Amides of aliphatic polyamines and 12-hydroxyoctadecanoic acid and lipase stable thickener compositions

Patent metadata

Field	Value
Publication number	US-11680228-B2
Application number	US-201716079632-A
Country	US
Kind code	B2
Filing date	Feb 16, 2017
Priority date	Feb 26, 2016
Publication date	Jun 20, 2023
Grant date	Jun 20, 2023

Abstract

Amides of an aliphatic polyamine with two or three molecules of 12-hydroxyoctadecanoic acid, wherein the polyamine comprises at least one primary amino group for each molecule of 12-hydroxyoctadecanoic acid and additionally at least one secondary and/or tertiary amino group, can be used in a lipase stable thickener composition comprising from 50 to 95% by weight of one or more of the amides, from 5 to 50% by weight of one or more diluents and from 0 to 10% by weight water, and such thickener compositions can be prepared by a step of heating a starting mixture comprising hydrogenated castor oil and one or more aliphatic polyamines and adding one or more diluents before or after the heating step.

First claim

The invention claimed is:

1. An amide of an aliphatic polyamine with two or three molecules of 12-hydroxyoctadecanoic acid, wherein the polyamine comprises at least one primary amino group for each molecule of 12-hydroxyoctadecanoic acid and additionally at least one secondary and/or tertiary amino group.

2. The amide of claim 1 , having the structure of formula (I):
R 1 (CO)NH(CH 2 ) x [NR 2 (CH 2 ) x ] y NH(CO)R 1   (I)

wherein:
R 1 (CO) is 12-hydroxyoctadecanoyl;
R 2 groups are independently of one another hydrogen, methyl or (CH 2 ) x NH(CO)R 1 with the proviso that no more than one R 2 group is (CH 2 ) x NH(CO)R 1 ;
x=2 or 3; and
y=1, 2 or 3.

3. The amide of claim 2 , wherein R 2 is hydrogen and x=2.

4. The amide of claim 3 , wherein y=1.

5. A lipase stable thickener composition, comprising:
from 50 to 95% by weight of one or more amides of claim 1 ;
from the group consisting of 5 to 50% by weight of one or more diluents selected from methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, oligoethylene glycols with a molecular weight of less than 400 g/mol, oligopropylene glycols with a molecular weight of less than 400 g/mol, monoethers of said glycols with C 1-3 alcohols, and glycerol; and
from 0 to 10% by weight water.

6. The thickener composition of claim 5 , wherein at least 80% by weight of said amides have the structure of formula (I):
R 1 (CO)NH(CH 2 ) x [NR 2 (CH 2 ) x ] y NH(CO)R 1   (I)

wherein:
R 1 (CO) is 12-hydroxyoctadecanoyl;
R 2 groups are independently of one another hydrogen, methyl or (CH 2 ) x NH(CO)R 1 with the proviso that no more than one R 2 group is (CH 2 ) x NH(CO)R 1 ;
x=2 or 3; and
y=1, 2 or 3.

7. The thickener composition of claim 5 , wherein said diluents comprise at least 80% by weight of propylene glycol, dipropylene glycol or a mixture of both.

8. The thickener composition of claim 5 , wherein at least one of the R 2 groups is hydrogen and the composition comprises from 0.2 to 10% by weight water.

9. The thickener composition of claim 5 , wherein the composition comprises from 10 to 30% by weight of said diluents.

10. The thickener composition of claim 5 , wherein the composition comprises at least 2% by weight of glycerol.

11. The thickener composition of 5 , wherein the composition has a melting range of from 75 to 120° C.

12. The thickener composition of 6 , wherein R 2 is hydrogen, x=2 and y=1.

13. A method of making the lipase stable thickener composition of claim 5 , comprising:
a) heating a starting mixture comprising hydrogenated castor oil and one or more aliphatic polyamines, wherein each polyamine comprises at least two primary amino groups and additionally at least one secondary and/or tertiary amino group, to a temperature of from 120 to 160° C. to provide a reaction mixture, wherein hydrogenated castor oil and said amines are used in amounts providing a molar ratio of 12-hydroxyoctadecanoyl groups of said hydrogenated castor oil to primary amino groups of said amines of from 0.9 to 1.1; and
b) before or after step a), adding one or more diluents selected from the group consisting of: methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, oligoethylene glycols with a molecular weight of less than 400 g/mol, oligopropylene glycols with a molecular weight of less than 400 g/mol, and monoethers of said glycols with C 1-3 alcohols in an amount of from 10 to 100% by weight, based on the combined amount of hydrogenated castor oil and said amines.

14. The method of claim 13 , wherein said polyamines have a structure of formula (II):
H 2 N(CH 2 ) x [NR 2 (CH 2 ) x ] y NH 2 ,   (II)

wherein:
R 2 groups are independently of one another hydrogen, methyl or (CH 2 ) x NH 2 , with the proviso that no more than one R 2 group is (CH 2 ) x NH 2 ;
x=2 or 3; and
y=1, 2 or 3.

15. The method of claim 14 , wherein R 2 is hydrogen and x=2.

16. The method of claim 15 , wherein y=1.

17. The method of claim 13 , wherein at least one of the R 2 groups is hydrogen and the method comprises the additional steps of:
a) adding water to said reaction mixture, optionally comprising said diluents, in an amount of from 1 to 5% by weight, based on the combined amount of hydrogenated castor oil and said amines; and
b) maintaining the mixture resulting from step a) at a temperature of from 100 to 130° C. for a period of from 1 to 3 hours.

18. The method of claim 13 , wherein said diluents are propylene glycol, dipropylene glycol or a mixture of both.

19. The method of claim 18 , wherein R 2 is hydrogen, x=2 and y=1.

20. The amide of claim 4 , wherein R 2 is hydrogen or methyl.

Assignees

• Evonik Operations Gmbh

Inventors

• Köhle Hans-Jürgen
• Klostermann Michael
• Tian Gonglu

Classifications

• C11D3/38627

  containing lipase · CPC title

• C11D3/3723

  Polyamines or polyalkyleneimines · CPC title

• C11D3/32 Primary

  Amides; Substituted amides · CPC title

• C11D3/2044

  linear · CPC title

• C11D3/2065

  Polyhydric alcohols · CPC title