Dental adhesive

Patent metadata

Field	Value
Publication number	US-10071028-B2
Application number	US-201515315497-A
Country	US
Kind code	B2
Filing date	Jun 10, 2015
Priority date	Jun 10, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention provides a dental adhesive exhibiting excellent initial bond strength and bond durability to both enamel and dentin. The present invention relates to a dental adhesive containing: an asymmetric acrylamide-methacrylic acid ester compound (a); an acid group-containing (meth)acrylic polymerizable monomer (b); and a water-soluble polymerizable monomer (c). The asymmetric acrylamide-methacrylic acid ester compound (a) is represented by the following general formula (1):

where X is an optionally substituted, linear or branched C 1 to C 6 aliphatic group or an optionally substituted aromatic group, the aliphatic group is optionally interrupted by at least one linking group selected from the group consisting of —O—, —S—, —CO—, —CO—O—, —O—CO—, —NR 1 —, —CO—NR 1 —, —NR 1 —CO—, —CO—O—NR 1 —, —O—CO—NR 1 —, and —NR 1 —CO—NR 1 —, and R 1 is a hydrogen atom or an optionally substituted, linear or branched C 1 to C 6 aliphatic group.

First claim

The invention claimed is:

1. A dental adhesive comprising:
an asymmetric acrylamide-methacrylic acid ester compound (a);
an acid group-containing (meth)acrylic polymerizable monomer (b); and
a water-soluble polymerizable monomer (c), wherein
the asymmetric acrylamide-methacrylic acid ester compound (a) is represented by formula (1):

wherein X is an optionally substituted, linear or branched C 1 to C 6 aliphatic group or an optionally substituted aromatic group, the aliphatic group is optionally interrupted by at least one linking group selected from the group consisting of —O—, —S—, —CO—, —O—CO—, —NR 1 —, —CO—NR 1 —, —NR 1 —CO—, —CO—O—NR 1 —, —O—CO—NR 1 —, and —NR 1 —CO—NR 1 —, and R 1 is a hydrogen atom or an optionally substituted, linear or branched C 1 to C 6 aliphatic group.

2. The dental adhesive according to claim 1 , wherein X is an optionally substituted, linear or branched C 1 to C 4 aliphatic group.

3. The dental adhesive according to claim 1 , wherein X is an optionally substituted, linear or branched C 2 to C 4 aliphatic group, and R 1 is a hydrogen atom.

4. The dental adhesive according to claim 1 , further comprising a hydrophobic crosslinkable polymerizable monomer (d).

5. The dental adhesive according to claim 1 , wherein the acid group-containing (meth)acrylic polymerizable monomer (b) is a phosphate group-containing (meth)acrylic polymerizable monomer.

6. The dental adhesive according to claim 1 , wherein the water-soluble polymerizable monomer (c) comprises at least one selected from the group consisting of a monofunctional (meth)acrylamide compound (c-1), 2-hydroxyethyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, and diacetone (meth)acrylamide, the monofunctional (meth)acrylamide compound (c-1) being represented by formula (2):

wherein R 2 and R 3 are each independently an optionally substituted, linear or branched C 1 to C 3 alkyl group, and R 4 is a hydrogen atom or a methyl group.

7. The dental adhesive according to claim 1 , wherein the water-soluble polymerizable monomer (c) is a monofunctional (meth)acrylamide compound (c-1) represented by formula (2):

wherein R 2 and R 3 are each independently an optionally substituted, linear or branched C 1 to C 3 alkyl group, and R 4 is a hydrogen atom or a methyl group.

8. The dental adhesive according to claim 1 , wherein a weight ratio between the water-soluble polymerizable monomer (c) and the asymmetric acrylamide-methacrylic acid ester compound (a) is 10:1 to 1:10.

Assignees

• Kuraray Noritake Dental Inc

Inventors

• Nojiri Yamato
• Takei Mitsuru

Classifications

• C08F22/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C08F220/346

  and further oxygen · CPC title

• A61K6/884 Primary

  comprising natural or synthetic resins · CPC title

• A61K6/887

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