Hydrophilic/lipophilic modified polysiloxanes as emsulsifiers

Patent metadata

Field	Value
Publication number	US-9340650-B2
Application number	US-201013511464-A
Country	US
Kind code	B2
Filing date	Nov 24, 2010
Priority date	Nov 24, 2009
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The invention concerns polysiloxane compounds as W/O-emulsifiers, in textile softeners, antifoams, foam stabilizers and agriculture chemicals, in particular as W/O-emulsifiers for cosmetic uses.

First claim

The invention claimed is:

1. Polysiloxane compounds of the formula:
[M a D b T c Q d ] e   (I)

wherein
M=R 3 SiO 1/2 ,
D=R 2 SiO 2/2 ,
T=RSiO 3/2 ,
Q=SiO 4/2 ,
with
a=1-10
b=0-1000
c=0-1
d=0-1
e=1-10
wherein
R=is an organic group,
with the requirement that R comprises hydrophilic residues R 91 and lipophilic residues R 92
wherein
R 91 is selected from the group consisting of:
R 11 =—Z-(A-E 1 ) y , wherein
Z=a bivalent or trivalent straight-chained, cyclic or branched, saturated or unsaturated C 2 to C 20 -hydrocarbon residue, which can comprise one or more groups selected from —O—, —NH—,

 and can be substituted by one or more OH groups,
A is a bivalent residue which is selected from the group consisting of:

wherein y=1 or 2,
E 1 is selected from the group consisting of:
E 22 =—O—C(O)—R 22 ,
wherein R 22 =a straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with up to 9 carbon atoms, which can comprise one or more groups selected from —O—, —NH—, —NR 3 —, —C(O)—, and is substituted by one or more OH groups, wherein R 3 =a straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with up to 6 carbon atoms,
E 31 =

wherein x=1-4, and
E 51 =—NR 41 R 51 , wherein
R 41 and R 51 are the same or different and selected from the group consisting of hydrogen and a straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with up to 9 carbon atoms, which can comprise one or more groups selected from —O—, —NH—, —NR 3 —, wherein R 3 , as defined above, can comprise —C(O)— and can be substituted by one or more OH and/or H 2 N groups,
R 61 =—Z-E 22 , and
R 71 =—Z-E 61 , wherein E 61 =—NH—C(O)—R 41 , and

R 92 is selected from the group consisting of:
R 12 =—Z-(A-E 2 ) y , wherein
E 2 is selected from the group consisting of:
E 23 =—O—C(O)—R 23 ,
wherein R 23 =a straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with 10 to 50 carbon atoms, which can comprise one or more groups selected from —O—, —NH—, —NR 3 —, —C(O)—, and can be substituted by one or more OH groups, wherein R 3 =a straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with up to 6 carbon atoms,
E 32 =

and x=1-4, and
E 52 =—NR 42 R 52 , wherein
R 42 and R 52 are the same or different and are selected from the group consisting of a hydrogen and straight-chained, cyclic or branched, saturated or unsaturated hydrocarbon residue with 10 to 30 carbon atoms, which can comprise one or more groups selected from —O—, —NH—, —NR 3 —, —C(O)—, and can be substituted by one or more OH— and/or H 2 N groups, and

R 62 =—Z-E 23 , and
R 72 =—Z-E 62 , wherein E 62 =—NH—C(O)—R 42 .

2. Polysiloxane compounds according to claim 1 , wherein
the hydrophilic residues R 91 have a logP (25° C.) of <0.5 and
the lipophilic residues R 92 have a logP (25° C.) of ≧0.5 ,
determined on the basis of the corresponding compounds H—R 91 and H—R 92- .

3. Polysiloxane compounds according to claim 1 , wherein
R=methyl,
Z=is selected from the group consisting of —CH 2 CH 2 CH 2 —O—CH 2 —, —CH 2 CH 2 CH 2 —,

wherein z=1 to 4,
wherein * denotes a bond,
—CH═CH 2 CH 2 —, —CH═CH 2 CH 2 CH 2 —,

 wherein the bond to the silicon takes place at the 2-position, and
x=1.

4. The process for the production of the polysiloxane compounds according to claim 1 , wherein
(a) an epoxy-functional polysiloxane is reacted with one or more carboxylic acids and subsequently with primary or secondary amines, if necessary,
(b) an epoxy-functional polysiloxane is reacted with one or more carboxylic acids and carboxylic acid anhydrides, wherein carboxylic acid anhydrides are partially esterified by adding mono or multivalent alcohols, and subsequently also reacted with primary or secondary amines,
(c) a SiH-functional polysiloxane is reacted with
(i) one or more mono-functional olefinically or acetylenically unsaturated ethers of glycerine or of glycerine oligomers, at least one hydroxyl group of which is esterified, and
(ii) one or more esters of fatty acids with unsaturated alcohols, or

(d) amino-functional polysiloxanes are reacted with carboxylic acids or with epoxy-functional compounds.

5. The process according to claim 4 , wherein the unsaturated alcohols are selected from the group consisting of monols; diols; alkenols; alkynols; CH 2 ═CHCH 2 OH; CH 2 ═CHCH 2 CH 2 OH; CH 2 ═CHCH 2 CH 2 CH 2 CH 2 OH; CH≡CCH 2 OH; HOCH 2 C≡CCH 2 OH; HOCH 2 CH═CHCH 2 OH; CH≡CHCH 2 CH 2 CH 2 CH 2 OH; hexynediols; HOCH 2 CH 2 C≡CCH 2 CH 2 OH; ethylenoxide-free poly(alkoxylates) of alkenols or alkynols, and ethylenoxide-free (poly)propoxylates of alkenols or alkynols.

6. The process according to claim 4 , wherein the fatty acids are monocarboxylic acids which lack hydrosilylated groups selected from the group consisting of acetic acid, caprionic acid, 2-ethyl caprionic acid, lauric acid, tetradecenoic acid, capriodecenoic acid, octadecenoic acid, oleic acid, linoleic aci,d linolenic acid and elaidic acid.

7. An emulsifier comprising the polysiloxane polymers according to claim 1 .

8. A cosmetic formulation comprising the polysiloxane polymers according to claim 1 .

9. A sun screen formulation comprising the cosmetic formulation of claim 8 .

10. A defoaming composition comprising the polysiloxane polymers according to claim 1 .

11. A foam stabilizer for polyurethane foams comprising the polysiloxane polymers according to claim 1 .

12. An agriculture composition comprising the polysiloxane polymers according to claim 1 .

13. Water in oil emulsions comprising the polysiloxane polymers of claim 1 .

Assignees

• Wagner Roland
• Simon Walter
• Kropfgans Martin
• Nienstedt Sabine
• Schnering Albert
• Streicher Katharina
• Sockel Karl-Heinz
• Maass Sebastian
• Momentive Performance Mat Inc

Inventors

• Wagner Roland
• Simon Walter
• Kropfgans Martin
• Nienstedt Sabine
• Schnering Albert
• Streicher Katharina
• Sockel Karl-Heinz
• Maass Sebastian

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• C08L83/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen · CPC title

• C08L83/12

  containing polyether sequences · CPC title

• C08G77/388 Primary

  containing nitrogen · CPC title

• C08G77/14 Primary

  containing silicon bound to oxygen-containing groups · CPC title