Dental composition and use thereof

Patent metadata

Field	Value
Publication number	US-10004669-B2
Application number	US-201515119241-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Feb 18, 2014
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

The invention relates to a dental composition comprising polymerizable monomer (1), initiator component(s), 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, and oxygen, bisphenol moieties. The invention also relates to the use of the dental composition as or for producing a dental filling material, crown and bridge material, inlay, onlay, veneer or dental mill blank.

First claim

The invention claimed is:

1. A dental composition comprising:
Polymerizable monomer (1),
Initiator component(s),
Filler component(s) in an amount of more than 20 wt.-%, wt.-% with respect to the whole weight of the composition,
the polymerizable monomer (1) being characterized by formula (I)

with:
B—O-A-[—O—B′—] a representing the unsymmetrical monomer backbone as linkage between the reactive (meth)acrylate moieties,
a=0 or 1,
A being selected from:

A being always attached as aryl-alkyl ether onto B and/or B′,
B being selected from:
*—(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 always attached as alkyl ester onto the (meth)acrylate reactive moiety,
b=2 to 6,
B′ being selected from *—(CH2) b′ —*, *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—*,

B′ being always attached as alkyl ester onto the (meth)acrylate reactive moiety,
b′=2 to 6,
R═H, methyl,
X being selected from H, methyl, ethyl, hexyl, tert-butyl,
“*” representing those site(s) of a moiety of the monomer, where that moiety is bonded to another moiety of the monomer.

2. The dental composition according to claim 1 , the polymerizable monomer (1) being characterized by either formula (Ia) or formula (Ib)

with:
B—O-A-O—B′ being an unsymmetrical monomer backbone as linkage between the reactive (meth)acrylate moieties,
A being selected from

A being always attached as aryl-alkyl ether onto B and B′,
B being selected from:
*—(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 always attached as alkyl ester onto the (meth)acrylate reactive moiety,
b=2 to 6,
B′ being selected from: *—(CH 2 ) b —*, *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—*,

B′ being always attached as alkyl ester onto the (meth)acrylate reactive moiety,
b′=2 to 6,
R═H, methyl,
X═H, methyl, ethyl, hexyl, tert-butyl;
or

with:
B—O-A being an unsymmetrical monomer backbone as linkage between the reactive (meth)acrylate moieties,
A being selected from:

A being always attached as aryl-alkyl ether onto B and always attached as alkyl ester onto the (meth)acrylate reactive moiety,
B being selected from:
*—(CH 2 ) b —*, *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—*,

B being always attached as alkyl ester onto the (meth)acrylate reactive moiety,
b=2 to 6,
R═H, methyl;
“*” representing those sites of a moiety of the monomer, where that moiety is bonded to another moiety of the monomer.

3. The dental composition according to claim 1 , wherein the polymerizable monomer (1) has a molecular weight of about 300 to about 600, the polymerizable monomer (1) does not solidify at 23° C. or both.

4. The dental composition according to claim 1 , the polymerizable monomer (1) being selected from one of the following monomers and mixtures thereof:

5. The dental composition according to claim 1 , the polymerizable monomer (1) being selected from one of the following monomers and mixtures thereof:

R being always independently selected from H and CH3.

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

7. The dental composition according to 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.-%,
Filler(s): from about 20 to about 90 wt.-%.

8. The dental composition according to claim 1 further comprising in addition a polymerizable monomer (3) comprising a urethane moiety.

9. The dental composition according to claim 1 not comprising solvent(s) in an amount above about 10 wt.-%.

10. The dental composition according to claim 1 , wherein the dental composition has at least one or all of the following features before curing:
Viscosity: from about 0.5 to about 200 Pa*s measured at 23° C. with a shear rate of 100 l/s;
pH value if brought in contact with water: about 1 to about 9,
radiation or redox curing, and
storage stable.

11. The dental composition according to claim 1 , wherein the dental composition after curing has a
Compressive strength determined according to ISO 4049 using specimens having the dimension of 3 mm×3 mm×5 mm of at least 430 MPa; and a
Compressive strength determined according to DIN 53454 using cylindrical specimens with a diameter of 4 mm and a height of 8 mm of at least 280 MPa.

12. The dental composition according to claim 1 , wherein the
Polymerizable monomer(s) (1) is present in an amount from about 1 to about 75 wt.-%,
Initiator(s), being selected from radiation curing or redox curing initiator(s), and Filler(s) being selected from silica or silica/zirconia filler(s) and mixtures thereof, in an amount from about 20 to about 90 wt.-%.

13. The dental composition according to claim 1 being provided as one or two part system.

14. An article comprising:
the dental composition according to claim 1 , the article in the form of a dental filling material, crown and bridge material, inlay, onlay, veneer or dental mill blank.

15. A method comprising:
applying a rapid-prototyping technique to the dental composition according to claim 1 to produce a dental restoration.

16. The method according to claim 15 , wherein the dental restoration is selected from a dental crown, a bridge, or an onlay or inlay.

Assignees

• 3M Innovative Properties Co

Inventors

• Eckert Adrian S
• Cub Michael
• Hailand-Newhook Bettina
• Kestel Marion B
• Thalacker Christoph
• Dede Karsten
• Hoheisel Uwe H
• Hecht Reinhold
• Loll Henry
• Hofmann Bernhard

Classifications

• A61K6/887 Primary

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

• A61K6/61 Primary

  Cationic, anionic or redox initiators · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title

• A61K6/77

  Glass · CPC title