Quaternary ammonium derivatives, the process for their preparation and their use as surfactants
AssigneeSociete D'Exploitation De Produits Pour Les Industries Chimiques Seppic
InventorsBernard Brancq, Jean-Pierre Boiteux
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Abstract
The present invention relates to novel quaternary ammonium derivatives wh have properties similar to those of non-ionic, amphoteric and cationic surfactants, to their preparation and to their use as surfactants in foaming and emulsifying compositions intended for use in the fields of pharmaceutics, cosmetics, hygiene and detergency. These derivatives have the general formula ##STR1## wherein essentially R is an alkyl or alkenyl radical having from 5 to 29 carbon atoms, R.sub.1 and R.sub.2 are an alkyl radical having from 1 to 4 carbon atoms, R.sub.3 is a 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, methyl or 2,3,4,5,6-pentahydroxyhexyl radical and X is a halogen atom or a hydroxyl group.
Claims15
A novel quaternary ammonium compound of the formula:
- ##STR12## in which:
- R is a linear or branched alkyl or alkenyl radical having from 5 to 29 carbon atoms;
- m is an integer equal to 2 or 3;
- n is equal to 1;
- R.sub.1 and R.sub.2 are independently:
- an alkyl radical having from 1 to 4 carbon atoms, or
- a hydroxymethyl, hydroxyethyl or hydroxypropyl radical;
- p is an integer between 1 and 3;
- R.sub.3 is a group ##STR13## in which:
- q is an integer between 1 and 5,
- y is an integer equal to 0 or 1,
- R.sub.5 is a hydrogen atom or a methyl radical, and
- r is an integer between 0 and 10, it being specified that r and y cannot simultaneously be equal to 0;
- a group
- --(CH.sub.2).sub.s --(CHOH).sub.t --(CH.sub.2).sub.u --CH.sub.3
- in which:
- s is an integer between 0 and 2,
- t is an integer between 1 and 6, and
- u is an integer between 0 and 5;
- or a group
- --(CH.sub.2).sub.v --(CHOH).sub.w --CH.sub.2 OH
- in which:
- v is an integer equal to 0 or 1, and
- w is an integer between 1 and 6;
- R.sub.4 is the hydrogen atom or has the same meaning as R.sub.3 ;
- and
- X is a chlorine or bromine atom or a hydroxyl group.
A process according to claim 16 wherein the compound of Formula (IV) is obtained by the condensation of an aminoalkylamine of the formula ##STR17## in which m, R.sub.1 and R.sub.2 are as defined therein, with a fatty acid of the formula RCOOH or a precursor thereof, wherein R is a linear or branched alkyl or alkenyl radical having from 5 to 29 carbon atoms.
The process of claim 8 wherein the amount of residual amine is reduced to a value below 1%.
A novel quaternary ammonium compound of the formula:
- ##STR18## in which;
- R is a linear or branched alkyl or alkenyl radical having from 5 to 29 carbon atoms;
- m is an integer equal to 2 or 3;
- n is equal to 1;
- R.sub.1 and R.sub.2 are independently:
- an alkyl radical having from 1 to 4 carbon atoms, or
- a hydroxymethyl, hydroxyethyl or hydroxypropyl radical;
- p is an integer between 1 and 3;
- R.sub.3 is a radical selected from the group consisting of 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl and 2,3,4,5,6-pentahydroxyhexyl radicals;
- R.sub.4 is the hydrogen atom or has the same meaning as R.sub.3 ;
- and X is a chlorine or bromine atom or a hydroxyl group.
A quaternary ammonium compound of the formula:
- ##STR19## in which n is equal to 1;
- R is a linear or branched alkyl or alkenyl radical having 5 to 29 carbon atoms;
- m is equal to 3;
- R.sub.1 and R.sub.2 are a methyl radical;
- p is equal to 1;
- R.sub.3 is a 2-hydroxyethyl radical;
- R.sub.4 is the hydrogen atom;
- and X is a chlorine atom or a hydroxyl group.
A quaternary ammonium compound of formula:
- ##STR20## in which R is a linear or branched alkyl or alkenyl radical having from 5 to 29 carbon atoms;
- m is equal to 3;
- R.sub.1 and R.sub.2 are a methyl radical;
- p is equal to 1;
- R3 is a 2-hydroxyethyl radical;
- R.sub.4 is a 2-hydroxyethyl radical and X is a chlorine atom or a hydroxyl group.
A quaternary ammonium compound of the formula:
- ##STR21## in which n is equal to 1, R is a linear or branched alkyl or alkenyl radical having 5 to 29 carbon atoms, m is equal to 3, R.sub.1 and R.sub.2 are independently an alkyl radical having from 1 to 4 carbon atoms, p is equal to 1, R.sub.3 is a 2-hydroxyethyl radical, R.sub.4 is a hydrogen atom, and X is a chlorine atom or a hydroxyl group.
A quaternary ammonium compound of the formula:
- ##STR22## in which n is equal to 1, R is a linear or branched alkyl or alkenyl radical having 5 to 29 carbon atoms, m is equal to 3, R.sub.1 and R.sub.2 are independently an alkyl radical having form 1 to 4 carbon atoms, p is equal to 1, R.sub.3 is a 2-hydroxyethyl radical, R.sub.4 is a 2-hydroxyethyl radical, and X is a chlorine atom or a hydroxyl group.
Dependencies are inferred from the claim text.