US3684426A - Levelling polyamide fiber dyeing with sulfonated long chain alkyl diphenyl ether and quaternized long chain alkyl ammonium alkylene oxide condensate - Google Patents

Levelling polyamide fiber dyeing with sulfonated long chain alkyl diphenyl ether and quaternized long chain alkyl ammonium alkylene oxide condensate Download PDF

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US3684426A
US3684426A US15841A US3684426DA US3684426A US 3684426 A US3684426 A US 3684426A US 15841 A US15841 A US 15841A US 3684426D A US3684426D A US 3684426DA US 3684426 A US3684426 A US 3684426A
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Prior art keywords
dyeing
chain alkyl
long chain
fibre material
polyamide
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US15841A
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Jakob Bindler
Rudolf Keller
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Classifications

    • 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
    • D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts
    • D06P1/625—Aromatic
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • 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
    • D06P3/24—Polyamides; Polyurethanes
    • 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
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • 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
    • Y10S8/90—Basic 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • 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
    • Y10S8/93—Pretreatment before dyeing

Definitions

  • the present invention relates to a process for the even, non-streaky dyeing of fibre material made from synthetic polyamide of differing dyestulT-afiinity, as Well as to the fibre material dyed using this process.
  • fibre material made from synthetic polyamide having differing dyestuff-aflinity such as textured polyamide fibre material, e.g. Banlon
  • textured polyamide fibre material e.g. Banlon
  • aqueous solution of a mixture of auxiliaries consisting of (a) at least one anion-active compound of Formula I,
  • R represents an alkyl radical having from 8 to 18 carbon atoms
  • X represents a cation and n represents a number from 1 to 2
  • Anion-active compounds of Formula I are known per se and can be produced, e.g. by the methods described in British Pats. Nos. 912,340 and 1,043,043, by reacting correspondingly substituted diphenyl ethers together with a sulphonating agent, such as sulphur trioxide or chlorosulphonic acid, in the solution of a poly-chlorinated aliphatic hydrocarbon, or by dissolving the diphenyl ether compound in a saturated aliphatic hydrocarbon and then bringing it into contact with the sulphonating agent.
  • a sulphonating agent such as sulphur trioxide or chlorosulphonic acid
  • Anion-active compounds of Formula I which have proved particularly valuable, in the process according to the invention, are those wherein R represents an alkyl radical having from 9 to 12 carbon atoms, X represents an alkali metal ion, such as the lithium or potassium ion, preferably, however, the sodium ion, or the ammonium ion and n represents the number 2.
  • Disulphonated compounds of Formula I which are obtained by sulphonating the 4-dodecyldiphenyl ether, are especially preferred.
  • the cation-active, non-quaternated or quaternated compounds (b), usable in the process according to the invention, are likewise known per se and can be produced in a manner known per se, e.g. by reaction of the corresponding aliphatic amines, especially long-chain primary alkylmono-, -dior -tri-arnines, the alkyl or alkenyl radical of which contains from 10 to 18 carbon atoms, such as dodecyl-, octadecylor octadecenylamine, dodecylpropylenediamine, octadecylethylenediamine and octadecyldiethylenetriamine, with alkylene oxides, e.g.
  • Suitable cationactive compounds (b), usable according to the invention are also products obtained by reaction of the above mentioned alkylamines with from 1 to 2 equivalents of styrene oxide, from 0 to 2 equivalents of propylene oxide and from 1 to 19 equivalents of ethylene oxide as well as, optionally, subsequent quaternisation.
  • R represents an alkyl or alkenyl radical having from 10 to 18 carbon atoms, especially the octadecenyl or the octadecyl radical,
  • R represents a lower alkyl radical having from 1 to 4 carbon atoms, particularly the methyl group
  • n 0 or 1
  • n and p represent whole numbers, the sum of which is from 6 to 20, especially from 11 to 18, and
  • A represents an anion, particularly the methosulphate ion.
  • n and p represent a mean value, and there are present mixtures of analogous compounds with polyalkyleneoxy substituents of varying chain-length.
  • Anionic dyestuffs suitable for the process according to the invention, can belong to very diverse classes of dyestuffs. These can be, for example, the commercially important dyestulf classes of the azo, anthraquinone, phthalocyanine, nitro or formazane dyestuffs which can also contain metals bound in complex linkage such as copper, nickel, chromium or cobalt. Suitable azo dyestuffs are, principally, monoazo dyestuffs, e.g.
  • the 2120 dyestuffs to which also belong the formazane dyestutfs, can be metallised, principally by chromium or cobalt, but also by cop per or nickel, whereby 1 or 2 dyestufi molecules per metal ion participate in the complex.
  • the pH-value of the dye bath is adjusted to the desired value by the addition of an acid, such as acetic acid, formic acid or sulphuric acid.
  • the weight ratio of anion-active to cation-active compound is thereby advantageously from 1:1 to :1.
  • the acidity of the dye liquor can be reduced by the addition of an acid-binding agent, such as an alkali metal hydroxide, -carbonate or -hydrogen carbonate, by the addition of ammonium hydroxide, disodium or dipotassium phosphate, sodium or potassium acetate, as well as by the addition of hexamethylenetetramine.
  • an acid-binding agent such as an alkali metal hydroxide, -carbonate or -hydrogen carbonate
  • An advantageous embodiment of the process, according to the invention consists in carrying out the preliminary treatment at boiling temperature, then adding the predissolved dyestufi and completing the dyeing at the same temperature. After the dyeing is completed, the dyed material is advantageously rinsed in the usual manner, if necessary given an aftertreatment to improve the fastness to wet processing, and dried.
  • the anion-active compounds are used in amounts of from 0.1 to 5% by weight, relative to the fibre material to be treated, preferably in amounts of from 0.2 to 2% by weight.
  • the cation-active compounds are, in general, used in amounts of from 0.01 to 2% by weight, preferably in amounts of from 0.05 to 0.5% by weight.
  • the dye bath can contain, e.g. urea, thiourea, thiodiethylene glycol or hydrophilic compounds having limited Watersolubility such as, e.g. butyl alcohol or benzyl alcohol.
  • Further additives are textile-protective agents having afiinity to the fibres and which protect the textile ma terial to be dyed.
  • Suitable fibre materials made from synthetic polyamide are, e.g. condensation products from hexamethylenediamineand adipic acid (Polyamide 6.6) or sebacic acid (Polyamide 6.10) or mixed condensation products, e.g. from hexamethylenediamine, adipic acid and e-caprolactam (Polyamide 6.6/6), also the polymerisation products from e-caprolactam, known under the trade names of Polyamide 6, Perlon, Grilon or Enkalon, or from w-aminoundecanoic acid (Polyarnide 11 or Rilsan).
  • These fibres can be used at any stage of processing, that is to say, e.g. in the form of threads, yarns, knitted goods and fabrics.
  • the process is distinguished in that, even on polyamide fibre material tending to exhibit streakiness upon dyeing, even and non-Streaky dyeings are obtained with, in themselves, poorly levelling dyestufis, with extensive exhaustion of the dye bath.
  • EXAMPLE 1 To 200 ml. of softened water are added 0.1 ml. of 40% acetic acid and 0.1 g. of a mixture, consisting of 0.076 g. of a 45% aqueous solution of the disodium salt of the dodecyldiphenyl ether disulphonic acid, 0.0075 g. of a compoundof the formula CH3 (CHgCH2O) H C1aH 5 OH2ICHO(CHZCHZO)pH 3043113 and 0.0165 g. of water.
  • the temperature of the dye bath is raisedwithin-45 minutes to the boiling point and, as the dye liquor gently boils, dyeing is continued for a further 45 minutes.
  • the dyed material is then rinsed Warm and afterwards cold and finally dried.
  • TAB-LE 1 EXAMPLE 5 To 400 ml. of water at ca. 40 are added 0.075 ml. of 40% acetic acid and 0.2 g. of a mixture consisting of 0.152 g. of a 45% aqueous solution of the disodium salt of the dodecyldiphenyl ether disulphonic acid, 0.015 g. of a compound of the formula and 0.033 g. of water.
  • This auxiliary liquor is pumped into the dyeing apparatus.
  • the temperature of the auxiliary liquor is then rapidly raised to 96 and the material to be dyed is treated at this temperature for 30 minutes.
  • the pH-value of the dye bath is thereupon raised to 6.0 by the addition of aqueous ammonia solution,
  • an addition is made, relative to 7 the weight of textile material, of 0.5% of the dyestuif of the formula which is pre-dissolved in ten times the amount of water, and dyeing proceeds for a further 60- minutes at 96.
  • the red dyed material is then rinsed warm and afterwards cold, and dried.
  • a knitted fabric, produced from the thus dyed yarn, is free of streaks and is uniform.
  • the dye liquor is heated to boiling within 20 minutes. Whilst continuous movement I,
  • the resulting dyeing is appreciably more level than a dyeing obtained without addition of the above-mentioned 1 mixture of auxiliaries.
  • a process for the even, non-streaky dyeing of fibre material made from synthetic polyamide of differing dyestuff-aflinity which comprises (I) applying to said fibre material, at a pH-value of I from 2 to 7 and at temperatures of from 30 to 130 C., with the aqueous solution of a mixture of auxiliaries comprising a (a) at least one anion-active compound of Formula I l so X R L .l a h (I) wherein I R represents an alkyl radical having to 18 carbon atoms, X represents a cation, and I n represents a number from 1 to 2, an
  • R represents an alkyl or alkenyl radical having from 10 to 18 carbon atoms
  • R represents a lower alkyl radical having from 1 to 4 carbon atoms
  • Y represents hydrogen or the phenyl radical
  • m represents 0 or 1 n
  • p represents whole numbers, the sum of which is from 6 to 20, and
  • A represents. an anion; and (II) adding, at temperatures of from 30 to 100 C., predissolved anionic dyestufi and completing the dyeing at the temperature of 30 to 100 C.
  • R represents an alkyl radical having from 9 to 12 carbon atoms
  • X represents an alkali metal ion or the ammonium ion
  • n represents the number 2.
  • a process as claimed in claim 1 employing a weight ratio of anion-active to cation-active compounds of from 1:1 to 10:1.
  • DONALD LEVY DONALD LEVY, Primary Examiner v US. (:1. X.R. a r-172,173, 42 B, 39.

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  • Textile Engineering (AREA)
  • Coloring (AREA)
US15841A 1969-03-24 1970-03-02 Levelling polyamide fiber dyeing with sulfonated long chain alkyl diphenyl ether and quaternized long chain alkyl ammonium alkylene oxide condensate Expired - Lifetime US3684426A (en)

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Application Number Priority Date Filing Date Title
CH438169A CH553286A (enrdf_load_stackoverflow) 1969-03-24 1969-03-24
US1584170A 1970-03-02 1970-03-02

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US (1) US3684426A (enrdf_load_stackoverflow)
BE (1) BE747842A (enrdf_load_stackoverflow)
BR (1) BR7017678D0 (enrdf_load_stackoverflow)
CH (2) CH438169A4 (enrdf_load_stackoverflow)
DE (1) DE1919120A1 (enrdf_load_stackoverflow)
FR (1) FR2044702B1 (enrdf_load_stackoverflow)
GB (1) GB1299777A (enrdf_load_stackoverflow)
NL (1) NL7004125A (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4030880A (en) * 1975-10-09 1977-06-21 E. I. Du Pont De Nemours And Company Process for improving dyeability
US4217103A (en) * 1977-09-24 1980-08-12 Bayer Aktiengesellschaft Dyestuff formulations containing salts of diaryl ether sulfonic acids
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4563192A (en) * 1983-09-19 1986-01-07 Ciba-Geigy Corporation Process for dyeing fibre material made of synthetic polyamides with anionic dyes and an auxiliary mixture
US4563190A (en) * 1982-03-09 1986-01-07 Ciba-Geigy Corporation Dyeing assistant and use thereof for dyeing or printing synthetic polyamide fibre material
US5460632A (en) * 1994-12-29 1995-10-24 Olin Corporation Low-foaming, enhanced wetting dye-leveling agent
US5762650A (en) * 1996-08-23 1998-06-09 Olin Corporation Biocide plus surfactant for protecting carpets
CN113512139A (zh) * 2020-04-10 2021-10-19 刘建敏 羧基丁苯胶乳、水泥基花岗岩板及其制备方法

Families Citing this family (7)

* 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
DE3110731C2 (de) * 1981-03-16 1983-07-28 Bültmann KG, 5982 Neuenrade Vorrichtung zum Einformen von Rohrenden
DE3729459A1 (de) * 1987-09-03 1989-03-16 Bayer Ag Verfahren fuer das faerben von cellulosefasern
US5314504A (en) * 1990-11-15 1994-05-24 E. I. Du Pont De Nemours And Company Process for the application of dye fixing agents to polyamide fiber utilizing controlled fixing agent addition
US5230709A (en) * 1990-11-15 1993-07-27 E. I. Du Pont De Nemours And Company Polyamide dyeing process utilizing controlled anionic dye addition
NZ252563A (en) * 1992-05-15 1996-04-26 Du Pont Dyeing wool; process including use of an anionic dye and immersion of the article to be dyed in a bath of liquid solvent for the anionic dye
AU4944896A (en) * 1995-03-15 1996-10-02 Ciba Specialty Chemicals Holding Inc. Improving the light-fastness of dyes on polyamide fibres

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4030880A (en) * 1975-10-09 1977-06-21 E. I. Du Pont De Nemours And Company Process for improving dyeability
US4217103A (en) * 1977-09-24 1980-08-12 Bayer Aktiengesellschaft Dyestuff formulations containing salts of diaryl ether sulfonic acids
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4563190A (en) * 1982-03-09 1986-01-07 Ciba-Geigy Corporation Dyeing assistant and use thereof for dyeing or printing synthetic polyamide fibre material
US4563192A (en) * 1983-09-19 1986-01-07 Ciba-Geigy Corporation Process for dyeing fibre material made of synthetic polyamides with anionic dyes and an auxiliary mixture
US5460632A (en) * 1994-12-29 1995-10-24 Olin Corporation Low-foaming, enhanced wetting dye-leveling agent
US5762650A (en) * 1996-08-23 1998-06-09 Olin Corporation Biocide plus surfactant for protecting carpets
CN113512139A (zh) * 2020-04-10 2021-10-19 刘建敏 羧基丁苯胶乳、水泥基花岗岩板及其制备方法
CN113512139B (zh) * 2020-04-10 2023-06-13 刘建敏 羧基丁苯胶乳、水泥基花岗岩板及其制备方法

Also Published As

Publication number Publication date
FR2044702B1 (enrdf_load_stackoverflow) 1973-07-13
FR2044702A1 (enrdf_load_stackoverflow) 1971-02-26
BE747842A (fr) 1970-09-23
BR7017678D0 (pt) 1973-01-11
GB1299777A (en) 1972-12-13
CH438169A4 (enrdf_load_stackoverflow) 1974-02-28
CH553286A (enrdf_load_stackoverflow) 1974-08-30
NL7004125A (enrdf_load_stackoverflow) 1970-09-28
DE1919120A1 (de) 1970-11-26

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