Diquaternary ammonium salts and the use thereof as textile finishing agents

Diquaternary ammonium salts of the formula ##STR1## wherein A.sub.1 and A.sub.2 are each independently of the other C.sub.2 -C.sub.5 alkylene, PA1 Q.sub.1 and Q.sub.2 are each independently of the other --NH-- or --O--, PA1 R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently alkyl, hydroxyalkyl or alkoxyalkyl, each containing 1 to 4 carbon atoms in the alkyl moiety, PA1 Y.sub.1.sup.1.crclbar. is the anion of a strong acid, PA1 Z.sub.1 is C.sub.3 -C.sub.24 alkylene which is substituted by hydroxy and may be interrupted by oxygen atoms and PA1 n is 1 or 2. are suitable for use as textile finishing agents.

The present invention relates to diquaternary ammonium salts, to a process 
for their preparation and to the use thereof as textile finishing agents. 
The diquaternary ammonium salts of this invention are prepared e.g. from 
dialkylaminoalkylbehenic acid amides and aliphatic epoxy compounds and 
therefore contain between the two quaternary nitrogen atoms aliphatic 
bridge members which are always substituted by at least one hydroxyl 
group. 
DE-B-1 092 878 discloses diquaternary ammonium salts which are prepared 
from dialkylaminoalkyl fatty acid amides and an epoxy compound, with the 
starting fatty acids containing at most 18 carbon atoms. The known 
diquaternary ammonium salts are employed as dyeing auxiliaries, in 
particular as levelling agents for dyeings on polyacrylonitrile fibres. 
US-A-4 312 813 also discloses diquaternary ammonium salts which are 
prepared e.g. from dialkylaminoalkylbehenic acid amides and aliphatic 
dihalogen compounds, e.g. .beta.,.beta.'-dibromodiethyl ether, and 
therefore contain between the two quaternary nitrogen atoms aliphatic 
bridge members which are free from hydroxyl substituents. These known 
diquaternary ammonium salts are used in hair cosmetic compositions, in 
particular in shampoos and conditioning rinses. 
Diquaternary ammonium salts have been found which, on account of their 
properties, can be used as textile finishing agents. 
Accordingly, the present invention relates to diquaternary ammonium salts 
of the formula 
##STR2## 
wherein 
A.sub.1 and A.sub.2 are each independently of the other C.sub.2 -C.sub.5 
alkylene, 
Q.sub.1 and Q.sub.2 are each independently of the other --NH-- or --O--, 
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently alkyl, 
hydroxyalkyl or alkoxyalkyl, each containing 1 to 4 carbon atoms in the 
alkyl moiety, 
Y.sub.1.sup.n.crclbar. is the anion of a strong acid, 
Z.sub.1 is C.sub.3 -C.sub.24 alkylene which is substituted by hydroxy and 
may be interrupted by oxygen atoms and 
n is 1 or 2. 
The invention further relates to the preparation of the novel diquaternary 
ammonium salts of this invention by methods known per se and to the use 
thereof as textile finishing agents. 
The alkylene radicals A.sub.1 and A.sub.2 in formula (1) are straight chain 
or branched. Possible representatives are 2,2-dimethylpropylene (also 
referred to as neopentylene), n-butylene (tetramethylene) and, preferably, 
n-propylene (trimethylene) and ethylene. 
Suitable substituents R.sub.1 to R.sub.4 are straight chain or branched 
alkyl radicals, e.g. tert-butyl, isobutyl, n-butyl, isopropyl, n-propyl 
or, preferably, ethyl or methyl. The corresponding hydroxyalkyl radicals, 
e.g hydroxyethyl, are also suitable. The alkoxyalkyl radicals contain 1 to 
4 carbon atoms in both the alkyl moiety and the alkoxy moiety. Thus, 
alkoxyalkyl radicals contain a total of 2 to 8 carbon atoms, e.g. 
methoxyethyl and ethoxyethyl. Unsubstituted alkyl radicals of the type 
indicated above are preferred. 
If n is 1, Y.sub.1.sup.n.crclbar. is the monovalent anion of a strong acid, 
and, if n is 2, Y.sub.1.sup.n.crclbar. is the divalent anion of a strong 
acid. Depending on the meaning of n, the compound of formula (1) contains 
either 1 divalent anion or 2 monovalent anions. 
The mono- or divalent anion of basically any water-soluble inorganic or 
organic acid is a suitable anion Y.sub.1.sup.n.crclbar.. The anion of an 
inorganic acid or of an organic sulfonic acid is preferred. Representative 
examples of such anions are halide, sulfate, methylsulfate or ethylsulfate 
anions, with halide anions, in particular the chloride anion, being of 
special interest. 
The bridge member Z.sub.1 in formula (1) is always substituted by hydroxyl 
groups, preferably by 1 to 4 hydroxyl groups, and may be interrupted by 2 
to 6 oxygen atoms and preferably contains 3 to 24 carbon atoms. Bridge 
members containing e.g. 3 or 4 carbon atoms are preferably substituted by 
1 or 2 hydroxyl groups and are in general not interrupted by oxygen atoms, 
whereas bridge members containing about 8 to 24 carbon atoms are 
preferably substituted by 2, 3 or 4 hydroxyl groups and are preferably 
interrupted by oxygen atoms, most preferably by 2 to 6 oxygen atoms. 
Bridge members of particular interest are derived from an epihalohydrin, 
preferably epichlorohydrin, from an aliphatic diepoxide, preferably a 
diepoxyalkane, e.g. 1,2,3,4-diepoxybutane (also referred to as butadiene 
dioxide) or 1,4-butandediol diglycidyl ether, or form a diglycidyl ether 
obtained from an epihalohydrin, preferably epichlorohydrin, and a lower 
alkylene glycol preferably containing at most 4 carbon atoms, e.g. 
tetramethylene glycol (1,4-butanediol), dimethyl ethylene glycol 
(2,3-butanediol), trimethylene glycol (1,3-propanediol) or, preferably, 
propylene glycol (1,2-propanediol) or, most preferably, ethylene glycol 
(1,2-ethanediol). Such diglycidyl ethers are monomers or oligomers which 
contain 2 to 4 --CH.sub.2 --CH(OH)--CH.sub.2 --O--(C.sub.2 -C.sub.4 
alkylene)--O-- elements or, preferably, 2 to 4 --CH.sub.2 
--CH(OH)--CH.sub.2 --O--(CH.sub.2).sub.2 --O-- elements. 
The two radicals 
##STR3## 
in formula (1) are the radical of preferably technical behenic acid which 
contains a minor amount of e.g. arachic acid and erucic acid and which is, 
in particular, the hydrolysis product of unsaturated C.sub.22 acids from 
colza oil. Such technical behenic acids have a molecular weight in the 
range from about 326 to about 354. 
The bridge members --A.sub.1 --Q.sub.1 -- and --A.sub.2 --Q.sub.2 -- in 
formula (1) are preferably identical. 
Accordingly, preferred diquaternary ammonium salts are of the formula 
##STR4## 
wherein 
R.sub.5 and R.sub.6 are each independently of the other C.sub.1 -C.sub.4 
alkyl, 
Y.sub.2.sup.n.crclbar. is the anion of an inorganic acid or of a sulfonic 
acid, 
Z.sub.2 is C.sub.3 -C.sub.24 alkylene which is substituted by 1 to 4 
hydroxyl groups and which may be interrupted by oxygen atoms and 
A.sub.1, Q.sub.1 and n are as defned. 
Depending on the number of carbon atoms, the alkylene chain in Z.sub.2 may 
be interrupted by 2 to 6 oxygen atoms. 
The C.sub.1 -C.sub.4 alkyl substituents in formula (2) are preferably 
identical. Accordingly, ammonium salts of particular interest are of the 
formula 
##STR5## 
wherein Y.sub.3.sup.n.crclbar. is a halide, sulfate, methylsulfate or 
ethylsulfate anion, 
Z.sub.3 is C.sub.3 -C.sub.4 alkylene which is substituted by 1 or 2 
hydroxyl groups, or Z.sub.3 is C.sub.8 -C.sub.24 alkylene which is 
substituted by 2 to 4 hydroxyl groups and which is interrupted by 2 to 6 
oxygen atoms and 
A.sub.1, Q.sub.1, R.sub.5 and n are as defined. 
Ammoniums salts which are particularly suitable for use as textile 
finishing agents are those of the formula 
##STR6## 
wherein A.sub.3 is ethylene, n-propylene, n-butylene or 
2,2-dimethylpropylene, 
Q.sub.1 is --NH-- or --O--, 
R.sub.7 is methyl, ethyl or isopropyl and 
Z.sub.4 is --CH.sub.2 --CH(OH)--CH.sub.2 --, --CH.sub.2 
--CH(OH)--CH(OH)--CH.sub.2 -- or --CH.sub.2 --CH(OH)--CH.sub.2 
--O(CH.sub.2).sub.4 --O--CH.sub.2 --CH(OH)--CH.sub.2 --. 
Particularly interesting diquaternary ammonium salts are those of the 
formula 
##STR7## 
and, especially, of the formula 
##STR8## 
in which formulae A.sub.3, Q.sub.1 and R.sub.7 are as defined. 
The diquaternary ammonium salts of formula (1) are prepared by methods 
known per se, e.g. by reacting 
1 mole of a dialkylaminoalkylbehenic acid amide or ester of the formula 
##STR9## 
wherein A.sub.1, Q.sub.1, R.sub.1 and R.sub.2 are as defined, and 
1 mole of a dialkylaminoalkylbehenic acid amide or ester of the formula 
##STR10## 
wherein A.sub.2, Q.sub.2, R.sub.3 and R.sub.4 are as defined, with about 1 
mole of an epoxy compound of the formula 
EQU (9) X.sub.1 --Z'--X.sub.2 
wherein 
X.sub.1 is an epoxy group 
##STR11## 
X.sub.2 is an epoxy group or a mobile halogen atom and 
Z' is C.sub.1 -C.sub.20 alkylene which is unsubstituted or substituted by 
hydroxy and which may be interrupted by oxygen atoms, or, if X.sub.2 is an 
epoxy group, Z' is also the direct bond, in the presence of a strong acid 
of the formula 
EQU (10) H.sub.n.sup..sym. Y.sub.1.sup.n.crclbar. 
wherein Y.sub.1.sup.n.crclbar. and n are as defined. 
The ammonium salts of formula (2) are prepared by reacting about 2 moles of 
a dialkylaminobehenic acid amide or ester of the formula 
##STR12## 
wherein A.sub.1, Q.sub.1, R.sub.5 and R.sub.6 are as defined, with about 1 
mole of an epoxy compound of the formula 
EQU (12) X.sub.1 --Z"--X.sub.2 
wherein X.sub.1 and X.sub.2 are as defined and Z" is C.sub.1 -C.sub.20 
alkylene which is unsubstituted or substituted by 1 or 2 hydroxyl groups 
and which may be interrupted by 2 to 6 oxygen atoms, or, if X.sub.2 is an 
epoxy group, Z" is also the direct bond, in the presence of an acid of the 
formula 
EQU (13) H.sub.n.sup..sym. Y.sub.2.sup.n.crclbar. 
wherein Y.sub.2 and n are as defined. 
The ammonium salts of formula (3) are prepared by reacting about 2 moles of 
a dialkylaminoalkylbehenic acid amide or ester of the formula 
##STR13## 
wherein A.sub.1, Q.sub.1 and R.sub.5 are as defined, with about 1 mole of 
an epoxy compound of the formula 
EQU (15) X.sub.1 --Z'"--X.sub.2 
wherein X.sub.1 and X.sub.2 are as defined and Z'" is methylene, or, if 
X.sub.2 is an epoxy group, Z'" is the direct bond or C.sub.4 -C.sub.20 
alkylene which is interrupted by 2 to 6 oxygen atoms and which is 
unsubstituted or substituted by 1 or 2 hydroxyl groups, in the presence of 
an acid of the formula 
EQU (16) H.sub.n.sup..sym. Y.sub.3.sup.n.crclbar. 
wherein Y.sub.3 and n are as defined. 
The ammonium salts of formula (4) are prepared by reacting about 2 moles of 
a dialkylaminoalkylbehenic acid amide or ester of the formula 
##STR14## 
wherein A.sub.3, Q.sub.1 and R.sub.7 are as defined, with 1 mole of 
epichlorohydrin, 1,2,3,4-diepoxybutane, 1,4-butanediol diglycidyl ether or 
a diglycidyl ether which is obtained from ethylene glycol and 
epichlorohydrin, in the presence of an acid of the formula 
EQU (18) H.sup..sym. Y.sub.4.sup..crclbar. 
wherein Y.sub.4.sup..crclbar. is as defined. 
The dialkylaminoalkylbehenic acid amides or esters of formulae (7), (8), 
(11), (14) and (17) are known per se and are prepared by known methods, 
namely by reacting behenic acid with approximately equimolar amounts of 
corresponding dialkylaminoalkylamines or dialkylaminoalkanols at a 
temperature above 100.degree. C., e.g. in the range from 150.degree. to 
180.degree. C., with removal of the water of reaction from the reaction 
mixture. 
The reaction of the compounds of formulae (7), (8) and (9) in the presence 
of an acid of formula (10) is preferably carried out at elevated 
temperature, e.g. in the range from 50.degree. to 90.degree. C., in 
general in aqueous medium and, if desired, in the presence of a polar 
solvent, preferably in the presence of a low molecular amide or ether, 
e.g. dimethylformamide or diethylene glycol monobutyl ether, or, most 
preferably, in the presence of a low molecular alkanol, e.g. ethanol or, 
preferably, butyl glycol or, most preferably, isopropanol. In their 
application as textile finishing agents, the ammonium salts of this 
invention are employed as waterproofing agents, anti-crease agents, 
softeners or agents for improving the sewability, the spinning performance 
or the soiling behaviour of textiles. 
The textile materials to be finished in accordance with this invention may 
be in any state of processing, i.e. in the form of yarns, staple fibres, 
continuous threads, nonwovens or, in particular, in the form of wovens or 
knits. The materials may be dyed or undyed, may or may not have been 
treated with fluorescent whitening agents or may be in the form of refined 
garments. 
Suitable textile fibres are fully synthetic, regenerated and natural 
fibres. Mixtures of synthetic and natural fibres are also suitable. 
Examples of synthetic fibres are artificial silk, rayon staple, viscose, 
cellulose diacetate, cellulose triacetate, polyacrylonitrile, 
acrylonitrile heteropolymers, polyamide, in particular fibres made from 
poly-2-caprolactam, polyhexylmethylenediamide adipate or 
poly-.omega.-aminoundecanoic acid, and polyesters, in particular fibres 
which are derived from terephthalic acid, e.g. poly(ethylene glycol 
terephthalate) or poly(1,4-cyclohexylenedimethylene terephthalate). 
Examples of natural fibres are linen, hemp, ramie, wool and cotton. 
Preferred textile materials to be finished are wool, polyacrylonitrile, 
polyamide polyester or cotton wovens or knits and also woven or knits made 
from blends of these fibres. 
When finishing the textile materials, formulations containing a 
diquaternary ammonium salts of this invention are applied to said textile 
materials by customary methods. The formulations may for example be 
sprayed or slop-padded onto the textile materials. However, the textile 
materials are preferably padded with the formulations or treated by the 
exhaust process. Application is effected at room temperature or at 
elevated temperatures, e.g. in the range from 30.degree. to 100.degree. 
C., for about 5 to 120 minutes. The textile materials are subsequently 
dried at room temperature or, preferably, at elevated temperature, i.e. in 
the range from about 50.degree. to 150.degree. C. 
The diquaternary ammonium salts of the invention are conveniently employed 
in amounts of 0.05 to 5% by weight, preferably 0.1 to 4% by weight, based 
on the textile material to be finished. 
It is a substantial advantage of the diquaternary ammonium salts of the 
present invention that they produce good finishing effects of the various 
types described above which can be utilised in a large variety of textile 
materials. Moreover, the good compatibility of the diquaternary ammonium 
salts with fluorescent whitening agents, dyes, and auxiliaries and 
adjuvants customarily employed in the textile industry, e.g. surfactants, 
is a further advantage. 
In the following preparatory procedures and Examples, parts and percentages 
are by weight. 
PROCEDURES FOR THE PREATION OF DIALKYLAMINOALKYLBEHENIC ACID AMIDES OR 
ESTERS 
Procedure A 
In an inert nitrogen atmosphere, 56.1 parts (0.55 mole) of 
dimethylaminopropylamine are added over 90 minutes at 160.degree. C. to a 
melt consisting of 166 parts (0.5 mole) of a technical behenic acid which 
has a molecular weight of 332. The reaction mixture is subsequently heated 
to 170.degree. C. and then held, with stirring, for 5 hours at this 
temperature, with the water of reaction being removed from the reaction 
mixture. Dimethylamino-n-propylbehenic acid amide with an amine value of 
128 and an acid value of 0 is obtained in virtually quantitative yield. 
Procedures B to F 
The dialkylaminoalkylbehenic acid amides or esters which are listed in 
Table 1 below and which have the corresponding amine values are obtained 
in analogous manner by reacting behenic acid with the 
dialkylaminoalkylamines or dialkylaminoalkanols also listed in Table 1. 
TABLE I 
______________________________________ 
Dialkylaminoalkylamine 
Dialkylaminoalkyl 
Pro- or acid amide or Amine 
cedure 
dialkylaminoalkanol 
ester value 
______________________________________ 
B dimethylaminoethylamine 
dimethylaminoethyl- 
131.7 
behenic acid amide 
C dimethylamino-n-pro- 
dimethylamino-n- 
138.6 
panol propylbehenic acid 
ester 
D diethylaminoethylamine 
diethylaminoethyl- 
134 
behenic acid amide 
E dimethylaminoneopentyl- 
dimethylaminoneo- 
122 
amine pentylbehenic acid 
amide 
F diisopropylaminoethyl- 
diisopropylamino- 
132 
amine ethylbehenic acid 
amide 
______________________________________

PREATORY EXAMPLES FOR THE DIQUATERNARY AMMONIUM SALTS OF THE PRESENT 
INVENTION 
EXAMPLE 1 
A solution of 12.3 g of concentrated hydrochloric acid in 73 g of water and 
43 g of isopropanol is added at 60.degree. C. to 106.25 g (0.25 mole) of 
dimethylaminoethylbehenic acid amide obtained according to Preparatory 
Procedure B. 11.6 g (0.125 mole) of epichlorohydrin are then added over 15 
minutes, and the temperature is subsequently increased to 75.degree. C. 
With stirring, the reaction solution is held at this temperature for 10 
hours, after which time the amine and epoxide values are 0. The reaction 
solution is then evaporated to dryness, affording 122 g of the 
diquaternary ammonium compound of the formula 
##STR15## 
Melting interval: 70.degree.-98.degree. C. 
EXAMPLE 2 
A solution of 12.3 g of concentrated hydrochloric acid in 73 g of water and 
43 g of isopropanol is added at 60.degree. C. to 101 g (0.25 mole) of 
dimethylamino-n-propylbehenic acid ester obtained according to Procedure 
C. 11.6 g (0.125 mole) of epichlorohydrin are then added over 15 minutes, 
and the temperature is subsequently increased to 75.degree. C. With 
stirring, the reaction solution is held at this temperature for 10 hours, 
after which time the amine and epoxide values are 0. The reaction product 
is then evaporated to dryness, affording 117 g of the diquaternary 
ammonium compound of the formula 
##STR16## 
Melting interval: 76.degree.-84.degree. C. 
EXAMPLE 3 
A solution of 12.3 g of concentrated hydrochloric acid in 73 g of water and 
43 g of isopropanol is added at 60.degree. C. to 104.5 g (0.25 mole) of 
diethylaminoethylbehenic acid amide obtained according to Procedure D. 
11.6 g (0.125 mole) of epichlorohydrin are then added over 15 minutes, and 
the temperature is subsequently increased to 75.degree. C. With stirring, 
the reaction solution is held at this temperature for 10 hours, after 
which time the amine and epoxide values are 0. The reaction solution is 
then evaporated to dryness, affording 120 g of the diquaternary ammonium 
compound of the formula 
##STR17## 
Melting interval: 57.degree.-60.degree. C. 
EXAMPLE 4 
109.75 g (0.25 mole) of dimethylamino-n-propylbehenic acid amide obtained 
according to Procedure A are dissolved, with heating, in 44 g of 
isopropanol, and then a solution of 12.3 g of concentrated hydrochloric 
acid in 74 g of water is added. 11.6 g (0.125 mole) of epichlorohydrin are 
added over 15 minutes at 55.degree. C., and the temperature of the 
reaction solution is subsequently increased to 75.degree. C. With 
stirring, the reaction solution is held at this temperature for 3 hours, 
after which time the amine and epoxide values are 0. 
251 g of a 50% reaction solution of the diquaternary ammonium compound of 
the formula 
##STR18## 
are obtained, which solution is wax-like at room temperature. Melting 
interval: 85.degree.-162.degree. C. 
EXAMPLE 5 
65.6 g (0.15 mole) of dimethylamino-n-propylbehenic acid amide obtained 
according to Procedure A are melted at 80.degree. C., and 14.8 g of 37% 
hydrochloric acid in 758.6 g of water are added to the resultant melt. 
16.35 g (0.075 mole) of 1,4-butanediol diglycidyl ether with an epoxide 
value of 4.6 are added over 10 minutes at 60.degree. C. to the reaction 
mixture. Subsequently, the reaction mixture is heated to 70.degree. C. 
and, with stirring, held at this temperature for 1 hour, after which time 
the amine and epoxide values are 0. 
855 g of a 10% solution of the diquaternary ammonium salt of the formula 
##STR19## 
are obtained. 
EXAMPLE 6 
65.6 g (0.15 mole) of dimethylamino-n-propylbehenic acid amide obtained 
according to Procedure A are melted at 80.degree. C., and 5.1 g of 
sulfuric acid in 1083.6 g of water are added to the resultant melt. 16.35 
g (0.075 mole) of 1,4-butanediol diglycidyl ether with an epoxide value of 
4.6 are added over 10 minutes at 60.degree. C. The reaction mixture is 
subsequently heated to 70.degree. C. and, with stirring, held at this 
temperature for 10 hours, after which time the amine value is 28 and the 
epoxide value 0. 
1170 g of a 7% solution containing mainly the diquaternary ammonium salt of 
the formula 
##STR20## 
are obtained. 
EXAMPLE 7 
45.8 g (0.1 mole) of dimethylaminoeopentylbehenic acid amide obtained 
according to Procedure E are heated together with 9.9 g of concentrated 
hydrochloric acid in 500.4 g of water to a temperature of 75.degree. C. 
Then 10.9 g (0.05 mole) of 1,4-butanediol diglycidyl ether with an epoxide 
value of 4.6 are added over 15 minutes. The reaction mixture is stirred 
for 12 hours at 77.degree.-78.degree. C., after which time the amine and 
epoxide values are 0. 
567 g of a 10% solution of the diquaternary ammonium salt of the formula 
##STR21## 
are obtained. 
EXAMPLE 8 
42.3 g (0.1 mole) of diisopropylaminoethylbehenic acid amide obtained 
according to Procedure F are heated together with 9.9 g of concentrated 
hydrochloric acid in 479.8 g of water to a temperature of 75.degree. C. 
Then 10.9 g (0.05 mole) of 1,4-butanediol diglycidyl ether with an epoxide 
value of 4.6 are added over 15 minutes. The reaction mixture is stirred 
for 12 hours at 75.degree. C., after which time the amine and epoxide 
values are 0. 
542 g of a 10% solution of the diquaternary ammonium salt of the formula 
##STR22## 
are obtained. 
APPLICATION EXAMPLES 
EXAMPLE 9 
1 kg of cotton tricot fabric is treated by the exhaust process for 20 
minutes at 40.degree. C. (liquor to goods ratio 1:30) with a liquor which 
contains 4% of the diquaternary ammonium salt of Example 4 and which, 
after the addition of acetic acid, has a pH value of 5.5. the fabric is 
subsequently dried without rinsing. In order to test the sewability, a 50 
cm seam is sewn onto the fabric with a sewing machine (Overlock Union 
Special Type 39500) at a rate of 6000 stitches per minute using a 
polyester long fibre sewing thread. A needle with a size 70 point is used. 
The number of holes along the seam is assessed in comparison with an 
untreated cotton tricot fabric. The results are summarized in Table II 
below: 
TABLE II 
______________________________________ 
Substrate Number of holes 
______________________________________ 
treated tricot fabric 
2 
untreated tricot fabric 
19 
______________________________________ 
Similar results are also achieved by padding the cotton tricot fabric to 
100% pick-up at room temperature (15.degree. to 25.degree. C.) with a 
liquor containing 40 g/l of the diquaternary ammonium salt of Example 4 
and 2 g/l of 80% acetic acid, and subsequently drying the fabric at 
90.degree. C. 
EXAMPLE 10 
The knits tested in Example 9 for sewability are subjected to a soiling 
test. The soiling in dry state is assessed in accordance with the 
following test: 
______________________________________ 
substrate; size 
9 .times. 12 cm (several samples) 
filter dust 15% (based on the weight of the goods) 
apparatus Turbula 
test duration 
30 minutes 
vacuum-cleaned 
______________________________________ 
The results are summarized in the following Table III 
TABLE III 
______________________________________ 
Substrate Soiling 
______________________________________ 
tricot fabric treated none 
in acc. with Example 6 
untreated tricot fabric a little 
______________________________________ 
EXAMPLE 11 
In a winch vat, 100 g of cotton tricot fabric are pretreated at 50.degree. 
C. in 4000 liters of water containing a commercially available wetting 
agent. 
3 kg of a dye of the formula, 
##STR23## 
8 kg of sodium m-nitrobenzenesulfonate and, 
4 kg of the diquaternary ammonium salt of Example 4 are then added. 
After the uniform distribution of these additives, 
160 kg of sodium chloride 
are added by degrees, and the temperature is increased to 80.degree. C. 
Subsequently, 
12 g of a 30% sodium hydroxide solution are added. 
After a further 45 minutes at 80.degree. C., the tricot fabric is rinsed 
with hot and then with cold water and subsequently washed for 20 minutes 
at boiling temperature with 4000 liters of a liquor (liquor to goods ratio 
1:40) containing 4 kg of an adduct of 1 mole of nonlyphenol and 9 moles of 
ethylene oxide and 4 kg of the diquaternary ammonium salt of Example 4. 
The fabric is then again rinsed and dried. Applying the Monsanto scale as 
a measure of the crease resistance of the treated tricot fabric, grade 4 
is obtained. If the tricot is treated as described above but without the 
addition of the diquaternary ammonium salt in the dye bath or washing 
liquor, grade 2 according to the Monsanto scale is obtained. 
EXAMPLE 12 
20 g of bleached cotton terry cloth with a weight per unit area of 330 
g/m.sup.2 is treated for 5 minutes at 20.degree. C. with 400 ml of water 
of 5.degree. dH (German hardness degree) containing 0.02 g of the 
diquaternary ammonium salt of Example 4. The terry cloth is subsequently 
centrifuged without rinsing and then dried at 70.degree. C. The following 
textile materials are also subjected to the same treatment: 
(a) viscose filament yarn 
(b) chlorinated woollen cabled yarn 
(c) staple fibre polyamide yarn 
(d) high-bulk staple fibre polyacrylonitrile yarn. 
The handle of the treated textile materials is assessed in accordance with 
the following scale: 
0=handle unchanged 
1=somewhat softer than 0 
2=markedly softer than 0 
3=much softer than 0 
4=very much softer than 0 
The results are summarized in Table IV below: 
TABLE IV 
______________________________________ 
Treated with 
Substrate Untreated ammonium salt 
______________________________________ 
cotton terry cloth 
0 2-3 
viscose filament yarn 
0 4 
woollen cabled yarn 
0 2 
polyamide yarn 0 3-4 
polyacrylonitrile yarn 
0 3-4 
______________________________________ 
Similar results are obtained with the diquaternary ammonium salts of 
Examples 1, 2, 3 or 5 to 8. 
Example 13 
A washing machine with a capacity of about 4 kg is filled with the 
following material: 
______________________________________ 
300 g of bleached cotton terry cloth 
(weight per unit area: 330 g/m.sup.2) 
300 g of bleached mercerised cotton tricot fabric 
(weight per unit area: 150 g/m.sup.2) 
300 g of viscose taffeta 
(weight per unit area: 105 g/m.sup.2) 
300 g of polyamide 6,6 helanca tricot fabric, type HE 
(weight per unit area: 260 g/m.sup.2) 
300 g of polyester crimplene tricot fabric 
(weight per unit area: 225 g/m.sup.2) 
300 g of polyacrylonitrile tricot fabric, type 42 
(weight per unit area: 330 g/m.sup.2) 
1800 g 
______________________________________ 
The contents of the machine are washed at 40.degree. C. with 80 g of a 
commercially available detergent. The hardness of the water is about 
10.degree. dH. For the final rinse (=20 l) a solution of 2 g of the 
diquaternary ammonium salt of Example 4 in 200 ml of water is added, and 
the textile material is treated with said solution for 5 minutes. The 
textile material is subsequently centrifuged and dried at 70.degree. C. 
The handle of the textile materials thus treated is assessed in accordance 
with the scale indicated in Example 12. The results are summarized in 
Table V below: 
TABLE V 
______________________________________ 
Treated without 
Treated with 
Substrate ammonium salt ammonium salt 
______________________________________ 
cotton terry cloth 
0 3 
cotton tricot fabric 
0 2-3 
viscose taffeta 
0 2-3 
polyamide tricot fabric 
0 2 
polyester tricot fabric 
0 2 
polyacrylonitrile tricot 
0 4 
fabric 
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