Dental materials with improved setting behaviour

Patent metadata

Field	Value
Publication number	US-11141356-B2
Application number	US-202016778777-A
Country	US
Kind code	B2
Filing date	Jan 31, 2020
Priority date	Feb 7, 2019
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

Radically polymerizable dental material, which contains a combination of a thiourea derivative, a hydroperoxide and at least one peroxide 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 initiator system for the radical polymerization, characterized in that it additionally comprises at least one peroxide in a quantity of from 1 to 15 wt.-% relative to the mass of the hydroperoxide and which does not comprise amines.

2. Dental material according to claim 1 , comprising a compound of the formula R—(OOH) n , in which R is an aliphatic or aromatic hydrocarbon radical and n is 1 or 2, as hydroperoxide.

3. Dental material according to claim 2 , comprising t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, t-hexyl peroxide, 2,5-dimethyl-2,5-di(hydroperoxy)hexane, diisopropylbenzene monohydroperoxide, paramenthane hydroperoxide, p-isopropylcumene hydroperoxide, cumene hydroperoxide (CHP), or a mixture thereof, as hydroperoxide.

4. Dental material according to claim 1 , comprising 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 as peroxide.

5. Dental material according to claim 1 , comprising a diacyl peroxide as peroxide.

6. Dental material according to claim 5 , wherein the diacyl peroxide comprises 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.

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

8. Dental material according to claim 1 , comprising
0.01 to 5.0 wt.-%, hydroperoxide, relative to the total mass of the material,
25 to 100 mol-% thiourea derivative, relative to the molar quantity of hydroperoxide,
1 to 15 wt.-% peroxide, relative to the mass of the hydroperoxide.

9. Dental material according to claim 1 , comprising
0.05 to 4.0 wt.-% hydroperoxide, relative to the total mass of the material,
50 to 100 mol-% thiourea derivative, relative to the molar quantity of hydroperoxide,
1 to 10 wt.-% peroxide, relative to the mass of the hydroperoxide.

10. Dental material according to claim 1 , comprising
0.1 to 3.0 wt.-% hydroperoxide, relative to the total mass of the material,
an equimolar quantity of thiourea derivative, relative to the molar quantity of hydroperoxide,
2 to 8 wt.-% peroxide, relative to the mass of the hydroperoxide.

11. Dental material according to claim 1 , which additionally comprises at least one radically polymerizable monomer.

12. Dental material according to claim 11 , wherein the at least one radically polymerizable monomer comprises at least one mono- or multifunctional (meth)acrylate, at least one dimethacrylate or a mixture of mono- and dimethacrylates.

13. Dental material according to claim 11 , comprising methyl, ethyl, 2-hydroxyethyl, butyl, benzyl, tetrahydrofurfuryl or isobornyl (meth)acrylate, p-cumylphenoxyethylene glycol methacrylate (CMP-1E), 2-(2-biphenyloxy)ethyl methacrylate, bisphenol A dimethacrylate, bis-GMA (an addition product of methacrylic acid and bisphenol A diglycidyl ether), ethoxylated or propoxylated bisphenol A dimethacrylate, 2-[4-(2-methacryloyloxyethoxyethoxy)phenyl]-2-[4-(2-methacryloyloxyethoxy)phenyl]propane), 2,2-bis[4-(2-methacryloxypropoxy)phenyl]propane, UDMA (an addition product of 2-hydroxyethyl methacrylate and 2,2,4-trimethylhexamethylene-1,6-diisocyanate), V-380 (an addition product of a mixture of 0.7 mol 2-hydroxyethyl methacrylate and 0.3 mol 2-hydroxypropyl methacrylate with 1 mol α,α,α′,α′-tetramethyl-m-xylylene diisocyanate), di-, tri- or tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, glycerol di- and trimethacrylate, 1,4-butanediol dimethacrylate, 1,10-decanediol dimethacrylate (D 3 MA), bis(methacryloyloxymethyl)tricyclo-[5.2.1.02,6]decane (DCP), a polyethylene glycol or polypropylene glycol dimethacrylate, polyethylene glycol 200 dimethacrylate, polyethylene glycol 400 dimethacrylate (PEG 200 DMA or PEG 400 DMA), 1,12-dodecanediol dimethacrylate or a mixture thereof as radically polymerizable monomer.

14. Dental material according to claim 11 , which additionally comprises at least one acid-group-containing radically polymerizable monomer.

15. Dental material according to claim 14 , wherein the at least one acid-group-containing radically polymerizable monomer comprises a polymerizable carboxylic acid, phosphonic acid, a polymerizable phosphoric acid ester or an anhydride of these substances.

16. Dental material according to claim 1 , which additionally comprises at least one organic or inorganic filler.

17. Dental material according to claim 16 , wherein the at least one organic or inorganic filler comprises an oxide comprising one of SiO 2 , ZrO 2 and TiO 2 or a mixed oxide of SiO 2 , ZrO 2 , ZnO and/or TiO 2 , a nanoparticulate or microfine filler comprising pyrogenic silica or precipitated silica, glass powders comprising quartz, glass ceramic or radiopaque glass powder comprising barium or strontium aluminium silicate glass powder, a radiopaque filler comprising ytterbium trifluoride, tantalum(V) oxide, barium sulfate, a mixed oxide of SiO 2 with ytterbium(III) oxide or tantalum(V) oxide, a ground prepolymer or a pearl polymer.

18. Dental material according to claim 1 , comprising
(a) 0.01 to 5.0 wt.-% hydroperoxide,
(b) 0.001 to 3.0 wt.-% peroxide,
(c) 0.001 to 5.0 wt.-% thiourea derivative,
(d) 5 to 95 wt.-% radically polymerizable monomer,
(e) 0 to 85 wt.-% filler, and
(f) 0.01 to 5 wt.-% additive,
in each case relative to the total mass of the material.

19. Dental material according to claim 1 , comprising
(a) 0.05 to 4.0 wt.-% hydroperoxide,
(b) 0.005 to 2.0 wt.-% peroxide,
(c) 0.003 to 4.0 wt.-% thiourea derivative,
(d) 10 to 95 wt.-% radically polymerizable monomer,
(e) 0 to 85 wt.-% filler, and
(f) 0.1 to 3 wt.-% additive,
in each case relative to the total mass of the material.

20. Dental material according claim 1 , comprising
(a) 0.1 to 3.0 wt.-% hydroperoxide,
(b) 0.50 wt.-% peroxide,
(c) 0.005 to 3.0 wt.-% thiourea derivative,
(d) 10 to 90 wt.-% radically polymerizable monomer,
(e) 0 to 85 wt.-% filler, and
(f) 0.1 to 2 wt.-% additive,
in each case relative to the total mass of the material.

21. Dental material according to claim 18 , which comprises 50 to 85 wt.-% filler.

22. Dental material according to claim 1 for therapeutic application as dental cement, filling composite or veneering material.

23. Dental material according to claim 1 for non-therapeutic use for the production or repair of dental restorations comprising prostheses, artificial teeth, inlays, onlays, crowns, bridges and complete dentures.

24. Dental material according to claim 18 , which comprises 10 to 70 wt.-% filler.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Gianasmidis Alexandros
• Westphal Michael
• Brot Andy
• Grabenbauer Barbara

Classifications

• A61K6/61 Primary

  Cationic, anionic or redox initiators · CPC title

• A61K6/887 Primary

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

• C08F4/40

  Redox systems · CPC title

• A61K6/71

  Fillers · CPC title