Storage-stable dental adhesive set for use with peroxidically and hydroperoxidically redox-initiated composites

Patent metadata

Field	Value
Publication number	US-12370129-B2
Application number	US-202217701034-A
Country	US
Kind code	B2
Filing date	Mar 22, 2022
Priority date	Mar 31, 2021
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

Dental adhesive set which contains an adhesive and an applicator which is coated with a vanadium(IV) salt.

First claim

The invention claimed is:

1. A dental adhesive set which comprises
an adhesive and
an applicator, which is coated with one or more vanadium (IV) salts but does not comprise an oxidizing agent and
a composite material that comprises a hydroperoxide or a peroxide as initiator for the radical polymerization.

2. The dental adhesive set according to claim 1 , in which the applicator is coated with vanadyl (IV) oxalate and/or vanadyl (IV) acetylacetonate and/or vanadyl (IV) picolinate.

3. The dental adhesive set according to claim 1 , in which the applicator is additionally coated with at least one sulfinic acid and/or sulfinic acid derivative.

4. The dental adhesive set according to claim 1 , in which the applicator is additionally coated with a reducing agent.

5. The dental adhesive set according to claim 1 , in which the adhesive comprises
(a) at least one radically polymerizable acidic monomer,
(b) at least one radically polymerizable monomer without acidic groups,
(c) at least one water-miscible organic solvent,
(d) water, and
(e) optionally one or more fillers, and
(f) optionally one or more stabilizers, and
(g) optionally a photoinitiator for the radical polymerization and
(h) optionally a thickener.

6. The dental adhesive set according to claim 5 , in which the adhesive comprises
(a) 1 to 40 wt.-% of at least one radically polymerizable acidic monomer,
(b) 1 to 80 wt.-% of at least one radically polymerizable monomer without acidic groups,
(c) up to 70 wt.-% of at least one water-miscible organic solvent,
(d) up to 70 wt.-% water, and
(e) optionally 0 to 20 wt.-% of at least one filler, and
(f) optionally 0.001-0.35 wt.-% of at least one stabilizer, and
(g) optionally 0.01 to 10 wt.-% photoinitiator, and
(h) optionally 0.1 to 8 wt.-% thickener,
in each case relative to the total mass of the composition.

7. The dental adhesive set according to claim 1 , in which the applicator is coated with vanadyl (IV) oxalate and the composite material comprises a hydroperoxide as initiator for the radical polymerization.

8. The dental adhesive set according to claim 1 , in which the adhesive and the applicator are stored spatially separated in a single-dose container, wherein a quantity of the adhesive is matched to a quantity of the one or more vanadium (IV) salts and optionally a sulfinic acid, a sulfinic acid derivative, an ascorbic acid and/or an ascorbic acid derivative on the coated applicator such that, after being mixed with the applicator, the adhesive contains a quantity of the one or more vanadium (IV) salts and optionally a sulfinic acid, a sulfinic acid derivative, an ascorbic acid and/or an ascorbic acid derivative for performing radical curing.

9. The dental adhesive set according to claim 1 , in which the applicator and the adhesive are stored spatially separated from each other in a multi-dose container, wherein a quantity of the one or more vanadium (IV) salts and optionally a sulfinic acid derivative on the coated applicator is measured such that, after a predefined quantity of the adhesive has been mixed with the applicator, the adhesive contains a quantity of the one or more vanadium (IV) salts and optionally the sulfinic acid derivative for performing radical curing.

10. The dental adhesive set according to claim 1 for therapeutic use in intraoral restoration of damaged teeth.

11. The dental adhesive set according to claim 3 , in which the at least one sulfinic acid and/or sulfinic acid derivative comprises a sulfinic acid ester and/or sulfinic acid salt.

12. The dental adhesive set according to claim 4 , in which the reducing agent comprises ascorbic acid or an ascorbic acid derivative.

13. The dental adhesive set according to claim 5 , in which the adhesive comprises
(a) 2 to 30 wt.-% of at least one radically polymerizable acidic monomer,
(b) 1 to 60 wt.-% of at least one radically polymerizable monomer without acidic groups,
(c) 5 to 60 wt.-% of at least one water-miscible organic solvent,
(d) 5 to 60 wt.-% water, and
(e) optionally 0 to 20 wt.-% of at least one filler and
(f) optionally 0.03 to 0.30 wt.-% of at least one stabilizer, and
(g) optionally 0.1 to 4.5 wt.-% of a photoinitiator, and
(h) optionally 0.2 to 7 wt.-% thickener,
in each case relative to the total mass of the composition.

14. The dental adhesive set according to claim 5 , in which the adhesive comprises
(a) 5 to 20 wt.-% of at least one radically polymerizable acidic monomer,
(b) 5 to 55 wt.-% of at least one radically polymerizable monomer without acidic groups,
(c) 10 to 50 wt.-% of at least one water-miscible organic solvent,
(d) 8 to 50 wt.-% water, and
(e) optionally 0 to 20 wt.-% of one or more fillers, and
(f) optionally 0.05 to 0.25 wt.-% of at least one stabilizer, and
(g) optionally 0.5 to 4.0 wt.-% photoinitiator, and
(h) optionally 3 to 6 wt.-% thickener,
in each case relative to the total mass of the composition.

15. The dental adhesive set according to claim 11 , in which the at least one sulfinic acid and/or sulfinic acid derivative comprises sodium benzenesulfinate and/or lithium benzenesulfinate.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Bock Thorsten
• Köhler Thomas
• Barbisch Michael

Classifications

• A61K6/84

  comprising metals or alloys · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• A61K6/884

  comprising natural or synthetic resins · CPC title

• A61C19/00

  Dental auxiliary appliances (dental chairs or accessories therefor, working stands whether or not combined with chairs A61G15/00) · CPC title

• A61K6/60

  comprising organic or organo-metallic additives · CPC title