US3630663A - Process for dyeing anionic modified synthetic fibers in dye baths containing an organic nitrogen compound - Google Patents

Process for dyeing anionic modified synthetic fibers in dye baths containing an organic nitrogen compound Download PDF

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US3630663A
US3630663A US798812A US3630663DA US3630663A US 3630663 A US3630663 A US 3630663A US 798812 A US798812 A US 798812A US 3630663D A US3630663D A US 3630663DA US 3630663 A US3630663 A US 3630663A
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parts
acid
hydrocarbon chloride
dyeing
amine
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Dietrich Hildebrand
Gunter Briedbach
Helmut Kirschnek
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Bayer AG
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Bayer AG
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Priority claimed from DE19681815417 external-priority patent/DE1815417B2/de
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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
    • 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
    • D06P1/924—Halogenated 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
    • D06P1/44—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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups

Definitions

  • Synthetic fibers containing anionic groups e.g. polyacrylonitrile modified with sulfonic acid groups, are dyed by exhaustion in a dyebath comprising:
  • an organic nitrogen compound containing at least 12 carbon atoms e.g. a fatty amine such as dodecylamine.
  • This invention relates to the dyeing of fiber materials and more particularly to the dyeing of anionic groups containing synthetic fiber materials from hydrocarbon chloride solutions containing the dyestuffs in the form of hydrocarbon chloride soluble dye bases or hydrocarbon chloride soluble salts or adducts of the dye bases, furthermore amines, amides and/or amine oxides containing at least 12 carbon atoms and 0.1 to 4 percent by weight of water.
  • hydrocarbon chlorides used in the process according to the invention are especially those whose boiling point lies between 40 and 150 C., for example aliphatic hydrocarbon chlorides such as methylene chloride, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,1-
  • Tetrachloroethylene, trichloroethylene and l l ,1 trichloropropane have proved to be especially satisfactory.
  • Amines, amides or amine oxides having at least 12 carbon atoms, employed in the process according to the invention include the following: unsubstituted and substituted aliphatic, araliphatic, aromatic, heterocyclic and cyclic mono and polyamines, e.g., fatty amines such as dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, octadecenylamine, as well as ethoxylation and propoxylation products thereof, technical mixtures of fatty amines such as coco fat amine, sperm oil fat amine as well as ethoxylation and propoxylation products thereof; also: N,N-dimethyl-N-dodecylamine, N,N-dimethyl-N-hexadecylamine, N,N-dimethyl-N-octadecenylamine, Octadecyl hydrazine,
  • amine oxides which in addition to an amine oxide group or in addition to a plurality of amine oxide groups also contain polyglycol ether groups, e.g.:
  • N-monoxides the reaction products of moles ethylene oxide and 1 mole stearylamine and N,N'-dioxides of the reaction products of 5-20 moles ethylene oxide and 1 mole 9-aminostearylamine or 9-(amino-methyl)stearylamine; also the amine oxides that in addition to one or more amine oxide groups also contain one or more basic nitrogen atoms, e.g.,
  • N-methyl-N-octadecyl-N-[3-(gamma-aminopropylamino)- propyl]-amino oxide N-methyl-N-octadecyl-N-[3-(gamma-aminopropylamino)- propyl]-amino oxide; and those amine oxides that are obtainable if in the compounds listed above that contain a plurality of tertiary amino groups, e.g., in condensation products, copolymers, polyureas, polyurethanes, conversion products and reaction products, only a part of the tertiary amino groups are converted to amino oxide groups.
  • Basic dyes applicable in the process according to the invention are all dyes that contain at least one basic nitrogen atom. They can belong to the most multifarious classes-of dyes, e.g., the azo, anthraquinone, azine, oxazine, xanthene, methin, triphenylmethane and phthalocyanine dyes.
  • the dyes must be dissolved in the chlorohydrocarbon solutions either as free dye bases or as salts or adducts of acid esters of inorganic acids or of organic acids.
  • the following anions are employed for the dye salts and dye adducts:
  • acid esters of inorganic acids such as dodecyl sulfate stearyl sulfate oleyl sulfate undecylethylene glycol sulfate oleic acid sulfate oleic acid butyl ester sulfate ricinoleic acid ethyl ester sulfate ricinoleic acid monoethyl glycol ester sulfate oleic acid ethyl amide sulfate oleic acid ethanol amide sulfate oleic acid diethanol amide sulfate oleic acid diisobutyl amide sulfate oleic acid anilide sulfate N-acetyloleyl amino sulfate tetradecyl triglycol ether sulfate hexadecyl diglycol ether sulfate octadecyl
  • the dyes can be added to the hydrocarbon chlorides in the form of free bases or as hydrocarbon chloride soluble dye salts or dye adducts.
  • the hydrocarbon chloride soluble dye salts or dye adducts can however also be produced in the hydrocarbon chlorides from the components, the dye bases and acids, but also by double conversion of dye salts of inorganic acids with salts of organic, acid group containing compounds soluble in hydrocarbon chlorides, e.g., sodium lauryl sulfate, sodium paraffin sulfonate.
  • the dye bases and acids or the dye salts of inorganic acids and the salts of the organic acid group containing compounds soluble in hydrocarbon chlorides are added to the hydrocarbons in such proportion that for each equivalent of the basic dye at least one equivalent of the compounds containing carboxyl, sulfone, sulfate or phosphate groups is present.
  • the amounts in which the dye bases, dye salts or dye adducts are added to the hydrocarbon chloride dyebaths can vary within wide limits depending on the depth of the shade that is desired; in general amounts from 0.1 to 8 percent by weight based on the weight of the material to be dyed have been found satisfactory.
  • the amounts in which the amines, amides or amine oxides to be used in the process according to the invention are added to the dye baths depends on the amounts of basic dye employed. In general, it has been found satisfactory to use amines, amides and/or amine oxides and basic dyes in the proportion of 0.1 to 4:1.
  • the start'was made with the salts of the basic dyes with inorganic acids when larger amounts of the dye salts must be dissolved, to dissolve or disperse the latter in a hydrotropic solvent and add it t the dyebath in this form.
  • a hydrotropic solvent the fol lowing may for example be mentioned: isopropanol, benzyl alcohol, Z-phenoxyethanol, acetonitrile, oxypropionitrile, dimethyl sulfoxide, dimethyl formamide or glycolacetate methyl ether.
  • hydrocarbon chloride dyebaths beside the amines, amides or amine oxides, small amounts of water, for example, 0.14 percent, preferably 0.1-2 percent by weight.
  • lt has been found advantageous for the dispersion of the water also to add emulsifiers to the hydrocarbon chloride solutions in the amount of 0.1-2 percent by weight based on the weight of the hydrocarbon chloride.
  • emulsifiers preferably nonionogenic compounds are employed; oxyethylation products of fatty alcohols, phenols, fatty acid amides and fatty acids as well as mixtures of these.
  • polyamides e.g., polyhexamethylenediamine adipate, polycaprolactam or poly-w-amino-undecanic acid modified by sulfonic acid groups.
  • the dyeing of the anionic groups containing fiber materials from hydrocarbon chloride solutions can for example, be achieved by introducing the fiber material at room temperature into the hydrocarbon chloride dyebaths which contain the basic dyestuffs, their salts or acid adducts, the amines, amides and/or amine oxides, the water and optionally the emulsifiers and hydrotropic solvents; the bath is heated to temperatures from 70 to C. and kept at this temperature until the bath is exhausted. After cooling the bath is separated off and the fiber material are freed from adhering solvent by suction or centrifuging and subsequent drying in an air current.
  • the dyeing process according to the present invention is distinguished over the dyeing process of the Belgian Pat. No. 703,187 by the use of basic dyestuffs soluble in hydrocarbon chloride solutions.
  • dyestuffs are used which are insoluble or only sparingly soluble in hydrocarbon chlorides.
  • dye liquors which are much more stable under the dyeing conditions and which therefore do not yield stains on the textile materials and dyestuffidepositions on the rimps of the dyeing apparatus.
  • the hydrocarbons chloride soluble dyestufi the serious problem of emulsifying aqueous dyestuff solutions in hydrocarbon chloride solutions is avoided. According to the present invention it is possible to prepare the hydrocarbon chloride dye liquors in a simple manner without endangering the personnel.
  • EXAMPLE 1 The bath is heated to l C. within 30 minutes with vigorous circulation and is held for one hour at this temperature. After this period the bath is separated off and the yarn freed in an air stream from adhering solvent. A uniform brownish red coloring is obtained.
  • EXAMPLE 2 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of the reaction product of l mole of the dye of formula I with 1 mole sodium-di-n-butyl-naphthaline sulfonate four parts of oleic acid diethanolamide (technical) four parts of a reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide and eight parts of water in 983 parts of perchloroethylene.
  • Dyeing is carried out as described in example i. A uniform reddish brown coloring is obtained.
  • EXAMPLE 3 Fifty pans of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of the reaction product of 1 mole of the dye of formula l with 1 mole of sodium-4-tetradecylbenzene sulfonate four parts of the condensation product of 4 moles stearic acid polyglycerol ester with 1 mole triethylene tetramine five parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide and parts of water in 980 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A uniform reddish brown coloring is obtained.
  • EXAMPLE 4 Twenty five parts of knit goods of anionic groups containing acrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of the reaction product of 1 mole of the dye of formula l with 1 mole of sodium-4-octadecylbenzene sulfonate four parts of ricinoleic acid amide four parts of a compound of the formula I NIr 7 V 7 llla two parts of glycol methyl ether and eight parts of water in 981 parts of perchloroethylene.
  • Dyeing is carried out as described in Example l. A uniform reddish brown coloring is obtained.
  • EXAMPLE 5 Fifty parts of a knitting yarn of anionically modified polyester are introduced at 22 C. into a dyebath that consists of a mixture of one part of the reaction product of 1 mole of dye of formula VI! with 1 mole of sodium-diisobutylmethyl-naphthalene sulfonate five parts of the reaction product of 1 mole oleic acid oxy benzylamide with moles ethylene oxide five parts of a compound of the fon'nula and 9 parts of water in 980 parts of perchloroethylene.
  • EXAMPLE 6 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath containing a mixture of one part of formula Vlll 0.4 parts of sodium-dodecylbenzene sulfonate four parts of a compound of the formula (Illa Ulla four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide 2 parts of aminoundecanic acid and 8 parts of water in 980 parts of perchloroethylene.
  • Dyeing is carried out as described in example I. A uniform blue-green coloring is obtained.
  • EXAMPLE 7 Fifty parts of a fabric of anionic groups containing acrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula IX 0.4 parts of sodium-4-dodecylbenzene sulfonate four parts of a compound of the formula four parts of the reaction product of 1 mole oleic acid with 7 moles ethylene oxide four parts of a reaction product of 1 mole phenol with 10 moles ethylene oxide and seven parts of water in 980 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A uniform red coloring is obtained.
  • EXAMPLE 8 Fifty parts of knit goods of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath con- 3.6 parts of the reaction product of 1 mole nonyl-phenol with 7 moles ethylene oxide two parts of the reaction product of 1 mole oleic acid with 20 moles ethylene oxide and eight parts of water in 98 1 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A uniform redcoloring is obtained.
  • EXAMPLE 9 Fifty parts of a gauze material of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula XI 0.4 parts of sodium oleic acid ethanol amide sulfate five parts of the reaction product of the 1 mole oleylamine with 18 moles ethylene oxide four parts of N-dodecyl-N-methylol-urea and eight parts of water in 98 1 parts of perchloroethylene.
  • Dyeing is carried out as described in example i A uniform yellow coloring is obtained.
  • EXAMPLE l EXAMPLE 1 l Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile (Dralon) are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula VIII 0.4 parts sodium oleic acid butyl ester sulfate four parts of the amine oxide of the formula four parts of the reaction product of moles ethylene oxide on 1 mole oleyl alcohol and 6 parts of water in 984 parts of perchloroethylene.
  • a dyebath consisting of a mixture of one part of dye of formula VIII 0.4 parts sodium oleic acid butyl ester sulfate four parts of the amine oxide of the formula four parts of the reaction product of moles ethylene oxide on 1 mole oleyl alcohol and 6 parts of water in 984 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A clear blue-green coloring is obtained.
  • EXAMPLE l2 Fifty pans of a fiber yarn of anionically modified polyester (Dacron 64) are introduced at 22 C. into a dyebath consisting of a mixture of 1.5 parts of the dye of formula I 0.7 parts of sodium-N-acetyloleyl amino sulfate six parts of the amino oxide of the formula 1.9 six parts of the compound of the formula and 8 parts of water in 984 parts of perchloroethylene.
  • Dyeing is carried out as in example 1. A saturated deep reddish brown coloring is obtained.
  • EXAMPLE l3 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of 1.5 parts of the dye of formula II 0.7 parts of sodium hexadecyldiglycol ether sulfate 4.5 parts of the amine oxide of the formula LII CIIr-CIIr'OII five parts of the reaction product of 1 mole oleic acid with 19 moles ethylene oxide and 4 parts of water 7 in 980 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A uniform blue coloring is obtained.
  • EXAMPLE l4 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a-dyebath con sisting of a mixture of one part of the dye of formula III 0.5 parts of the sodium-4-tetradecylbenzene sulfonate four parts of the amino oxide of the formula four parts of the reaction product of 20 moles ethylene oxide and 1 mole oleyl alcohol and 8 parts of water in 982 parts of perchloroethylene.
  • Dyeing is carried out as described in example I A uniform wine red coloring is obtained.
  • EXAMPLE l5 Fifty parts of a fiber yarn of anionically modified polyamide are introduced at 22 C. into a dyebath consisting of a mixture of one part of the dye of formula IV 0.5 parts of sodium dodecylbenzene sulfonate four parts of the amino oxide of the formula (II on. (0112). on. N f
  • Dyeing is carried out as described in example I. A uniform blue coloring is obtained.
  • EXAMPLE l6 Fifly parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula Vlll 0.5 parts of sodium lauryl sulfate four parts of the amino oxide of the formula four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 7 moles ethylene oxide and 9 parts of water in 980 parts of l ,l, l -trichloropropane.
  • a dyebath consisting of a mixture of one part of dye of formula Vlll 0.5 parts of sodium lauryl sulfate four parts of the amino oxide of the formula four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 7 moles ethylene oxide and 9 parts of water in 980 parts of l ,l, l
  • Dyeing is carried out as described in example 1. A greenish blue coloring is obtained.
  • EXAMPLE l7 Fifty parts of a fiber yarn of anionic groups containing acrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula XIll 0.2 parts of sodium dodecylbenzene sulfonate four parts of the amino oxide of the formula four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 7 moles ethylene oxide and 9 parts of water in 980 parts of 1,1,1-trichloropropane.
  • a dyebath consisting of a mixture of one part of dye of formula XIll 0.2 parts of sodium dodecylbenzene sulfonate four parts of the amino oxide of the formula four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 7 moles ethylene oxide and 9 parts of water in 980 parts of 1,
  • Dyeing is carried out as described in example 1. A brilliant green coloring is obtained.
  • EXAMPLE l8 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula X 0.2 parts of ammonium oleyl sulfate four parts of the amino oxide of the formula N-ClIg four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 7 moles ethylene oxide and 9 parts of water in 980 parts of l,l,l-trichloropropane.
  • Dyeing is carried out as described in example 1. A uniform yellow coloring is obtained.
  • EXAMPLE 20 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula XII 0.2 parts of sodium-paraffin sulfonate four parts of the N-oxide of the formula EXAMPLE 21 Fifty parts of a fiber yarn of anionically modified polyamide are introduced at 22 C.
  • EXAMPLE 22 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of one part of the dye of formula i 0.5 parts of sodium lauryl sulfate two parts of glacial acetic acid three partsof the compound of the formula 2 parts of the compound of the formula five parts of water in 986.5 parts of perchloroethylene.
  • Dyeing is carried out as in example 1. A saturated reddish brown coloring is obtained.
  • EXAMPLE 23 Thirty parts of knit goods of anionically modified polyamide (Nylon T 844) are introduced at 22 C. into a dyebath consisting of a mixture of one part of the dye of formula Ill 0.5 parts of sodium lauryl sulfate one part of glacial acetic acid four parts of dodecyl aniline two parts of the reaction product of 1 mole oleic acid with 7 moles ethylene oxide two parts of the reaction product of 1 mole nonylphenol with 10 moles ethylene oxide two parts of the reaction product of l mole oleyl alcohol with 20 moles ethylene oxide and eight parts of water in 980 parts of perchloroethylene.
  • a dyebath consisting of a mixture of one part of the dye of formula Ill 0.5 parts of sodium lauryl sulfate one part of glacial acetic acid four parts of dodecyl aniline two parts of the reaction product of 1 mole oleic acid with 7 moles ethylene oxide two parts of the reaction product of 1 mo
  • Dyeing is carried out as described in example I. A ruby red coloring is obtained.
  • EXAMPLE 25 Fifty parts of a fiber yarn of anionically modified polyamide are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula X 0.5 parts of sodium-4-dodecylbenzene sulfonate three parts of dodecylaniline three parts of the reaction product of 20 moles ethylene oxide with 1 mole oleyl alcohol and p 8.5 parts ofwater v in 984 parts of perchloroethylene.
  • Dyeing is carried out asdescribed in example 1. A clear pink coloring is obtained.
  • EXAMPLE 26 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula Vlil 0.5 parts of sodium paraffin sulfonate four parts of the reaction product of 1 mole oleylamine with 20 moles ethylene oxide one part of glacial acetic acid and eight parts of water in 986 parts of perchloroethylene.
  • Dyeing is carried out as described in example 1. A clear greenish-blue coloring is obtained.
  • EXAMPLE 27 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of one part of dye of formula XI" 0.4 parts of sodium-Modecylbenzcne sulfonate four parts of stearylamine four parts of the reaction product of 1 mole oleyl 'alcoho with 20 moles ethylene oxide two parts of glacial acetic acid and nine parts of water with 980 parts of perchloroethylene.
  • a dyebath consisting of a mixture of one part of dye of formula XI" 0.4 parts of sodium-Modecylbenzcne sulfonate four parts of stearylamine four parts of the reaction product of 1 mole oleyl 'alcoho with 20 moles ethylene oxide two parts of glacial acetic acid and nine parts of water with 980 parts of perchloroethylene.
  • EXAMPLE 28 Fiftyparts of a fiber yarn of anionically modified polyester are introduced at 22 C. into a dyebath consisting of a mixture of one part of the dye of formula V one part of glacial acetic acid four parts of oleic acid diethanolamide (technical) four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide and eight parts of water in 982 parts of perchloroethylene.
  • the bath is heated with vigorous circulation to 1 10 C. within 30 minutes and held at this temperature for 2 hours.
  • the bath is subsequently separated off and the yarn is freed from adhering solvent in an air current.
  • EXAMPLE 29 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of 0.5 parts of the dye of formula VI four parts of oleic acid diethanolamide (technical) four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide and 8.5 parts of water in 983 parts of perchloroethylene.
  • Dyeing is carried out as described in example i. A brilliant deep blue coloring is obtained.
  • EXAMPLE 30 Fifty parts of a fiber yarn of anionic groups containing polyacrylonitrile are introduced at 22 C. into a dyebath consisting of a mixture of 0.5 parts of dye of formula XVI 0.5 parts of oleic acid four parts of oleic acid diethanol amide four parts of the reaction product of 1 mole oleyl alcohol with 20 moles ethylene oxide and eight parts of water in 983 parts of perchloroethylene.
  • a process for dyeing anionic group containing fiber materials selected from the group consisting of polyesters, polyamides and polyacrylonitrile which comprises dyeing said ((JII3)Z'N"AV' c -q *N 75 fiber materials by exhaustion in a dyeing bath comprising A. a hydrocarbon chloride solvent;
  • an organic nitrogen compound selected from the group consisting of an amine, an amide, an amine oxide, and mixtures thereof, said amine, amide and amine oxide having at least 12 carbon atoms.
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble dye salt with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble adduct with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.
  • a process for dyeing anionic group containing fiber materials selected from the group consisting of polyesters, polyamides and polyacrylonitrile which comprises dyeing said fiber materials by exhaustion in a dyeing bath comprising A. a hydrocarbon chloride solvent;
  • an organic nitrogen compound selected from the group consisting of an amine, an amide, an amine oxide, and mixtures thereof, said amine, amide and amine oxide having at least 12 carbon atoms;
  • E 0.1 to 2 percent by weight, based on the hydrocarbon chloride solvent of an emulsifier.
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble dye salt with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble adduct with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.
  • an organic nitrogen compound selected from the group consisting of an amine, an amide, an amine oxide, and mixtures thereof, said amine, amide, and amine oxide having at least 12 carbon atoms;
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble dye salt with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.
  • hydrocarbon chloride soluble basic dyestuff being present in the form of a hydrocarbon chloride soluble adduct with an acid selected from the group consisting of an organic acid and an acid ester of an inorganic acid.

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US798812A 1968-08-30 1969-02-12 Process for dyeing anionic modified synthetic fibers in dye baths containing an organic nitrogen compound Expired - Lifetime US3630663A (en)

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Application Number Priority Date Filing Date Title
DE19681794049 DE1794049A1 (de) 1968-08-30 1968-08-30 Verfahren zum Faerben von Fasermaterialien aus anionisch modifiziertem Polyacrylnitril
DE19681815417 DE1815417B2 (de) 1968-12-18 1968-12-18 Verfahren zum faerben von anionisch modifizierten, synthetischen fasermaterialien

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AT (1) AT291917B (enrdf_load_stackoverflow)
BE (1) BE738244A (enrdf_load_stackoverflow)
CH (2) CH531090A (enrdf_load_stackoverflow)
FR (1) FR2017111B1 (enrdf_load_stackoverflow)
GB (1) GB1234727A (enrdf_load_stackoverflow)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925012A (en) * 1968-08-02 1975-12-09 Bayer Ag Process for dyeing fibre material containing nh-groups from organic solvents
US3954399A (en) * 1972-03-28 1976-05-04 Sumitomo Chemical Company, Limited Process for dyeing nitrogen-containing fibers
US4042322A (en) * 1971-10-23 1977-08-16 Bayer Aktiengesellschaft Process for dyeing anionically modified synthetic fiber materials

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE754886A (fr) * 1969-08-16 1971-01-18 Bayer Ag Procede de teinture et d'impression en continu de matieres fibreuses contenant des groupes ioniques
US3843322A (en) * 1970-12-21 1974-10-22 Gaf Corp Dyestuff solution for acrylic fibers

Citations (5)

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US3097047A (en) * 1961-04-27 1963-07-09 Tanatex Chemical Corp Dyeing synthetic fibers with alkyl naphthalene composition
GB981547A (en) * 1962-03-29 1965-01-27 Basf Ag Stable highly concentrated solutions of basic dyes
CH425718A (fr) * 1963-01-31 1967-06-15 Warwick Chemical Yorkshire Lim Procédé pour apprêter des fibres textiles
BE703187A (enrdf_load_stackoverflow) * 1966-09-01 1968-02-28
US3510243A (en) * 1965-12-09 1970-05-05 Geigy Ag J R Process for the continuous dyeing and printing of fibre material from linear,high molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097047A (en) * 1961-04-27 1963-07-09 Tanatex Chemical Corp Dyeing synthetic fibers with alkyl naphthalene composition
GB981547A (en) * 1962-03-29 1965-01-27 Basf Ag Stable highly concentrated solutions of basic dyes
CH425718A (fr) * 1963-01-31 1967-06-15 Warwick Chemical Yorkshire Lim Procédé pour apprêter des fibres textiles
US3510243A (en) * 1965-12-09 1970-05-05 Geigy Ag J R Process for the continuous dyeing and printing of fibre material from linear,high molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols
BE703187A (enrdf_load_stackoverflow) * 1966-09-01 1968-02-28
GB1192984A (en) * 1966-09-01 1970-05-28 Bayer Ag Improved Process for Dyeing Fibrous Material

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925012A (en) * 1968-08-02 1975-12-09 Bayer Ag Process for dyeing fibre material containing nh-groups from organic solvents
US4042322A (en) * 1971-10-23 1977-08-16 Bayer Aktiengesellschaft Process for dyeing anionically modified synthetic fiber materials
US3954399A (en) * 1972-03-28 1976-05-04 Sumitomo Chemical Company, Limited Process for dyeing nitrogen-containing fibers

Also Published As

Publication number Publication date
NL6913172A (enrdf_load_stackoverflow) 1970-03-03
CH531090A (de) 1972-06-30
GB1234727A (en) 1971-06-09
FR2017111B1 (enrdf_load_stackoverflow) 1974-09-20
FR2017111A1 (enrdf_load_stackoverflow) 1970-05-15
AT291917B (de) 1971-08-10
CH1316769A4 (enrdf_load_stackoverflow) 1972-06-30
BE738244A (enrdf_load_stackoverflow) 1970-03-02

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