Lactame or amino acid-based fatty amide, and use as an organogelator

Patent metadata

Field	Value
Publication number	US-9796663-B2
Application number	US-201414906304-A
Country	US
Kind code	B2
Filing date	Jul 18, 2014
Priority date	Jul 25, 2013
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

The invention relates to a fatty amide, which is based on:
a) a diamine selected from aromatic or cycloaliphatic or linear C 2 to C 10 aliphatic diamines, b) a C 3 to C 12 lactam or amino acid, c) optionally, a second primary diamine different from said diamine a), d) a hydroxylated fatty monoacid, e) optionally, a nonhydroxylated monoacid chosen from linear C 6 to C 12 aliphatic acids,

with a mole ratio b/(a+c) of 0.25 to 3/1.

The invention also covers a process for the preparation of said amide and its use as organogelator or rheology additive in an organic solvent medium, in particular in coating, glue or adhesive, mastic, sealant or stripping agent compositions or molding or cosmetic compositions.

First claim

The invention claimed is:

1. A fatty amide derived from the reaction of:
a) a primary diamine selected from the group consisting of aromatic, cycloaliphatic and linear C2 to C10 aliphatic diamines,
b) a C3 to C12 lactam or amino acid,
c) optionally, a second primary diamine different from said diamine a) chosen from the group consisting of linear C2 to C10 aliphatic diamines,
d) a hydroxylated fatty C18 or C20, monoacid,
e) optionally, a nonhydroxylated monoacid chosen from the group consisting of linear C6 to C12 aliphatic acids, the mole ratio e/d of said monoacid e) with respect to said monoacid d) not exceeding 0.5,
and in that the mole ratio b/(a+c) is from 0.25 to 3/1.

2. The fatty amide of claim 1 wherein said monoacid d) is 12 hydroxystearic acid.

3. The fatty amide of claim 1 wherein the mole ratio b/(a+c) is from 0.25 to 2/1.

4. The fatty amide of claim 1 wherein said diamine a) is selected from the group consisting of aromatic diamines.

5. The fatty amide of claim 4 wherein said amine a) is an aromatic diamine selected from the group consisting of: xylylenediamines phenylenediamines, and toluylenediamines.

6. The fatty amide of claim 5 wherein said diamine is xylylenediamine.

7. The fatty amide of claim 4 wherein said monoacid d) is 12 hydroxystearic acid in the absence of said monoacid e).

8. The fatty amide of claim 4 wherein said monoacid d) is 12 hydroxystearic acid in the presence of said monoacid e).

9. A process for the preparation of the fatty amide of claim 1 comprising the successive steps of:
i) reacting said diamine a) with said lactam or amino acid b), with formation of a diamine a) modified b),
ii) reacting product from stage i) with said monoacid d) in the presence or absence of said monoacid e) and in the presence or absence of said diamine c).

10. The process according to claim 9 , wherein said component b) is a lactam and wherein said reaction with said amine a) is an anionic oligomerization of said lactam b) using said diamine as anionic initiator.

11. A process for the preparation of the fatty amide of claim 1 comprising the successive steps of:
i′) reacting said monoacid d) or optionally of the said monoacid e) if present, with said lactam or amino acid b), to produce corresponding monoacid modified by b),
ii′) reacting said modified monoacid from step i′) with said diamine a), in the presence or absence of said diamine c) and if said monoacid from said step i′) is said monoacid d), then in the presence or absence of said monoacid e), otherwise, if said monoacid from said step i′) is the monoacid e), then in the presence of said monoacid d).

12. The process according to claim 11 , wherein said monoacid e) is present with said process comprising successive reaction steps:
i′) reacting said monoacid e) with said lactam or amino acid b), with formation of a monoacid e) modified b),
ii′) reacting said modified monoacid formed at stage i′) with said diamine a) and said monoacid d) and in the presence or in the absence of said diamine c).

13. An organogelator comprising or consisting of at least one fatty amide according to claim 1 .

14. The organogelator of claim 13 in preactivated form in an organic solvent.

15. An organic binder composition comprising at least one amide according to claim 1 .

16. The fatty amide of claim 1 , wherein said hydroxylated fatty C18 or C20 monoacid is chosen from the group consisting of 12 hydroxystearic acid and 14 hydroxyeicosanoic acid.

Assignees

• Arkema France

Inventors

• Bernard Michael Y

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K2800/48

  Thickener, Thickening system · CPC title

• C07C233/31

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom · CPC title

• A61K8/42 Primary

  Amides · CPC title

• A61K2800/10

  General cosmetic use · CPC title