Dental materials using thermoset polymers

Patent metadata

Field	Value
Publication number	US-10925693-B2
Application number	US-202017008382-A
Country	US
Kind code	B2
Filing date	Aug 31, 2020
Priority date	Jul 7, 2015
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

Provided herein are crosslinked polymers useful in orthodontic appliances and light polymerizable liquid compositions and formulations useful for making crosslinked polymers. Also provided are methods of making an orthodontic appliance comprising a cross-linked polymer formed by a direct fabrication technique.

First claim

What is claimed is:

1. A light polymerizable liquid composition comprising:
a first polymerizable component, wherein the first polymerizable component is a urethane (meth)acrylate oligomer;
a second polymerizable component, wherein the second polymerizable component is a vinyl monomer or a thiol monomer;
a filler; and
a photoinitiator,

wherein at least one of the first polymerizable component or the second polymerizable component comprises at least two polymerizable groups.

2. The light polymerizable liquid composition of claim 1 , wherein the filler is selected from the group consisting of: poly(vinyl alcohol), poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate), polycaprolactone, poly(methyl methacrylate), polycaprolactone-block-polytetrahydrofuran block-polycaprolactone, poly(vinyl) chloride, and cellulose acetate butyrate.

3. The light polymerizable liquid composition of claim 1 , wherein the filler is selected from the group consisting of: hydroxyapatite, fumed silica, colloidal silica, a glass powder, and R-tricalciumphosphate.

4. The light polymerizable liquid composition of claim 1 , wherein the viscosity of the light polymerizable liquid composition is less than 4000 cP at 25° C.

5. The light polymerizable liquid composition of claim 1 , wherein:
the amount of the first polymerizable component is from 25 to 50 wt %; and
the amount of the second polymerizable component is from 50 to 75 wt %.

6. The light polymerizable liquid composition of claim 1 , wherein the first polymerizable component is selected from the group consisting of: a urethane dimethacrylate oligomer, an isophorone urethane dimethacrylate oligomer, a urethane diacrylate oligomer, and a urethane triacrylate oligomer.

7. The light polymerizable liquid composition of claim 1 , wherein the first polymerizable component is selected from the group consisting of: a dimethacrylate urethane, an isophorone urethane dimethacrylate, an aliphatic urethane diacrylate oligomer, an aromatic urethane diacrylate oligomer, an aliphatic urethane acrylate oligomer, and an aliphatic trifunctional methacrylate.

8. The light polymerizable liquid composition of claim 1 , wherein the second polymerizable component is an acrylate monomer.

9. The light polymerizable liquid composition of claim 1 , wherein the second polymerizable component is a vinyl monomer not including a urethane linkage.

10. The light polymerizable liquid composition of claim 1 , wherein the second polymerizable component is selected from the group consisting of: 1-vinyl-2-pyrrolidinone, R-carboxyethylacrylate, trimethyl cyclohexyl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, and isobornyl methacrylate.

11. A light polymerizable liquid composition comprising:
a first polymerizable component, wherein the first polymerizable component is a first urethane (meth)acrylate oligomer;
a second polymerizable component, wherein the second polymerizable component is a first vinyl monomer not including a urethane linkage or a first thiol monomer not including a urethane linkage;
a third polymerizable component, wherein the third polymerizable component is a second urethane (meth)acrylate oligomer or a second vinyl monomer not including a urethane linkage, or a second thiol monomer not including a urethane linkage
a filler; and
a photoinitiator,

wherein at least one of the first polymerizable component, the second polymerizable component, or the third polymerizable component comprises at least two polymerizable groups.

12. The light polymerizable liquid composition of claim 11 , wherein the filler is selected from the group consisting of: poly(vinyl alcohol), poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate), polycaprolactone, poly(methyl methacrylate), polycaprolactone-block-polytetrahydrofuran block-polycaprolactone, poly(vinyl) chloride, and cellulose acetate butyrate.

13. The light polymerizable liquid composition of claim 11 , wherein the filler is selected from the group consisting of: hydroxyapatite, fumed silica, colloidal silica, a glass powder, and R-tricalciumphosphate.

14. The light polymerizable liquid composition of claim 11 , wherein the viscosity of the light polymerizable liquid composition is less than 700 cP at 25° C.

15. The light polymerizable liquid composition of claim 11 , wherein:
the amount of the first polymerizable component is from 15 to 40 wt %;
the amount of the second polymerizable component is from 15 to 75 wt %;
the amount of the third polymerizable component is from 2 to 45 wt %; and
the total amount of the first polymerizable component, the second polymerizable component, and the third polymerizable component is greater than or equal to 70 wt %.

16. The light polymerizable liquid composition of claim 11 , wherein the second polymerizable component is a vinyl monomer not including a urethane linkage.

17. The light polymerizable liquid composition of claim 11 , wherein the second polymerizable component is selected from the group consisting of: 1-vinyl-2-pyrrolidinone, R-carboxyethylacrylate, trimethyl cyclohexyl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, and isobornyl methacrylate.

18. The light polymerizable liquid composition of claim 11 , wherein the third polymerizable component is a urethane (meth)acrylate oligomer or a vinyl monomer not including a urethane linkage.

19. The light polymerizable liquid composition of claim 11 , wherein the third polymerizable component is selected from the group consisting of: tris(2-hydroxy ethyl)isocyanurate triacrylate, tricyclodecane dimethanol diacrylate, and tripropylene glycol diacrylate.

20. The light polymerizable liquid composition of claim 11 , wherein the third polymerizable component is a thiol monomer.

Assignees

• Align Technology Inc

Inventors

• Chen Yan
• Li Chunhua
• Kaza Srinivas
• Cramer Neil Brian
• Berard Mary Catherine

Classifications

• B33Y70/00

  Materials specially adapted for additive manufacturing · CPC title

• C08F226/10

  N-Vinyl-pyrrolidone · CPC title

• C08F222/1065

  of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates · CPC title

• C08F220/283 Primary

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title

• B33Y80/00

  Products made by additive manufacturing · CPC title