Dental composition

Patent metadata

Field	Value
Publication number	US-10596078-B2
Application number	US-201916357862-A
Country	US
Kind code	B2
Filing date	Mar 19, 2019
Priority date	Jul 2, 2014
Publication date	Mar 24, 2020
Grant date	Mar 24, 2020

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

The invention claimed is:

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 obtained 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) 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 heteroatoms selected from oxygen atoms and sulfur atoms in groups A are present in ester bonds, ether bonds, thioether bonds or thioester bonds; and
wherein the composition does not contain any of 2,2-bis-(4-hydroxyphenyl)-propane, 2,2-bis-(4-hydroxyphenyl)-methane, bisphenol-A diglycidyl ether, bisphenol-F diglycidyl ether, or butanediol diglycidyl ether.

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 , wherein component (c) is present and 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 di- or polyepoxides that is capable of an addition reaction with an amine, and
c is an integer.

4. 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.

5. The dental composition according to claim 1 , wherein A contains following moiety:

6. The dental composition according to claim 1 , wherein one or more primary monoamines are selected from compounds of the following formula (IV):
R—NH 2   (IV)

wherein R is a monovalent aliphatic moiety which may be substituted by an aromatic group.

7. The dental composition according to claim 1 , wherein one or more disecondary diamines are selected from compound of the following formula (V):
R′NHR″NHR′″  (V)

R′ and R′″ represent a monovalent aliphatic moiety which may be substituted by an aromatic group, and R″ is a divalent aliphatic moiety.

8. The dental composition according to claim 1 , which is a root canal filling composition or a pulp capping composition.

9. The dental composition according to claim 1 , wherein the composition is obtained by a process comprising a step of a step-growth polyaddition reaction of mixture containing at least two polymerizable di- or polyepoxides having 2 to 5 epoxide groups, or a macromonomeric reaction product obtained by reacting the diepoxide with a dicarboxylic acid in a molar ratio [diepoxide]/[dicarboxylic acid] of at least 2 with one or more primary monoamines and/or disecondary diamines and one or more aliphatic polyamines;
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 molar ratio of epoxide groups in Formula 1 to the N—H bonds in primary monoamines and/or disecondary diamines and aliphatic amines [epoxide/NH] is in the range of from 0.9 to 1.1;

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; and
wherein the dental composition does not contain any of 2,2-bis-(4-hydroxyphenyl)-propane, 2,2-bis-(4-hydroxyphenyl)-methane, bisphenol-A diglycidyl ether, bisphenol-F diglycidyl ether or butanediol diglycidyl ether.

Assignees

• Dentsply Sirona Inc

Inventors

• Klee Joachim

Classifications

• C08G59/502

  Polyalkylene polyamines · CPC title

• C08G59/50

  Amines · CPC title

• C07D301/16 Primary

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

• A61K6/54

  Filling; Sealing · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title