US2903325A - Process for producing or stripping dyeings - Google Patents

Process for producing or stripping dyeings Download PDF

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US2903325A
US2903325A US658527A US65852757A US2903325A US 2903325 A US2903325 A US 2903325A US 658527 A US658527 A US 658527A US 65852757 A US65852757 A US 65852757A US 2903325 A US2903325 A US 2903325A
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complex
polyvinyl
pyrrolidone
dyeing
wool
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US658527A
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Geigy Wilhelm
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BASF Schweiz AG
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Ciba 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D06P3/20—Wool using mordant dyes using metallisable 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5242—Polymers of unsaturated N-containing compounds
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing
    • 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
    • Y10S8/907—Nonionic emulsifiers for dyeing
    • 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
    • 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
    • Y10S8/917—Wool or silk
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • polyvinyl-pyrrolidone if desired, in conjunction with another ion-free agent, is a good levelling agent or stripping agent in the production or stripping of dyeings on nitrogenous basic fibrous materials of complex metal compounds, especially chromium or cobalt compounds, of monoazodyestuffs free from sulfonic acid groups and containing less than one atomic proportion of metal boundin complex union per molecular proportion of monoazo-dyestufif.
  • polyvinyl-pyrrolidone For the purposes of the present invention ordinary commercial polyvinyl-pyrrolidone may be used. There are suitable e.g. polyvinyl-pyrrolidones having a molecular weight ranging from 5000 to 50,000 (average 25,000), those having a molecular weight ranging from 20,000 to 80,000 (average 50,000) or those having an average molecular weight of 700,000. As ion-free agents which may, if desired, be used in conjunction with the polyvinyL pyrrolidone there come into consideration more especially ethylene oxide condensation products of fatty alcohols, of fatty amines or of alkyl-phenols.
  • the relative proportions of the polyvinyl-pyrrolidone and the other ionfree agent may vary within wide limits, but there are advantageously used mixtures of which at least one half consists of polyvinyl-pyrrolidone.
  • the levelling agent may simply be added to the dyebath.
  • the proportion in which it is added usually amounts to a few parts per mil on the weight of the fibrous material.
  • the stripping of a dyeing by the process of the invention is advantageously carried out at a raised temperature, for example, at the boiling temperature. For this purpose it usually suffices to use a few parts percent of the stripping agent calculated on the weight ofthe fibrous material. If desired, a reducing compound, such as a hydrosulfite, may also be added.
  • nitrogenous basic fibrous materials on which a dyeing may be produced or from which a dyeing may be stripped, there come into consideration more especially wool, and also silk or synthetic fibers having similar properties obtained from casein or polyamide or polyurethane fibers.
  • mixtures of basic fibers with other fibers for example, nitrogenous non-basic fibers, such as polyacrylonitrile fibers, and also fibers of polyvinyl chloride or polyester fibers.
  • the fibrous material may be treated in loose condition or in the form of a yarn, hank or fabric, or in the form of foil. The present process is especially suitable for the treatment of wool.
  • Example 1 W001 is dyed at the boiling temperature in a dyebath, which has been adjusted with sodium phosphate to a pH value of 6.5 and contains 0.25% of the bordeaux dyeing cobalt complex of the dyestufi of the formula OH OH 01 SiOaNHg Cl and 0.25% of a mixture of equal parts of polyvinylpyrrolidone and the condensation product of one molecular proportion of commercial octadecyl alcohol with about 25 molecular proportions of ethylene oxide. (The percentages are calculated on the weight of the fibrous material).
  • the dyeing is then finished in the usual manner. There is obtained a substantially more level dyeing than is obtained without the addition of the levelling agent.
  • the yellowish red dyeing chromium 1:2 complex of the dyestuff of the formuia can be used to produce more level dyeings.
  • Example 2 In order to strip a dyeing the procedure may be as follows: Wool, which has been dyed with 1% of the reddish blue dyeing chromium complex of the dyestutt of the formula is treated for one hour at the boiling temperature and at a liquor ratio of 1:40 in a bath which contains 4% of polyvinyl-pyrrolidone calculated on the weight of the fibrous material. The material is then rinsed and dried. The dyestufi is stripped to a considerable extent in this manner.
  • a smaller quantity of polyvinyl-pyrrolidone may be used, for example, 1 or 2% and in this manner the dyeing is rendered considerably lighter.
  • polyvinyl-pyrrolidone a1one instead of using polyvinyl-pyrrolidone a1one,there may be used the mixture described in Example 1 or a mixture 3 of 'polyvinyl pyrrolidone and a condensation product of 1 -molecular-proportion of -oleylamine and -10-14-molecular proportions of ethylene oxide.
  • Example 3 k A wool fabric is dyed at the boiling temperature in-a dyebath which has been adjusted with ammoniumacetate to a pH value of 6.3 and contains 0.25% of the reddyeing cobalt :1 :2 complex of the dyestulf of the formula on on formula OH OH SOZNHCHS
  • the steel blue dyeing chromium 1:2 complex of the dye- "stufi of the formula OHNS I S OiNHl Similar results are obtained by using a polyvinyl-pyrrolidone having an average molecular weight of 700,000 instead of a polyvinyl-pyrrolidone having an average molecular weight of 40,000.
  • Example 4 A'wool fabric is dyed at the boilingtemperature in a dyebath which has been adjusted with ammonium acetate to a pH value of 6.3 1 and contains -'0Z25% of the" brown .4 dyeing chromium 1:2 complex of the dyestufi of the formula and 0.2 ofapolyvinyl pyrrolidonehavingan average molecular weight 40,000. '(The percentages are calculated on the weight of the fibrousmaterial.) The dyeing is then finished in the usual manner. There is obtained a substantially morelevel dyein g 'than is ob'tained without the addition of the levellingagent.
  • Example 5 A Wool fabric is dyed atthe boiling temperature in a dyebath which has been adjusted with ammonium acetate to a pH valueof 6.3 and contains 0.25% of the green dyeingcobalt 1:2-complex'of the dyestufi of the formula and 0.2% of a'polyvinyl-pyrrolidone having an average molecular 'weight-of"700, 000. (The percentages are-calculated-on theweight of the fibrous materiaL) The dyeing is then finished in the'usual manner. There is obtained a subs'tantiallv'more level dyeing than is obtained "without the addition of the levelling agent.
  • the lilac dyeing chromium 1:2 complex of the dyestufl? of the formula The-greendyeing-chromium 1:2 complex or the greyis'hviolet dyeing cobalt 1:2 complex of the dyestufi of the "formula OH OH
  • the steel-blue dyeing chromium 1:2 complex of the dyestufl? of the formula I THCOOH 1 Similar results are obtained by using a polyvinyl-pyrrolidone having an average molecular weight of 40,000 instead of a polyvinyl-pyrrolidone having an average molecular weight of 700,000.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)

Description

2,903,325 Patented Sept. 8, 1959 PROCESS FOR PRODUCING OR STRIPPING DYEINGS Wilhelm Geigy, Binningeu, Switzerland, assignor to Ciba Limited, Basel, Switzerland, :1 Swiss firm No Drawing. Application May 13, 1957 Serial No. 658,527
Claims priority, application Switzerland January 29, 1954 8 Claims. (Cl. 8-43) This application is a continuation-in-part of my copending application Serial No. 484,057, filed January 25, 1955 (and abandoned since the filing of the present application).
This invention is based on the observation that polyvinyl-pyrrolidone, if desired, in conjunction with another ion-free agent, is a good levelling agent or stripping agent in the production or stripping of dyeings on nitrogenous basic fibrous materials of complex metal compounds, especially chromium or cobalt compounds, of monoazodyestuffs free from sulfonic acid groups and containing less than one atomic proportion of metal boundin complex union per molecular proportion of monoazo-dyestufif.
For the purposes of the present invention ordinary commercial polyvinyl-pyrrolidone may be used. There are suitable e.g. polyvinyl-pyrrolidones having a molecular weight ranging from 5000 to 50,000 (average 25,000), those having a molecular weight ranging from 20,000 to 80,000 (average 50,000) or those having an average molecular weight of 700,000. As ion-free agents which may, if desired, be used in conjunction with the polyvinyL pyrrolidone there come into consideration more especially ethylene oxide condensation products of fatty alcohols, of fatty amines or of alkyl-phenols. There may be mentioned, for example, the condensation product of 1 molecular proportion of para-tertiary-octyl-phenol with about 8 molecular proportions of ethylene oxide or the condensation product of 1 molecular proportion of octadecyl alcohol with about 25 molecular proportions of ethylene oxide, and also the condensation product of 1 molecular proportion of oleylamine with about 12 molecular proportions of ethylene oxide. The relative proportions of the polyvinyl-pyrrolidone and the other ionfree agent may vary within wide limits, but there are advantageously used mixtures of which at least one half consists of polyvinyl-pyrrolidone.
The dyeing with a complex metal compound of the kind described above, of which a large number is known in the literature, is carried out in the usual manner. The levelling agent may simply be added to the dyebath. The proportion in which it is added usually amounts to a few parts per mil on the weight of the fibrous material.
The stripping of a dyeing by the process of the invention is advantageously carried out at a raised temperature, for example, at the boiling temperature. For this purpose it usually suffices to use a few parts percent of the stripping agent calculated on the weight ofthe fibrous material. If desired, a reducing compound, such as a hydrosulfite, may also be added.
As nitrogenous basic fibrous materials, on which a dyeing may be produced or from which a dyeing may be stripped, there come into consideration more especially wool, and also silk or synthetic fibers having similar properties obtained from casein or polyamide or polyurethane fibers. There may also be used mixtures of basic fibers with other fibers, for example, nitrogenous non-basic fibers, such as polyacrylonitrile fibers, and also fibers of polyvinyl chloride or polyester fibers. The fibrous material may be treated in loose condition or in the form of a yarn, hank or fabric, or in the form of foil. The present process is especially suitable for the treatment of wool.
The following examples illustrate the invention, the parts being by weight unless otherwise stated and the relationship of parts by weight to parts by volume being the same as that of the kilogram to the liter.
Example 1 W001 is dyed at the boiling temperature in a dyebath, which has been adjusted with sodium phosphate to a pH value of 6.5 and contains 0.25% of the bordeaux dyeing cobalt complex of the dyestufi of the formula OH OH 01 SiOaNHg Cl and 0.25% of a mixture of equal parts of polyvinylpyrrolidone and the condensation product of one molecular proportion of commercial octadecyl alcohol with about 25 molecular proportions of ethylene oxide. (The percentages are calculated on the weight of the fibrous material). The dyeing is then finished in the usual manner. There is obtained a substantially more level dyeing than is obtained without the addition of the levelling agent.
In the same manner the yellowish red dyeing chromium 1:2 complex of the dyestuff of the formuia can be used to produce more level dyeings.
Similar results are obtained by using polyvinyl-pyrrolidone alone, instead of the aforesaid mixture.
Example 2 In order to strip a dyeing the procedure may be as follows: Wool, which has been dyed with 1% of the reddish blue dyeing chromium complex of the dyestutt of the formula is treated for one hour at the boiling temperature and at a liquor ratio of 1:40 in a bath which contains 4% of polyvinyl-pyrrolidone calculated on the weight of the fibrous material. The material is then rinsed and dried. The dyestufi is stripped to a considerable extent in this manner.
A smaller quantity of polyvinyl-pyrrolidone may be used, for example, 1 or 2% and in this manner the dyeing is rendered considerably lighter.
Instead of using polyvinyl-pyrrolidone a1one,there may be used the mixture described in Example 1 or a mixture 3 of 'polyvinyl pyrrolidone and a condensation product of 1 -molecular-proportion of -oleylamine and -10-14-molecular proportions of ethylene oxide.
Example 3 k A wool fabric is dyed at the boiling temperature in-a dyebath which has been adjusted with ammoniumacetate to a pH value of 6.3 and contains 0.25% of the reddyeing cobalt :1 :2 complex of the dyestulf of the formula on on formula OH OH SOZNHCHS The red dyeing cobalt 1:2 complex of the dyestufi of the formula OH OH OgNHCH OHaOH The steel blue dyeing chromium 1:2 complex of the dye- "stufi of the formula OHNS I S OiNHl Similar results are obtained by using a polyvinyl-pyrrolidone having an average molecular weight of 700,000 instead of a polyvinyl-pyrrolidone having an average molecular weight of 40,000.
Example 4 A'wool fabric is dyed at the boilingtemperature in a dyebath which has been adjusted with ammonium acetate to a pH value of 6.3 1 and contains -'0Z25% of the" brown .4 dyeing chromium 1:2 complex of the dyestufi of the formula and 0.2 ofapolyvinyl pyrrolidonehavingan average molecular weight 40,000. '(The percentages are calculated on the weight of the fibrousmaterial.) The dyeing is then finished in the usual manner. There is obtained a substantially morelevel dyein g 'than is ob'tained without the addition of the levellingagent.
In the same manner, the brownish'red dyeing cobalt 1:2 complex of the formula .can'beused to=produce more level dyeings.
Similar-results areobtained by using a polyvinyl-pyrrolidone having an average molecular weight of 700,000
instead of a polyvinyl-pyrrolidone having an average molecular weight of 40,000.
Example 5 A Wool fabric is dyed atthe boiling temperature in a dyebath which has been adjusted with ammonium acetate to a pH valueof 6.3 and contains 0.25% of the green dyeingcobalt 1:2-complex'of the dyestufi of the formula and 0.2% of a'polyvinyl-pyrrolidone having an average molecular 'weight-of"700, 000. (The percentages are-calculated-on theweight of the fibrous materiaL) The dyeing is then finished in the'usual manner. There is obtained a subs'tantiallv'more level dyeing than is obtained "without the addition of the levelling agent.
'In the same'manner the following metal complexes of monoazo-dyes'tufis can be'used to produce more level dyeings: v
The lilac dyeing chromium 1:2 complex of the dyestufl? of the formula The-greendyeing-chromium 1:2 complex or the greyis'hviolet dyeing cobalt 1:2 complex of the dyestufi of the "formula OH OH The greyish green dyeing chromium 1:2 complex of the dyestufi of the formula OH OH OzN EN And the steel-blue dyeing chromium 1:2 complex of the dyestufl? of the formula I THCOOH 1 Similar results are obtained by using a polyvinyl-pyrrolidone having an average molecular weight of 40,000 instead of a polyvinyl-pyrrolidone having an average molecular weight of 700,000.
What is claimed is:
1. In the process of shifting the distribution equilibrium, between an aqueous dye bath and wool, of a complex metal compound of a monoazo dyestuff which is free from sultonic acid groups O -catlon and contains less than one atomic proportion of a metal selected from the group consisting of cobalt and chromium bound in complex union per molecular proportion of dyestuir", the improvement of simultaneously incorporating into said aqueous bath polyvinyl-pyrrolidone, in addition to said wool and said complex metal compound.
2. In the process of shifting the distribution equilibrium, between an aqueous dye bath and Wool, of a complex metal compound of an ortho,ortho'-dihydroxy-monoazo dyestutf which is free from sulfonic acid groups O-cation and contains less than one atomic proportion of a metal selected from the group consisting of cobalt and chromium bound in complex union per molecular proportion of dyestufi and which further contains at least one sulfamide group in an aromatic nucleus, the improvement of simultaneously incorporating into said aqueous bath polyvinyl-pyrrolidone, in addition to said wool and said com.- plex metal compound.
4. In the process of shifting the distribution equilibrium, between an aqueous dye bath and wool, of a com- 6 plex metal compound of an ortho,ortho'-dihydroxy monoazo dyestufi which is free from sulfonic acid groups O-cation and contains less than one atomic proportion of a metal selected from the group consisting of cobalt and chromium bound in complex union per molecular proportion of dyestuff and which further contains at least one sulfamide group in an aromatic nucleus, the improvement of simultaneously incorporating into said aqueous bath poly vinyl-pyrrolidone and a condensation product of a fatty alcohol with ethylene oxide, in addition to said wool and said complex metal compound.
5. In the process of shifting the distribution equilibrium, between an aqueous dye bath and Wool, of a complex metal compound of an ortho,ortho-dihydroxy monoazo dyestuif which is free from sulfonic acid groups O-cation and contains less than one atomic proportion of a metal selected from the group consisting of cobalt and chromium bound in complex union per molecular proportion of dycstuif and which further contains at least one sulfa-mide group in an aromatic nucleus, the improvement of simultaneously incorporating into said aqueous bath polyvinylpyrrolidone and the condensation product of 1 molecular proportion of octadecyl alcohol with about 25 molecular proportions of ethylene oxide, in addition to said wool and said complex metal compound.
6. In the process of shifting the distribution equilibrium, between an aqueous dye bath and wool, of a complex chromium compound of an ortho,ortho'-dihydroxy monoazo dyestutf which is free from sulfonic acid groups O-cation and contains less than one atomic proportion of chromium bound in complex union per molecular proportion of dyestuff and which further contains at least one sulfonamide group in an aromatic nucleus, the improvement of simultaneously incorporating into said aqueous bath polyvinyl-pyrrolidone, in addition to said wool and said complex chromium compound.
7. In the process of shifting the distribution equilibrium, between an aqueous dye bath and wool, of a complex cobalt compound of an ortho,ortho-dihydroxy monoazo dyestuff which is free from sulfonic acid groups and contains less than one atomic proportion of cobalt bound in complex union per molecular proportion of dyestuif and which further contains at least one sulfonamide group in an aromatic nucleus, the improvement of simultaneously incorporating into said aqueous bath polyvinylpyrrolidone, in addition to said wool and said complex cobalt compound.
8. In the process of shifting the distribution equilib rium, between an aqueous dye bath and Wool, of a complex metal compound of an ortho,ortho'-dihydroxy monoazo dyestufi which is free from sulfonic acid groups O-cation and contains less than one atomic proportion of a metal selected 'from'the :group consisting'of cobalhand chro- 'ular :proportionsof ethylene oxide in addition-to :said
mium bound in icomplex union-per mole'culanproportion wool and said complex metal compound. of dyestufi and which further contains at least one sulfamide group in an aromatic'nucleus, the improvement of References Cited in the me of this PAtent simultaneously incorporating into said aqueous bath a Melliand, XXXII, "for January 1951, pp. 53-56. polyvinyl-pyrrolidone andzthe condensation product of 1 American Dyestuff Reporter for Feb. 1, 1954, pp.
molecular proportion of .oleylamine with 1010 14 molec- 7 75.

Claims (1)

1. IN A PROCESS OF SHIFTING THE DISTRIBUTION EQUILIBRIUM, BETWEEN AN AQUEOUS DYE BATH AND WOOL, OF A COMPLEX METAL COMPOUND OF A MONOAZO DYESTUFF WHICH IS FREE FROM SULFONIC ACID GROUPS
US658527A 1954-01-29 1957-05-13 Process for producing or stripping dyeings Expired - Lifetime US2903325A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955011A (en) * 1956-07-16 1960-10-04 Gen Aniline & Film Corp Dyestuff compositions
US2970880A (en) * 1958-06-10 1961-02-07 American Cyanamid Co Soluble vat dye printing compositions with heterocyclic solubilizing agents
US3086831A (en) * 1959-07-01 1963-04-23 American Cyanamid Co Compositions of a pyrazolone azo dye with polyvinylpyrrolidone
US3232695A (en) * 1966-02-01 Process for dyetng materials based on polyamedes and composithons therefor
US3239302A (en) * 1955-11-28 1966-03-08 Ciba Ltd Process for shifting the dyestuff equilibrium of 1:2 metal complex azo-dyes
US3241905A (en) * 1961-09-25 1966-03-22 Ciba Ltd Vat dye leveling with copolymers 2-oxo-nu-vinyl heterocyclic compound and acrylamides
US5820638A (en) * 1996-06-26 1998-10-13 Burlington Chemical Co., Inc. Stain blocking agent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232695A (en) * 1966-02-01 Process for dyetng materials based on polyamedes and composithons therefor
US3239302A (en) * 1955-11-28 1966-03-08 Ciba Ltd Process for shifting the dyestuff equilibrium of 1:2 metal complex azo-dyes
US2955011A (en) * 1956-07-16 1960-10-04 Gen Aniline & Film Corp Dyestuff compositions
US2970880A (en) * 1958-06-10 1961-02-07 American Cyanamid Co Soluble vat dye printing compositions with heterocyclic solubilizing agents
US3086831A (en) * 1959-07-01 1963-04-23 American Cyanamid Co Compositions of a pyrazolone azo dye with polyvinylpyrrolidone
US3241905A (en) * 1961-09-25 1966-03-22 Ciba Ltd Vat dye leveling with copolymers 2-oxo-nu-vinyl heterocyclic compound and acrylamides
US5820638A (en) * 1996-06-26 1998-10-13 Burlington Chemical Co., Inc. Stain blocking agent

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