Curable composition with shortened setting time, process of production and use thereof

Patent metadata

Field	Value
Publication number	US-9283153-B2
Application number	US-201214237502-A
Country	US
Kind code	B2
Filing date	Aug 10, 2012
Priority date	Aug 12, 2011
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

The invention relates to a curable dental composition being prepared by mixing a base paste and a catalyst paste, “the base paste comprising component(s) (A) with curable moieties (AC),” the catalyst paste comprising a catalyst (C) being able to initiate or catalyse a crosslinking reaction involving components (A) upon mixing base paste and catalyst paste, the curable composition comprising a component (X) with reactive moieties, component (X) being either produced during the curing reaction or being present in either the base paste or the catalyst paste before the crosslinking reaction is initiated or catalysed, component X being different from component(s) (A), either base paste or catalyst paste comprising a reactant (Y), reactant (Y) being able to interact with component (X), but not taking part in the crosslinking reaction, the curable composition being able to produce energy in an amount sufficient to increase the temperature T1 of the composition being present 20 s after mixing the base paste and the catalyst paste to a temperature T2 being from about 6 to about 20° C. above T1.

First claim

The invention claimed is:

1. A curable dental composition being prepared by mixing a base paste and a catalyst paste,
the base paste comprising component(s) (A) with curable moieties (AC) selected from a combination of at least one organopolysiloxane with at least 2 aliphatically unsaturated groups and at least a component comprising Si—H moieties,
the catalyst paste comprising a catalyst (C) comprising a Pt containing component,
the curable composition comprising a component (X) comprising at least one Si—H group as reactive moiety, component (X) being present in the base paste,
either base paste or catalyst paste comprising a reactant (Y), reactant (Y) being able to interact with component (X), but not taking part in a crosslinking reaction,
reactant (Y) being selected from a silane component with only one unsaturated moiety, an alkyl vinyl ether component, an alkyl allyl ether component and mixtures thereof,
the molar ratio of the reactive moieties of component (X) to reactant (Y) being from 1.2 to 5,
component (A) being present in an amount from 15 to 70 wt.-% with respect to the weight of the whole composition,
catalyst (C) being present from 0.00005 to 35 wt.% with respect to the weight of the whole composition,
reactant (Y) being present from 0.5 to 6 wt.-% with respect to the weight of the whole composition,
the curable composition being able to produce energy in an amount sufficient to increase the temperature T1 of the composition measured 20 s after mixing the base paste and the catalyst paste to a temperature T2 being from about 6 to about 20° C. above T1.

2. The composition according to claim 1 being characterized by at least one of the following features after curing:
a tensile strength (according to DIN 53504) of about 0.1 to about 5 MPa,
an elongation at break (according to DIN 53 504) of about 10 to about 300%,
a Shore A hardness (according to IN 53 505) of about 15 to about 75,
a recovery from deformation (according to ISO 4823): at least about 90%,
a density (according to the Archimedes method; weight of 1 ml cured composition) of the composition of about 0.8 to about 2 g/ml.

3. The composition according to claim 1 , the composition being characterized by at least one of the following features before or during curing:
a consistency (according to ISO 4823) of 0 or 1 (corresponding to at most 35 mm) or 2 (corresponding to 31 mm to 41 mm) or 3 (corresponding to at least 36 mm); and/or
a setting time within about 15 or about 10 min after mixing at ambient conditions.

4. The composition according to claim 1 , reactant (Y) being characterized by at least one of the following features:
molecular weight: from about 50 to about 1,000;
being solid or liquid at room temperature;
being present in an amount of at least 0.5 wt.-% with respect to the whole composition;
ratio of component (X) to reactant (Y): from about 6:1 to 20:1 with respect to weight.

5. The composition according to claim 1 , reactant (Y) being a silane component with only one unsaturated moiety, the unsaturated moiety being selected from vinyl, allyl, vinyl ether, allyl ether, >C═CH—CH 2 — or >C═C(CH 3 )—CH 2 —.

6. The composition according to claim 1 , reactant (Y) being characterized by the following formula
R 2 R 3 C═CR 1 —A—SiR 3

wherein
R being a monovalent alkyl, aryl, alkoxy, aryloxy group, O—SiR 4 3 or H, wherein the residue R may include heteroatoms selected from O, Cl, Br, F and I, the residues R being different or equal,
R 1 , R 2 , R 3 being equal or different and comprising hydrogen or monovalent alkyl, aryl wherein the residues R 1 , R 2 and R 3 may include heteroatoms selected from O, Cl, Br, F, I,
R 4 being alkyl or aryl, wherein two or three of the residues R 4 in O—SiR 4 3 can combine to a cyclic or polycyclic structure,
A being a divalent linear, branched or cyclic hydrocarbon group, optionally comprising an aromatic moiety, with at least one methylene group directly attached to the unsaturation.

7. The composition according to claim 1 , reactant (Y) being selected from
H 2 C═CH—CH 2 Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 3
H 2 C═CH—CH 2 Si(i-CH 3 H 7 ) 3
H 2 C═CH—(CH 2 ) 2 Si(i-C 3 H 7 ) 3
H 2 C═CH—(CH 2 ) 3 Si(i-C 3 H 7 ) 3
H 2 C═CH—(CH 2 ) 4 Si(i-C 3 H 7 ) 3
H 2 C═CH—(CH 2 ) 8 Si(i-C 3 H 7 ) 3
H 2 C═CH—CH 2 Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—CH 2 Si(C 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 2 Si(C 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 3 Si(C 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 4 Si(C 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 8 Si(C 2 H 5 ) 3
H 2 C═CH—CH 2 Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—CH 2 Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—CH 2 —O—Si(CH 3 ) 3
H 2 C═CH—CH 2 —O—Si(C 2 H 5 ) 3
H 2 C═CH—CH 2 —O—Si(i-C 3 H 7 ) 3
H 2 C═CH—CH 2 —O—Si(CH 3 ) 2 (t-C 4 H 9 )
H 2 C═CH—CH 2 —O—Si(CH 3 ) 2 (n-C 18 H 37 )
H 2 C═CH—CH 2 —O—Si(CH 3 ) 2 (C 6 H 5 )
H 2 C═CH—CH 2 Si(CH 3 ) 2 —O—Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 2 —O—Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 2 —O—Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 2 —O—Si(CH 3 ) 3
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 2 —O—Si(CH 3 ) 3
H 2 C═CH—CH 2 Si(CH 3 )(—O—Si(CH 3 ) 3 ) 2
H 2 C═CH—(CH 2 ) 2 Si(CH 3 )(—O—Si(CH 3 ) 3 ) 2
H 2 C═CH—(CH 2 ) 3 Si(CH 3 )(—O—Si(CH 3 ) 3 ) 2
H 2 C═CH—(CH 2 ) 4 Si(CH 3 )(—O—Si(CH 3 ) 3 ) 2
H 2 C═CH—(CH 2 ) 8 Si(CH 3 )(—O—Si(CH 3 ) 3 ) 2
H 2 C═CH—CH 2 Si(—O—Si(CH 3 ) 3 ) 3
H 2 C═CH—(CH 2 ) 2 Si(—O—Si(CH 3 ) 3 ) 3
H 2 C═CH—(CH 2 ) 3 Si(—O—Si(CH 3 ) 3 ) 3
H 2 C═CH—(CH 2 ) 4 Si(—O—Si(CH 3 ) 3 ) 3
H 2 C═CH—(CH 2 ) 8 Si(—O—Si(CH 3 ) 3 ) 3
H 2 C═CH—CH 2 Si(OCH 3 ) 3
H 2 C═CH—(CH 2 ) 2 Si(OCH 3 ) 3
H 2 C═CH—(CH 2 ) 3 Si(OCH 3 ) 3
H 2 C═CH—(CH 2 ) 4 Si(OCH 3 ) 3
H 2 C═CH—(CH 2 ) 8 Si(OCH 3 ) 3
H 2 C═CH—CH 2 Si(OC 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 2 Si(OC 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 3 Si(OC 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 4 Si(OC 2 H 5 ) 3
H 2 C═CH—(CH 2 ) 8 Si(OC 2 H 5 ) 3
H 2 C═CH—CH 2 Si(C 6 H 5 ) 3
H 2 C═CH—(CH 2 ) 2 Si(C 6 H 5 ) 3
H 2 C═CH—(CH 2 ) 3 Si(C 6 H 5 ) 3
H 2 C═CH—(CH 2 ) 4 Si(C 6 H 5 ) 3
H 2 C═CH—(CH 2 ) 8 Si(C 6 H 5 ) 3
H 2 C═C(CH 3 )—CH 2 Si(CH 3 ) 3
H 2 C═CH—CH 2 Si(p-C 6 H 4 OCH 3 )
H 2 C═CH—CH 2 Si(CH 3 ) 2 H
H 2 C═CH—(CH 2 ) 2 Si(CH 3 ) 2 H
H 2 C═CH—(CH 2 ) 3 Si(CH 3 ) 2 H
H 2 C═CH—(CH 2 ) 4 Si(CH 3 ) 2 H
H 2 C═CH—(CH 2 ) 8 Si(CH 3 ) 2 H

and mixtures thereof.

8. The composition according to claim 1 further comprising at least one of filler(s) or additive selected from hydrophilating agent(s), colourant(s), dye(s), pigment(s), flavourant(s), stabilizer(s), hydrogen scavenger(s) and mixtures thereof.

9. The composition according to claim 1 further comprising a F-containing component, wherein the F-containing compound is characterized by the following formula
T 1 -X-[(O—CF 2 —CF 2 ) u -(O—CF 2 ) v -(O—CF(CF 3 )—CF 2 ) w -(O—CF 2 —CF 2 —CF 2 ) x —O]-X-T 2

with u=0 to 8, v=0 to 8, w=0 to 8 and x=0 to 8 and u+v+w+x≧1, wherein T 1 and T 2 can be equal or different and are ind

Assignees

• Osswald Peter U
• Hoffmann Henning
• Zech Joachim W
• 3M Innovative Properties Co

Inventors

• Osswald Peter U
• Hoffmann Henning
• Zech Joachim W

Classifications

• A61K6/90 Primary

  Compositions for taking dental impressions · CPC title

• A61K6/887

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

• C08L51/085

  on to polysiloxanes · CPC title

• A61K6/10 Primary

  Human Necessities · mapped topic

• A61K6/083

  Human Necessities · mapped topic