IP Library Granted Patent US 8,772,423
Granted Patent B2
US 8,772,423 · App. 13/322,475 · Granted Jul 8, 2014

Emulsions based on hydroxyl compounds bearing silyl groups

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Quick Facts
Patent No.
US 8,772,423
App. No.
13/322,475
Granted
Jul 8, 2014
Kind
B2
Abstract

The invention relates to emulsions containing hydroxyl compound bearing silyl groups, to the production and to the use thereof.

Claims (92)

1. A stable, hydrolysis-resistant aqueous emulsion comprising:

silyl-functionalized polyethers, and optionally silyl-functionalized polyethersiloxanes, having in each case at least one nonterminal silyl function in the molecule;

wherein the silyl-functionalized polyethers are compounds of the formula (1):

where:

a is an integer from 1 to 3;

b is an integer from 0 to 2;

the sum of a and b is 3;

c is an integer from 0 to 22:

d is an integer from 1 to 1000;

e is an integer from 0 to 10,000;

f is an integer from 0 to 1000;

g is an integer from 0 to 1000; and

h, i, and j are integers from 0 to 500;

with the proviso that the fragments with the indices d to j are freely permutable with one another so as to be interchangeable with one another in the sequence within the polyether chain; and

where:

n is an integer between 2 and 8;

R represents one or more identical or different radicals selected from linear or branched, saturated, singularly or multiply unsaturated alkyl radicals having 1 to 20 carbon atoms or haloalkyl groups having 1 to 20 carbon atoms;

R 1 :

is a radical, or a polyether radical selected from the group consisting of alkoxy, arylalkoxy, and alkylarylalkoxy radicals, in which the carbon chain is optionally interrupted by oxygen atoms; or

is an optionally singularly or multiply fused aromatic aryloxy group; or

is a silicon-containing compound or a siloxane radical or (poly)siloxane radical which is optionally alkyl- and/or aryl-group-substituted;

R 2 and R 3 , identically or else independently of one another, are each:

H; or

a saturated or optionally singularly or multiply unsaturated, also further-substituted, optionally monovalent or polyvalent hydrocarbon radical, where R 2 and R 3 are optionally bridged cycloaliphatically via the fragment Y;

Y:

is not be present; or

is a methylene bridge having 1 or 2 methylene units;

where if Y is not present then R 2 or R 3 independently of one another is a linear or branched radical having 1 to 20 carbon atoms;

R 4 :

is a linear or branched alkyl radical of 1 to 24 carbon atoms; or

is an aromatic or cycloaliphatic radical which may optionally in turn carry alkyl groups;

R 5 and R 6 identically or else independently of one another, are each:

H; or

a saturated or optionally singular or multiply unsaturated, also further-substituted, monovalent hydrocarbon radical;

R 7 and R 8 are, independently of one another, alternatively:

hydrogen; or

selected from the group consisting of alkyl, alkoxy, aryl, and aralkyl groups; and

R 9 and R 12 are each, independently of one another, alternatively:

hydrogen; or

an alkyl, alkenyl, alkoxy, aryl, or aralkyl group;

R 10 and R 11 are each, independently of one another, alternatively:

hydrogen; or

an alkyl, alkenyl, alkoxy, aryl, or aralkyl group, which is optionally bridged cycloaliphatically or aromatically via the fragment Z; and

Z:

is not be present; or

is a divalent alkylene radical or an alkenylene radical.

2. The emulsion of claim 1 ;

wherein compositions are present in which the sum of the indices (a) plus (b) in formula (1) is on average less than 3, since some of the OR groups are replaced by silyl polyether groups as a result of transesterification reactions.

3. The emulsion of claim 1 ;

wherein R 1 is a (poly)siloxane radical.

4. The emulsion of claim 3 , further comprising:

an alkoxysilyl-functional polyethersiloxane of formula (3) and mixtures thereof:

where:

X is a linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radical having 1 to 20 C atoms, which may comprise heteroatoms;

X 1 is alternatively X, X 2 , or X 3 ;

X 2 is an OH-functional polyoxyalkylene radical of the formula (3a) which carries alkoxysilyl groups and which are optionally ester- or carbonate-modified:

X 3 is a terminally etherified polyoxyalkylene radical of the formula (3b):

R, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 are defined in claim 1 ;

R 13 is alternatively;

an alkyl group having 1 to 18 C atoms; or

a polyoxyalkylene radical of the formula (3c) which is terminally esterified with a monofunctional carboxylic acid:

 where;

 R 14 is a saturated or a singularly or multiply unsaturated, either linear or branched, aliphatic or aromatic hydrocarbon radical having 1-30 carbon atoms, which in turn may carry OH groups and

X 4 is either X 1 or the fragment of the formula (3d);

where:

k, k 1 , and k 2 independently of one another are integers from 0 to 500;

l 3 , l 4 , l 5 , l 6 , l 7 , and l 8 independently of one another are integers from 0 to 60; and

o is an integer from 0 to 10;

with the proviso:

that X 1 is at least once X 2 if the sum of l 3 , l 5 , and l 7 is zero; and

that the sum of l 3 , l 5 , and l 7 is at least one if X 1 is other than X 2 ;

where:

a, b, c, h, i, j, and n are as defined in claim 1 ;

c 1 is an integer from 0 to 24;

d is an integer from 1 to 500;

e is an integer from 0 to 5000; and

f and g are each integers from 0 to 500;

with the proviso that the fragments with the indices d to j are freely permutable with one another, being interchangeable with one another in the sequence within the polyether chain, where the various monomer units of the fragments with the index numbers d to j may be constructed blockwise with one another or else may be subject to a statistical distribution; and

with the proviso that the fragments with the indices k, k 1 , k 2 , l 3 , l 4 , l 5 , l 6 , l 7 , l 8 , and o are freely permutable with one another, being interchangeable with one another within the siloxane chain, and may be present alternatively with statistical distribution or with block-like sequencing.

5. The emulsion of claim 1 ;

wherein linear polyether-siloxane-polyether triblock copolymers of the formula (5) are present in which the polyether chains furnished with alkoxysilyl groups are attached via an Si—O—C linkage to the siloxane structure, formula (5) being:

where:

R′ corresponds to one or more identical or different linear or branched, saturated, singularly or multiply unsaturated alkyl radicals having 1 to 20 carbon atoms;

m is an integer from 0 to 5000; and

X 7 corresponds to the polyether fragment of the formula (5a);

where the substituents R, R 2 -R 12 , the radicals Y and Z, and the indices a, b, c, d, e, f, g, h, i, j, and n.

6. The emulsion of claim 1 , further comprising:

emulsifiers selected from the group consisting of anionic, nonanionic, cationic, and amphoteric emulsifiers, and mixtures thereof.

7. The emulsion of claim 1 , further comprising:

a compound selected from the groups consisting of catalysts, photolatent bases, additives for modifying the rheological properties, hydrophilic fillers, organofunctional and/or partially soluble and/or water-insoluble silanes and/or siloxanes, auxiliaries, film-formers, antimicrobial and preservative substances, dispersants, defoamers and deaerating agents, dyes, colorants, and pigments, antifreeze agents, fungicides, adhesion promoters and/or reactive diluents, plasticizers and complexing agents, spraying assistants, wetting agents, vitamins, growth substances, hormones and/or fragrances, light stabilizers, free-radical scavengers, UV absorbers, and further stabilizers.

8. A method for the production of paints, inks, release agents, adhesives, cosmetic products, scratch-resistant coatings, architectural preservatives, corrosion inhibitors and/or sealants, for the coating of paper, particles, textile fibers, and glass fibers, for the coating of fillers for paper, for producing antistatic surfaces and/or as starting material for producing rubber parts based on polypropylene oxide, comprising:

utilizing the emulsion of claim 1 as a raw material.

Assignments (2)
MERGER Recorded May 15, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032900/0372 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2011
From: DE GANS, BEREND-JAN, DR.; SCHUBERT, FRANK, DR.; NAUMANN, MATTHIAS, DR.; KNOTT, WILFRIED, DR.; SILBER, STEFAN, DR.
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 027279/0597 →