Dental polymerizable monomer compositions

Patent metadata

Field	Value
Publication number	US-10130563-B2
Application number	US-201515300669-A
Country	US
Kind code	B2
Filing date	Mar 31, 2015
Priority date	Mar 31, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

Provided are dental polymerizable monomer compositions that can give cured products having high toughness and high rigidity, and dental compositions containing such dental polymerizable monomer compositions and cured products thereof having high mechanical properties. The dental polymerizable monomer composition includes a urethane acrylate compound (A) and a polymerizable compound (B) having at least one polymerizable group selected from methacryloyl groups and acryloyl groups, the urethane acrylate compound (A) being obtained by reacting a specific hydroxyacrylate (a1) with a diisocyanate (a2) having two isocyanate groups bonded to a divalent C6-9 aromatic hydrocarbon group or a divalent C6-9 bridged cyclic hydrocarbon group via a methylene group optionally substituted with a hydrocarbon group in place of a hydrogen atom, the proportion of the number of acryloyl groups present in the urethane acrylate compound (A) being 10% to less than 90% relative to the total number of (meth)acryloyl groups in the monomer composition.

First claim

The invention claimed is:

1. A dental polymerizable monomer composition comprising a urethane acrylate compound (A) and a polymerizable compound (B) having at least one polymerizable group selected from methacryloyl groups and acryloyl groups, the dental polymerizable monomer composition satisfying (I) and (II) below:
(I) the urethane acrylate compound (A) is obtained by reacting a hydroxyacrylate (a1) represented by the general formula (1) below with a diisocyanate (a2) having two isocyanate groups bonded to a divalent C 6-9 aromatic hydrocarbon group or a divalent C 6-9 bridged cyclic hydrocarbon group via a methylene group optionally substituted with a hydrocarbon group;
(II) the proportion of the number of acryloyl groups present in the urethane acrylate compound (A) is 10% to less than 90% relative to the total number of methacryloyl groups and acryloyl groups in the polymerizable monomer composition;

(in the general formula (1), R a represents a C 2-6 linear alkylene group or a C 2-6 linear oxyalkylene group, each of which is optionally substituted with a C 1-3 alkyl group or a (meth)acryloyloxymethylene group in place of a hydrogen atom).

2. The dental polymerizable monomer composition according to claim 1 , wherein the proportion of the number of acryloyl groups present in the urethane acrylate compound (A) is 40% to less than 90% relative to the total number of methacryloyl groups and acryloyl groups in the polymerizable monomer composition.

3. The dental polymerizable monomer composition according to claim 1 , wherein the ratio of the acryloyl groups to the methacryloyl groups present in the dental polymerizable monomer composition is in the range of 10:90 to 90:10.

4. The dental polymerizable monomer composition according to claim 1 , wherein the ratio of the acryloyl groups to the methacryloyl groups present in the dental polymerizable monomer composition is in the range of 40:60 to 90:10.

5. The dental polymerizable monomer composition according to claim 1 , wherein the diisocyanate (a2) is at least one selected from compounds represented by the general formula (2) below:

(in the general formula (2), R b represents a divalent C 6-9 aromatic hydrocarbon group or a divalent C 6-9 bridged cyclic hydrocarbon group; and R c , R d , R e and R f are each hydrogen or a methyl group).

6. The dental polymerizable monomer composition according to claim 5 , wherein the diisocyanate (a2) is at least one selected from compounds represented by the general formulas (3) to (5) below:

7. The dental polymerizable monomer composition according to claim 6 , wherein the urethane acrylate (A) is at least one compound represented by the general formula (6) below:

(in the general formula (6), R i is a group represented by the formula (7), (8) or (9) below; R g and R h are each independently a C 2-6 linear alkylene group or a C 2-6 linear oxyalkylene group, each of which is optionally substituted with a C 1-3 alkyl group or a (meth)acryloyloxymethylene group in place of a hydrogen atom; and R j represents a hydrogen atom or a methyl group);

8. The dental polymerizable monomer composition according to claim 1 , wherein R a in the general formula (1) independently at each occurrence represents a C 2-6 linear alkylene group or a C 2-6 linear oxyalkylene group, each of which is optionally substituted with a C 1-3 alkyl group in place of a hydrogen atom.

9. The dental polymerizable monomer composition according to claim 7 , wherein R g and R h in the general formula (6) are each independently a C 2-6 linear alkylene group or a C 2-6 linear oxyalkylene group, each of which is optionally substituted with a C 1-3 alkyl group in place of a hydrogen atom, and R j is a hydrogen atom.

10. The dental polymerizable monomer composition according to claim 1 , wherein the viscosity at 25° C. is 1 to 100,000 mPa·s.

11. A dental composition comprising the dental polymerizable monomer composition described in claim 1 , a polymerization initiator and a filler.

12. A dental material obtained by curing the dental composition described in claim 11 .

Assignees

• Mitsui Chemicals Inc
• Shofu Inc
• Sun Medical Co Ltd

Inventors

• Yoshinaga Kazuhiko
• Naruse Hiroshi
• Teramae Mitsuji
• Fuchigami Kiyomi
• Fujimura Hidefumi
• Tsuchikawa Masuji
• Imai Hirofumi

Classifications

• A61K6/71

  Fillers · CPC title

• A61K6/887 Primary

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

• A61K6/30

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

• A61K6/79 Primary

  Initiators · CPC title

• A61K6/889

  Polycarboxylate cements; Glass ionomer cements · CPC title