Acid-Stable Glass Fillers And Self-Adhesive Dental Composite Cements With Good Transparency Containing Them

Patent metadata

Field	Value
Publication number	US-2025017827-A1
Application number	US-202418761692-A
Country	US
Kind code	A1
Filing date	Jul 2, 2024
Priority date	Jul 4, 2023
Publication date	Jan 16, 2025
Grant date	—

Abstract

Acid-stable glass fillers and self-adhesive dental composite cements with good transparency containing them. X-ray opaque glass filler with the following composition (wt. %): SiO 2 : 54.0-64.0; Al 2 O 3 : 10.0-25.0; B 2 O 3 : 0.0-10.0; La 2 O 3 : 0.1-10.0; WO 3 : 5.0-14.0; ZrO 2 : 0.1-7.0; MgO: 1.0-7.9; CaO: 0.1-6.0; ZnO: 0-6.0; SrO: 0-6.0, and radically polymerizable composition comprising, in addition to the radiopaque glass filler, at least one radically polymerizable monomer without an acid group, at least one radically polymerizable monomer containing an acid group, and at least one initiator for the radical polymerization. The glass filler is characterized by a high acid stability.

First claim

1 . An X-ray opaque glass filler, comprising in wt. %: SiO2: 54.0-64.0; Al2O3: 10.0-25.0; B2O3: 0.0-10.0; La2O3: 0.1-10.0; WO3: 5.0-14.0; ZrO2: 0.1-7.0; MgO: 1.0-7.9; CaO: 0.1-6.0; ZnO: 0-6.0; SrO: 0-6.0, with all percentages referring to the total mass of the glass and all components calculated as oxides.

2 . The glass filler of claim 1 , comprising in wt. %: SiO 2 : 55.0-63.0; Al 2 O 3 : 12.0-24.0; B 2 O 3 : 0.1-8.0; La 2 O 3 : 0.1-8.0; WO 3 : 5.0-13.0; ZrO 2 : 0.1-6.0; MgO: 2.0-7.5; CaO: 0.1-4.0; ZnO: 0-6.0; SrO: 0-6.0, with all percentages referring to the total mass of the glass and all components being calculated as oxides.

3 . The glass filler according to claim 1 , which does not contain alkali metal oxides.

4 . The glass filler according to claim 1 , which is not surface-treated.

5 . A radically polymerizable composition comprising at least one radically polymerizable monomer without an acid group, at least one radically polymerizable monomer containing an acid group, a glass filler and at least one initiator for the radical polymerization, characterized in that the composition comprises at least one glass filler according to claim 1 .

6 . The composition according to claim 5 , which comprises
a) 10 to 80 wt. % of the radiopaque glass filler, b) optionally 0.1 to 25 wt. % of one or more further fillers, c) 1 to 15 wt. % of at least one monomer containing acid groups, d) 5 to 40 wt. % of at least one polyfunctional monomer without acid groups, e) 0 to 10 wt. % of one or more oligomeric carboxylic acids, f) 1 to 20 wt. % of one or more monofunctional monomers without acid groups, g) 0.1 to 8 wt. % of an initiator for the radical polymerization, h) 0 to 20 wt. % water and i) 0.01 to 5 wt. % of one or more additives, in each case based on the total mass of the composition.

7 . The composition according to claim 5 , comprising as the radically polymerizable monomer at least one polyfunctional monomer selected from bisphenol A-dimethacrylate, bis-GMA (an addition product of methacrylic acid and bisphenol A diglycidyl ether), ethoxy- or propoxylated bis phenol-A-dimethacrylates, bisphenol-A-dimethacrylate with 3 ethoxy groups, 2,2-bis[4-(2-methacryloyloxypropoxy)phenyl]propane, UDMA (addition product of 2-hydroxyethyl methacrylate and 2,2,4-trimethylhexamethylene-1,6-diisocyanate), tetramethylxylylene diurethane ethylene glycol di(meth)acrylate, tetramethylxylylene diurethane-2-methylethylene glycol diurethane di(meth)acrylate (V-380), di-, tri- or tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, glycerol di- and glycerol trimethacrylate, 1,4-butanediol dimethacrylate, 1,10-decanediol dimethacrylate (D 3 MA), bis(methacryloyloxy methyl) tricyclo-[5.2.1.0 2,6 ]decane (DCP), polyethylene glycol or polypropylene glycol dimethacrylates, polyethylene glycol 200 dimethacrylate (PEG-200-DMA), polyethylene glycol 400 dimethacrylate (PEG-400-DMA), 1,12-dodecanediol dimethacrylate, urethanes of 2-(hydroxymethyl)acrylic acid and diisocyanates, 2,2,4-trimethylhexamethylene diisocyanate, isophorone diisocyanate, pyrrolidones, 1,6-bis(3-vinyl-2-pyrrolidonyl)hexane, bisacrylamides, methylene bisacrylamide, ethylene bisacrylamide, bis(meth)acrylamides, N,N′-diethyl-1,3-bis(acrylamido)propane, 1,3-bis(methacrylamido)propane, 1,4-bis(acrylamido)butane, 1,4-bis(acryloyl)piperazine and mixtures thereof.

8 . The composition according to claim 5 , which comprises as the acid group-containing monomer at least one monomer with a pKa value of 0.5 to 4.0 at room temperature.

9 . The composition according to claim 5 , comprising as the acid group containing monomer at least one monomer selected from monomers containing a phosphoric ester group or phosphonic acid group, 2-methacryloyloxyethylphenylhydrogen phosphate, 10-methacryloyloxydecyldihydro gene phosphate (MDP), glycerol dimethacrylate dihydrogen phosphate, dipentaerythritpentamethacryloyloxy phosphate, 4-vinyl benzyl phosphonic acid, 2-[4-(dihydroxyphosphoryl)-2-oxa-butyl]acrylic acid, 2-[4-(dihydroxyphosphoryl)-2-oxa-butyl]acrylic acid 2,4,6-trimethylphenyl ester, 4-(meth)acryloyloxyethyltrimellitic anhydride, 10-methacryloyloxydecyl malonic acid, N-(2-hydroxy-3-methacryloyloxypropyl)-N-phenylglycine, 4-vinylbenzoic acid or a mixture thereof.

10 . The composition according to claim 6 , which comprises as the one or more oligomeric carboxylic acids (e) polyacrylic acid having a number-average molar mass of less than 7200 g/mol.

11 . The composition according to claim 5 , comprising as the radically polymerizable monomer at least one monofunctional monomer selected from benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, p-cumylphenoxyethylene glycol methacrylate (CMP-1E), 2-([1,1′-biphenyl]-2-oxy)ethyl methacrylate (MA-836), tricyclodecanemethyl (meth)acrylate, 2-(2-biphenyloxy)ethyl (meth)acrylate, 2-hydroxyethyl (methacrylate), hydroxyethylpropyl (methacrylate), 2-acetoxyethyl methacrylate or a mixture thereof.

12 . The composition according to claim 5 , comprising a catalyst paste and a base paste, wherein the catalyst paste comprises
a) 10 to 80 wt. % of the radiopaque glass filler, b) optionally 0.1 to 25 wt. % of one or more further fillers, c) 2 to 30 wt. % of at least one monomer containing acid groups, d) 5 to 40 wt. % of at least one polyfunctional monomer without acid groups, e) 0 to 10 wt. % of one or more oligomeric carboxylic acids, f) 1 to 20 wt. % of one or more monofunctional monomers, g) 0.01 to 16 wt. % of at least one peroxide and/or hydroperoxide and optionally at least one photoinitiator, h) 0 to 20 wt. % water and i) 0.001 to 5 wt. % of one or more additives, in each case based on the total mass of the catalyst paste, and where the base paste comprises a) 10 to 80 wt. % of the radiopaque glass filler, b) optionally 0.1 to 25 wt. % of one or more further fillers, d) 5 to 40 wt. % of at least one polyfunctional monomer without acid groups, f) 1 to 20 wt. % of one or more monofunctional monomers without acid groups, g) 0.01 to 16 wt. % of at least one appropriate reducing agent and optionally at least one photoinitiator, h) 0 to 20 wt. % water and i) 0.001 to 5 wt. % of one or more additives, in each case based on the total mass of the base paste.

13 . The composition according to claim 5 for therapeutic use as a dental material.

14 . The composition according to claim 13 , wherein the dental material comprises a dental cement, coating material, veneering material, filling composite or luting cement.

15 . A process of manufacturing or repairing dental restorations comprising using the composition according to claim 5 to manufacture or repair dental restorations.

16 . The process according to claim 15 , wherein the dental restorations comprise inlays, onlays, crowns or bridges.

17 . A process of manufacturing a dental material comprising mixing the radiopaque glass according to claim 1 with other components to produce the dental material.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Ritzberger Christian
• Moszner Norbert
• Catel Yohann
• Dittmer Marc
• Gianasmidis Alexandros

Classifications

• A61C2201/005

  using radio-opaque means · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• A61K6/20

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title

• A61K6/77 Primary

  Glass · CPC title

• A61C5/73

  Composite crowns · CPC title