US 8,283,422 B2Granted

Polyethersiloxanes carrying alkoxysilyl groups and method for production thereof

AssigneeEvonik Goldschmidt GmbH

InventorsFrank Schubert, Frauke Henning, Wilfried Knott

Life of this patent

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Abstract

Alkoxysilyl-functional polyether-siloxanes and processes for preparing them by noble metal-catalysed SiC coupling of hydrogensiloxanes having SiH groups with unsaturated polyethers bearing alkoxysilyl groups or by alkoxylation of polyethersiloxanes or polysiloxanes by means of epoxy-functional alkoxysilanes in the presence of double metal cyanide catalysts.

Claims20

Dependent claims

An alkoxysilyl-functional polyether-siloxane or a mixture of such polyether-siloxanes having the Formula (I) or a mixture of such polyether-siloxanes, the Formula (I) being:

where X is a linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radical which has from 1 to 20 carbon atoms and may, if desired, contain heteroatoms;
where X1 is, as desired, X, X2 or X3;
where X2 is an OH-functional, if desired, ester- or carbonate-modified polyoxyalkylene radical bearing alkoxysilyl groups and having the Formula (Ia);
where X3 is a terminally etherified polyoxyalkylene radical of the Formula (Ib);
where R13 is, as desired, an alkyl group having from 1 to 18 carbon atoms, or a polyoxyalkylene radical terminally esterfied with a monofunctional carboxylic acid and having the Formula (Ic);
where R14 is a saturated or monounsaturated or polyunsaturated, either linear or branched, aliphatic or aromatic hydrocarbon radical which has from 1 to 30 carbon atoms and may in turn bear OH groups;
where X4 corresponds either to X1 or the fragment of the Formula (Id);
where k, k1, and k2 are each, independently of one another, integers from 0 to 500;
where l3, l4, l5, l6, l7 and l8 are each, independently of one another, an integer from 0 to 60;
and
where o is an integer from 0 to 10;
with the proviso that;
X1 is at least once identical to X2 if the sum of l3, l5 and l7 is zero;
and
the sum of l3, l5 and l7 is at least 1 when X1 is not identical to X2;
where a is an integer from 1 to 3;
where b is an integer from 0 to 2;
where the sum of a and b is 3;
where c is an integer from 0 to 24;
where c1 is an integer from 0 to 24;
where d is an integer from 1 to 500;
where e is an integer from 0 to 5000;
where n is an integer from 2 to 8;
and
where f, g, h, i, and j are each an integer from 0 to 500;
with the proviso that the fragments having the indices d to j can be freely permutated among one another, i.e. can be exchanged with one another in the sequence within the polyether chain, and the various monomer units of the fragments having the indices d to j can be arranged in blocks or else can be distributed randomly;
and
with the proviso that the fragments having the indices k, k1, k2, l3, l4, l5, l6, l7, l8 and o can be permutated freely among one another, i.e. can be exchanged with one another within the siloxane chain and can, as desired, be randomly distributed or arranged in blocks;
where R represents one or more identical or different radicals selected from among linear or branched, saturated, monounsaturated or polyunsaturated alkyl radicals having from 1 to 20 carbon atoms or haloalkyl groups having from 1 to 20 carbon atoms;
and
where R2 or R3, and also R5 or R6 are identical or are each, independently of one another, H or a saturated or, if desired, monounsaturated or polyunsaturated, also further substituted, if desired, monovalent or polyvalent hydrocarbon radical, where the radicals R5 and R6 are each a monovalent hydrocarbon radical and the hydrocarbon radical can be cycloaliphatically bridged via the fragment Y, where Y can also be absent or else is a methylene bridge having 1 or 2 methylene units;
if Y is absent, R2 or R3 are each, independently of one another, a linear or branched radical which has from 1 to 20 carbon atoms and may be further substituted and bear functional groups;
where R4 is a linear or branched alkyl radical which has from 1 to 18 carbon atoms and can be bound to an aromatic or cycloaliphatic radical;
and
where R7 and R8 are, independently of one another, either hydrogen, alkyl, alkoxy, aryl or aralkyl groups;
where R9, R10, R11, and R12 are, independently of one another, either hydrogen, alkyl, alkenyl, alkoxy, aryl, or aralkyl groups, where the hydrocarbon radical can be cycloaliphatically or aromatically bridged via the fragment Z and Z can be either a divalent alkylene radical or an alkenylene radical.

33 more elements

A linear polyether-siloxane-polyether triblock copolymer of the Formula (II) in which the polyether chains having alkoxysilyl groups are bound via an Si—O—C linkage to the siloxane body, the Formula (II) being:

where R′ corresponds to one or more identical or different, linear or branched, saturated, monounsaturated or polyunsaturated alkyl radicals having from 1 to 20 carbon atoms;
where m is an integer from 0 to 5000;
and
where X7 corresponds to the polyether fragment of the Formula (IIa):
where a is an integer from 1 to 3;
where b is an integer from 0 to 2;
where the sum of a and b is 3;
where c is an integer from 0 to 24;
where d is an integer from 1 to 500;
where e is an integer from 0 to 5000;
where n is an integer from 2 to 8;
and
where f, g, h, i, and j are each an integer from 0 to 500;
with the proviso that the fragments having the indices d to j can be freely permutated among one another, i.e. can be exchanged with one another in the sequence within the polyether chain, and the various monomer units of the fragments having the indices d to j can be arranged in blocks or else can be distributed randomly;
where R represents one or more identical or different radicals selected from among linear or branched, saturated, monounsaturated or polyunsaturated alkyl radicals having from 1 to 20 carbon atoms or haloalkyl groups having from 1 to 20 carbon atoms;
and
where R2 or R3, and also R5 or R6 are identical or are each, independently of one another, H or a saturated or, if desired, monounsaturated or polyunsaturated, also further substituted, if desired, monovalent or polyvalent hydrocarbon radical, where the radicals R5 and R6 are each a monovalent hydrocarbon radical and the hydrocarbon radical can be cycloaliphatically bridged via the fragment Y, where Y can also be absent or else is a methylene bridge having 1 or 2 methylene units;
if Y is absent, R2 or R3 are each, independently of one another, a linear or branched radical which has from 1 to 20 carbon atoms and may be further substituted and bear functional groups;
where R4 is a linear or branched alkyl radical which has from 1 to 18 carbon atoms and can be bound to an aromatic or cycloaliphatic radical;
and
where R7 and R8 are, independently of one another, either hydrogen, alkyl, alkoxy, aryl or aralkyl groups;
where R9, R10, R11, and R12 are, independently of one another, either hydrogen, alkyl, alkenyl, alkoxy, aryl, or aralkyl groups, where the hydrocarbon radical can be cycloaliphatically or aromatically bridged via the fragment Z and Z can be either a divalent alkylene radical or an alkenylene radical.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/132,734Filed 5 Nov 2009
Priority: DE 10 2008 044 3735 Dec 2008
Published: US 2011/0245412 A16 Oct 2011
Granted: 9 Oct 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C08G 77/18
Containing silicon bound to oxygen-containing groups: to alkoxy or aryloxy groups
C08G 77/46
Block-or graft-polymers containing polysiloxane sequences: containing polyether sequences
C08L 83/12
Block- or graft-copolymers containing polysiloxane sequences: containing polyether sequences
C08G
Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds

Family

US 2011/0245412 A1Pre-grant publication · published 6 Oct 2011
US 8,283,422 B2This patent

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

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Abstract

An alkoxysilyl-functional polyether-siloxane or a mixture of such polyether-siloxanes having the Formula (I) or a mixture of such polyether-siloxanes, the Formula (I) being:

where X is a linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radical which has from 1 to 20 carbon atoms and may, if desired, contain heteroatoms;
where X1 is, as desired, X, X2 or X3;
where X2 is an OH-functional, if desired, ester- or carbonate-modified polyoxyalkylene radical bearing alkoxysilyl groups and having the Formula (Ia);
where X3 is a terminally etherified polyoxyalkylene radical of the Formula (Ib);
where R13 is, as desired, an alkyl group having from 1 to 18 carbon atoms, or a polyoxyalkylene radical terminally esterfied with a monofunctional carboxylic acid and having the Formula (Ic);
where R14 is a saturated or monounsaturated or polyunsaturated, either linear or branched, aliphatic or aromatic hydrocarbon radical which has from 1 to 30 carbon atoms and may in turn bear OH groups;
where X4 corresponds either to X1 or the fragment of the Formula (Id);
where k, k1, and k2 are each, independently of one another, integers from 0 to 500;
where l3, l4, l5, l6, l7 and l8 are each, independently of one another, an integer from 0 to 60;
and
where o is an integer from 0 to 10;
with the proviso that;
X1 is at least once identical to X2 if the sum of l3, l5 and l7 is zero;
and
the sum of l3, l5 and l7 is at least 1 when X1 is not identical to X2;
where a is an integer from 1 to 3;
where b is an integer from 0 to 2;
where the sum of a and b is 3;
where c is an integer from 0 to 24;
where c1 is an integer from 0 to 24;
where d is an integer from 1 to 500;
where e is an integer from 0 to 5000;
where n is an integer from 2 to 8;
and
where f, g, h, i, and j are each an integer from 0 to 500;
with the proviso that the fragments having the indices d to j can be freely permutated among one another, i.e. can be exchanged with one another in the sequence within the polyether chain, and the various monomer units of the fragments having the indices d to j can be arranged in blocks or else can be distributed randomly;
and
with the proviso that the fragments having the indices k, k1, k2, l3, l4, l5, l6, l7, l8 and o can be permutated freely among one another, i.e. can be exchanged with one another within the siloxane chain and can, as desired, be randomly distributed or arranged in blocks;
where R represents one or more identical or different radicals selected from among linear or branched, saturated, monounsaturated or polyunsaturated alkyl radicals having from 1 to 20 carbon atoms or haloalkyl groups having from 1 to 20 carbon atoms;
and
where R2 or R3, and also R5 or R6 are identical or are each, independently of one another, H or a saturated or, if desired, monounsaturated or polyunsaturated, also further substituted, if desired, monovalent or polyvalent hydrocarbon radical, where the radicals R5 and R6 are each a monovalent hydrocarbon radical and the hydrocarbon radical can be cycloaliphatically bridged via the fragment Y, where Y can also be absent or else is a methylene bridge having 1 or 2 methylene units;
if Y is absent, R2 or R3 are each, independently of one another, a linear or branched radical which has from 1 to 20 carbon atoms and may be further substituted and bear functional groups;
where R4 is a linear or branched alkyl radical which has from 1 to 18 carbon atoms and can be bound to an aromatic or cycloaliphatic radical;
and
where R7 and R8 are, independently of one another, either hydrogen, alkyl, alkoxy, aryl or aralkyl groups;
where R9, R10, R11, and R12 are, independently of one another, either hydrogen, alkyl, alkenyl, alkoxy, aryl, or aralkyl groups, where the hydrocarbon radical can be cycloaliphatically or aromatically bridged via the fragment Z and Z can be either a divalent alkylene radical or an alkenylene radical.

33 more elements

Facts

Application

13/132,734Filed 5 Nov 2009

Priority

DE 10 2008 044 3735 Dec 2008

Published

US 2011/0245412 A16 Oct 2011

Granted

9 Oct 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C08G 77/18
Containing silicon bound to oxygen-containing groups: to alkoxy or aryloxy groups
C08G 77/46
Block-or graft-polymers containing polysiloxane sequences: containing polyether sequences
C08L 83/12
Block- or graft-copolymers containing polysiloxane sequences: containing polyether sequences
C08G
Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds