Dental composition

Abstract

Dental composition comprising (i) a particulate filler; (ii) a polymerizable hydrolysis-stable compound of the following formula (1) AX n wherein A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups, X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2) wherein R 1 and R 2 are independent from each other and represent a hydrogen atom, a C 1-6 alkyl group or a group —(CH 2 ) m —Z, wherein Z is COOM, OPO 3 M 2 , PO 3 M 2 , SO 3 M, and M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6, L is a bond, a C 1-6 alkylene group; and n is an integer of at least 1; provided that at least one X cannot be a (meth)acryl group; and (iii) an initiator system.

1 . Dental composition comprising
 (i) a particulate filler;   (ii) a polymerizable hydrolysis-stable compound of the following formula (1),
   AX n   (1)
 
 wherein 
 A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups, 
 X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2) 
   
       
         
           
           
               
               
           
         
         
           wherein 
           R 1  and R 2  are independent from each other and represent a hydrogen as a C 1-6  alkyl group or a group —(CH 2 ) m —Z, wherein Z is COOM, OPO 3 M 2 , SO 3 M, and M is independently a hydrogen atom or a metal atom, and in is an integer of from 0 to 6, 
           L is a bond, a C 1-6  alkylene group; and 
           n is an integer of at least 1; 
           provided that at least one X cannot be a (meth)acryl group; and 
         
         (iii) an initiator system. 
       
     
     
         2 . The dental composition according to  claim 1 , wherein the linker group is a linear or branched monomeric, oligomeric, polymeric or copolymeric group containing nitrogen atoms or nitrogen containing functional groups at the terminal positions for forming an amide bond, a urea group or a thiourea group with a moiety X. 
     
     
         3 . The dental composition according to  claim 1 , wherein the polymerizable compound of formula (1) contains one or more acidic groups selected from carboxylic acid groups, phosphoric acid groups, sulfonic acid groups or phosphoric acid ester groups. 
     
     
         4 . The dental composition according to  claim 1 , wherein the linker group is a polyamide group obtainable by a process comprising the step of a step-growth polymerization of a mixture containing a diamine of the following formula (3) and a compound of the following formula (4) having at least two carboxylic acid groups, said carboxylic acid groups may be present in the form of an anhydride, optionally in the presence of a compound of the following formula (5):
   R 3 (NHR′) y   (3)
   wherein   R 3  represents an y-valent C 2-20  straight-chain, branched or cyclic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from hydroxyl groups, thiol groups and amino groups;   R′ represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group; and   y represents an integer of at least 2;
   MOOC—R 4 —COOM  (4)
 
   wherein R 4  represents a C 1-20  straight-chain, branched, cyclic or aromatic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups, hydroxyl groups, thiol groups and amino groups, and the M which may be the same or different, independently represent a hydrogen atom or a metal atom;   
       
         
           
           
               
               
           
         
         wherein L, R 1  and R 2  are as defined in  claim 1 , and Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R 1  or R 2  and the adjacent carbonyl group. 
       
     
     
         5 . The dental composition according to  claim 1 , wherein the linker group is a polyoxyalkylene group containing nitrogen atoms at the terminal positions. 
     
     
         6 . The dental composition according to  claim 1 , wherein the water soluble polymerizable hydrolysis-stable compound of formula (1) has an average molecular weight of from 300 to 10,000. 
     
     
         7 . The dental composition according to  claim 1 , wherein n is at least 2. 
     
     
         8 . The dental composition according to  claim 1 , which contains a fluoride containing compound. 
     
     
         9 . The dental composition according to  claim 1  wherein the particulate filler is an inorganic particulate filler selected from the group of glass, metal oxides, metal hydroxides, salts and mixtures thereof. 
     
     
         10 . The dental composition according to  claim 1 , which provides a shear strength (ISO/TS 11405 (2003)) after curing to dentin or enamel of at least 3 MPa. 
     
     
         11 . The dental composition according to  claim 1 , which is a one-pack composition. 
     
     
         12 . The dental composition according to  claim 1 , wherein R 1  and R 2  in formula (2) are independent from each other and represent a hydrogen atom, a C 1-6  alkyl group or a group —(CH 2 ) m —COOM, wherein M is hydrogen atom or a metal atom, and m is an integer of from 0 to 6. 
     
     
         13 . Use of a compound of formula (1) as defined in  claim 1 , for the preparation of a dental composition. 
     
     
         14 . The use according to  claim 13 , wherein the dental composition is a dental restorative or dental prosthetic composition. 
     
     
         15 . Process for preparing a compound of formula (1) as defined by  claim 1 , which comprises a step of a step-growth. polymerization of a mixture containing a diamine of the following formula (3) and a compound of the following formula (4) having at least two carboxylic acid groups, said carboxylic acid groups may be present in the form of an anhydride, optionally in the presence of a compound of the following formula (5):
   R 3 (NHR′) y   (3)
   wherein   R 3  represents an y-valent C 2-20  straight-chain, branched or cyclic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from hydroxyl groups, thiol groups and amino groups;   R′ represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group; and   y represents an integer of at least 2;
   MOOC—R 4 —COOM  (4)
 
   wherein R 4  represents a C 1-20  straight-chain, branched, cyclic or aromatic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups, hydroxyl groups, thiol groups and amino groups and the M which may be the same or different, independently represent a hydrogen atom or a metal atom;   
       
         
           
           
               
               
           
         
         wherein L, R 1  and R 2  are as defined in  claim 1 , and Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R 1  or R 2  and the adjacent carbonyl group. 
       
     
     
         16 . The dental composition according to  claim 1 , wherein the linker group is a linear or branched monomeric, oligomeric, polymeric or copolymeric group containing nitrogen atoms or nitrogen containing functional groups at the terminal positions fbr forming an amide bond, a urea group or a thiourea group with a moiety X; and
 wherein the linker group is a polyamide group obtainable by a process comprising the step of a step-growth polymerization of a mixture containing a diamine of the following formula (3) and a compound of the following formula (4) having at least two carboxylic acid groups, said carboxylic acid groups may be present in the form of an anhydride, optionally in the presence of a compound of the following formula (5):
   R 3 (NHR′) y   (3)
 
   wherein   R 3  represents an y-valent C 2-20  straight-chain, branched or cyclic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from hydroxyl groups, thiol groups and amino groups;   R′ represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group; and   y represents an integer of at least 2;
   MOOC—R 4 —COOM  (4)
 
   wherein R 4  represents a C 1-20  straight-chain, branched, cyclic or aromatic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups, hydroxyl groups, thiol groups and amino groups, and the M which may be the same or different, independently represent a hydrogen atom or a metal atom;   
       
         
           
           
               
               
           
         
         wherein L, R 1  and R 2  are as defined in  claim 1 , and Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R 1  or R 2  and the adjacent carbonyl group. 
       
     
     
         17 . The dental composition according to  claim 2 ,
 wherein the linker group is a polyamide group obtainable by a process comprising the step of a step-growth polymerization of a mixture containing a diamine of the following formula (3) and a compound of the following formula (4) having at least two carboxylic acid groups, said carboxylic acid groups may be present in the form of an anhydride, optionally in the presence of a compound of the following formula (5):
   R 3 (NHR′) y   (3)
 
   wherein   R 3  represents an y-valent C 2-20  straight-chain, branched or cyclic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from hydroxyl groups, thiol groups and amino groups;   R′ represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group; and   y represents an integer of at least 2;
   MOOC—R 4 —COO  (4)
 
   wherein R 4  represents a C 1-20  straight-chain, branched, cyclic or aromatic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups, hydroxyl groups, thiol groups and amino groups, and the M which may be the same or different, independently represent a hydrogen atom or a metal atom;   
       
         
           
           
               
               
           
         
         wherein L, R 1  and R 2  are as defined in  claim 1 , and Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R 1  or R 2  and the adjacent carbonyl group. 
       
     
     
         18 . The dental composition according to  claim 3 , wherein the linker group is a polyamide group obtainable by a process comprising the step of a step-growth polymerization of a mixture containing a diamine of the following formula (3) and a compound of the following formula (4) having at least two carboxylic acid groups, said carboxylic acid groups may be present in the form of an anhydride, optionally in the presence of a compound of the following formula (5):
   R 3 (NHR′) y   (3)
   wherein   R 3  represents an y-valent C 2-20  straight-chain, branched or cyclic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from hydroxyl groups, thiol groups and amino groups;   R′ represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group; and   y represents an integer of at least 2;
   MOOC—R 4 —COOM  (4)
 
   wherein R 4  represents a C 1-20  straight-chain, branched, cyclic or aromatic hydrocarbon group which may optionally contain from 1 to 6 heteroatoms selected from nitrogen, oxygen, or sulphur atoms in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups, hydroxyl groups, thiol groups and amino groups, and the M which may be the same or different, independently represent a hydrogen atom or a metal atom;   
       
         
           
           
               
               
           
         
         wherein L, R 1  and R 2  are as defined in  claim 1 , and Y is a leaving group or Y forms an intramolecular anhydride group together with a carboxyl group present in R 1  or R 2  and the adjacent carbonyl group.