Dental materials based on redox systems with low-odour cumene hydroperoxide derivatives

Patent metadata

Field	Value
Publication number	US-11357709-B2
Application number	US-202016778034-A
Country	US
Kind code	B2
Filing date	Jan 31, 2020
Priority date	Feb 7, 2019
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

Radically polymerizable dental material, which contains a combination of a thiourea derivative and a hydroperoxide according to the following Formula (I) as initiator system for the radical polymerization:

First claim

The invention claimed is:

1. Radically polymerizable dental material comprising
a combination of a thiourea derivative and a hydroperoxide as an initiator system for the radical polymerization, characterized in that it contains a hydroperoxide according to the following Formula (I),

in which the variables have the following meanings:
Q 1 an n-valent, aromatic, aliphatic, linear or branched C 1 -C 14 hydrocarbon radical, which can be interrupted by one or more S and/or O atoms and which can be unsubstituted or substituted by one or more substituents,
X, Y independently of each other are in each case absent, —O—, —COO—; —CONR 2 —, or —O—CO—NR 3 —, wherein R 2 and R 3 independently of each other represent H or a C 1 -C 5 alkyl radical,
Q 2 is absent with, an aliphatic, linear or branched C 1 -C 14 alkylene radical, which can be interrupted by S and/or O atoms and which can be unsubstituted or substituted by —OH, —OR 4 , —Cl and/or —Br, wherein R 4 is an aliphatic, linear or branched C 1 -C 10 hydrocarbon radical,
Q 3 a C 1 -C 3 alkylene group or is absent,
wherein X and/or Y is absent if Q 2 is absent,
n 1, 2, 3 or 4, and wherein
the substitution on the aromatic compound takes place in position 2, 3 or 4.

2. Dental material according to claim 1 , in which the variables have the following meanings:
Q 1 an n-valent, aromatic, aliphatic, linear or branched C 1 -C 14 hydrocarbon radical, which can be interrupted by one or more S and/or O atoms and which can be unsubstituted or substituted by one or more substituents which are selected from —OH, —OR 1 , —Cl and —Br, wherein R 1 is an aliphatic, linear or branched C 1 -C 10 hydrocarbon radical,
X, Y independently of each other are in each case absent, —O—, —COO—; —CONR 2 —, or —O—CO—NR 3 —, wherein R 2 and R 3 independently of each other represent H, methyl and/or ethyl, and wherein X and Y are not absent at the same time,
Q 2 is absent with, an aliphatic, linear or branched C 1 -C 14 alkylene radical, which can be interrupted by S and/or O atoms and which can be unsubstituted or substituted by —OH, —OR 4 , —Cl and/or —Br, wherein R 4 is an aliphatic, linear or branched C 1 -C 10 hydrocarbon radical,
Q 3 -CH 2 — or is absent
wherein X and/or Y is absent if Q 2 is absent,

n 1, 2, 3 or 4, and wherein
the substitution on the aromatic compound takes place in position 2, 3 or 4.

3. Dental material according to claim 1 , in which the variables have the following meanings:
Q 1 a mono- or divalent, aliphatic, linear or branched C 1 -C 10 hydrocarbon radical, which can be interrupted by one or more O atoms, and which can be substituted by one or more substituents which are selected from —OH and —OR 1 , or is unsubstituted, wherein R 1 is an aliphatic, linear or branched C 1 -C 6 hydrocarbon radical,
X, Y independently of each other are in each case absent, —O—, —COO— or —O—CO—NR 3 —, wherein R 3 represents H or a C 1 -C 5 alkyl radical,
Q 2 is absent with, a linear or branched C 1 -C 10 alkylene radical, which can be interrupted by one or more O atoms, and which can be substituted by one or more substituents which are selected from —OH and —OR 4 , or is unsubstituted, wherein R 4 is an aliphatic, linear or branched C 1 -C 6 hydrocarbon radical,
n 1 or 2, and wherein
the substitution on the aromatic compound takes place in position 3 or in position 4.

4. Dental material according to claim 1 , in which the variables have the following meanings:
Q 1 a mono- or divalent, aliphatic, linear or branched C 1 -C 10 hydrocarbon radical, which can be interrupted by one O atom, and which can be substituted by one substituent which is selected from —OH and —OR 1 , or is unsubstituted, wherein R 1 is an aliphatic, linear or branched C 1 -C 6 hydrocarbon radical,
X, Y independently of each other are in each case absent, —O—, —COO— or —O—CO—NR 3 —, wherein R 3 represents H, methyl and/or ethyl and wherein X and Y are not absent at the same time,
Q 2 is absent with, a linear or branched C 1 -C 10 alkylene radical, which can be interrupted by one O atom, and which can be substituted by one substituent which is selected from —OH and —OR 4 , or is unsubstituted, wherein R 4 is an aliphatic, linear or branched C 1 -C 6 hydrocarbon radical,
n 1 or 2, and wherein
the substitution on the aromatic compound takes place in in position 4.

5. Dental material according to claim 3 , in which the variables have the following meanings:
Q 1 a mono- or divalent, aliphatic, linear or branched C 1 -C 5 hydrocarbon radical, which can be interrupted by one O atom and which can be substituted by one OH group,
X —COO—,
Y is absent
Q 2 is absent or a linear C 1 -C 3 alkylene radical,
n 1 or 2, and wherein
the substitution on the aromatic compound takes place in position 4.

6. Dental material according to claim 5 , in which the variables have the following meanings:
Q 1 a mono- or divalent, aliphatic, branched, or linear C 1 -C 4 hydrocarbon radical,
X —COO—,
Y is absent
Q 2 is absent or a methylene radical,
n 1 or 2, and wherein
the substitution on the aromatic compound takes place in position 4.

7. Dental material according to claim 1 , comprising acetyl, allyl, pyridyl, phenyl thiourea, hexanoyl thiourea, or a mixture thereof, as thiourea derivative.

8. Dental material according to claim 1 , which additionally comprises a peroxide.

9. Dental material according to claim 8 , wherein the peroxide comprises α,α-bis(t-butylperoxy)diisopropylbenzene, dicumene peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butyl cumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3 or a mixture thereof, a diacyl peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearyl peroxide, succinic acid peroxide, m-toluoyl benzoyl peroxide, benzoyl peroxide (DBPO) or a mixture thereof.

10. Dental material according to claim 1 , which additionally comprises a transition metal compound.

11. Dental material according to claim 10 , wherein the transition metal compound comprises a compound of a transition metal which has at least two stable oxidation states, or a compound of copper, iron, cobalt, nickel, manganese or a mixture thereof.

12. Dental material according to claim 1 comprising
0.01 to 10 wt.-% hydroperoxide, relative to the total mass of the material,
25 to 100 mol-% of thiourea derivative, relative to the molar quantity of hydroperoxide,
optionally 1 to 15 wt.-% peroxide, relative to the mass of the hydroperoxide, and
optionally 0.0001 to 1 wt.-% transition metal compound, relative to the total mass of the composition.

13. Dental material according to claim 1 comprising
0.05 to 8.0 wt.-% hydroperoxide, relative to the total mass of the material,
50 to 100 mol-% thiourea derivative, relative to the molar quantity of hydroperoxide,
optionally 1 to 10 wt.-% peroxide, relative to the mass of the hydroperoxide, and
optionally 0.0005 to 0.5 wt.-% transition metal compound, relative to the total mass of the composition.

14. Dental material according to claim 1 comprising
0.1 to 5.0 wt.-% hydroperoxide, relative to the total mass of the material,
an equimolar quantity of thiourea derivative, relative to the molar quantity of hydroperoxide,
optionally 2 to 8 wt.-% peroxide, relative to the mass of the hydroperoxide, and
optionally 0.0007 to 0.020 wt.-% transition metal com

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Köhler Thomas
• Schädlich Johannes
• Angermann Jörg

Classifications

• C08F4/40

  Redox systems · CPC title

• A61K6/887 Primary

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

• A61K6/71

  Fillers · CPC title

• C07C409/12

  with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring · CPC title

• A61K6/17 Primary

  Particle size · CPC title