Photocurable dental composition

Patent metadata

Field	Value
Publication number	US-11844848-B2
Application number	US-201816754263-A
Country	US
Kind code	B2
Filing date	Oct 9, 2018
Priority date	Oct 13, 2017
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

The present invention relates to a photocurable dental composition comprising a specific polymerization initiator system containing the combination of a photoinitiator compound and a coinitiator compound being a sulfinate compound or a sulfonate compound. The present invention also relates to the use of this polymerization initiator system in a photocurable dental composition.

First claim

The invention claimed is:

1. Photocurable dental composition comprising
(a) one or more radical-polymerizable compounds,
(b) a polymerization initiator system containing
(i) an photoinitiator compound having a light absorption maximum in the range from 300 to 800 nm; and
(ii) a coinitiator compound;

wherein the coinitiator compound is a sulfinate compound or a sulfonate compound of the following formula (I):
(R—SO x − ) y M y+   (I)

wherein
R represents an organic moiety;
M y+ is a cation, an iodonium ion of the following formula (II):
R 1 —I + —R 2   (II)

wherein
R 1 and R 2 which are independent from each other represent an organic moiety, or combination thereof,
x is 2 or 3, and
y is an integer of from 1 to 4, and
(c) a dental particulate filler, wherein the dental particulate filler is selected from the group consisting of quartz, silicon nitride, feldspar, borosilicate glass, kaolin, talc, titania, zinc glass, pulverized polycarbonate, pulverized polyepoxide, and a glass derived from Ce, Sb, Sn, Zr, Sr, Ba, or Al.

2. The photocurable dental composition according to claim 1 , wherein R is an aromatic moiety.

3. The photocurable dental composition according to claim 1 , wherein R is a phenyl or naphthyl group which may be substituted by 1 to 5 substituents, which may be a same or different and which are independently selected from a group consisting of C 1-6 alkyl group, a hydroxyl group, an amino group, a halogen atom, and a carboxyl group.

4. The photocurable dental composition according to claim 1 , wherein R is an aliphatic moiety.

5. The photocurable dental composition according to claim 4 , wherein R is a C 1-6 alkyl group which may be substituted by a phenyl or naphthyl group which may be substituted by 1 to 5 substituents, which may be a same or different and which are independently selected from a C 1-6 alkyl group, a hydroxyl group, an amino group, a halogen atom, and a carboxyl group.

6. The photocurable dental composition according to claim 1 , wherein the dental composition comprises 0.05 to 5 mole percent of the coinitiator compound based on the one or more radical-polymerizable compounds.

7. The photocurable dental composition according to claim 1 , wherein the photoinitiator compound is a 1,2-diketone.

8. The photocurable dental composition according to claim 1 , wherein the dental composition comprises 0.05 to 5 mole percent of the photoinitiator compound based on the one or more radical-polymerizable compounds.

9. The photocurable dental composition according to claim 1 , wherein the coinitiator compound is contained in a solid part of a two or more part dental composition.

10. The photocurable dental composition according to claim 1 , wherein the photocurable dental composition is selected from the group consisting of a dental composite, a dental glass monomer cement, a dental cement, and a dental impression material.

11. The photocurable dental composition according to claim 1 , which wherein the polymerization initiator system further comprises an additional electron donor (iii) as a further coinitiator.

12. A method of forming a photocurable dental composition; said method comprising: mixing a polymerization initiator system containing
(i) a photoinitiator compound having a light absorption maximum in the range from 300 to 800 nm; and
(ii) a coinitiator compound;
wherein the coinitiator compound is a sulfinate compound or a sulfonate compound of the following formula (I):
(R—SO x − ) y M y+   (I)

wherein
R represents an organic moiety;
M y+ is a cation, an iodonium ion of the following formula (II):
R 1 —I + —R 2   (II)

wherein
R 1 and R 2 which are independent from each other represent an organic moiety, or combination thereof,
x is 2 or 3and,
y is an integer of from 1 to 4, and

with one or more radical-polymerizable compounds and a dental particulate filler to form the photocurable dental composition, wherein the dental particulate filler is selected from the group consisting of quartz, silicon nitride, feldspar, borosilicate glass, kaolin, talc, titania, zinc glass, pulverized polycarbonate, pulverized polyepoxide, and a glass derived from Ce, Sb, Sn, Zr, Sr, Ba, or Al.

13. The method according to claim 12 , wherein the photocurable dental composition is selected from the group consisting of a dental composite, a dental glass ionomer cement, a dental cement, and a dental impression material.

14. The photocurable dental composition according to claim 7 , wherein the 1,2-diketone is camphorquinone or tert-butyl (tert-butyldimethylsilyl)-glyoxylate) (DKSi).

15. The photocurable dental composition according to claim 1 , wherein the coinitiator compound is contained in a fluid part having a pH of from 6 to 8 of a one or more part dental composition.

16. Photocurable dental composition comprising (a) one or more radical-polymerizable compounds, (b) a polymerization initiator system containing (i) a photoinitiator compound having a light absorption maximum in the range from 300 to 800 nm; and
(ii) a sulfonate compound of formula:

17. The photocurable dental composition according to claim 1 , wherein the dental particulate filler has a maximum particle diameter less than about 100 μm and an average particle diameter less than about 10 μm.

18. The method according to claim 12 , wherein the dental particulate filler has a maximum particle diameter less than about 100 μm and an average particle diameter less than about 10 μm.

19. The photocurable dental composition according to claim 1 , wherein x is 3 and R is an aromatic moiety.

20. The photocurable dental composition according to claim 1 , wherein the dental particulate filler is borosilicate glass.

21. The photocurable dental composition according to claim 1 , wherein the dental particulate filler is a glass derived from Ba.

22. The photocurable dental composition according to claim 1 , wherein the dental particulate filler is a glass derived from Sb.

23. The photocurable dental composition according to claim 16 further comprising a dental particulate filler, wherein the dental particulate filler is selected from the group consisting of quartz, silicon nitride, feldspar, borosilicate glass, kaolin, talc, titania, zinc glass, pulverized polycarbonate, pulverized polyepoxide, and a glass derived from Ce, Sb, Sn, Zr, Sr, Ba, or Al.

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Szillat Florian
• Maier Maximilian
• Renn Caroline
• Elsner Oliver
• Klee Joachim E
• Kempter Jorg
• Lalevee Jacques
• Bouzrati-Zerelli Mariem
• Kirschner Julie

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/889

  Polycarboxylate cements; Glass ionomer cements · CPC title

• A61K6/90

  Compositions for taking dental impressions · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title