US3920386A - Process for the single-bath dyeing of cellulose fibers or mixtures thereof with synthetic fibers with water-insoluble azo dyestuffs produced on the fiber by the exhaustion method - Google Patents

Process for the single-bath dyeing of cellulose fibers or mixtures thereof with synthetic fibers with water-insoluble azo dyestuffs produced on the fiber by the exhaustion method Download PDF

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US3920386A
US3920386A US341363A US34136373A US3920386A US 3920386 A US3920386 A US 3920386A US 341363 A US341363 A US 341363A US 34136373 A US34136373 A US 34136373A US 3920386 A US3920386 A US 3920386A
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Prior art keywords
fibers
water
coupling
alcohol
acid
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Expired - Lifetime
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US341363A
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English (en)
Inventor
Egon Beyer
Der Eltz Hans-Ulrich Von
Erich Schuster
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Hoechst AG
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Hoechst AG
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Priority claimed from DE19722213241 external-priority patent/DE2213241C3/de
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Publication of US3920386A publication Critical patent/US3920386A/en
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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
    • D06P1/00General 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
    • D06P1/44General 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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General 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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • 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
    • D06P1/00General 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
    • D06P1/36General 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 mordant dyes ; using metallisable dyes
    • 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
    • D06P1/00General 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
    • D06P1/44General 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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General 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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • 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
    • D06P1/00General 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
    • D06P1/44General 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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General 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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651Compounds without nitrogen
    • D06P1/65106Oxygen-containing compounds
    • 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
    • D06P3/82Textiles 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
    • D06P3/8228Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • 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

  • ABSTRACT Process for the single-bath dyeing of cellulose fibers and their mixtures with synthetic fibers with waterinsoluble azo dyestuffs produced on the fiber according to the exhaustion method, wherein an aqueous dyebath is allowed to act on the textile material, at room temperature or moderately elevated temperature, which liquor contains, in addition to alkaline substances, sodium nitrite and an anionic dispersing system, the solution or dispersion of at least one component capable of .entering into azo coupling and at least one non-diazotized primary aromatic amine in a medium on the basis of a water-miscible organic solvent or solubilizer, and after absorption of the coupling component, the diazotization of the amine and the dyestuff formation by coupling is caused in that acid or acid salts are added to the dyeing bath at room temperature.
  • the present invention concerns a process for the single-bath dyeing of cellulose fibers or mixtures thereof with synthetic fibers with water-insoluble azo dyestuffs produced on the fiber by the exhaustion method.
  • German Pat. No. 729,846 describes a process wherein, within the scope of the calico printing of cellulose fihers, both the coupling component and the diazotable primary aromatic amine in one printing paste is printed on the goods together with the sodium nitrite and the az'o dyestuff is then developed by a passage through an acid; A further process is known from German Pat. No.
  • 1,262,957 according to which coupling components are applied on the textile material according to the exhaustion method in a single bath with stabilized dior tet razoamino compounds of primary amines which are resistant to alkalies and the dyestuff is developed on the fiberby adding an acid to the bath.
  • the present invention is based on the observation that cellulose fibers and their mixtures with synthetic fibers, preferably polyester fibers, can be dyed according to the exhaustion method in a single bath with water-insoluble azo dyestuffs produced on the fiber if an aqueous liquor is allowed to act on the textile material, at room temperature or moderatelyelevated temperature, which liquor contains, in addition to alkaline substances, sodium nitrite and an anionic dispersing system, the solution or dispersion of at least one component capable of entering into azo coupling and at least one non-diazotized primary aromatic amine in a medium on the basis of water-miscible organic solvent or solubilizer and after absorption of the coupling component, the diazotization of the amine and the formation of the dyestuff by coupling on the fiber are then effected by adding acid or acid salts to the dyeing bath at room temperature.
  • the primary aromatic amines which are water-insoluble in an alkaline medium are made clearly soluble or prefectly dispersible by means of suitable means in order to keep the dyebaths stable without any precipitations both in the impregnating phase within the alkaline range and in the developing phase within the acid range.
  • suitable solvents and a dispersing system which is effective in both process steps.
  • the coupling components sufficiently known from the ice color technique, those being used according to the present invention which have a substantivity effect towards fibrous material.
  • Such compounds are those which couple in a neighbouring position to a hydroxy group and do not have solubilizing groups, particularly aryl amides of aromatic or heterocyclic o-hydroxycarboxylic acids or acylacetic acids and other aromatic or heterocyclic hydroxyl compounds and compounds containing an enolizable or enolized ketomethylene group in a hetrocyclic ring.
  • Such substances are, for example arylamides of the 2,3-hydroxynaphthoic acid, 2-hydroxyanthracene- 3-carboxylic acid, 4-hydroxydiphenyl-3-carboxylic acid, 2-hydroxy-carbazole-3-carboxylic acid, 3-hydroxydiphenylene-oxide-2-carboxylic acid, 3-hydroxydiphenylene sulfide-2-carboxylic acid, 'acetoacetic acid or benzoylacetic' acid.
  • hydroxybenzenes polyhydroxybenzenes, hydroxynaphthalen es and pyrazolones which may be substituted by non-ionic. radicals proved to besuitable.
  • the process of the present invention can be applied to the known cellulosic fibers and mixtures of synthetic fibers, for example polyester fibers, and cellulose fibers.
  • Cellulose fibers in question are in this connection native fibers such as flax, hemp, linen and cotton, or regenerated fibers suc'has viscose staple fiber, spun rayon and modal fibers (polynosic type).
  • the proposed quantity of the'coupling component is dissolved in the usual manner according to the cold dissolving method. preferably with ethanol, sodium hydroxide solution and water, without adding formaldehyde.
  • the primary, aromatic amine is separately dissolved in one of the alcohols mentioned sub l) or in another suitable solvent such as dimethyl sulfoxide, dimethyl formamide, diacetone alcohol, dimethyl acetamide, tetrahydrofurfuryl alcohol, glycerin, or methoxy butanol.
  • This solution or these solutions are stirred into a bath having a temperature of 30C and consisting of soft water, sodium hydroxide solution, sodium nitrite, crystallized disodium phosphate, sodium chloride and, as dispersing agent, the sodium salt of 2,2'-dinaphthylmethane-6,6-disulfonic acid or a mixture of equal parts of oleylmethyltaurine andlignin sulfonate.
  • dispersing agent the sodium salt of 2,2'-dinaphthylmethane-6,6-disulfonic acid or a mixture of equal parts of oleylmethyltaurine andlignin sulfonate.
  • anionic dispersing agents are also applied after the azo coupling reaction.
  • the textile material of cellulose fibers is first treated for 30 to 45 minutes at 30C with this bath at a goodsto-liquor ratio of l 10 to l 30 (in an apparatus consisting of open vat and winch vat), the material is then taken out of the bath or the liquor is pumped back into the preparing vessel, and l ml/l of hydrochloric acid of 20B and 0.1 ml/l of acetic acid of 60 strength are added per each 1 ml/l of sodium hydroxide solution of 32.5 7c strength (38 B) total lye).
  • the pH of the dyeing bath is adjusted to 5.8 to 6.0 whereby the diazotization of the primary aromatic amine and the coupling to the azo dyestuff sets in simultaneously and is finished within 30 minutes during which the goods are treated at 25 30C.
  • disodium phosphate prescribed as buffer reacts with the simultaneously present sodium hydroxide solution to trisodium phosphate, it must be used according to this invention.
  • the commercial product crystallized disodium phosphate (dodecahydrate, Na HPO .l2H O) always contains the same quantity of crystal water per mole. From the trisodium phosphate, however, products with varying content of crystal water are available. thus the application of which could cause differences in the pH-range aspired to.
  • the dyeings are then subjected to a subsequent treatment in the usual manner by a thorough rinsing in cold and hot water and by a soaping at 60C and boiling temperature with sodium carbonate, a detergent and polyphosphate.
  • an acid quantity for the formation of the salt of the amine e.g. hydrochloride
  • an acid quantity for the formation ofN O or HNO from the sodium nitrite
  • the dyebath was pumped back into the preparing vessel and ml of hydrochloric acid of B and mill of acetic acid of 60 71 strength were added thereto.
  • the goods were treated for 30 minutes at C with this dyebath having a pH value of about 5.9, the dyed bobbins were then rinsed with cold and hot water, soaped for 15 minutes at 60C 30 and 15 minutes at boiling temperature with an aqueous A full red dyeing having very good fastnesses was obtained.
  • a process for the single-bath dyeing of cellulose fibers and mixtures thereof with polyester fibers, with water-insoluble azo dyestuffs produced on the fibers by the exhaust method comprising the steps of: contacting a textile material containing the said fibers, at room temperature or moderately elevated temperature, with an aqueous dyebath containing, an alkaline substance,
  • Example 2 l 5 g/l Azoic Coupling Component 35-C.l. 37 6l5 Example 3 1.5 g/l 28-0]. 37 54l Example 4 1.5 g/l 8-C.l. 37 525 Example 5 1.5 g/l 23-C.l. 37 555 Example 6 1.5 g/l 4-C.l. 37 560 Example 7 L5 g/l l3-C.l. 37 595 Example 8 1.5 g/l l5-C.l. 37 600 Primary aromatic amine Example 2 l g/l Azoic Diazo Component 32-C.l. 37 090 Example 3 L2 g/l 2-C.l. 37 005 Example 4 1.5 g/l 32-C.l.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US341363A 1972-03-18 1973-03-15 Process for the single-bath dyeing of cellulose fibers or mixtures thereof with synthetic fibers with water-insoluble azo dyestuffs produced on the fiber by the exhaustion method Expired - Lifetime US3920386A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19722213241 DE2213241C3 (de) 1972-03-18 Verfahren zum einbadigen Färben von Cellulosefasern oder deren Mischungen mit synthetischen Fasern mit auf der Faser erzeugten wasserunlöslichen Azofarbstoffen nach der Ausziehmethode

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Country Status (9)

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US (1) US3920386A (en, 2012)
JP (1) JPS4912180A (en, 2012)
AR (1) AR193928A1 (en, 2012)
BR (1) BR7301886D0 (en, 2012)
CA (1) CA992705A (en, 2012)
CH (2) CH569832B5 (en, 2012)
FR (1) FR2176856B1 (en, 2012)
GB (1) GB1422995A (en, 2012)
IT (1) IT982557B (en, 2012)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094636A (en) * 1976-01-30 1978-06-13 Hoechst Aktiengesellschaft Process for dyeing cellulose fibers with water-insoluble azo dyestuffs produced on the fiber
US4094637A (en) * 1974-10-19 1978-06-13 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4195973A (en) * 1977-11-02 1980-04-01 Hoechst Aktiengesellschaft Process for printing with developing dyes which employs having ether substituents derived from glycols, polyglycols, or alkoxy derivatives thereof
US4242094A (en) * 1976-03-17 1980-12-30 Hoechst Aktiengesellschaft Dyeing preparations and their use for preparing developing dyes
US4638099A (en) * 1985-02-27 1987-01-20 Rohm Gmbh Method for making 4,4'-dihydroxydiphenyl ether
US5512062A (en) * 1994-03-29 1996-04-30 Ful-Dye, Inc. Low temperature textile dyeing method using high temperature dye compositions
CN101935902A (zh) * 2010-09-02 2011-01-05 齐齐哈尔大学 一种亚麻混纺针织纱的生产方法
US20160348038A1 (en) * 2004-09-23 2016-12-01 The Sun Products Corporation Laundry Treatment Compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5139124A (ja) * 1974-09-30 1976-04-01 Asahi Chemical Ind Higinenkeikankozairyono genryokuhoho
JPS5665129A (en) * 1979-10-31 1981-06-02 Oriental Shashin Kogyo Kk Dry type image forming material
ITMI20020204A1 (it) * 2002-02-05 2003-08-05 Pinuccio Giordano Procedimento per la tintura di materiale tessile

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2030859A (en) * 1933-09-12 1936-02-18 Gen Aniline Works Inc Textile assistants
US2845326A (en) * 1955-08-08 1958-07-29 Gen Aniline & Film Corp Diazotizable amine compositions
US3000298A (en) * 1956-01-03 1961-09-19 Sherman Printing by diazotization
US3029122A (en) * 1956-12-31 1962-04-10 Gen Aniline & Film Corp Ice color coupling component composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB276100A (en) * 1926-06-07 1927-08-25 Chem Fab Vormals Sandoz Improvements in or relating to the dyeing of effect threads
FR882436A (fr) * 1941-06-11 1943-06-02 Ig Farbenindustrie Ag Procédé pour la teinture et l'impression de matières formées de superpolyamides synthétiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2030859A (en) * 1933-09-12 1936-02-18 Gen Aniline Works Inc Textile assistants
US2845326A (en) * 1955-08-08 1958-07-29 Gen Aniline & Film Corp Diazotizable amine compositions
US3000298A (en) * 1956-01-03 1961-09-19 Sherman Printing by diazotization
US3029122A (en) * 1956-12-31 1962-04-10 Gen Aniline & Film Corp Ice color coupling component composition

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094637A (en) * 1974-10-19 1978-06-13 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4094636A (en) * 1976-01-30 1978-06-13 Hoechst Aktiengesellschaft Process for dyeing cellulose fibers with water-insoluble azo dyestuffs produced on the fiber
US4242094A (en) * 1976-03-17 1980-12-30 Hoechst Aktiengesellschaft Dyeing preparations and their use for preparing developing dyes
US4195973A (en) * 1977-11-02 1980-04-01 Hoechst Aktiengesellschaft Process for printing with developing dyes which employs having ether substituents derived from glycols, polyglycols, or alkoxy derivatives thereof
US4638099A (en) * 1985-02-27 1987-01-20 Rohm Gmbh Method for making 4,4'-dihydroxydiphenyl ether
US5512062A (en) * 1994-03-29 1996-04-30 Ful-Dye, Inc. Low temperature textile dyeing method using high temperature dye compositions
US20160348038A1 (en) * 2004-09-23 2016-12-01 The Sun Products Corporation Laundry Treatment Compositions
US10106762B2 (en) * 2004-09-23 2018-10-23 Henkel IP & Holding GmbH Treating a textile garment with a hydrophobic dye solution
CN101935902A (zh) * 2010-09-02 2011-01-05 齐齐哈尔大学 一种亚麻混纺针织纱的生产方法

Also Published As

Publication number Publication date
CH569832B5 (en, 2012) 1975-11-28
FR2176856A1 (en, 2012) 1973-11-02
JPS4912180A (en, 2012) 1974-02-02
CH372873A4 (en, 2012) 1975-06-30
CA992705A (en) 1976-07-13
BR7301886D0 (pt) 1974-07-25
AR193928A1 (es) 1973-05-31
FR2176856B1 (en, 2012) 1976-09-10
DE2213241A1 (de) 1973-09-20
IT982557B (it) 1974-10-21
GB1422995A (en) 1976-01-28
DE2213241B2 (de) 1976-11-11

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