Hardenable dental composition containing a mixture of agglomerated and aggregated nano-particles, kit of parts and use thereof

Patent metadata

Field	Value
Publication number	US-9782329-B2
Application number	US-201414902948-A
Country	US
Kind code	B2
Filing date	Jul 1, 2014
Priority date	Jul 8, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The invention relates to a dental composition comprising filler (F1) comprising aggregated nano-sized particles in an amount of from about 30 to about 70 wt. %, filler (F2) comprising agglomerated nano-sized particles in an amount from about 1 to about 20 wt. %, hardenable component (A1) being an urethane(meth)acrylate with a functionality of at least 2 and having a molecular weight from about 400 to about 3,000 g/mol,-hardenable component (A2) being a radically polymerizable (meth)acrylate with a functionality of at least 2 being different from component (A1), redox curing initiator system, the dental composition not comprising non-agglomerated nano-sized filler in an amount above about 10 wt. %, wt. % with respect to the weight of the whole composition. The dental composition is in particular useful as or for production of permanent crown and bridges, inlays, onlays and veneers.

First claim

The invention claimed is:

1. Dental composition comprising:
filler (F1) comprising aggregated nano-sized particles in an amount of from about 30 to about 70 wt. %,
filler (F2) comprising agglomerated nano-sized particles in an amount from about 1 to about 20 wt. %,
hardenable component (A1) being an urethane(meth)acrylate with a functionality of at least 2 and having a molecular weight from about 400 to about 3,000 g/mol,
hardenable component (A2) being a radically polymerizable (meth)acrylate with functionality of at least 2 being different from component (A1),
redox curing initiator system,

the dental composition not comprising non-agglomerated nano-sized filler in an amount above about 10 wt. %, wt. % with respect to the weight of the whole composition;
the hardenable component (A1) being selected from:
compounds having the structure A-(-S1-U-S2-MA) n
A being a connector element comprising at least one unit,
S1 being a spacergroup comprising at least 4 units connected with each other,
S2 being a spacergroup comprising at least 4 units connected with each other,
U being a urethane connecting spacergroups S1 and S2,
MA being an acrylate or methacrylate group,
n being 3 to 6,
the units of A, S1 and S2 being independently selected from CH 3 —, —CH 2 —, —O—, —S—,
—NR 1 —, —CO—, —CR 1 ═,

—N═,
—CR 1 R 2 —,
with R 1 and R 2 independently selected from hydrogen, alkyl, substituted alkyl, alkenyl, cycloalkyl, substituted cycloalkyl, arylalkyl, aryl or substituted aryl, wherein these units can form linear, branched or cyclic structures,
and mixtures thereof.

2. Dental composition of claim 1 , wherein filler (F1) has at least one or all of the following features:
Specific surface: from about 50 to about 400 m 2 /g,
comprising particles selected from SiO 2 , ZrO 2 and mixtures thereof.

3. Dental composition of claim 1 , filler (F2) has at least one or all of the following features:
Specific surface: from about 30 to about 400 m 2 /g,
comprising particles selected from SiO 2 , ZrO 2 , Al 2 O 3 and mixtures thereof.

4. Dental composition of claim 1 , the hardenable component (A2) being selected from glycerol diacrylate, glycerol triacrylate, ethyleneglycol diacrylate, diethyleneglycol diacrylate, triethyleneglycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, trimethylolpropane triacrylate, 1,2,4-butanetriol trimethacrylate, 1,4-cyclohexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, sorbitol hexacrylate, bis[1-(2-acryloxy)]-p-ethoxyphenyl-dimethylmethane, bis[1-(3-acryloxy-2-hydroxy)]-p-propoxyphenyldimethylmethane, bis-acrylates and di(meth)acrylates of ethylene glycol, of polyethylene glycols and of polypropylene glycols of molecular weight 200-500, di(meth)acrylates of ethoxylated bisphenol A, 2,2′-bis(4-(meth)acryloxytetraethoxyphenyl)propanes, bis[3[4]-methacryl-oxymethyl -8(9)-tricyclo[5.2.1.0 2,6 ]decylmethyl triglycolate, 2,2-bis-4(3-methacryloxypropoxy)phenylpropane, di(meth)acrylates of bishydroxymethyltricyclo-(5.2.1.0 2,6 )decane and mixtures thereof.

5. The dental composition of claim 1 , the redox curing initiator system comprising components being selected from peroxide(s), components comprising a barbituric acid moiety, malonyl sulfamide(s) and mixtures thereof.

6. The dental composition of claim 1 , further comprising at least one of or all of the following components:
plasticiser,
x-ray visible particles,
pigments,
additives selected from retarder(s), anti-microbial(s), stabilizer(s), fluoride releasing material(s), absorber(s), emulsifier(s), antioxidant(s) and wetting agent(s), dye(s) and mixtures thereof.

7. The dental composition of claim 1 comprising a plasticiser selected from component(s) containing a polyethylene glycol moiety, polypropylene glycol(s), dibutyl-, dioctyl-, dinonyl- and diphenyl phthalate(s), ester(s) from adipinic, sebacinic and citric acid, paraffin oil(s), glycerol triacetate, ethoxylated and propoxylated Bisphenol A diacetate and silicone oil(s) and mixtures thereof.

8. The dental composition of claim 1 , wherein the dental composition has at least one or all of the following parameters:
working time: from about 30 sec to about 1.5 min,
setting time: from about 2.5 to about 6 min,
flexural strength after curing: from about 50 to about 200 MPa measured according to ISO 4049,
fracture work after curing: from about 5 to about 15 KJ/m 2 ,
impact strength after curing: from about 5 to 15 KJ/m 2 measured according to ISO 179-1,
abrasion after curing: less than about 20 mm 3 .

9. The dental composition of claim 1 not comprising at least one of or all of the following components:
polymerizable component comprising an acidic group in an amount above about 5 wt. %,
monofunctional (meth)acrylates in an amount above about 5 wt. %,
solvent in an amount above about 5 wt. %,
acid reactive filler in an amount above about 5 wt. %,
filler particles having a mean particle size from about 1 to about 100 μm in an amount above about 10 wt. %.

10. The dental composition of claim 1 , wherein:
amount of filler (F1): from about 30 to about 70 wt. %,
amount of filler (F2): from about 1 to about 20 wt. %,
amount of hardenable component (A1): from about 1 to about 20 wt. %,
amount of hardenable component (A2): from about 5 to about 60 wt. %, wt. % with respect to the weight of the whole composition.

11. The dental composition of claim 1 being provided as a kit of parts comprising a base part (A) and a catalyst part (B),
base part (A) comprising:
filler (F1) in an amount of from about 30 to about 70 wt. %,
filler (F2) in an amount from about 1 to about 20 wt. %,
hardenable component (A1),
hardenable component (A2),
dark curing initiator component(s) (X),

wt. % with respect to the weight of the base part,
catalyst part (B) comprising
filler (F2),
dark curing initiator component(s) (Y),

the dark curing initiator component(s) (X) and dark curing initiator component(s) (Y) forming a redox-initiator system.

12. The dental composition of claim 1 being provided as a kit of parts comprising a base part (A) and a catalyst part (B),
base part (A) comprising:
filler (F1) in an amount of from about 30 to about 70 wt. %,
filler (F2) in an amount from about 1 to about 20 wt. %,
hardenable component (A1) in an amount from about 1 to about 20 wt. %,
hardenable component (A2) in an amount from about 5 to about 60 wt. %,
dark curing initiator component(s) (X),

wt. % with respect to the weight of the base part,
a catalyst part (B) comprising:
filler (F1) in an amount of from about 30 to about 70 wt. %,
filler (F2) in an amount from about 1 to about 20 wt. %,
dark curing initiator component(s) (Y),

wt. % with respect to the weight of the catalyst part,
dark curing initiator component(s) (X) and dark curing initiator component(s) (Y) forming a redox-initiator system,
neither the base part (A) nor the catalyst part (B) comprising any of the following components:
polymerizable component comprising an acidic group above about 5 wt. %,
monofunctional (meth)acrylates above 5 wt. %,
solvent in an amount above about 5 wt. %,
acid reactive filler above about 5 wt. %,
filler particles having a mean particle size from about 1 to about 100 μm in an amount above about 10 wt. %,
non-agglomerated nano-sized fillers in an amount above about 10 wt. %.

13. A kit of parts of claim 11 fu

Assignees

• 3M Innovative Properties Co

Inventors

• Hecht Reinhold
• Hoheisel Uwe H
• Eckert Adrian S
• Hofmann Bernhard

Classifications

• A61K6/887 Primary

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

• A61K6/893

  Polyurethanes · CPC title

• A61K6/17 Primary

  Particle size · CPC title

• A61K6/71 Primary

  Fillers · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title