Dental composition and use thereof

Patent metadata

Field	Value
Publication number	US-10010488-B2
Application number	US-201515116873-A
Country	US
Kind code	B2
Filing date	Feb 10, 2015
Priority date	Feb 18, 2014
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

A dental composition comprising a polymerizable monomer (1), initiator, filler component(s) in an amount of more than about 20 wt.-%, wt.-% with respect to the whole weight of the composition, the polymerizable monomer (1) being characterized as follows: having exactly two (meth)acrylate reactive moieties, having an unsymmetrical backbone as linkage between the (meth)acrylate reactive moieties, the two (meth)acrylate reactive moieties being attached onto the unsymmetrical monomer backbone as alkyl esters, the unsymmetrical backbone comprising one aromatic moiety of the phenolic type, the polymerizable monomer (1) not containing an acidic moiety, other atoms than carbon, hydrogen, nitrogen, and oxygen, a bisphenol moiety. The invention is also directed to the use of the dental composition as or for producing a dental filling material, dental cement, crown and bridge material, inlay, onlay, veneer, orthodontic device or dental mill blank.

First claim

The invention claimed is:

1. A dental composition comprising:
polymerizable monomer (1);
initiator;
filler component(s) in an amount of more than about 20 wt.-%, with respect to the whole weight of the composition;
the polymerizable monomer (1) being characterized as follows:
having exactly two (meth)acrylate reactive moieties;
having an unsymmetrical backbone as linkage between the (meth)acrylate reactive moieties;
the two (meth)acrylate reactive moieties being attached onto the unsymmetrical monomer backbone as alkyl esters;
the unsymmetrical backbone comprising one aromatic moiety of the phenolic type;
having one or two urethane moieties within the unsymmetrical backbone;
the polymerizable monomer (1) not containing:
an acidic moiety;
other atoms than carbon, hydrogen, nitrogen, and oxygen;
a bisphenol moiety;
the polymerizable monomer (1) being characterized by formula (I)

with:
a=0 or 1,
A=

A being always attached as aryl-alkyl ether onto B and / or B′,
B=*—(CH 2 ) b —* , *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—* , *—(CH 2 —CH 2 —O—CH 2 —CH 2 —CH 2 )—* , *—(CH 2 —CH 2 —CH 2 —O—CH 2 —CH 2 —CH 2 )—*,

B being attached as alkyl ester onto the (meth)acrylate reactive group or as urethane onto D,
b=2 to 6,
B′=*—(CH 2 ) b′ —* , *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—* ,

B′ being attached as alkyl ester onto the (meth)acrylate reactive group or as urethane onto D′,
b′=2- 6,
D, D′ being independently selected from *—(CH 2 )n—NH—(C═O )—O—* , *—(CH 2 —C(CH 3 ) 2 —CH 2 )—NH—(C═O)—O—* , *—(CH 2 —CH 2 —C(CH 3 ) 2 )—NH—(C═O)—O—*
D and D′ being always attached via the oxygen of the urethane linkage onto B and/or B′,
d=0 or1 and d′=0 or 1 with the proviso that (d+d′)=1 or 2,
n=2 to 5,
R being independently selected from H, methyl,
X being independently selected from H and C1 to C6 alkyl,
“*” representing those site(s) of a moiety of the monomer, where that moiety is bonded to another moiety of the monomer,
wherein the polymerizable monomer (1) being selected from one of the following monomers and mixtures thereof:

with R being independently selected from H and methyl.

2. The dental composition of claim 1 , the initiator being selected from radiation curing, redox curing, heat curing initiators and combinations thereof.

3. The dental composition of claim 1 , comprising the respective components in the following amounts:
polymerizable monomer(s) (1): from about 1 to about 75 wt.-%,
initiator(s): from about 0.1 to about 10 wt.-%, and
filler(s): from about 20 to about 95 wt.-%.

4. The dental composition of claim 1 further comprising a polymerizable monomer (2) bearing an acidic moiety.

5. The dental composition of claim 1 , not comprising either or all of the following components:
Bis-GMA or bisphenol moiety(s) containing components in an amount above 5 wt.-%,
Solvent(s) in an amount above 5 wt.-%.

6. The dental composition of claim 1 , the adhesive composition being characterized by at least one or all of the following features after curing:
compressive strength: at least about 380 MPa;
shrinkage stress: not more than about 2350 μstrain.

7. The dental composition of claim 1 being characterized as follows:
polymerizable monomer(s) (1) being represented by the formula as described in claim 1 in an amount from about 1 to about 75 wt.-%,
initiator(s) being selected from radiation curing or redox curing initiators,
filler(s) being selected from silica, silica/zirconia filler(s) and mixtures thereof in an amount from about 20 to about 90 wt.-%.

8. The dental composition of claim 1 being provided as one or two part system.

9. The dental composition of claim 1 being in a cured state and being provided in the shape of a dental crown, bridge, inlay, onlay, veneer, orthodontic device or dental mill blank.

10. A process for performing a dental procedure comprising:
providing the dental composition of claim 1 ; and
producing a dental filling material, dental cement, crown and bridge material, inlay, onlay, veneer, orthodontic device or dental mill blank.

11. A process for producing a dental mill blank, the process comprising:
providing a dental composition of claim 1 , the dental composition being in its uncured state;
hardening or curing the dental composition to obtain a hardened or cured dental composition;
fixing the hardened dental composition to a holding device; and
the dental composition being provided in the shape of a dental mill blank.

12. A process for producing a dental restoration, the process comprising:
providing a dental mill blank, the dental mill blank comprising the dental composition of claim 1 , the dental composition being in its cured state; and
machining the dental mill blank to obtain a dental restoration.

Assignees

• 3M Innovative Properties Co

Inventors

• Eckert Adrian S
• Cub Michael
• Hailand Bettina
• Kestel Marion B
• Thalacker Christoph
• Dede Karsten

Classifications

• A61K6/887

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

• A61K6/76

  comprising silicon-containing compounds · CPC title

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title