DE2312818A1 - NEW QUARTAERE AMMONIUM SALTS AND THEIR USE AS TEXTILE SOFTENERS - Google Patents

Description

Patent Department 4 Düsseldorf, March 12, 1973

Dr. HH / Ka / sch Henkelstrasse Sj

Patent pending and n, .g.

D 4507

"New quaternary ammonium salts and their use as fabric softeners ¹¹

The invention relates to new quaternary ammonium salts, a process for their preparation and their use as textile softeners, especially in laundry aftertreatment agents.

Quaternary ammonium compounds with two long-chain and two short-chain aliphatic hydrocarbon radicals in the molecule, such as distearyldimethylammonium chloride, are used as fabric softeners for the aftertreatment of washed laundry, whereby the laundry gets a soft and fluffy feel. In use, however, the laundry treated in this way shows a clear deteriorated pumping speed.

It has now been found that aliphatically N, N-disubstituted N- (2-cyanoethyl) -N- (3-halogen-2-hydroxypropyl) ammonium salts of formula I.

CH ₂ CH ₂ CN

R _N CH ₀ CHOHCH ₀ -R ,, X ^ (I)

R ₂

in the FL an aliphatic hydrocarbon radical with 10-24, preferably 12-18 carbon atoms, R ₂ an optionally substituted alkyl radical with 1-4 carbon atoms, R ^ a chlorine or bromine atom and "Xy ^ an anion from the group of chloride, bromide, hydroxide, Methosulphate and ethosulphate mean

409838/1015

Henkel & de GmbH see below 2 «r fci.nionm.idu», ο 4507

Surprisingly, they have excellent laundry-finishing properties and are suitable for use as textile softeners, in particular in laundry aftertreatment agents. Particularly advantageous in addition to the good softening effect is the property of the new substances to only negligibly affect the absorbency of the treated tissue. Treatment with the active ingredients according to the invention also largely prevents unwanted static charging of the textiles, especially those made of synthetic fibers. The treated textiles are also easy to iron. Antimicrobial agents and optical brighteners can be easily incorporated into liquid and solid packaging with the new textile softeners.

As aliphatic hydrocarbon radicals R 1 in the formula I , straight-chain or branched, saturated or unsaturated radicals of synthetic or natural origin come into consideration. Particularly preferred radicals R ₁ are the straight- chain alkyl radicals such as, for example, the decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl and tetracosyl radical. For the substituent Rp, alkyl radicals with 1-4 carbon atoms, ie the methyl, ethyl or a propyl or butyl radical, and substituted alkyl radicals such as the 2-hydroxyethyl or 2- hydroxypropyl radical are suitable ; The methyl and ethyl radicals are of particular interest.

The new substances of the formula I are solid, water- soluble or dispersible substances at normal temperature] they are also soluble in lower alcohols such as methanol, ethanol and isopropyl alcohol.

409838/1015

Henkel & CIe GmbH mm yy »'Poi.n» onm.leid ο 4 ^ 07

The invention further relates to a process for the preparation of the new substances of the formula I. This process is characterized in that _{1 mol of acrylonitrile is added to 1 mol of a primary aliphatic amine R 1} -NHg in the melt, preferably under a protective gas atmosphere, then in Reacts the presence of catalytic amounts of AlCl-, or AlBr-, with 1 mole of epichlorohydrin or epibromohydrin and the tertiary amine thus formed, optionally with the addition of a solvent, quaternized with an alkylating agent. In the formula of the primary aliphatic amine R, -NH ^, the radical R, has the same meaning as in the formula I; the radical R ₂ and the anion X ~ are introduced into the product of the formula I by the alkylation. The process product is obtained after the solvent has been distilled off and is generally used in this form for industrial purposes. It may be advisable to purify by dissolving or recrystallizing, for example from acetone, ethyl acetate, acetonitrile, isopropyl alcohol or mixtures of these solvents with one another, optionally using activated carbon or other adsorbents.

The compounds dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, etc., for example, are used as primary aliphatic amines of the formula R ₁ -NH _{2 in the process according to the invention.} Also of interest are those amines R ₁ -NHp whose radical R _{1 is derived} from fatty acids of natural origin, such as coconut fatty acid, tallow fatty acid, soy fatty acid, rapeseed fatty acid or their hydrogenation products, such as coconut alkylamine, tallow alkylamine, etc.

The organic solvents used in the manufacturing process are, for example, the lower alcohols such as Ethanol, isopropyl alcohol, butanol, also acetonitrile, glycol, ethylene glycol monomethyl and dimethyl ether, dimethylformamide, Dimethyl sulfoxide etc. and optionally mixtures of these solvents with water are used.

409838/1015 " ⁴ "

Henkel & CIe GmbH s.it · 4 »r pat * Man> n« iduna d ^ 507

To the erf indungspemäßen V / irkstoffen of formula I include, for example, the substances listed in Table I below.

Tabel

N-tetradecyl-N-methyl-N- (2-cyanoMethyl) -N- (3-chloro-2-hydroxypropyl) ammonium methosulfate

N-Dcdecyl-N-ethyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium ethosulfate

N-dodecyl-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) -ammonium methosulfate

N-hexadecyl-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium methosulfate

N-Octadecyl-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) -ammoniumniethosulfat

N-dodecyl -N-methyl -N- (2 -cyanoethyl) -N- (jJ-chloro-2-hydroxypropyl) ammonium chloride

N-dodecyl-N- (2-hydroxyethyl) -N- (2-cyanoethyl) -N-O-bromo-2 -hydr oxypr opy 1) -ammonium bromide

N-dodecyl-N-buty1-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium bromide

N-Cocosalky1-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium chloride

N-Tallowalkyl-N-methyl-N- (2-cyanoethyl-N- (3-chloro - .. 2. hydroxypropyl) ammonium chlorine id

N-dodecyl-N- (2-hydroxyethyl) -N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium hydroxide

N-dodecyl-N- (2-hydroxypropyl) -N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl) ammonium hydroxide

409838/1015

Henkel & Cio GmbH $. ». 5 » _r Ραΐο« ΐο _Γ «, .ι <ι» ι.β ο ^ 507

The after-treatment of the laundry with the active ingredients of the formula I can be carried out in various ways, depending on the drying process, that is to be used '. 'Will be in a hot air wash When dried in a dryer, the vials can be sprayed directly with an active ingredient dispersion or the active ingredient can be sprayed over Bring a carrier into contact with the laundry, for example by spraying the inner walls of the drying device with the active ingredient dispersion before loading the device with laundry or by loading a carrier soaked with the active ingredient dispersion large surface, whereby the fabric softener is absorbed onto the laundry during the drying process. Presently, however most of the ash dried hanging; therefore, the use of the plasticizer in the last rinsing bath also predominates of the washing process in hand washing and especially in machine washing. In the last-mentioned application variant the active ingredient of the formula I is used in the rinsing liquor in amounts of 0.05-1.0 g / l, preferably 0.1-0.5 g / l. aside from that other substances which can be used for the aftertreatment of washed laundry can be present in such a rinsing bath be selected so that the rinsing bath reacts neutrally to slightly acidic.

Finally, the invention relates to the use of the inventive Active ingredients of the formula I as fabric softeners in laundry aftertreatment agents.

According to the invention, the new substances can be used as textile softeners in powder or liquid laundry aftertreatment agents use, in addition to the active ingredients mentioned, at least one diluent for these active ingredients and optionally contain other common components of post-treatment agents.

409838/1015

Henkel & CIo GmbH s * it. 6 » _uf r _a t * Ma» ni «M _V « _e ο ^ 507

Water and / or water-soluble organic solvents are used as diluents for liquid after-treatment agents. and as a diluent for solid, powdery aftertreatment agents which are readily water-soluble or dispersible inert solid carrier substances in question.

As other common constituents of V / A after-treatment agents For example, dispersants, optical brighteners, antimicrobial agents, acidic additives, and fragrances apply Dyes etc. '

Carrier substances that can be used are, for example, urea, acetamide, sodium sulfate and, if appropriate, those below Use the acidic additives listed if they are in solid form. Solid polyethylene glycols are also available as Carriers useful.

To produce solid, powdery laundry aftertreatment agents, the active ingredients according to the invention can be used in organic Dissolved solvents are sprayed onto the moving solid carrier substances. Carrier substances are preferably used here with the largest possible surface and low bulk density, for example a bulk density of 100 - 700 g / l. Products of such bulk density are obtained, for example, by calcining inorganic salts containing water of crystallization, If you use urea as a carrier substance, you can also use the active ingredients with the molten urea, which you can remedy has added to lower the melting point, bring together and convert this melt into a powder. In all The powder properties can be incorporated by incorporation small amounts of substances with a large surface such as Improve microcrystalline silica, magnesium silicate, etc.

409838/1015

Henkel & CIe GmbH un · J «rr _o i.nton« .id "", d 4507

The composition of the particularly interesting liquid laundry aftertreatment agents in which those defined above new active ingredients can be used according to the invention is in generally in the range of the following recipe:

From 2.0 to 20.0, preferably 5.0 - 15.0 wt -.% Active ingredient of the formula I,

0.2 to 6.0, preferably 0.5 - 3 * 0 wt .- # dispersing agents, 0.0 - 30.0, preferably 1.0 - 15 * 0 wt -.% Water-soluble

organic solvent, 0.0 - 10.0, preferably 0.3 - 7 * 5 wt -.% other conventional

Components of laundry treatment agents, the remainder is water.

As other common constituents of laundry aftertreatment agents at least one of the following components can be present in the specified amounts based on the total composition be:

0.2 - 3.0 wt .- ^ antimicrobial agent,

0.2 to 6.0 wt -.% Acidic additives,

0.01 - 0.5 wt. JS cotton whitening agent,

0.01 - 0.5 wt .- # polyamide brighteners,

0.01 to 0.5 wt -.% Fragrance,

0.00001-0.05 wt. # Dye.

The following are those in the laundry aftertreatment agents ingredients still contained in addition to the active ingredient according to the invention Described in more detail sorted by substance class.

409838/1015

Henkel & CIe GmbH 'see below 8 «r» ... »ΐα« «.« ^ Ο ^ 507

The nonionic surfactants, hereinafter referred to as "nonionics", are particularly suitable as dispersants, as can be contained in the liquid and powder laundry aftertreatment agents. These include products which owe their hydrophilic properties to the presence of polyether chains, amine oxide, sulfoxide or phosphine oxide groups, alkylolamide groups and, in general, an accumulation of hydroxyl groups. Such nonionics contain at least one hydrophobic radical in the molecule, which usually consists of an aliphatic or alkyl aromatic hydrocarbon radical with 8-26, preferably 10-20 and in particular 12-18 carbon atoms, and at least one nonionic water-solubilizing group. The hydrophobic residue is linked to the water-solubilizing groups directly or via intermediate links. As intermediate members, for example, carboxylic acid ester or carbonamide groups, ether- or ester-like bonded residues of polyhydric alcohols, such as those of ethylene glycol, propylene glycol, glycerol or corresponding polyether radicals, are suitable.

Particularly suitable nonionics are the addition products of 4 - 40, preferably h - 20 mol of ethylene oxide with 1 mol of fatty alcohol, alkylphenol, fatty acid, fatty amine, fatty amide or alkanesulfonamide, such as the addition products of 5 - 16 mol of ethylene oxide with coconut oil. or tallow fatty alcohols, on oleyl alcohol or on secondary alcohols with 8-18, preferably 12-18, carbon atoms, and on mono- or dialkylphenols with 6-14 carbon atoms in the alkyl radicals.

Other suitable nonionics are the water-soluble, 20 - 250 Ethylene glycol ether groups and adducts of ethylene oxide containing 10-100 propylene glycol ether groups Polypropylene glycol (= P lur on ic ε ^ SJ), alkylenediamine polypropylene glycol (= Tetronics QP) and alkyl polypropylene glycols with 1-10 C atoms in the alkyl chain, in which the polypropylene glycol chain functions as a hydrophobic residue.

Nonionic surfactants of the amine oxide or sulfoxide type can also be used. 409838/1015 _ ₉ _

Henkel & Cie GmbH si »9» rρ _Ο ι. <Ιΐα _ηη ..ι <ΐυπα ο 4507

In addition to the mostly readily water-soluble surfactants, water-soluble dispersants may also be suitable as nonionic dispersants or compounds emulsifiable or dispersible in water, which either do not contain any hydrophobic residues in the sense of the nonionic surfactants described above, or which have the nature or the number of hydrophilic groups is insufficient to achieve complete water solubility. To the former include, for example, solid or liquid polyethylene glycols, ethylene oxide adducts of glycerine and other polyalcohols, etc .; to the latter, for example, partial fatty acid glycerides or alkoxylation products which are not or not completely water-soluble, e.g. those with 2-5 ethylene glycol ether residues in the molecule.

Useful water-soluble organic solvents are the lower alcohols with 1-5 carbon atoms such as methanol, Ethanol, propanol, isopropyl alcohol, butanol, amyl alcohol, and also the lower ketones acetone and methyl ethyl ketone as well Ethylene and diethylene glycol and their mono- or dimethyl or ethyl ethers. Of particular interest in practice is the isopropyl alcohol.

Inorganic and non-surface-active substances are suitable as acidic additives organic acids with 2-8 carbon atoms, such as amidosulfonic acid, urea phosphate, boric acid, oxalic acid, Lactic acid, glycolic acid, citric acid, tartaric acid, benzoic acid, phthalic acid, gluconic acid, acetic acid and propionic acid as well as the benzene, toluene or xylene sulfonic acids, sulfoacetic acid or sulfobenzoic acids.

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409838/1015

2312318

HENKEL & CLE GMBH su 10 "'M.inon" iw "ii _g o 4507

The preparations can contain, as optical brighteners for cotton, in particular derivatives of diaminostilbene disulfonic acid or its alkali metal salts. For example, salts of 4, V-bis (2-anilino-4-rnorpholino-1,3 _i 5-triazin-6-yl-amino) -stilbene-2,2'-disulfonic acid or similarly structured compounds which, instead of the Morpholino group carry a diethanolamino group, a methylamino group or a 2-methoxyethylamino group. Suitable brighteners for polyamide fibers are those of the 1,3-diaryl-2-pyrazoline type, for example the compound 1- (p-sulfamoylphenyl) -2- (p-chlorophenyl) -2-pyrazoline and similarly structured compounds that replace the sulfamoyl group, for example, the methoxycarbonyl, 2-methoxyethoxyearbonyl, the acetylamino or the vinylsulfonyl group. Polyamide brighteners which can also be used are the substituted aminocoumarins, for example 1-methyl-T-dirnethylamino- or 4-methyl-7-diethylaminocoumarin. The compounds 1- (2-benzimidazolyl) -2- (1-hydroxyethyl-2-benzimidazolyl) -ethylene and 1-ethyl- ^ - phenyl ^ -diethylamino-carbostyril can also be used as polyamide brighteners. The compounds 2,5-di- (2-benzoxazolyl) thiophene, 2- (2-benzoxazolyl) naphtho [2,3-b]] thiophene and 1,2-di- (5-methyl-2-benzoxazolyl) ~ ethylene suitable. Furthermore, brighteners of the substituted 4,4'-distyryldiphenyl type can be present; for example the compound 4,4'-bis (4-chloro-5-sulfostyryl) -diphenyl. Mixtures of the abovementioned brighteners can also be used.

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409838/1015

Henkel & CIe GmbH see page 11 ». roun «onm.id _V na ο ^

Among antimicrobial agents are here bactericidal or bacteriostatic or fungicidal or fungistatic effective connections understood. These '' materials are supposed to be soluble in water either as such or in the form of their salts. In the case of the antimicrobial which can be used according to the invention Active ingredients are mostly auartar ammonium compounds, especially those that have one long-chain aliphatic and two short-chain aliphatic hydrocarbon radicals an aromatic linked to the nitrogen atom via an aliphatic carbon atom, or contain an aliphatic organic radical containing double bonds in the molecule. Examples of such antimicrobial Quaternary ammonium compounds are the following: Dimethyl-benzyl-dodeeylammonium chloride, Dimethyl-benzyltetradecylammonium chloride, Dimethyl- (ethylbenzyl) -dodecylammonium chloride, dimethyl-benzyl-decylammonium bromide, diethylbenzyl-dodecylammonium chloride, Diethy1-benzyl-octyI-ammonium-chloride, Dibutyl-allyl-, methyl-ethyl-benzyl-, ethyl-cyclohexyl-allyl- and ethyl crotyl diethylaminoethyl dodecylammonium chloride.

Other useful antimicrobial agents are both lower alcohols or diols with 3-5 carbon atoms substituted by bromine and by the nitro group such as the compounds 2-bromo-2-nitro-propane-1,3-diol, 1-Bromo-1-nitro-3 »! 5»] 5-trichloro-2-propanol, 2-bromo-2-nitrobutanol.

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A09838 / 101B

2,319,818

Henkel & CIe GmbH su 12, ", n <* nta" m, uvn _g d 4507

Also suitable as antimicrobial active ingredients are phenolic compounds of the halogenated phenol type with 1-5 halogen substituents, in particular chlorinated phenols; Alkyl, cycloalkyl, aralkyl and phenylphenols with 1-12 carbon atoms in the alkyl groups and with 1-4 halogen substituents, in particular chlorine and bromine in the molecule; Alkylenebisphenols, in particular derivatives substituted by 2-6 halogen atoms and optionally lower alkyl or trifluoromethyl groups, with an alkylene bridge member consisting of 1-10 carbon atoms; Hydroxybenzoic acids or their esters and amides, in particular anilides; in the benzoic / or aniline radical, and may be substituted in particular by 2 or Halogenatcme and / or Trlfluormethylgruppen; o-phenoxy-phenolics, which by 1 - 1, preferably 2-5 halogen atoms and / or hydroxyl, cyano, carbo methoxy group and carboxyl group or lower alkyl may be substituted "; a particularly preferred derivative of p- phenoxyphenol is 2-hydroxy-2 ', 4,4'-trichlorodiphenyl ether.

409838/1015

Henkel & CIe GmbH 'sh 13 ", f _e t" t, n ".id _U n"t> 4507 Examples

The production of the new quaternary ammonium compounds of Table I is explained using the following example:

example 1
N-tetradecyl-N-methyl-N- (2-cyanoethyl) -N- (5-chloro-2-hydroxy-

53 g (1 mol) of acrylonitrile were added to the melt of 213 g (1 mol) of tetradecylamine at 65 ° C. under nitrogen over the course of 15 minutes; the mixture was then stirred at 65 ° C. for 2 1/2 hours. Then was added 0.9 g AlCl added as a catalyst and as then added dropwise 92 * 5 g (1 mole) epichlorohydrin, that the temperature did not exceed 80 ⁰ C. After stirring at 60 80 ^° C. for a further 5 hours, unreacted epichlorohydrin and acrylonitrile were distilled off ^{in vacuo (approx. 30 torr) at 50 ° C.} The residual distillation was taken up in 500 ml of isopropyl alcohol and 126 g (1 mol) of dimethyl sulfate were added ^{to this solution at 50-60 ° C.} After stirring for 2 hours at room temperature, the solvent was removed in vacuo and the ammonium salt was obtained as a yellowish solid.

Infrared spectrum (in cm " ¹ ): 335Ο m, 2920 s, 2850 s, 2250 w, 1465 m, I38O w, 1250 s, 1210 s, I060 m, 1010 s, 750 m, 720 w; (s = strong, m = medium, w = weak).

Examples 2 - 5

In analogy to the preparation method described in Example 1, the following compounds of the formula I were also prepared obtain.

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409838/101 5

Henkel & CIe GmbH $ "" 14, " _r τ at.ntonm.idun, d 4507 Example 2

N-Dodecyl-NHflethyl-N - ^ - cyanoathylJ-N - ^^ chlorine ^ -hydroxypropyl) - ammonlumme t hosul fat ____

Infrared spectrum (in cm ): 3 ^ 00 m, 2920 s, 285Ο s, 2250 w, 1465 in, 1580 w, 1250 s, 1210 s, 1060 m, 1010 s, 750 m, 720 w.

N-Hexadecyl-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxy propyl ) -amnionium methosul f a_t

Infrared spectrum (in cm " ¹ ): 230O m, 2920 s, 2850 s, 2250 w, 1465 ra, I38O w, 1250 s, 1210 s, 1040 m, 1010 m, 750 m, 720 w.

Example 4

N-dodecyl-N-methyl-N- (2 -cyanoethyl) -N- (j5 ~ chloro-2-hydroxypr opyl) ammonlumchi or id ________ ^ __ ^

Infrared spectrum (in cm " ¹ ): 325Ο m, 2920 s, 2850 s, 2240 w, 1465 m, 1380 w, 720 w.

Example 5

N-coconut alkyl-N-methyl-N- (2-cyanoethyl) -N- (3-chloro-2-hydroxypropyl ) -ammonyl umchlor ίά

Infrared spectrum (in cm " ¹ ): 328Ο m, 2920 s, 285Ο s, 2240 w, 1465 m, I38O w, 720 w.

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409838/1015

2319818

Henkel & CIe GmbH see below 15>., Poi.ntonm.idun «ο 450?

The following Examples 6-8 describe liquid laundry aftertreatment agents in which the active ingredients of the formula I are used according to the invention. In the packaging of liquid assets of the active ingredient of formula I with the dispersant and, optionally, an organic solvent and, optionally, other additives was at 50 - 60 ⁰ C converted into a homogeneous melt. The acid and optionally the optical brightener were dissolved in water and this aqueous solution was added to the abovementioned melt with vigorous stirring. The preparations obtained in this way are distinguished by good pourability and dispersibility in water. Fragrances and dyes can be added to the preparations.

Example 6

6.0 wt .- # N-dodecyl-N-methyl-N- (2-cyanoethyl) -N- (5-chloro-

2-hydroxypropyl) ammonium chloride;

2.0 wt .- # adduct of oleyl-cetyl alcohol + 5 moles of ethylene oxide; 1.0 wt .- # glycolic acid j
Rest water.

Example 7

.% N-coconut alkyl N-methyl-N- (2-cyanoethyl) -N- (5-chloro-2-hydroxypropyl) ammonium chloride - 6.0 percent;

. 8.0 wt -% isopropyl alcohol;

1.5 wt% adduct of coconut alcohol ( ^C ip- ^C ] .g) ⁺ ^ ^Mo1 ethylene oxide;

0.5 wt% tartaric acid;

. 0.1 wt -% Baurnwollaufheller;

1.0 wt -% of N-benzyl-N-dodecyl-NiN-dimethyl ammonium chloride.

Rest water.

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409838/101 5

Henkel & CIe GmbH su Ig ι » _Γ Pot.nta * meidim _B ο

6.0 wt .- # N-coconut alkyl-N-methyl-N- (2-.cy, anoethyl} -N- (3-

chloro-2-hydroxypropyl) ammonium chloride;

1.5 wt. - ^ adduct of cetyl oleyl alcohol + 5 moles of ethylene oxide; . 0.1 wt -% Baumwollaufheller;

. 0.5 wt -% 2-hydroxy-2 ', 4,4'-trichlordiphenyläther; 0.5% by weight of citric acid;
5.0 % by weight isopropyl alcohol
Rest water.

Be Is pi e 1 9:

15.0 wt. - # N-Dodecyl-N-methyl-N- (2-cyanoethyl) -N- (3-

chloro-2-hydroxypropyl) ammonium chloride;

5.0 wt .- # adduct of C 1 -C 4 fatty alcohol + 12 moles of ethylene oxide;

. 1.5 wt -% glycolic acid;
55.0 wt% urea;
20.5 wt -.% Sodium sulfate (anhydrous).

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409838/1015

Claims (6)

Henkel Λ CIe GmbH wtt. 17 iWtammi ^ D 4507 Claims <,. · ■ »>» ■ · 1. Puartary ammonium salts of the formula I CH ₂ CH ₂ CN R ₁ N
R ₂ in which R, an aliphatic hydrocarbon _{radical with 10-24, preferably 12-18 carbon atoms, R 2} an optionally substituted alkyl radical with 1-4 carbon atoms, R, a chlorine or bromine atom and X ^ an anion from the group of chloride, bromide, hydroxide, Methosulphate and ethosulphate mean. 2. Cuartary ammonium salts according to claim 1, characterized in that that the radical R denotes a straight-chain alkyl radical having 10-24, preferably 12-18, carbon atoms. 3. Process for the preparation of the ammonium salts of the formula I according to Claim 1 and 2, characterized in that _{1 mol of acrylonitrile is added to 1 mol of a primary aliphatic amine R 1} -NH ₂ in the melt, preferably under a protective gas atmosphere, then with 1 Moles of epichlorohydrin or epibromohydrin and catalytic amounts of AlCl- or AlBr, and the tertiary amine thus formed is quaternized with an alkylating agent, optionally with the addition of a solvent. 4. Use of the ammonium salts of the formula I according to claims 1-3 as textile softeners in liquid and powder form Linen aftertreatment agents that also contain at least one Contain diluents and, if necessary, other common ingredients of laundry aftertreatment agents. - 18 409838/1015 Henkel a CIe GmbH su 18 « _U r f <, t« ton _m .id _U n _e ο 4507 5. Use of the ammonium salts of the formula I according to claims 1 - 3 in liquid laundry aftertreatment agents according to claim 4, characterized by the following composition: 2.0-20.0, preferably 5.0-15.0% by weight of the active ingredient Formula I, 0.2 to 6.0, preferably 0.5 - 3 * 0 wt -.% Dispersants, From 0.0 to 30.0, preferably 1.0 - 15 * 0 wt -.% Water-soluble organic solvents, 0.0 - 10.0, preferably 0.3 - 7 * 5 wt .- ^ other usual Components of laundry treatment agents, the remainder is water. 6. Use of the ammonium salts of the formula I according to claims 1-3 in liquid laundry aftertreatment agents according to claim 5 * in which as other common ingredients at least one of the following components in the specified, on the total means related quantities are available: 0.2 to 3.0 wt -.% Antimicrobial agent, 0.2 to 6.0 wt -.% Acidic additives, 0.01 - 0.5 wt .- ^ cotton whitening agent, 0.01 to 0.5 wt -.% Polyamide brighteners, 0.01 to 0.5 wt -.% Fragrance, From 0.00001 to 0.05 wt -.% Dye. 409838/1015