Method of making a composition of an alkanolamine alkylamide and a polyol

Patent metadata

Field	Value
Publication number	US-10266486-B2
Application number	US-201616070326-A
Country	US
Kind code	B2
Filing date	Sep 13, 2016
Priority date	Jan 29, 2016
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

The disclosure generally provides methods for preparing compositions comprising alkanolamine alkylamides and polyols. This disclosure further relates to methods for preparing compositions comprising alkanolamine alkylamides and polyols that can be used in formulations that provide moisturization.

First claim

We claim:

1. A method of making a composition comprising a compound of formula (I)

wherein
Z is (a) a linear or branched C 2 -C 6 alkylene optionally substituted with one or more —OH or —(C 1 -C 3 alkyl)-OH, or (b) (—R 2 —O—R 3 —) n , where n is an integer from 1 to 5, and each R 2 and R 3 is independently —CH 2 —CR 4 H—, wherein R 4 is H or an unsubstituted linear or branched C 1 -C 3 alkyl; and
R 1 is an unsubstituted linear or branched C 1 -C 3 alkyl;

and a polyol,
the method comprising reacting an alkanolamine of formula (II)

with a polyol ester comprising at least one —C(O)R 1 moiety.

2. The method of claim 1 , wherein the polyol is derived by the cleavage of at least one —C(O)R 1 moiety from said polyol ester.

3. The method of claim 1 , wherein the polyol ester is of formula (III):

wherein
R 1 is an unsubstituted linear or branched C 1 -C 3 alkyl;
R 5 is a linear or branched C 3 -C 6 alkyl or a mono-, di-, oligo or poly-saccharide sugar group;
m is an integer from 1 to 10; and
p is an integer from 0 to 9, provided that sum of m and p is at least 2 and less than or equal to the number of carbon atoms in R 5 .

4. The method on claim 1 , wherein the reaction is conducted without a catalyst.

5. The method of claim 1 , wherein the reaction is conducted in the presence of a catalyst.

6. The method of claim 5 , wherein the catalyst is sodium carbonate, potassium carbonate, sulfuric acid, or phosphorous acid.

7. The method of claim 1 , wherein the reaction is conducted without additional solvent.

8. The method of claim 1 , wherein the reaction is conducted at a temperature of 100° C. to 140° C., or at 115° C. to 130° C., or at 120° C. to 125° C.

9. The method of claim 1 , wherein the molar ratio of the alkanolamine of formula (II) and the polyol ester is about X:1, or about X:1.01, or about X:1.05, or about X:1.1, or about X:1.15, or about X:1.2, or about X:1.25, wherein X is the number of —C(O)R 1 moieties on the polyol ester.

10. The method of claim 1 , wherein R 1 is selected from methyl and ethyl.

11. The method of claim 1 , wherein Z is a linear or branched C 2 -C 6 alkylene optionally substituted with one or more —OH or —(C 1 -C 3 alkyl)-OH.

12. The method of claim 1 , wherein Z is (—R 2 —O—R 3 —) n , where n is an integer from 1 to 4, and each R 2 and R 3 are independently selected from —CH 2 —CR 4 H—, and R 4 is H or an unsubstituted linear or branched C 1 -C 3 alkyl.

13. The method of claim 1 , wherein the polyol ester is 1,2,3-triacetoxypropane and the polyol is glycerol.

14. The method of claim 1 , wherein the compound of formula (I) is:

Assignees

• Akzo Nobel Chemicals Int Bv

Inventors

• Bevinakatti Hanamanthsa
• White Karen Lee

Classifications

• C07C231/02 Primary

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• A61K8/42

  Amides · CPC title

• C07C29/00

  Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring · CPC title

• A61K2800/805

  Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95 · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title