Curable composition for producing a dental composite crown and process of production

Patent metadata

Field	Value
Publication number	US-12274765-B2
Application number	US-202318333956-A
Country	US
Kind code	B2
Filing date	Jun 13, 2023
Priority date	Jun 14, 2017
Publication date	Apr 15, 2025
Grant date	Apr 15, 2025

Abstract

The invention relates to A curable composition for producing dental composite crowns, the composition comprising a resin matrix comprising polymerizable (meth)acrylate(s) not comprising a urethane moiety, polymerizable urethane(meth)acrylate(s), wherein the polymerizable (meth)acrylate(s) not comprising an urethane moiety are used in excess over the polymerizable urethane(meth)acrylate(s), a filler matrix comprising nanocluster(s), fumed silica in an amount below 8 wt. % with respect to the weight of the whole composition, an initiator system comprising photoinitiator(s), organic dye(s), the curable composition not comprising softener in an amount of more than 5 wt. % with respect to the weight of the whole composition, the curable composition having a viscosity below 150 Pa*s at 23° C. and a shear rate of 1 s −1 .
The invention also relates to a cured article obtained by radiation curing this curable composition by use of an additive-manufacturing method.

First claim

What is claimed is:

1. A curable composition comprising:
a resin matrix comprising:
polymerizable (meth)acrylate(s) not comprising a urethane moiety present in an amount of 45 to 60 wt %, and
polymerizable urethane(meth)acrylate(s) present in an amount from 8 to 20 wt %;

a filler matrix present in an amount of 25 to 40 wt %, the filler matrix comprising:
nanocluster(s) present in an amount of 25 to 35 wt %;

an initiator system comprising:
photoinitiator(s),
wherein the curable composition is characterized by a viscosity below 150 Pa*s at 23° C. and a shear rate of 1 s −1 , and
wherein wt % is with respect to the weight of the curable composition.

2. The curable composition of claim 1 , the polymerizable (meth)acrylate(s) not comprising a urethane moiety and the polymerizable urethane(meth)acrylate(s) present in a weight ratio of 5:1 to 1.5:1.

3. The curable composition of claim 1 , the polymerizable (meth)acrylate(s) not comprising a urethane moiety comprising 1 or 2 polymerizable moieties.

4. The curable composition of claim 1 , the polymerizable (meth)acrylates not comprising a urethane moiety characterized by a molecular weight of 170 g/mol to 3,000 g/mol.

5. The curable composition of claim 1 , the polymerizable (meth)acrylate(s) not comprising a urethane moiety comprising bis[3 [4]-methacryl-oxymethyl-8 (9)-tricyclo[5.2.1.0 2,6 ]decylmethyl triglycolate, 2,2-bis-4 (3-methacryloxy-2-hydroxypropoxy)phenylpropane, 2,2-bis-4 (3-methacryloxypropoxy)phenylpropane, triethylene glycol dimethacrylate, glycerol dimethacrylate, an ethoxylated bisphenol A dimethacrylate, di(meth)acrylates of bishydroxymethyltricyclo-(5.2.1.0 2,6 )decane, or a combination thereof.

6. The curable composition of claim 1 , the polymerizable (meth)acrylate(s) not comprising a urethane moiety comprising an ethoxylated bisphenol A dimethacrylate.

7. The curable composition of claim 1 , wherein the polymerizable urethane(meth)acrylates(s) is derived from a polyisocyanate having an isocyanurate structure.

8. The curable composition of claim 1 , wherein the polymerizable urethane (meth)acrylates(s) is a reaction product of:
a polyisocyanate represented by a formula:

 and
a monofunctional (meth)acrylate represented by a formula:

9. The curable composition of claim 1 , wherein the polymerizable urethane(meth)acrylates(s) is represented by one or more of:

10. The curable composition of claim 1 , wherein the polymerizable urethane(meth)acrylates(s) is characterized by a molecular weight of 450 g/mol to 3,000 g/mol.

11. The curable composition of claim 1 , the nanocluster(s) being aggregated nanoparticles of silicon, zirconia, or a combination thereof.

12. The curable composition of claim 1 , excluding a fumed silica having a surface treated with a polymerizable moieties.

13. The curable composition of claim 1 , the filler matrix further comprising a fumed silica having a surface treated with a polymerizable silane, the fumed silica being present in an amount of no more than 5 wt %.

14. The curable composition of claim 1 , the filter matrix further comprising a fumed silica having a surface treated with —OSi(CH 3 ) 3 present in an amount of no more than 5 wt %.

15. The curable composition of claim 1 , further comprising organic dye(s).

16. The curable composition of claim 1 , excluding a softener.

17. The curable composition of claim 1 , further comprising a softener in an amount of no greater than 5 wt %.

18. The curable composition of claim 1 , further comprising an ethoxylated bisphenol A diacetate as softener in an amount of no greater than 8 wt %.

19. The curable composition of claim 1 ,
the polymerizable (meth)acrylate(s) not comprising a urethane moiety comprising an ethoxylated bisphenol A dimethacrylate, and
the polymerizable urethane(meth)acrylates(s) comprising a compound of a formula:

20. The curable composition of claim 1 , for use is producing a dental or orthodontic article.

Assignees

• Solventum Intellectual Properties Company

Inventors

• Herrmann Andreas
• Raia Gioacchino
• Korten Malte
• Kappler Oliver
• Hofmann Bernhard
• Eckert Adrian
• Mayr Helmar
• Hecht Reinhold
• Schechner Gallus
• Guggenberger Rainer

Classifications

• C08L75/06

  from polyesters · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• A61K6/17

  Particle size · CPC title

• A61K6/62 Primary

  Photochemical radical initiators · CPC title