Dental composite material and mill blanks consisting of said composite material

Patent metadata

Field	Value
Publication number	US-11234904-B2
Application number	US-201816753469-A
Country	US
Kind code	B2
Filing date	Oct 1, 2018
Priority date	Oct 4, 2017
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

A polymerisable dental composite material comprising(i) 70 to 85% by weight of an inorganic filler component comprising at least one dental glass and optionally at least one amorphous metal oxide,(ii) 10 to 30% by weight of at least one monomer comprising 1,3-bis(5′-alkyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl and/or 1,3-bis(5′,9′-dialkyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl,(iii) 0.01 to 5% by weight of at least one di-, tri-, tetra- or multi-functional monomer not being a urethane (meth)acrylate,(iv) 0.01 to 10% by weight of at least one initiator, of an initiator system and optionally of at least one stabilizer and optionally of at least one pigment, wherein the total composition of the composite material amounts to 100% by weight, and a polymerized composite material having a flexural strength of greater than or equal to 190 MPa and an elastic modulus of 12 to 21 GPa for the production of indirect dentures.

First claim

The invention claimed is:

1. A polymerisable dental composite material, comprising
(i) 60 to 85% by weight of an inorganic filler component comprising at least one dental glass, as well as optionally at least one amorphous metal oxide,
(ii) 10 to 40% by weight of at least one monomer comprising 1,3-bis(5′-alkyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl and/or 1,3-bis(5′,9′-dialkyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl, wherein the alkyl groups, each independently, are selected from C1 to C4 alkyl groups,
(iii) 0.01 to 5% by weight of at least one di-, tri-, tetra- or multi-functional monomer not being a urethane (meth)acrylate, comprising bis(methacryloyloxymethyl)tetrahydrocyclopentadiene, bis(acryloyloxymethyl)tetrahydrodicyclopentadiene, as well as optionally mixtures comprising at least a 3,8-/3,9-/4,8-/ 3,10-/4,10 isomer and/or cis isomer and trans isomer of the aforementioned compounds, and optionally di-, tri-, tetra- or multi-functional (meth)acrylic esters of polyethers,
(iv) 0.01 to 10% by weight of at least one initiator, of an initiator system, as well as optionally of at least one stabilizer and optionally of at least one pigment, wherein the total composition of the composite material amounts to 100% by weight.

2. The dental composite material according to claim 1 , wherein
ii) the monomer comprises at least one monomer of general formula II,

with a) R 1 , R 4 equal to H and R 2 and R 3 each independently equal to C1 to C4 alkyl or b) R 1 , R 4 , R 2 and R 3 each independently equal to C1 to C4 alkyl.

3. The dental composite material according to claim 1 , wherein the dental glass has an average particle size d 50 of 0.1 to 1.0 μm.

4. The dental composite material according to claim 1 , wherein the amorphous metal oxide comprises at least one non-agglomerated amorphous metal oxide having a primary particle size of 2 to 45 nm, and the amorphous metal oxide optionally comprises precipitated silicon oxide, zirconium oxide or mixed oxides.

5. The dental composite material according to claim 1 , wherein the composite material comprises as (i) inorganic filler component
(i.1) 70 to 84% by weight of at least one dental glass, and optionally
(i.2) 1 to 15% by weight amorphous metal oxide, based on the total composition.

6. The dental composite material according to claim 1 , wherein (ii) further comprises a mixture of at least two different urethane (meth)acrylates, wherein the mixture comprises at least one difunctional urethane(meth)acrylate having a bivalent alicyclic group and a difunctional urethane (meth)acrylate having a bivalent alkylene group, and optionally at least one at least tetrafunctional dendritic urethane (meth)acrylate.

7. The dental composite material according to claim 1 , wherein the at least one stabilizer comprises water, at least one benzophenone derivative and/or at least one phenol derivative.

8. The dental composite material according to claim 1 , wherein
(ii) comprises 1,3-bis(5′-methyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl and/or 1,3-bis(5′,9′-dimethyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl, in a mixture with at least one other urethane (meth)acrylate, and/or
(iii) comprises bis(methacryloyloxymethyl)tetrahydrodicyclopentadiene, bis(acryloyloxymethyl)tetrahydrodicyclopentadiene, or a mixture of these monomers with at least one di-, tri-, tetra- or multi-functional monomer not being urethane (meth)acrylate.

9. A polymerized dental composite material obtained by polymerization of the composite material according to claim 1 .

10. The polymerized dental composite material according to claim 9 , having i) a flexural strength of greater than or equal to 200 MPa, dry after polymerization or 7 days, dry 23° C.+/−3° C., according to EN ISO 6872:2008, and/or
ii) having a flexural strength of greater than or equal to 200 MPa, 7 days, 37° C. H 2 O, according to EN ISO 6872:2008, and/or
iii) having a flexural strength of greater than or equal to 200 MPa, 7 days, 37° C. H 2 O, thermocycling 5000 cycles, according to EN ISO 6872:2008.

11. The polymerized dental composite material according to claim 9 , wherein i) the elastic modulus amounts to greater than or equal to 12 to 21 GPa dry after polymerization or 7 days, dry 23° C.+/−3° C., according to EN ISO 6872:2008, and/or
ii) the elastic modulus amounts to greater than or equal to 12 to 20 GPa, 7 days, 37° C. H 2 O, according to EN ISO 6872:2008, and/or
iii) the elastic modulus amounts to greater than or equal to 12 to 20 GPa, 7 days, 37° C. H 2 O, thermocycling 5000 cycles, according to EN ISO 6872:2008.

12. A polymerized dental composite material comprising
60 to 85% by weight of at least one inorganic filler compound comprising at least one dental glass of an average particle size d 50 of 0.1 to 1.0 μm, as well as optionally at least one amorphous silanised metal oxide of a primary particle size of 2 to 45 nm,
10 to 40% by weight of at least one polymer being based on at least one monomer comprising
(a) at least one monomer comprising 1,3-bis(5′-methyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl and/or 1,3-bis(5′,9′-dimethyl-3′,8′-dioxo-2′-aza-4′,7′-dioxa-decyl-9′-en)phenyl,
(b) bis(methacryloyloxymethyl)tetrahydrodicyc lopenta diene and/or bis(acryloyloxymethyl)tetrahydrodicyc lopenta diene, and
(c) optionally at least one di-urethane (meth)acrylate having a bivalent alkylene group,
(d) at least one tetra- to decafunctional dendritic urethane methacrylate, and
(e) optionally at least one di-, tri-, tetra- or multi-functional (meth)acrylic ester of polyethers, and
0.01 to 10% by weight of at least one pigment wherein the total composition of the composite material amounts to 100% by weight.

13. A polymerized dental composite material according to claim 9 , wherein the polymerized dental composite material is present in the form of a block of material, a block of material that is present as a three-dimensional geometrical moulded body, a block material as a milling blank without an adapter, or as a milling blank with an adapter for fastening in an automated device to remove material.

14. Method of using a dental composite material according to claim 1 for the production of dental prosthetic restorations in a material-removing process or for the production of direct adhesive dental restorations.

15. Method according to claim 14 for the production of dental prosthetic restorations comprising crowns, inlay, onlays, superstructures, artificial teeth, dental bridges, dental bars, spacers, abutments or veneers.

16. Polymerized dental composite material according to claim 9 obtained by polymerization at a pressure of 50 to 300 MPa and/or elevated temperature at 90 to 150° C.

17. The polymerised dental composite material according to claim 12 , wherein the polymerised dental composite material is present in the form of a block of material.

18. Method of using a dental composite material according to claim 9 for the production of dental prosthetic restorations in a material-removing process, or for the production of direct adhesive dental restorations.

19. Method of using dental composite material according to claim 12 for the production of dental prosthetic restorations in a material-removing process, or for the production of direct adhesive dental restorations.

Assignees

• Kulzer & Co Gmbh

Inventors

• Utterodt Andreas
• Reischl Kurt
• Schönhof Nelli
• Eck Michael
• Kocoglu Raif
• Schneider Jutta
• Kempka Caroline

Classifications

• A61K6/891 Primary

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

• A61K6/79 Primary

  Initiators · CPC title

• A61K6/78

  Pigments · CPC title

• A61K6/77

  Glass · CPC title

• A61K6/887

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