DE1017174B - Process for the preparation of new quaternary ammonium salts - Google Patents

Description

It has been found that valuable, new quaternary ammonium salts of the general formula

R '

RANR ₁ -CO-N;
R "

when you get tertiary amines of the general formula

, R '

r_a — n:

(1)

, R ₂

XR ₁ -CO-N:

(2) Method of manufacture
new quaternary ammonium salts

Applicant:

CIBA Aktiengesellschaft, Basel (Switzerland)

wherein R is one derived from an aliphatic carboxylic acid having at least 8 carbon atoms the - GO group bonded to A via a nitrogen atom, A is a low molecular weight alkylene radical with at least 2 carbon atoms and R 'and R " low molecular weight alkyl groups, e.g. B. mean ethyl or methyl groups, with compounds of the general formula

Representative: Dipl.-Ing. E. Splanemann, patent attorney,
ίο Hamburg 36, Neuer Wall 10

Claimed priority:
Switzerland from August 11, 1954

Dr. Otto Albrecht, New World,

and Dr. Erich Matter, Riehen (Switzerland),

have been named as inventors

Compounds of this composition are, in particular, the carboxamides of the general formula

quaternized, where R _{1 is} an alkylene radical optionally interrupted by heteroatoms and having fewer than 8 carbon atoms, R ₂ and R _{3 are} hydrogen, an alkyl radical or substituted alkyl radical and X is a substituent capable of forming the anion of a quaternary ammonium compound.

R —CO —NH-A -

R '

R "

to mention. In the formula (3), R is an aliphatic hydrocarbon radical with at least 7 carbon atoms, A- a low molecular weight alkylene radical with at least 2 carbon atoms and R 'and R "have low molecular weight alkyl groups. There are mainly tertiary amines of the general types formula

H ₃ C

(CEy-CO

NH ^ -CH ₃

-N

in terms of where k, m and η are integers with a value of at most 2 and ρ is an integer with a value of at least 11 and at most 16.

The tertiary amines to be used as starting materials can be derived from non-aromatic carboxylic acids, z. B. of capric acid, lauric acid, myristic acid, ■ pälmrtinsäure, stearic acid, oleic acid or Linoleic acid, and a di- or polyamine, e.g. B. ethylenediamine, propylenediamine, hexamethylenediamine, Diethylenetriamine, triethylenetetramine or tetraethylene pentamine or also of oxyalkylation products of such di- or polyamines as dioxyethylethylenediamine or trioxyethylethylenediamine, derive.

In general, the starting materials of the present

the process advantageously prepared in such a way that the above-mentioned di- or polyamines acylated with the carboxylic acids or functional derivatives thereof also mentioned above, such as acid chlorides, esters or anhydrides, and

7C9 70C43S

if still, no tertiary amino group in the starting materials is present, such a tertiary amino group by alkylation or oxalkylation, in particular by oxethylation with the aid of ethylene oxide.

Compounds of the formula (2) which are used in the present process for quaternizing the tertiary amines are advantageously those which, as substituents X capable of forming the anion of the quaternary compound, represent a halogen atom, e.g. B. a bromine atom or, in particular, a chlorine atom. R ₁ can be a low molecular weight alkylene radical, e.g. B. be an ethylene or methylene group, and the nitrogen atom can be further substituted with one or two low molecular weight alkyl groups or, preferably, not further substituted. Accordingly, a compound of the general formula is primarily used for the quaternization

In the German patent specification 855 550 quaternary ammonium compounds are already described which by quaternizing tertiary basic amines of the general formula

R__CO - N-CH ₉ - CH "- N:

R '

CH ₅₁

XH ₈

Halogen - CH ₂ - CO · NH ₂

(5) where R is an alkyl group having 7 to 15 carbon atoms and R _{1 is} a lower alkyl group, can be obtained with haloacetanilides. These compounds serve in particular as disinfectants.

Furthermore, US Pat. No. 2,407,701 describes, as detergents, compounds of the general formula

such as bromoacetic acid amide, especially chloroacetic acid amide into consideration.

Because halocarboxamides are preferably used for the production of the products according to the invention the quaternary ammonium salts usually contain a halogen ion, in particular, as the anion a chlorine ion. These halogen ions can of course counteract the ions of other inorganic ones or organic acids.

In addition, the quaternization of the tertiary amines can be carried out by the customary methods known per se be carried out, e.g. B. by heating the tertiary amines with compounds of the general Formula (2) at temperatures up to about 100 °, with or advantageously without additives and advantageously with exclusion of oxygen, e.g. B. in a nitrogen atmosphere.

The new compounds obtainable by the present process are quaternary ammonium salts, their cation of the general formula R - CO - NH - CH

₂ —N — Re — CO— Ν;

-Y

R '

RANR ₁ -CO-N;

R "

R ₃ wherein R is an aliphatic radical having at least 10 carbon atoms, R ₁ and R _{2 are} lower alkyl groups, R ₃ and R _{4 are} hydrogen atoms or lower alkyl groups and Y is an anion.

Compared to the latter compounds, the new compounds are characterized in particular by a much better resistance and also by a better foam force, foam resistance and Washing power off.

In the following examples, unless otherwise noted, parts are parts by weight and percentages are percentages by weight; the temperatures are given in degrees Celsius.

example 1

where R is a radical derived from an aliphatic carboxylic acid with at least 8 carbon atoms and bonded to A on the —CO group via a nitrogen atom, A a low molecular weight alkylene radical with at least 2 carbon atoms, R 'and R ″ low molecular weight alkyl groups, e.g. Ethyl or methyl groups, R _{1 is} an alkylene radical optionally interrupted by heteroatoms and having fewer than 8 carbon atoms, and R ₂ and R _{3 are} hydrogen, an alkyl or substituted alkyl radical.

The new quaternary ammonium compounds show strong cationic properties and are in usually soluble in water, with the solutions developing a copious foam. You let yourself Use as washing, wetting, dispersing or emulsifying agent. For example, they can be used to manufacture used by very good foaming and effective shampoos or other cosmetic preparations will. Against oxidizing agents, especially hydrogen peroxide, they prove to be in the Usually very persistent.

5.6 parts of N, N-dimethylpropylenediamine acylated with coconut fatty acid and 1.9 parts of chloroacetamide are heated in a stream of nitrogen in a water bath, the quaternary ammonium salt being formed after a short time. The latter is clearly soluble in water.
50

Example 2

4 parts of N, N-diethylpropylenediamine acylated with technical stearic acid and 0.94 part of chloroacetamide are heated in a stream of nitrogen in a boiling water bath for 6 hours with stirring. The quaternary ammonium salt thus obtained is soluble in water.
Mixing 21.6 parts of the quaternary ammonium salt described above with 7 parts of about 90% lactic acid, 7.85 parts of a water-soluble condensation product of tert-dodecyl mercaptan and ethylene oxide, e.g. B-. the one whose cloud point in 0.115% solution is about 69 °, 4.9 parts of N-oxyethyl coconut fatty acid amide, 2 parts of ρ - (stearoyl - amino) - phenyl - trimethylammonium methosulfate and 56 parts of water are obtained Very effective shampoo, which is able to develop an ample foam and has a very good cleaning effect.

Claims (4)

Claims. 1. Process for the preparation of new quaternary ammonium salts of the general formula R ' / R ₂ RANR ₁ -CO-N R " which differ from N-acylalkylenediamines and carboxamides derive, characterized in that tertiary amines of the general formula (1) R-α-n; R ' R " (1) wherein R is a abgelei- from an aliphatic carboxylic acid having at least 8 carbon atoms zo ended, attached to the -CO- group through a nitrogen atom in A radical, A is a low molecular alkylene radical having at least 2 carbon atoms and R 'and R "are low molecular weight alkyl groups with compounds of the general formula (2) XR ₁ -CO-Nf (2) quaternized, wherein R _{1 is} optionally through Heteroatoms-interrupted alkylene radical with fewer than 8 carbon atoms, R ₂ and R _{3 represent} hydrogen, an alkyl radical or substituted alkyl radical and X represent a substituent capable of forming the anion of a quaternary ammonium compound. 2. The method according to claim 1, characterized in that that the tertiary amines with compounds of the general formula Halogen - CH ₂ - CO - NH ₂ preferably with chloroacetic acid amide, quaternized. 3. The method according to claim 1, characterized in that that tertiary amines of the general formula are used as starting materials , R ' R-CO-NH-A-NC used, in which R is an aliphatic hydrocarbon radical having at least 7 carbon atoms, A is a low molecular weight alkylene radical with at least 2 carbon atoms and R 'and R "mean low molecular weight alkyl radicals. 4. The method according to claim 3, characterized in that that tertiary amines of the general formula are used as starting materials , (CH ₂ ), H ₃ C - (CH ₈ ) - CO -NH- (CH ₈ ) J used, in which k, m and η are integers with a value of at most 2 and p is an integer with a value of at least 11 and at most 16. 40 Publications considered:
German Patent No. 855 550;
Austrian Patent No. 160 900;
U.S. Patent No. 2,407,703. When the registration was announced, 4 pages of test reports were laid out. © 709 700/436 10.57