Dental composition

Patent metadata

Field	Value
Publication number	US-2018092811-A1
Application number	US-201615562497-A
Country	US
Kind code	A1
Filing date	Mar 30, 2016
Priority date	Mar 30, 2015
Publication date	Apr 5, 2018
Grant date	—

Abstract

Disclosed herein is a dental composition having a polymerization initiator system with an aromatic tertiary phosphine compound. Further disclosed is the use of the aromatic tertiary phospine compound for the preparation of a photocurable dental compositions.

First claim

1 . A dental composition comprising
(a) one or more compounds having at least one polymerizable double bond; (b) a polymerization initiator system comprising
(b1) a sensitizer; and
(b2) an aromatic tertiary phosphine compound of the following formula (I):
Z—R   (I)

wherein
Z is a group of the following formula (II)
R 1 (Ar)P—   (II)

wherein
R 1 represents a substituted or unsubstituted hydrocarbyl group;
Ar represents a substituted or unsubstituted aryl or heteroaryl group;

R is an aryl group, which may be substituted by one or more groups selected from a hydroxyl group, an amino group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond;

wherein the group R 1 and Ar may be substituted by one or more groups selected from a hydroxyl group, an oxo group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from a hydrogen atom and C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond, and L may be substituted by one or more groups selected from a hydroxyl group, an oxo group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from a hydrogen atom and C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond.

2 . The dental composition according to claim 1 , wherein the polymerization initiator system further comprises
(b3) an electron-donor.

3 . The dental composition according to claim 1 , wherein R 1 and Ar independently are aromatic hydrocarbyl groups selected from a phenyl group, a naphtyl group, a tolyl group, a xylyl group, and a styryl group.

4 . The dental composition according to claim 1 , wherein the sensitizer is an 1,2-diketone, a 1,3 diketone or a phosphine oxide.

5 . The dental composition according to claim 2 , wherein the electron-donor is an amine compound.

6 . The dental composition according to claim 1 , wherein the polymerization initiator system comprises component (b1), (b2), and (b3) in a molar ratio ((b1):(b2):(b3)) of 1: (0.1 to 3.0):(0.0 to 3.0).

7 . The dental composition according to claim 1 , which further comprises a solvent and/or a particulate filler

8 . The dental composition according to claim 1 , wherein the dental composition is a dental restorative or dental prosthetic composition.

9 . The dental composition according to claim 8 , which is selected from a dental adhesive composition, a dental composite composition, a resin modified dental cement, a pit and fissure sealer, a desensitizer and a varnish.

10 . The dental composition according to claim 1 , wherein the aromatic phosphine compound is a compound of formula (I) wherein Z is a group of the following formula

11 . An aromatic phosphine compound of the following formula (I)
Z—R   (I)
wherein Z is a group of the following formula (II)
R 1 (Ar)P—   (II)

wherein
R 1 represents a substituted or unsubstituted hydrocarbyl group;
Ar represents a substituted or unsubstituted aryl group;
R is an aryl group, which may be substituted by one or more groups selected from a hydroxyl group, an amino group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond;
wherein the group R 1 and Ar may be substituted by one or more groups selected from a hydroxyl group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from a hydrogen atom and C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond, and L may be substituted by one or more groups selected from a hydroxyl group, an oxo group, a —NR 2 R 3 group (wherein R 2 and R 3 , which may be the same or different, are selected from a hydrogen atom and C 1-6 alkyl groups), a carboxyl group, and a group having a polymerizable double bond,
capable for use in the preparation of a dental composition.

12 . The aromatic phosphine compound according to claim 11 , wherein the phosphine is 4-(diphenylphosphino)styrene.

13 . The dental composition according to claim 2 , wherein the electron-donor (b3) is a compound of the following formula (IV):
A-H   (IV)
wherein A is a moiety of the following formula (II)
R a R b R c X—   (V)

wherein X represents Si, Ge, or Sn and R a represents a hydrogen atom, an organic moiety or a different moiety A; R b and R c
which are independent from each other, represent an organic moiety.

14 . The dental composition according to claim 13 , which comprises as sensitizer a combination of
(b1-a) a first sensitizer selected from an 1,2-diketone; and (b1-b) a second sensitizer selected from iodonium salts.

Assignees

• Dentsply Sirona Inc

Inventors

• Klee Joachim
• Maier Maximilian
• Lalevee Jacques
• Fik Christoph P
• Fouassier Jean Pierre
• Morlet-Savary Fabrice
• Dietlin Celine

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/30

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/838

  Phosphorus compounds, e.g. apatite · CPC title

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title