Curable composition

• US 9,889,070 B2
• Filed: 03/19/2014
• Issued: 02/13/2018
• Est. Priority Date: 03/28/2013
• Status: Active Grant

• Current Assignee: Kuraray Noritake Dental Inc. (Kuraray Company Limited)
• Original Assignee: Kuraray Noritake Dental Inc. (Kuraray Company Limited)
• Inventors: Kashiki, Nobusuke, Suzuki, Kenji
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/779,134
• Publication Number:
  US 20160051450A1
• Time in Patent Office: 1,427 Days
• Field of Search: None
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: A61K 6/60 comprising organic or organo-metallic additives
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 22/10 Esters
• CPC Class Codes: C08F 22/38 Amides
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Abstract

The present invention provides a novel curable composition in which a reaction is caused to occur between a hydroperoxide and a thiourea compound to initiate polymerization of a radical polymerizable monomer and which has excellent adhesive properties, moderate curability, and excellent long-term storage stability. The present invention relates to a curable composition (A) containing: a radical polymerizable monomer (a1) having no acidic group; a hydroperoxide compound (a2); and at least one cyclic thiourea compound (a3) selected from the group consisting of a substituted ethylenethiourea compound (a3-1), a substituted propylenethiourea compound (a3-2), and a substituted butylenethiourea compound (a3-3) each having a specific structure with a cyclic structure moiety into which a substituent is introduced.

Claims

1. A curable composition (A), comprising:

a radical polymerizable monomer (a1) having no acidic group;

a hydroperoxide compound (a2); and

at least one cyclic thiourea compound (a3) selected from the group consisting of a substituted ethylenethiourea compound (a3-1), a substituted propylenethiourea compound (a3-2), and a substituted butylenethiourea compound (a3-3),

wherein

the substituted ethylenethiourea compound (a3-1) has a structure represented by the following formula (I);

2. The curable composition (A) according to claim 1, further comprising a filler (a4).

3. The curable composition (A) according to claim 1, wherein the radical polymerizable monomer (a1) having no acidic group is a (meth)acrylate polymerizable monomer and/or a (meth)acrylamide polymerizable monomer.

4. The curable composition (A) according to claim 1, further comprising an acidic group-containing radical polymerizable monomer (a5).

5. The curable composition (A) according to claim 1, further comprising a vanadium compound (a6) and/or a copper compound (a7).

6. The curable composition (A) according to claim 1, wherein the cyclic thiourea compound (a3) is at least one selected from the group consisting of 4-methyl-2-imidazolidinethione, 4,4-dimethyl-2-imidazolidinethione, 4-ethyl-2-imidazolidinethione, and 4,4-diethyl-2-imidazolidinethione.

7. A dental method, comprising:

applying the curable composition (A) according to claim 1 to a tooth structure.

8. An adhesive kit comprising:

a pretreatment agent (B) comprising an acidic group-containing radical polymerizable monomer (b1), a polymerization accelerator (b2), a solvent (b3), and a hydrophilic radical polymerizable monomer (b4) having no acidic group; and

the curable composition (A) according to claim 1.

9. The adhesive kit according to claim 8, wherein the polymerization accelerator (b2) is a vanadium compound (b2-1) and/or a copper compound (b2-2).

10. A dental method, comprising:

applying the pretreatment agent (B) and the curable composition (A) of the adhesive kit according to claim 8 to a tooth structure.

11. The curable composition (A) according to claim 1,

wherein the at least one cyclic thiourea compound (a3) comprises the substituted ethylenethiourea compound (a3-1) and

the substituted ethylenethiourea compound (a3-1) is 4,4-dimethyl-2-imidazolidinethione.

12. The curable composition (A) according to claim 1,

wherein the at least one cyclic thiourea compound (a3) comprises the substituted propylenethiourea compound (a3-2) and

the substituted propylenethiourea compound (a3-2) is 5,5-dimethyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione.

13. The curable composition (A) according to claim 1, wherein the at least one cyclic thiourea compound (a3) is selected from the group consisting of the substituted propylenethiourea compound (a3-2) and the substituted butylenethiourea compound (a3-3).