US3623834A - Dye solution or print paste containing chlorinated hydrocarbon with an alcohol ketone dioxane alkanoic acid amide tetramethyl urea or pyridine and polyamide dyeing therewith - Google Patents

Dye solution or print paste containing chlorinated hydrocarbon with an alcohol ketone dioxane alkanoic acid amide tetramethyl urea or pyridine and polyamide dyeing therewith Download PDF

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Publication number
US3623834A
US3623834A US606553A US3623834DA US3623834A US 3623834 A US3623834 A US 3623834A US 606553 A US606553 A US 606553A US 3623834D A US3623834D A US 3623834DA US 3623834 A US3623834 A US 3623834A
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United States
Prior art keywords
pyridine
polyamide
dyeing
tetramethyl urea
dyestuffs
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Expired - Lifetime
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US606553A
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English (en)
Inventor
Marcel Seuret
Willi Leutenegger
Hans E Wegmuller
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Novartis AG
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Ciba Geigy AG
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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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons

Definitions

  • the present invention concerns a process for the continuous dyeing and printing of synthetic polyamide fibre material, the dye liquor used for this purpose and also the fibre material dyed or printed by this process.
  • synthetic polyamide fibre material is dyed both from an aqueous solution with water soluble dyestuffs and from an aqueous dispersion with dispersion dyestuffs, the dyeing being performed either at the boiling point of the Water or at temperatures of 100 to 130 C. under pressure.
  • These dyeing processes often lead to uneven (stripy) dyeings, particularly if texturized synthetic polyamide, Banlon, is used as fibre material and heavy metal containing dyestuffs are used as dyestuffs.
  • synthetic polyamide fibre material can be continuously dyed or printed in level deep and fast shades without an after-treatment.
  • the new process comprises impregnating or printing the material with a solution of at least one dyestuff in a solvent mixture consisting of ice (a) 50 to 99% by weight of unsubstituted or preferably halogenated hydrocarbon which boils between 50 and 150 C., the balance consisting of (b) a liquid, water soluble organic solvent boiling below 220 C. and,
  • these mixtures of solvents contain 50 to 99% by weight of halogenated, particularly chlorinated, hydrocarbons, e.g. chlorobenzene; however, in view of their generally easy recovery and incombustibility, chiefly, low aliphatic halogen hydrocarbons, such as chlorinated hydrocarbons, e.g. chloroform, carbon tetrachloride, trior tetra-chlorethylene (perchlorethylene), tetrachlorethane or dibromomethylene.
  • halogenated, particularly chlorinated, hydrocarbons e.g. chlorobenzene
  • low aliphatic halogen hydrocarbons such as chlorinated hydrocarbons, e.g. chloroform, carbon tetrachloride, trior tetra-chlorethylene (perchlorethylene), tetrachlorethane or dibromomethylene.
  • mixtures of such solvents can form the water insoluble component of mixtures of solvents usable according to the
  • thermostable solvents of which not only fractions of percentages are soluble in water but which are soluble up to several percentages in water.
  • alkanols such as butanols or 'amyl alcohols
  • cycloaliphatic alcohols e.g. cycloalkanols such as cyclohexanol
  • araliphatic alcohols e.g. aralkanols
  • benzyl alcohol or aliphatic
  • cycloaliphatic ketones e.g. alkanones and cycloalkanones such as methylethyl ketone or cyclohexanone.
  • organic solvents as defined which are miscible with water in any ratio are preferred.
  • examples thereof are: low monovalent aliphatic alcohols such as low alkanols, e.g. methanol, ethanol, nor iso-propanol, alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, also furfuryl or tetrahydrofurfuryl alcohol, or divalent aliphatic alcohols e.g.
  • alkanediols such as ethylene glycol or 1,2-propylene glycol
  • low aliphatic ketones such as acetone, low cyclic ethers such as dioxane, also N,N-dialkyl amides of low monocarboxylic acids such as dimethyl formamide or dimethyl acetamide, amides of carbonic acid such as N,N,N',N- tetramethyl urea, or tertiary organic amines such as pyridine, as well as mixtures of such liquid organic solvents which are soluble in water.
  • composition of the mixture of solvents depends on the solubility of the dyestuff or mixture of dyestuffs to be used. It should be so composed that it is in the form of a homogeneous and clear dyestufi solution.
  • Preferred mixtures of solvents are those which consist of to 99% by weight of chlorinated low aliphatic hydrocarbon boiling between 50 and 150 C. the balance consisting of an organic solvent boiling below 220 C. and which is miscible with water in any ratio.
  • a mixture consisting of by weight of trior per-chlorethylene and 10% by weight of a low alkanol, or a N,N-dialkyl amide of a low monocarboxylic acid, particularly a mixture of 90% by weight of trior per-chlorethylene and 10% by weight of methanol or dimethyl formamide has proved to be especially valuable.
  • Dyestuffs usable according to the invention are chiefly dispersion dyestuffs and water soluble dyestuffs. These are, in particular, azo, anthraquinone, nitro, methine, styryl, naphthoperinone, quinophthalone or 5-amino-8- hydroxy-1,4-naphthoquinone-imine dyestuffs.
  • water soluble dyestuffs are meant, patricularly, the so-called acid wool dyestuffs of the azo and anthraquinone 3 series.
  • Preferred azo dyestuffs are monoazo or disazo dyestuffs.
  • heavy metal containing azo dyestuffs such as those containing chromium or cobalt, preferably metallised monoazo dyestuffs free from acid and basic water solubilising groups, which dyestuffs contain one metal atom bound to two molecules of azo dyestuff are suitable dyestuffs in the process of the invention.
  • anthraquinone dyestuffs l-arnino- 4-arylamino-anthraquinone-Z-sulphonic acids are mentioned in particular as anthraquinone dyestuffs.
  • the dyestuff solution to be used according to the invention preferably contains 0.1 to by weight of one or more of the dyestuffs mentioned, depending on the desired depth of shade.
  • the dye solution usable according to the invention can also contain thickeners, advantageously those which are soluble in the mixture of solvents defined, e.g. thickeners having cellulose ester, polyvinyl ester or polyvinyl alcohol as base.
  • thickeners are added in sufiicient amounts to raise the viscosity of the resulting dye liquor or paste to at least 30 centipoises.
  • the fibre material defined is impregnated, for example, by printing or spraying, preferably however, by pad dyeing in the foulard.
  • the fibre material is advantageously passed continuously through the dyestutf solution at room temperature and then squeezed out to the desired content of impregnation solution, which is about 30 to 150% by weight (calculated on the dry weight of the goods).
  • the main part of the mixture of solvents remaining in the fibre material can then be removed, advantageously under mild conditions at 4080 C., particularly in a warm, dry airstream.
  • the dyestuif is fixed on the still wet or already dry fibre material wherefrom excess dye liquor has been removed by steaming or by a dry heat treatment below the softening point of the fibre material.
  • a dry heat fixing contact heat
  • a treatment with high frequency alternating currents or irradiation with infrared rays are suitable; however, the dyestutf is preferably dry fixed on the fibre material in a hot airstream at about 145 to about 230 C., particularly at a temperature of 150 to about 210 C., optimally at 170 to 210 C.
  • Dyestutf Level strongly coloured dyeings which are fast, e.g. to dry cleaning, washing in water or alkaline media, perspiration and rubbing, are obtained on the fibre material mentioned by the process according to the invention without any after-treatment, such as rinsing in water or organic solvents.
  • a further advantage of the process according to the invention over previously known processes is that the solvents used can be regained and again used in the dyeing process so that the problem of cleansing waste water does not arise. In addition, rinsing baths are not necessary.
  • dispersion dyestuffs are used
  • another advantage of the new process over previously known dyeing methods is that dyestuffs as they are obtained technically can be used direct for the production of the dyestuff solutions as defined.
  • the fibre material is impregnated in the cold which is an advance in the state of the art over similar known processes in which the impregnation is performed while heating.
  • EXAMPLE 1 5 g. of the dyestufi of the formula CH CH OH are dissolved in a mixture of solvents consisting of 900 g. of trichloroethylene and 100 g. of methanol. Fabric made from polyamide 6.6-filament is impregnated with this clear red dye solution at room temperature, the impregnated fabric is squeezed out to a liquor content of about calculated on the dry weight of the goods, and then dried at 40-80 in an airstream. The dried dyeing is then thermofixed for seconds at 210.
  • N N-H g-CH; Ho 01 H; N
  • a fabric made from polyamide 6.6 is impregnated with this solution as described in Example 1, the liquor content being about g. of benzyl alcohol the same amount of ethanol or methylethyl ketone is used and otherwise the procedure given in this example is followed, then also strongly coloured, well developed, red dyeings having good fastness properties are obtained.
  • EXAMPLE 14 6 g. of the dyestulf of the formula are dissolved in a mixture of solvents of 900 g. trichlorethylene and 100 g. of dimethyl formamide. Fabric made from polyamide 6.6 is impregnated with this clear, ruby red dye solution as described in Example 1. The liquor content is about 80% calculated on the dry weight of the fabric. Without intermediate drying the dyeing is then thermofixed for 3 minutes in a hot airstream at 180.
  • EXAMPLE 16 4 g. of the dyestuff of the formula are dissolved in a mixture of solvents of 970 g. of trichlorethylene and 30 g. of dimethyl acet-am'ide. A fabric made from polyamide 6.6-filament is impregnated with this solution and dried as described in Example 1. The dyeing is then thermofixed for 2 minutes at 200 in a hot airstream.
  • EXAMPLE 17 5 g. of the 1:2 chromium complex of the compound are dissolved in a mixture of 900 g. of trichlorethylene and g. of methanol. Texturized synthetic polyamide fabric is impregnated with the clear, dark red coloured solution, the impregnated fabric is squeezed out to 100% liquor content (calculated on the dry weight of the goods) and dried at 6080 in an airstream. The dyestufi is thermofixed for 3 minutes in a hot airstream at 200.
  • a dyeing of equal quality is obtained if, in this example, the impregnated and dried texturized synthetic polyamide fabric is steamed for 20 minutes at 100 instead of being thermofixed.
  • a process for the continuous, non-aqueous dyeing or printing of synthetic polyamide fiber material consisting essentially of the steps of:
  • the watersoluble organic solvent is selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, butanols, pentanols, cyclohexanol, benzyl alcohol, acetone, methylethyl ketone, cyclohexanone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, furfuryl alcohol, tctrahydrofurfuryl alcohol, ethylene glycol, 1,2-propylene glycol, dioxane, dimethyl forrnarnide, dimethyl acetamide, zN,N,N',N'-tetramethyl urea, pyridine and mixtures of such solvents which are water soluble.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US606553A 1966-01-05 1967-01-03 Dye solution or print paste containing chlorinated hydrocarbon with an alcohol ketone dioxane alkanoic acid amide tetramethyl urea or pyridine and polyamide dyeing therewith Expired - Lifetime US3623834A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH10266A CH454084A (de) 1966-01-05 1966-01-05 Verfahren zum kontinuierlichen Färben oder Bedrucken von Textilmaterial aus synthetischem Polyamid

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US (1) US3623834A (is")
AT (1) AT273872B (is")
BE (1) BE692183A (is")
CH (1) CH454084A (is")
DE (1) DE1619565A1 (is")
ES (1) ES335268A1 (is")
FR (1) FR1507460A (is")
GB (1) GB1153221A (is")
NL (1) NL6700129A (is")

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3785767A (en) * 1969-08-16 1974-01-15 Bayer Ag Process for the continuous dyeing and printing of fibre materials containing ionic groups
US3891388A (en) * 1970-07-10 1975-06-24 Bayer Ag Exhaust process for the dyeing of synthetic fibre materials
US3980427A (en) * 1970-07-10 1976-09-14 Bayer Aktiengesellschaft Exhaust process for the dyeing of synthetic fiber materials
US3989452A (en) * 1969-07-18 1976-11-02 Ciba-Geigy Corporation Stable, concentrated solutions of complex metal compounds of azo dyestuffs
US3998587A (en) * 1975-05-28 1976-12-21 E. I. Du Pont De Nemours And Company Textile treating dispersion concentrate
US4014647A (en) * 1970-07-10 1977-03-29 Bayer Aktiengesellschaft Exhaust process for the dyeing of synthetic fibre materials
US4093415A (en) * 1974-07-12 1978-06-06 Ciba Geigy Ag Transfer printing process for hydrophilic, synthetic fibre material or mixtures of hydrophilic and synthetic fibre material
US4179267A (en) * 1972-07-14 1979-12-18 Ciba-Geigy Corporation Stable, highly concentrated dyestuff solutions miscible with water in any proportion

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE379068B (is") * 1969-04-30 1975-09-22 Stx Groupement D Enteret Econo
FR2054430A1 (en) * 1969-04-30 1971-04-23 Gillet Thaon Sa Anhydrous basic dyeing medium for fibres - and textiles
BE754665A (fr) * 1969-08-13 1971-01-18 Bayer Ag Procede de teinture et d'impression en continu de matieres fibreuses enpolyamides synthetiques
FR2064365B1 (is") * 1969-10-16 1974-03-22 Ciba Geigy Ag
DE2035728A1 (de) * 1970-07-18 1972-01-27 Farbenfabriken Bayer Ag, 5090 Leverkusen Verfahren zum Färben von synthetischen Fasermaterialien mit Chinophthalonfarbstoffen aus organischen Lösungsmitteln
DE2238398C3 (de) * 1972-08-04 1975-04-10 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Verfahren zum kontinuierlichen Färben von synthetischen Fasermaterialien aus organischen Lösemitteln
US4131424A (en) * 1977-07-21 1978-12-26 Milliken Research Corporation Method of dyeing using the combination of certain halogenated hydrocarbons and aromatic solvents in an aqueous dye admixture

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989452A (en) * 1969-07-18 1976-11-02 Ciba-Geigy Corporation Stable, concentrated solutions of complex metal compounds of azo dyestuffs
US3785767A (en) * 1969-08-16 1974-01-15 Bayer Ag Process for the continuous dyeing and printing of fibre materials containing ionic groups
US3891388A (en) * 1970-07-10 1975-06-24 Bayer Ag Exhaust process for the dyeing of synthetic fibre materials
US3980427A (en) * 1970-07-10 1976-09-14 Bayer Aktiengesellschaft Exhaust process for the dyeing of synthetic fiber materials
US4014647A (en) * 1970-07-10 1977-03-29 Bayer Aktiengesellschaft Exhaust process for the dyeing of synthetic fibre materials
US4179267A (en) * 1972-07-14 1979-12-18 Ciba-Geigy Corporation Stable, highly concentrated dyestuff solutions miscible with water in any proportion
US4093415A (en) * 1974-07-12 1978-06-06 Ciba Geigy Ag Transfer printing process for hydrophilic, synthetic fibre material or mixtures of hydrophilic and synthetic fibre material
US3998587A (en) * 1975-05-28 1976-12-21 E. I. Du Pont De Nemours And Company Textile treating dispersion concentrate

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GB1153221A (en) 1969-05-29
DE1619565A1 (de) 1970-10-01
FR1507460A (fr) 1967-12-29
AT273872B (de) 1969-08-25
CH454084A (de) 1967-12-29
BE692183A (is") 1967-07-04
NL6700129A (is") 1967-07-06
ES335268A1 (es) 1968-04-01

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