Dental composition with high E-modulus

Patent metadata

Field	Value
Publication number	US-10932995-B2
Application number	US-201816762170-A
Country	US
Kind code	B2
Filing date	Nov 5, 2018
Priority date	Nov 8, 2017
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

The invention relates to a dental composition comprising a resin matrix, a filler matrix in an amount of at least 25 wt. % with respect to the weight of the dental composition, an initiator system, the resin matrix comprising polymerizable monomer(s) comprising two (meth)acrylate moieties connected to a brominated resorcinol, catechol, tyrosol, benzoic acid or phenol moiety. The invention relates also to a dental milling block comprising this composition in its hardened stage.

First claim

What is claimed is:

1. A dental composition comprising:
a filler matrix in an amount of at least 25 wt. % with respect to the weight of the dental composition;
an initiator system; and
a resin matrix comprising a brominated polymerizable monomer(s), the brominated polymerizable monomer(s) characterized by formula (I):

wherein:
a is an integer selected from 0 and 1,
A is selected from:

B is 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 is an integer selected from 2 to 6,
B′ is selected from *—(CH 2 ) b′ —*, *—(CH 2 —CH 2 —O—CH 2 —CH 2 )—*,

b′ is an integer selected from 2 to 6,
R is H or methyl,
X is selected from H, C 1-6 alkyl, and Br,
each Y is independently H or Br,
wherein “*” represents bonding site(s).

2. The dental composition of claim 1 , the brominated polymerizable monomer(s) being characterized by:
having a molecular weight of 400 to 800 g/mol;
not solidifying at 23° C.;
viscosity: 0.2 to 3 Pa*s at 23° C.;
having a refractive index in the range of 1.52 to 1.56; or
a combination thereof.

3. The dental composition of claim 1 , the brominated polymerizable monomer(s) being selected from:

and a combination thereof,
each R is independently selected from H and CH 3 .

4. The dental composition of claim 1 , the initiator system comprising radiation curing initiators, redox-curing initiators, heat-curing initiators, or a combination thereof.

5. The dental composition of claim 1 , the filler system comprising:
aggregated nano filler(s),
agglomerated nano filler(s),
discrete nano filler(s),
or a combination thereof.

6. The dental composition of claim 1 , comprising the components in the following amounts:
resin matrix: 5 to 70 wt. %,
filler matrix: 25 to 90 wt. %, and
initiator system: 0.1 to 10 wt. %,

wherein wt. % is with respect to the weight of the dental composition.

7. The dental composition of claim 1 , further comprising:
non-brominated, non-acidic polymerizable monomer(s) present in an amount of 1 to 50 wt. %;
non-brominated, acidic polymerizable monomer(s) present in an amount of 1 to 50 wt. %;
additive(s) present in an amount of 0.1 to 5 wt. %; or
a combination thereof.

8. The dental composition of claim 1 , being characterized by the following prior to hardening:
viscosity: 5 to 200 Pa*s measured at 23° C.;
pH value: 2 to 8, if brought in contact with wet pH-sensitive paper;
being storage stable for at least 3 months; or
a combination thereof.

9. The dental composition claim 1 , being characterized by the following after hardening:
flexural strength: at least 100 MPa according to ISO 4049:2009(E);
E-modulus: at least 10 MPa according to ISO 4049:2009(E);
shape: dental crown, bridge, inlay, onlay or veneer; or
a combination thereof.

10. The dental composition of claim 1 , comprising:
water or C 1 to C 4 alcohols in an amount of no more than 10 wt. %;
bisphenol A-glycidyl methacrylate in an amount of no more than 10 wt. %; or
a combination thereof,
wherein wt. % is with respect to the whole composition.

11. The dental composition of claim 1 ,
the initiator system comprising a radiation curing initiator, a redox-curing initiator, or a combination thereof, and
the filler matrix present in an amount of 25 to 90 wt. %, the filler matrix comprising nano-fillers selected from aggregated nano filler(s), agglomerated nano filler(s), discrete nano filler(s), and a combination thereof,
wherein:
A is selected from:

B is independently 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 )—*, and

and
X is selected from H, methyl, ethyl, hexyl, tert-butyl, and Br, and wherein the resin matrix is present in an around from 5 to 75 wt. %.

12. The dental composition of claim 1 , for use in producing a dental restorative material.

13. A kit of parts comprising:
the dental composition of claim 1 in a hardened or unhardened state;
one or more of:
a dental adhesive,
a dental cement, and
an applicator; and

a set of instructions directing a user to contact the dental composition to a tooth surface.

14. A dental milling block comprising the dental composition of claim 1 in its hardened state.

Assignees

• 3M Innovative Properties Co

Inventors

• Eckert Adrian S
• Dede Karsten
• Thalacker Christoph H
• Raia Gioacchino

Classifications

• A61C13/0022

  Blanks or green, unfinished dental restoration parts · CPC title

• A61K6/887

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

• A61K6/80 Primary

  Preparations for artificial teeth, for filling teeth or for capping teeth · CPC title

• A61K6/891 Primary

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

• C07C69/007

  Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom · CPC title