Adhesive composition

A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I and II:

• ##STR179## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR180## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R.sub.4 ' being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least three carbon atoms, and (b) 50 to 98.5 parts by weight of a vinyl monomer copolymerizable with said compound;
• 20 to 500 parts by weight of a filler;
• and 0.01 to 20 parts by weight of a curing agent.

A method of restoring a tooth cavity, comprising filling said cavity with an adhesive composition which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I and II:

• ##STR205## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR206## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R.sub.4 ' being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least three carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compoound;
• 20 to 500 parts by weight of a filler;
• and 0.01 to 20 parts by weight of 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 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II:

• ##STR207## wherein R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR208## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R.sub.4 ' being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least 3 carbon atoms, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound;
• 20 to 500 parts by weight of a filler;
• and 0.01 to 20 parts by weight of 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 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II:

• ##STR209## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR210## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R.sub.4 ' being the same or different, at least one R.sub.4 and R.sub.4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound;
• 20-500 parts by weight of a filler;
• and 0.01 to 20 parts by weight of a curing agent.

A method for protecting teeth against dental caries which comprises coating the tooth surface using a pit and a fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by one of formulas I or II:

• ##STR211## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR212## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom, or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, a plurality of R.sub.4 ' being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 50-98.5 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.

A method protecting teeth against dental caries which comprises coating the tooth surface using a pit and fissure sealant composition having adhesion to tooth which comprises 100 parts by weight of a polymerizable monomer comprising (a) 51 to 100 parts by weight of a compound represented by one of formulas I or II:

• ##STR213## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR214## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, which is unsubstituted or substituted by a halogen atom or hydroxyl, amino or carboxyl group, and b is an integer of 0 to 3, a plurality of R.sub.4 ' being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least 3 carbon atoms, and Z stands for --O--, --COO-- or --NH--, and (b) 0 to 49 parts by weight of a vinyl monomer copolymerizable with said compound, and 0.01 to 20 parts by weight of a curing agent.