One-part dental adhesive composition for fixing dental composite materials

1. A one-part dental adhesive composition comprising:

polymerizable component(s) with an acidic moiety as Component A;

photo-initiator(s) as Component B1;

transition metal ion component(s) as Component C, the transition metal ion component(s) present in a total amount of 0.001 wt % to 1 wt %;

water as Component D2;

a stabilizer as Component E, the stabilizer comprising a free radical moiety;

optionally, a stabilizer selected from butylated hydroxy toluene, monomethyl ether hydroquinone, or a combination thereof, present in an amount of less than 0.01 wt % with respect to the weight of the one-part dental adhesive composition.

2. A method for fixing a dental composite material to a surface of hard dental tissue, the method comprising the steps of:

applying a one-part dental adhesive composition of claim 1 to the surface of hard dental tissue,

optionally applying radiation to the one-part dental adhesive composition,

applying the dental composite material to the surface of hard dental tissue which has been treated with the one-part dental adhesive composition.

3. The one-part dental adhesive composition according to claim 1 ,

the transition metal ion component(s) comprising metal ions selected from copper, iron or vanadium and mixtures thereof,

and being present in an amount of 0.01 to 1 wt. % with respect to the weight of the dental adhesive composition.

4. The one-part dental adhesive composition according to claim 1 ,

the photo-initiator(s) being selected from components comprising an alpha-alpha diketone moiety, an anthraquinone moiety, a thioxanthone moiety or benzoin moiety,

and being present in an amount of 0.5 to 3 wt. % with respect to the weight of the dental adhesive composition.

5. The one-part dental adhesive composition according to claim 1 , the stabilizer comprising a free radical moiety selected from 2,2-diphenyl-1-picrylhydrazyl, 4-hydroxy-2,2,6,6-tetramethyl-piperidine 1-oxyl, 2,2,6,6 tetramethyl-piperidinyloxyl, 2,6-di-tert-butyl-a-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl, and triphenylmethyl radical.

6. The one-part dental adhesive composition according to claim 1 , comprising in addition the following components alone or in combination:

reducing agent(s) as Component B2;

solvent(s) other than water as Component D1;

filler(s) as Component F;

polymerizable component(s) without an acidic moiety as Component G;

functionalized organosilane(s) as Component H;

additive(s) as Component I.

7. The one-part dental adhesive composition according to claim 1 , comprising in addition the following components alone or in combination:

reducing agent(s) as Component B2 in an amount of 0.1 to 2 wt. %;

solvent(s) other than water as Component D1 in an amount of 5 to 40 wt. %,

water as Component D2 in an amount of 1 to 20 wt. %;

filler(s) as Component F in an amount of 0.5 to 10 wt. %;

polymerizable component(s) without an acidic moiety as Component G in an amount of 5 to 60 wt. %;

functionalized organosilane(s) as Component H in an amount of 1 to 10 wt. %;

additive(s) as Component I in an amount of 0 to 5 wt. %;

wt. % with respect to the weight of the dental adhesive composition.

8. The dental adhesive composition according to claim 1 , comprising:

polymerizable component(s) with an acidic moiety in an amount of 3 to 20 wt. %,

photo-initiator(s) comprising an alpha-alpha diketone moiety in an amount of 0.5 to 3 wt. %,

transition metal ion component(s) selected from components comprising copper, iron or vanadium ions, in an amount of 0.01 to 1 wt. %,

solvent other than water in an amount of 5 to 40 wt. %,

water in an amount of 5 to 20 wt. %,

stabilizer(s) comprising a free radical moiety in an amount of 0.01 to 0.5 wt. %,

reducing agent(s) in an amount of 0.1 to 3 wt. %,

filler(s) comprising silica in an amount of 0.5 to 10 wt. %,

polymerizable component(s) without an acidic moiety in an amount of 5 to 60 wt. %,

functionalized silane comprising a (meth)acrylate moiety in an amount of 1 to 10 wt. %,

functionalized silane comprising an amino moiety in an amount of 1 to 10 wt. %,

additive(s) in an amount of 0 to 5 wt. %,

wt. % with respect to the weight of the dental adhesive composition.

9. The one-part dental adhesive composition according to claim 1 , not comprising the following components alone or in combination:

organic boron containing component(s) in an amount of more than 0.2 wt. %;

sulfinic acid component(s) in an amount of more than 0.2 wt. %;

persulfate component(s) in an amount of more than 0.2 wt. %;

thiourea component(s) in an amount of more than 0.2 wt. %;

cysteine component(s) in an amount of more than 0.2 wt. %,

wt. % with respect to the weight of the dental adhesive composition.

10. The one-part dental adhesive composition according to claim 1 , being a self-etching, self-adhesive dental composition.

11. The one-part dental adhesive composition of claim 10 , being characterized by the following features alone or in combination:

viscosity: 0.01 to 3 Pats at 23° C. and a shear rate of 100 s-1;

pH-value: 0.8 to 4;

shear bond strength to dentin: at least 9 MPa;

being storage stable.

12. A kit of parts comprising:

a one-part dental adhesive composition of claim 1 , and

a dental composite material comprising:

polymerizable component(s) without an acidic moiety,

filler(s), and

a redox-initiator system comprising an oxidizing agent and a reducing agent.

13. The kit of parts according to claim 12 , the dental composite material being provided as a kit of parts comprising a base part and a catalyst part, wherein the oxidizing agent and the reducing agent are contained in different parts during storage.

14. The kit of parts according to claim 12 , the dental composite material comprising in addition a photo-initiator system.

15. The kit of parts according to claim 12 , comprising in addition the following parts alone or in combination:

dental filling composite;

dental sealant;

dental cement;

dental core build-up material;

dental milling blank;

hydrofluoric acid etchant;

instruction for use.

16. The one-part dental adhesive composition of claim 1 , the transition metal component(s) selected from components comprising vanadium, chromium, manganese, iron, cobalt, nickel, copper, and a combination thereof.

17. The one-part dental adhesive composition of claim 1 , the transition metal component(s) selected from copper acetate and vanadyl acetylacetonate.

18. The one-part dental adhesive composition of claim 1 ,

the stabilizer having a free-radical moiety selected from 2,2-diphenyl-1-picrylhydrazyl and 2,2,6,6 tetramethyl-piperidinyloxyl; and

the transition metal component(s) selected from copper acetate and vanadyl acetylacetonate.