Dental composition

Patent metadata

Field	Value
Publication number	US-12097271-B2
Application number	US-202017601862-A
Country	US
Kind code	B2
Filing date	Apr 9, 2020
Priority date	Apr 11, 2019
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

Dental root canal filling composition comprising
(a) one or more diepoxides; (b) one or more primary monoamines and/or disecondary diamines; (c) a particulate filler,

wherein the one or more diepoxides are selected from compounds of the following formula (I) or a salt thereof:

First claim

The invention claimed is:

1. Dental root canal filling composition comprising
(a) one or more diepoxides;
(b) one or more primary monoamines and/or disecondary diamines;
(c) a particulate filler,

wherein the one or more diepoxides are selected from compounds of the following formula (I) or a salt thereof:

wherein
R which may be the same or different when more than one R is present, represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group, a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two R may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms;
L 1 and L 2
which may be the same or different when more than one of L 1 and L 2 is present, independently represent a divalent saturated C 2-10 hydrocarbyl group or a polysiloxane group;

a is an integer of at least 1;
b is an integer of at least 2;
m is an integer of from 1 to 3; and
n is an integer of from 1 to 1000.

2. The dental root canal filling composition according to claim 1 , wherein the compound of formula (I) or a salt thereof is obtained by reacting one or more compounds of the following formula (II):

wherein R which may be the same or different when more than one R is present, represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group, a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two R may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms, and m is an integer of from 1 to 3, with an excess of one or more compounds of the following formula (III)

wherein each L 1 independently represents a divalent saturated C 2-10 hydrocarbyl group or a polysiloxane group and a is an integer of at least 1.

3. The dental root canal filling composition according to claim 1 , wherein the diepoxide is a compound of the following formula (IA) or a salt thereof:

wherein
R which may be the same or different when more than one R is present, represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two R may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms;
R 1 and R 2
which may be the same or different when more than one of R 1 and R 2 is present, represent a hydrogen atom or a C 1-6 alkyl group;

a is an integer of at least 1;
b is an integer of at least 2;
m is an integer of from 1 to 3; and
n is an integer of from 1 to 1000.

4. The dental root canal filling composition according to claim 1 , wherein m is 3.

5. The dental root canal filling composition according to claim 1 , wherein R is a C 1-6 alkoxy group or a C 1-6 alkyl group.

6. The dental root canal filling composition according to claim 1 , wherein the one or more diepoxides are selected from compounds of the following formula (IB) or a salt thereof:

wherein R a , R b , and R c independently represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two of R a , R b , and R c may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms;

R 1 and R 2 which may be the same or different when more than one of R 1 and R 2 is present, represent a hydrogen atom or a C 1-6 alkyl group;
a is an integer of at least 1;
b is an integer of at least 2;
and n is an integer of from 1 to 1000.

7. The dental root canal filling composition according to claim 1 , wherein the one or more diepoxides of component (a) have a dynamic viscosity at 23° C. of less than 10 Pa·s.

8. The dental root canal filling composition according to claim 1 , which has a gelation time of less than 20 hours.

9. The dental root canal filling composition according to claim 1 , which further comprises an aliphatic polyamine selected among compounds of the following structures:

wherein
R 5 represents 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 6 represents a difunctional substituted or unsubstituted C 1 to C 18 alkylene group, or a substituted or unsubstituted cycloalkylene group,
A′ represents a moiety derived from a compound that is capable of an addition reaction with an amine, and
c is an integer.

10. The dental root canal filling composition according to claim 1 , wherein the particulate filler (c) comprises CaWO 4 .

11. A diepoxide of the following formula (I) or a salt thereof:

wherein
R which may be the same or different when more than one R is present, represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two R may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms;
R 1 and R 2
which may be the same or different when more than one of R 1 and R 2 is present, represent a hydrogen atom or a C 1-6 alkyl group;

a is an integer of at least 1;
b is an integer of at least 2;
m is an integer of from 1 to 3; and
n is an integer of from 1 to 1000.

12. The diepoxide according to claim 11 , for use in the treatment of endodontic disease.

13. A process for preparing a diepoxide of the following formula (I) or a salt thereof:

wherein
R which may be the same or different when more than one R is present, represents a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 alkyl group a di-C 1-6 -alkylamino group, or a C 6-10 aryl group, or two R may be linked together and form with the carbon atoms to which they are bonded a 5- to 7-membered ring which may contain 1 or 2 heteroatoms selected from oxygen atoms and sulfur atoms;
R 1 and R 2
which may be the same or different when more than one of R 1 and R 2 is present, represent a hydrogen atom or a C 1-6 alkyl group;
a is an integer of at least 1;
b is an integer of at least 2;
m is an integer of from 1 to 3; and
n is an integer of from 1 to 1000, which comprises reacting one or more compounds of t

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Klee Joachim E
• Worm Matthias

Classifications

• C08L63/00

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

• A61K6/60

  comprising organic or organo-metallic additives · CPC title

• A61K6/891

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

• C07D303/28

  Ethers with hydroxy compounds containing oxirane rings · CPC title

• C08G59/066

  with chain extension or advancing agents · CPC title