SU519459A1 - The method of obtaining active phthalocyanine dyes - Google Patents

Description

(54) METHOD FOR OBTAINING ACTIVE PHTHALOCYANINE DYES

This invention relates to the field of producing active phthalocyanine dyes suitable for dyeing and printing cellulosic materials. A known method for producing active phthalodianine dyes involves the alkylation of an alkyl sulfamide copper phthalocyanine derivative copper phthalocyanine chloroethyl sulfate and the formula Cifc CSO-iNHCHaCH2Ce) ni, where Cfcc is the phthalocyanine copper, t3, substituted alkylaminoamylamines, and the tsimid alkoxylaminthylamino, you can also get to the way in the case of displaced alkylamine, you will be covered with the alfacial alkylate of this reaction product, the separation of the desired product and its displacement with a stabilizer, for example, with potassium biphthalate, known methods. The duration of the process is-g; 6 o'clock Obtained by a known method, the dyes correspond to the structural formula / (802-W-CH-rCHji-N-CHO-eH gOSOjA) CTC - (S02-NH-CHo-CH2-OH) n where Cifd - has the above value, TJ - hydrogen, alkyl, sulfoxyalkyl, A - hydrogen, potassium, sodium, m 2-3 -, n 1-2, rn + ni, Dignity phthalocyanine dyes, obtained by a known method. 5 holds a high degree of fixation and storage stability. Dyes dye cellulosic materials in turquoise color with good color characteristics. The disadvantages of this method are the complexity and duration of the process, due to the use of organic solvent, the need for its distillation and regeneration. In order to eliminate the above disadvantages, it is proposed as an alkyl sulfamide

a copper phthalocyanine derivative use a compound of the general formula.

/ (802-Ж-Е-№1-Вг OHlm SiТц- (80zA) l

(SO.)

B, R

where CUFc is copper phthalocyanine, T alkilec,

 hydrogen, alkyl, oxyalkyl, A - hydrogen, potassium, sodium,

t,

P 0-2) p 0-2; m -t-n-t-p 64

as a substituted alkyl-haloalkyl, and the alkylation is carried out in an aqueous alkaline medium.

The proposed method makes it possible to simplify the technological process and its instrumentation by eliminating organic solvent from the process and intensify the ft technology by a factor of 4.

The advantages of the proposed method include the versatility of the available feedstock, which makes it possible to obtain not only the known active phthalocyanine dyes, but also a number of new ones, which do not fail to be known in terms of their quality and color characteristics.

The dyes obtained by the proposed method have a high degree of fixation and dye the cellulosic materials in pure-burj color with good strength to wet treatments and light.

Example. 11.5 g Ciphs- 2- (2-hydroxyethyl) -

α-aminoethyl sulfamide β-sulfonic acid is dissolved in 180 ml of 1% sodium hydroxide solution, heated to 94 ° C and 4 g of ethylene chlorohydrin are added. Stir at 94-96 for 1 hour, filter out CIP-2-2,2- (dioxyethyl) -aminoethylsulfonamide sulfonic acid, filter, re-precipitate from dilute acetic acid and dry at 80-90 ° C. Esterify with sulfuric acid monohydrate at 10- 20 ° С, formed of CIP-2- (2,2-disulfoxyethyl) -aminoethylsulfamide-sulfonic acid, pouring onto a mixture of ice-water and potassium chloride, and filtered at 0-5 C. The paste is suspended in water, neutralized to pH 3 , 5 by adding a K CO solution, they are salted out with potassium chloride, filtered at 3-5 ° C; Shift from 2.2 g of potassium acid phthalate in 27 ml of water and dry under vacuum.

The weight of the finished dye 15-15,5 g

Dyes cotton fabric in turquoise color.

PRI mme R 2. 12 g of CIP-2 (2-oxyciprepyl) -amino ethylsulfonamyl sulfonic acid in 120 ml of a 1.5% aqueous solution of sodium hydroxide is stirred with 8 ethylene chlorohydrin for 30-40 minutes at 96-97 Sediment Ciphs-2 (2-hydroxypropyl) -oxyethyl) -aminoethyl. Pfamide-sulfonic acid is filtered, purified by reprecipitation with dilute acetic acid, cjouax at 90-95 C and esterified with sulfuric acid monohydrate at 10-12 C. -sulfoxypro5 bc-sulfoxyethyl) -aminoethylsulfonamide-sulfonic acid under conditions similar to example 1. The weight of the finished dye is 15.5 g.

Dyes cotton fabrics in turquoise color with a greenish tint. 10 frost. 12.4g SiFz-2- (2-hydroxyethi-1) -aminoethylsulfonamide in 190 ml of 1% alkaline solution is stirred with 8 g of ethylene hydrochloride at 94-96 ° C for 1 hour. Filter, purify the CPS-2- (2,2-dioxyethyl) -aminoethylsulfonamide by reprecipitation from dilute acetic acid, and dry at 85-90 ° C. Esterify and esterify the product under conditions similar to Example 1.

The weight of the finished dye 16-16,5 g

Dye dyes cotton fabric

20 turquoise color.

Example 4. 11.5 g of CIP-2- (2-hydroxyethyl) -aminoethyl sulfamide sulfonic acid are dissolved in 180 ml of 1% NaOH solution, heated to 95-98 ° C and stirred at this temperature with 12.7 g of benzyl chloride within 1 hour The filter is dried, the obtained CIP2 - 2- (2,2-hydroxyethylbenzyl) -aminoethylsulfonamide-sulfonic acid is dried at 90-95 ° C and esterified in pyridine with anhydrous-N-sulfonic acid pyridinium at 80 ° C for 10 hours.

30 Pyridine was separated, the precipitate Ciphz-2- (2,2sulfoxyethylbenzyl) -aminoethylsulfamide -sulfonic acid was taken up in ice water and dried. The weight of the finished dye about 13g.

35 Dye paints cotton fabric in a greenish-blue color.

Example 5.11.5g SIFTs- 2- (2-hydroxyethyl) aminoethylsulfonamylsulfonic acid in 120ml of 1.5% aqueous NaOH solution is heated to 95-96 ° C and stirred

40 at this temperature with 16.5 g of methyl hexyl

(normal). Filtered, the obtained CIP-2- (2,2-hydroxyethylhexyl) -aminoethylsulfamide sulfonic acid is dried at 80-90 ° C, dissolved in pyridine, and esterified with pyridium 45-anhydro-N-sulfonic acid at 80 ° C for 10 hours. The conditions of Example 4 are as follows. The weight of the finished dye is about 12 g.

Dye paints cotton fabric in turquoise.

Example 6. 12 g of CIP-2- (2-hydroxyethyl) 50 aminoethylsulfonamide (2-hydroxyethylsulfamide) is dissolved in 190 ml of sodium hydroxide solution, heated to 95-97 ° C, 8 g of Eshlenhlorgndrin are added and stirred at this temperature for 1 hour.

55 The obtained CIP-2- (2,2-dioxy-E1) -aminoethyl sulfamide - (2-hydroxy-1-I sulfamide) is filtered, purified, and esterified under the conditions of Example 1. The weight of the dye is 16-17 g.

Claims (1)

Dye paints cotton 6C fabric in turquoise. Example. 13 g of CIP-2- (2-oxylpropyl) -amine ethylsulfamvda in 190 ml of 1% aqueous solution of caustic soda are heated for 2 hours with 8 g of ethylene chlorohydri at 60-70 0. Half a CiFc (2,2-hydroxypropyloxyethyl) - amino ethyl sulfamide is filtered off, purified by reprecipitation from a dilute sodium hydroxide solution, and dried at 70-80 ° C. The dye is esterified and made under the conditions of Example 1. The dye weight is about 17 g. The dye colors the cotton fabric in a turquoise color with a greenish tinge. The method of obtaining phthalocyanine dye actives by alkylation of an alkyl sulfamide derivative of copper phthalocyanine with substituted alkyl followed by esterification of the reaction product thus obtained, separating the reaction product and mixing it with a stabilizer, for example, potassium bphthalate, using known techniques, in order to simplify and intervene. of the technological process, as an alkyl sulfamide derivative of copper phthalocyanine, a compound of the general formula (( 5o.-mn-th-cn -t -it} t "SFC-SZOZA) (SO., N: i) where SFC is the copper phthalocyanine; R and R-alkylene B1I Rs- hydrogen, alkyl, oxyalkyl; And - hydrogen, potassium, sodium, t -2-4 p 0-2, R 0-2; m + n + p 4, as substituted alkyl-haloalkyl, and alkylation is carried out in an aqueous alkaline medium. Priority of 04/10/74