US3876370A - Dyeing synthetic and natural fibers with the liquid ammonia and chloroform or methylene chloride solution of a dye - Google Patents

Dyeing synthetic and natural fibers with the liquid ammonia and chloroform or methylene chloride solution of a dye Download PDF

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Publication number
US3876370A
US3876370A US329680A US32968073A US3876370A US 3876370 A US3876370 A US 3876370A US 329680 A US329680 A US 329680A US 32968073 A US32968073 A US 32968073A US 3876370 A US3876370 A US 3876370A
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United States
Prior art keywords
dyestuff
improvement defined
dyeing
liquid ammonia
improvement
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Expired - Lifetime
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US329680A
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English (en)
Inventor
Walter Birke
Walter Leischner
William Mcdowell
Rudolf Weingarten
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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
    • 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
    • D06BTREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B19/00Treatment of textile materials by liquids, gases or vapours, not provided for in groups D06B1/00 - D06B17/00
    • 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
    • D06P1/81General 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 dyes dissolved in inorganic solvents
    • 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
    • D06P1/90General 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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92General 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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922General 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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
    • D06P1/924Halogenated 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
    • D06P1/90General 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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92General 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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928Solvents other than hydrocarbons
    • 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
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile
    • 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
    • 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
    • Y10S8/924Polyamide fiber
    • 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
    • Y10S8/927Polyacrylonitrile fiber

Definitions

  • ABSTRACT Process for dyeing textile materials of natural or synthetic fibers alone or in mixture with each other, by treating the fibrous material with a solution of suitable dyestuffs in anhydrous, liquid ammonia alone or in mixture with low boiling organic solvents, within the range below the boiling point of the dyebath, and fixing the dyestuffs applied after removal of the ammonia remaining in the material in known manner typical for the dyestuffs or the dyegoods used.
  • Tedeco-Process Nawegian Textile Research Institute in cooperation with the Norwegian Central Institute for Industrial Research
  • Tedeco-Process Nawegian Textile Research Institute in cooperation with the Norwegian Central Institute for Industrial Research
  • the ammonia absorbed is then removed by passing the goods over heated cylinders and recovered for further utilization, Due to this treatment the goods shrink, show an improved dye-ability and appearance, a higher resistance to wear and tear and a higher stability of dimensions.
  • the textile goods are drawn, a higher strength is obtained.
  • Mixtures of polyester and cotton fibers can be treated likewise. The properties of the cotton component are thereby improved without impairment of those of the polyester fiber.
  • the present invention is based on the observation that liquid ammonia is a good solvent for dyestuffs.
  • liquid ammonia is a good solvent for dyestuffs.
  • disperse, pigment, reactive, acid, metal complex and cationic dyestuffs irrespective of their chemical constitution can be dissolved in liquid ammonia in concentrations which are generally sufficient for dyeing operations.
  • Such dyestuff solutions for example are suitable as treating baths for dipping, pad ding and spraying oftextile material in the form of slubbing, cables, filaments, knitted, woven and non-woven fabrics.
  • the present invention concerns a process for dyeing textile material made from natural or synthetic fibers alone or in mixture with each other wherein the fiber material is treated with a solution of suitable dyestuffs in anhydrous, liquid ammonia alone or in mixture with low boiling organic solvents within the range below the boiling point of the dyeing bath,.and the dyestuffs are fixed after removal of the ammonia remaining in the goods in known manner which is typical for the dyestuffs or dyegoods used.
  • the plants in which the treatment of the textile materials is to be carried out are adapted to the physical and chemical properties of the liquid ammonia.
  • the materials used have to resist the low temperatures below the boiling point of the ammonia of -3 3C and also a possible dissolving effect or corrosion by the ammonia.
  • the entire dyeing plant consists mainly of a dissolving and preparing vessel with stirring arrangement and filter for preparing the dye bath, a liquor application machine, for example a padding foulard with trough or a spraying device, a heatable mechanism such as a hollow roller to remove the ammonia after the treatment, and a recovering device for the ammonia.
  • the aforementioned dyeing apparatus is made air-tight by inlet and outlet roller locks. The experiences of the compressor cooling technique and the dry cleaning, and the latest knowledge of the dyeing technique with solvents as well as of the aforementioned pretreatment of the cotton with liquid ammonia have been utilized in the present invention.
  • the dyestuff selected according to the fibers to be dyed and eventually according to its solubility is dis' solved while stirring with a stirring mechanism in the preparing vessel outlined hereinbefore.
  • this dyestuff is in the form ofa commercial product it generally still contains extenders for setting a constant portion of the coloring substance which agents are often insoluble in liquid anhydrous ammonia.
  • the solution of the dyestuff is passed through a filter device to the storage vessel, for example the pad trough, the extender remaining in the filter.
  • the dyestuff does not contain an extender for example in the case of pigments or dyestuffs without any auxiliary agents, a filtration is unnecessary.
  • the textile material is impregnated either by dipping and squeezing, dipping and sucking off or spraying. It may be that the liquid ammonia contains portions of extremely low boiling organic solvents which thereby form azeotropic mixtures and may be jointly regenerated as it is known from the refrigeration technique.
  • the ammonia is removed by allowing it to evaporate for example by passing it over a heated roller or simply by reducing the pressure in the closed dyeing vessel, and fed back in the recovering system, eventually by compression and cooling, in liquid form into the circulation.
  • the textile material leaves the dyeing plant in dry condition and is further treated for its mostly thermical fixing depending on the type of the fiber and the dyestuff used.
  • the application and fixation may be effected by one of the known techniques, for example the pad-batch, two bath-pad-steaming or wet-fixation process.
  • Disperse dyestuffs on polyester fibers are fixed by pressure steam, solvent steam or thermosoling.
  • Cationic (basic) dyestuffs on acrylic or acid-modified polyester fibers are fixed by steaming.
  • the disperse dyestuff on the polyester fiber portion is fixed thermosoling
  • the re active dyestuff on the cellulose fiber portion is fixed by one of the known two-phase techniques.
  • Unfixed dyestuff portions have to be removed after fixing if necessary by an after-treatment.
  • the following textile materials can be dyed according to the process of-the present invention: natural and regenerated cellulose fibers, polyester and modified polyester fibers, polyamide and modified polyamide, polyurethane, polyolefin and modified polyolefin fibers as well as polyacrylic fibers, and other fibers which can be dyed with disperse, reactive and cationic dyestuffs.
  • solvent-mixture component In the case of the application of mixtures from liquid ammonia and organic solvents as dyeing medium there are especially used as solvent-mixture component according to the present invention alcohols such as methanol. ethanol, iso-propanol and n-butanol, furthermore acetone, dimethyl sulfoxide and dimethyl formamide.
  • halogenated hydrocarbons for example methylene chloride or chloroform dissolved in an excess of ammonia the boiling point of the dyeing medium can be advantageously raised.
  • the apparatus used consisted of a preparing vessel, a padding foulard, a heatable roller for removing the ammonia, inlet and outlet roller locks and a system for recovering the ammonia with compressor and cooler. When passing the heatable roller, the ammonia was removed from the textile material by evaporation and the goods left the apparatus in dry condition.
  • the dyestuff applied in this manner was fixed by steaming for 30 minutes under a pressure of 0.2 atmospheres gauge, the goods were rinsed cold and soaped at 95C with an aqueous dyebath containing 1 g/l of a non-ionic detergent of the type of the reaction product from 1 mol of nonylphenol and mols of ethylene oxide.
  • EXAMPLE 4 The dyeing was carried out as described in Example 3 but with piece goods of grey viscose rayon and in a bath containing 10 g/l of the reactive dyestuff (U.S. Pat. No. 3,135,730) of the formula 50311 dissolved in liquid ammonia.
  • EXAMPLE 5 Piece goods of linear polyethyleneglycol terephthalate were padded asdescribed in Example 1 with a dye- 6 bath Containing 5 g/ 0f e a nso e pigm dissolved in liquid ammonia at 60C, and then wound dy t ff COYFBSPOHdiHg t0 the formula up. Fixation of the dyestuff and after-treatment of the dyed goods was carried out as described in Example 5.
  • the polyester portion of the mixed fabric was dyed orange tints.
  • the properties of fastness corresponded 01 to those ofa dyeing obtained from an aqueous medium.
  • the goods were then treated for 15 seconds at boiling temperature in a heated trough of the open-width washing machine with an aqueous bath containing 250 g/l of sodium chloride and 50 ml/l of sodium hydroxide solution of 32.5 perdissolved in liquid ammonia at 40C.
  • the filaments cent Strength (38Be) and then Subjected to the follow thus treated were then passed through a heated cylining Cleaning Operations in the 8 boxes f the Opender.
  • This apparatus was air-tight as the equipment menwidth washing machine; tioned in Example 1 and provided with an ammonia re- 1 i i at 40 i Water covering device.
  • the filaments were then wound offin 2 d b idif i at 40C i h an aqueous b th strands and the dyestuffwas fixed for 20 minutes under Containing 1 m f acetic acid f 30 percent a pressure of 1.5 atmospheres gage in a high tempera- Strength ture star steamer.
  • 3rd box rinsing at C with water A brilliant light yellow dyeing was obtained.
  • the warp was then interwoven with the weft yarn of viscose rayon staple fiber yarn.
  • the piece goods thus obtained were then subjected on the jig during 4 passages at 60C to the influence of an aqueous solution of 1 g/l of a non-ionic detergent on the basis of the reaction product from 1 mol of nonylphenol and 10 mols of ethylene oxide and after-treated by repeated rinsing.
  • the treated fabric had the character ofa Denim article with blue polyamide warp and white staple fiber weft yarn.
  • EXAMPLE 10 Piece goods of polyamide o-filaments were treated as described in Example 1 with a bath containing 10 g/l of a chromium complex compound of the dyestuff (coupling product of diazotized 2-aminophenol-5-sulfonic acid dimethylamide with 3-methyl-5-hydroxy-pyrazol chromium complex) of the formula dissolved in liquid ammonia at -50C, and then steamed for 45 minutes at 104C in a star steamer. The dyed textile material was then after-treated for minutes at 50C in a winch vat. first with an aqueous bath containing 1 g/l of an anionic detergent of the type of oleylmethyltaurine and then with a cold aqueous rinsing bath.
  • a chromium complex compound of the dyestuff coupled product of diazotized 2-aminophenol-5-sulfonic acid dimethylamide with 3-methyl-5-hydroxy-pyrazol chromium complex
  • the yarns showed a yellow dyeing the properties of fastness of which did not differ from the properties of an analagous dyeing from an aqueous medium.
  • the dyestuff is a disperse dyestuff or a water-insoluble organic pigment dyestuff.
  • the dyestuff is a water-soluble anionic or non-ionic dispersed metal complex dyestuff.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
US329680A 1972-02-08 1973-02-05 Dyeing synthetic and natural fibers with the liquid ammonia and chloroform or methylene chloride solution of a dye Expired - Lifetime US3876370A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19722205813 DE2205813B2 (de) 1972-02-08 1972-02-08 Verfahren zum faerben synthetischer und natuerlicher fasern unter verwendung von fluessigem ammoniak als behandlungsmittel

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US (1) US3876370A (de)
JP (1) JPS4891382A (de)
BE (1) BE795145A (de)
DE (1) DE2205813B2 (de)
FR (1) FR2171301A1 (de)
IT (1) IT978850B (de)
NL (1) NL7301522A (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4074969A (en) * 1974-07-19 1978-02-21 Cluett, Peabody & Co., Inc. Process for recovery and reuse of ammonia in a liquid ammonia fabric treating system
US4121899A (en) * 1977-03-04 1978-10-24 Milliken Research Corporation Condensation dyeing
CN103225218A (zh) * 2013-04-10 2013-07-31 武汉纺织大学 一种纤维素纤维的液氨染色方法
WO2015186115A1 (en) * 2014-06-06 2015-12-10 Reggiani Macchine S.P.A. Method for dyeing and finishing textile material and corresponding apparatus
US11591748B2 (en) 2020-01-14 2023-02-28 Shadow Works, Llc Heat treated multilayer knitted textile of liquid crystal polymer fibers and modified polyacrylonitrile fibers, and process for making same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH627775A5 (de) * 1977-02-03 1982-01-29 Ciba Geigy Ag Verfahren zur umwandlung eines pigments oder dispersionsfarbstoffs in eine andere modifikation.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666398A (en) * 1971-02-01 1972-05-30 Joseph P Tratnyek Method of dyeing shaped organic materials from liquid ammonia dye baths
US3802835A (en) * 1972-08-03 1974-04-09 North American Mills Alcohol-ammonia dye solution and dyeing therewith

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666398A (en) * 1971-02-01 1972-05-30 Joseph P Tratnyek Method of dyeing shaped organic materials from liquid ammonia dye baths
US3802835A (en) * 1972-08-03 1974-04-09 North American Mills Alcohol-ammonia dye solution and dyeing therewith

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4074969A (en) * 1974-07-19 1978-02-21 Cluett, Peabody & Co., Inc. Process for recovery and reuse of ammonia in a liquid ammonia fabric treating system
US4121899A (en) * 1977-03-04 1978-10-24 Milliken Research Corporation Condensation dyeing
CN103225218A (zh) * 2013-04-10 2013-07-31 武汉纺织大学 一种纤维素纤维的液氨染色方法
CN103225218B (zh) * 2013-04-10 2016-04-20 武汉纺织大学 一种纤维素纤维的液氨染色方法
WO2015186115A1 (en) * 2014-06-06 2015-12-10 Reggiani Macchine S.P.A. Method for dyeing and finishing textile material and corresponding apparatus
CN106460310A (zh) * 2014-06-06 2017-02-22 雷贾尼机械股份公司 用于对纺织材料染色和整理的方法和对应装置
CN106460310B (zh) * 2014-06-06 2019-05-10 雷贾尼机械股份公司 用于对纺织材料染色和整理的方法和对应装置
US11591748B2 (en) 2020-01-14 2023-02-28 Shadow Works, Llc Heat treated multilayer knitted textile of liquid crystal polymer fibers and modified polyacrylonitrile fibers, and process for making same

Also Published As

Publication number Publication date
DE2205813B2 (de) 1978-02-23
JPS4891382A (de) 1973-11-28
DE2205813A1 (de) 1973-08-30
IT978850B (it) 1974-09-20
NL7301522A (de) 1973-08-10
BE795145A (fr) 1973-08-08
FR2171301A1 (de) 1973-09-21

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