Dental polyfunctional monomers and dental hydroxyl group-containing monomers

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 C 1-200 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 C 1-20 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.

1 . A dental polyfunctional monomer comprising a compound represented by the general formula (8A) below, in which the core (X) below and the terminal group (Y2A) below are bonded to each other directly or via the linking group (Z) below:
   X(Y2A) n   8aA (Z—Y2A) n   8bA   (8A)
   (in the general formula (8A), n 8aA  represents the number of terminal groups (Y2A) directly bonded to the core (X), n 8bA  represents the number of terminal groups (Y2A) bonded to the core (X) via the linking group (Z), and the sum of n 8aA  and n 8bA  is equal to the valence of the core (X);   the core (X) is a C 1-200  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 (Y2A) or the linking group (Z) is the oxygen atom or the nitrogen atom;   the terminal group (Y2A) is a (meth)acryloyl group-containing group (Y3) represented by the general formula (9) below, a (meth)acryloyl group or a C 1-20  hydrocarbon group, and a plurality of terminal groups (Y2A) may be the same as or different from each other, with the proviso that among all the terminal groups (Y2A) in the compound represented by the general formula (8A), three or more terminal groups are (meth)acryloyl group-containing groups (Y3) or (meth)acryloyl groups, and one or more terminal groups are (meth)acryloyl group-containing groups (Y3); 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 (8A) 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 (Y2A)). 
       
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . The dental polyfunctional monomer according to  claim 1 , wherein the core (X) is an organic group having a valence of 3 to 12. 
     
     
         8 . The dental polyfunctional monomer according to  claim 1 , wherein the core (X) is at least one selected from the group consisting of groups represented by the general formulas (6a) to (6j) below: 
       
         
           
           
               
               
           
         
         (in the general formula (6g), n 6g  is an integer of 1 to 40). 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . The dental polyfunctional 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: 
       
         
           
           
               
               
           
         
       
     
     
         10 . A dental polyfunctional monomer which is a product of reaction of a compound represented by the general formula (1A) below, in which the core (X) below and the terminal group (Y1A) below are bonded to each other directly or 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 (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 (1A) below)=1:
   X(Y1A) n   1aA (Z—Y1A) n   1bA   (1A)
   (in the general formula (1A), n 1aA  represents the number of terminal groups (Y1A) directly bonded to the core (X), n 1bA  represents the number of terminal groups (Y1A) bonded to the core (X) via the linking group (Z), and the sum of n 1aA  and n 1bA  is equal to the valence of the core (X);   the core (X) is a C 1-200  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 (Y1A) or the linking group (Z) is the oxygen atom or the nitrogen atom;   the terminal group (Y1A) is a (meth)acryloyl group, a C 1-20  monovalent hydrocarbon group or a hydrogen atom, and a plurality of terminal groups (Y1A) may be the same as or different from each other, with the proviso that among the terminal groups (Y1A) in the compound represented by the general formula (1A), three or more terminal groups are hydrogen atoms or (meth)acryloyl groups, 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 (1A) 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 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 (Y1A)); 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). 
       
     
     
         11 . The dental polyfunctional monomer according to  claim 10 , wherein the terminal group (Y1A) is a hydrogen atom. 
     
     
         12 . (canceled) 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . (canceled) 
     
     
         17 . The dental polyfunctional monomer according to  claim 10 , 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: 
       
         
           
           
               
               
           
         
       
     
     
         18 . A dental monomer composition comprising the dental polyfunctional monomer according to  claim 1 . 
     
     
         19 . (canceled) 
     
     
         20 . A dental material comprising the dental polyfunctional monomer according to  claim 1 . 
     
     
         21 . (canceled) 
     
     
         22 . A cured product obtained by curing the dental material according to  claim 20 . 
     
     
         23 . (canceled) 
     
     
         24 . A dental hydroxyl group-containing monomer comprising a compound represented by the general formula (8B) below, in which the core (X) below and the terminal group (Y2B) below are bonded to each other directly or 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);   the core (X) is a C 1-200  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 (Y2B) or the linking group (Z) is the oxygen atom or the nitrogen atom;   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)). 
       
     
     
         25 . (canceled) 
     
     
         26 . (canceled) 
     
     
         27 . (canceled) 
     
     
         28 . (canceled) 
     
     
         29 . The dental hydroxyl group-containing monomer according to  claim 24 , wherein the core (X) is an organic group having a valence of 3 to 12. 
     
     
         30 . The dental hydroxyl group-containing monomer according to  claim 24 , wherein the core (X) is at least one selected from the group consisting of groups represented by the general formulas (6a) to (6j) below: 
       
         
           
           
               
               
           
         
         (in the general formula (6g), n 6g  is an integer of 1 to 40). 
       
       
         
           
           
               
               
           
         
       
     
     
         31 . The dental hydroxyl group-containing monomer according to  claim 24 , 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: 
       
         
           
           
               
               
           
         
       
     
     
         32 . 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 directly or 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);   the core (X) is a C 1-200  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 (Y1B) or the linking group (Z) is the oxygen atom or the nitrogen atom;   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 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 (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). 
       
     
     
         33 . The dental hydroxyl group-containing monomer according to  claim 32 , wherein the terminal group (Y1B) is a hydrogen atom. 
     
     
         34 . (canceled) 
     
     
         35 . (canceled) 
     
     
         36 . (canceled) 
     
     
         37 . (canceled) 
     
     
         38 . (canceled) 
     
     
         39 . The dental hydroxyl group-containing monomer according to  claim 32 , 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: 
       
         
           
           
               
               
           
         
       
     
     
         40 . A dental monomer composition comprising the dental hydroxyl group-containing monomer according to  claim 24 . 
     
     
         41 . (canceled) 
     
     
         42 . A dental material comprising the dental hydroxyl group-containing monomer according to  claim 24 . 
     
     
         43 . (canceled) 
     
     
         44 . (canceled)