US3264053A - Process for dyeing textile fibers with azo-disulfide and sulfur dyestuffs and dyed products thereof - Google Patents

Process for dyeing textile fibers with azo-disulfide and sulfur dyestuffs and dyed products thereof Download PDF

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US3264053A
US3264053A US264413A US26441363A US3264053A US 3264053 A US3264053 A US 3264053A US 264413 A US264413 A US 264413A US 26441363 A US26441363 A US 26441363A US 3264053 A US3264053 A US 3264053A
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Prior art keywords
azo
disulfide
fibers
dyestuff
dye
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US264413A
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English (en)
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Charles R Holtzclaw
James H Benson
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Martin Marietta Corp
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Martin Marietta Corp
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Priority to US264044A priority Critical patent/US3329477A/en
Priority to US264413A priority patent/US3264053A/en
Priority to US264045A priority patent/US3225025A/en
Priority to US307014A priority patent/US3299040A/en
Priority to NL6402181A priority patent/NL6402181A/xx
Priority to NL6402179A priority patent/NL6402179A/xx
Priority to NL6402178A priority patent/NL6402178A/xx
Priority to NL6402184A priority patent/NL6402184A/xx
Priority to NL6402183A priority patent/NL6402183A/xx
Priority to NL6402180A priority patent/NL6402180A/xx
Priority to BE644979D priority patent/BE644979A/xx
Priority to BE644982D priority patent/BE644982A/xx
Priority to GB10157/64A priority patent/GB1016850A/en
Priority to GB10159/64A priority patent/GB1025043A/en
Priority to BE644984D priority patent/BE644984A/xx
Priority to BE644985D priority patent/BE644985A/xx
Priority to GB10155/64A priority patent/GB1020706A/en
Priority to GB10160/64A priority patent/GB1018459A/en
Priority to BE644980D priority patent/BE644980A/xx
Priority to GB10154/64A priority patent/GB1016085A/en
Priority to ES0297453A priority patent/ES297453A1/es
Priority to GB10156/64A priority patent/GB1014703A/en
Priority to BE644983D priority patent/BE644983A/xx
Application granted granted Critical
Publication of US3264053A publication Critical patent/US3264053A/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B49/00—Sulfur dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/227—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl sulfide or a diaryl polysulfide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B3/00—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating
    • D06B3/10—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fabrics
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B2700/00—Treating of textile materials, e.g. bleaching, dyeing, mercerising, impregnating, washing; Fulling of fabrics
    • D06B2700/09—Apparatus for passing open width fabrics through bleaching, washing or dyeing liquid
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/01—Mixtures of azo compounds
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to a method for dyeing textile fibers, and more particularly to an improved method for dyeing textile fibers with a dyestuff selected from the group consisting of azo-disulfide dyestuff and mixture of azo-disulfide dyestufi" and sulfur dye.
  • the present invention also relates to textile fibers dyed with a combination of azo-disulfide dyestuff and sulfur dye.
  • the method of the present invention is particularly characterized in that it provides for the first time a commercially acceptable method for dyeing textile fibers with azo-disulfide dyestuif pigments.
  • the method is further characterized in that higher color yield and improved levelness of appearance (uniformity of dyeing) are provided over that obtainable by prior methods for dyeing with azo-disulfide dyestuffs.
  • azo-disulfide dyestufifs which are reducible, poorly reducible and nonreducible in reducing agents at the normal temperature of reducing baths, e.g., about room temperature to about 160 B, may be used to dye textile fibers according to the method of the present invention.
  • the present method is further characterized in that it comprises the first known method for dyeing textile fibers with azo-disulfide dyestuffs which are non-reducible in reducing baths at normal temperatures.
  • textile fibers may be dyed with a dye composition comprising a mixture of azo-disulfide dyestuif and sulfur dye.
  • a dye composition comprising a mixture of azo-disulfide dyestuif and sulfur dye.
  • the method of the present invention is a method for dyeing textile fibers comprising the steps of padding onto the fibers an aqueous dye composition comprising azo-disulfide dyestuff pigment, reducing the dyestuff, oxidizing the dyestulf, scouring and drying the fibers.
  • the reducing agent may be applied with the dyestuif or separately and prior to steaming the fibers.
  • the method of the present invention may be carried out by one of the following processes comprising the following steps:
  • a dye composition comprising reducing agent, water, and dyestuif selected from the group consisting of non-reduced azo-disulfide dyestuff pigment and non-reduced azo-disulfide dyestuff pigment plus reduced sulfur dye, steaming the fibers, option- 3,2fi4,053- Patented August 2, 1966 ally washing the fibers, oxidizing the dyestuif, scouring and drying the fibers;
  • a dye composition comprising water, non-reduced azo-disulfide dyestuif pigment and reduced sulfur dye, drying the fibers, applying reducing agent to the fibers, steaming the fibers, optionally washing the fibers, oxidizing the dyestuff, scouring and drying the fibers;
  • a dye composition comprising water, alkali, delayed act-ion reducing agent, and dyestutf selected from the group consisting of non-reduced azo-disulfide dyestuff pigment and non-reduced azo-disulfide dyestuif pigment plus non-reduced sulfur dye, drying the fibers, steaming the fibers to reduce the dyestuflf, optionally washing the fibers, oxidizing the dyestuff, scouring and drying the fibers;
  • aqueous dye composition comprising non-reduced azo-disulfide dyestuif pigment and dissolved non-reduced sulfur dye, drying the fibers, applying reducing agent to the fibers, steaming the fibers, optionally washing the fibers, oxidizing the dyestuff, scouring and drying the fibers;
  • the azo groups may either be connected to the same aromati nuclei to which the disulfide group is connected, or they may be found elsewhere in the color bodies.
  • Illustrative examples of the above three types of azo-disulfide dyestuffs are the dyestuff formed by coupling one mole of diazotized S-thiocyano-Z-amino-toluene to one mole of beta-naphtha], which dyestuff upon reduction and subsequent oxidation produces 3:3 dimethyldiphenyldisulfide 4:4 bis (azo beta naphthol); the dyestuff formed by coupling one mole of diazotized para-nitroaniline to one mole of 1 phenyl 3 methyl 5 pyrazolone, reducing and diazotizing the resulting product and coupling it to one-half mole of beta-hydroxynaphthoic acid dithioanilide; and the dyestuff formed by coupling one mole of tetrazotized 4:4 diaminodiphenyldisulfide to two moles of 1-phenyl-3-methyl-5-pyrazoline.
  • Certain azo-disulfide dyestuffs have been known for more than fifty years, but the azo-disulfide dyestuffs prepared by coupling a mole of tetrazotized diaminodiphenyldisulfide with two moles of an azo coupling component have never gone into commercial production or use, primarily because there has remained unknown a useful commercial method for applying the dyestuffs to textile fibers in which the resulting dyeings have commercially acceptable color yield.
  • color yield refers to the depth of shade obtained from a given amount of dyestuff.
  • the difiiculties with the exhaustion method in the dyeing of azo-disulfide dyestuffs are that those azodisulfide dyestuffs which are non-reducible at the normal temperatures of dye baths cannot be applied by the exhaustion method; those azo-disulfide dyestuffs which are poorly reducible at the normal temperatures of dye baths cannot be applied satisfactorily by the exhaustion method; and only those azo-disulfide dyestuffs which are reducible or converted into their soluble state at the normal temperatures of dye baths may be applied to textile fibers, and even in connection with these azo-disulfide dyestuffs the exhaustion method is not commercially acceptable because the exhaustion technique depends on long or repeated immersion of textile fibers into the reduced dyebath and upon the physical afiinity of the dyestutf for the fibers, and inasmuch as azo-disulfide dyestuffs have poor affinity for textile fiber
  • the exhaustion method is commercially unsuitable for dyeing azo-d-isulfide dyestuffs because it is limited to dyeing those azo-disulfide dyes which are soluble at the normal temperatures of reducing baths, it requires too much time, it provides poor color yield, and the dye is not fixed firmly on the fibers.
  • US. Patent No. 3,088,790 discloses useful methods for dyeing azo dyes having pendant thiosulfate groups attached via bridging members to aryl groups of the dyestulf.
  • those azo-disulfide dyes prepared by coupling a mole of tetrazotized diaminodiphenyldisulfide with two moles of azo coupling component may not be dyed satisfactorily by this method.
  • a high speed, continuous, economical method for dyeing textile fibers with azo-disulfide dyestuffs has been developed.
  • the primary advantages of the method are that high color yield and improved levelness of appearance are obtained.
  • a method has been provided for the first time whereby all of the azo-disulfide dyestuffs may be applied to textile fibers, e.g., those which are reducible, poorly reducible, and non-reducible in reducing baths at normal temperatures.
  • azo-disulfide dyestuffs which are not reduced in the dye composition should be utilized; in the case of the delayed action reducing agents, this is not applicable because they do not reduce the dye in the dye composition, and until reaching the steamer. In each of the above instances, the azo-disulfide dyestuff pigment is reduced in the steamer.
  • the amount of dyestuff utilized in the dye composition will vary with the depth of shade desired, higher concentrations being required to obtain deeper shades than to obtain lighter shades. Generally speaking, about 2 oz. by weight of concentrated dyestuff per gallon of dye composition is suitable to provide a medium shade, and from about 0.2 oz. to 8 oz. of concentrated dyestuff per gallon of dye composition will provide a wide range of depth or shade.
  • the dye composition may be advantageously applied to the fibers by passing them through a pad box containing the dye composition.
  • the temperature of the dye composition may be maintained from about room temperature to about 170 F., and prefer-ably within the range of about l50 F.
  • the steps subsequent to padding comprise drying, applying reducing agent, steaming, optional washing, oxidizing, scouring and drying.
  • the steps subsequent to padding comprise steaming, optional washing, oxidizing, scouring and drying. Also, these may be dried subsequent to padding on the dye composition, provided either that a delayed action reducing agent is used as the reducing agent, or that additional reducing agent is applied subsequent to drying and prior to steaming.
  • the drying prior to steaming improves the levelness of appearance of the resulting dyemg.
  • the reducing agent may be any of the conventional reducing agents, such as sodium sulphide, sodium polysulphide, sodium sulfhydrate, mixtures thereof, etc., although sodium sulphide is preferred for reasons of economy; or, alkali and one of the delayed action reducing agents, such as thiorurea, sodium s-sodiocarboxy methyl thiosulfate,
  • the amount of reducing agent needed will be determined by the particular dyestuif being applied, the amount of dyestuif, and the capacity of the reducing agent selected for hydrogen donation. Since the use of reducing agents is well understood in the dyeing art, it will suffice to say that enough reducing agent is utilized to effect reduction of the dyestulf. When 2 oz. of concentrated dyestuif per gallon of dye composition is utilized, about 6 oz. of sodium sulphide will effect the reduction. Generally speaking, about 2-10 oz. of reducing agent per gallon of water will be satisfactory.
  • the reducing agent When the reducing agent is applied to the fibers from a separate bath, it may be maintained at from about room temperature to 190 F., and preferably at about 130160 F.
  • the steaming completes the reduction of the dyestulf by the reducing agent. Steaming the fibers for about one-half to five minutes at about 212 F.-225 F. is satisfactory to complete the reduction; about one-half to one minute is suggested when the conventional inorganic reducing agents are used and about two minutes When the delayed action reducing agents are used. Also, it is suggested that the steaming be done with neutral air-free steam.
  • the fibers are preferably washed with water and then passed through an acid-oxidizing bath, although the washing step may be omitted and the oxidizing bath may be neutral or alkaline.
  • the washing step is suggested to remove excess reducing solution and other extraneous materials, and to prevent dilution of the subsequent oxidizing bath.
  • the excess reducing agent reacts with the acid and hydrogen sulfide gas is generated; production of hydrogen sulfide gas may be avoided by either using a neutral or alkaline oxidizing bath or by washing the fibers prior to passing them into the acid; however, if the fibers are to pass from the steamer into an :acidic solution, it is suggested that the acidic bath be covered with a hood and that the hydrogen sulfide gas be carried away by means of a connecting duct and exhaust fan.
  • the fibers may be steamed and then (a) washed and passed through an oxidizing agent, or (b) passed through acid, Washed, and passed through an oxidizing agent, or (c) passed through an oxidizing bath.
  • neutral or alkaline oxidizing baths may be used, it is preferred to use an acid-oxidizing bath, as the acid assists in increasing the color yield and as the acidoxidizing bath provides substantially more color yield than acidifying, washing and oxidizing in separate steps.
  • the amount of oxidizing agent required will depend on the particular dyestuif selected, the amount of dyestuif selected, the amount and type of'reducing agent previously employed, whether the fibers have been washed prior to oxidizing, and on the capacity of the particular oxidizing agent for'oxygen donation. Inasmuch as the use of oxidizing agents is well understood in the dyeing art, it will suifice to state that enough oxidizing agent is utilized to oxidize the dyestuff. When 2 oz. of concentrated dyestulf per gallon is reduced by oz. of sodium sulphide per gallon and the fibers are subsequently washed, 1 oz. of glacial acetic acid and 1 oz. of sodium bichromate per gallon will make the corresponding oxidation. Generally speaking, about 0.5-2 oz. of oxidizing agent per gallon of water and enough acid to bring the pH to 4-6 is suitable.
  • the fibers are scoured and dried.
  • the drying may be efiected in any continuous manner, such as housed tenter frame, heated cans, or loop dryer.
  • the chemistry of the dyeing reaction is believed to be as follows.
  • the azo-disulfide dye contains a di- 6 sulfide linkage, R SSR which is considered to be the oxidized state
  • the dyestufi is reduced to form its normal reduced state.
  • the oxidizing agent restores the dyestufi to its oxidized state, firmly fixed upon the fibers.
  • the reducing agent converts R QSX and R fiSX, wherein X may be such as a cyano or sulfonic group, to R -S-Na and R SNa, and the oxidizing agent oxidizes them into R fiSSR firmly fixed upon the fiber.
  • Textile fibers that may be dyed according to the invention include cotton, nylon and regenerated cellulose.
  • FIG. la is a diagrammatic view, broken away, showing a portion of the apparatus.
  • FIG. 1b is a diagrammatic view, broken away, showing a continuation of the apparatus of FIG. 1a.
  • Example 1 Referring now to FIGS. 1a and lb for a better understanding of the present invention, conventional prebleached, dry, woven, cotton fabric 10 weighing 4 oz. per sq. yd. is passed at a rate of 50 yards per minute over guide roll 11 and into pad box 12 having therein at 150 F. an aqueous pigment dispersion of azo-disulfide dye, which dispersion, contains 2 oz.
  • the fabric passes between rubber coated pressure rollers 17 and into steamer 18 maintained at 212-215 F., where the fabric is subjected to neutral air-free steam for one minute.
  • the fabric passes over guide roller 19 and into pad box 20 containing water at 140 F., between rubber coated pressure rollers 21, into pad box 22 having therein at 140 F. an acid-oxidizing agent containing 1 oz. of glacial acetic acid and 1 oz. of sodium bichromate per gallon of water, between rubber coated pressure rollers 23, into pad box 24 having therein water at F., between rubber coated pressure rollers 25, into pad box 26, containing at 170 F. 0.5 oz.
  • Example 11 This example is the same as Example I above, except that pad box 12 contains 1 oz. per gallon of water of the azo-disulfide dyestuff utilized in Example I plus 1 oz. per gallon of Sulfur Red 5 (0.1. Part II, No. 53,830), as a dispersed pigment, instead of the dye composition utilized in Example I.
  • Example III This example is the same as Example I above, except that the dye composition used in pad box 12 is an aqueous pigment dispersion of azo-disulfide dyestutf consisting of 2 oz. by weight per gallon of water of the concentrated azo-disulfide dyestuff formed by coupling one mole of tetrazotised 424'-diaminodiphenyldisulfide to two moles of 1-phenyl-3-methyl-5-pyrazolone, instead of the dye composition used in Example I; and except that pad box 20 is by-passed; and except that pad box 22 is covered with a hood having a duct and exhaust fan (not shown) for exhausting the hydrogen sulphide gas.
  • the dye composition used in pad box 12 is an aqueous pigment dispersion of azo-disulfide dyestutf consisting of 2 oz. by weight per gallon of water of the concentrated azo-disulfide dyestuff
  • Example I V This example is the same as Example III above, except that pad box 12 contains, per gallon of water, 1.6 oz. of the concentrated azo-disulfide dyestuff utilized in Example III plus 0.4 oz. of concentrated Sulfur Yellow 2 (C.I. Part II, No. 53,120) as a dispersed pigment, instead of the dye composition utilized in Example III.
  • pad box 12 contains, per gallon of water, 1.6 oz. of the concentrated azo-disulfide dyestuff utilized in Example III plus 0.4 oz. of concentrated Sulfur Yellow 2 (C.I. Part II, No. 53,120) as a dispersed pigment, instead of the dye composition utilized in Example III.
  • Example V To viscose rayon fabric weighing 3 oz. per square yard is padded on, at room temperature, a dye composition consisting of, per gallon of Water, 5 oz. of sodium sulfide reducing agent and 2 oz. of the concentrated azo-disulfide dyestuif formed by coupling one mole of diazotized meta-nitroaniline to one mole of 3-methyl-5-pyrazolone, reducing the resulting product with sodium sulphydrate, filtering, drying, and condensing one mole of the dried product with one mole of 2,4,6-trichloro-1,3,5-triazine in the presence of acetone and soda ash at 5 C., and reacting one mole of'the resulting product with one-half mole of 4:4'-diaminodiphenyldisulfide at 20 C.
  • a dye composition consisting of, per gallon of Water, 5 oz. of sodium sulfide reducing agent and 2
  • the fabric is then passed through squeeze rolls to permit about 85% pick-up of dye composition based on fabric weight, steamed for 5 minutes in neutral air-free steam at 212-215 F. to reduce the dyestuff, passed through a hooded and vented pad box containing 1 oz. of glacial acetic acid and 1 oz. of sodium bichromate per gallon of water at 140 to oxidize the dyestufi, and then scoured and dried as above.
  • Example VI This example is the same as Example V above, except that the fabric is passed through a pad box containing water at 150 F. and then through squeeze rolls, subsequent to the steaming step and prior to the oxidizing step in Example V, and except that no hood is required for the pad box.
  • Example VII This example is the same as Example V above, except that nylon fabric is used; except that the dye composition which is at room temperature contains per gallon of water, 7 oz. of Sodyesul Liquid Green NCF (which is 1.4 oz. concentrated Sulfur Green 2, Cl. Part II, No. 53,571, reduced with an excess of sodium hydrosulfide), 5 oz. of sodium sulfide, and 1 oz.
  • Sodyesul Liquid Green NCF which is 1.4 oz. concentrated Sulfur Green 2, Cl. Part II, No. 53,571, reduced with an excess of sodium hydrosulfide
  • 5 oz. of sodium sulfide and 1 oz.
  • the concentrated non-reduced azo-disulfide dyestufi formed by diazotizing one mole of para-nitroaniline and coupling it to one mole of acetoacet-ortho-anisidide at C., filtering, wash ing, and reducing the resulting product with sodium sulphydrate, condensing one mole of the resulting product with one mole of 2,4,6-trichloro-1,3,5-triazine in the presence of acetone and soda ash at C., and reacting one mole of the resulting product with one-half mole of 2,2'-dichloro-4:4-diaminodiphenyldisulfide at 20 C. as a dispersed pigment.
  • Example VIII This example is the same as Example VII above, except that cotton fabric weighing 4 oz. per square yard is substituted for the nylon fabric, and except that the fabric is passed through a pad box containing water at 150 C, and then squeezed by nip rolls, subsequent to the steaming step and prior to the oxidizing step of Example VII. Also, the pad box need not have a hood.
  • Example IX This example is the same as Example I above, except that the dye composition used in pad .box 12 is an aqueous pigment disperseion of azo-disulfide dyestutf consisting of 2 oz. by weight per gall-on of water of the concentrated azo-disulfide dyest-ulf formed by coupling one mole of diazotized meta-nitraniline to 3-methyl-5-pyrazolone, reducing the resulting product with sodium sulphydrate, filtering, drying and condensing one mole of the dried product with one mole 2,4,6-trichloro-1,3,5-triazine in the presence of acetone and soda ash at 5 C.
  • the dye composition used in pad .box 12 is an aqueous pigment disperseion of azo-disulfide dyestutf consisting of 2 oz. by weight per gall-on of water of the concentrated azo-disulfide dyest-ulf formed by
  • Example X This example is the same as Example IX above except that pad box 12 contains 1 oz. per gallon of water of the azo-disulfide dyestuif utilized in Example IX, plus 5 ozs. per gallon of water of Sodyesul Liquid Blue 4GBCF, which is 1 oz. of concentrated Sulfur Blue 8 reduced with an excess of sodium sulfide and sodium hydrosulfide.
  • Example XI An aqueous pigment dispersion of azo-disulfide dyestuif (2 oz. per gallon of water of the azo-disulfide dyestufi formed by coupling one mole of diazotized S-thiocyano-2-aminotoluene to one mole of beta-naphthol) is padded on cotton fabric at room temperature, pickup. The fabric is dried to substantial dryness, passed through a pad box containing 5 oz. of sodium polysulfide per gallon of water at 150 F., steamed for one minute with neutral air-free steam at 2'12215 F., passed through a hooded and vented pad box containing 1 oz.
  • Example XII onto cotton fabric the fabric is dried to substantial dryness at 240 F., steamed with neutral air-free steam for 2 minutes at 212215-F.; and then washed, oxidized, scoured and dried as described in 19-47 of Example 1.
  • Example XIII This example is the same as Example I above, except that a dye composition consisting of, per gallon of water, 3 oz. concentrated Sulfur Black No. 1, CI. Part II, No. 53185, in solubilized, oxidized, non-substantive form, which is the water soluble thiosulfonic acid derivative of the sulfur dye, and 1.2 oz.
  • Example XIV This example is the same as Example X above, ex cept that the washing subsequent to steaming is eliminated by by-passin-g pad box 20, and box 22 is hooded as discussed above.
  • Example XV This example is the same as Example XII above, except that the washing subsequent to steaming is eliminated by by-passing pad box 20, and box 22 is hooded as discussed above.
  • Example XVI This example is the same as Example XII above, exept that 0.2 -oz. of Sulfur red 5, as dispersed pigment, is added to each gallon of the dye composition of Example XII.
  • Example XVII This example is the same as Example XIII above, except that oz. of thiourea and 3 oz. of NaOH are added to each gallon of the dye composition of Example XIII, and except that the reducing agent of pad 16 is bypassed.
  • Example XVIII This example is the same as Example XVII, except that the washing following steaming is omitted by bypassing box 20.
  • the delayed action reducing agents it should be noted that they do not react with acid to produce hydrogen sulfide gas.
  • a method for dyeing textile fibers comp-rising the steps of padding onto the fibers an aqueous dye composition comprising azo-disulfide dyestuff pigment, reducing the dyest-uif whereby the azo-disulfide dyestuff pigment is reduced at the disulfide bond, oxidizing the dyestuff, scouring and drying the fibers.
  • a method for dyeing textile fibers comprising the steps of padding onto the fibers an aqueous dye composition comprising dyestuif selected from the group consisting of azo-disulfide dyestuff pigment and azo-disulfide dyestuff pigment plus sulfur dye pigment, drying the fibers, applying reducing agent to the fibers, steaming the fibers, oxidizing the dyestufi, scouring and drying the fibers.
  • a method for dyeing textile fibers comprising the steps of padding onto the fibers a dye composition comprising water, alkali, delayed action reducing agent, and dyestuif selected from the group consisting of non-reduced azo-disulfide dyestuff pigment and non-reduced azo-disulfide dyestulf pigment plus non-reduced sulfur dye, steaming the fibers to reduce the dyestuff whereby the azodisulfide dyestuff pigment is reduced at the disulfide bond, oxidizing the dyestuff, scouring and drying the fibers.
  • a method for dyeing textile fibers comp-rising the steps of padding onto the fibers a dye composition comprising water, delayed action reducing agent, alkali, dissolved non-reduced sulfur dye, and non-reduced azodi'sulfide dyest'uff pigment, drying the fibers, steaming the fibers to reduce the dyestuif whereby the azo-disulfide dyestuif pigment is reduced at the disulfide bond, oxidizing the dyestuff, scouring and drying the fibers.
  • Cellulosic textile fabric dyed with a mixture of azo-disulfide dyestuff and sulfur dye.

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US264413A 1963-03-11 1963-03-11 Process for dyeing textile fibers with azo-disulfide and sulfur dyestuffs and dyed products thereof Expired - Lifetime US3264053A (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
US264044A US3329477A (en) 1963-03-11 1963-03-11 Method for printing dyestuffs and printing pastes
US264413A US3264053A (en) 1963-03-11 1963-03-11 Process for dyeing textile fibers with azo-disulfide and sulfur dyestuffs and dyed products thereof
US264045A US3225025A (en) 1963-03-11 1963-03-11 Disazo disulfide dyestuffs
US307014A US3299040A (en) 1963-03-11 1963-09-06 Disazo-disulfide dyes
NL6402179A NL6402179A (es) 1963-03-11 1964-03-04
NL6402178A NL6402178A (es) 1963-03-11 1964-03-04
NL6402184A NL6402184A (es) 1963-03-11 1964-03-04
NL6402183A NL6402183A (es) 1963-03-11 1964-03-04
NL6402180A NL6402180A (es) 1963-03-11 1964-03-04
NL6402181A NL6402181A (es) 1963-03-11 1964-03-04
GB10154/64A GB1016085A (en) 1963-03-11 1964-03-10 Printing cellulosic materials with sulfur and azo-disulfide dyes
GB10157/64A GB1016850A (en) 1963-03-11 1964-03-10 Method for dyeing and dyed product
BE644979D BE644979A (es) 1963-03-11 1964-03-10
BE644984D BE644984A (es) 1963-03-11 1964-03-10
BE644985D BE644985A (es) 1963-03-11 1964-03-10
GB10155/64A GB1020706A (en) 1963-03-11 1964-03-10 Printing cellulosic material with sulfur and azo-disulfide dyes
GB10160/64A GB1018459A (en) 1963-03-11 1964-03-10 Dis azo-disulfide dyes and method for making same
BE644980D BE644980A (es) 1963-03-11 1964-03-10
BE644982D BE644982A (es) 1963-03-11 1964-03-10
ES0297453A ES297453A1 (es) 1963-03-11 1964-03-10 Metodo para tenir fibras textiles
GB10156/64A GB1014703A (en) 1963-03-11 1964-03-10 Method for dyeing
BE644983D BE644983A (es) 1963-03-11 1964-03-10
GB10159/64A GB1025043A (en) 1963-03-11 1964-03-10 Disazo-disulfide dyestuffs and method for making same

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415609A (en) * 1965-04-26 1968-12-10 Martin Marietta Corp Method for fixing dyes on textile fibers and textile fibers resulting from method
US3419343A (en) * 1965-05-28 1968-12-31 Martin Marietta Corp Method for coloring cellulose textile fibers with dyestuffs containing pendant thiosulfate groups

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE590397A (es) * 1960-12-06
US2002406A (en) * 1930-06-21 1935-05-21 Matieres Colorantes & Prod Chi Process of dyeing
US2174486A (en) * 1937-03-17 1939-09-26 Du Pont Textile printing pastes containing penetrating agents and processes of printing therewith
US2663613A (en) * 1950-05-10 1953-12-22 Du Pont Process for coloring nylon fiber
US3088790A (en) * 1959-04-30 1963-05-07 Hoechst Ag Dyeings and prints possessing fastness to wet processing and their manufacture on cellulose material
US3098064A (en) * 1959-04-24 1963-07-16 Hoechst Ag Water-soluble disazo dyes containing two thiosulfuric acid groups

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2002406A (en) * 1930-06-21 1935-05-21 Matieres Colorantes & Prod Chi Process of dyeing
US2174486A (en) * 1937-03-17 1939-09-26 Du Pont Textile printing pastes containing penetrating agents and processes of printing therewith
US2663613A (en) * 1950-05-10 1953-12-22 Du Pont Process for coloring nylon fiber
US3098064A (en) * 1959-04-24 1963-07-16 Hoechst Ag Water-soluble disazo dyes containing two thiosulfuric acid groups
US3088790A (en) * 1959-04-30 1963-05-07 Hoechst Ag Dyeings and prints possessing fastness to wet processing and their manufacture on cellulose material
BE590397A (es) * 1960-12-06

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415609A (en) * 1965-04-26 1968-12-10 Martin Marietta Corp Method for fixing dyes on textile fibers and textile fibers resulting from method
US3419343A (en) * 1965-05-28 1968-12-31 Martin Marietta Corp Method for coloring cellulose textile fibers with dyestuffs containing pendant thiosulfate groups

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