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

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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
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litre
dyeing
textile materials
dried
sulfur
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Krusche Erwin
Heid Christian
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Cassella Farbwerke Mainkur 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/605—Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre
    • 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
    • D06P1/30—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 sulfur dyes
    • D06P1/305—SO3H-groups containing dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/605—Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre
    • D06P3/6066—Natural 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.

Description

United States Patent 3 2% 476 surrun DYE coMrdsirioNs AND METHQD or DYEENG TEXTILE MATERTALS THEREWTTH Erwin Krusche and Christian Haiti, Frankfurt am Main- Fechenheirn, Germany, assignors to Cassella Far-bwerlre Mainkur Aktiengesellschaft, Frankfurt am Main- Fechenheim, Germany, a German company No Drawing. Filed Nov. 25, 1964, Ser. No. 413,959
Claims priority, application Germany, Nov. 27, 1963,
31,521 6 Claims. (Cl. 8-37) 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.
These dye compositions enable the use of a much simpler and less expensive method of application of such dyestuffs to textile materials.
It has been usual heretofore to dye textile materials with the thiosulfonic acids of sulfur dyestuffs but these prior procedures had the disadvantage of requiring the use of alkaline chemicals to effect reduction of the dyestuif with transformation of the thiosulfonic acid of the dyestuff into the substantive leuco compound of the sulfur dye which forms uneven dyeings as a result of its substantive character. Furthermore, the prior processes required a two-step process or method to complete the dyeing operation.
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.
Illustrative but nonlimiting examples of the 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(|3CH=CH2 In? (Inn H2C=HC.OC-N NOO.CH=CH2 the bis-B-hydroxyethylsulfone of the formula ornornou CIHLCEZ-OH the dithrough hexamethylol compounds of melamine, the dimethylol derivatives of urea, ethylene urea, and s-triazone or the alkyl ethers thereof, the di-sodium salt of the tris-(fi-sulfato-hydroxyethyl)-sulfonium betaine of the formula CHZ.CH2.O.SO3-
' SCH2.CH2.O.SO Ntl CHz.CHg.O.SO Na the bisor poly-chloroacetyl compounds of dior polyamines, the tris-aziridinyl-phosphinoxyde of the formula and the dior poly-isocyanates or their bisulfite addition compounds.
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. Likewise, 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.
This is made possible by reacting the thiosulfonic acids of sulfur dyestuffs with a bior polyfunctional compound, such as above mentioned preferably in the presence of a catalyst, in place, on the textile material to be dyed, followed by a probable drying of the treated goods at controlled elevated temperatures and then heating of the treated material at substantially higher temperatures for a short period of time to bring about the reaction between the dyestuff and the bior polyfunctional compound. This sets the dye on the textile material in a stable uniform manner and may give a resin finish on the material where the bior polyfunctional com-pound used is a resin with inherent txetile finishing properties. Illustrative examples for carrying out the process of the present invention in accordance with the above described principles and general procedures, are as follows:
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. with a solution of 1 g./litre bichromate, 1 'g./litre copper sulfate, and 2 cc./litre 60% acetic acid, and then finished by rinsing and drying. The dyeing thus obtained shows very good wet fastness properties, in particular a good fastness to washing with peroxide.
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.
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.
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.
A similarly favorable result is obtained by steaming the cotton fabric impregnated and dried according to this example for 40 seconds at 105 C. instead of subjecting same to the dryheat treatment.
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.
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.
Subsequently, 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
No. 53321), 10 g./litre ammonium chloride, and 40 g./ litre methyletherified trimethylol-melamine, it is dried at 80 C. and subjected to a dry heat treatment for l min ute at 200 C. Subsequently, the fabric is rinsed and dried. The dyeing shows a good fastness to washing.
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.
What is claimed is:
1. 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.
2. A water-soluble, unreduced dyestuff composition as defined in claim 1 wherein the polyfunctional cross-linking agent is a resin and provides a resin finish on the treated textile material.
3. A water-soluble, unreduced dyestuff composition as defined in claim 1 in which the polyfunctional cross-linking agent is a member of the group consisting of diepoxydes, poly-epoxydes, di-chlorohydrines, poly-chlorohydrines, tris-acryloyl-hexahydro-1,3,5-s-triazine, bis-fi-hydroxy-ethylsulfone, poly-methylol melamine, dimethylol derivatives of urea, ethylene urea, and s-triazone, alkyl ethers of methylol compounds, tris-(fl-sulfato-hydroxyethyl)-sulfonium betaine, poly-chloroacetyl compounds of polyamines, tris-aziridinyl-phosphinoxide and polyisocyanates.
4. 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.
5. A method of dyeing textile materials as defined in claim 4, and in which the impregnated textile material is dried at a temperature not substantially exceeding 80 C. and the dried material heated to temperatures of approximately between C. and 200 C. for a few minutes to effect said reaction between the polyfunctional cross-linking agent and the dyestuff.
6. A method of dyeing textile materials as defined in claim 4, and in which 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.
References Cited by the Examiner FOREIGN PATENTS 784,692 7/1935 France.
907,643 3/1954 Germany.
952,619 11/1956 Germany. 1,004,586 3/1957 Germany. 1,151,241 7/1963 Germany.
NORMAN G. TORCHIN, Primary Examiner.
J. HERBERT, Assistant Examiner.

Claims (1)

1. 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.
US413959A 1963-11-27 1964-11-25 Sulfur dye compositions and method of dyeing textile materials therewith Expired - Lifetime US3294476A (en)

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BE (1) BE656363A (en)
CH (1) CH423711A (en)
DE (1) DE1444219A1 (en)
GB (1) GB1034606A (en)
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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 (en) * 1964-10-06 1965-11-19 Kuhlmann Ets New dyes, their preparation processes and their 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 (en) * 1933-12-22 1935-07-22 Calico Printers Ass Ltd Process for improving the fixation of dyes on textile fibers
DE907643C (en) * 1951-07-14 1954-03-29 Hermann Rath Dipl Chem Dr Process for improving the fastness properties of dyeings and prints with sulfur dyes
DE952619C (en) * 1952-12-28 1956-11-22 Hermann Rath Dipl Chem Dr Process for improving the fastness properties of dyeings and prints with sulfur dyes
DE1004586B (en) * 1954-12-29 1957-03-21 Cassella Farbwerke Mainkur Ag Process for dyeing cotton and regenerated cellulose with sulfur dyes without the use of reducing agents
DE1151241B (en) * 1962-04-04 1963-07-11 Cassella Farbwerke Mainkur Ag Process for improving the fastness properties of dyeings and prints produced with sulfur dyes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR784692A (en) * 1933-12-22 1935-07-22 Calico Printers Ass Ltd Process for improving the fixation of dyes on textile fibers
DE907643C (en) * 1951-07-14 1954-03-29 Hermann Rath Dipl Chem Dr Process for improving the fastness properties of dyeings and prints with sulfur dyes
DE952619C (en) * 1952-12-28 1956-11-22 Hermann Rath Dipl Chem Dr Process for improving the fastness properties of dyeings and prints with sulfur dyes
DE1004586B (en) * 1954-12-29 1957-03-21 Cassella Farbwerke Mainkur Ag Process for dyeing cotton and regenerated cellulose with sulfur dyes without the use of reducing agents
DE1151241B (en) * 1962-04-04 1963-07-11 Cassella Farbwerke Mainkur Ag Process for improving the fastness properties of dyeings and prints produced with sulfur dyes

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

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DE1444219A1 (en) 1968-10-24
GB1034606A (en) 1966-06-29
BE656363A (en) 1965-03-16
CH423711A (en) 1966-07-29

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