Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B43/00—Preparation of azo dyes from other azo compounds
  • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
  • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
  • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Definitions

• the present invention relates to the manufacture of new direct dyeing azo-dyestufis, It comprises the process of making these dyestufis, the dyestufis themselves, and the material that has been dyed with the new products.
• new direct dyeing azo-dyestufis which may be characterized by dyeing properties essentially better than those of otherwise comparable dye- Y stufis, are made by introducing the thiazole ring into dyestuffs of the kind described in the said specifications, the introduction occurring either into the diazo component or into the coupling component or into both components,
• These new direct dyeing dyestuffs may be made by condensing a cyanuric halide with such components as contain at least one hydrogen atom which can react with a cyanuric halide, at least one of such compounds containing at. least one group adapted for azodyestuif formation, or a residue capable of transformation into such a group, or an azochromophor, and at least one of such compounds containing at least one thiazole ring.
• the products thus obtained may be converted into azo-dyestufi's, if necessary after transferring the aforesaid residue into a group adapted for azo-dyestuff formation, either by diazotization and coupling with a coupling component, or by coupling with any desired diam-compound.
• Such dyestuffs may also be obtained by coupling a diazobody with a coupling compound if these com-
• the new dyestuffs form powders more or less intensively colored, dissolving in water to solutions of all colors of the spectrum and ofthose which are obtained by combination of the said colors, and dyeing the textile fibre from cellulose or regenerated cellulose similar tints.
• Example 1 A fine suspension of 18.5 parts of cyanuric chloride in ice water is mixed with a neutral solution of 31.9 parts of 1: S-aminonaphthOI- 3 6-disulfonic acid and the mixture is stirred for 11 hours at 0 C. During this time there is run in gradually a solution of 5.3 parts of sodium carbonate. added a neutral solution of 32 parts of dehydrothiotoluidinesulfonic acid, the temperature is raised to 40 C. and in the course of 1% hours a solution of 5.3 parts of sodium carbonate is allowed to flow in. From the ma There is then 5 when filtered and dried it is a pale yellow powder.
• Both the secondaryand tertiary condensation products are nearly colorless in alkaline solution but on acidification become yellow. They show pronounced substantive character in that they are adsorbed by cotton without development of color in a feebly alkaline bath of Glaubers salt and can be developed, after rinsing, with various diazo-solutions to produce powerful dyeings.
• Ewample 2 18.5 parts of cyanuric chloride finely suspended in icewater are mixed with a neutral solution of 18.8 parts of l 4c-phenylenediamine-3-sulfonic acid and the mixture is stirred at O5 C. In the course of 1 hours a solution of 5.3 parts of sodium carbonate are allowed to flow in. To the slightly slimey condensation mass there is then added a neutral solution of 32 parts of dehydrothiotoluidinesulfonic acid and the whole is heated to 40 C. Within one hour a further solution of 5.3 parts of sodium carbonate is run in, the temperature is kept at 40 C. for some time and the secondary condensation product.
• This secondary condensation product may further be condensed to a tertiary product, for instance by adding to the solution described above 9.3 parts of aniline and heating for about 2 hours at (3., whereby there ,ilar to those of the above secondary product,
• the product can also be obtained by causing the components to act on the cyanuric chloride in another order, for instance the dehydrothiotoluidinesulfonic acid may be condensed in the first place.
• Isomeric products having similar properties are obtained by substituting its sulfonic acids for the aniline and monoacetyl-paraphenylenediamine or para-nitraniline for the para-phenylenediamine sulfonic acid and then saponifying or reducing the tertiary condensation product so formed.
• Example 3 parts of sodium carbonate is allowed to flow in and the temperature is then slowly raised to C. where it is kept for 2 hours. The whole is then made neutral to congo With a solution of 3 parts of sodium carbonate and a neutral solution of 32 parts of dehydrothiotoluidinesulfonic acid added. The temperature is now quickly raised to 80 C'. and in the course of it there is again allowed to flow into the mass a solution of 2.5 parts of sodium carbonate. After a further hour the formed condensation product is saponified by adding to'every 1000 parts by volume of the solution 180 parts by weight of a caustic soda solution of 30 per cent. strength and keeping the temperature at 7 580 C. for one hour.
• the solution is then neutralized with hydrochloric acid and the dyestuif is precipitated by addi tion of common salt.
• the product thus obtained is the tertiary condensation product from 1 molecule cyanuric chloride, 2 molecules of the monoazo-dyestuff from diazotized 1: 8-aminonaphthal-3 6-disulfonic acid and 1-Inethyl-3aminophenyl-l-methylether, and 1 molecule dehydrothiotoluidinesulfonic acid. It corresponds very probably with the formula OOH: OCHa l I O prtjig CHa SOaH
• Ewample 4 9.3 parts of aniline are diazotized and introduced into the solution, alkaline with sodium carbonate, of 75 parts of the secondary condensation product from 1 molecule cyanuric chloride, 1 molecule 1:8-aminonaphthol-3z6-disulfonic acid and 1 molecule dehydrothiotoluidinesulfonic acid.
• the dyestufl formed is precipitated by adding common salt, and corresponds very probably with the formula Hat l O H HOsS SO5H It dyes cotton pure rose tints.
• the same dyeing can be produced on the fibre by impregnating or dyeing the fibre with the secondary condensation product and then developing with diazobenzene.
• Example 6 N LII s Woiu y a r Hogs -s0311 g soar! and dyes cotton red-violet tints.
• a reddish-violet fast to light is obtained.
• the dyestufi may also be converted directly into a complex copper compound, for instance, by treatment with copper sulfate; the same tints on cotton are produced by this compound.
• This copper compound can also be made in the following manner :-The diazo-compound from 18.8 parts of l-oxy-Q-aminobenzene-lsulfamide is coupled with a solution of 31.9 parts of 1: 8-aminonaphthol-3 6-disulfonic acid with addition of milk of lime, the dyestuff is separated, then dissolved and converted into the complex copper salt by boiling it with a co er salt.
• the copper compound corresponding with 51.8 parts of dyestuff free from copper is dissolved, in the form of its neutral ammonium salt, in 1200 c. c. of hot water and the solution is mixed with a suspension of 18.5 parts of cyanuric chloride in water and much ice and the Whole stirred at 0 C.
• Example '7 62 parts of the secondary condensation product from 1 molecule cyanuric chloride, 1 molecule 1 4 phenylenediamine-3-sulfonic acid and 1 molecule dehydrothiotoluidinesulfonic acid described in Example 2, are diazotized at 1015 C. and coupled with a soluand dyes cotton clear greenish yellow tints.
• Example 8 Into a neutral solution of 50 parts of the secondary condensation product from 1 molecule cyanuric chloride, 1 molecule 2: 5-aminonaphthol-7-sulfonicacid and 1 moleculemono-acetyl-l -phenylenediamine, and stufi yielding somewhat yellower dyeings on parts of sodium acetate, there is caused to cotton.
• 1 molecule 2 5-aminonaphthol-7-sulfonicacid and 1 moleculemono-acetyl-l -phenylenediamine
• a diazo-compound from 32 By saponifying the dyestufl', for example, parts of the dehydrothiotoluidine-monosulby heating it with dilute caustic soda solufonic acid obtainable by baking dehydrothiotion, the acetyl group is eliminated; the dyetoluidine sulfate.
• the dyestufi? produced can be diazotized on the fibre plete the dyestufi? is salted out and isolated.. and developed by ,B-naphthol.
• naphthylamine 7 sulfonic acidazo-l-naphthylamine.
• Resorcin 1 z3-phenylenedian1ine Phenylmethyl-pyrazolone 2-naphthol-6-sulfonic acid 2-amino-8-oxynaphthalene-G-s acid (acid coupled).
• 2-amino-1z4-diarnethylbenzene further diazotized and coupled with 2-phenyl-a1nino-5-oxynaphthalene- 7-sullonic acid.
• the formula of the dyestufi (No; 23) is very probably H 7
• the formula of the dyestuif (No. 38) is very probably SOaH
• the formula of the dyestuff (N0. 52) is very SOaH *If dy'estuff No. 26, in accordance with the data of Example 3, has been made from the para-toluenesulfonic acid ester of 1:8-aminonaphtho1-8: G-disulfonic acid, the
• the formula of the dyestufi (No. 56) is very probably H30 l 1% 111' l p 00011 00011 no I!IH HO: 803E
• the formula of the dyestufi (No. 68) is very probably
• the formula of the dyestuif (No. 96) is very probably HoH-N-- N-H, OH 4.5 M
• a process for the manufacture of new direct dyeing v,azo-d'yestuffs containing at direct dyeing azo-dyestufli's containing at least one thiazole ring and at least one cyaleast one thiazole ring and at least one cyanuricring consisting in causing diazotized nuric ring, consisting in causing diazotized diazotizationcomponents of the benzene or diazotization components of the benzene or naphthalene series to react in ortho-position naphthalene series to react on coupling comto the OH-group on such coupling compoponents, these components being so selected nents of the general formula that at least one component contains at least wherein at stands for halogen or a residue one thiazole ring and at least one component. which can replace halogen, and wherein one 1 contains at least one cyanuric ring. of the ys stands for an H atom and the other 7 2.
• diazotization components ofthe benzene or nuric ring consisting in" causing diazotized naphthalene series to react on such coupling mononuclear cliazotization components of the components of the naphthaleneseries which benzene or naphthalene series to react in contain at least one thiazole ring and at least ortho-position to the OH-group on such cou one cyanuric ring. pling components of the general formula 3.
• a process for the manufacture of new direct dyeing azo-dyestufi's containing at least one thiazole ring and at least one cyanuric ring consisting in causing diazotized diazotization components of the benzene or naphthalene series containing an azo-chromophor to react in ortho-position to the OH- group on such coupling components of the general formula ll wherein m stands for halogen or a residue which can replace halogen, and wherein one of the ys stands for an H atom and the other y for an SO H group.

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Cited By (8)

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• 1928
  • 1928-07-26 DE DEG78414D patent/DE538478C/de not_active Expired
  • 1928-10-16 US US312928A patent/US1867451A/en not_active Expired - Lifetime
  • 1928-10-20 FR FR662592D patent/FR662592A/fr not_active Expired
  • 1928-10-22 GB GB30592/28A patent/GB299331A/en not_active Expired

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