US3713767A - Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers - Google Patents

Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers Download PDF

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Publication number
US3713767A
US3713767A US00048429A US3713767DA US3713767A US 3713767 A US3713767 A US 3713767A US 00048429 A US00048429 A US 00048429A US 3713767D A US3713767D A US 3713767DA US 3713767 A US3713767 A US 3713767A
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United States
Prior art keywords
acid
disperse
dyeing
fibers
mixtures
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Expired - Lifetime
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US00048429A
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English (en)
Inventor
R Lowenfeld
U Kosubek
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Hoechst AG
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Hoechst AG
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/68Preparing azo dyes on the material
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8238Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
    • D06P3/8257Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and azo dyes prepared in situ
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • Y10S8/912Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber

Definitions

  • textile materials consisting of mixtures of polyester fibers and cellulose fibers can be dyed fast shades using disperse dyestuffs and water-insoluble azo dyestuffs produced on the fiber.
  • This process is effected in such a manner that first the polyester fiber portion is dyed with disperse dyestuffs at boiling temperature in the presence of dyeing accelerators, or under high temperature dyeing conditions or according to the so-called thermosol process, and then the water-insoluble azo dyestuff is produced on the cellulose fiber portion by impregnation with a coupling component and following development with a diazotized aromatic amine.
  • This method of operation yields dyeings of good quality. It is, however, very timeconsuming, since the disperse dyestuff, the coupling component and the diazotized aromatic amine have to be applied in separate baths.
  • the process of the present invention is effected by impregnating the textile material, for example a mixed fabric consisting of polyester and cellulosic fibers, with an alkaline solution which contains a coupling component, a disperse dyestuff as well as a wetting or dispersing agent, and then drying the material.
  • an alkaline solution which contains a coupling component, a disperse dyestuff as well as a wetting or dispersing agent, and then drying the material.
  • it is suitable to use a predrying tunnel after the impregnating foulard in order to avoid migration of the disperse dyestuff during drying and formation of unlevel parts by contact with the rolls.
  • the alkali content of the impregnation bath shall be so high that the coupling component does not precipitate. Depending on the nature and concentration of the coupling component, about ml.
  • the textile material is impregnated on a foulard or a nip-pad dyeing apparatus with a solution which contains a diazotized aromatic or heterocyclic amine as well as a dispersing agent and such a quantity of a substance having an acid reaction that the material to be dyed has a pH in the range offrom 4 to 7, after the passage or after the nip-padding. ln this pH- range the coupling component on the material couples with the diazotized amine, whereby the dyestuff is formed on the cellulose fiber portion of the mixed fabric.
  • the following drying process is suitably effected again in a drying tunnel, because the disperse dyestuff on the goods is not yet fixed and migration of this dyestuff portion or any influence effected by the guide rolls should be avoided to obtain level appearance of the goods.
  • the goods are treated for about 30 seconds to 2 minutes on a thermosoling apparatus at temperatures in the range of from about l2l0 C.
  • the heat treatment can be carried out with hot air or by contact heat.
  • the adjustment of the pH-value to about pH 4 to 7 on the goods in the treat ment with the acid solution of the diazotized amine is necessary in order to avoid damage of the cellulose fiber portion of the mixed fabric during the treatment with dry 'heat by too low a pH-value and, on the other hand, also in order to prevent the disperse dyestuff from being hindered by an alkaline medium to absorb evenly on the polyester fiber portion during the heat treatment.
  • the fabric is washed with an alkaline solution, rinsed and dried.
  • the water-insoluble azo dyestuff is obtained on the cellulose fiber portion in full yield and clearness.
  • the dyeings so produced have very good fastness properties.
  • the formation of the water-insoluble azo dyestuff on the cellulose fiber portion takes place when the goods, that have been impregnated with the coupling component and the disperse dyestuff, are introduced into the acid development bath in the presence of the disperse dyestuff, without the latter being at first fixedon the polyester fiber portion.
  • the fixation of the disperse dyestuff on the polyester fiber portion is effected in the following heat treatment at temperatures in the range of from l702l0 C.
  • mixtures may be used which contain from 25 percent of polyester fibers and percent of cellulose fiber to 70 percent of polyester fibers and 30 percent of cellulose fibers.
  • polyester fibers those made of aromatic polyesters, for example of terephthalic acid or diphenyl-4,4'-dicarboxylic acid and alkanediols or 1,4- cyclohexanedimethanol, as well as of triacetylcellulose are suitable.
  • cellulose fibers natural and regenerated cellulose fibers may be used.
  • aromatic ohydroxycarboxylic acid arylamides or acylacetic acid arylamides may be used in the process of the invention, for example, 2,3-hydroxynaphthoic acid arylamides, 6- bromoor 6-alkoxy-2, -3-hydroxynaphthoic acid arylamides or acetoacetic acid arylamides, which have a low to medium substantivity towards cellulose fibers.
  • coupling components which have a highvsubstantivity towards the cellulose fibers, for example the condensation products of 2,3-hydroxynaphthoic acid with polynuclear isocyclic or heterocyclic amines such as aminonaphthalenes, aminocarbazoles or aminodiphenylene-oxides, furthermore heterocyclic ohydroxycarboxylic acid arylamides, for example 5- hydroxy-l ,2,l ,2-benzocarbazole-4-carboxylic acid arylamides, 2-hydroxy-carbazole-l or -3-carboxylic acid arylamides as well as 4,4-bisacetoacetylaminodiphenyls or 2-hydroxyanthracene-3- carboxylic acid arylamides.
  • coupling components which have a highvsubstantivity towards the cellulose fibers, for example the condensation products of 2,3-hydroxynaphthoic acid with polynuclear isocyclic or heterocyclic amines such as aminona
  • diazotized primary aromatic or heterocyclic amines mono-or diamines for example diazotized 'nitroanisidines
  • chloroanilines dichloro-anilines, chloro-anisidines, nitranilines, nitrotoluidines, nitroxylidines, nitrophenetidines, cyanotoluidines, cyanoanisidines, amino benzene-sulfonic acid amides, aminobenzene -carboxylic acid amides, aminophenylalkyl-, -arylor -aralkyl-sulfones, aminodiphenylethers, trifluoromethyl'anilines, monoacylated phenyle nediamines, aminoazobenzenes or 4- aminodiphenylamines as well as tetrazotized 4,4- diaminodiphenyls may be used.
  • condensation products of higher molecular fatty acids and protein degradation products condensation products of higher molecular fatty acids and aminoalkylsulfonic acids, condensation products of formaldehyde and naphthalene-sulfonic acids as well as purified sulfite cellulose waste liquor may be used.
  • organic acids for example, acetic acid, formic acid, propionic acid, lactic acid, glycolic acid, tartaric acid or citric acid, or salts having an acid reaction, for example sodium mono-phosphate, aluminum sulfate, or zinc sulfate may be used.
  • non-volatile acid compounds care must be taken not to use a higher quantity than is necessary for the neutralization of the alkali which is on chloro-toluidines the goods, in order to prevent a damage of the cellulose fiber portion during'the following heat treatment.
  • disperse dyestuffs such dyestuffs may be used which on account of their thermal properties can be used in the so-called thermosol process, i.e., dyestuffs which dye polyester fibers at temperatures in the range of from about 170 to 210 C and which do not soil the dyeing apparatus due to their high volatility.
  • the dyestuffs must be stable against the lye present in the impregnation bath, for example, they-must not tend to coagulation during the about two hours stay in the impregnation bath.
  • Suitable disperse dyestuffs of the azo and anthraquinone series are described in the Color-lndex, second edition 1956, vol. 1, pages l6591742 and Supplement 1963, pages S 179-224 as well as in the corresponding Additions and Amendments, No. 1 (September 1963) to N0. 22 (January 1969).
  • the process of the invention may be executed in continuous as well as in semi-continuous manner.
  • the disperse dyestuff is fixed in a first stage on the polyester fiber portion of the mixed fabric by a thermosol the application of the disperse dyestuff with the preparation of the water-insoluble azo dyestuff on the cellulose fiber portion of the mixed fabric and to save thereby one stage of operation.
  • the fabric was then squeezed to a bath absorption of 60 percent of the weight of the fabric, dried and impregnated with a solution containing, per liter of water, 10.6 g of diazotized l-amino-2-methyl-4- chlorobenzene, 21 ml of percent acetic acid, 20 g of sodium acetate and 2 g of a reaction product of about 20 mols of ethylene oxide and 1 mol of octadecylalcohol.
  • the fabric was then squeezed to a bath absorption of percent of the weight of the fabric and conducted through a drying apparatus in such a manner into a thermosoling chamber or over hot rolls that'the fabric was heated for 3060 seconds to a temperature in the range of from 180 to 210 C.
  • the fabric was treated at boiling temperature with a solution containing, per liter of water, 2 g of a 30 percent reaction product of about 10 mols of ethylene oxide and 1 mol of nonylphenol, and 2 ml of a 25 percent solution of the sodium salt of nitrilo-triacetic acid, and the fabric was then rinsed hot and cold.
  • the after-treatment of the dyeing can also be effected at 60 C or 95 in a bath which contains per liter of water, 3 g of a mixture of 63 percent of perchloroethylene, 17 percent of a reaction product of about 10 mols of ethylene oxide and 1 mol of nonylphenol and 20 percent at isopropyl alcohol, and 2 g of a 25 percent solution of the sodium salt of nitrilo-triacetic acid. A full red dyeing having good fastness properties was obtained.
  • Coupling component Disperse dyestuff Diazotized amine Shade 2,3-hyclroxynaphthoylaminobenzene.
  • C.I. Disperse Red 1-am1no-2-methy1-5-ch1orobenzene Yellowish red. 1(2,3-h ydroxynapth oylamin0)-2- .do .do D0.
  • a process for dyeing textile materials consisting of mixtures of polyester and cellulose fibers, which comprises treating the textile material with alkaline solutions containing a coupling component, at least one disperse dyestuff, as well as wetting or dispersing agents, drying the material and subsequently treating it with acid solutions which contain, in addition to compounds giving an acid reaction, a diazotized aromatic or heterocyclic amine, drying the material and then subjecting it to a heat treatment.
  • the coupling component is an aromatic or heterocyclic ohydroxy-carboxylic acid aryl amide or an acylacetoaryl amide.
  • the wetting or dispersing agent is a condensation product of a long chain fatty acid and an aminoallryl sulfonic acid or of formaldehyde and a naphthalene sulfonic acid or a purified waste lignin liquor.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US00048429A 1969-06-24 1970-06-22 Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers Expired - Lifetime US3713767A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691931881 DE1931881A1 (de) 1969-06-24 1969-06-24 Verfahren zum Faerben von Textilmaterial aus Mischungen von Polyesterfasern mit Cellulosefasern

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US3713767A true US3713767A (en) 1973-01-30

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US00048429A Expired - Lifetime US3713767A (en) 1969-06-24 1970-06-22 Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers

Country Status (7)

Country Link
US (1) US3713767A (enrdf_load_stackoverflow)
AT (1) AT299115B (enrdf_load_stackoverflow)
BE (1) BE752444A (enrdf_load_stackoverflow)
CH (2) CH533725A (enrdf_load_stackoverflow)
DE (1) DE1931881A1 (enrdf_load_stackoverflow)
FR (1) FR2047913B1 (enrdf_load_stackoverflow)
GB (1) GB1309790A (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3961886A (en) * 1973-09-15 1976-06-08 Hoechst Aktiengesellschaft Process for the dyeing and printing of cellulose-containing textile materials
US3961884A (en) * 1973-09-15 1976-06-08 Hoechst Aktiengesellschaft Process for dyeing textile material of polyester fiber/cellulose blends
US4017256A (en) * 1974-03-28 1977-04-12 Ciba-Geigy Corporation Process for the printing and pad-dyeing of mixed fabric
US4094636A (en) * 1976-01-30 1978-06-13 Hoechst Aktiengesellschaft Process for dyeing cellulose fibers with water-insoluble azo dyestuffs produced on the fiber
DE2847532A1 (de) * 1978-11-02 1980-05-08 Bayer Ag Verfahren zur herstellung von azofarbstoffen
US4212648A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of cellulose fiber fabrics
US4212646A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of mixed fabrics of polyester and cellulose fibers
US4414000A (en) * 1980-07-30 1983-11-08 Hoechst Ag Process for the continuous or semicontinuous dyeing of voluminous cellulose fabrics with azo developing dyestuffs using acrylamide polymers
US4433976A (en) 1980-07-30 1984-02-28 Hoechst Ag Process for the semicontinuous dyeing of tubular knitted fabrics of cellulose fibers with azo developing dyestuffs
US5695375A (en) * 1994-03-01 1997-12-09 Kuraray Co., Ltd. Disperse dye-dyeable regenerated cellulose fiber and textile products containing the fiber

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3100132A (en) * 1960-01-27 1963-08-06 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters
US3416873A (en) * 1967-10-11 1968-12-17 Otto B May Inc Polyester dyeing with 1-(2-methoxy-4-nitrobenzeneazo) - 2 - hydroxy-11h-benzo (a)carbazole-3-carbox-p-anisidide
US3623831A (en) * 1968-04-30 1971-11-30 Hoechst Ag Process for dyeing textile material of mixtures of polyester and cellulose fibres

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3100132A (en) * 1960-01-27 1963-08-06 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters
US3416873A (en) * 1967-10-11 1968-12-17 Otto B May Inc Polyester dyeing with 1-(2-methoxy-4-nitrobenzeneazo) - 2 - hydroxy-11h-benzo (a)carbazole-3-carbox-p-anisidide
US3623831A (en) * 1968-04-30 1971-11-30 Hoechst Ag Process for dyeing textile material of mixtures of polyester and cellulose fibres

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DuPont, Bulletin D 238, March 1970 *
Wygand, Am. Dye. Rep., Dec. 7, 194, 106 108 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3961886A (en) * 1973-09-15 1976-06-08 Hoechst Aktiengesellschaft Process for the dyeing and printing of cellulose-containing textile materials
US3961884A (en) * 1973-09-15 1976-06-08 Hoechst Aktiengesellschaft Process for dyeing textile material of polyester fiber/cellulose blends
US4017256A (en) * 1974-03-28 1977-04-12 Ciba-Geigy Corporation Process for the printing and pad-dyeing of mixed fabric
US4094636A (en) * 1976-01-30 1978-06-13 Hoechst Aktiengesellschaft Process for dyeing cellulose fibers with water-insoluble azo dyestuffs produced on the fiber
US4212648A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of cellulose fiber fabrics
US4212646A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of mixed fabrics of polyester and cellulose fibers
DE2847532A1 (de) * 1978-11-02 1980-05-08 Bayer Ag Verfahren zur herstellung von azofarbstoffen
US4414000A (en) * 1980-07-30 1983-11-08 Hoechst Ag Process for the continuous or semicontinuous dyeing of voluminous cellulose fabrics with azo developing dyestuffs using acrylamide polymers
US4433976A (en) 1980-07-30 1984-02-28 Hoechst Ag Process for the semicontinuous dyeing of tubular knitted fabrics of cellulose fibers with azo developing dyestuffs
US5695375A (en) * 1994-03-01 1997-12-09 Kuraray Co., Ltd. Disperse dye-dyeable regenerated cellulose fiber and textile products containing the fiber

Also Published As

Publication number Publication date
AT299115B (de) 1972-06-12
FR2047913A1 (enrdf_load_stackoverflow) 1971-03-19
GB1309790A (en) 1973-03-14
FR2047913B1 (enrdf_load_stackoverflow) 1976-02-06
BE752444A (fr) 1970-12-24
CH942070A4 (enrdf_load_stackoverflow) 1972-10-31
DE1931881A1 (de) 1971-02-18
CH533725A (de) 1972-10-31

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