Photochromic dental material with encapsulated photochromic colorants

Patent metadata

Field	Value
Publication number	US-10980712-B2
Application number	US-201916251157-A
Country	US
Kind code	B2
Filing date	Jan 18, 2019
Priority date	Jan 23, 2018
Publication date	Apr 20, 2021
Grant date	Apr 20, 2021

Abstract

Radically polymerizable dental material, which contains at least one encapsulated photochromic colorant.

First claim

The invention claimed is:

1. Radically polymerizable dental material comprising
at least one photochromic colorant,
wherein the colorant is encased in a polymer capsule, the polymer capsule comprising an outer capsule wall and an inner core,
wherein the outer capsule wall is formed of an organic polymer and the inner core comprises a liquid.

2. Dental material according to claim 1 ,
wherein the outer capsule wall is formed of an organic polymer comprising melamine-formaldehyde resin, polyester, polyamide, polyurethane, polysaccharide and/or urea-formaldehyde resin.

3. Dental material according to claim 2 ,
wherein the outer capsule wall is formed of the melamine-formaldehyde resin based on N-(4,6-diamino-1,3,5-triazin-2-yl)formamide (CAS No. 13236-84-5).

4. Dental material according to claim 1 ,
wherein the photochromic colorant can be activated to a color change by light with a wavelength of from 350 to 800 nm.

5. Dental material according to claim 1 ,
wherein the photochromic colorant can be activated to a color change by light with a wavelength of from 370 to 490 nm.

6. Dental material according to claim 1 ,
wherein the photochromic colorant is a photochromic organic dye, which is selected from spirooxazines, spiropyrans, azobenzene compounds, stilbenes, pentadienyl anions and combinations thereof.

7. Dental material according to claim 6 ,
wherein the photochromic organic dye is a spirooxazine comprising a spirooxazine with the parent substance 1,3,3-trimethyl-spiro[indoline-2,3′-[3H]naphtho[2,1-b][1,4]oxazine (NISO) or comprising 6′-piperidine-1,3,3,-trimethyl-spiro[indoline-2,3′-[3H]naphtho[2,1-b][1,4]oxazine].

8. Dental material according to claim 1 ,
wherein the liquid of the inner core comprises organic solvents, carboxylic acid esters, glycerol esters and mixtures thereof.

9. Dental material according to claim 1 ,
wherein the liquid of the inner core comprises Miglyol, trioctanoin and/or methyl stearate.

10. Dental material according to claim 1 ,
further comprising one or more of a radically polymerizable monomer, an initiator for radical polymerization, and a particulate filler.

11. Dental material according to claim 10 ,
wherein the radically polymerizable monomer comprises a mono- or polyfunctional (meth)acrylic acid derivative and the initiator comprises a photoinitiator.

12. Dental material according to claim 10 ,
wherein the radically polymerizable monomer comprises at least one mono- and/or polyfunctional (meth)acrylic acid derivative, at least one non-acidic ester of phosphoric acid with a hydroxy methacrylate or a mixture thereof.

13. Dental material according to claim 1 , comprising
a) 0.0001 to 5 wt.-% of at least one encapsulated photochromic colorant,
b) 0.01 to 10 wt.-% of at least one initiator,
c) optionally 5 to 85 wt.-% of at least one monomer,
d) optionally 2.5 to 80 wt.-% filler(s) and
e) optionally 2.5 to 70 wt.-% solvent,
in each case relative to the total mass of the dental material.

14. Dental material according to claim 1 , comprising
a) 0.001 to 3.0 wt.-% of at least one encapsulated photochromic colorant,
b) 0.1 to 3.0 wt.-% of at least one initiator,
c) optionally 10 to 60 wt.-% of at least one monomer,
d) optionally 2.5 to 80 wt.-% filler(s) and
e) optionally 2.5 to 70 wt.-% solvent,
in each case relative to the total mass of the dental material.

15. Dental material according to claim 1 , comprising
a) 0.1 to 1.0 wt.-% of at least one encapsulated photochromic colorant,
b) 0.1 to 3.0 wt.-% of at least one initiator,
c) optionally 15 to 50 wt.-% of at least one monomer,
d) optionally 2.5 to 80 wt.-% filler(s), and
e) optionally 2.5 to 70 wt.-% solvent,
in each case relative to the total mass of the dental material.

16. Dental material according to claim 11 for use as a fissure sealant.

17. Method of producing a photochromic dental material using an encapsulated photochromic colorant comprising at least one photochromic colorant, wherein the colorant is encased in a polymer capsule, the polymer capsule comprising an outer capsule wall and an inner core, wherein the outer capsule wall is formed of an organic polymer and the inner core comprises a liquid, said method comprising
mixing the photochromic colorant with one or more of a radically polymerizable monomer, an initiator for radical polymerization, and a particulate filler.

18. Method of using a dental material comprising at least one photochromic colorant, wherein the colorant is encased in a polymer capsule, the polymer capsule comprising an outer capsule wall and an inner core, wherein the outer capsule wall is formed of an organic polymer and the inner core comprises a liquid, said method comprising
using the dental material for extraoral production of a dental restoration or repair of a dental restoration,
wherein the dental restoration is cured and a conclusive assessment of coloration of the dental restoration is made.

19. Method according to claim 18 ,
wherein the dental restoration comprises one or more of prostheses, artificial teeth, inlays, onlays, crowns and bridges.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Bock Thorsten
• Hauner-Westphal Martina

Classifications

• A61K6/66 Primary

  Photochromic dyes · 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

• A61K6/78

  Pigments · CPC title

• A61K6/887

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