Dental polymerizable monomers, compositions, adhesive dental materials and kits

Patent metadata

Field	Value
Publication number	US-11110038-B2
Application number	US-201916588283-A
Country	US
Kind code	B2
Filing date	Sep 30, 2019
Priority date	Mar 31, 2015
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

A dental adhesive curable composition containing a polymerizable monomer including a polymerizable monomer represented by formula (1′) and defined amounts of an acidic group-containing polymerizable monomer, a polymerization initiator containing a peroxide and a photopolymerization initiator, and a reductant containing a sulfinic acid compound and/or a salt thereof, and a filler:wherein the R groups, n and m are defined. A dental adhesive curable kit and a mobile tooth fixing material are also provided.

First claim

The invention claimed is:

1. A dental adhesive curable kit (αc) for preparing a dental adhesive curable composition (c), the dental adhesive curable composition (c) comprising a polymerizable monomer (III) comprising a polymerizable monomer (A) represented by the following general formula (1′) and an acidic group-containing polymerizable monomer (Bc), a polymerization initiator (Cc) comprising a peroxide (Cc1) and a photopolymerization initiator (Cc2), and a reductant (Dc) comprising a sulfinic acid compound (Dc2) and/or a salt thereof, and a filler (Fc), wherein
the content of the polymerizable monomer (A) is not less than 0.1 part by weight and not more than 99 parts by weight, and the content of the acidic group-containing polymerizable monomer (Bc) is 0.5 to 30 parts by weight based on the total weight of the polymerizable monomer (III);
the content of the peroxide (Cc1) is 0.01 to 20 parts by weight, the content of the photopolymerization initiator (Cc2) is 0.0001 to 15 parts by weight, and the content of the sulfinic acid compound (Dc2) or salt thereof is 0.001 to 15 parts by weight based on the polymerizable monomer (III); and
the content of the filler (Fc) is 5 to 95 wt % in the dental adhesive curable composition (c):

wherein R 1 and R 2 are each a hydrogen atom or a C 1-3 alkyl group, R 7 and R 8 are each a hydrogen atom or a methyl group, R b and R c are each independently a C 2-6 linear alkylene or C 2-6 linear oxyalkylene group optionally substituted with a C 1-3 alkyl group or a (meth) acryloyloxymethylene group in place of a hydrogen atom, and a moiety of the general formula (2c) below that is interposed between the two carbamoyl groups in the general formula (1′) is a structure represented by any of the general formulas (RA) and (RD) below:

the dental adhesive curable kit (αc) comprising at least a first composition and a second composition,
at least one of the first composition and the second composition including the polymerizable monomer (A),
the first composition including the reductant (Dc),
the second composition including the acidic group-containing polymerizable monomer (Bc) and the polymerization initiator (Cc).

2. A mobile tooth fixing material (βd) comprising a dental adhesive composition (d), the dental adhesive composition (d) including a polymerizable monomer (A) represented by the following general formula (1″), a polymerizable monomer (Bd) having at least one acidic group in the molecule, and a photopolymerization initiator (Cd):

wherein R a is a divalent C 6-9 bridged cyclic hydrocarbon group, R 1 and R 2 are each a hydrogen atom or a methyl group, R 3 , R 4 , R 5 and R 6 are each a hydrogen atom or a hydrocarbon group, R 7 and R 8 are each a hydrogen atom, m and n are each independently 0 to 4, and R b and R c are each independently a C 2-6 linear alkylene or C 2-6 linear oxyalkylene group optionally substituted with a C 1-3 alkyl group or a (meth)acryloyloxymethylene group in place of a hydrogen atom.

3. A mobile tooth fixing material (βd) according to claim 2 ,
wherein a cured product that is obtained by the following method and that is subjected to a three-point bending test exhibits a breaking energy of not less than 65 mJ,
the cured product being obtained by packing the dental adhesive composition (d) into a 2×2×25 mm mold, which is brought into press contact with a polypropylene film and a glass plate, irradiating nine points on each of front and back sides with light for 10 seconds, and polishing a surface of the cured product with #320 waterproof abrasive paper,
the three-point bending test being performed such that the obtained cured product is soaked in water at 37° C. overnight, and thereafter is subjected to the test at a crosshead speed of 1.0 mm/min; and
wherein a test piece that is obtained by the following method and that is subjected to a tensile adhesion test exhibits a tensile bond strength of not less than 3 MPa,
the test piece being obtained by applying the dental adhesive composition (d) on a bonding tooth face and curing the dental adhesive composition (d) by irradiation with light for 10 seconds, the bonding tooth face being obtained from a bovine front lower tooth having its flat enamel face exposed that is washed with water and dried and having a defined circular bonding area 4.8 mm in diameter,
the tensile adhesion test being performed such that the obtained test piece is soaked in water at 37° C. overnight, and thereafter is subjected to the test at a crosshead speed of 2 mm/min.

4. The dental adhesive curable kit (αc) according to claim 1 , wherein the content of the acidic group-containing polymerizable monomer (Bc) is 1 to 10 parts by weight based on the total weight of the polymerizable monomer (III).

Assignees

• Mitsui Chemicals Inc
• Sun Medical Co Ltd

Inventors

• Yoshinaga Kazuhiko
• Tanabe Yoshimitsu
• Kinoshita Shinsuke
• Mitamura Takenori
• Murai Hiroki
• Yokoyama Takeshi
• Kamimoto Yoshihisa
• Ori Tatsuya
• Shimizu Hirohisa
• Arata Masami
• Tsuchikawa Masuji
• Miyamori Sayaka
• Katsura Yoshiaki

Classifications

• A61K6/00

  Preparations for dentistry · CPC title

• A61K6/30 Primary

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C08L35/02 Primary

  Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence) · CPC title

• C07C271/20

  to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title