Esters of oligo-hydroxycarboxylic acids and use thereof

Patent metadata

Field	Value
Publication number	US-10125215-B2
Application number	US-201414895704-A
Country	US
Kind code	B2
Filing date	May 28, 2014
Priority date	Jun 3, 2013
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

Esters of oligo-hydroxycarboxylic acids have the general formula ( ):

wherein at least one of the radicals R 1 , R 4 or R 5 is a linear or branched aliphatic hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds. Cosmetic and pharmaceutical agents contain said esters. These esters are effective as thickeners, in particular for compositions containing surfactants.

First claim

The invention claimed is:

1. A composition comprising a mixture of compounds of the general formula (I):

wherein:
R 1 is hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
R 2 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 4 , —CH 2 —OH and —CH 2 —COOR 4 , where the radicals R 4 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
R 3 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 5 , —CH 2 —OH and —CH 2 —COOR 5 , where the radicals R 5 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
n is on average a value from 0.1 to 100,
m1 and m2, independently of one another, are 0 or 1,
wherein the compounds of general formula (I) have an average degree of oligomerization (p) of n+1, and wherein the compounds of the general formula (I) differ in the degree of oligomerization,
with the proviso that at least one of the radicals R 1 , R 4 or R 5 is a linear or branched aliphatic hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds
obtained by a process in which at least one hydroxycarboxylic acid of the general formula (I.A)

in which
R 2 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 4 , —CH 2 —OH and —CH 2 —COOR 4 , where the radicals R 4 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
R 3 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 5 , —CH 2 —OH and —CH 2 —COOR 5 , where the radicals R 5 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
m1 is 0 or 1,
is reacted in an esterification reaction, where the esterification takes place in the presence of at least one alcohol R 1 —OH, where
R 1 is hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
or the product of the esterification of the hydroxycarboxylic acid(s) (I.A) is then reacted with at least one alcohol R1-OH.

2. The composition according to claim 1 , wherein m1 and m2 have the same meaning.

3. The composition according to claim 1 , wherein the mixture of compounds of the general formula (I) is derived from lactic acid, glycolic acid, malic acid, tartaric acid or mixtures thereof.

4. The composition according to claim 1 , wherein the mixture of compounds of the general formula (I) is selected from compounds of the formula (I.1):

wherein:
R 1 is a linear or branched hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, and
n is on average a value of from 0.1 to 100.

5. The composition according to claim 1 , wherein n is a value from 0.15 to 50.

6. The composition according to claim 1 , wherein at least one of the radicals R 1 , R 4 and R 5 is n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, arachinyl, behenyl, lignocerinyl, melissinyl, isotridecyl, isostearyl, oleyl, linoleyl, linolenyl, and combinations thereof.

7. The composition according to claim 1 , wherein at least one of the radicals R 1 , R 4 and R 5 is derived from linear saturated alcohols having 8 to 18 carbon atoms.

8. The composition according to claim 1 , wherein at least one of the radicals R 1 , R 4 and R 5 is derived from a mixture of linear saturated C 12 -/C 14 -alcohols.

9. A process for preparing the composition of claim 1 comprising a mixture of compounds having the general formula (I):

the process comprising:
reacting at least one hydroxycarboxylic acid of the general formula (I.A):

in an esterification reaction, where the esterification takes place in the presence of at least one alcohol R 1 —OH or the product of the esterification of the hydroxycarboxylic acid(s) (I.A) is then reacted with at least one alcohol R 1 —OH,
wherein
R 1 is hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
the radicals R 2 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 4 , —CH 2 —OH and —CH 2 —COOR 4 , where the radicals R 4 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
the radicals R 3 , independently of one another, are selected from hydrogen, methyl, ethyl, —OH, —COOR 5 , —CH 2 —OH and —CH 2 —COOR 5 , where the radicals R 5 are hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds,
n is on average a value from 0.1 to 100,
m1 and m2, independently of one another, are 0 or 1,
with the proviso that at least one of the radicals R 1 , R 4 or R 5 is a linear or branched aliphatic hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds.

10. A cosmetic or pharmaceutical composition comprising:
a) the composition comprising the mixture of compounds of the general formula (I) according to claim 1 ,
b) at least one cosmetically or pharmaceutically acceptable active ingredient, and
c) optionally at least one cosmetically or pharmaceutically acceptable auxiliary different from the components a) and b).

11. The composition comprising the mixture of compounds of the general formula (I) according to claim 1 , which is effective as a thickener for aqueous surfactant-containing compositions.

12. The composition comprising the mixture of compounds of the general formula (I) according to claim 1 , which is effective as a component for the formulation of one or more of:
cosmetic compositions,
pharmaceutical compositions,
detergents and cleaners,
crop protection compositions,
wetting agents, and
paints, coatings, adhesives, leather-treatment or textile-treatment compositions.

13. The composition according to claim 5 , wherein n is a value from 0.2 to 20.

Assignees

• Basf Se

Inventors

• Behler Ansgar

Classifications

• A61K8/85

  Polyesters · CPC title

• C08G63/08 Primary

  Lactones or lactides · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• C07C69/68

  Lactic acid esters · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title