Amphiphilic organopolysiloxanes having polyester groups and use thereof as emulsifiers or dispersing agents

1. An organopolysiloxane copolymer comprising, on average, at least one polyester group bonded to a siloxane via a spacer and, on average, at least one hydrophilic group bonded to the siloxane via a spacer, of the general formula (I):

in which

each R 1 are identical or different and are alkyl radicals having 1 to 30 carbon atoms or phenyl radicals,

each R 2 independently of one another are R 1 , —A—R 3 or —B—R 4

in which

—A— is a divalent alkyleneoxy group having 3 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

and/or is a divalent polyoxyalkylene group of the general average formula

—R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —

in which

q=1 to 100,

r=0 to 100,

s=0 to 100,

R 5 is a divalent alkyleneoxy group having 1 to 24 carbon atoms, which is optionally branched arid/or can contain double bonds,

R 3 is a polyester radical of the general formula

in which

t is an integer in the range from 2 to 5, and [—(O═C)—S—O—] is a radical of 12-hydroxystearic acid or of ricinoleic acid,

—B— acts as a spacer between siloxane backbone and R 4 ,

R 4 is a hydrophilic radical of the general average formula

-R 6 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —R 7 in which q=1 to 100, r=0 to 100, s=0 to 100, R 6 is a divalent alkylene or alkyleneoxy group having 1 to 24 carbon atoms which is optionally branched and/or can contain double bonds and R 7 is a hydrogen atom, alkyl or acyl radical having 1 to 20 carbon atoms, or

R 4 is one of a polyhydroxyorganyl radical selected from the group consisting of glycerol and polyglycerol, a sugar or sugar derivative radical, a polyvinyl alcohol radical, a carboxylate, sulfate or phosphate radical, an ammonium radical or an amphoteric betaine or an amphoglycinate radical,

a has a value from 1 to 1000, and

b has a value from 0 to 10,

with the proviso that, on statistical average, at least in each case one radical R 2 =—A—R 3 and R 2 =—B—R 4 is present, or in the case where no radical —B—R 4 is present, at least one radical R 2 =—A—R 3 is present in which —A— is a divalent polyoxyalkylene group of the above-described general average formula —R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —.

2. The organopolysiloxane copolymer of claim 1 , wherein b=0 and a=10 to 150.

3. An organopolysiloxane copolymer comprising, on average, at least one polyester group bonded to a siloxane via a spacer and, on average, at least one hydrophilic group bonded to the siloxane via a spacer, of the general formula (I):

in which

each R 1 are identical or different and are alkyl radicals having 1 to 30 carbon atoms or phenyl radicals,

each R 2 independently of one another are R 1 , —A—R 3 or —B—R 4

in which

—A— is a divalent alkyleneoxy group having 3 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

and/or is a divalent polyoxyalkylene group of the general average formula

—R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —

in which

q=1 to 100,

r=0 to 100,

s=0 to 100,

R 5 is a divalent alkyleneoxy group having 1 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

R 3 is a polyester radical of the general formula

in which

t is an integer in the range from 1 to 10, and [—(O═C)—S—O—] is the fragment of a corresponding hydroxycarboxylic acid, HO—(O═C)—S—OH, in which

—S— is an optionally branched and/or double-bond-containing alkylene radical having 5 to 30 carbon atoms, with the proviso that at least 5 carbon atoms are between the carboxyl group [HO—C(O)—] and the hydroxyl group [—OH];

—B— acts as a spacer between siloxane backbone and R 4 ,

R 4 is a radical selected from the group consisting of polyethers, polyglycerol, polyvinyl alcohol, sugar and sugar derivatives,

a has a value from 1 to 1000, and

b has a value from 0 to 10,

with the proviso that, on statistical average, at least in each case one radical R 2 =—A—R 3 and R 2 =—B—R 4 is present, or in the case where no radical —B—R 4 is present, at least one radical R 2 =—A—R 3 is present in which —A— is a divalent polyoxyalkylene group of the above-described general average formula —R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —.

4. The organopolysiloxane copolymer of claim 3 , wherein b=0 and a=10 to 150.

5. A process for the preparation of a compound of general formula (I)

in which

each R 1 are identical or different and are alkyl radicals having 1 to 30 carbon atoms or phenyl radicals,

each R 2 independently of one another are R 1 , —A—R 3 or —B—R 4 in which

—A— is a divalent alkyleneoxy group having 3 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

and/or is a divalent polyoxyalkylene group of the general average formula

—R 5 —(C 2 H 4 O) q (C 3 H 6 O) r —(C 4 H 8 O) s —

in which

q=1 to 100,

r=0 to 100,

s=0 to 100,

R 5 is a divalent alkyleneoxy group having 1 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

R 3 is a polyester radical of the general formula

in which

t is integers in the range from 1 to 10, and [—(O═C)—S—O—] is the fragment of a corresponding hydroxycarboxylic acid

HO—(O═C)—S—OH, in which

—S— is an optionally branched and/or double-bond-containing alkylene radical having 5 to 30 carbon atoms, with the proviso that at least 5 carbon atoms are between the carboxyl group [HO—C(O)—] and the hydroxyl group [—OH];

—B— acts as a spacer between siloxane backbone and R 4 ,

R 4 is a hydrophilic radical of the general average formula —R 6 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —R 7 in which q=1 to 100, r=0 to 100, s=0 to 100, R 6 is a divalent alkylene or alkyleneoxy group having 1 to 24 carbon atoms which is optionally branched and/or can contain double bonds and R 7 is a hydrogen atom, alkyl or acyl radical having 1 to 20 carbon atoms, or

R 4 is one of a polyhydroxyorganyl radical selected from the group consisting of glycerol and polyglycerol, a sugar or sugar derivative radical, a polyvinyl alcohol radical, a carboxylate, sulfate or phosphate radical, an ammonium radical or an amphoteric betaine or amphoglycinate radical,

a has a value from 1 to 1000, and

b has a value from 0 to 10,

with the proviso that, on statistical average, at least in each case one radical R 2 =—A—R 3 and R 2 =—B—R 4 is present, or in the case where no radical —B—R 4 is present, at least one radical R 2 =—A—R 3 is present in which —A— is a divalent polyoxyalkylene group of the above-described general average formula —R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —, which comprises adding on polyester radicals either by hydrosilylation of a polyester carrying a double bond to a polyhydrogensiloxane, or by esterification of an OH-functional polysiloxane with a polyester carrying a free carboxyl group.

6. The method of claim 5 , wherein the fragment [—(O═C)—S—O—] t corresponds to the radical of 12-hydroxystearic acid or of ricinoleic acid and t is between 2 and 5.

7. The method of claim 5 , wherein the hydrophilic radical R 4 is a radical selected from the group consisting of polyethers, polyglycerol, polyvinyl alcohol, sugar and sugar derivatives.

8. The method of claim 5 , wherein b=0 and a=10 to 150.

9. An organopolysiloxane copolymer comprising, on average, at least one polyester group bonded to a siloxane via a spacer and, on average, at least one hydrophilic group bonded to the siloxane via a spacer, of the general formula (I):

in which

each R 1 are identical or different and are alkyl radicals having 1 to 30 carbon atoms or phenyl radicals,

each R 2 independently of one another are R 1 , —A—R 3 or —B—R 4 in which

—A— is a divalent alkyleneoxy group having 3 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

and/or is a divalent polyoxyalkylene group of the general average formula

—R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —

in which

q=1 to 100,

r=0 to 100,

s=0 to 100,

R 5 is a divalent alkyleneoxy group having 1 to 24 carbon atoms, which is optionally branched and/or can contain double bonds,

R 3 is a polyester radical of the general formula

in which

t is an integer in the range from 2 to 5, and [—(O═C)—S—O—] is a radical of 12-hydroxystearic acid or of ricinoleic acid,

—B— acts as a spacer between siloxane backbone and R 4 ,

R 4 is a radical selected from the group consisting of polyethers, polyglycerol, polyvinyl alcohol, sugar and sugar derivatives,

a has a value from 1 to 1000, and

b has a value from 0 to 10,

with the proviso that, on statistical average, at least in each case one radical R 2 =—A—R 3 and R 2 =—B—R 4 is present, or in the case where no radical —B—R 4 is present, at least one radical R 2 =—A—R 3 is present in which —A— is a divalent polyoxyalkylene group of the above-described general average formula —R 5 —(C 2 H 4 O) q —(C 3 H 6 O) r —(C 4 H 8 O) s —.