Chemical polymerization initiator, adhesive composition, adhesive composition kit, dental material, dental material kit, and method of storing adhesive composition

Patent metadata

Field	Value
Publication number	US-11325993-B2
Application number	US-201816756695-A
Country	US
Kind code	B2
Filing date	Dec 10, 2018
Priority date	Dec 26, 2017
Publication date	May 10, 2022
Grant date	May 10, 2022

Abstract

Provided are a chemical polymerization initiator including (a) a thiourea compound, (b) a peroxyester, (c) a divalent copper compound, and (d) an aryl borate compound, an adhesive composition, an adhesive composition kit, a dental material, and a dental material kit each using the chemical polymerization initiator, and a method of storing the adhesive composition.

First claim

The invention claimed is:

1. A chemical polymerization initiator, comprising:
(a) a thiourea compound;
(b) a peroxyester;
(c) a divalent copper compound; and
(d) an aryl borate compound.

2. The chemical polymerization initiator according to claim 1 , wherein (a) the thiourea compound is a compound represented by the following general formula (1):

in the formula (1), R 1 , R 2 , and R 3 each represent a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted acyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted alkenyl group, and R 2 may be bonded to any group selected from R 1 and R 3 to form a ring.

3. The chemical polymerization initiator according to claim 1 , wherein (b) the peroxyester is a peroxyester having a 10-hour half-life temperature of 80° C. or more.

4. The chemical polymerization initiator according to claim 1 ,
wherein (c) the divalent copper compound contains a divalent copper atom and a ligand coordinating to the divalent copper atom,
wherein the ligand is selected from the group consisting of a halogen atom, an atomic group containing an oxygen atom, and an atomic group containing a nitrogen atom,
wherein when the ligand is the atomic group containing the oxygen atom, the atomic group containing the oxygen atom coordinates to the divalent copper atom through the oxygen atom, and
wherein when the ligand is the atomic group containing the nitrogen atom, the atomic group containing the nitrogen atom coordinates to the divalent copper atom through the nitrogen atom.

5. An adhesive composition, comprising:
(a) a thiourea compound;
(b) a peroxyester;
(c) a divalent copper compound;
(d) an aryl borate compound; and
(e) an acidic group-containing polymerizable monomer.

6. The adhesive composition according to claim 5 , further comprising (f) an acidic group-free polymerizable monomer.

7. An adhesive composition kit, comprising a combination of a first partial composition and a second partial composition in a state of being incapable of physical contact with the first partial composition,
wherein an entirety of the combination of the first partial composition and the second partial composition contains at least five components formed of (a) a thiourea compound, (b) a peroxyester, (c) a divalent copper compound, (d) an aryl borate compound, and (e) an acidic group-containing polymerizable monomer,
wherein the first partial composition contains, as main components, (a) the thiourea compound and (d) the aryl borate compound out of the five components, and is substantially free of an organic peroxide, and
wherein the second partial composition contains, as main components, (b) the peroxyester, (c) the divalent copper compound, and (e) the acidic group-containing polymerizable monomer out of the five components, and is substantially free of a hydroperoxide.

8. The adhesive composition kit according to claim 7 , wherein at least one composition selected from the first partial composition and the second partial composition further contains (f) an acidic group-free polymerizable monomer.

9. The adhesive composition kit according to claim 7 , wherein at least one composition selected from the first partial composition and the second partial composition further contains at least one component selected from the group consisting of (g) a filler and (h) a solvent.

10. The adhesive composition kit according to claim 7 ,
wherein the first partial composition is formed only of (a) the thiourea compound, (d) the aryl borate compound, (f) an acidic group-free polymerizable monomer, and (g) a filler,
wherein the second partial composition is formed only of (b) the peroxyester, (c) the divalent copper compound, (e) the acidic group-containing polymerizable monomer, (f) an acidic group-free polymerizable monomer, and (g) a filler,
wherein (a) the thiourea compound is formed only of acetylthiourea,
wherein (b) the peroxyester is formed only of t-butyl peroxy-3,5,5-trimethylhexanoate,
wherein (c) the divalent copper compound is formed only of copper(II) acetate monohydrate, and
wherein (d) the aryl borate compound is formed only of a sodium salt of tetraphenylboric acid.

11. The adhesive composition kit according to claim 7 ,
wherein the first partial composition is formed only of (a) the thiourea compound, (d) the aryl borate compound, (f) an acidic group-free polymerizable monomer, and (g) a filler,
wherein the second partial composition is formed only of (b) the peroxyester, (c) the divalent copper compound, (e) the acidic group-containing polymerizable monomer, (f) an acidic group-free polymerizable monomer, and (g) a filler,
wherein (a) the thiourea compound is formed only of benzoylthiourea,
wherein (b) the peroxyester is formed only of t-butyl peroxy-3,5,5-trimethylhexanoate,
wherein (c) the divalent copper compound is formed only of copper(II) acetate monohydrate, and
wherein (d) the aryl borate compound is formed only of a sodium salt of tetraphenylboric acid.

12. A dental material, comprising the adhesive composition of claim 5 .

13. A dental material kit, comprising the adhesive composition kit of claim 7 .

14. A method of storing an adhesive composition, comprising storing the adhesive composition of claim 5 under a state in which the adhesive composition is packaged into a first partial composition and a second partial composition,
wherein the first partial composition contains, as main components, (a) the thiourea compound and (d) the aryl borate compound out of five components formed of (a) the thiourea compound, (b) the peroxyester, (c) the divalent copper compound, (d) the aryl borate compound, and (e) the acidic group-containing polymerizable monomer, and is substantially free of an organic peroxide, and
wherein the second partial composition contains, as main components, (b) the peroxyester, (c) the divalent copper compound, and (e) the acidic group-containing polymerizable monomer out of the five components, and is substantially free of a hydroperoxide.

Assignees

• Tokuyama Dental Corp

Inventors

• Fukudome Keishi

Classifications

• A61K6/00

  Preparations for dentistry · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C08F2/44 Primary

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title

• C08F4/34 Primary

  Per-compounds with one peroxy-radical · CPC title

• C08F4/50

  selected from alkaline earth metals, zinc, cadmium, mercury, copper or silver · CPC title