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

Patent metadata

Field	Value
Publication number	US-10932994-B2
Application number	US-201515324760-A
Country	US
Kind code	B2
Filing date	Jul 7, 2015
Priority date	Jul 10, 2014
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

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

The invention claimed is:

1. A storage-stable kit of parts for providing a curable composition, the storage-stable kit of parts comprising:
Part A comprising:
one or more of ascorbic acid, an alkali earth metal salt thereof, and an ester thereof,
polymerizable component(s) without acidic moieties,
optionally polymerizable component(s) with acidic moieties, and
filler(s);

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
filler(s),

wherein each one of Part A and Part B is a paste and free of added water,
wherein Part A and Part B are storage stable at ambient conditions for a period of at least 4 weeks,
wherein the curable composition is self-curable,
wherein the curable composition adheres to dentin, and
a set of instructions directing a user to combine Part A and Part B to provide a cured composition.

2. The kit of parts of claim 1 , the transition metal component(s) comprising Ti, V, Cr, Mn, Co, Ni, Cu, Fe, Zn, or a combination thereof, wherein the transition metal component is in hydrated or in dry form.

3. The kit of parts of claim 1 , the organic peroxide(s) represented by the formula R—O—OH, wherein R is alkyl, branched alkyl, cycloalkyl, alkylaryl, or aryl.

4. The kit of parts of claim 1 , the organic peroxide(s) represented by the formula R 1 —O—O—R 2 —O—O—R 3 , wherein R 1 and R 3 are independently selected from H, alkyl, branched alkyl, cycloalkyl, alkylaryl or aryl; and R 2 is selected from alkyl or branched alkyl.

5. The kit of parts of claim 1 , further comprising a photoinitiator system.

6. The kit of parts of claim 1 , Part A and Part B together comprising the components in the following amounts:
one or more alkali earth metal salts of ascorbic acid 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) up 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.-%,
wherein wt.-% is with respect to the amount of the composition.

7. The kit of parts of claim 1 , not comprising one or more 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.

8. The kit of parts of claim 1 ,
Part A comprising:
ascorbic acid, and

Part B comprising:
at least 4 wt % polymerizable component(s) with acidic moieties.

9. The kit of parts 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.

10. The kit of parts of claim 1 , wherein upon combined Part A and Part B produces a composition characterized by 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; and
c) Adhesion to enamel: at least 5 MPa determined according to the wire loop test method.

11. The kit of parts of claim 1 , wherein the transition metal component(s) is selected from copper acetate, copper chloride, copper benzoate, copper acetylacetonate, copper naphthenate, copper carboxylates, copper bis(1-phenylpentan-1,3-dione), copper complexes, and a combination thereof, in hydrated or in dry form.

12. The kit of parts of claim 5 , the photoinitiator system comprising a sensitizer and a reducing agent.

Assignees

• 3M Innovative Properties Co

Inventors

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

Classifications

• A61K6/887

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

• A61K6/30

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

• A61K6/54

  Filling; Sealing · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title

• A61K6/80

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