US3502424A - Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers - Google Patents

Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers Download PDF

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US3502424A
US3502424A US442191A US44219165A US3502424A US 3502424 A US3502424 A US 3502424A US 442191 A US442191 A US 442191A US 44219165 A US44219165 A US 44219165A US 3502424 A US3502424 A US 3502424A
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acid
minutes
amino
red
bath
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Hasso Hertel
Werner Kirst
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Hoechst AG
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Hoechst AG
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    • 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

  • R represents the radical of an aromatic amine having a dissociation constant of l.l0 A represents lower molecular weight alkyl, hydroxyalkyl or carboxyalkyl
  • Y represents hydrogen, halogen, nitro, carboxylic acid, sulfonic acid, alkylsulfonyl, aralkylsnlfonyl, sulfonic acid aryl ester and sulfonic acid mono or dialkylamide wherein the alkyl groups may be substituted or closed to form a heterocyclic ring
  • Z represents a hydrogen or halogen atom, (3) a wetting or dispersing agent and, if desired, a mineral salt, and then causing formation of the dyestuff by a treatment with an acid agent at temperatures below 40 C. without intermediate drying of said textile material.
  • the present invention provides a process for the pro- COOH in which R represents the radical of an aromatic amine having a dissociation constant of l.l0-"
  • A represents a lower molecular weight straight-chain or branched alkyl, hydroxyalkyl or carboxyalkyl group
  • Y represents a hydrogen or halogen atom, a nitro, carboxylic acid, sulfonic acid, alkylsulfonyl, aralkylsulfonyl, sulfonic acid aryl ester, sulfonic acid monoor dialkylamide group, in which the alkyl groups may be substituted or closed to form a heterocyclic ring
  • Z represents a hydrogen or halogen atom, and a wetting or dispersing agent and, if desired, a mineral salt, and then causing formation of the dyestuff by a treatment with an acid agent at temperatures below 40 C.
  • the process of the present invention may be 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 diazoamino compound of the given formula as well as a wetting or dispersing agent and, if desired, an inorganic salt for example, sodium chloride, sodium phosphate or sodium sulfate.
  • the treatment may be carried out for at least 10 minutes in order to ensure that the coupling component is sufliciently and uniformly fixed on the textile material.
  • the process may be carried out at room temperature or at a slightly elevated temperature, suitably below 35 C.
  • an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycollic acid or a mixture of these acids, or 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 3 and 7 is attained.
  • the pH-value required for obtaining optimum dyestuif yield depends, above all, on which diazoamino compound of Formula 1 is used.
  • the pH-value is at about 5, for compounds in which R is sulfamylphenyl it is at about'4.5, for compounds in which R is nitromethoxyphenyl it is at about 4.5, for compounds in which R is nitromethylphenyl it is at about 3.5 and for compounds in which R is trifiuoromethylphenyl it is at about 3.
  • the temperature required for the dyestutf formation is below 40 C. After the formation of the dyestuif on the textile material has taken place, 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 finished in the usual manner. In this manner, dyeings are obtained which exhibit very good fastness to rubbing.
  • Piece goods can be dyed by impregnating them 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 say 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 dyestutf 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 with 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 with that of the second bath must not be reduced.
  • the coupling components which may be used in the process of the present invention are preferably those 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, and impregnating 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 adsorbed on 1 kg. of cotton.
  • coupling components which, at a goods to liquor ratio of 1:20, and impregnating 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 adsorbed on 1 kg. of cotton.
  • Suitable compounds are, for example, 2,3-hydroxynaphthoylaminobenzenes 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-rnethoxy-2,3-hydroxynaphthic acid aryl amides such as 1- (6 bromo 2,3'-hydroxynaphthoylamino)-2-methoxybenzene; condensation products of 2,3-hydroxynaphthoic acid and polynuclear isocyclic or heterocyclic amines such as 2 (2,3-hydroxynaphthoylamino)-naphthalene, 2-(2,3'-hydroxynaphthoylamino)-carbazole, 2-(2,3'-hy droxyna
  • benzene-dicarboxylic acids are: 1-n1ethylaminobenzene-2,4-dicarboxylic acid, l-methylaminobenze'ne 2,5 dicarboxylic acid, 1 ethylaminobenzene-2,4 dicarboxylic acid, 1 ethylaminobenzene-2,5 dicarboxylic acid, 1 propylaminobenzene-2,4- dicarboxylic acid, 1 propylaminobenzene 2,5 dicarboxylic acid, l-isopropylaminobenzene 2,4 dicarboxylic acid, 1 isopropylaminobenzene 2,5 dicarboxylic acid, 1 isobutylaminobenzene 2,4 dicarboxylic acid, l-isobutylaminobenZene-2,5 dicarboxylic acid, 1 butylaminobenzene 2,4 dicarboxylic acid, 1 butylamino
  • Suitable Z-hydroxyalkylamino-benzoic acids or 2 carboxyalkylamino-benzoic acids are for example: 2-:car boxymethylaminobenzoic acid, 2 0L carboxyethylaminobenzoic acid, 2 f3 carboxyethylamino-benzoic acid, Z-acarboxypropylamino-benzoic acid, 2-a-carboxybutylamino-benzoic acid, 2 a carboxy [3 methylpropylaminobenzoic acid, 2-carboxymethylamino 5 bromobenzoic acid, 2 carboxymethylamino 5 chlorobenzoic acid, 2 carboxy methylamino 4 chlorobenzoic acid, 2 8- carboxyethylamino 5 chlorobenzoic acid, 2 carboxymethylamino 3,5 dichlorobenzoic acid, 2 carboxymethylamino 3,5 dibromobenzoic acid, 2 B hydroxyethylaminobenzoic acid, 2 B hydroxy
  • Suitable aromatic amines are, for example: chloroanilines, dichiloroanilines, chlorotoluidines, chloroanisidines, nitroanilines, nitrotoluidines, nitroanisidines, aminobenzenesulfonic acid amides, aminophenylalkylor aralkylsulfones, trifluoromethylanilines or aminochlorodiphenyl ethers.
  • the compounds generally employed in the ice colour technique may be used, for example, condensation products of high molucular fatty acids and protein degradation products, condensation products of high molecular fatty acids and aminoalkylsulfonic 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 considerably simpler.
  • the dyebath is usually drained after impregnating with the coupling component, the goods are centrifuged, suctioned or rinsed intermediately and the dyestufi is developed with a diazonium compound in a second bath.
  • impregnating and development are carried out in one bath and after the time required for fixing the coupling component, coupling is effected without any other intercalated operation. This saves operational time to a considerable extent.
  • diazoamino compounds of the Formula 1 may be used for the production of azo dyestuffs on the fiber, by printing such diazoamino compounds in admixture with coupling components on the material and developing the dyestuff by an acid treatment. This process is at present widely used in industry. However, it has hitherto been known, and in view of the state of the art this is very surprising, that such mixtures can also be used for the dyeing of fibers at any processing stage, even for dyemg wound bodies, without intermediate drying of the goods.
  • water-insoluble azo dyestuffs can be produced on vegetable fibers by treating them at a long goods to liquor ratio in a bath containing a coupling component and a diazo or tetrazoamino compound not containing hydrosolubilizing groups and subsequently developing the azo dyestuff by treatment with an acid bath (German patent specification No. 1,057,061).
  • the process of the present invention which is carried out with substantive coupling components and diazoamino compounds of the above Formula 1 is distinguished by the fact that the development of the dyestufl can be eifected at low temperatures and that it is not necessary to raise the temperature after the addition of the acid.
  • Another advantage of the process of the present invention is that the diazoamino compound of the Formula 1 is present in the bath in the form of a dissolved alkali metal salt, which ensures complete penetration of the material to be dyed thus ensuring complete coupling, whereas, if water-insoluble diazoamino compounds are used they are only deposited on the surface of the material to be dyed which results in unsatisfactory dyeings and poor fastness to rubbing.
  • EXAMPLE 1 Cross-wound cotton bobbins were treated at a goods to liquor ratio of 1:10, at 30 C., in an aqueous solution containing, per liter, 1.8 g. of 2-(2',3-hydroxynaphthoylamino)naphthalene, dissolved in 3 cc. of denatured ethyl alcohol, 0.75 cc. of a sodium hydroxide solution of 38 B., and 3.6 cc. of hot water, and l g. of a condensation product of an aminoalkylsulfonic acid and a higher moleuclar fatty acid, 7 cc. of a sodium hydroxide solution of 38 B., 20 g.
  • EXAMPLE 2 Cross-wound cotton bobbins were treated, at a goods to liquor ratio of 1:10, at 30 C., for 30 minutes, in an aqueous solution containing, per liter, 2 g. of 2-(2',3'-hydroxynaphthoylamino) 3 methoxy diphenylene oxide, dissolved in 4 cc. of denatured ethyl alcohol, 1 cc. of sodium hydroxide solution of 38 B. and 4 cc. of Water having 60 C., and 1 g. of a condensation product of an aminoalkylsulfonic acid and a higher molecular fatty acid, 6 cc. of sodium hydroxide solution of 38 B., 10 g.
  • Diazoamino compound from 2-ethylamino-5- sulfobenzoic acid and benzene acetylamino-zmethoxy- 4 ehloro-5-methylbenzene) 1-(2hydroxycarbazole-3'- earboylamino)-4- ehlorobenzene.
  • Cotton yarn was treated, at a goods to liquor ratio of 1:20, in a 30 C. hot, aqueous solution containing, per liter, 1 g. of 2-(2,3'-hydroxynaphthoylamino)-3- methoxy-diphenylene oxide, 1 g. of a condensation product of oleic acid and methyl-taurine, 8 cc. of sodium hydroxide solution having a strength of 32.5%, 20 g. of sodium chloride, and 2.87 g. of diazoamino compound of the formula After about 45 minutes, 4.45 cc. of hydrochloric acid of 20 B. and 7.7 cc.
  • N NN s 0.-N H x 2. 25 Red brown.
  • EXAMPLE 4 and the disodium salt of 2-carboxymethylamino-3,S-dibro- Cotton yarn was treated at a goods to liquor ratio of 1:20 in an aqueous solution having 30 C. and containing, per liter, 1.5 g. of 1-(5-hydr0xy-1',2',l",2-benzocarbazole-4'-carboylamino)-4-methoxy-benzene, 0.75 cc. of formaldehyde having a strength of 33%, 1 g. of a condensation product of oleic acid and methyl-taurine, 8.5 cc. of sodium hydroxide solution of 38 B, 20 g. of sodium chloride, and 3.4 g.
  • the yarn was then rinsed and soaped for 15 minutes at 60 C. and subsequently for 15 minutes at the boiling temperature with 2 g. of a condensation product of oleic acid and methyl-taurine, 0.5 g. of the sodium salt of nitrilotriacetic acid, and 1 g. of sodium carbonate, per liter of water, rinsed and dried. A reddish brown dyeing exhibiting good fastness to rubbing was obtained.
  • EXAMPLE 6 1 kg. of cotton was treated, at C., in an aqueous solution containing, in 20 liters, 19.8 g. of 2-(2'-3'-hydroxynaphthoylamino) 3 methoXy diphenylene oxide, dissolved in 44 cc. of denatured alcohol, 11 cc. of sodium solution of 38 B. and 44 cc. of water having 60 C., and 69.5 g. of the diazoamino compound from diazotized 1-amino-2-methoXy-benzene-5-sulfonic acid diethylamide mobenzoic acid, 149 cc. of sodium hydroxide solution having 38 B., 20 g. of a condensation product of oleic acid and methyl-taurine and 400 g. of sodium chloride.
  • EXAMPLE 7 1 kg. of cotton was treated, at 25 C., in an aqueous solution containing, in 20 liters, 21 g. of 2-(2',3'-hydroxynaphthoylamino)-naphthalene, dissolved in 44 cc. of denatured alcohol, 88 cc. of a sodium hydroxide solution of 38 B., 44 cc. of water having 60 C., and 22 cc. of a formaldehyde solution having a strength of 30%, and 74 g.
  • EXAMPLE 8 1 kg. of cotton was treated, at 25 C., with an aqueous solution containing, in 20 liters, 19.8 g. of 2-(2,3'-hydroxynaphthoylamino)-3-methoxy-diphenylene oxide, dissolved in 44 cc. of denatured alcohol, 11 cc. of sodium hydroxide solution of 38 B. and 44 cc. of water having 60 C., and 56.2 g. of the diazoamino compound from diazotized l-amino-2methyl-3-chlorobenzene and the disodium salt of 2-carboxymethylamino 3,5 dibromobenzoic acid, 149 cc. of sodium hydroxide solution of 38 B., 20 g. of a condensation product of oleic acid and methyltaurine and 400 g. of sodium chloride.
  • EXAMPLE 9 1 kg. of cotton was treated, at 25 (3., in an aqueous solution containing, in 20 liters, 37 g. of 1-(2,3'-hydroxynaphthoylamino) 2 methoxy 4 chloro 5 methylbenzene, dissolved in cc. of denatured alcohol, 20 cc.
  • Diazoamino compound from disodium salt of 2-carboxy-methylamino- 3,5-dibromobenzoic acid and diazotized Coupling component Tint 1-amino-2-methoxy-4- 2-(2',3'-hydroxynaph- Red.
  • phenylether thoyl-amino)-naphthalene.
  • Diazoamino compound from disodium Salt o1 2-carboxymethylam1no- 5-bromobenzoic acid and diazotizcd.
  • Diazoamino compound from sodium salt 0t 2-fl-hydroxy-ethylaminobenzene-l-can boxylic acid-5-sulfomc acid dimethylamlde l-and diazotized.
  • Cotton yarn was treated at a goods to liquor ratio of 1:20 at about 20 C., in an aqueous solution containing, per liter, 1 g. of 2-(2,3'-hydroxynaphthoylamino)-3-methoxydiphenylene oxide, 1 g. of sodium salt of oleylmethyltaurine, 5.4 g. of sodium hydroxide and 4.8 g. of the diazoamino compound of the formula After about 45 minutes, 48 cc. of a 50% acetic acid were added per liter of bath and treatment was continued for about 30 minutes at a pH-value of about 4 which had adjusted itself; the yarn was thoroughly rinsed and soaped at first for 15 minutes at 60 C.
  • EXAMPLE 11 10 parts by weight of cotton yarn were treated in 200 parts by volume of an aqueous solution having 20 C. and containing 0.1% of 1-(5-hydroxy-1',2',1",2"-benz0- carbazole-4-carboylamino)-4-methoxy-benzene, 0.1% of the sodium salt of oleoylmethyl-taurine, 0.75% of sodium hydroxide and 0.48% of the diazoamino compound of the' formula 00H 200m EO N0. 5 K JOONa OONa After about 45 minutes, 6.8 parts by weight of a 50% acetic acid were added and treatment was continued for about 30 minutes.
  • the yarn was soaped at first for 15 minutes at 60 and then for 15 minutes at C. with an aqueous solution containing 0.2% of the sodium salt of oleylmethyl-taurine, 0.05% of the trisodium salt of nitrilotriacctic acid and 0.2% of sodium carbonate, rinsed again and dried. A dark brownish-Bordeaux dyeing exhibiting good fastness to rubbing was obtained.
  • EXAMPLE 12 10 parts by weight of cotton yarn were treated, at about 20 C. in a solution of 0.2 part by weight of 1-(5'-hydroxy-1',2',l",2-benzocarbazole 4' carboylamino)-2 methyl-4-methoxybenzene, 0.6 part by weight of a dispersing agent containing 1 6% of a condensation product of partially degraded caseine and palm nut oil fatty acid and 8% of a condensation product of a-ethyl-hexyl-chlorocarbonic acid ester and the sodium salt of m-ethylhexyltaurine, 1.5 parts by weight of sodium hydroxide and 0.96 part by weight of the diazoamino compound of the formula 0 on.
  • EXAMPLE 13 1 part by weight of cotton yarn was treated with 10 parts by volume of an aqueous solution containing, per liter, 1.6 g. of 2-(2',3-hydroxynaphthoyl-amino)-naphthalene, 1 g. of the sodium salt of oleoylmethyltaurine, 5.6 g. of sodium hydroxide, 30 g. of sodium chloride and 9.6 g. of the diazoamino compound of the formula (
  • the yarn was then rinsed, then soaped for 15 minutes at 60 C. and 15 minutes at the boiling ternperaturewith 10 parts by volume of an aqueous solution containing, per liter, 2 g. of the sodium salt of oleoylmethyl-taurine, 0.5 g. of the sodium salt of nitrilotriacetic acid and 1 g. of sodium carbonate, rinsed thoroughly and dried. A red dyeing exhibiting good fastness to rubbing was obtained. 1
  • Diazoamino compound from trisodium salt of l-carboxy-methylaminobenzene-2,5-dicarboxylic acid and diazotized Coupling component Tint;
  • a one bath exhaust dyeing process for the production of water-insoluble azo dyestuffs on cellulose or pr0 tein textile material comprising immersing the textile material in an aqueous alkaline dye bath which contains (1) a coupling component highly substantive for the textile material selected from the group consisting of arylamides of heterocyclic orthohydroxy carboxylic acids, mides of heterocyclic orthohydroxy carboxylic acids, arylamides of acyl acetic acids and arylamides of terephthaloyl-bis-acetic acid (2) alkali metal salts or alkaline 14 earth metal salts of a diazoarnino compound of the formula:
  • R stands for the radical of an aromatic amine having a dissociation constant of l.10
  • A stands for 0 lower-alkyl, hydroxyalkyl or carboxyalkyl
  • Y stands for hydrogen, halogen, nitro, carboxylic acid, sulfonic acid, alkylsulfonyl, aralkylsulfonyl, sulfonic acid arylester, sulfonic acid monoalkylamide, sulfonic acid dialkylamide, sulfonic acid piperidide or sulfonic acid morpholide and Z stands for hydrogen or halogen
  • Z stands for hydrogen or halogen
  • a dispersing agent and then subsequently adding to the dye bath containing the textile material, without intermediate drying, an acid agent selected from the group consisting of inor- 2 ganic mineral, organic carboxylic acids, and mixtures thereof at a temperature below 40 C.

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US442191A 1964-03-28 1965-03-23 Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers Expired - Lifetime US3502424A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEF42458A DE1262958B (de) 1964-03-28 1964-03-28 Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern
DE1964F0044682 DE1279638C2 (de) 1964-03-28 1964-12-12 Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern
DE1965F0045283 DE1297072C2 (de) 1964-03-28 1965-02-19 Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern
DE1965F0045301 DE1296122C2 (de) 1964-03-28 1965-02-20 Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern

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US442191A Expired - Lifetime US3502424A (en) 1964-03-28 1965-03-23 Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers

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US (1) US3502424A (enrdf_load_stackoverflow)
JP (1) JPS4942862B1 (enrdf_load_stackoverflow)
AT (1) AT259508B (enrdf_load_stackoverflow)
BE (1) BE661773A (enrdf_load_stackoverflow)
CH (1) CH461671A (enrdf_load_stackoverflow)
DE (4) DE1262958B (enrdf_load_stackoverflow)
DK (1) DK121294B (enrdf_load_stackoverflow)
GB (1) GB1092033A (enrdf_load_stackoverflow)
NL (1) NL6503893A (enrdf_load_stackoverflow)
NO (1) NO119987B (enrdf_load_stackoverflow)
SE (1) SE220331C1 (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040083560A1 (en) * 2001-03-08 2004-05-06 Jean-Marie Adam Method of clouring porous material

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1882560A (en) * 1928-05-07 1932-10-11 Gen Aniline Works Inc Manufacture of water-insoluble azo dyestuffs
US1882561A (en) * 1929-02-25 1932-10-11 Gen Aniline Works Inc Dyeing preparation
US2088506A (en) * 1934-04-06 1937-07-27 Du Pont Process and composition for applying and fixing diazoimino dyestuffs
DE1057061B (de) * 1957-12-21 1959-05-14 Hoechst Ag Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf pflanzlichen Fasern
US2897186A (en) * 1956-02-21 1959-07-28 Pharma Chemical Corp Diazoamino dye intermediates
US2926986A (en) * 1960-03-01 Solutions of diazoamino derivatives

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2926986A (en) * 1960-03-01 Solutions of diazoamino derivatives
US1882560A (en) * 1928-05-07 1932-10-11 Gen Aniline Works Inc Manufacture of water-insoluble azo dyestuffs
US1882561A (en) * 1929-02-25 1932-10-11 Gen Aniline Works Inc Dyeing preparation
US2088506A (en) * 1934-04-06 1937-07-27 Du Pont Process and composition for applying and fixing diazoimino dyestuffs
US2897186A (en) * 1956-02-21 1959-07-28 Pharma Chemical Corp Diazoamino dye intermediates
DE1057061B (de) * 1957-12-21 1959-05-14 Hoechst Ag Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf pflanzlichen Fasern

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040083560A1 (en) * 2001-03-08 2004-05-06 Jean-Marie Adam Method of clouring porous material
US7041143B2 (en) * 2001-03-08 2006-05-09 Ciba Specialty Chemicals Corporation Method of coloring porous material
AU2002253086B2 (en) * 2001-03-08 2007-04-05 Ciba Specialty Chemicals Holding Inc. Method of colouring porous material

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DE1297072B (de) 1969-06-12
JPS4942862B1 (enrdf_load_stackoverflow) 1974-11-18
NL6503893A (nl) 1965-09-29
GB1092033A (en) 1967-11-22
DE1296122C2 (de) 1973-02-22
DE1296122B (de) 1969-05-29
DE1279638B (de) 1968-10-10
DE1279638C2 (de) 1973-05-30
DK121294B (da) 1971-10-04
CH461671A (de) 1968-05-15
DE1262958B (de) 1968-03-14
DE1297072C2 (de) 1973-02-22
SE220331C1 (sv) 1968-05-07
NO119987B (enrdf_load_stackoverflow) 1970-08-10
BE661773A (fr) 1965-09-29
AT259508B (de) 1968-01-25

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