Process for producing a dental shaped part by stereolithography

Patent metadata

Field	Value
Publication number	US-9387056-B2
Application number	US-201314391524-A
Country	US
Kind code	B2
Filing date	Apr 11, 2013
Priority date	Apr 11, 2012
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

The invention relates to the use of a composite resin composition comprising
(a) at least one polyreactive binder, (b) a first photopolymerization initiator having an absorption maximum at a wavelength of less than 400 nm, (c) a second photopolymerization initiator having an absorption maximum at a wavelength of at least 400 nm and (d) an absorber having an absorption maximum at a wavelength of less than 400 nm,

for the stereolithographic production of a dental shaped part based on composite resin.

The invention also relates to a process for the stereolithographic production of a dental shaped part and the use of the composite resin composition in this process.

First claim

The invention claimed is:

1. A process for producing a dental shaped part, which process comprises curing a composite resin composition comprising
(a) at least one polyreactive binder,
(b) a first photopolymerization initiator having an absorption maximum at a wavelength of less than 400 nm,
(c) a second photopolymerization initiator having an absorption maximum at a wavelength of at least 400 nm and
(d) an absorber having an absorption maximum at a wavelength of less than 400 nm,
by means of stereolithography, wherein
(i) the composite resin composition is cured in layers by the local introduction of radiation the emission maximum of which is at a wavelength of less than 400 nm to form a three-dimensional body, and
(ii) the obtained three-dimensional body is further cured by the introduction of radiation the emission maximum of which is at a wavelength of at least 400 nm.

2. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the first photopolymerization initiator is at a wavelength of less than 400 nm.

3. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the first photopolymerization initiator is at a wavelength in the range of from 360 to less than 400 nm.

4. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the second photopolymerization initiator is at a wavelength of at least 400 nm.

5. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the second photopolymerization initiator is at a wavelength in the range of from 400 to 500 nm.

6. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the absorber is at a wavelength of less than 400 nm.

7. The process according to claim 1 , wherein the longest-wavelength absorption maximum of the absorber is at a wavelength in the range of from 330 to less than 400 nm.

8. The process according to claim 1 , wherein the difference between the absorption maxima of the first and second photopolymerization initiators is at least 5 nm.

9. The process according to claim 1 , wherein the composition comprises a first photopolymerization initiator selected from the group consisting of phosphine oxides, benzoins, benzil ketals, acetophenones, benzophenones, thioxanthones as well as mixtures thereof.

10. The process according to claim 1 , wherein the composition comprises a second photopolymerization initiator selected from the group consisting of α-diketones, acylgermanium compounds, metallocenes as well as mixtures thereof.

11. The process according to claim 10 , wherein the second photopolymerization initiator is selected from the group consisting of α-diketones consisting of camphorquinone, 1-phenyl-propane-1,2-dione as well as mixtures thereof, and optionally an amine accelerator selected from the group consisting of p-(dimethylamino)-benzoic acid ethyl ester, dimethylaminoethyl methacrylate, N,N-dimethylaniline, N,N-dimethyl-p-toluidine, triethanolamine and mixtures thereof.

12. The process according to claim 10 , wherein the second photopolymerization initiator is selected from the group consisting of monoacyltrialkyl- and diacyldialkylgermanium compounds as well as mixtures thereof.

13. The process according to claim 1 , wherein the composition comprises an absorber selected from the group consisting of benzotriazoles, triazines, benzophenones, cyanoacrylates, salicylic acid derivatives, hindered amine light stabilizers (HALS), inorganic salts as well as mixtures thereof.

14. The process according to claim 1 , wherein the at least one polyreactive binder is selected from radically polymerizable monomers and prepolymers.

15. The process according to claim 1 , wherein the at least one polyreactive binder is selected from mono- and multifunctional (meth)acrylates and their mixtures.

16. The process according to claim 1 , wherein the composition further comprises filler.

17. The process according to claim 1 , wherein the composition comprises
(a) 5 to 90 wt.-% polyreactive binder,
(b) 0.01 to 5.0 wt.-% first photopolymerization initiator,
(c) 0.01 to 2.0 wt.-% second photopolymerization initiator,
(d) 0.001 to 3.0 wt.-% absorber and
(e) 5 to 90 wt.-% filler,
in each case relative to the total mass of the composition.

18. The process according to claim 1 , wherein the dental shaped part has the shape of an inlay, onlay, a crown or a bridge.

19. The process according to claim 1 , wherein
(i) the composite resin composition is cured in layers by the local introduction of radiation the emission maximum of which is at a wavelength of less than 400 nm to form a three-dimensional body, and
(ii) the obtained three-dimensional body is introduced into the mouth of a patient and further cured by the introduction of radiation the emission maximum of which is at a wavelength of at least 400 nm.

20. The process according to claim 19 , wherein in step (ii) initially a layer of a dental cement is applied to cement the dental component to the tooth, and this layer is also cured during the further curing in step (ii).

21. The process according to claim 19 , wherein the three-dimensional body has the shape of an inlay, onlay, a crown or a bridge.

22. The process according to claim 2 , wherein the longest-wavelength absorption maximum of the first photopolymerization initiator is at a wavelength in the range of from 300 to less than 400 nm.

23. The process according to claim 2 , wherein the longest-wavelength absorption maximum of the first photopolymerization initiator is at a wavelength in the range of from 330 to less than 400 nm.

24. The process according to claim 2 , wherein the longest-wavelength absorption maximum of the first photopolymerization initiator is at a wavelength in the range of 345 to less than 400 nm.

25. The process according to claim 4 , wherein the longest-wavelength absorption maximum of the second photopolymerization initiator is at a wavelength in the range of from 400 to 600 nm.

26. The process according to claim 5 , wherein the longest-wavelength absorption maximum of the second photopolymerization initiator is at a wavelength in the range of from 420 to 480 nm.

27. The process according to claim 6 , wherein the longest-wavelength absorption maximum of the absorber is at a wavelength in the range of from 300 to less than 400 nm.

28. The process according to claim 7 , wherein the longest-wavelength absorption maximum of the absorber is at a wavelength in the range of from 345 to less than 400 nm.

29. The process according to claim 7 , wherein the longest-wavelength absorption maximum of the absorber is at a wavelength in the range of from 360 to less than 400 nm.

30. The process according to claim 8 , wherein the difference between the absorption maxima of the first and second photopolymerization initiators is at least 10 nm.

31. The process according to claim 8 , wherein the difference between the absorption maxima of the first and second photopolymerization initiators is at least 15 nm.

32. The process according to claim 9 , wherein the first photopolymerization initiator is selected from the group consisting of acyl- and bisacylphosphine oxides, benzoin, benzoin alkyl ethers, benzil dialkyl ketals, α-hydroxyacetophenones, α-dialkoxyacetoph

Assignees

• Ivoclar Vivadent Ag
• Univ Wien Tech

Inventors

• Wachter Wolfgang
• Ebert Jörg
• Voser Dieter
• Moszner Norbert
• Rheinberger Volker
• Stampfl Jürgen

Classifications

• A61K6/62

  Photochemical radical initiators · CPC title

• B29C64/135

  the energy source being concentrated, e.g. scanning lasers or focused light sources · CPC title

• A61C13/0013 Primary

  using stereolithographic techniques · CPC title

• A61C5/77

  Methods or devices for making crowns · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title