Dental polyfunctional monomers and dental hydroxyl group-containing monomers

Patent metadata

Field	Value
Publication number	US-11406571-B2
Application number	US-202117166135-A
Country	US
Kind code	B2
Filing date	Feb 3, 2021
Priority date	Mar 31, 2017
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

Provided are monomers useful for dental materials that include a compound in which a core and a specific terminal group are bonded to each other directly or via a linking group, wherein the core is a C1-200 polyvalent organic group having a valence of not less than 3 containing an oxygen atom or a nitrogen atom in which an atom bonded to the terminal group or the linking group is the oxygen atom or the nitrogen atom; the terminal group is a specific (meth)acryloyl group-containing group, a (meth)acryloyl group, a C1-20 hydrocarbon group or a hydrogen atom, and the terminal group needs to meet specific requirements; and the linking group is a specific divalent group, and when the compound contains a plurality of linking groups, the linking groups may be the same as or different from each other. Compositions, dental materials and kits are also provided.

First claim

The invention claimed is:

1. A dental hydroxyl group-containing monomer a represented by the general formula (8B) below, in which the core (X) below and the terminal group (Y2B) below are bonded to each other via the linking group (Z) below:
X(Y2B) n 8aB (Z-Y2B) n 8bB   (8B)

in the general formula (8B), n 8aB represents the number of terminal groups (Y2B) directly bonded to the core (X), n 8bB represents the number of terminal groups (Y2B) bonded to the core (X) via the linking group (Z), and the sum of n 8aB and n 8bB is equal to the valence of the core (X), wherein n 8aB is 0;
the core (X) is at least one selected from the group consisting of groups represented by the general formulas (6a) to (6j) below:

the terminal group (Y2B) is a (meth)acryloyl group-containing group (Y3) represented by the general formula (9) below, a (meth)acryloyl group, a C 1-20 hydrocarbon group or a hydrogen atom, and a plurality of terminal groups (Y2B) may be the same as or different from each other, with the proviso that among all the terminal groups (Y2B) in the compound represented by the general formula (8B), one or more terminal groups are (meth)acryloyl group-containing groups (Y3), and one or more terminal groups are hydrogen atoms; and
the linking group (Z) is a divalent group represented by the general formula (2) below, and when the compound represented by the general formula (8B) contains a plurality of linking groups (Z), the linking groups (Z) may be the same as or different from each other;

in the general formula (9), R 9a represents a hydrogen atom or a methyl group, R 9b 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

in the general formula (2), n 2a , n 2b , n 2c and n 2d represent the unit numbers of respective repeating units, and are each 0 to 100, the sum of n 2a , n 2b , n 2c and n 2d 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 (Y2B).

2. The dental hydroxyl group-containing monomer according to claim 1 , wherein the core (X) has a valence of 3 to 12.

3. The dental hydroxyl group-containing monomer according to claim 1 , wherein the (meth)acryloyl group-containing group (Y3) is at least one selected from the group consisting of groups represented by the general formulas (9a) to (9f) below:

4. A dental hydroxyl group-containing monomer which is a product of reaction of a compound represented by the general formula (1B) below, in which the core (X) below and the terminal group (Y1B) below are bonded to each other via the linking group (Z) below, with a (meth)acryloyl group-containing isocyanate compound represented by the general formula (3) below, under a condition of 1/(the number of active protons bonded to oxygen atoms and nitrogen atoms present in the compound represented by the general formula (1B) below)≤(the number of isocyanate groups present in the compound represented by the general formula (3) below)/(the number of active protons bonded to oxygen atoms and nitrogen atoms present in the compound represented by the general formula (1B) below)<1:
X(Y1B) n 1aB (Z-Y1B) n 1bB   (1B)

in the general formula (1B), n 1aB represents the number of terminal groups (Y1B) directly bonded to the core (X), n 1bB represents the number of terminal groups (Y1B) bonded to the core (X) via the linking group (Z), and the sum of n 1aB and n 1bB is equal to the valence of the core (X), wherein n 1aB is 0;
the core (X) is at least one selected from the group consisting of groups represented by the general formulas (6a) to (6j) below:

the terminal group (Y1B) is a (meth)acryloyl group, a C 1-20 monovalent hydrocarbon group or a hydrogen atom, and a plurality of terminal groups (Y1B) may be the same as or different from each other, with the proviso that among the terminal groups (Y1B) in the compound represented by the general formula (1B), two or more terminal groups are hydrogen atoms; and
the linking group (Z) is a divalent group represented by the general formula (2), and when the compound represented by the general formula (1B) contains a plurality of linking groups (Z), the linking groups (Z) may be the same as or different from each other;

in the general formula (2), n 2a , n 2b , n 2c and n 2d represent the unit numbers of respective repeating units, and are each 0 to 100, the sum of n 2a , n 2b , n 2c and n 2d is 0 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 (Y1B); and

in the general formula (3), R 3a represents a hydrogen atom or a methyl group, R 3b 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.

5. The dental hydroxyl group-containing monomer according to claim 4 , wherein each of the plurality of the terminal groups (Y1B) is a hydrogen atom.

6. The dental hydroxyl group-containing monomer according to claim 4 , wherein the (meth)acryloyl group-containing isocyanate compound represented by the general formula (3) is at least one selected from the group consisting of compounds represented by the general formulas (3a) to (3f) below:

7. A dental monomer composition comprising the dental hydroxyl group-containing monomer according to claim 1 .

8. A dental material comprising the dental hydroxyl group-containing monomer according to claim 1 .

Assignees

• Mitsui Chemicals Inc

Inventors

• Kosugi Yoko
• Matsumoto Akiko
• Yoshinaga Kazuhiko

Classifications

• A61K6/30

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

• C07C271/16

  to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms · CPC title

• A61K6/887 Primary

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

• C07C271/20 Primary

  to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• A61K6/40

  Primers (for dental adhesives A61K6/30) · CPC title