ONE COMPONENT SELF-ADHESIVE DENTAL COMPOSITION, PROCESS OF PRODUCTION AND USE THEREOF

• US 20140329205A1
• Filed: 11/30/2012
• Published: 11/06/2014
• Est. Priority Date: 12/01/2011
• Status: Active Grant

• Current Assignee: Solventum Intellectual Properties Company (Solventum Corp.)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Hecht, Reinhold, Stippschild, Andrea, Raia, Gioacchino, Ludsteck, Manfred, Guggenberger, Rainer, Hasanaj, Vitore
• Granted Patent: US 9,132,069 B2
• Time in Patent Office: Days
• US Class Current: 433/228.1
• CPC Class Codes: A61C 19/003 Apparatus for curing resins by radiation
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 43/02 Homopolymers or copolymers of monomers containing phosphorus
• CPC Class Codes: C09J 133/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C09J 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09J 175/16 having terminal carbon-to-carbon unsaturated bonds

Abstract

The invention relates to a one-component self-adhesive composition for dental use comprising radically polymerizable component(s) with an acidic moiety as component A, radically polymerizable component(s) without an acidic moiety as component (B), an oxidizing agent comprising persulfate(s) as component (C), transition metal component(s) as component (D), photoinitiator system(s) as component (E), optionally non acid-reactive filler(s) as component (F), and optionally additive(s) as component (G).

Claims

1. A one-component self-adhesive composition for dental use comprising

a) radically polymerizable component(s) with an acidic moiety as component A,

b) radically polymerizable component(s) without an acidic moiety as component (B),

c) an oxidizing agent comprising persulfate(s) as component (C),

d) transition metal component(s) as component (D),

e) photoinitiator system as component (E),

f) optionally non acid-reactive filler(s) as component (F), and

g) optionally additive(s) as component (G),

the composition not comprising basic filler(s).

2. The composition according to the preceding claim not comprising component(s) comprising a barbituric acid moiety, a thiobarbituric acid moiety, a sulfinate moiety, an aryl borate moiety or mixtures thereof.

3. The composition according to claim 1, wherein the oxidizing agent fulfils at least one of the following features:

not containing carbon-carbon based moieties,

being water-soluble.

4. The composition according to claim 1, wherein the transition metal component(s) is selected from organic and/or inorganic salts from titanium, vanadium, chromium, manganese, cobalt, nickel, copper, zinc, either in hydrated or in dry form and mixtures thereof.

5. The composition according to claim 1, wherein the transition metal component is a copper component being selected from copper acetate, copper chloride, copper benzoate, copper acetylacetonate, copper naphthenate, copper carboxylates, copper procetonate, copper complexes, either in hydrated or in dry form and mixtures thereof.

6. The composition according to claim 1, wherein the photoinitiator system is selected from

a) di-component system(s) comprising an amine and an alpha-diketon component,

b) three-component system(s) comprising an iodonium salt, a sensitizer and a donor component,

c) system(s) comprising an acyl or bisacylphosphine oxide.

7. The composition according to claim 1, wherein the radically polymerizable component with an acidic moiety is selected from components with the formula

A_n-B—

C_m  

 

(I)

with A being an ethylenically unsaturated group, such as a (meth)acryl moiety,

B being a spacer group, selected from (i) linear or branched C1 to C12 alkyl, optionally substituted with other functional groups (ii) C6 to C12 aryl, optionally substituted with other functional groups, and (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, wherein the other functional groups are selected from halogenides and/or OH and

C being an acidic group, with m, n=1, 2, 3, 4, 5 or 6,

wherein the acidic group comprises one or more carboxylic acid residues, such as —

COOH or —

CO—

O—

CO—

, phosphoric acid residues, such as —

O—

P(O)(OH)OH, phosphonic acid residues, such as —

C—

P(O)(OH)OH, sulfinic acid residues, such as —

SO₂H or sulphonic acid residues, such as —

SO₃H,

and mixtures thereof.

8. The composition according to claim 1, wherein the radically polymerizable component without an acidic moiety is selected from mono-, di- or poly-acrylates and methacrylates, bis-acrylates and bis-methacrylates of polyethylene glycols of molecular weight 200-500, co-polymerizable mixtures of acrylated monomers, acrylated oligomers, vinyl moieties bearing compounds and mixtures thereof, wherein the radically polymerizable component may be substituted with a hydroxyl group, 1,3-diketo group or both.

9. The composition according to claim 1, wherein component (B) comprises a component (B1) with a hydroxyl group and/or 1,3-diketo group and a component (B2) not having either of these functionalities.

10. The composition according to claim 1 being characterized by at least one of the following features after hardening:

Flexural strength determined according to ISO 4049;

2000;

at least about 50 MPa,

E-Modulus determined according to ISO 4049;

2000;

at least about 3500 MPa,

Adhesion to dentin determined according to wire loop test method;

at least about 5 MPa,

Adhesion to enamel determined according to wire loop test method;

at least about 7 MPa.

11. The composition according to claim 1 comprising the components in the following amounts:

a) radically polymerizable component(s) with an acidic moiety;

from about 3 to about 80 wt.-%,

b) radically polymerizable component(s) without an acidic moiety;

from about 5 to about 65 wt.-%,

c) oxidizing agent;

from about 0.1 to about 10 wt.-%,

d) transition metal component;

from about 0.0001 to about 3 wt.-%,

e) photoinitiator system;

from about 0.1 to about 5 wt.-%,

f) filler(s);

from 0 to about 90 wt.-%,

g) additives;

from 0 to about 15 wt.-%,

wt.-% with respect to the weight of the whole composition.

12. The composition according to claim 1 for use as anterior or posterior filling, adhesive, cavity liner, flowable, cement, coating composition, root canal filler, root canal sealant, core build-up material or a combination thereof.

13. The composition according to claim 1 being contained in a container.

14. The composition according to claim 1 being a self-adhesive, photo-curable system.

15. Method comprising the steps of a) applying the composition as described in claim 1 to a surface, b) curing the composition by applying radiation, the method not comprising an additional mixing step and/or etching step.