US 8,461,283 B2Granted

Room-temperature vulcanizable organopolysiloxane compound to give an elastomer and novel organopolysiloxane polycondensation catalysts

AssigneeBluestar Silicones France SAS

InventorsChristian Maliverney, Laurent Saint-Jalmes

Life of this patent

Estimating the term…

Abstract

The present invention relates to an organopolysiloxane composition that can be vulcanized at room temperature into an elastomer that is crosslinked by polycondensation and that does not contain alkyltin-based catalysts and also to novel organopolysiloxane polycondensation catalysts.

Claims18

Dependent claims

A single component organopolysiloxane composition, comprising a silicone base B capable of curing via polycondensation reaction into a silicone elastomer comprising at least one linear polyorganosiloxane oil C capable of crosslinking via polycondensation into an elastomer functionalized at its ends by hydrolysable radicals obtained by condensation of a precursor bearing hydroxyl functional groups with a crosslinking silane bearing hydrolysable radicals, the linear polyorganosiloxane oil C having functionalized ends of alkoxy, oxime, acyl and/or enoxy type, and a catalytically effective amount of at least one polycondensation catalyst which is a metal complex or salt A of formula (1), (2) or (3) below:

[M(L1)r1(L2)r2(Y)x] (1)
in which:
r1≧1, r2≧0 and x≧0;
the symbol M represents a metal selected from the group consisting of:
copper, silver, boron, scandium, cerium, ytterbium, bismuth, molybdenum, germanium and manganese;
the symbol L1 represents a ligand which is a β-dicarbonylato anion or the enolate anion of a β-dicarbonyl-containing compound, or an acetylacetato anion derived from a β-keto ester and when r1≧2, the symbols L1 are identical or different, with the supplementary condition that when the symbol M represents boron, copper or bismuth then the symbol L1 is not acetylacetonate;
the symbol L2 represents an anionic ligand which is different from L1 and when r2≧2, the symbols L2 are identical or different;
and
the symbol Y represents a neutral ligand and when x≧2, the symbols Y are identical or different;
[Fe(L3)r3(L4)r4(Y′)x′] (2)
in which:
r3≧1;
r4≧0 and x′≧0;
the symbol L3 represents a ligand which is a β-ketoesterato anion or the enolate anion of a β-keto ester compound and when r3≧2, the symbols L3 are identical or different;
the symbol L4 represents an anionic ligand which is different from L3 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different;
and
[Fe(L5)r5(L4)r4(Y′)x′] (3)
in which:
r5≧1;
r4≧0 and x′≧0;
the symbol L5 represents a ligand which is a β-diketonato anion selected from the group constituted by:
3,5-heptanedionato, 2,6-dimethyl-3,5-heptanedionato and 2,2,6,6-tetramethyl-3,5-heptanedionato and when r5≧2, the symbols L5 are identical or different;
the symbol L4 represents an anionic ligand which is different from L5 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different.

24 more elements

A two-component system that is a precursor of an organopolysiloxane composition comprising:

at least one polyorganosiloxane oil C capable of crosslinking via polycondensation into an elastomer;
at least one crosslinking agent D;
optionally at least one adhesion promoter E;
and
optionally at least one siliceous, organic and/or non-siliceous mineral filler F, and that is vulcanizable to a silicone elastomer via a polycondensation reaction and wherein said system is in two separate parts P1 and P2 intended to be mixed in order to form said composition, and wherein one of said parts comprises a metal complex or salt A as a catalyst for the polycondensation reaction of organopolysiloxanes and the crosslinking agent D, whilst the other part is free of said catalysts and said crosslinking agent and comprises:
per 100 parts by weight of the polyorganosiloxane oil(s) C capable of crosslinking via polycondensation into an elastomer;
from 0.001 to 10 part(s) by weight of water;
wherein the metal complex or salt A is formula (1), (2) or (3) below:
[M (L1)r1(L2)r2(Y)x] (1)
in which:
r1≧1, r2≧0 and x≧0;
the symbol M represents a metal selected from the group consisting of:
copper, silver, boron, scandium, cerium, ytterbium, bismuth, molybdenum, germanium and manganese;
the symbol L1 represents a ligand which is a β-dicarbonylato anion or the enolate anion of a β-dicarbonyl-containing compound, or an acetylacetato anion derived from a β-keto ester and when r1≧2, the symbols L1 are identical or different, with the supplementary condition that when the symbol M represents boron, copper or bismuth then the symbol L1 is not acetylacetonate;
the symbol L2 represents an anionic ligand which is different from L1 and when r2≧2, the symbols L2 are identical or different;
and
the symbol Y represents a neutral ligand and when x≧2, the symbols Y are identical or different;
[Fe (L3)r3 (L4)r4(Y′)x′] (2)
in which:
r3≧1;
r4≧0 and x′≧0;
the symbol L3 represents a ligand which is a β-ketoesterato anion or the enolate anion of a β-keto ester compound and when r3≧2, the symbols L3 are identical or different;
the symbol L4 represents an anionic ligand which is different from L3 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different;
and
[Fe (L5)r5 (L4)r4(Y′)x′] (3)
in which:
r5≧1;
r4≧0 and x′≧0;
the symbol L5 represents a ligand which is a β-diketonato anion selected from the group constituted by:
3,5-heptanedionato, 2,6-dimethyl-3,5-heptanedionato and 2,2,6,6-tetramethyl-3,5-heptanedionato and when r5≧2, the symbols L5 are identical or different;
the symbol L4 represents an anionic ligand which is different from L5 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different.

32 more elements

A single-component polyorganosiloxane composition that is stable during storage in the absence of moisture and that crosslinks, in the presence of water, into an elastomer, said composition comprising:

at least one crosslinkable linear polyorganopolysiloxane that has functionalized ends of alkoxy, oxime, acyl and/or enoxy type,
a filler;
and
a catalyst of the polycondensation reaction which is a metal complex or salt A of formula (1), (2) or (3) below:
[M(L1)r1(L2)r2(Y)x] (1)
in which:
r1≧1, r2≧0 and x≧0;
the symbol M represents a metal selected from the group consisting of:
copper, silver, boron, scandium, cerium, ytterbium, bismuth, molybdenum, germanium and manganese;
the symbol L1 represents a ligand which is a β-dicarbonylato anion or the enolate anion of a β-dicarbonyl-containing compound, or an acetylacetato anion derived from a β-keto ester and when r1≧2, the symbols L1 are identical or different, with the supplementary condition that when the symbol M represents boron, copper or bismuth then the symbol L1 is not acetylacetonate;
the symbol L2 represents an anionic ligand which is different from L1 and when r2≧2, the symbols L2 are identical or different;
and
the symbol Y represents a neutral ligand and when x≧2, the symbols Y are identical or different;
[Fe (L3)r3(L4)r4(Y′)x′] (2)
in which:
r3≧1;
r4≧0 and x′≧0;
the symbol L3 represents a ligand which is a β-ketoesterato anion or the enolate anion of a β-keto ester compound and when r3≧2, the symbols L3 are identical or different;
the symbol L4 represents an anionic ligand which is different from L3 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different;
and
[Fe (L5)r5(L4)r4(Y′)x′] (3)
in which:
r5≧1;
r4≧0 and x′≧0;
the symbol L5 represents a ligand which is a β-diketonato anion selected from the group constituted by:
3,5-heptanedionato, 2,6-dimethyl-3,5-heptanedionato and 2,2,6,6-tetramethyl-3,5-heptanedionato and when r5≧2, the symbols L5 are identical or different;
the symbol L4 represents an anionic ligand which is different from L5 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different.

28 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/809,538Filed 18 Dec 2008
Priority: FR 07 0892420 Dec 2007
Published: US 2011/0040034 A117 Feb 2011
Granted: 11 Jun 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C08K 5/0091
Use of organic ingredients: complexes with metal-heteroatom-bonds
B01J 31/2234
At least two oxygen atoms present in one at least bidentate or bridging ligand: beta-dicarbonyl ligands, e.g. acetylacetonates
B01J 2531/16
Complexes comprising metals of Group I as the central metal: copper
B01J 2531/17
Complexes comprising metals of Group I as the central metal: silver

Family

US 2011/0040034 A1Pre-grant publication · published 17 Feb 2011
US 8,461,283 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

[M(L1)r1(L2)r2(Y)x] (1)
in which:
r1≧1, r2≧0 and x≧0;
the symbol M represents a metal selected from the group consisting of:
copper, silver, boron, scandium, cerium, ytterbium, bismuth, molybdenum, germanium and manganese;
the symbol L1 represents a ligand which is a β-dicarbonylato anion or the enolate anion of a β-dicarbonyl-containing compound, or an acetylacetato anion derived from a β-keto ester and when r1≧2, the symbols L1 are identical or different, with the supplementary condition that when the symbol M represents boron, copper or bismuth then the symbol L1 is not acetylacetonate;
the symbol L2 represents an anionic ligand which is different from L1 and when r2≧2, the symbols L2 are identical or different;
and
the symbol Y represents a neutral ligand and when x≧2, the symbols Y are identical or different;
[Fe(L3)r3(L4)r4(Y′)x′] (2)
in which:
r3≧1;
r4≧0 and x′≧0;
the symbol L3 represents a ligand which is a β-ketoesterato anion or the enolate anion of a β-keto ester compound and when r3≧2, the symbols L3 are identical or different;
the symbol L4 represents an anionic ligand which is different from L3 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different;
and
[Fe(L5)r5(L4)r4(Y′)x′] (3)
in which:
r5≧1;
r4≧0 and x′≧0;
the symbol L5 represents a ligand which is a β-diketonato anion selected from the group constituted by:
3,5-heptanedionato, 2,6-dimethyl-3,5-heptanedionato and 2,2,6,6-tetramethyl-3,5-heptanedionato and when r5≧2, the symbols L5 are identical or different;
the symbol L4 represents an anionic ligand which is different from L5 and when r4≧2, the symbols L4 are identical or different;
and
the symbol Y′ represents a neutral ligand and when x′≧2, the symbols Y′ are identical or different.

24 more elements

Facts

Application

12/809,538Filed 18 Dec 2008

Priority

FR 07 0892420 Dec 2007

Published

US 2011/0040034 A117 Feb 2011

Granted

11 Jun 2013

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C08K 5/0091
Use of organic ingredients: complexes with metal-heteroatom-bonds
B01J 31/2234
At least two oxygen atoms present in one at least bidentate or bridging ligand: beta-dicarbonyl ligands, e.g. acetylacetonates
B01J 2531/16
Complexes comprising metals of Group I as the central metal: copper
B01J 2531/17
Complexes comprising metals of Group I as the central metal: silver