Adhesive compositions

A method for restoring a carious tooth which comprises filling a tooth cavity with an adhesive composition which comprises 1 part by weight of (a) a compound of the general formula:

• ##STR28## wherein R.sub.1 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, COOR', wherein R' represents a hydrocarbon group of 1-20 carbon atoms optionally containing halogen or halogen;
• R.sub.2 is as defined for R.sub.1 ;
• R.sub.3 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, halogen or CN;
• R.sub.4 represents (COX.sub.2).sub.m1 (CO).sub.m2 (ZCO).sub.m3 (Z).sub.m4 Ra wherein Ra represents an organic residue of 6-60 carbon atoms and a valency of m+n;
• m1, m2, m3 and m4 each represents an integer of 0-4 and satisfies m1+m2+m3+m4.ltoreq.m;
• X.sub.2 represents O, S or NRb, wherein Rb represents H or alkyl of 1-4 carbon atoms and Z represents O or S;
• X.sub.1 is as defined for X.sub.2 ;
• m is an integer of 1-4;
• n is an integer of 2-6;
• and
• k is 0 or 1,
• - 199parts by weight of (b) a vinyl monomer copolymerizable with the aforesaid compound, 20-500 parts by weight per 100 parts by weight of the aforesaid polymerizable monomers [(a)+(b)] of (c) a filler, and 0.01-20 parts by weight per 100 parts by weight of the aforesaid polymerizable monomers [(a)+(b)] of (d) a curing agent.

A method for dental treatment which comprises bonding either a tooth and a dental restorative material or dental restorative materials to each other by employing an adhesive composition which comprises 1 part by weight of (a) a compound of the general formula:

• ##STR29## wherein R.sub.1 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, COOR', wherein R' represents a hydrocarbon group of 1-20 carbon atoms optionally containing halogen or halogen;
• R.sub.2 is as defined for R.sub.1 ;
• R.sub.3 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, halogen or CN;
• R.sub.4 represents (COX.sub.2).sub.m1 (CO).sub.m2 (ZCO).sub.m3 (Z).sub.m4 Ra wherein R.sub.a represents an organic residue of 6-60 carbon atoms and a valency of m+n;
• m1, m2, m3 and m4 each represents an integer of 0-4 and satisfies m1+m2+m3+m4.ltoreq.m;
• X.sub.2 represents O, S or NRb, wherein Rb represents H or alkyl of 1-4 carbon atoms and Z represents O or S;
• X.sub.1 is as defined for X.sub.2 ;
• m is an integer of 1-4;
• n is an integer of 2-6;
• and
• k is 0 or 1,
• - 199parts by weight of (b) a vinyl monomer copolymerizable with the aforesaid compound, 20-500 parts by weight per 100 parts by weight of the aforesaid polymerizable monomers [(a)+(b)] of (c) a filler, and 0.01-20 parts by weight per 100 parts by weight of the aforesaid polymerizable monomers [(a)+(b)] of (d) a curing agent.

A method for protecting teeth against dental caries which comprises coating the tooth surface using a composition having adhesion to teeth which comprises 1 part by weight of (a) a compound of the general formula:

• ##STR30## wherein R.sub.1 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, COOR', wherein R' represents a hydrocarbon group of 1-20 carbon atoms optionally containing halogen or halogen;
• R.sub.2 is as defined for R.sub.1 ;
• R.sub.3 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, halogen or CN;
• R.sub.4 represents(COX.sub.2).sub.m1 (CO).sub.m2 (ZCO).sub.m3 (Z).sub.m4 Ra wherein Ra represents an organic residue of 6-60 carbon atoms and a valency of m+n;
• m1, m2, m3 and m4 each represents an integer of 0-4 and satisfies m1+m2+m3+m4.ltoreq.m;
• X.sub.2 represents O, S or NRb, wherein Rb represents H or alkyl of 1-4 carbon atoms and Z represents O or S;
• X.sub.1 is as defined for X.sub.2 ;
• m is an integer of 1-4;
• n is an integer of 2-6;
• and
• k is 0 or 1,
• - 199parts by weight of (b) a vinyl monomer copolymerizable with the aforesaid compound, and 0.01-20 parts by weight per 100 parts by weight of the aforesaid polymerizable monomers [(a)+(b)] of (c) a curing agent.