Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
  • D06P1/12—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ
  • D06P1/127—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ using a stabilised diazo component, e.g. diazoamino, anti-diazotate or nitrosamine R-N=N-OK, diazosulfonate, hydrazinesulfonate, R-N=N-N-CN

Definitions

• the present invention provides a process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers.
• water-insoluble azo dyestuffs can be produced on textile material of cellulose or protein fibers by treating the textile material in an alkaline bath which contains a coupling component and a diazoamino compound of the Formula 1 Alk in which R represents phenyl, halogenophenyl, alkylphenyl, alkoxyphenyl, dialkylphenyl, alkylhalogenophenyl, alkoxyhalogenophenyl, alkylcarbamylphenyl, alkoxycarbamylphenyl, alkylsulfamylphenyl, alkoxsulfamylphenyl, alkyl(alkylor aralkyl-sulfonyl) phenyl, alkoxy (alkylor aralkyl-sulfonyl) phenyl or acylaminophenyl, Alk represents lower straight or branched chain alkyl which may be substituted by carboxyl, and R represents carb
• the process of the present invention is carried out by treating the textile material in the form of yarn hanks, wound bodies, slubbings or piece goods in an alkaline bath which contains a coupling component having high substantivity and a diazo-amino compound of the indicated composition as Well as a wetting or dispersing 3,484,181 Patented Dec. 16, 1969 agent and, if desired, a mineral salt, for example, sodium chloride, sodium phosphate or sodium sulfate.
• the treatment is carried out for at least 10 minutes in order to ensure that the coupling component is sufficiently and uniformly fixed onto the textile material.
• the process is carried out at temperatures between about 10 and about 35 C., suitably at room temperature or at a slightly elevated temperature.
• an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycollic acid, a mixture of these acids, a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid, with an organic acid or a mixture of a mineral acid with the salt of an organic acid, is added to the bath in a quantity such that the total quantity of alkali in the bath and on the textile material is neutralized and a pH-value of between about 4 and 7 is reached.
• an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycollic acid, a mixture of these acids, a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid, with an organic acid or a mixture of a mineral acid with the salt of an organic acid
• the pH-value required for obtaining optimum dyestuff yield depends, above all, on the diazoamino compound of the Formula 1 used.
• the pH-value is at about 5, in the case of compounds in which R is alkoxycarbamylphenyl it is at about 5, in the case of compounds in which R is alkoxysulfamylphenyl at about 4 and in the case of compounds in which R is acylaminophenyl it is at about 6.
• the temperature required for the dyestuff formation is in the range of between about 10 and about 40 C.
• the material is subsequently washed in a neutral or acid bath, if desired or required in the presence of dispersing agents, and the dyeing is further treated in the usual manner. In this manner, dyeings are obtained which exhibit very good fastness to rubbing.
• Piece goods can be dyed in the following manner: the goods are impregnated on a two or multiple roller foulard with a mixture of the coupling component and an excess of diazoamino compound, the goods are wound up and after a period of stay of, for example, half an hour, coupling is effected at temperatures below 40 C. by passing the goods through an organic acid, a mixture of organic acids or a mixture of organic and mineral acids.
• This dyestuff development may be effected by a single passage in a compartment of a roller vat or by several passages in a jigger or winch beck; the addition of mineral salts and dispersing agents during impregnation and development may sometimes have a very advantageous effect.
• the concentration of the coupling component in the initial bath must be lower in comparison to that of the second bath, corresponding to the higher afiinity of the coupling component, whereas the concentration of the diazoamino compound in the initial bath compared to that of the second bath is not to be reduced.
• This method of operation saves energy; intermediate drying of the dyestufi prior to the development of the dyestuff is not required.
• coupling components there may be used in the process of the present invention compounds which are distinguished by a high substantivity towards the textile material used, i.e. coupling components, which at a goods to liquor ratio of 1:20, a dyeing period of 30 minutes, at 30 C., a concentration of 1 g. per liter of water, without addition of salt and with an excess of 4.5 g. of sodium hydroxide per liter of bath, have so high a substantivity that at least 9 g. are absorbed on 1 kg. of cotton.
• coupling components which at a goods to liquor ratio of 1:20, a dyeing period of 30 minutes, at 30 C., a concentration of 1 g. per liter of water, without addition of salt and with an excess of 4.5 g. of sodium hydroxide per liter of bath, have so high a substantivity that at least 9 g. are absorbed on 1 kg. of cotton.
• Suitable compounds are, for example, 2,3-hydroxynaphthoyl-aminobenzenes such as 1-(2,3'- hydroxynaphthoylamino) 2,5 dimethoxy-4-chlorobenzene or 1-(2',3'-hydroxynaphthoylamino)-2-methoxy-4- chloro-S-methylbenzene, 6-bromoor 6-methoxy-2,3-hydroxynaphthoic acid aryl amides such as 1-(6'-bromo- 2',3 hydroxynaphthoylamino)-2-methoxybenzene, condensation products of 2,3-hydroxynaphthoic acid and oligonuclear isocyclic or heterocyclic amines such as 2- (2,3' hydroxynaphthoylamino)-naphthalene, 2-(2,3'- hydroxynaphthoylamino) carbazole, 2 (2'3-hydroxyn
• wetting or dispersing agents there may be used the compounds conventionally used in ice colour technique, for example, condensation products of higher molecular fatty acids and protein degradation products, condensation products of higher molecular fatty acids and aminoalkysulfonic acids, condensation products of formaldehyde with naphthalene-sulfonic acids, or purified sulfite cellulose waste liquor.
• the process can be applied to textile material of natural or regenerated cellulose, cyanoethylated cellulose, wool, natural silk or regenerated protein fibers.
• the process of the present invention is considarably simpler.
• the dyebath is usually drained after the impregnation with the coupling component, the goods are centrifuged, separated with suction or rinsed intermediately and the dyestufr is developed with a diazonium compound in a second bath.
• impregnation and development are carried out 31 one bath and after the period of stay required for fixing the coupling component, coupling is effected without any other intercalated operation, which saves operational time to a considerable degree.
• diazoamino compounds of diazotized aromatic amines and N-(methyl)-aminoacetic acid, iminodiacetic acid, N-methyltaurine or N-alkyl-sulfanilic acids may be used for the production of azo dyestuffs on the fiber, by printing such diazoamino componds in admixture with coupling components on the material and developing the dyestuffs by a treatment with acids.
• This process is at present widely used in industry.
• water-insoluble azo dyestuffs can be produced on vegetable fibers by treating these fibers at long goods to liquor ratios with a bath containing a coupling component and a diazo or tetrazoamino compound without hydrosolubilizing groups and subsequently developing the azo dyestuif by treatment with an acid bath (German Patent 1,057,061).
• the process of the present invention which is carried out with substantive coupling components and diazoamino compounds of the indicated Formula 1 is distinguished by the fact that the development of the dyestuffs can be effected at low temperatures and that it is not necessary to raise the temperature after the addition of acid.
• Another advantage of the process of the present invention is that the diazoamino compound with aliphatic aminocarboxylic acids as stabilizers are present in the bath in the form of dissolved alkali metal salts, which ensures complete penetration of the material to be dyed and thus complete coupling, whereas, if water-insoluble diazoamino compounds are used, these compounds are only deposited on the surface of the material to be dyed which turns out in unsatisfactory dyeings and fastness to rubbing.
• EXAMPLE 1 A cross-wound bobbin of 500 g. of cotton was treated for 30 minutes at 30 C. on a dyeing apparatus in the following bath:
• EXAMPLE 5 g. of sodium chloride and 2.35 g. of the diazoamino Cotton on cross-wound bobbins was treated, at a goods compound of the formula to liquor ratio of 1:10, for half an hour, at 2530 C., in a bath containing, per liter of liquor, 1 g. of the sodi- (IJHS um salt of ethylenendiarninotetracetic acid, 1 g. of a condensation product of oleic acid and methyltaurine, 6.4 O 2 Nab cc. of a sodium hydroxide solution of 38 B., 1.1 g. of A) 2-(2,3'-hydroxynaphthoylamino) naphthalene, 30 g.
• EXAMPLE 10 1TRl 2 Cotton yarn was treated, at a goods to liquor ratio of 5 1:20, for 15 minutes at 30 C., in the following bath: 1 in Which R is a member Selected from the group Consistg. of 2- (2',3'-hydroxynaphthoylamino) -3 -methoxy-dig f p y ehlerophenyl, lower y p y lower phenylene oxide was dissolved in 2 cc. of denatured ethyl alkOXY P 31 (ii-lower y p y lower alkylchloroalcohol, 0.5 cc.
• R is a member Selected from the group Consistg. of 2- (2',3'-hydroxynaphthoylamino) -3 -methoxy-dig f p y ehlerophenyl, lower y p y lower phenylene oxide was dissolved in 2 cc. of denatured
• a 16.4% diazoagent selected from the group consisting of organic acids, amino compound of diazotized l-amino 2 -methy1-5- inorganic acids and mixtures thereof in such an amount chlorobenzene and the sodium salt of N-ethyl-sulfanilic that in the bath and on the textile material a pH value acid, or 4.75 g. of a 16.3% diazoamino compound of dietween about 4 and 7 is achieved.
• sodium phosphate and sodium sulfate is employed.
• a process for producing water-insoluble azo dyestuffs on cellulose and protein textile materials which comprises treating said textile materials at temperatures 1,382,560 10/1932 Glietellburg et between about 10 C. and about 35 C. in an aqueous 3; 3 1 13 0 am ers alkaline bath WhlCh contains (1) a couplln component 2,926,986 3/1960 Petitcolas et a 8 45 which is highly substantive for the textile material employed, said component being selected from the group GEORGE LESMES, Primary Examiner consisting of arylamides of aromatic oitho-hydroxy car- T. J. HERBERT, JR., Assistant Examiner boxylic acids, arylarnides of heterocyclic ortho-hydroxy US. Cl. X.R. carboxylic acids, arylarnides of acyl acetic acids and aryl-

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• 1964
  • 1964-02-22 DE DEP1267A patent/DE1267661B/de active Pending
  • 1964-03-07 DE DEP1267A patent/DE1267662B/de active Pending
  • 1964-07-08 DE DE1964F0043370 patent/DE1281393C2/de not_active Expired
  • 1964-07-25 DE DEF43563A patent/DE1296124B/de active Pending
• 1965
  • 1965-02-17 NO NO156819A patent/NO119986B/no unknown
  • 1965-02-18 US US433783A patent/US3484181A/en not_active Expired - Lifetime
  • 1965-02-19 ES ES0309570A patent/ES309570A1/es not_active Expired
  • 1965-02-19 DK DK89265AA patent/DK121293B/da unknown
  • 1965-02-19 AT AT148365A patent/AT266028B/de active
  • 1965-02-19 CH CH229365A patent/CH461669A/de unknown
  • 1965-02-22 FR FR6465A patent/FR1435030A/fr not_active Expired
  • 1965-02-22 GB GB7627/65A patent/GB1090795A/en not_active Expired
  • 1965-02-22 JP JP40009783A patent/JPS4942861B1/ja active Pending
  • 1965-02-22 NL NL6502187A patent/NL6502187A/xx unknown
  • 1965-02-22 BE BE660080D patent/BE660080A/xx unknown

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