Dental composition

Patent metadata

Field	Value
Publication number	US-11116702-B2
Application number	US-201716469186-A
Country	US
Kind code	B2
Filing date	Dec 12, 2017
Priority date	Dec 14, 2016
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

Abstract

The present invention relates to a dental composition comprising a specific polymerizable compound and a polymerization initiator system. Furthermore, the present invention relates to the specific polymerizable compound as such and its use in a dental composition. The specific polymerizable compound of the present invention has an N-allyl (meth)acrylamide group, which nitrogen atom is substituted with an alkyl or alkenyl group optionally substituted by a group selected from a hydroxyl group, a C 1-4 alkoxy group, a tertiary amino group and a carboxyl group, wherein 1 to 8 carbon atoms in the main chain of the alkyl or alkenyl group may independently from each other be replaced by a heteroatom selected from an oxygen atom and a sulfur atom.

First claim

The invention claimed is:

1. A dental composition comprising
(a) a polymerizable compound of the following formula (I):

wherein
R represents a straight chain or branched C 2-18 alkyl or alkenyl group, which may be substituted by a group selected from a hydroxyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and wherein 1 to 8 carbon atoms in the main chain of the C 2-18 alkyl or alkenyl group may independently from each other be replaced by a heteroatom selected from an oxygen atom and a sulfur atom, and
R* represents a hydrogen atom or a methyl group; and

(b) a polymerization initiator system.

2. The dental composition according to claim 1 , wherein R is a group of the following formula (II)

wherein
X is a hydrogen atom, a hydroxyl group, a C 1-4 alkoxy group, a tertiary amino group or a carboxylic acid group;
Z is an oxygen atom or a sulfur atom, and in case more than one Z is present, the Z may be the same or different;
R 1 is a hydrogen atom or a group selected from a hydroxyl group, a C 1-4 alkyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and in case more than one group R 1 is present, the groups may be the same or different;
R 2 is a hydrogen atom or a group selected from a hydroxyl group, a C 1-4 alkyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and in case more than one group R 2 is present, the groups may be the same or different;
a is 0 or 1;
b is an integer of from 2 to 18;
c is an integer of from 2 to 16;
d is an integer of from 0 to 8; and
e is an integer of from 1 to 3.

3. The dental composition according to claim 1 , wherein the polymerizable compound is a compound of the following formula (Ia) or (Ib):

wherein
R* represents a hydrogen atom or a methyl group,
X is a hydroxyl group, a tertiary amino group or a carboxylic acid group;
n is an integer of from 5 to 18, and
m is an integer of from 2 to 15.

4. The dental composition according to claim 3 , wherein n in the compound of the following formula (III) is 6 to 12, or wherein m in the compound of the formula (IV) is 2 to 8.

5. The dental composition according to claim 1 , wherein the polymerizable compound of the following formula (I) has a dynamic viscosity at 23° C. of at most 10 Pa·s.

6. The dental composition according to claim 2 , wherein X is a hydroxyl group or a carboxylic acid group.

7. The dental composition according to claim 1 , wherein the compound of formula (I) is contained in an amount of from 1 to 80 percent by weight based on the total weight of the composition.

8. The dental composition according to claim 1 , wherein the polymerization initiator is a photoinitiator, a redox initiator, or a mixture thereof.

9. The dental composition according to claim 1 , wherein the polymerization initiator is contained in an amount of from 0.01 to 10 percent based on the total weight of the composition.

10. The dental composition according to claim 1 , which is selected from a highly filled dental composite, a flowable dental composite, pit and fissure sealant, a dental adhesive, a dental cement, root canal sealer, a glass ionomer cement, and a dental infiltrant.

11. A polymerizable compound of the following formula (I′):

wherein
R′ represents a straight chain or branched C 5-18 alkyl or alkenyl group, which may be substituted by a group selected from a hydroxyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and wherein 1 to 8 carbon atoms in the main chain of the C 5-18 alkyl or alkenyl group may independently from each other be replaced by a heteroatom selected from an oxygen atom and a sulfur atom, and
R*′ represents a hydrogen atom or a methyl group,

provided that the compound is not N-allyl-N-tridecylacrylamide, N-allyl-N-(2,5,8,11-tetraoxatridecan-13-yl)acrylamide or N-octyl-N-allylacrylamide.

12. The compound according to claim 11 , wherein R′ is a group of the following formula (II′)

wherein
X is a hydrogen atom, a hydroxyl group, a C 1-4 alkoxy group, a tertiary amino group or a carboxylic acid group;
Z is an oxygen atom or a sulfur atom, and in case more than one Z′ is present, the Z′ may be the same or different;
R 1 is a hydrogen atom or a group selected from a hydroxyl group, a C 1-4 alkyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and in case more than one group R 1 ′ is present, the groups may be the same or different;
R 2 is a hydrogen atom or a group selected from a hydroxyl group, a C 1-4 alkyl group, a C 1-4 alkoxy group, a tertiary amino group, and a carboxylic acid group, and in case more than one group R 2 ′ is present, the groups may be the same or different;
a is 0 or 1;
b is an integer of from 2 to 18;
c is an integer of from 2 to 16;
d is an integer of from 0 to 8; and
e is an integer of from 1 to 3,
provided that when a=d=0, then b is at least 5.

13. The compound according to claim 12 , which is a compound of the following formula (III′) or (IV′):

wherein
R*′ represents a hydrogen atom or a methyl group, preferably a hydrogen atom,
X′ is a hydrogen atom, a hydroxyl group, a tertiary amino group or a carboxylic acid group;
n′ is an integer of from 5 to 18, and
m′ is an integer of from 2 to 15.

14. The compound according to claim 13 , which is selected from the following compounds:

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Fik Christoph
• Klee Joachim E
• Scheufler Christian
• Weber Christoph

Classifications

• A61K6/30

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

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title

• A61C5/50

  Implements for filling root canals; Methods or instruments for medication of tooth nerve channels · CPC title

• A61K6/72

  comprising nitrogen-containing compounds · CPC title

• C08F220/44 Primary

  Acrylonitrile · CPC title