Dental Materials With Improved Setting Behaviour

Patent metadata

Field	Value
Publication number	US-2020253838-A1
Application number	US-202016778777-A
Country	US
Kind code	A1
Filing date	Jan 31, 2020
Priority date	Feb 7, 2019
Publication date	Aug 13, 2020
Grant date	—

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

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 contains at least one peroxide.

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 acetyl, allyl, pyridyl, 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) (SR-348c), 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 and/or 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 and/or 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 and/or 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 contains 50 to 85 wt.-% or 10 to 70 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.

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

• C08F4/40

  Redox systems · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/887 Primary

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