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

• US 10,266,486 B2
• Filed: 09/13/2016
• Issued: 04/23/2019
• Est. Priority Date: 01/29/2016
• Status: Active Grant

• Current Assignee: Nouryon Chemicals International B.V. (Nouryon BV)
• Original Assignee: Akzo Nobel Chemicals International B.V. (Nouryon BV)
• Inventors: Bevinakatti, Hanamanthsa, White, Karen Lee
• Primary Examiner(s): Parsa, Jafar F
• Application Number:
  US16/070,326
• Publication Number:
  US 20190031598A1
• Time in Patent Office: 952 Days
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 2800/805 Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C07C 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 29/00 Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
• CPC Class Codes: C07C 31/225 Glycerol

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.

Claims

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

2. The method of claim 1, wherein the polyol is derived by the cleavage of at least one —

C(O)R¹ moiety from said polyol ester.

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

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)R¹ moieties on the polyol ester.

10. The method of claim 1, wherein R¹ is selected from methyl and ethyl.

11. The method of claim 1, wherein Z is a linear or branched C₂-C₆ alkylene optionally substituted with one or more —

OH or —

(C₁-C₃ alkyl)-OH.

12. The method of claim 1, wherein Z is (—

R²—

O—

R³—

)_n, where n is an integer from 1 to 4, and each R² and R³ are independently selected from —

CH₂—

CR⁴H—

, and R⁴ is H or an unsubstituted linear or branched C₁-C₃ 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: