CH364573A - Process for the production of new phthalocyanine dyes - Google Patents

Description

  

  Additional patent to main patent no. 352076 Process for the production of new phthaloeyanine dyes The main patent relates to a process for the production of new, acetone-soluble phthalocyanine dyes which contain sulfonic acid amide groups whose amide nitrogen atoms each carry an alkoxyalkyl group, which process is characterized in that phthalocyanine sulfonic acid halides are used with alkoxyalkylamides implements.

   It is preferable to use alkoxyalkylamines which contain at most 5 carbon atoms and of these at most 2 in the alkoxy radical. As examples of such amines, the main patent mentions mainly ß-methoxyethylamine, ß-ethoxyethylamine, γ-methoxypropylamine and γ-ethoxypropylamine.



  It has now been found that particularly valuable dyes are obtained which are not only soluble in acetone but also in alcohol if the phthalocyanine sulfohalides indicated in the main patent are amidated with isopropoxypropylamine.



  The inventive reaction of the phthalocyanine sulfonic acid halides with isopropoxypropyl amine is preferably carried out in an aqueous medium in the presence of acid-binding agents such as alkali or alkaline earth metal hydroxides, alkali carbonates, sodium acetate or tertiary bases such as triethanolamine or pyridine.

   If necessary, an excess of the isopropoxypropylamine used for the conversion can serve as the acid-binding agent, which can be regenerated from its chlorohydrate for further reactions with phthalocyanine sulfochlorides. The reaction temperature can be varied within very wide limits; advantageously, at low temperatures, e.g. B. between 20 to 40 worked. Appropriately one uses sol che Phthalocyaninsulfochloride, the salt-forming groups, z.

   B. of sulfonic acid groups not converted into sulfochloride groups, are free and the z. B. are accessible by the method described in the main patent.



  The products obtainable by the present process are new. They are phthalocyaninesulfonic acid amides whose amide nitrogen atoms carry isopropoxypropyl groups.



  They are soluble in organic solvents such as esters and especially in alcohol and acetone. They are used for coloring natural or artificial resins, waxes, lacquers and plastic materials, e.g. B. from Celluloseäthem or esters, for example for spin dyeing of acetate silk and for dyeing natural or synthetic polymers or condensation products.



  With the dye prepared according to the invention fen can be z. B. Dye acetate silk according to the spinning dyeing method in clear, chlorine- and exhaust-gas-fast blue tones.



  In the following examples, unless otherwise stated, parts are parts by weight, percentages are percentages by weight, and the temperatures are given in degrees Celsius.



  <I> Example 1 </I> 193 parts of copper phthalocyanine are introduced into 1500 parts of chlorosulfonic acid within one hour. The mixture is heated to 70 to 75 for one hour with stirring and then increased to 130 to 135 in 11/2 hours. The mixture is stirred at this temperature for 4 hours. After cooling to 80, 600 parts of thionyl chloride are added dropwise over the course of one hour and the mixture is then stirred at 75 to 80 for a further hour. After cooling to room temperature, the mass is poured onto ice.

   The Cu phthalocyanine tetrasulfochloride is filtered off with suction and washed neutral with water. The paste obtained is stirred in 3000 parts of water and, after addition of 144 parts of isopropoxypropylamine and 100 parts of sodium bicarbonate, stirred at 35 to 40 hours for 12 hours. It is then diluted with 3000 parts of water and the acid amide obtained is filtered off.

   It is a blue, water-insoluble powder, which dissolves well in acetone and alcohol and dyes acetate silk in the mass in light- and washfast, greenish blue tones.



  <I> Example 2 </I> 89.6 parts of copper phthalocyanine-4,4 ', 4 ", 4" -tetrasulphonic acid sodium are introduced into 525 parts of chlorosulphonic acid. The mixture is stirred for one hour at 70 to 75, then the temperature is increased within 11/2 hours to 130 to 135 and then held for 4 hours at this temperature. After cooling to 70, 195 parts of thionyl chloride are added dropwise over the course of one hour and the mixture is then stirred at 80 to 85 for 4 hours.

   It is then poured onto ice and the tetrasulfonyl chloride is filtered off and washed neutral with water. The reaction with isopropoxypropylamine takes place according to the method described in Example 1. The dyestuff obtained in this way is, when dried, a blue powder which is readily soluble in alcohol and acetone and which dyes acetate silk in the bulk in lightfast and washfast, greenish blue tones.

 

Claims (1)

PATENT CLAIM Process for the production of acetone-soluble phthalocyanine dyes, characterized in that phthalocyaninesulfonic acid halides are reacted with isopropoxypropylamine. SUBSTANTIAL CLAIM Process according to patent claim, characterized in that pure copper phthalocyanine tetrasulfonic acid chloride is used.