Curable composition for use in a high temperature lithography-based photopolymerization process and method of producing crosslinked polymers therefrom

Patent metadata

Field	Value
Publication number	US-11174338-B2
Application number	US-201916403429-A
Country	US
Kind code	B2
Filing date	May 3, 2019
Priority date	May 4, 2018
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

Provided herein are curable compositions for use in a high temperature lithography-based photopolymerization process, a method of producing crosslinked polymers using said curable compositions, crosslinked polymers thus produced, and orthodontic appliances comprising the crosslinked polymers.

First claim

What is claimed is:

1. A curable composition for use in a photopolymerization process, the composition comprising:
a toughness modifier, wherein the toughness modifier is a polymerizable oligomer having a number average molecular weight of greater than 5 kDa, wherein the toughness modifier is the polymerizable oligomer selected from one of Formula (II), (III), (IV), and (V):

wherein:
each R 4 and each R 5 independently represent a divalent, linear, branched or cyclic C 5 -C 15 aliphatic radical;
each R 6 independently represents a divalent, linear or branched C 2 -C 4 alkyl radical;
each R 7 independently represents a divalent, linear, branched C 2 -C 6 alkyl radical, or is absent;
each n is independently an integer from 1 to 10;
each m is independently an integer from 1 to 20;

each o is independently an integer from 5 to 50 or is absent; and
p is an integer from 1 to 40 or is absent; and
a reactive diluent, wherein the reactive diluent is a cycloalkyl 2-((meth)acryloxy)benzoate, wherein the cycloalkyl 2-((meth)acryloxy)benzoate is a cyclopropyl 2-((meth)acryloxy)benzoate, wherein the reactive diluent is a polymerizable compound having a molecular weight of 0.1 to 1.0 kDa and wherein the content of the reactive diluent is such that the viscosity of the composition is 1 to 70 Pa·s at 110° C.

2. The curable composition of claim 1 , wherein the glass transition temperature of the toughness modifier is less than 0° C.

3. The curable composition of claim 1 , wherein the content of the toughness modifier is such that a crosslinked polymer prepared from the composition has an elongation at break greater than or equal to 5% when measured according to ISO 527-2 5B, optionally at a crosshead speed of 5 mm/min.

4. The curable composition of claim 1 , comprising 20 to 50 wt %, based on the total weight of the composition, of the toughness modifier.

5. The curable composition of claim 1 , comprising 5 to 50 wt %, based on the total weight of the composition, of the reactive diluent.

6. The curable composition of claim 1 , further comprising a glass transition temperature modifier that has a higher glass transition temperature than the toughness modifier and that is a polymerizable oligomer having a number average molecular weight of 0.4 to 5 kDa.

7. The curable composition of claim 6 , comprising 5 to 50 wt %, based on the total weight of the composition, of the glass transition temperature modifier.

8. The curable composition of claim 1 , wherein the reactive diluent is monofunctional.

9. The curable composition of claim 1 , wherein the reactive diluent comprises a methacrylate.

10. A curable composition for use in a photopolymerization process, the composition comprising:
a toughness modifier, wherein the toughness modifier is a polymerizable oligomer having a number average molecular weight of greater than 5 kDa, wherein the toughness modifier is the polymerizable oligomer selected from one of Formula (II), (III), (IV), and (V):

wherein:
each R 4 and each R 5 independently represent a divalent, linear, branched or cyclic C 5 -C 15 aliphatic radical;
each R 6 independently represents a divalent, linear or branched C 2 -C 4 alkyl radical;
each R 7 independently represents a divalent, linear, branched C 2 -C 6 alkyl radical, or is absent;
each n is independently an integer from 1 to 10;
each m is independently an integer from 1 to 20;

each o is independently an integer from 5 to 50 or is absent; and
p is an integer from 1 to 40 or is absent; and
a reactive diluent, wherein the reactive diluent is a cycloalkyl 2-((meth)acryloxy)benzoate, wherein the cycloalkyl 2-((meth)acryloxy)benzoate is a cyclopropyl 2-((meth)acryloxy)benzoate, wherein the reactive diluent is a polymerizable compound having a molecular weight of 0.1 to 1.0 kDa and wherein the content of the reactive diluent is such that the viscosity of the composition is less than 70 Pa·s at 90° C.

11. The curable composition of claim 10 , wherein the glass transition temperature of the toughness modifier is less than 0° C.

12. The curable composition of claim 10 , wherein the content of the toughness modifier is such that a crosslinked polymer prepared from the composition has an elongation at break greater than or equal to 5% when measured according to ISO 527-2 5B, optionally at a crosshead speed of 5 mm/min.

13. The curable composition of claim 10 , comprising 20 to 50 wt %, based on the total weight of the composition, of the toughness modifier.

14. The curable composition of claim 10 , comprising 5 to 50 wt %, based on the total weight of the composition, of the reactive diluent.

15. The curable composition of claim 10 , further comprising a glass transition temperature modifier that has a higher glass transition temperature than the toughness modifier and that is a polymerizable oligomer having a number average molecular weight of 0.4 to 5 kDa.

16. The curable composition of claim 15 , comprising 5 to 50 wt %, based on the total weight of the composition, of the glass transition temperature modifier.

17. The curable composition of claim 10 , wherein the reactive diluent is monofunctional.

18. The curable composition of claim 10 , wherein the reactive diluent comprises a methacrylate.

Assignees

• Align Technology Inc

Inventors

• Liska Robert
• Gorsche Christian
• Harakaly György
• Kury Markus
• Stampfl Jürgen
• Dorfinger Peter
• Chen Yan
• Li Chunhua
• Kaza Srinivas

Classifications

• C08G18/815 Primary

  Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen · CPC title

• A61C7/08 Primary

  Mouthpiece-type retainers {or positioners, e.g. for both the lower and upper arch (arch-shaped medicament applicators for teeth or gums A61C19/063; mouthguards for protecting the teeth of sportsmen A63B71/085)} · CPC title

• B22F10/60

  Treatment of workpieces or articles after build-up · CPC title

• B22F10/20

  Direct sintering or melting · CPC title

• B22F10/38

  to achieve specific product aspects, e.g. surface smoothness, density, porosity or hollow structures · CPC title