Non-solvent dental adhesive composition

Patent metadata

Field	Value
Publication number	US-11452674-B2
Application number	US-201816642708-A
Country	US
Kind code	B2
Filing date	Aug 28, 2018
Priority date	Aug 28, 2017
Publication date	Sep 27, 2022
Grant date	Sep 27, 2022

Abstract

The present invention provides a non-solvent dental adhesive composition exhibiting high initial bond strength and high bond durability to a tooth structure (wet matter) and a high dentin cohesive failure rate on a tooth structure (wet matter) and being substantially free of water and an organic solvent. The present invention relates to a non-solvent dental adhesive composition comprising: an acid group-containing polymerizable monomer (A); a hydrophobic polymerizable monomer (B) having no acid group; and a water-soluble photopolymerization initiator (C) having a solubility of 10 g/L or more in water at 25° C.

First claim

The invention claimed is:

1. A non-solvent dental adhesive composition, comprising:
an acid group-containing polymerizable monomer (A);
a hydrophobic polymerizable monomer (B) having no acid group; and
a water-soluble photopolymerization initiator (C) having a solubility of 10 g/L or more in water at 25° C.,
wherein the water-soluble photopolymerization initiator (C) is at least one selected from the group consisting of a compound represented by the following formula (1) and a compound represented by the following formula (2):

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently a linear or branched alkyl group comprising 1 to 4 carbon atoms or a halogen atom;
M is a hydrogen ion, an alkali metal ion, an alkaline-earth metal ion, a magnesium ion, a pyridinium ion comprising an optionally substituted pyridine ring, or an ammonium ion represented by HN + R 7 R 8 R 9 , wherein R 7 , R 8 , and R 9 are each independently an organic group or a hydrogen atom; and
n represents 1 or 2.

2. The non-solvent dental adhesive composition of claim 1 , further comprising a hydrophilic polymerizable monomer (D) having no acid group.

3. The non-solvent dental adhesive composition of claim 2 , wherein a content of the hydrophilic polymerizable monomer (D) having no acid group with respect to a total mass of the hydrophobic polymerizable monomer (B) having no acid group and the hydrophilic polymerizable monomer (D) having no acid group is 50 mass % or less.

4. The non-solvent dental adhesive composition of claim 1 ,
wherein the water-soluble photopolymerization initiator (C) comprises the compound represented by the formula (1).

5. The non-solvent dental adhesive composition of claim 1 , wherein the acid group-containing polymerizable monomer (A) is a phosphate group-containing polymerizable monomer.

6. The non-solvent dental adhesive composition of claim 1 , further comprising a water-insoluble photopolymerization initiator (E) having a solubility of less than 10 g/L in water at 25° C.

7. The non-solvent dental adhesive composition of claim 6 , wherein a mass ratio between the water-soluble photopolymerization initiator (C) and the water-insoluble photopolymerization initiator (E) is 10:1 to 1:10.

8. A dental bonding material, comprising the non-solvent dental adhesive composition of claim 1 .

9. A self-adhesive dental composite resin, comprising the non-solvent dental adhesive composition of claim 1 .

10. A dental cement, comprising the non-solvent dental adhesive composition of claim 1 .

11. The non-solvent dental adhesive composition of claim 1 , wherein the water-soluble photopolymerization initiator (C) comprises the compound represented by the formula (2).

Assignees

• Kuraray Noritake Dental Inc

Inventors

• Nojiri Yamato
• Kawashima Mitsunobu
• Matsuura Ryo
• MURAYAMA Ryota

Classifications

• C08F230/02

  containing phosphorus · CPC title

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• A61K6/891

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

• C08K5/5317

  Phosphonic compounds, e.g. R—P(:O)(OR')2 · CPC title