US3658460A - Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds - Google Patents

Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds Download PDF

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US3658460A
US3658460A US817568A US3658460DA US3658460A US 3658460 A US3658460 A US 3658460A US 817568 A US817568 A US 817568A US 3658460D A US3658460D A US 3658460DA US 3658460 A US3658460 A US 3658460A
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dye
liquor
acid
dyeing
basic nitrogen
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US817568A
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Adam Mikula
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Sandoz AG
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Sandoz AG
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60General 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 polyethers
    • D06P1/607Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621Compounds without nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/655Compounds containing ammonium groups
    • D06P1/66Compounds containing ammonium groups containing quaternary ammonium groups
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/90Basic emulsifiers for dyeing
    • Y10S8/901Quaternary ammonium salts
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/905Mixed anionic and cationic emulsifiers for dyeing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/907Nonionic emulsifiers for dyeing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • Y10S8/909Sulfonated or sulfated alphatic hydrocarbons
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • Y10S8/91Soap
    • Y10S8/911Sulfonated
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • ABSTRACT A level dyeing is obtained on fabric of synthetic polyamide fibers having a variable dyestuff affinity by treating the fabric at a temperature of from 70 to 130 C.' in a liquor of which the pH value throughout is maintainedbetween 3 and 5,'said dye liquor containing an aqueous solution of a surface active compound containing sulphonic acid groups or a surface active sulphuric acid ester, e.g. a sulphated oil constituted by a high molecular weight fatty acid subjected to a high degree or an ester thereof, to which liquor there is then sequentially added,
  • a surface active compound containing sulphonic acid groups or a surface active sulphuric acid ester e.g. a sulphated oil constituted by a high molecular weight fatty acid subjected to a high degree or an ester thereof, to which liquor there is then sequentially added
  • No Drawings lt is known to dye textile material of synthetic polyamide fibers having variable dyestuff affinity in such a wayas to produce dyeings of level appearance by treating said material before dyeing with an aqueous solution at a pH value of from 3 to 4 and temperatures of preferably 70 to 80 C., said solution containing a sulphated high molecular weight fatty acid or a sulphate ester thereof, if desired in admixture with ethoxylated amines having a high molecular weight fatty acid residue.
  • the pretreatment bath is cooled to 50 C. and the dye and an acid binding agent are only added after such cooling,
  • the present invention thus provides a process for the level dyeing of a textile material of synthetic polyamide fibers having a variable dyestuff affinity with an anionic dye which would normally cause said material to have a stripy appearance, which process comprises first treating the material to be dyed with an aqueous solution of a surface active compound selectedfrom the class consisting of surface active sulphuric acid esters and surface active sulphonic acid group containing substances in a pretreatment bath, then adding to said bath with the textile material still in it, without cooling, a surface active compound selectedfrom the class consisting of surface active sulphuric acid esters and surface active sulphonic acid group containing substances in a pretreatment bath, then adding to said bath with the textile material still in it, without cooling, a surface active compound selectedfrom the class consisting of surface active sulphuric acid esters and surface active sulphonic acid group containing substances in a pretreatment bath, then adding to said bath with the textile material still in it, without cooling, a surface active compound selectedfrom the class consisting of
  • the basic nitrogen containing compound may contain more than one nitrogen atom and the non-cyclic radical may be saturated or unsaturated; the last mentioned radical, which preferably contains 16 24 carbon atoms, may (but need not) contain one or more hetero atoms or groups with hetero atoms, e.g. O, Sor- CONH. H
  • Examples of said surface active compounds are alkylarylsulphonic acids, alkanesulphonic acids, aminoalkylsulphonic acid amides of high molecular weight fatty acids sulphated high molecular weight fatty acids or their esters, e.g.. sulphation products of oleic, elaidic or ricinoleic acid and their esters, especially alkyl ones, for example the methyl, ethyl, propyl or butyl ester, or the glycerine ester of these fatty acids, for example castor oil. Sulphation products having a high degree of sulphation, preferably those with a sulphation degree above 70 percent, are especially suitable.
  • Examples of the basic nitrogen containing compounds are those having the following formulae l-lV:-
  • each of R and R is independently selected ffom' The class consisting of saturated and unsaturated, non-cyclic radicals with 12 to 30, preferably 16 to 24, carbon atoms,
  • R is selected from the class consisting of saturated and unsaturated non-cyc'lic radicals withfrom one to 30 carbon atoms,
  • each of A A and A is independently selected from the class consisting of polyethenoxy chains, withthe proviso that the sum of the ethenoxy groups in all three chains must be at least 20 and at most 200,
  • each of A, and A is independently selected from the class consisting of polyethylene oxide chains, withthe proviso that the sum of the ethenoxy groups for the two chains mustbe at least 20 and at most 200,
  • At least one of X X and X is independently selected from the class consisting of monosubstituted ethylene groups sub stituted with at least one of alkyl and hydroxyalkyl residues having one to 20 carbon atoms and phenyl residues, disubstituted ethylene groups substituted with a polymethylene chain, and disubstituted ethylene groups substituted with 2 non-cyclic, saturated residues each containing from one to 18 carbon atoms (e. g. alkyl radicals), v
  • X X and X is independently selected from the class consisting of single bonds, monosubstituted ethylene groups substituted with at least one of alkyl and hydroxyalkyl residues having one to 20 carbon atoms and phenyl residues, disubstituted ethylene groups substituted with a polymethylene chain, and disubstituted ethylene groups substituted with 2 non-cyclic, saturated residues each containing from one to l8 carbon atoms (e.g. alkyl radicals),
  • n an integer selected from 1, 2, 3, 4, 5 and 6,
  • R, R, and R may contain hetero atoms or groups of hetero atoms, e.g. O, S or -CO- Nl-l-; these three symbols may, however, be aliphatic v radicals.
  • ethylene oxide or of propylene oxide and ethylene oxide to high molecular weight monoor polyarnines, for example, oleyl-, cetyl-,' stearyland behenylaminoethylamine or -propylamine and their quaternization products.
  • the ethoxylated amines may be used either as such or in the form of their quaternization products.
  • Suitable quaternization agents are, for example, dimethylsulphate, diethylsulphate, methyl chloride, benzyl chloride, methylor ethylbenzene sulphonate, methylor ethylpara-methylbenzene sulphonate etc.
  • the pretreatment is effected with a liquor of which the pH value has been adjusted to from 3 to 5 by means of an acid such as, for example, acetic acid, formic acid or sulphuric acid and may last about 10 to 30 minutes.
  • an acid such as, for example, acetic acid, formic acid or sulphuric acid and may last about 10 to 30 minutes.
  • the amount of the said surface active compound may be, for example, from 0.5 to 5 percent of the weight of the fibers; in general, however, 0.7 to 2 percent are sufficient.
  • the amount of the basic compound which may be used is likewise from 0.5 to 5 percent of the weight of the fibers, preferably however about 0.7 to 1.5 percent thereof. All these quantity data relate to percent of active substance.
  • the dyeing may be effected at the boil or at temperatures above 100 C. at superatrnospheric pressure.
  • milling acid dyes for example l,4-bis-[4'-(4- chlorophenoxy)- 2-sulphophenylamino]-anthraquinone or 1- hydroxy-2-(2-phenoxy-5'-chlorophenylazo)-8-(4"- methylphenylsulphonylamino)-naphthalene-3,6-disulphonic acid, and the acid dyes for wool such as l-amino-2-bromo-4- (4-methylphenylamino )-anthraquinone-Z-sulphonic acid.
  • One preferred basic nitrogen containing compound is an addition product of 90 to l mols of ethylene oxide to 1 mol of C ,-alkyl-3-propylamine.
  • the dyestuff may be added simultaneously with or subsequently to said basic nitrogen containing compound or quaternization product thereof.
  • EXAMPLE 1 100 parts of a fabric of Nylon-66 which would normally dye with a stripy appearance are treated for 30 minutes in 4,000 parts of a boiling aqueous liquor of which the pH valve has been adjusted to 4-5 by means of acetic acid and which contains 3.3 parts of castor oil sulphated to 80 percent containing 30 percent of active substance. Thereafter 1.4 parts of an addition product of 100 mols of ethylene oxide and 1 mol of behenylamino-3-propylamine are added to the liquor without cooling it. 1 part of the acid dye Blue 127 (61135), Color Index ll 1956, is then added to the boiling liquor and dyeing is effected for 1 hour. A level blue dyeing is obtained which is level and fast to washing, perspiration and light.
  • EXAMPLE 2 100 parts of a Nylon-6 fabric which would normally dye with a stripy appearance are treated for 30 minutes in 3,000 parts of a boiling aqueous liquor of which the pH value has been adjusted t0'4-5 by means of acetic acid and which contains 4 parts of castor oil which has been to percent and has an active substance content of 30 percent.
  • the dyestuff can be added at the same time as each of the ethylene oxide addition products with similar effect as regards the dyeing obtained.
  • a process for the level dyeing of a textile material of synthetic polyamide fibers having a variable dyestuff affinity with an anionic dye which would normally cause said material to have a stripy appearance comprises first treating the material to be dyed with an aqueous solution of a surface active compound selected from the class consisting of alkylarylsulphonic acids, alkanesulphonic acids, aminoalkylsulphonic acid amides of high molecular weight fatty acids, sulphated high molecular weight fatty acids and esters thereof, to the pretreatment bath, then adding to said bath with the textile material still in it, without cooling, a material selected from the class consisting of basic nitrogen containing compounds, said compounds selected from the following formulae l to IV:
  • each of R and R is independently selected from the class consisting of saturated and unsaturated, non-cyclic radicals with 12 to 30, preferably 16 to 24, carbon atoms, R, is selected from the class consisting of saturated and unsaturated non-cyclic radicals with from one to 30 carbon atoms,
  • each of A A, and A is independently selected from the class consisting of polyethenoxy chains, with the proviso that the sum of the ethenoxy groups in all three chains must be at least and at most 200
  • each of A and A is independently selected from the class 5 consisting of polyethylene oxide chains, with the proviso that the sumof the ethenoxy groups for the two chains must be at least 20 and at most 200
  • at least one of X,, X, and X is independently selected from the class consisting of monosubstituted ethylene groups substituted with at least one of alkyl and hydroxyalkyl residues having one to 20 carbon atoms and phenyl residues, disubstituted ethylene groups substituted with a polymethylene chain, and disubstituted ethylene groups substituted with 2 non-cyclic, saturated residues each containing from one to 18 carbon atoms, and any remaining symbol X X and X is independentlyselected from the class consisting of single bonds, monosubstituted
  • n represents an integer selected from 1, 2, 3, 4, 5 and 6, and m represents an integer selected from 1, 2, 3, 4, 5, 6
  • said lgasic nitrogen containing compound is an addition product of 90 to 100 mols of ethylene oxide to 1 mol of C -alkyl- 3propylarnine.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US817568A 1968-04-26 1969-04-18 Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds Expired - Lifetime US3658460A (en)

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CH629368 1968-04-26

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US (1) US3658460A (enrdf_load_stackoverflow)
AT (1) AT291178B (enrdf_load_stackoverflow)
BE (1) BE731971A (enrdf_load_stackoverflow)
CH (2) CH546301A (enrdf_load_stackoverflow)
DE (1) DE1920357A1 (enrdf_load_stackoverflow)
ES (1) ES366400A1 (enrdf_load_stackoverflow)
FR (1) FR2007035A1 (enrdf_load_stackoverflow)
GB (1) GB1213609A (enrdf_load_stackoverflow)
IL (1) IL32077A (enrdf_load_stackoverflow)
NL (1) NL153622B (enrdf_load_stackoverflow)
SE (1) SE344772B (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4622045A (en) * 1983-09-29 1986-11-11 Sandoz Ltd. Method of dyeing wool with acid dyestuffs
US20020114917A1 (en) * 1999-06-17 2002-08-22 Seiin Kobayashi Methods of coloring solution-dyed nylon

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2633615C3 (de) * 1976-07-27 1981-08-13 Bayer Ag, 5090 Leverkusen Verfahren zum Färben von synthetischen Polyamid-Fasermaterialien
FR2611763B1 (fr) * 1987-03-04 1990-03-09 Sandoz Sa Procede de teinture de polyamides naturels et/ou synthetiques avec des colorants anioniques

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3006935A (en) * 1955-07-15 1961-10-31 Ciba Ltd New polyglycol ether derivatives
US3071427A (en) * 1958-04-30 1963-01-01 Ciba Ltd Process for dyeing nitrogenous fibers and preparations for carrying out the process
US3230029A (en) * 1958-02-21 1966-01-18 Montedison Spa Process for improving synthetic fibers and the dyeable fibers obtained thereby
US3391985A (en) * 1963-02-08 1968-07-09 Geigy Ag J R Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1477232A (fr) * 1966-04-25 1967-04-14 Sandoz Sa Procédé pour teindre de façon unie une matière textile à base de fibres de polyamides synthétiques présentant une affinité variable pour les colorants

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3006935A (en) * 1955-07-15 1961-10-31 Ciba Ltd New polyglycol ether derivatives
US3230029A (en) * 1958-02-21 1966-01-18 Montedison Spa Process for improving synthetic fibers and the dyeable fibers obtained thereby
US3071427A (en) * 1958-04-30 1963-01-01 Ciba Ltd Process for dyeing nitrogenous fibers and preparations for carrying out the process
US3391985A (en) * 1963-02-08 1968-07-09 Geigy Ag J R Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4622045A (en) * 1983-09-29 1986-11-11 Sandoz Ltd. Method of dyeing wool with acid dyestuffs
US20020114917A1 (en) * 1999-06-17 2002-08-22 Seiin Kobayashi Methods of coloring solution-dyed nylon

Also Published As

Publication number Publication date
ES366400A1 (es) 1971-03-16
SE344772B (enrdf_load_stackoverflow) 1972-05-02
GB1213609A (en) 1970-11-25
DE1920357A1 (de) 1970-02-12
IL32077A0 (en) 1969-06-25
IL32077A (en) 1973-06-29
AT291178B (de) 1971-07-12
NL6906200A (enrdf_load_stackoverflow) 1969-10-28
NL153622B (nl) 1977-06-15
FR2007035A1 (fr) 1970-01-02
CH629368A4 (enrdf_load_stackoverflow) 1973-08-31
BE731971A (enrdf_load_stackoverflow) 1969-10-23
CH546301A (enrdf_load_stackoverflow) 1974-02-28

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