DE1180082B - Process for the production of reactive dyes of the anthraquinone series - Google Patents

Description

Process for the production of reactive dyes of the anthraquinone series The present invention relates to a process for the preparation of reactive dyes the anthraquinone series, which consists in the fact that one anthraquinone derivatives, which Contain exchangeable hydrogen atoms with oc-haloacrylic acid-N-methylolamides converts and the products obtained, if they are not water-soluble, nachsulfoniert.

As anthraquinone derivatives z. B. contemplated: 1-Amino-4-arylamino-anthraquinones, such as 1-amino-4-phenylamino-anthraquinone-2-sulfonic acid, and derivatives thereof substituted in the phenylamino radical by methyl, ethyl, methoxy, ethoxy, chlorine or bromine, such as 1-amino-4 - (2 ', 4-dimethyl) -, -4- (2', 6'-dirnethyl) -, - 4 - (2 ', 4', 6'- trimethyl) - phenylamino - anthraquinone-2-sulfonic acid, 1 , 4-diarylamino-anthraquinones, such as 1,4-di- (4'-methyl-phenylamino) -anthraquinone, 1,4-di- (2 ', 4', 6 '- trimethyl - phenylamino) - anth-rachinon, 1-amino-2-aryloxy-4-arylamino-anthraquinones, such as 1-amino-2- (4'-octyl) -phenoxy-4- (2 ", 4", 6 "-trimethyl) -phenylamino-anthraquinone, where the anthraquinone nucleus can be further substituted.

The # x -haloacrylic acid-N-methylolamides are prepared according to known processes produced by reacting, x-chloro- or a-bromoacrylic acid amide with paraformaldehyde.

The reaction of the γ-haloacrylic acid Nm-ethylolamides with the anthraquinone derivatives is carried out in a sulfuric acid solution, e.g. B. in 80 to 100 iger sulfuric acid, carried out at temperatures of 0 to about 60 ° C. for several hours. If water-insoluble anthraquinone derivatives are assumed, the reaction products are in the reaction medium itself or after isolation and drying in 1000 iger Sulfuric acid or in the weak oleum post-sulfonated.

The dyes obtained dye wool, silk, synthetic polyamide fibers and leather in light-, mill-, wash-, water-, perspiration-, rubbing- and dry-cleaning-proof Tones.

You can also use them for padding and printing on natural fibers or regenerated cellulose (cotton, rayon, viscose rayon) in light, wash, Use water-, sweat- and rub-resistant shades, using the block solutions or Adding alkaline agents to printing pastes.

In comparison to known the French from the patent 1,222,194, nearest comparable dyes characterized the dyes according to the method available by the improved fixation of their dyeings on cotton from.

In the following examples the parts mean parts by weight which Percentages by weight and temperatures are given in degrees Celsius.

Example 1 In 140Teile 96% sulfuric acid are '(2 6,9Teile 1-amino-4', 4 ', 6'-trimethyl) -phenylamino-anthraquinone-sodium 2m.sulfonsaures added and dissolved at 15 to 20 under stirring. At 10 to 15 ' , 2.5 parts of oc-chloroacrylic acid-N-methylolamide are introduced and the mixture is stirred for 24 hours at 15 to 20'. It is poured onto 400 parts of ice, the dyestuff paste is filtered off and washed neutral with 100% sodium chloride solution. The dye is stirred in 200 parts of water, adjusted to pH 7.0 with 100% sodium hydroxide solution and reprecipitated with sodium chloride. It is filtered off, washed with 15 ″ sodium chloride solution and dried in vacuo.

Example 2 If the # x-chloroacrylic acid-N-methylolamide used in Example 1 is replaced by 3.2 parts of a-bromoacrylic acid-N-methylolamide, a similar dye is obtained.

EXAMPLE 3 6.3 parts of 1,4-di-p-toluidino-anthraquinone are dissolved in 145 parts of sulfuric acid (960% strength) at 15 to 20 minutes. 4.5 parts of oc-chloroacryl-N-methylolanüd are added to this solution and the mass is stirred for 24 hours at 10 to 20 minutes. The solution is then poured onto 400 parts of ice, the suspension is stirred for a short time, the precipitate obtained is filtered off, washed neutral with water and dried. By sulfonating with 20% oleum for several hours at 15 to 20 ', a dye is obtained which dyes wool green and washfast.

2 parts of the above dye, 0.8 part of an oxethylated fatty amine and 0.5 part of an oleyl polyglycol ether are dissolved in 5000 parts of water, and 2 parts of glacial acetic acid are added. This dye: liquor is heated to 40 to 50 ' , whereupon 100 parts of wool are added and the bath is brought to the boil within 30 minutes. Cook for 45 minutes, then rinse and dry the material. A level, very lightfast and wetfast green dyeing is obtained in this way. If, after the dyeing process, the dye liquor is neutralized with ammonia and the material to be dyed in it for 20 minutes at 90 ' , a dyeing that is somewhat more wet-fast is obtained. The same effect can also be achieved by treating the material to be dyed in a new bath of 5000 parts of water and 3 parts of hexamethylenetetramine at 90 to 95 minutes for 20 to 30 minutes.

Claims (2)

1. A process for the preparation of reactive dyes of the anthraquinone series, d a d u rch g e k ennzeichnet that one Anthrachinonabkömmlinge which contain exchangeable hydrogen atoms, is reacted methylolamides A-haloacrylic acid-N-with and the obtained products when they are not water soluble , post-sulfonated. 2. The method according to claim 1, characterized in that the reaction is carried out in a sulfuric acid medium. Documents considered: French patent specification No. 1 222 194. When the application was published, an explanatory coloring table was laid out.