Dental composition

Patent metadata

Field	Value
Publication number	US-2017156992-A1
Application number	US-201515323161-A
Country	US
Kind code	A1
Filing date	Jul 2, 2015
Priority date	Jul 2, 2014
Publication date	Jun 8, 2017
Grant date	—

Abstract

Dental composition comprising
(a) at least two di- or polyepoxides having 2 to 5 epoxide groups and having a molecular weight of from 200 to 700 Da, or a macromonomeric reaction product obtainable by reacting the diepoxide with a dicarboxylic acid in a molar ratio [diepoxide]/[dicarboxylic acid] of at least 2;

(b) one or more primary monoamines and/or disecondary diamines;

(c) optionally one or more aliphatic polyamines;

(d) a particulate filler,

wherein the molar ratio of epoxide groups in component (a) to the N—H bonds in component (b) and (c) [epoxide (a) ]/[N—H (b),(c) ] is in the range of from 0.9 to 1.1;

wherein the di- or polyepoxide having 2 to 5 epoxide groups is a compound of the following formula (I):

A(BZ m ) n   (I)

wherein

A represents an n-valent organic moiety optionally having 1 to 10 heteroatoms selected from oxygen atoms and sulfur atoms; and

B represents an m+1-valent organic moiety,

Z is an epoxide group which may have a substituent,

m which are independent from each other represent an integer of at least 1; and

n is an integer of from 1 to 5;

wherein the m are selected so that 2 to 5 epoxide groups are present;

wherein the composition does not contain any 2,2-bis-(4-hydroxyphenyl)-propane, or 2,2-bis-(4-hydroxyphenyl)-methane.

First claim

1 . Dental composition comprising
(a) at least two di- or polyepoxides having 2 to 5 epoxide groups and having a molecular weight of from 200 to 700 Da, or a macromonomeric reaction product obtainable by reacting the diepoxide with a dicarboxylic acid in a molar ratio [diepoxide]/[dicarboxylic acid] of at least 2; (b) one or more primary monoamines and/or disecondary diamines; (c) optionally one or more aliphatic polyamines; (d) a particulate filler, wherein the molar ratio of epoxide groups in component (a) to the N—H bonds in component (b) and (c) [epoxide (a) ]/[N—H (b),(c) ] is in the range of from 0.9 to 1.1; wherein the di- or polyepoxide having 2 to 5 epoxide groups is a compound of the following formula (I):
A(BZ m ) n   (I)

wherein A represents an n-valent organic moiety optionally having 1 to 10 heteroatoms selected from oxygen atoms and sulfur atoms; and B represents an m+1-valent organic moiety, Z is an epoxide group which may have a substituent, m which are independent from each other represent an integer of at least 1; and n is an integer of from 1 to 5; wherein the m are selected so that 2 to 5 epoxide groups are present; wherein the composition does not contain any 2,2-bis-(4-hydroxyphenyl)-propane or 2,2-bis-(4-hydroxyphenyl)-methane.

2 . The dental composition according to claim 1 , wherein component (c) is present in an amount of from 5 to 95 percent by weight based on the total amount of (b) and (c) in the composition.

3 . The dental composition according to claim 1 or 2 , wherein component (c) is an aliphatic polyamine selected among compounds of the following structures:

wherein
R 10 denotes hydrogen or a substituted or unsubstituted C 1 to C 18 alkyl group, a substituted or unsubstituted C 3 to C 18 cycloalkyl group, or a substituted or unsubstituted C 7 to C 18 aralkyl group,
R 20 represents a difunctional substituted or unsubstituted C 1 to C 18 alkylene group, or a substituted or unsubstituted cycloalkylene group,
A′ denotes a moiety derived from a compound that is capable of an addition reaction with amines such as di- or polyepoxides,
c is an integer.

4 . The dental composition according to any one of the preceding claims, wherein the heteroatoms selected from oxygen atoms and sulfur atoms in groups A are present in ester bonds, ether bonds, thioether bonds or thioester bonds.

5 . The dental composition according to any one of the preceding claims, wherein A contains an aromatic ring.

6 . The dental composition according to any one of the preceding claims, wherein the at least two di- or polyepoxides having 2 to 5 epoxide groups are obtainable by reacting a compound having 2 to 5 hydroxyl groups with epichlorohydrine.

7 . The dental composition according to claim 6 , wherein the compound having 3 to 5 hydroxyl groups contains phenolic hydroxyl groups.

8 . The dental composition according to claim 1 , wherein BZ is a group of the formula (II) or (III):

wherein
X is —NH—, an oxygen atom or a sulfur atom,
X′ is —NH—, an oxygen atom or a sulfur atom,
X″ is —NH—, an oxygen atom or a sulfur atom,
X′″ is —CH 2 —, —NH—, an oxygen atom or a sulfur atom,
R 11 and R 12
which may be the same or different, independently represent a hydrogen atom or a straight chain or branched C 1-6 alkyl group,

R 13 represents a hydrogen atom or a straight chain or branched C 1-6 alkyl group,
R 14
represents a hydrogen atom, a hydroxyl group which may be substituted, or a straight chain or branched C 1-6 alkyl group,

o represents an integer of from 2 to 10,
p is an integer of from 0, 1 or 2;
q which may be the same or different, independently represent an integer of from 0 to 10;
v represents an integer of from 1 to 10.

9 . The dental composition according to any one of the preceding claims, which is a root canal filling composition or a pulp capping composition.

10 . The dental composition according to any one of the preceding claims, which has a gel time of at most 12 hours.

11 . A process for preparing a composition according to any one of claims 1 to 10 , which comprises reacting one or more compounds having 2 to 5 hydroxyl groups with epichlorohydrine for preparing a di- or polyepoxide having 2 to 5 epoxide groups as defined by claim 1 .

12 . The process according to claim 11 , which further comprises a step reacting the diepoxide with a dicarboxylic acid in a molar ratio [diepoxide]/[dicarboxylic acid] of at least 2 for obtaining a macromonomeric reaction product.

13 . Di- or polyepoxide having 2 to 5 epoxide groups obtainable by the process according to any one of claim 11 or 12 .

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Klee Joachim

Classifications

• C08G59/502

  Polyalkylene polyamines · CPC title

• C08G59/226

  Mixtures of di-epoxy compounds · CPC title

• A61K6/60

  comprising organic or organo-metallic additives · CPC title

• A61K6/54

  Filling; Sealing · CPC title

• C07D301/16 Primary

  formed in situ, e.g. from carboxylic acids and hydrogen peroxide · CPC title