Polyglycol ether-free sulphosuccinates based on polyglycerol partial esters and use thereof
View Patent ↗The invention relates to polyglycol ether-free, polyglycerol partial ester-based sulphosuccinates, the preparation thereof, and the use of these in cosmetic formulations and also in cleaning compositions in the industrial and domestic sector and formulations comprising these sulphosuccinates.
1. A polyglycerol partial ester-based sulphosuccinate of general formula I
wherein
R 1 , R 2 , R 3 =independently of one another, identical or different H, R 4 or R 5 ,
R 4 =a saturated or partially unsaturated acyl radical containing 6-22 carbon atoms which can be substituted by hydroxyl groups,
R 5 is selected from
sulphosuccinic acid radicals of the formula IIa or IIb
and
sulphomethylsuccinic acid radicals of the formula IIc or IId
where
R 6 , R 7 , R 8 , R 9 =independently of one another, identical or different H, an alkali metal or ½ alkaline earth metal or an ammonium group
n=2 to 16,
and wherein
on statistical average, per molecule of the general formula I, 0.2 to 0.8radicals R 4 and
on statistical average, per molecule of the general formula I 0.3 to 6 radicals R 5 are present.
2. The sulphosuccinate according to claim 1 , wherein R 1 , R 2 , R 3 ═H and wherein on statistical average, said sulphosuccinate has a weight ratio of carboxylic acid R 4 OH to polyglycerol basic backbone of 0.10:1 to 0.50:1.
3. The sulphosuccinate according to claim 1 , wherein said sulphosuccinate has an average degree of polymerization n of 2 to 11.
4. The sulphosuccinate according to claim 1 , wherein R 4 =an acyl radical of a fatty acid selected from the group consisting of oenanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, undecylenic acid, myristoleic acid, palmitoleic acid, petroselic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, calendic acid, punicic acid, α-elaeostearic acid, β-elaeostearic acid, and mixtures thereof.
5. The sulphosuccinate according to claim 1 , wherein R is selected from sulphosuccinic acid radicals of the formula IIa or IIb.
6. The sulphosuccinates according to claim 1 , wherein R 5 is selected from sulphomethylsuccinic acid radicals of the formula IIc or IId.
7. The sulphosuccinate according to claim 1 , wherein R 4 =the acyl radical of a natural fatty acid selected from the group consisting of caprylic acid, capric acid, lauric acid, and coconut fatty acid mixtures and R 5 is selected from sulphosuccinic acid radicals of the formula IIa or IIb.
8. A process for the preparation of a polyglycerol partial ester-based sulphosuccinate comprising the process steps:
A) reacting a polyglycerol having a degree of polymerization of 2 to 16 with 20 to 80 mol per cent, based on the polyglycerol, of one or more saturated or partially unsaturated carboxylic acids containing 6-22 carbon atoms which may be substituted by hydroxyl groups,
B) selecting from at least one of the process steps
B1) reacting with 30-600 mol per cent of maleic anhydride and/or itaconic anhydride, based on the polyglycerol, and
B2) reacting with 30-600 mol per cent of itaconic acid, based on the polyglycerol,
C) sulphonating with alkali metal, alkaline earth metal and/or ammonium sulphite salts and optionally
D) purification of the sulphosuccinates based on polyglycerol partial esters.
9. The process according to claim 8 , wherein in process step A), the polyglycerol is reacted with 10-50 per cent by weight, based on the polyglycerol, of at least one carboxylic acid.
10. The process according to claim 8 , wherein, in process step A), the polyglycerol has an average degree of polymerization n of 2-11.
11. The process according to claim 8 , wherein, in process step A), fatty acids selected from the group consisting of caproic acid, oenanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, undecylenic acid, myristoleic acid, palmitoleic acid, petroselic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, calendic acid, punicic acid, α-elaeostearic acid and β-elaeostearic acid, and mixtures of thereofare used.
12. The process according to claim 8 , wherein, in process step B), maleic anhydride or itaconic anhydride is used.
13. The process according to claim 8 , wherein process step B2) is carried out with process step A) as a one-pot synthesis.
14. The process according to claim 8 , wherein, in process step A), at least one carboxylic acid selected from caprylic acid, capric acid, lauric acid and coconut fatty acid mixtures and, in process step B), maleic anhydride according to B1) are used.
15. A formulation comprising at least one sulphosuccinate according to claim 1 .
16. The formulation according to claim 15 , wherein said formulation is essentially sulphate-free and essentially free from alkoxylated compounds.
17. The formulation according to claim 15 , wherein said formulation is essentially polyglycol ether-free and essentially free from alkoxylated compounds.
18. The formulation according to claim 15 , wherein said formulation is essentially sulphate-free, essentially polyglycol ether-free and essentially free from alkoxylated compounds.