Adhesive bonding composition and use thereof

Patent metadata

Field	Value
Publication number	US-9844493-B2
Application number	US-201515119172-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Feb 18, 2014
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

An adhesive dental composition comprising a polymerizable monomer (1), a polymerizable monomer (2) comprising an acidic moiety, initiator component(s), filler component(s) in an amount of less than about 15 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 adhesive dental composition as dental adhesive, sealant, cement or for bonding or cementing a material to the surface of hard dental tissue.

First claim

The invention claimed is:

1. An adhesive dental composition comprising:
Polymerizable monomer (1),
Polymerizable monomer (2) comprising an acidic moiety,
Initiator component(s),
Filler component(s) in an amount of less than about 15 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 an 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 )—*,

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 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 adhesive 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 adhesive dental composition according to claim 1 being characterized by at least one of the following features:
the polymerizable monomer (1) having a molecular weight of about 300 to about 600;
the polymerizable monomer (1) not solidifying at 23° C.;
the adhesive composition having a pH value of less than about 4, if brought in contact with water;
being liquid at 23° C. and 1013 mbar.

4. The adhesive dental composition according to claim 1 , the polymerizable monomer (1) being selected from the group consisting of:

and mixtures thereof.

5. The adhesive dental composition according to claim 1 , the polymerizable monomer (1) being selected from the group consisting of:

and mixtures thereof,
R being always independently selected from H and CH 3 .

6. The adhesive dental composition according to claim 1 , the polymerizable monomer (2) with an acidic moiety being selected from a component which is characterized by the following formula and mixtures thereof:
A n -B-C m
with A being an ethylenically unsaturated group, such as a (meth)acryl moiety,
B being a spacer group, such as (i) linear or branched C1 to C12 alkyl, optionally substituted with other functional groups (e.g. halogenides (including Cl, Br, I), OH or mixtures thereof) (ii) C6 to C12 aryl, optionally substituted with other functional groups (e.g. halogenides, OH or mixtures thereof), (iii) organic group having 4 to 20 carbon atoms bonded to one another by one or more ether, thioether, ester, thioester, thiocarbonyl, amide, urethane, carbonyl and/or sulfonyl linkages, and
C being an acidic group,
m, n being independently selected from 1, 2, 3, 4, 5 or 6,
wherein the acidic group C comprises one or more carboxylic acid residues, phosphoric acid residues, phosphonic acid residues, sulphonic acid residues, or sulfinic acid residues.

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

8. The adhesive dental composition according to claim 1 comprising in addition at least one or more of the following component(s):
Polymerizable monomer (3) without an acidic moiety being different from polymerizable monomer (1),
Additive(s).

9. The adhesive dental composition according to claim 1 comprising the respective components in the following amounts:
Polymerizable monomer(s) (1): from about 5 to about 85 wt.-%,
Polymerizable monomer(s) (2): from about 1 to about 80 wt.-%,
Polymerizable monomer(s) (3): from 0 to about 70 wt.-%,
Initiator(s): from about 0.1 to about 10 wt.-%,
Filler(s): from about 0 to about 14 wt.-%,
Additive(s): from 0 to about 5 wt.-%.

10. The adhesive dental composition according to claim 1 not comprising acid reactive filler(s).

11. The adhesive dental composition according to claim 1 , the adhesive composition being characterized by at least one or all of the following features before curing:
Viscosity: from about 0.05 to about 5 Pa*s at 23° C.;
pH value if brought in contact with water: about 0 to about 3,
radiation curing,
storage stable,
being provided as a one-component mixture.

12. The adhesive dental composition according to claim 1 , the adhesive composition being characterized by at least one or all of the following features after curing:
Adhesion of the composition to dentin: determined ac

Assignees

• 3M Innovative Properties Co

Inventors

• Eckert Adrian S
• Cub Michael
• Hailand Bettina
• Edelmann Ines
• Thalacker Christoph
• Dede Karsten
• Hoheisel Uwe H
• Hecht Reinhold

Classifications

• A61K6/76 Primary

  comprising silicon-containing compounds · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• A61K6/30 Primary

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title