Kuraray Noritake Dental Inc.

Kuraray Medical Inc.

Mitsuru Takei

Yamato Nojiri

Shumei Ishihara

Hidemi Nakayama

Kenji Hatanaka

Mariko Sugiura

Hiroki Shinoda

Kenji Suzuki

Mitsunobu Kawashima

Yasutaka Kudo

Naoki Nishigaki

Hiroshige Ishino

Michiya Kawana

Ai Hinamoto

Mariko Kawana

Akiko Tsuji

Kengo Futami

Yasujiro Ohara

Junichi Ohtsuki

The present invention provides a dental cement showing excellent storage stability, undergoing little change in paste properties during long-term storage, and having a small solidification risk during long-term storage. The present invention relates to a multi-part dental cement comprising: a first paste comprising an acid group-containing (meth)acrylic polymerizable monomer (a), a polyfunctional (meth)acrylic polymerizable monomer (b) containing no acid group, an oxidizing agent (c-1) of a chemical polymerization initiator, and a filler (d); and a second paste comprising a polyfunctional (meth)acrylic polymerizable monomer (b) containing no acid group, a reducing agent (c-2) of a chemical polymerization initiator, and a filler (e), wherein the filler (d) is treated with a surface treatment agent and has an average particle diameter of 0.01 to 50.0 &#x3bc;m, the surface treatment agent comprises a silane coupling agent (A) represented by the general formula (1) and an organosilazane (B) represented by the general formula (2).

Multi-part dental cement

The present invention provides a self-adhesive dental composite resin maintaining mechanical strength, showing excellent storage stability, undergoing little change in transparency and properties of the paste during long-term storage, and having a small solidification risk during long-term storage. The present invention relates to a self-adhesive dental composite resin comprising: an acid group-containing (meth)acrylic polymerizable monomer (a); a polyfunctional (meth)acrylic polymerizable monomer (b) containing no acid group; a photopolymerization initiator (c); and a filler (d), wherein the filler (d) is treated with a surface treatment agent and has an average particle diameter of 0.01 to 50.0 &#x3bc;m, the surface treatment agent comprises a silane coupling agent (A) represented by the following general formula (1):CH&#x2550;C(R)&#x2014;COO&#x2014;(CH)&#x2014;Si&#x2014;RR&#x2003;&#x2003;(1), andan organosilazane (B) represented by the following general formula (2):RRR&#x2014;Si&#x2014;NH&#x2014;Si&#x2014;RRR&#x2003;&#x2003;(2).

Self-adhesive dental composite resin

Provided herein is a self-etching dental adhesive that exhibits excellent adhesiveness not only to dentin untreated by phosphoric acid etching, but to dentin treated by phosphoric acid etching. The present invention relates to a dental adhesive containing a (meth)acrylamide compound (a), an asymmetric acrylamide-methacrylic acid ester compound (b), and an acid group-containing (meth)acrylic polymerizable monomer (c). The (meth)acrylamide compound (a) is at least one selected from the group consisting of compounds represented by general formula (1), and compounds represented by general formula (2). The asymmetric acrylamide-methacrylic acid ester compound (b) is a compound represented by general formula (3). (In the formulae, the meanings of the symbols are omitted.)

Dental adhesive

The present invention relates to providing a dental curable composition that, when cured, has high metal ion release ability and highly durable physical properties. The dental curable composition of the present invention includes: a sugar compound having an &#x2014;XM group, where &#x2014;X is an acid anion group and M is a metal cation; and a curable component.

Dental curable composition

The present invention provides a dental cement that exhibits excellent adhesiveness to dentin and has high mechanical strength. The present invention relates to a multi-part dental cement containing: an asymmetric acrylamide-methacrylic acid ester compound (a); an acid group-containing (meth)acrylic polymerizable monomer (b); a hydrophobic crosslinkable polymerizable monomer (c); a chemical polymerization initiator (d); and a filler (e). The asymmetric acrylamide-methacrylic acid ester compound (a) is represented by the following general formula (1): where X is an optionally substituted, linear or branched Cto Caliphatic group or an optionally substituted aromatic group, the aliphatic group is optionally interrupted by at least one linking group selected from the group consisting of &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;, &#x2014;O&#x2014;CO&#x2014;, &#x2014;NR&#x2014;, &#x2014;CO&#x2014;NR&#x2014;, &#x2014;NR&#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;NR&#x2014;, &#x2014;O&#x2014;CO&#x2014;NR&#x2014;, and &#x2014;NR&#x2014;CO&#x2014;NR&#x2014;, and Ris a hydrogen atom or an optionally substituted, linear or branched Cto Caliphatic group.

Dental cement

The present invention provides a dental adhesive exhibiting excellent initial bond strength and bond durability to both enamel and dentin. The present invention relates to a dental adhesive containing: an asymmetric acrylamide-methacrylic acid ester compound (a); an acid group-containing (meth)acrylic polymerizable monomer (b); and a water-soluble polymerizable monomer (c). The asymmetric acrylamide-methacrylic acid ester compound (a) is represented by the following general formula (1): where X is an optionally substituted, linear or branched Cto Caliphatic group or an optionally substituted aromatic group, the aliphatic group is optionally interrupted by at least one linking group selected from the group consisting of &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;, &#x2014;O&#x2014;CO&#x2014;, &#x2014;NR&#x2014;, &#x2014;CO&#x2014;NR&#x2014;, &#x2014;NR&#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;NR&#x2014;, &#x2014;O&#x2014;CO&#x2014;NR&#x2014;, and &#x2014;NR&#x2014;CO&#x2014;NR&#x2014;, and Ris a hydrogen atom or an optionally substituted, linear or branched Cto Caliphatic group.

The present invention provides a self-adhesive composite resin having excellent adhesiveness to tooth structures and excellent mechanical strength. The present invention relates to a self-adhesive dental composite resin containing: an asymmetric acrylamide-methacrylic acid ester compound (a); an acid group-containing (meth)acrylic polymerizable monomer (b); a hydrophobic crosslinkable polymerizable monomer (c); a photopolymerization initiator (d); and a filler (e). The asymmetric acrylamide-methacrylic acid ester compound (a) is represented by the following general formula (1): where X is an optionally substituted, linear or branched Cto Caliphatic group or an optionally substituted aromatic group, the aliphatic group is optionally interrupted by at least one linking group selected from the group consisting of &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;, &#x2014;O&#x2014;CO&#x2014;, &#x2014;NR&#x2014;, &#x2014;CO&#x2014;NR&#x2014;, &#x2014;NR&#x2014;CO&#x2014;, &#x2014;CO&#x2014;O&#x2014;NR&#x2014;, &#x2014;O&#x2014;CO&#x2014;NR&#x2014;, and &#x2014;NR&#x2014;CO&#x2014;NR&#x2014;, and Ris a hydrogen atom or an optionally substituted, linear or branched Cto Caliphatic group.

The present invention provides a one-part dental adhesive that exhibits excellent adhesive properties to both enamel and dentin and that has high storage stability and ambient-light stability. The present invention is a one-part dental adhesive including 1 to 30 weight % of a phosphoric acid group-containing monofunctional (meth)acrylate compound (a), 10 to 50 weight % of a water-soluble polymerizable monomer (b), 5 to 50 weight % of a hydrophobic crosslinkable (meth)acrylate compound (c), water (d), and a polymerization initiator (e). The water-soluble polymerizable monomer (b) includes a combination of a monofunctional (meth)acrylamide compound (b-1) having a particular structure and a water-soluble crosslinkable (meth)acrylic monomer (b-2). The weight ratio between the monofunctional (meth)acrylamide compound (b-1) and the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 10:1 to 1:5.

One-part dental adhesive

The present invention provides a dental curable composition which has excellent curability and which cures into a cured product that is less susceptible to discoloration by hydrogen sulfide in an oral environment. The present invention is a dental curable composition containing: a polymerizable monomer (a) having an acidic group, as a polymerizable monomer component; and a copper compound (b) and a benzotriazole compound (c) represented by the following general formula (1) and/or a benzimidazole compound (c) represented by the following general formula (2), as polymerization initiator components (symbols used in the formulae are as described in the description). 

The present invention provides a dental adhesive material kit having excellent bond durability. The present invention is represented by a dental adhesive material kit containing a dental aqueous adhesive composition (A) and a multi-part type dental nonaqueous curable composition (B). The dental aqueous adhesive composition (A) contains a polymerizable monomer (a) having an acidic group, an aliphatic polymerizable monomer (b) having no acidic group, water (c), and an amine-based reducing agent (d1) containing no sulfur atom. The multi-part type dental nonaqueous curable composition (B) contains an aliphatic polymerizable monomer (b) having no acidic group, an aromatic polymerizable monomer (e) having no acidic group, a powdery water-soluble reducing compound (f) containing a sulfur atom, an organic peroxide (g), and an amine-based reducing agent (d2) containing no sulfur atom.

Dental adhesive material kit

A cement for dental use, containing a first agent and a second agent, wherein both of the first agent and the second agent contain a polymerizable monomer (a) and a filler (b), wherein the first agent and/or the second agent further contains a photopolymerization initiator (c), wherein further as a chemical polymerization initiator (d), either one of the first agent and the second agent contains an oxidizing agent (f) and the other contains a reducing agent (g), the oxidizing agent (f) and the reducing agent (g) constituting a redox polymerization initiator, wherein the photopolymerization initiator (c) contains an &#x3b1;-diketone, and the photopolymerization initiator (c) is contained in a total amount of from 0.010 to 0.100 parts by weight, based on 100 parts by weight of the total amount of the polymerizable monomer (a), wherein the chemical polymerization initiator (d) is contained in a total amount of from 0.001 to 20 parts by weight, based on 100 parts by weight of the total amount of the polymerizable monomer (a), and wherein a cured product has a compression modulus immediately after photocuring of from 100 to 400 MPa, and a compression modulus after 24 hours from photocuring of 500 MPa or more. The cement for dental use of the present invention is suitably used for adhering the dentine and a crowning restorative material in the field of dental therapy, or the like.

Cement for dental applications

The present invention provides a redox-curing type composition that penetrates into a wet body, particularly into a tooth structure (dentin), is cured in an accelerated manner by the moisture contained in the wet body, thereby exhibits a higher bond strength than those of conventional redox-curing type compositions, and has satisfactory storage stability. The present invention is a redox-curing type composition including a polymerizable monomer (a) having an acidic group, a polymerizable monomer (b) having no acidic group, a powdery inorganic peroxide (c) with an average particle diameter of 0.01 to 50 &#x3bc;m, an amine-based reducing agent (d), and a polymerization accelerator (e). The amine-based reducing agent (d) includes an aromatic amine (d&#x2212;1) and an aliphatic amine (d&#x2212;2), and a weight ratio (d&#x2212;1):(d&#x2212;2) therebetween is 5:1 to 1:50.

Redox-curing type composition

The present invention provides a divided redox-curing type composition including a first part in which at least an oxidizing agent (b) is dissolved in a first radical monomer including a radical monomer (a) having an acidic group and/or a hydrophilic group; and a second part in which at least an aromatic sulfinate (d) is dispersed in a second radical monomer including a radical monomer (c) having neither an acidic group nor a hydrophilic group. According to the present invention, a redox-curing type composition capable of securing a time necessary for an adhesion operation and exhibiting high bond strength not only at the initial stage of adhesion but also over a long period of time thereafter in application to a wetting material such as a tooth or a bone as well as a tooth crown repairing material such as a metal or porcelain.

Divided redox-curing type composition

The invention provides a dental coating kit with high adhesiveness to teeth that contains a primer composition including an acidic group-containing polymeric monomer (a), water (b) and a water-soluble solvent (c) and a surface smoothing composition including a polyfunctional polymeric monomer (f), a volatile solvent (g) and a photopolymerization initiator (h); and a dental coating kit with high adhesiveness to teeth and minimally suffering from chipping and peeling off that contains a primer composition including an acidic group-containing polymeric monomer (a), water (b) and a water-soluble solvent (c), a coating composition including a polymeric monomer (d) and a photopolymerization initiator (e), and a surface smoothing composition including a polyfunctional polymeric monomer (f), a volatile solvent (g) and a photopolymerization initiator (h). Either dental coating kit is particularly useful as a kit for preventing stain and color return of a bleached tooth.

Growing community of inventors

Yokohama, Japan

Mitsuru Takei