Dental composition

Patent metadata

Field	Value
Publication number	US-12396929-B2
Application number	US-202017601786-A
Country	US
Kind code	B2
Filing date	Apr 9, 2020
Priority date	Apr 15, 2019
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

Disclosed herein is a dental material containing a polymerizable hydrolysis stable polycyclic amide monomer. The present disclosure relates to methods of making and use of the polymerizable hydrolysis stable polycyclic amide monomer for the preparation of a dental polymerizable hydrolysis stable polycyclic amide monomer composition. The present disclosure further relates to a cured dental material obtained by polymerizing the dental material.

First claim

The invention claimed is:

1. A dental material comprising:
(i) a polymerizable hydrolysis stable polycyclic amide monomer comprising a compound of Formula (I)

wherein
R 1 , R 2 , R 3 and R 4 are independent from each other, and represent a hydrogen, a C 1-4 alkyl group or a C 5 -C 18 aryl group;
R 5 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 7 -C 12 aralkyl group;
wherein each group of R 5 is optionally substituted by one or more of a C 1-4 alkyl group, a C 1-4 alkoxy group, or a hydroxyl group;
R 6 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 1 -C 12 aralkyl group, a C 6 -C 10 aryl group, an ester or an amide group,
X is an alkylene group, O, S, or CO;
n is an integer of from 0 to 1;
m is an integer of from 1 to 6; and
Z is an m valent unsubstituted or substituted C 1 -C 18 alkylene group, an unsubstituted or substituted C 3 -C 8 cycloalkylene group, an unsubstituted or substituted aralkylene group, an unsubstituted or substituted C 5 -C 18 arylene group or an unsubstituted or substituted C 3 -C 18 heteroarylene group; wherein each unsubstituted or substituted group of Z optionally includes at least one of 1-6 oxygen, silicon, sulfur atoms, or NR 9 , wherein R 9 represents a hydrogen atom, straight or branched or cyclic C 1-6 alkyl groups;
(ii) at least one polymerizable resin monomer having at least one (meth) acrylate group, (meth) acrylamide group, allyl group or vinyl group;
(iii) optionally a particulate filler; and
(iv) at least one of a photoinitiator and a redox initiator.

2. The dental material according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 and R 6 is a hydrogen; X is alkylene and n is 1.

3. The dental material according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is a hydrogen; X is alkylene, m is 1 and n is 1.

4. The dental material according to claim 1 , wherein Z represent a group of Formula IV, V, or VI

wherein
R a , R b , R c , R d , R e and R f are independently a same or different hydrogen atom, a C 1-6 linear or branched alkyl group, or a C 4-10 aryl group;
R 8 represent a straight chain, branched or cyclic alkyl group;
X 3 and X 4 are independently a same or different oxygen atom, a sulfur atom or a group NR 9 , wherein R 9 is a hydrogen atom or a C 1-4 alkyl group;
L 3 is a divalent hydrocarbon radical selected from linear or branched C 2-3 alkylene group or C 5 -C 18 arylene group;
L 4 and L 5 are independently a same or different C 2-20 alkylene group;
a is an integer of from 1 to 18;
b is an integer of from 1 to 10;
c is an integer of from 1 to 10;
d is an integer of from 0 to 1,
e is an integer of from 1 to 10; and
f is an integer of from 0 to 1.

5. The dental material according to claim 1 , wherein the compound of formula (I) is obtained by reacting a mixture comprising:
(i) x equivalent of at least one component A having compound of Formula (II)

wherein
R 1 , R 2 , R 3 and R 4 are independent from each other, and represent a hydrogen, a C 1-4 alkyl group or a C 5 -C 18 aryl group;
R 6 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 7 -C 12 aralkyl group, a C 6 -C 10 aryl group, an ester or an amide group,
X is an alkylene group, O, S, or CO;
n is an integer of from 0 to 1; and
T is a hydroxyl group or a halogen atom,
(ii) y equivalent of a component B having at least one of primary amine functional group and secondary amine functional group of compounds of Formula III:

wherein
R 7 is a (r+1)-valent aliphatic C 2-10 group, cycloaliphatic C 3 -C 6 group or an aralkylene group having 7 to 24 carbon atoms, wherein each group of Ry optionally contains oxygen or sulfur atoms and each group of R 7 is optionally substituted by C 1-4 alkyl groups;
R 5 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 7 -C 12 aralkyl group, or an (meth) acryl group; wherein each group of R 5 is optionally substituted by one or more of a C 1-4 alkyl group, a C 1-4 alkoxy group, or a hydroxyl group;
L 1 and L 2 are independently a same or different straight or branched chain alkylene having from 1 to 4 carbons;
X 1 is a direct bond, or a nitrogen atom substituted by R 5 ;
X 2 is an oxygen atom;
p and q are an integer of from 0 to 4; and
r is an integer of from 1 to 6,
wherein x and y are molar equivalents of a component (i) and (ii).

6. The dental material according to claim 1 , wherein the at least one polymerizable resin monomer is selected from the group consisting of 2,2′-bis [4-(3-methacryloxy-2-hydroxypropoxy)-phenyl] propane (bis-GMA), tetraethyleneglycoldi (meth) acrylate (TEGDMA), urethane dimethacrylate (UDMA), trimethylolpropane trimethacrylate, C 1 -C 20 alkyl (meth) acrylates, an aromatic methacrylate, and a hydroxy alkyl (meth)acrylate.

7. The dental material according to claim 1 , wherein the polymerizable hydrolysis stable polycyclic amide monomer is present in an amount of from 1 to 99% w/w based on total weight of the dental material.

8. The dental material according to claim 1 , wherein the at least one of photoinitiator and redox initiator is present in an amount of from 0.01 to 5% w/w based on total weight of the dental material.

9. The dental material according to claim 1 , wherein the at least one polymerizable resin monomer is present in an amount of from 1 to 99% w/w based on total weight of the dental material.

10. The dental material according to claim 1 , wherein the dental material is a dental composite or a dental cement and includes a particulate filler.

11. The dental material according to claim 10 , wherein the particulate filler is present in an amount of from 10 to 90% w/w based on total weight the dental composite material.

12. The dental material according to claim 1 , further comprising a stabilizer, one or more polymerization inhibitor(s), one or more solvents, and combinations thereof.

13. A cured dental material obtained by polymerizing a mixture comprising:
(i) a polymerizable hydrolysis stable polycyclic amide monomer comprising compound of Formula (I)

wherein
R 1 , R 2 , R 3 and R 4 are independent from each other, and represent a hydrogen, a C 1-4 alkyl group or a C 5 -C 18 aryl group;
R 5 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 7 -C 12 aralkyl group;
wherein each group of R 5 is optionally substituted by one or more of a C 1-4 alkyl group, a C 1-4 alkoxy group, or a hydroxyl group;
R 6 is a hydrogen atom, a C 1-6 alkyl group, a C 3-10 cycloalkyl group, a C 7 -C 12 aralkyl group, a C 6 -C 10 aryl group, an ester or an amide group,
X is an alkylene group, O, S, or CO;
n is an integer of from 0 to 1;
m is an integer of from 1 to 5; and

Assignees

• Dentsply Sirona Inc

Inventors

• Ritter Helmut
• Klee Joachim E
• Lu Hui
• Neuhaus Kira

Classifications

• C08F32/06

  having two or more carbon-to-carbon double bonds · CPC title

• C08F32/02

  having no condensed rings · CPC title

• C08F32/04

  having one carbon-to-carbon double bond · CPC title

• C08L45/00

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• C08F32/08

  having two condensed rings (coumarone-indene polymers C08F244/00) · CPC title