IP Library Granted Patent US 10,932,994
Granted Patent B2
US 10,932,994 · App. 15/324,760 · Granted Mar 2, 2021

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

Inventors: Reinhold Hecht (Kaufering, DE); Manfred Ludsteck (Geretsried, DE); Andrea Stippschild-Boxler (Landsberg, DE); Gioacchino Raia (Turkenfeld, DE); Rainer A. Guggenberger (Herrsching, DE)
Assignee: 3M Innovative Properties Company
A61K6/61A61K6/20A61K6/30A61K6/54A61K6/76A61K6/77A61K6/80A61K6/887
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Quick Facts
Patent No.
US 10,932,994
App. No.
15/324,760
Granted
Mar 2, 2021
Kind
B2
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.

Claims (47)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066445/0328 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2017
From: HECHT, REINHOLD; LUDSTECK, MANFRED; STIPPSCHILD-BOXLER, ANDREA; RAIA, GIOACCHINO; GUGGENBERGER, RAINER A.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 043358/0368 →
Priority Claims (1)
EP 14176520 · Jul 10, 2014 · regional
Continuity (1)
Related Publication 20170216152A1 · Aug 3, 2017