CS267441B1 - Imidazolium salt derivative and process for its preparation - Google Patents

Abstract

The active ingredient of the preparation for intensifying the leaching of hydrolyzed reactive dye is a compound of the general formula I, where Y is a group of formula II X is an anionic residue k is an integer 1,2 or 3 A is a group of formula III, IV or V B is a hydrogen atom or has the meaning Y - A The preparations according to the invention significantly shorten the finishing operations after dyeing or printing of cellulose materials with reactive dyes. They are produced by the action of hydrazine on aqueous solutions of 1,3-bis (3-chloro-2-hydroxypropyl) imidazolinium or 1,3-bis (2,3-epoxypropyl) imidazolinium salts.

Description

The present invention relates to an imidazolium salt derivative which is useful as a composition for intensifying the process of washing textiles after dyeing or printing with reactive dyes.

The intensification of washing of reactive dyes and prints is monitored not only in terms of new structural elements of technological equipment, but also in the use of auxiliary products that accelerate washing. One such solution is the compounds protected by AO 245 170, characterized in general by structural units

- CH ₂ - CH

OH k

--- x ^r ~ ^Γ |

CI12 - M ^{+ to} - CH2 - CH - _CH2 - N

OH where r is an integer 1, 2 or 3 k is an integer 1 or 2 n is an integer 2 to 10 x is an anionic residue of a strong inorganic

CCH2) n

or the organic acid s is an integer of 1, 2, 3 or 4

M is a heterocyclic radical

R is hydrogen or alkyl of carbon

(2)

In practice, compounds containing basic structural units are produced and used on this basis

---- SOa ² “______ 2 r ~ [

-CH 2 -C 1 H-CH 2 -N 2 N-CH 2 -CH-CH 2 -NH-CH 2 -CH ₂ -CH 2 NH-CH 2 -CH 2 -CH 2 -NH OH OH (3) or

OS 267441 Bl

---- S0 ₄ ² - 2

-CH ₂ -CH-CH 2 -CH-CH 2 -NH-CH 2 -CHa NH-CH 2 -CHa -CHa -NHOH OH ¢ 4)

However, both of these compounds have certain disadvantages. The first of these has a significant chelating effect, manifested unfavorably by changing the hue and color properties of those dyes which contain a complexed metal atom. The second is not sufficiently thermally stable and may cause the release of unpleasant mouse odors from the fabrics treated with it.

These undesirable properties of this type of preparation are due to the amine part of the molecule and thus depend on the choice of the multifunctional amine for the reaction with the N, N-bispropylene chlorohydrin or N, N-bisglycidyl derivative of diazole or diazine.

AO 245 170 protects the use of diamines and multiple amines with 2 to 6 carbon atoms.

The disadvantages of compounds with 2 and 3 carbon atoms have already been mentioned. Other amines are difficult to obtain.

Therefore, other possibilities for the development of compounds were investigated, in which all the mentioned drawbacks would be eliminated.

The solution has been found to be compounds of the general formula

BB AYNNYA (5) where Y is the group _Ί - χχ) k

-CH ₂ -CH-CH 2 -N _<; ^ zN-CH ₂ OH

X is an anionic residue k is an integer 1, 2 or 3

A is --CH - CH ₂ - CL or

OH

CS 267441 Bl

- CH - CHa

OH

- CH - CHa

OH or

B is a hydrogen atom or has the meaning Y - A in the controllable reaction of hydrazine and compounds of the general formula

Z - CHz

- ch ₂ - z (6) where X and k are as defined above

Z is a group

or

- CH - CHa

OH

In the reaction, the ratio of the components must be chosen so that 2 to 4 moles of the compound of the general formula (6) per 1 mole of hydrazine. The reaction of hydrazine with the glycidyl type of the compound of general formula (6) proceeds spontaneously, the reaction with the propylene chlorohydrin derivative must be catalyzed by OH ions.

The compounds of the invention are novel compounds. They can be isolated from the reaction mixture and their constitution verified. The expected structure of the compounds listed in Table 1 was confirmed by infrared spectroscopy and nuclear magnetic resonance. However, for practical use, it is unnecessary to isolate the compounds of the invention from the reaction mixture. The reaction mixture itself can serve as a preparation for intensifying the washing of unreacted and hydrolyzed reactive dye after printing or dyeing.

Procedures for preparing the compounds of the invention and their use are described in the following examples.

Example 1:

In an enamelled duplicator equipped with a stirrer. to a submitted 350 kg of 83% aqueous solution

ES 267441 Bl

1,3-bis (3-chloro-2-hydroxypropyl) imidazolium sulfate is gradually added 35 kg of hydrazine hydrate containing 49% of hydrazine over 30 minutes of helium. 160 kg of 50% aqueous NaOH solution are slowly metered in over the next 120 minutes. The temperature is allowed to rise spontaneously to 65 ° C and is maintained at this value during the addition of NaOH.

The resulting reaction mixture contains 45% of the active substance, compound number 1 in Table 1.

Examples 2.1

In the apparatus of Example 1, 64 kg of a 25% solution of hydrazine are gradually added to 344 kg of a 70% aqueous solution of 1,3-bis (2,3-epoxypropyl) imidazolium acetate. The temperature is allowed to rise spontaneously to 65 ° C and is maintained at this value throughout the dosing period of 60 minutes. The mixture is allowed to react for a further 120 minutes. The active ingredient of the mixture corresponds to compound number 2 in Table 1.

Example 3:

175 g of 1,3-bis (3-chloro-2-hydroxypropyl) imidazolium sulfate are mixed with 16 g of a 25% aqueous hydrazine solution in a glass apparatus equipped with a stirrer, a thermometer, a reflux condenser and cooling. 40 g of a 50% aqueous NaOH solution are gradually added over a period of 60 minutes.

The reaction temperature increases spontaneously, maintaining a value of 75 to 80 ° C by cooling. After all the hydrazine has been metered in, the mixture is left to react at the same temperature for a further 90 minutes. The reaction product contains the active substance corresponding to formula 3 in Table 1.

Example 4:

In the apparatus and procedure according to Example 1, 320 kg of 50% NaOH are metered in instead of 160 kg of 50% NaOH. The reaction results in a mixture containing compound number 4 of Table 1.

Example 5 ^:

A cotton fabric printed by the machine printing technique with a printing paste of the usual composition containing a dye as a color component

Reactive blue number CI 13 50 g.kg ^-1 , after steaming with saturated steam at a temperature of 102 ° C for 10 minutes, is washed by passing through a wide-cutting machine, the 1st section of which contains cold water. 2nd to 5th compartment water temperature 90 ° C. Sections 6 and 7 contain a water bath at 90 ° C with 2 g. Γ ^{-1 of} compound number 1 from Table 1, Section 8 contains water at 60 ° C and Section 9 contains cold water.

Perfect washing of the hydrolyzed dye is achieved in one pass. When washing without an intensifying agent, the same result is achieved by at least two passes through the machine.

Claims (2)

An imidazolium salt derivative of the general formula CS 267441 Bl B B AYNNYA .1 - X ^K I ..............- k wherein Y is a group - CH2 - CH -CH2 - CH2 OH X is the anionic residue k is an integer of 1, 2 or And it's a group - CH - CH2 - CL or OH - CH - CH2 - OH or OH - CH - CH2 B is a hydrogen atom or has the meaning Y - A 2. A process for the preparation of a compound according to claim 1, characterized in that a compound of the general formula is reacted at a temperature of 20 to 100 ° C in an aqueous solution. 1 --- X * ------------ k Z - CH 2 - N - CH 2 - Z wherein X and k are as defined above Z is a group - CH - CH 2 or - CH - CH2 - Cl I OH with hydrazine in a molar ratio of 1.5 to 4: 1,