CH672220B5 - - Google Patents

Abstract

New bis-imidazolium salts are of formula (I): (where Q = a divalent 4-12C aliphatic hydrocarbon gp., opt. with OH substits., having a hydantoin gp. in the chain; X1 and X2 independently = glycidyl or -CH2-CH(OH)-CH2-Hal gps.; Hal = halogen; R1 and R2 independently = H, Ph or an aliphatic gp.; n = 1 or 2; Y = an (in)organic anion; imidazole rings A and B independently may have unsubstd. or halogen-, OH- or CN-substd. lower alkyl substits. in the 4- and/or 5-positions.) The material is treated with (I) by the slop padding process, pref. continuously after or esp. during dyeing; continuously by the slop padding/cold dwell technique, pref. during dyeing; or by the exhaustion method. (I) is prepd. by conventional methods, by reacting a mole bis-imidazole cpd. (II) or pref. its salts, e.g. with HCl or H2SO4, with 2 mole epihalohydrin (epibromohydrin or pref. epichlorohydrin). USE/ADVANTAGE - (I) are used for increasing the dyeing yield and wet fastness of dyeing and prints produced with anionic dyestuffs on cellulose fibre material, by treating the material with (I) before, during or after dyeing or printing. It is useful for treating natural cellulose (staple rayon, viscose rayon, hemp, linen, jute and esp. cotton) and mixt., e.g. polyamide/cotton, and cellulose acetate in any form, e.g. yarn and woven, knitted and nonwoven fabrics.

Description

DESCRIPTION 50 The present invention relates to bis-imidazolium salts and their use as auxiliaries for the production of dyeings or prints on cellulose fiber material with anionic dyes.

The bis-imidazolium salts according to the invention are water-soluble bis-imidazolium compounds, the imidazole components of which are connected to one another via a bridge member in the 1-position and have fiber-reactive groups in the 3-position which are formed by adding epihalohydrin. They correspond to the formula

60

(1)

1

r.

I.

R "

2 ©

2y ti0

n

672 220 G.

Woellll

Q is a divalent chain which is interrupted in the chain by a hydantoin group and, if necessary, by hy-

droxylgmppen substituted aliphatic Kolilenwasser-

material residue with 4 to 12 carbon atoms,

Xi and X2, independently of one another, the group

-CH -CH-CH or preferably -CH -CH-CH2-Hal

2 V 1

OH

Shark a halogen atom,

Ri and R2, independently of one another, are hydrogen, phenyl or an aliphatic radical,

n 1 or 2 and

Y® is an anion of an inorganic or organic acid and the imidazole rings A and B, independently of one another, are unsubstituted or substituted by unsubstituted or substituted by halogen, hydroxyl or cyano.

Halogen in combination with all of the above and below substituents means, for example, bromine, fluorine, iodine or preferably chlorine.

The imidazole constituents, including the fiber-reactive groups Xi and X2 are preferably identical, wherein Xi and X2 are primarily halohydrin groups of the formula

(la) -CH0-CH-CH -Hai

2 1 2 1

OH

(2)

ch2-n.

10th

Propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl or tert.amyl.

If any lower alkyl radicals are substituted, this is how it is done. are mainly haloalkyl, cyanoalkyl or Hy-15 hydroxyalkyl, each having 2 to 4 carbon atoms, such as. B. 2-chloroethyl, 2-cyanoethyl, 2-hydroxyethyl or 3-hydroxypropyl.

The hydantoin group present in the bridge member Q is expediently connected to the hydrocarbon radical by the nitrogen atoms and can be unsubstituted in the a position or substituted by one or two lower alkyl groups, especially methyl.

Q is preferably an alkylene radical in the chain which is interrupted by a hydantoin group and is optionally substituted by 25 hydroxyl groups and has 6 to 10 carbon atoms.

The hydantoin group is preferably derived from hy-dantoin, a-methylhydantoin or especially a-dimethylhy-dantoin. A particularly preferred bridge member Q is

30th

where Hali is bromine or preferably chlorine.

As an aliphatic radical, R 1 and R 2 can be saturated or unsaturated, straight-chain or branched and have up to 23 carbon atoms. Ri and R2 are advantageously an alkyl radical having 1 to 23 carbon atoms.

Examples of such alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-amyl, isoamyl, hexyl, heptyl, octyl, isooctyl, nonyl, isononyl, undecyl, dodecyl, tridecyl, pentadecyl , Heptadecyl, nonadecyl, heneico-syl or tricosyl.

Rj and R2 are preferably hydrogen, phenyl, lower alkyl, undecyl or heptadecyl.

Lower alkyl generally represents such groups or group components which have 1 to 5, in particular 1 to 3, carbon atoms, such as, for. B. methyl, ethyl, n-

35

CH.

-CHa-grV

Anions Y® are both anions of inorganic acids, such as. B. the chloride, bromide, fluoride, iodide, sulfate or phosphate ion as well as anions of organic acids, for. B. aromatic or aliphatic sulfonic acids, such as. B. benzenesulfonate, p-toluenesulfonate, chlorobenzenesulfonate, methane or ethanesulfonate ion, also the 45 anions of lower carboxylic acids, such as. B. acetate, propionate or oxalate ion.

Y® is primarily the chloride, bromide or sulfate ion.

Practically important bis-imidazolium salts correspond to the formula

50

V "-

A.

I D I

-Nx ^ N-CH

L

2nd

CH-OH

CH-OH ÌH2 halx

CH2-Hal1

, 0

2y nQ

where Halj, n and Y® have the meaning given,

Qi is a divalent alkylene radical in the chain which is bonded to the N atoms and optionally substituted in the a-position by methyl and optionally substituted by hydroxyl groups and has 6 to 10 carbon atoms and

R3 is hydrogen, phenyl or alkyl having 1 to 17 carbon atoms and ring D is unsubstituted or substituted by methyl or ethyl.

Bis-imidazolium salts of the formula are of particular interest

5

672 220 G.

\

(3)

I i

2 \

l ch „-n ^

ch-oh ch2-ci

n .n-ch,

\ / k ch-oh

CH2 ~ C1J

, ©

2Y

n0

n where

Q2 an alkylene radical with 6 to 10 carbon atoms in the chain which is bonded to the N atoms and is interrupted in the a-position by methyl substituted hydantoin group and optionally substituted by hydroxyl groups,

R4 is hydrogen, phenyl or alkyl of 1 to 11 carbon atoms

Z is hydrogen or methyl,

n 1 or 2 and

Yie that means chloride or sulfate ion.

Among these bis-imidazolium salts of the formula (3), those in which R4 is hydrogen or methyl, Z is hydrogen and Yie is the chloride or sulfate ion are particularly preferred.

The bis-imidazolium salts are prepared in a manner known per se. The preparation can preferably be carried out by adding 1 mol of a bis-imidazole compound of the formula

(4)

I À I I B I

L

l wherein A, B, Q, Rj and R2 have the meaning given, or preferably their acid salt z. B. with hydrochloric acid or sulfuric acid, with 2 moles of an epihalohydrin, such as. B. epibromohydrin or preferably epichlorohydrin.

(5a)

A

H

20th

25th

35

The reaction conditions for the preparation of the bis-imidazolium salts are to be selected such that there is no premature exchange of mobile substituents either as a result of the pH values of the reaction medium being too high or as a result of the temperature being too high. It is therefore preferred to work in a dilute, aqueous medium under the most gentle temperature and pH conditions, expediently at a temperature of 30 to 95 ° C. and a pH of 5 to 8, preferably 5.5 to 7, in order to achieve the desired pH Worth a hydrohalic acid, such as. B. hydrochloric acid or sulfuric acid can be added.

The reaction of the bis-imidazole compounds with the epihalohydrin can also be carried out by heating the components to temperatures of 40 to 95 ° C., if appropriate also in an organic solvent.

Suitable organic solvents that form the reaction medium are aliphatic lower alcohols, such as. As methanol, ethanol, propanol or isopropanol, cycloaliphatic or preferably aromatic hydrocarbons, such as. B. cyclohexane, benzene, toluene or xylene; Chlorinated hydrocarbons, such as B. ethylene chloride, tetrachlorethylene, cyclic ethers, such as. B. dioxane or tetrahydrofuran; Dimethyl sulfoxide or nitriles of aliphatic monocarboxylic acids, such as. B. acetonitrile, propionitrile or butyro-nitrile. Mixtures of the solvents mentioned can also be used.

The bis-imidazole compounds of the formula (4) which can be used as starting materials can be prepared in high yield and purity by adding 1 mol of an imide-azole compound of the formulas and

Lb / -r *

H

(5b)

or 2 moles of the same imidazole compound with a compound corresponding to Q and having two functional groups, such as. B. 1,3-diglycidylhydantoins.

As imidazole components for the preparation of the bis-imidazole compounds of the formula (4) come, for. B. Imid-azole, 2-methylimidazole, 2-ethylimidazole, 2-isopropylimide-azole, 2,4-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-heptylimidazole, 2-phenyl-4-methyl- imidazole, 2-undecylimidazole, 4-methyl-2-undecylimidazole, 4,5-dimethyl-2-undecylimidazole, 4-ethyl-2-undecylimidazole, 2-heptadecylimidazole, 4-cyanoethyl-2-methylimidazole, 4-cyanoethyl 2-undecylimidazole and the corresponding acid salts.

2-methylimidazole, 2-phenylimidazole and especially imidazole are particularly preferred.

Examples of Q-introducing compounds with two functional groups are: 1,3-diglycidylhydane

55

60

toin, l, 3-diglycidyl-4-methyl-hydantoin or 1,3-diglycidyl-4-dimethyl-hydantoin.

Bis-imidazolium salts according to the invention are particularly suitable as auxiliaries for improving the color yield and the wet fastness of dyeings or prints which are produced on cellulose fiber materials with anionic dyes.

The treatment of the cellulose fiber material with the cationic bis-imidazole compound is preferably carried out continuously using a padding process. The cellulose fiber material is impregnated with the fixing agent, e.g. B. by padding, and then subjected to a fixing process. This application can be carried out before dyeing, during dyeing or after dyeing. Treatment after or in particular during dyeing is preferred. The aftertreatment can be carried out both on dyeings and on color prints.

672 220 G.

6

The impregnation step can be carried out at 20 to 70 ° C, but preferably at room temperature. The fixing step can be carried out by a steaming process, a thermosoling process, a microwave treatment or a warm or cold residence process.

In the steaming process, the textile materials which have been sealed with the treatment liquor are subjected to a fixing treatment in a steamer with possibly superheated steam, advantageously at a temperature of 98 to 130 ° C., preferably 102-110 ° C.

The fixation by the so-called Thermosolierpro-process, after or without intermediate drying, for. B. at a temperature of 100 to 210 ° C. The thermal insulation is preferably carried out at a temperature of 120 to 210 ° C, preferably 140 to 180 ° C and after intermediate drying at 80 to 120 ° C of the padded or printed goods. Depending on the temperature, the thermal insulation can take 20 seconds to 5 minutes, preferably 30 to 180 seconds.

The heat setting can also be carried out using microwaves. After impregnation with the treatment liquor and squeezing off the excess moisture, the goods are expediently rolled up and treated in a chamber by means of microwaves. This microwave treatment can take 2 to 120 minutes. Preferably 2 to 15 minutes will suffice. Microwaves are electromagnetic waves (radio waves) in the frequency range from 300 to 100,000 MHz, preferably 1000 to 30,000 MHz.

In the warm dwell process, the padded or printed goods are left in a moist state, e.g. B. 15 to 120 minutes, advantageously at temperatures of 85 to 102 ° C. The impregnated goods can be preheated to 85 to 102 ° C by infrared treatment. The residence temperature is preferably 90 to 100.degree.

The fixing step can also be carried out according to the cold dwell process by storing the padded or printed and preferably rolled-up goods at room temperature from 15 to 30 ° C. B. during 3 to 24 hours. If necessary, it can also be stored at a slightly elevated temperature (30 to 80 ° C).

The treatment with the bis-imide-azolium salts is preferably carried out according to the block-cold residence method and in particular during the dyeing.

The continuous treatment after dyeing is preferably carried out by padding the dyed or printed fiber material with the subsequent thermal insulation process.

The treatment of the textile materials with the bis-imide-azolium salts can also be carried out in the exhaust process before or after the dyeing, but especially during the dyeing. In this case you can work at temperatures in the range of 20 to 135 ° C, preferably 40 to 100 ° C. The liquor ratio can be chosen within a wide range, e.g. B. 1: 2.5 to 1: 100, preferably 1: 5 to 1:40.

The treatment liquors contain the bis-imidazolium salts in the exhaust process, preferably in an amount of 1 to 25% by weight, in particular 2 to 15% by weight, based on the weight of the cellulose fiber material, or 1 to 100 g / l in padding liquors or printing pastes , preferably 10 to 50 g / 1, the squeezing effect in the padding process advantageously being 60 to 120% by weight.

The dyes used are the substantive dyes or reactive dyes which can usually be used for dyeing cellulose textile materials.

The usual direct dyes are suitable as substantive dyes, for example the “Direct Dyes” in Color Index, 3rd edition (1971) Volume 2 on pages 2005-2478.

Reactive dyes are understood to be the usual dyes which form a chemical bond with the cellulose, e.g. B. The “reactive dyes” listed in Color Index, Volume 3 (3rd edition, 1971) on pages 3391-3560 and in Volume 6 (revised 3rd edition, 1975) on Pages 6268-6345.

In the case of simultaneous dyeing and treatment with the bis-imidazolium salts, the amount of the dyes generally depends on the desired color strength and is expediently from 0.1 to 100 g per liter of liquor, preferably from 5 to 60 g / 1 liquor, in the continuous process. In the exhaust process, the amount of dye is advantageously 0.1 to 10% by weight, preferably 1 to 6% by weight.

In addition to the cationic bis-imidazolium salts, the liquors also contain alkaline compounds, such as. As sodium carbonate, sodium bicarbonate, sodium hydroxide, disodium phosphate, trisodium phosphate, borax, aqueous ammonia or alkali donors, such as. B. sodium trichloroacetate or sodium formate.

The pH of the treatment or dyeing liquors is therefore usually 8 to 13.5, preferably 8.5 to 13.

If desired, the liquors can also urea, glycerol, electrolytes, such as. B. sodium chloride or sodium sulfate, alkali-resistant wetting agents, homopolymers or copolymers of acrylamide or methacrylamide or graft polymers, as described in EP-A-111 454, and also thickeners, such as. B. Algi-nate, starch ether or locust bean flour ether.

The bis-imidazolium salts according to the invention are suitable for the treatment of textiles which consist of or contain cellulose.

As cellulose fiber material comes from regenerated or in particular natural cellulose, such as. B. celling wool, viscose silk, hemp, linen, jute or preferably cotton, and fiber mixtures z. B. those made of polyamide / cotton or in particular polyester / cotton, where the polyester content can be pre-dyed or post-dyed. Cellulose acetate can also be used.

The textile material can be in any form, such as. B. as yarn, skein, woven fabric, knitted fabric, felt, preferably in the form of textile fabrics such as woven or knitted fabric, which consist entirely or partially of native, regenerated or modified cellulose.

Using the bis-imidazolium salts according to the invention, uniform and vivid colorations are obtained which are distinguished by an improved color yield compared to known processes. In particular, dyeings and prints on cellulose fiber material with reactive as well as with substantive dyes are produced, which show a considerable improvement in wet fastness properties. In addition, the decrease in tearing strength of the dyeings is not impaired by the use of the bisimidazolium salts according to the definition.

In the following examples, the percentages relate to the weight, unless stated otherwise. The amounts relate to commercially available, ie. coupé goods and with the aids on pure substance. The five-digit Color Index numbers (C.I.) refer to the 3rd edition of the Color Index.

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

672 220 G.

Production Examples Example 1

225 g of a bis-imidazole compound (50% in water) of the formula r ~ i

Y

- ^ - gr8 *

(i)

10th

are mixed with 12.7 g sulfuric acid (96%) and 33.5 g water. 46.25 g of epichlorohydrin are then added dropwise to this solution at 60 ° C., the temperature rising to 68 ° C. The reaction mixture is then stirred at 70-75 ° C. for 10 hours.

After this reaction time, the amine number and epoxy number are: 0.

Now the solution obtained is evaporated to dryness. 170 g of a bis-imidazolium salt of the formula are obtained

(11)

ch -çh-ch -cl

"2X" ~ "2

fr— »

X

ch3- (

: H2-CH-cH2 - (. V ch2-jh-ch2 "c1

ff — Û

f °,

Ï-CH „-ÇH-CH

©. ©

so

O0

The bis-imidazole compound of the formula I used is prepared as follows:

34 g imidazole are dissolved in 112.5 g water. The solution is heated to 45 ° C., after which 78.5 g of a bisepoxide of the following formula are added dropwise over the course of 75 minutes: ru

-ch2-QH

CH,

The temperature rises to 61CC.

30 After a reaction time of 70 minutes at 60 C, the epoxy content is: 0.

225 g of a clear 50% solution of the bis-imidazole compound of the formula (I) are obtained.

35 Examples of use

example 1

500 g of cotton yarn are wetted in 5 liters of water in a bobbin dyeing machine, and the liquor is heated to 95 to 98 ° C. Then 20 g of a color

40 substance of the formula

(21).

so h I

• •

I Ii

• 4 • *

^ / \ f • •

I.

so3h

Cl I

X

A '

y — N = N— •

ho nh— •,

I I V

• •

II I

ho; js / ^ xs03h

—Nh I

✓ \

I II% / '

I.

—Nh

60

and 400 g of sodium sulfate were added. The mixture is cooled to 80 ° C. and 10 ml of an aqueous 30% sodium hydroxide solution and 25 g of sodium carbonate are added. The mixture is cooled further to 40 ° C. and 60 ml of the 30% sodium hydroxide solution and 50 g of the bis-imidazolium sulfate prepared according to Example 1 are added. The textile is then treated for 60 minutes at 40 CC and then rinsed and dried.

A uniform and bright red color is obtained with an increased color yield and excellent wet fastness properties. The ISO-C2S wash is significantly improved.

Example 2

100 g of cotton fabric are wetted with 800 g of water in a short fleet jet. The bath is then heated to 40 ° C. and with 3 g of a direct dye of the formula

672 220 G.

nh- 'I

for \

\ / • = •

/ 0ch3

(22)

4 \

oh n = n— ^ ^ nh — v? —nh-

1 w

• • •

I II I

rfL

/ \ / S03H • • •

I II!

vv \

och

h03s / ns03h oh

/ ~ \

\ / • SS •

and 48 g of sodium sulfate were added. After 10 minutes, 15 are rinsed and dried.

at the same temperature 9.6 g of an aqueous 30% sodium. A uniform and strong red color is obtained.

hydroxide solution and 8 g of the exercise prepared according to Example 1 with a 50% increase in yield. The ISO-C2S bis-imidazolium sulfates were added. The fabric is then laundry showing grade 4.

treated for another 60 minutes at 40 CC and then

20th

Example 3

A cotton fabric is placed on a foulard with a liquor containing 60 g of the dye of the formula

(23)

/

so3h

/

<> -N = N— (>

Çu- ° x

I • •

I S V S>

-N = N-

s \ s \ • •

i i ii

Cl I

KT

H03 /

c6 "

HO / 'W V'_NH2

3 ch3

100 g of urea. A color-rich and uniformly blue color is obtained.

35 g of the bis-imidazolium solution prepared according to Example 1, which improves the color yield by 20%.

fates points. After storage in a steam-sown

40 g of sodium hydroxide solution (30%) and saturated atmosphere for 3 days at 60 ° C caused the

3 g of sodium salt of 3-nitrobenzenesulfonic acid staining does not stain the accompanying tissue (contains hydrolysis test, impregnated. The liquor absorption is 80%. Before the ISO-C2S wash). The ISO-C2S wash is too

The tissue is then rolled up and 18 hours at 40 after the hydrolysis test 4.

Stored at room temperature. The fabric is then washed hot and cold and dried.

Example 4

A cotton tricot comes with a liquor containing 12 g of the dye of the formula per liter

(24)

.OH

\ / • 3 •

»2

nhch

Oh oh

I I

^ —H = 1, - / V \ _

IUI I II I

/ \ s \ S \

so h ■

nh so3H

Oh

\

y

"\

f2

no.

100 g urea

35 g sodium hydroxide solution (30%)

Contains 26 g of the bis-imidazolium sulfate prepared according to Example 1, padded. The goods are then rolled up, packed airtight and stored at room temperature for 20 hours. The textile is then rinsed and dried. A strong purple color is obtained. The yield increase is 100%. In addition, the wet fastness of the dyeing is excellent. The accompanying fabric is practically not stained in the ISO-C2S laundry test and when testing the wetness-60 fastness.

Example 5

A dyeing which has been produced on cotton tricot with 6% of the dye 65 of the formula (21) is carried out using a liquor which is in liters

26 g of the bis-imidazolium sulfate prepared according to Example 1 and

672 220 G.

32 ml sodium hydroxide solution (30%)

contains, padded. The fleet intake is 85%.

The goods are then dried at 90 ° C and then treated at 140 ° C for 3 minutes. The goods are then rinsed and dried.

After a hydrolysis test, the goods show grade 4 in the ISO-C2S wash.

Example 6

One in a conventional manner with 5% of a dye s of the formula ho s - * 1

0-I

Cu

(25)

^ \ ^ • • •

t II I

% / \ / \

-0 I

0-I

cu-

n = n-

\

so3H

/

15

S "\

m

\

-0 I

nhcooch. I "

n = n— |

• •

II I

/ W

the finished dyeing is aftertreated as described in Example 5. The tests for the ISO-CS2 wash and the fastness to wet ironing (in contrast to a conventionally post-fixed dye) show no bleeding on the accompanying fabric.

Example 7

Before dyeing, a cotton fabric is padded with a liquor, which is in liters

26 g of the bis-imidazolium sulfate prepared according to Example 1

32 ml sodium hydroxide solution (30%)

contains. The goods are then dried at 90 ° C. and thermosoled at 140 ° C. for 20 minutes.

1 kg of the pretreated fabric is wetted in 30 liters of water at 25 ° C, followed by 30 g of a dye of the formula

(26)

ch30 "(

/ /

S03H

-N = N— *

Oh

• •

II t

Cl I

\

A

/ V V

• —nh— \ nn_.

v

/ \

/ s03h /

so3H

600 g of sodium carbonate and 90 ml of sodium hydroxide solution (30%) are added.

The dyeing liquor is heated to 80 ° C. in the course of 40 minutes and kept at this temperature for 60 minutes. The dyed fabric is then rinsed hot and cold and dried.

Pretreatment of the goods with the imide azolium salt improves the dye yield by 60%. The coloring also shows excellent wet fastness properties.

Example 8

35 Bleached cotton terry is made on a Rouleaux printing machine with 1 kg of a printing paste of the composition

400 g 5% alginate thickener,

40 100 g urea

50 g of a dye of the formula

-Cu-

NH "

(27)

h03s "î

Cl \

S ~ \ / \

<

«

/ Cl

^ \

II

\ / '•

I.

—Nh

Cl

-N = N-

'• •

i ii% / \ ^

• •

I.

rS03H

so3h

10 g m-nitrobenzenesulfonic acid (sodium salt) 60 g sodium carbonate solution 30% and 380 g water printed in such a way that 3 cm printed strips result in addition to 3 cm unprinted strips. The goods are then dried, steamed at 101 ° C. for 8 minutes, rinsed, soaped at the boil and dried. Then the printed goods with a fleet, which is in liters

23 g of the bis-imidazolium sulfate prepared according to Example 1 and

30 ml sodium hydroxide solution (30%)

contains, padded. The fleet intake is 85%. The goods are then dried at 80 ° C and treated at 140 ° C for 3 minutes. The goods are then rinsed and dried. The wet fastness properties, in particular the ISO-C2S wash and the wet iron fastness fastness of the color printing, are significantly improved by this aftertreatment with the imidazolium salt even after a hydrolysis test.

s

Claims (9)

3rd 672 220 G. PATENT CLAIMS 1. Bis-imidazolium salts of the formula (1) i R. I. R " 2 © 2Y n0 n where Q is a divalent aliphatic hydrocarbon radical with 4 to 12 carbon atoms interrupted in the chain by a hydantoin group and optionally substituted by hydroxyl groups, Xi and X2, independently of one another, the group - <* 2- ^ 2 or -CH -CH-CH -Hai 2 | 2nd OH Shark a halogen atom, Ri and R;, independently of one another, hydrogen. Phe-nyl or an aliphatic radical. n 1 or 2 and Ye is an anion of an inorganic or organic acid and the imidazole rings A and B, independently of one another, are unsubstituted in the 4- and / or 5-positions or substituted by unsubstituted or substituted by halogen, hydroxyl or cyano. 2. Bis-imidazolium salts according to claim 1, characterized in that in formula (1) Q is an alkylene radical in the chain which is interrupted in the chain by a hydantoin group which is bonded to the N atoms and is optionally substituted in the a-position by methyl and is optionally substituted by hydroxyl groups with 6 to 10 carbon atoms. 3. bis-imidazolium salts according to any one of claims 1 20 and 2, characterized in that they have the formula 10th 15 (2) I D I CH2 A / * " * 3 ÔH-0H <k2-shark T2 CH-OH CH2-Hal1 , © 2Y n0 correspond in which n and Y® have the meaning given in claim 1, Hali bromine or chlorine, Qi is an alkylene radical having 6 to 10 carbon atoms in the chain which is bonded to the N atoms and optionally substituted in the a position by methyl and optionally substituted by hydroxyl groups, and R3 is hydrogen, phenyl or alkyl having 1 to 17 carbon atoms and ring D is unsubstituted or substituted by methyl or ethyl. 4. A method for improving the color yield and wet fastness of dyeings or prints produced with anionic dyes on cellulose fiber material, characterized in that the fiber material is treated with a bis-imidazolium salt according to claim 1 before, during or after dyeing or printing. 5. The method according to claim 4, characterized in that the treatment of the cellulose fiber material with the bis-imidazolium salt is carried out continuously according to a foaming process. 6. The method according to claim 5, characterized in that the continuous treatment takes place after or in particular during dyeing. 35 7. The method according to claim 6, characterized in that the continuous treatment is carried out according to the block-cold dwell method. 8. The method according to any one of claims 4 to 7, characterized in that the fiber material is simultaneously 40 days treated and dyed according to the block-cold-dwell-method. 9. The method according to claim 5, characterized in that the treatment of the cellulose fiber material with the bis-imidazolium salt according to the exhaust process 45 follows.