Dental curable composition including chain transfer agent

Patent metadata

Field	Value
Publication number	US-11737957-B2
Application number	US-201816117044-A
Country	US
Kind code	B2
Filing date	Aug 30, 2018
Priority date	Jul 3, 2014
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

A dental curable composition capable of use as a dental material that can substitute part or all of a natural tooth, in particular, a resin material for dental cutting and machining in the field of dental care. When a block shape usable as the resin material is produced, while mechanical properties and aesthetic properties required for a crown prosthetic appliance are maintained, the dental curable composition can be molded and processed with pressure and heating while strain generated in the block is reduced and no cracks and chipping occur. The dental curable composition includes (a) a polymerizable monomer and (b) a filler in a weight ratio of 10:90 to 70:30, and 0.01 to 10 parts by weight of (c) a polymerization initiator and 0.001 to 1 part by weight of (d) a chain transfer agent being a terpenoid compound based on 100 parts by weight of the polymerizable monomer (a).

First claim

What is claimed is:

1. A dental curable composition for a resin material for dental cutting and machining comprising:
(a) a polymerizable monomer and (b) a filler in a weight ratio of 10:90 to 70:30, and 0.01 to 10 parts by weight of (c) a polymerization initiator and 0.1 to 0.5 part by weight of (d) a chain transfer agent being a terpenoid compound based on 100 parts by weight of the polymerizable monomer (a),
wherein the polymerization initiator (c) consists of a thermal polymerization initiator,
wherein an average particle size of the filler (b) is in a range from 0.5 to 100 μm,
wherein the filler (b) consists of a member selected from the group consisting of an inorganic filler, a polyvinyl acetate, a polyethylene glycol, a polypropylene glycol, a polyvinyl alcohol, and combinations thereof, and
wherein the dental curable composition is:
a two part dental curable composition wherein neither of the two parts is a powder component containing the polymerization initiator (c).

2. The dental curable composition according to claim 1 , wherein the dental curable composition comprises 0.1 to 5 parts by weight of the polymerization initiator (c) based on 100 parts by weight of the polymerizable monomer (a).

3. The dental curable composition according to claim 1 , wherein the dental curable composition comprises 0.1 to 2 parts by weight of the polymerization initiator (c) based on 100 parts by weight of the polymerizable monomer (a).

4. The dental curable composition according to claim 1 , wherein the thermal polymerization initiator is an organic peroxide and/or an azo compound.

5. The dental curable composition according to claim 1 , wherein the thermal polymerization initiator is at least one thermal polymerization initiator selected from a group consisting of benzoyl peroxide, p-chlorobenzoyl peroxide, 2,4-dichlorobenzoyl peroxide, acetyl peroxide, lauroyl peroxide, tert-butyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane, 2,5-dihydroperoxide, methyl ethyl ketone peroxide, tert-butylperoxybenzoate, azobisisobutyronitrile, azobis(methyl isobutyrate) and azobiscyanovaleric acid.

6. The dental curable composition according to claim 1 , wherein the thermal polymerization initiator is at least one thermal polymerization initiator selected from a group consisting of benzoyl peroxide, p-chlorobenzoyl peroxide, 2,4-dichlorobenzoyl peroxide, acetyl peroxide, lauroyl peroxide, tert-butyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane, 2,5-dihydroperoxide, methyl ethyl ketone peroxide and tert-butylperoxybenzoate.

7. The dental curable composition according to claim 1 , wherein the thermal polymerization initiator is at least one thermal polymerization initiator selected from a group consisting of azobisisobutyronitrile, azobis(methyl isobutyrate) and azobiscyanovaleric acid.

8. The dental curable composition according to claim 1 , wherein the chain transfer agent (d) is at least one of α-terpinene, β-terpinene and γ-terpinene.

9. A composite resin artificial tooth having a multilayer structure comprising:
at least one composite resin layer produced by a dental curable composition comprising:
(a) a polymerizable monomer and (b) a filler in a weight ratio of 10:90 to 70:30, and 0.01 to 10 parts by weight of (c) a polymerization initiator and 0.001 to 1 part by weight of (d) a chain transfer agent being a terpenoid compound based on 100 parts by weight of the polymerizable monomer (a),
wherein the polymerization initiator (c) consists of a thermal polymerization initiator,
wherein an average particle size of the filler (b) is in a range from 0.5 to 100 μm,
wherein the filler (b) consists of a member selected from the group consisting of an inorganic filler, a polyvinyl acetate, a polyethylene glycol, a polypropylene glycol, a polyvinyl alcohol, and combinations thereof, and
wherein the dental curable composition is:
a one part dental curable composition, or
a two part dental curable composition wherein neither of the two parts is a powder component containing the polymerization initiator (c); and
at least one acrylic resin layer comprising:
(e) a monofunctional (meth)acrylate polymerizable monomer,
(f) a non-crosslinkable (meth)acrylate polymer,
(c) a polymerization initiator, and
(d) a chain transfer agent.

10. The composite resin artificial tooth according to claim 9 , wherein the composite resin artificial tooth is prepared by molding and processing with pressure and heat in a mold.

11. A composite resin artificial tooth having a multilayer structure comprising a composite resin layer produced by a dental curable composition comprising:
(a) a polymerizable monomer and (b) a filler in a weight ratio of 10:90 to 70:30, and 0.01 to 10 parts by weight of (c) a polymerization initiator and 0.001 to 1 part by weight of (d) a chain transfer agent being a terpenoid compound based on 100 parts by weight of the polymerizable monomer (a),
wherein the polymerization initiator (c) consists of a thermal polymerization initiator,
wherein the filler (b) consists of a member selected from the group consisting of an inorganic filler, a polyvinyl acetate, a polyethylene glycol, a polypropylene glycol, a polyvinyl alcohol, and combinations thereof, and
wherein the structure comprises:
at least one of the composite resin layer; and
at least one acrylic resin layer comprising:
(e) a monofunctional (meth)acrylate polymerizable monomer,
(f) a non-crosslinkable (meth)acrylate polymer,
(c) a polymerization initiator, and
(d) a chain transfer agent.

12. The composite resin artificial tooth according to claim 11 , wherein the composite resin artificial tooth is molded in a mold.

Assignees

• Shofu Inc

Inventors

• Nakatsuka Toshiyuki
• Kitamura Toshio
• Goto Masanori
• Kai Tomohiro
• Takano Satoshi
• Jogetsu Yoshiyuki

Classifications

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61C13/087

  Artificial resin teeth {(A61C13/081 takes precedence; preparations A61K6/80)} · CPC title

• A61K6/60 Primary

  comprising organic or organo-metallic additives · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title

• C08K9/02

  Ingredients treated with inorganic substances · CPC title