Two-component self-adhesive dental composition, process of production and use thereof

Patent metadata

Field	Value
Publication number	US-2017216152-A1
Application number	US-201515324760-A
Country	US
Kind code	A1
Filing date	Jul 7, 2015
Priority date	Jul 10, 2014
Publication date	Aug 3, 2017
Grant date	—

Abstract

The present invention relates to a kit of parts comprising Part A and Part B, Part A comprising: ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof, optionally polymerizable component(s) without acidic moieties, optionally polymerizable component(s) with acidic moieties, and optionally filler(s), Part B comprising polymerizable component(s) without acidic moieties, polymerizable component(s) with acidic moieties, transition metal component(s), organic peroxide(s), and optionally filler(s), The invention is also directed to a redox initiator system comprising ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof, transition metal component(s), preferably comprising a copper or iron ion containing salt, organic peroxide(s), preferably comprising a hydroperoxide or di-peroxide. The kit of parts and redox initiator system are particularly useful in the dental field.

First claim

1 . A kit of parts for dental use comprising Part A and Part B,
Part A comprising:
ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof;
optionally polymerizable component(s) without acidic moieties;
optionally polymerizable component(s) with acidic moieties; and
optionally filler(s); and
Part B comprising:
polymerizable component(s) without acidic moieties;
polymerizable component(s) with acidic moieties;
transition metal component(s);
organic peroxide(s) selected from hydroperoxide(s) and di-peroxide(s); and
optionally filler(s).

2 . The kit of parts of claim 1 comprising Part A and Part B,
Part A comprising:
ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof;
polymerizable component(s) without acidic moieties;
optionally polymerizable component(s) with acidic moieties,
filler(s); and

Part B comprising:
polymerizable component(s) without acidic moieties;
polymerizable component(s) with acidic moieties;
transition metal component(s);
organic peroxide(s) selected from hydroperoxide(s) and di-peroxide(s),
filler(s); and

the kit of parts being provided as a paste/paste system.

3 . The kit of parts of claim 1 comprising Part A and Part B,
Part A comprising:
ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof; and
filler(s); and

Part B comprising:
polymerizable component(s) without acidic moieties;
polymerizable component(s) with acidic moieties;
transition metal component(s); and
organic peroxide(s) selected from hydroperoxide(s) and di-peroxide(s),

the kit of parts being provided as a powder/liquid system.

4 . The kit of parts of claim 1 , the transition metal component(s) comprising as transition metal Ti, V, Cr, Mn, Co, Ni, Cu, Fe, Zn either in hydrated or in dry form and mixtures thereof, the transition metal component(s) being preferably selected from copper acetate, copper chloride, copper benzoate, copper acetylacetonate, copper naphthenate, copper carboxylates, copper bis(1-phenylpentan-1,3-dione), copper complexes, either in hydrated or in dry form and mixtures thereof.

5 . The kit of parts of claim 1 , the organic peroxide(s) being a hydroperoxide comprising the structural moiety R—O—O—H, with R being an alkyl, branched alkyl, cycloalkyl, alkylaryl or aryl moiety.

6 . The kit of parts of claim 1 , the organic peroxide(s) being a di-peroxide comprising the moiety R 1 —O—O—R 2 —O—O—R 3 , with R 1 and R 3 being independently selected from H, alkyl, branched alkyl, cycloalkyl, alkylaryl or aryl and R 2 being selected from alkyl or branched alkyl.

7 . The kit of parts of claim 1 , comprising in addition a photoinitiator system, the photoinitiators system preferably comprising a sensitizer and a further reducing agent.

8 . The kit of parts of claim 1 , being provided as a liquid/liquid, paste/paste or powder/liquid formulation.

9 . The kit of parts of claim 1 , the composition obtained when combining Part A and Part B comprising the components in the following amounts:
Ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof: from 0.01 wt.-% to 5 wt.-%; Transition metal component(s): from 0.00001 wt.-% to 3 wt.-%; Organic peroxide(s): from 0.01 wt.-% to 5 wt.-%; Filler(s): from 1 wt.-% to 90 wt.-%; Polymerizable component(s) without acidic moieties: from 5 wt.-% to about 65 wt.-%; and Polymerizable component(s) with acidic moieties: from 2 wt.-% to about 50 wt.-%,
wt.-% with respect to the amount of the whole composition.

10 . The kit of parts of claim 1 , not comprising at least one or more or all of the following components:
component(s) comprising a sulfinate moiety; component(s) comprising a barbituric acid moiety; component(s) comprising a thiobarbituric acid moiety; component(s) comprising an aryl borate moiety; and component(s) comprising a thiourea moiety; or mixtures thereof.

11 . A dental composition for dental use as obtainable by mixing the compositions of Part A and Part B of the kit of parts of claim 1 , and curing the resulting mixture, the dental composition being a self-etching, self-adhesive, and self-curing composition.

12 . The dental composition of claim 1 , the composition obtained immediately after mixing Part A and Part B having a pH value below 7, if brought into contact with water.

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

14 . The dental composition of claim 1 being characterized by at least one or more of the following properties:
a) Flexural strength: at least 50 MPa determined according to according to ISO 4049:2000;
b) Adhesion to dentin: at least 5 MPa determined according to the wire loop test method;
c) Adhesion to enamel: at least 5 MPa determined according to the wire loop test method.

15 . Use of a redox initiator system comprising:
ascorbic acid, component(s) comprising an ascorbic acid moiety or derivative(s) thereof; transition metal component(s), preferably comprising a copper or iron ion containing salt; and organic peroxide(s) selected from hydroperoxide(s) and di-peroxide(s),
for hardening a dental composition comprising polymerizable component(s) with acidic moieties, wherein the component(s) are as described in claim 1 .

Assignees

• 3M Innovative Properties Co

Inventors

• Hecht Reinhold
• Ludsteck Manfred
• Stippschild-Boxler Andrea
• Raia Gioacchino
• Guggenberger Rainer A

Classifications

• A61K6/54

  Filling; Sealing · CPC title

• A61K6/80

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

• A61K6/30

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

• A61K6/77

  Glass · CPC title

• A61K6/61 Primary

  Cationic, anionic or redox initiators · CPC title