Kuraray Co., Ltd.

Yoshinori Nagase

Junichi Yamauchi

Ikuo Omura

Fumiko Uemura

Kyoichiro Shibatani

Eiji Ikeguchi

An adhesive composition comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 100 parts by weight of a compound represented by general formula I or II: ##STR1## 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 ##STR2## 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, and optionally replaced 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 ' (when b is 2 or 3) being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least three carbon atoms, and (b) 0 to 98.5 parts by weight of a vinyl monomer copolymerizable with the above compound; and 0.01 to 20 parts by weight of a curing agent. It shows a superior adhesive strength on any of hard tissues in a living body, such as teeth and bones, metals, organic polymers and ceramics. It maintains a high adhesive strength for a long time even if it is exposed to moisture, or immersed in water. It is particularly effective for use in dentistry, though it is useful for a variety of other purposes, too.

Adhesive composition

An adhesive composition comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 50 parts by weight of a compound represented by general formula I or II: ##STR1## 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 ##STR2## 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, and optionally replaced 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 ' (when b is 2 or 3) 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 the above compound; and 0.01 to 20 parts by weight of a curing agent. It shows a superior adhesive strength on any of hard tissues in a living body, such as teeth and bones, metals, organic polymers and ceramics. It maintains a high adhesive strength for a long time even if it is exposed to moisture, or immersed in water. It is particularly effective for use in dentistry, though it is useful for a variety of other purposes, too.

Phosphate monoester adhesive composition

This invention provides an adhesive composition which comprises 1 part by weight of (a) a compound of the general formula: ##STR1## 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;

Adhesive compositions

This invention provides an adhesive composition which comprises 1 part by weight of (a) a compound of the general formula: ##STR1## 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:

A cement composition which comprises a filler, a binder to be used in admixture with the filler, and a curing agent for polymerizing the binder, which is characterized by that the binder comprises, based on the total weight of the binder, 20-100% by weight of (A) a free-radical polymerizable monomer of the following formula: ##STR1## wherein R is a hydrogen atom or a methyl group and X is an organic residue having 1-48 carbon atoms, and 0-80% by weight of (B) a mono-, di- or tri-functional free-radical polymerizable monomer which is copolymerizable with the above monomer (A) is disclosed. By using the above binder, the filler is firmly bonded with each other and gives a cured product having high compressive strength and abrasion resistance. The cement composition is especially useful as dental restorative materials.

Method for filling tooth cavities employing a polymerizable urethane

Cement compositions

A caries detector, comprising a solution of a dye selected from the group consisting of Phloxine B (CI 45410), Phloxine BK (the corresponding dipotassium salt of CI 45410), Acid Red (CI 45100), Fast Acid Magenta (CI 17200), Fast Green FCF (CI 42053) and Rhodamine B (CI 45170) in a solvent.

Dental caries detection

The present invention provides a dental material comprising a polymerizable methacrylate monomer mixture and a curing agent, said polymerizable methacrylate monomer mixture containing a compound represented by the formula ##STR1## wherein R is H or methyl and n is integer of 1-4, in an amount of 5-50% by weight based on the whole polymerizable monomer mixture. Said dental material is useful as a filling material, a dental adhesive primer, and a pit and fissure sealant.

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Kurashiki, Japan

Yoshinori Nagase