.alpha.-amino-substituted acetic acids or acid salts and their u

Details .alpha.-amino-substituted acetic acids or acid salts and their u .alpha.-amino-substituted acetic acids or acid salts and their u

1995-06-19

1999-02-09

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 54, 554 59, 564123, 564193, 564215, 564488, C07C23100

Patent

active

058697128

DESCRIPTION:

BRIEF SUMMARY
The subject of the present invention is .alpha.-amino-substituted acetic acids or acid salts which are totally free of haloacetic acid and alkali metal halide, as well as a process for the preparation of the said acids or salts and the use of the said .alpha.-amino substituted acetic acids or acid salts of very high purity as surface-active agents in cosmetic compositions.


SUMMARY OF THE INVENTION

According to the invention, they are .alpha.-amino-substituted acetic acids or acid salts of formula (I) ##STR3## in which formula R represents a hydrogen atom or a linear or branched and optionally substituted C.sub.1 -C.sub.18 alkyl or alkoxy group, ammonium residue characterized in that they are totally free of haloacetic acid and alkali metal halide.


DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention is very particularly aimed at the acid form of N-lauroyl-N'-(2-hydroxyethyl)-N'-(carboxymethyl)ethylenediamine and its salts.
Numerous compounds of general formula (I) and more particularly their inorganic salts are widely employed in the detergent and cosmetics industries as amphoteric agents. Apart from their surfactant qualities, these compounds also show themselves to have, owing to their chemical structure, a very desirable biodegradable nature. By way of a particularly advantageous compound, there may especially be mentioned the sodium salt of N-lauroyl-N'-(2-hydroxyethyl)-N'(carboxymethyl)ethylene-diamine.
These compounds are conventionally prepared from a compound of general formula (II) ##STR4## which undergoes condensation with chloroacetic acid or with one of its salts.
This synthesis route is, however, not satisfactory for various reasons.
Direct condensation of a chloracetic acid only leads to a poor yield, of the order of 33%, and in addition requires a purification step.
As regards more particularly the inorganic salts of chloroacetic acid, they do indeed lead to better yields, but also to the formation of large amounts of impurities such as, for example, sodium chloride in the particular case of sodium chloroacetate. It is then necessary to use awkward purification techniques, of the electrodialysis or osmosis type which, apart from their cost, have the disadvantage of being difficult to implement industrially.
Finally, like its salts, chloroacetic acid has an irritant nature which has now been well established.
For these reasons, it is desirable now to have available compounds of formula (I) which are totally free of haloacetic acid and alkali metal halide. In addition, the acids or acid salts of the invention preferably do not contain more than 0.5% of their weight of glycolic acid.
The compounds forming the subject of the invention are capable of being obtained by reaction, under hot conditions, of glyoxal, or of a precursor of glyoxal, with a secondary amine or one of its salts of general formula (II), ##STR5## in which R represents a hydrogen atom or a linear or branched and optionally substituted C.sub.1 -C.sub.18 alkyl or alkoxy group, optionally followed by hydrolysis.
Apart from the fact that such a process precludes the use of chloroacetic acid or one of its derivatives, it advantageously permits a direct access to the acid form and thus rids itself of the standard inorganic contaminants such as sodium chloride.
The secondary amine of general formula (II) may preferably be obtained by in situ or extemporaneous basic hydrolysis, in the reaction medium, of an imidazoline of general formula (III) ##STR6## in which formula R represents a hydrogen atom or a linear or branched and optionally substituted C.sub.1 -C.sub.18 alkyl or alkoxy group.
Hydrolysis of the imidazoline of general formula (III) is effected in a conventional manner in aqueous medium and in the presence of a base. The base is more particularly sodium hydroxide. A person skilled in the art is able, owing to his technical competences, to reproduce this hydrolysis.
From the point of view of the operating conditions, this process for the preparation of the compounds of formula (I) is relatively easy to implement

REFERENCES:
Chemical Abstr. of JP-05'311193, including anticipted compounds, Nov. 1993.

Affiliated with

Also associated with

Rating

.alpha.-amino-substituted acetic acids or acid salts and their u does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with .alpha.-amino-substituted acetic acids or acid salts and their u, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and .alpha.-amino-substituted acetic acids or acid salts and their u will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1950162