a radiopacity of at least 3 mm thickness of aluminum.

19. A dental composition of claim 1 ,
the nanoparticles having a refractive index of at least 1.600 and an average particle size of no greater than 100 nm,
the polymerizable resin being substantially free of bisphenol-derived monomer, and
inorganic metal oxide filler having a discrete or aggregate average particle size of at least 200 nm,
wherein the polymerizable resin that is inclusive of the nanoparticles is in a cured state having a refractive index that differs from the filler by at least 0.005.

20. A dental composition of claim 1 , comprising:
the polymerizable resin comprising at least one bisphenol-derived monomer,
the nanoparticles having a refractive index of at least 1.600 and an average particle size of no greater than 100 nm, and
inorganic metal oxide filler having a discrete or aggregate average particle size of at least 200 nm,
wherein the polymerizable resin that is inclusive of the nanoparticles in a cured state has a refractive index that differs from the filler by at least 0.010.

Assignees

• 3M Innovative Properties Co

Inventors

• Craig Bradley D
• Dunbar Timothy D
• Dede Karsten
• Eckert Adrian S
• Abuelyaman Ahmed S
• Kobussen Gregory A
• Thalacker Christoph H
• Homnick Paul J

Classifications

• A61K6/16 Primary

  Refractive index · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/78

  Pigments · CPC title

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title