US3294476A - Sulfur dye compositions and method of dyeing textile materials therewith - Google Patents

Sulfur dye compositions and method of dyeing textile materials therewith Download PDF

Info

Publication number
US3294476A
US3294476A US413959A US41395964A US3294476A US 3294476 A US3294476 A US 3294476A US 413959 A US413959 A US 413959A US 41395964 A US41395964 A US 41395964A US 3294476 A US3294476 A US 3294476A
Authority
US
United States
Prior art keywords
litre
dyeing
textile materials
dried
sulfur
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US413959A
Other languages
English (en)
Inventor
Krusche Erwin
Heid Christian
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Application granted granted Critical
Publication of US3294476A publication Critical patent/US3294476A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • D06P3/605Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre
    • 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
    • D06P1/30General 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 sulfur dyes
    • D06P1/305SO3H-groups containing 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
    • 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
    • D06P3/605Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre
    • D06P3/6066Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre by using reactive polyfunctional compounds, e.g. crosslinkers

Definitions

  • This invention relates to dye compositions and methods and more particularly to dye compositions comprising as the principal constituents, thiosul-fonic acids of sulfur dyestuffs in the form of their water-soluble salts and a bior poly-functional chemical substance capable of reacting by cross-linking with the thiosulfonic acids of the sulfur dyestuffs to give stable reaction products.
  • the dyestuff compositions and methods of the present invention have overcome the above mentioned prior art disadvantages, have markedly simplified the procedure and provided efiicient dyeing of the textile material with good dry and wet fastness properties.
  • bior polyfunctional chemical compounds which may be used as cross-linking agents with the thiosulfonic acids of sulfur dyestuffs in accordance with this invention are as follows:
  • Dior poly-epoxides or -chlorohydrines the tris-acryloyl-hexahydro-1,3,5-s-triazine of the formula O(
  • the textile material to be treated in accordance with this invention may be in any of the usual forms, such as fibers, yarns, and woven or knitted fabrics.
  • the basic fiber of this material may be any of the presently known cellulosic textile fibers, e.g. cotton, rayon, linen. It is surprising that, when mixed fabrics consisting of a portion of cellulosic material and a portion of a synthetic fiber are dyed according to the invention, the synthetic portion is also dyed, which was not possible heretofore with the known processes.
  • the abovementioned simplified and substantially less expensive .process of the present invention avoids the usual necessity of reducing the dyestuff with alkaline sulfides, such as sodium sulfide or sodium hydrogensulfide. Instead, the present process uses thiosulfonic acids of sulfur dyestuffs in the form of their water-soluble salts in unreduced state and .provides, for the first time, efficient dyeing of said textile materials therewith in a simpler manner and without the concurrent use of reducing agents.
  • EXAMPLE 1 A cotton fabric is impregnated with a solution containing 50 g./ litre Hydrosol Fastgreen 3 B (Color Index: Solubilized Sulfur Green 2, CI No. 53572), 20 -g./lit-re ethylene-glycol-bis-glycide ether and 5 g./ litre calcined sodium carbonate, it is dried at 80 C. and then subjected to a dry heat treatment for 1 minute at 150 C.; subsequently the fabric is rinsed, oxidized in a liquor ratio of 1:20 for 10 minutes at -80 C.
  • Hydrosol Fastgreen 3 B Color Index: Solubilized Sulfur Green 2, CI No. 53572
  • 20 -g./lit-re ethylene-glycol-bis-glycide ether 20 -g./lit-re ethylene-glycol-bis-glycide ether and 5 g./ litre calcined sodium carbonate
  • EXAMPLE 2 A mixed cotton-polyester fabric is impregnated with a solution containing 40 ig./litre Hydrosol Fast-katechu RL (Color Index: Solubilized Sulfur Brown 52 Cl No. 5 3321), 30 g./'litre of a 65% solution of methyl-etherified trimet-hyl-ol melamine, and 10 g./ litre ammonium chloride, it is dried at C., and then subjected to a dry heat treatment for 1 minute at 220 C. The fabric is then rinsed and dried. The dyeing shows good fastness to washing and to light.
  • Hydrosol Fast-katechu RL Color Index: Solubilized Sulfur Brown 52 Cl No. 5 3321
  • 30 g./'litre of a 65% solution of methyl-etherified trimet-hyl-ol melamine 10 g./ litre ammonium chloride
  • EXAMPLE 3 A cotton fabric is impregnated with a solution containing 50 g./litre Hydrosol Fastyellow G (a thiosulfonic acid sulfur dyestuff) (Color Index: Solubilized Sulfur Yellow '5), 40 g./litre tris-acryloyl-hexahydro-l,3,5-s-triazine, and 10 g./litre calcined sodium carbonate, it is then dried at C. and steamed for 1 minute at C. Subsequently, the fabric is rinsed, oxidized with bichromate-coppersulfate-acetic acid as indicated in Example l, rinsed again, and finished. The dyeing thus obtained shows good wet fastness properties.
  • Hydrosol Fastyellow G a thiosulfonic acid sulfur dyestuff
  • EXAMPLE 4 A cotton fabric is impregnated with a solution containing 40 g./litre Hydrosol Fast-katechu RL (Color In dex: Solubilized Sulfur Brown 52, CI No. 53321), 10 g./ litre ammonium chloride, and 30 g./litre tris-(aziridinyl)-phosphinoxide, it is dried at 100 C. and then subjected to a dryheat treatment for 1 minute at 200 C. The fabric is then rinsed, oxidized with bichromate-cop persulfate-acetic acid as indicated in Example 1, rinsed again, and dried. The dyeing shows a good fastness to washing and to washing with peroxide.
  • Hydrosol Fast-katechu RL Color In dex: Solubilized Sulfur Brown 52, CI No. 53321
  • 10 g./ litre ammonium chloride 10 g./ litre ammonium chloride
  • EXAMPLE 5 A cotton fabric is impregnated with a solution containing 30 g./litre Hydrosol Fast-khaki AL (a thiosul' fonic acid sulfur dyestuff) (Color Index: Solubilized Sulfur Green 19), g./litre calcined sodium carbonate, and 20 g./litre of the tris-chloroacetyl compound of the diethylene-triamine, it is dried at 100 C., and subjected to a dryheat treatment for 1 minute at 200 C. The fabric is then rinsed and dried. The dyeing shows a very good fastness to washing and to washing with peroxide.
  • Hydrosol Fast-khaki AL a thiosul' fonic acid sulfur dyestuff
  • EXAMPLE 6 A cotton fabric is impregnated with a solution containing 50 g./litre Hydrosol Fast-olive BBN N(Color Index: Solubilized Sulfur Green 9, CI No. 53006), 30 g./litre of a 65% solution of methyl-etherified tri-methylol-melamine, and 10 g./litre ammonium chloride, it is dried at 100 C., and then subjected to a dry heat treatment for 1 minute at 220 C.
  • the fabric is rinsed and dried.
  • the dyeing shows good fastness to washing and light.
  • the fixation of the dyestuff can also be obtained with the same success, when in this example the impregnated and dried cotton fabric is steamed for 60 seconds at 105 C. instead of submitted to the dryheat treatment.
  • EXAMPLE 7 A mixed cotton-polyacrylonitrile fabric is impregnated with a solution containing 40 g./litre Hydrosol Fast-katechu RL (Color Index: Solubilized Sulfur Brown 52, CI
  • EXAMPLE 8 A cotton fabric is impregnated with a solution containing 40 g./litre Hydrosol Fastbrown BT (Color Index: Solubilized Sulfur Brown 16, CI No. 53286), 50 g./ litre ethylene-bis-(2-hydroxy-3-chloro-l-propyl -ether and 20 g./litre calcined sodium carbonate, it is dried at C. and subjected to a dry heat treatment for 1 minute at 220 C. Subsequently, the fabric is rinsed and dried. The dyeing shows a good fastness to washing and to washing with peroxide.
  • a water-soluble, unreduced dyestuff composition for dyeing textile materials comprising as the principal constituents, water-soluble salts of thiosulfonic acids of sulfur dyestuffs and a polyfunctional cross-linking agent, which constituents react with each other at elevated temperatures to give stable reaction products and enable the dyeing of said textile materials without the use of alkali reducing agents.
  • a method of dyeing textile materials comprising impregnating the textile material with an aqueous solution of salts of thiosulfonic acids of sulfur dyestuffs, and a polyfunctional cross-linking agent, drying the impregnated material and subjecting the dried material to an elevated temperature for a relatively short period of time sufficient to effect reaction between the polyfunctional cross-linking agent and the dyestuff.
  • the polyfunctional cross-linking agent is an etherified polymethylol melamine resin which provides a resin finish on the cloth in addition to reacting with the dyestuff to effect the dyeing of the textile material.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Structural Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US413959A 1963-11-27 1964-11-25 Sulfur dye compositions and method of dyeing textile materials therewith Expired - Lifetime US3294476A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC0031521 1963-11-27

Publications (1)

Publication Number Publication Date
US3294476A true US3294476A (en) 1966-12-27

Family

ID=7019859

Family Applications (1)

Application Number Title Priority Date Filing Date
US413959A Expired - Lifetime US3294476A (en) 1963-11-27 1964-11-25 Sulfur dye compositions and method of dyeing textile materials therewith

Country Status (6)

Country Link
US (1) US3294476A (de)
BE (1) BE656363A (de)
CH (1) CH423711A (de)
DE (1) DE1444219A1 (de)
GB (1) GB1034606A (de)
NL (1) NL6413327A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120647A (en) * 1976-06-04 1978-10-17 Ciba-Geigy Corporation Process for the dyeing of wool-containing fibre materials

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1418196A (fr) * 1964-10-06 1965-11-19 Kuhlmann Ets Nouveaux colorants, leurs procédés de préparation et leurs applications
US6245117B1 (en) 1998-08-07 2001-06-12 Ipposha Oil Industries Co., Ltd. Modifier of cellulose fibers and modification method of cellulose fibers

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR784692A (fr) * 1933-12-22 1935-07-22 Calico Printers Ass Ltd Procédé pour améliorer la fixation de colorants sur des fibres textiles
DE907643C (de) * 1951-07-14 1954-03-29 Hermann Rath Dipl Chem Dr Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen und Drucken mitSchwefelfarbstoffen
DE952619C (de) * 1952-12-28 1956-11-22 Hermann Rath Dipl Chem Dr Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen und Drucken mit Schwefelfarbstoffen
DE1004586B (de) * 1954-12-29 1957-03-21 Cassella Farbwerke Mainkur Ag Verfahren zum Faerben von Baumwolle und Regeneratcellulose mit Schwefelfarbstoffen ohne Anwendung von Reduktionsmitteln
DE1151241B (de) * 1962-04-04 1963-07-11 Cassella Farbwerke Mainkur Ag Verfahren zur Verbesserung der Echtheits-eigenschaften von mit Schwefelfarbstoffen erzeugten Faerbungen und Drucken

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR784692A (fr) * 1933-12-22 1935-07-22 Calico Printers Ass Ltd Procédé pour améliorer la fixation de colorants sur des fibres textiles
DE907643C (de) * 1951-07-14 1954-03-29 Hermann Rath Dipl Chem Dr Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen und Drucken mitSchwefelfarbstoffen
DE952619C (de) * 1952-12-28 1956-11-22 Hermann Rath Dipl Chem Dr Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen und Drucken mit Schwefelfarbstoffen
DE1004586B (de) * 1954-12-29 1957-03-21 Cassella Farbwerke Mainkur Ag Verfahren zum Faerben von Baumwolle und Regeneratcellulose mit Schwefelfarbstoffen ohne Anwendung von Reduktionsmitteln
DE1151241B (de) * 1962-04-04 1963-07-11 Cassella Farbwerke Mainkur Ag Verfahren zur Verbesserung der Echtheits-eigenschaften von mit Schwefelfarbstoffen erzeugten Faerbungen und Drucken

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120647A (en) * 1976-06-04 1978-10-17 Ciba-Geigy Corporation Process for the dyeing of wool-containing fibre materials

Also Published As

Publication number Publication date
GB1034606A (en) 1966-06-29
BE656363A (de) 1965-03-16
NL6413327A (de) 1965-05-28
DE1444219A1 (de) 1968-10-24
CH423711A (de) 1966-07-29

Similar Documents

Publication Publication Date Title
US4455147A (en) Transfer printing
DE3709766A1 (de) Verfahren zum alkali-freien faerben mit reaktivfarbstoffen
US2364726A (en) Process for improving the dyeings and prings prepared with watersoluble dyestuffs
US4313732A (en) Process for improving washfastness of indigo-dyed fabrics
US3049446A (en) Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials
US4704132A (en) After-treatment of dyeings with reactive dyes on cellulose fiber materials
US3666398A (en) Method of dyeing shaped organic materials from liquid ammonia dye baths
US4950301A (en) Keratinous textile treatment with arylating compounds containing fibre reactive groups
US2726133A (en) Effect threads
US3679348A (en) Combined process for dyeing and finishing fabrics composed of cellulosic fibers
US3294476A (en) Sulfur dye compositions and method of dyeing textile materials therewith
US4304566A (en) Process for the dyeing of wool with reactive dyestuffs
US2203493A (en) Treatment of cellulosic material
JPS58156088A (ja) 紡織ウエブの連続的染色法
GB445774A (en) Improvements in the treatment of textile fabrics
US2121337A (en) Dyeing mixed fibers
US4289496A (en) Finishing process
US2426861A (en) Process for improving the properties of water-insoluble artificial protein fibres
US2234905A (en) Dyeing of cellulosic textile
US2322333A (en) Improving fastness of dyeings
EP0286597B1 (de) Färben und Bedrucken von Fasern
US3533728A (en) Inorganic and/or organic cellulose swelling agents used in conjunction with cross-linking agents in fabric modification process
US3411860A (en) Method of dyeing cellulose fibers
US3873265A (en) Vat or reactive dyes or mixtures thereof and acrylamide or methylene bis acrylamide in alkaline crosslinking and dyeing
US3054699A (en) Water-soluble latent curing catalysts for textile treatment resins