Dental adhesive

Patent metadata

Field	Value
Publication number	US-10456333-B2
Application number	US-201615781745-A
Country	US
Kind code	B2
Filing date	Dec 6, 2016
Priority date	Dec 7, 2015
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

Provided herein is a self-etching dental adhesive that exhibits excellent adhesiveness not only to dentin untreated by phosphoric acid etching, but to dentin treated by phosphoric acid etching. The present invention relates to a dental adhesive containing a (meth)acrylamide compound (a), an asymmetric acrylamide-methacrylic acid ester compound (b), and an acid group-containing (meth)acrylic polymerizable monomer (c). The (meth)acrylamide compound (a) is at least one selected from the group consisting of compounds represented by general formula (1), and compounds represented by general formula (2). The asymmetric acrylamide-methacrylic acid ester compound (b) is a compound represented by general formula (3).

(In the formulae, the meanings of the symbols are omitted.)

First claim

The invention claimed is:

1. A dental adhesive comprising:
a (meth)acrylamide compound (a);
an asymmetric acrylamide-methacrylic acid ester compound (b); and
an acid group-containing (meth)acrylic polymerizable monomer (c),
wherein the (meth)acrylamide compound (a) is at least one compound selected from the group consisting of compounds represented by the following general formula (1), and compounds represented by the following general formula (2), and
wherein the asymmetric acrylamide-methacrylic acid ester compound (b) is a compound represented by the following general formula (3),

wherein R 1 represents a hydrogen atom or a methyl group, 1 represents an integer of 1 to 6, X represents an optionally substituted, linear or branched C 1 to C 8 alkylene group, the plurality of R 1 may be the same or different, and the plurality of X may be the same or different,

wherein m represents 2 or 3, R 1 and X are as defined above, the plurality of R 1 may be the same or different, and the plurality of X may be the same or different,

wherein Z is an optionally substituted, linear or branched C 1 to C 8 aliphatic group or an optionally substituted aromatic group, the aliphatic group being optionally interrupted by at least one linking group selected from the group consisting of —O—, —S—, —CO—, —CO—O—, —O—CO—, —NR 2 —, —CO—NR 2 —, —NR 2 —CO—, —CO—O—NR 2 —, —O—CONR 2 —, and —NR 2 —CO—NR 2 —, and R 2 represents a hydrogen atom, or an optionally substituted, linear or branched C 1 to C 8 aliphatic group.

2. The dental adhesive according to claim 1 , further comprising a hydrophilic polymerizable monomer (d).

3. The dental adhesive according to claim 1 , wherein the acid group-containing (meth)acrylic polymerizable monomer (c) is a phosphoric acid group-containing (meth)acrylic polymerizable monomer.

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

5. The dental adhesive according to claim 2 , wherein the hydrophilic polymerizable monomer (d) contains a monofunctional (meth)acrylamide compound (d-1) represented by the following general formula (4),

wherein R 3 and R 4 are each independently a C 1 to C 3 alkyl group, and R 5 is a hydrogen atom or a methyl group.

6. The dental adhesive according to claim 1 , wherein the (meth)acrylamide compound (a) is at least one selected from the group consisting of the following compounds (a1-1), (a1-3), (a1-5), and (a1-7);

7. The dental adhesive according to claim 1 , wherein the (meth)acrylamide compound (a) is at least one selected from the group consisting of the following compounds (a2-1), (a2-3), (a2-5), (a2-7), and (a2-21);

8. The dental adhesive according to claim 1 , wherein the (meth)acrylamide compound (a) is the following compound (a2-1);

9. The dental adhesive according to claim 1 , wherein the (meth)acrylamide compound (a) is the following compound (a2-21);

10. The dental adhesive according to claim 1 , wherein the asymmetric acrylamide-methacrylic acid ester compound (b) is a compound represented by the general formula (3) in which Z is an optionally substituted, linear or branched C 2 to C 4 aliphatic group.

11. The dental adhesive according to claim 1 , wherein the asymmetric acrylamide-methacrylic acid ester compound (b) is at least one selected from the group consisting of N-methacryloyloxyethylacrylamide, N-methacryloyloxypropylacrylamide, N-methacryloyloxybutylacrylamide, N-(1 -ethyl-(2-methacryloyloxy)ethyl)acrylamide, and N-(2-(2-methacryloyloxyethoxy)ethyl)acrylamide).

Assignees

• Kuraray Noritake Dental Inc

Inventors

• Nojiri Yamato
• Takei Mitsuru

Classifications

• A61K6/887

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

• A61K6/891 Primary

  Compounds obtained otherwise than 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

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09J133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title