Adhesive monomers for dental materials

Patent metadata

Field	Value
Publication number	US-11311462-B2
Application number	US-201816488299-A
Country	US
Kind code	B2
Filing date	Mar 29, 2018
Priority date	Mar 31, 2017
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Provided are adhesive monomers for dental materials including compounds represented by the general formula (1) below, in which the core (X) and the terminal group (Y1) are bonded to each other directly or via the linking group (Z): X(Y1)n1a(Z—Y1)n1b(1) wherein n1a represents the number of terminal groups (Y1) directly bonded to the core (X), n1b represents the number of terminal groups (Y1) bonded to the core (X) via the linking group (Z), and the sum of n1a and n1b is equal to the valence of the core (X); the core (X), the linking group (Z) and the terminal group (Y1) are further defined. The adhesive monomers can enhance adhesive strength to the tooth in dental treatment, and impart high mechanical strength to cured products.

First claim

The invention claimed is:

1. An adhesive monomer for dental materials comprising a compound represented by the general formula (1) below, in which the core (X) below and the terminal group (Y1) below are bonded to each other directly or via the linking group (Z) below:
X(Y1) n 1a (Z—Y1) n 1b   (1)

wherein in the general formula (1), n 1a represents the number of terminal groups (Y1) directly bonded to the core (X), n 1b represents the number of terminal groups (Y1) bonded to the core (X) via the linking group (Z), and the sum of n 1a and n 1b is equal to the valence of the core (X);
the core (X) is a C 1-200 polyvalent organic group having a valence of 3 to 12 containing an oxygen atom or a nitrogen atom in which an atom bonded to the terminal group (Y1) or the linking group (Z) is the oxygen atom or the nitrogen atom;
the terminal group (Y1) is a phosphorus-containing group represented by the general formula (2) below, a phosphorus-containing group represented by the general formula (3) below, a (meth)acryloyl group-containing group (Y2) represented by the general formula (4) below, a (meth)acryloyl group, a C 1-20 hydrocarbon group or a hydrogen atom, and a plurality of terminal groups (Y1) may be the same as or different from each other, with the proviso that among all the terminal groups (Y1) in the compound represented by the general formula (1), one or more terminal groups are phosphorus-containing groups represented by the general formula (2) below or phosphorus-containing groups represented by the general formula (3) below, and one or more terminal groups are (meth)acryloyl group-containing groups (Y2); and
the linking group (Z) is a divalent group represented by the general formula (5) below, and when the compound represented by the general formula (1) contains a plurality of linking groups (Z), the linking groups (Z) may be the same as or different from each other;

wherein in the general formula (3), one end of the group is bonded to the core (X) or the linking group (Z), and the other end of the group is bonded to the core (X) or the linking group (Z) present in another compound represented by the general formula (1);

wherein in the general formula (4), R 4a represents a hydrogen atom or a methyl group, R 4b represents a C 2-6 linear alkylene group or a C 2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C 1-6 alkyl group or a (meth)acryloyloxymethylene group in place of a hydrogen atom; and

wherein in the general formula (5), n 5a , n 5b , n 5c and n 5d represent the unit numbers of respective repeating units, and are each 0 to 100, the sum of n 5a , n 5b , n 5c and n 5d is 1 to 100, the left end of the group is bonded to the core (X), and the right end of the group is bonded to the terminal group (Y1).

2. The adhesive monomer for dental materials according to claim 1 , wherein the terminal group (Y1) is a phosphorus-containing group represented by the general formula (2), a phosphorus-containing group represented by the general formula (3), a (meth)acryloyl group-containing group (Y2) represented by the general formula (4), or a hydrogen atom.

3. The adhesive monomer for dental materials according to claim 1 , wherein the terminal group (Y1) is a phosphorus-containing group represented by the general formula (2), a phosphorus-containing group represented by the general formula (3), or a (meth)acryloyl group-containing group (Y2) represented by the general formula (4).

4. The adhesive monomer for dental materials according to claim 1 , wherein in the linking group (Z) n 5a , n 5b , n 5c and n 5d are each 0 to 20, and the sum of n 5a , n 5b , n 5c and n 5d is 1 to 20.

5. The adhesive monomer for dental materials according to claim 1 , wherein the linking group (Z) is a divalent group represented by the general formula (6) below:

wherein in the general formula (6), n 6a , n 6b and n 6c represent the unit numbers of respective repeating units, and are each 0 to 20, the sum of n 6a , n 6b and n 6c is 1 to 20, the left end of the group is bonded to the core (X), and the right end of the group is bonded to the terminal group (Y1).

6. The adhesive monomer for dental materials according to claim 1 , wherein the linking group (Z) is a divalent group represented by the general formula (7) below:

wherein in the general formula (7), n 7a and n 7b represent the unit numbers of respective repeating units, and are each 0 to 20, the sum of n 7a and n 7b is 1 to 20, the left end of the group is bonded to the core (X), and the right end of the group is bonded to the terminal group (Y1).

7. The adhesive monomer for dental materials according to claim 1 , wherein the core (X) is at least one selected from the group consisting of groups represented by the general formulas (8a) to (8j) below:

wherein in the general formula (8g), n 8g is an integer of 1 to 40

8. The adhesive monomer for dental materials according to claim 1 , wherein the (meth)acryloyl group-containing group (Y2) is at least one selected from the group consisting of groups represented by the general formulas (4a) to (4f) below:

9. A monomer composition for dental materials comprising the adhesive monomer for dental materials according to claim 1 .

10. The monomer composition for dental materials according to claim 9 , wherein the monomer composition for dental materials is negative in a reverse mutation test.

11. A dental material comprising the adhesive monomer for dental materials according to claim 1 .

12. The dental material according to claim 11 , wherein the dental material is negative in a reverse mutation test.

13. A kit comprising the dental material according to claim 11 .

Assignees

• Mitsui Chemicals Inc
• Kulzer & Co Gmbh

Inventors

• Kosugi Yoko
• Matsumoto Akiko
• Yoshinaga Kazuhiko
• Gerlach Michael
• LECHMANN-DORN Maria
• Schneider Jutta
• Utterodt Andreas

Classifications

• A61K6/838

  Phosphorus compounds, e.g. apatite · CPC title

• A61K6/30

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

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08F222/102

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

• C08F20/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title