US3785767A - Process for the continuous dyeing and printing of fibre materials containing ionic groups - Google Patents

Process for the continuous dyeing and printing of fibre materials containing ionic groups Download PDF

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Publication number
US3785767A
US3785767A US00062651A US3785767DA US3785767A US 3785767 A US3785767 A US 3785767A US 00062651 A US00062651 A US 00062651A US 3785767D A US3785767D A US 3785767DA US 3785767 A US3785767 A US 3785767A
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Prior art keywords
chlorinated hydrocarbon
hydrocarbon solvent
parts
fiber material
fibre materials
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Expired - Lifetime
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US00062651A
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English (en)
Inventor
D Hildebrand
R Kuth
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Bayer AG
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Bayer AG
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Priority claimed from DE19691941698 external-priority patent/DE1941698C3/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—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
    • D06P1/90—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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/938—Solvent dyes

Definitions

  • the invention relates to a pad-steaming process for the continuous dyeing and printing of fibre materials containing ionic groups, from organic solvents; the process is characterised in that the fibre materials are dyed or printed with chlorinated hydrocarbon dyebaths containing ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compounds.
  • Chlorinated hydrocarbons suitable for the process according to the invention are primarily the chlorinated hydrocarbons the boiling points of which lie between 40 and 170C, e.g. aliphatic chlorinated hydrocarbons such as methylene chloride, chloroform, car- .bon tetrachloride l l -dichloroethane, 1 ,2- dichloroethane, l,l ,l-trichloroethane, 1,1,2- trichloroethane, 1,1 ,l ,2-tetrachloroethane, 1,1 ,2,2- tetrachloroethane, pentachloroethane, l-
  • Tetrachloroethylene, trichloroethylene and 1,1,1- trichloropropane have proved particularly satisfactory.
  • the fibre materials containing ionic groups, which are to be dyed according to the invention comprise:
  • These include all natural or synthetic fibre materials which can be dyed with anionic dyestuffs.
  • natural polyamides especially wool and synthetic polyamides, e.g., poly-c-caprolactam, polyhexamethylene-diamine adipate and poly-wamino-undecanic acid;
  • polyesters modified by carboxyl and/or sulphonic acid groups such as polyethylene terephthalate, polycyclohexanedimethylene terephthalate; heterogeneous polyesters obtained from terephthalic acid, isophthalic acid and ethylene glycol or from terephthalic acid, sulphoisophthalic acid and ethylene glycol; furthermore, copolyether ester fibres obtained from phydroxybenzoic acid, terephthalic acid and ethylene glycol; or polyamides modified by sulphonic acid groups, such as polyhexamethylene adipate, polycaprolactam of poly-w-aminoundecanic acid.
  • anionic groups such as sulphonic acid, sulphimide, carboxyl and- /or phosphonic acid groups
  • polyesters modified by carboxyl and/or sulphonic acid groups such as polyethylene terephthalate, polycyclohexanedimethylene terephthalate
  • the ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compensating ions and serve in the process according to the invention for the dyeing of fibre materials containing cationic groups comprise chlorinated hydrocarbon-soluble amine salts and amine addition products of dyestuffs containing 1 to 4 carboxyl and/or sulphonic acid groups.
  • the dyestuffs containing 1 to 4 sulphonic acid groups from which the amine salts or amine addition products soluble in chlorinated hydrocarbons are derived may belong to a variety of dyestuff classes, for example, to
  • dyestuffs may also contain reactive groups.
  • Suitable amines on which the amine salts or amine addition products soluble in chlorinated hydrocarbons are based are primary, secondary and tertiary monoamines as well as primary, secondary and tertiary polyamines.
  • primary, secondary and tertiary monoamines are: optionally substituted aliphatic amines, such as tri-n-propylamine, 2-ethyl-hexylamine, dodecylamine, dodecylamine polyglycol ether with 20 mol ethylene oxide, hexadecylamine, hexadecylamine polyglycol ether with 20 mol ethylene oxide, octadecylamine,
  • N-methyl-octadecylamine N-methyl-octadecylamine polyglycol other with 10 mol ethylene oxide
  • fatty amines such as coconut fatty amine and sperm oil fatty amines and their ethoxylation and propoxylation products
  • optionally substituted cycloaliphatic amines such as N,N-dimethyl-cyclohexylamine, N-ethyl-cyclohexylamine, N-2-hydroxyethyl-cyclohexylamine, N,N-bis-(2-hydroxyethyl)-cyclohexylamine, N,N-bis-(2-chloroethyl)-cyclohexylamine, l-cyclohexylamino-propanol-Z, l-cyclohexylamino-propylamine-3 and dicyclohexylamine;
  • araliphatic amines such as benzylamine, N,N-dimethyl-benzylamine, N,N-dibenzylamine, N-methyl-N,N-dibenzylamine,
  • aromatic amines such as N-ethyl-aniline
  • Examples of primary, secondary and tertiary polyamines are primarily aliphatic polyamines, such as N-dodecyl-N',N'-dimethyl-ethylene-diamine, N-dodecyl-N',N-diethyl-ethylene-diamine, N-octadecyl-N',N'-diethyl-ethylene-diamine, N-phenyl-N,N'-dimethyl-ethylene-diamine, N-oleyl-N,N'-dimethyl-ethylene-diamine, N-oleyl-N',N'-diethyl-ethylene-diamine, N-dodecyl-N',N '-dimethyl-propylene-diamine-(1,3), N-dodecyl-N',N'-diethyl-propylene-diamine-( l ,3), N-oleyl-N ,N '-dimethyl-
  • lf acidic dyestuffs containing reactive groups are used, obviously, only those amines are suitable for the formation of salts or addition products, which contain no free NH-group.
  • Ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compounds and serve in the process according to the invention for the dyeing 6 of fibre materials containing anionic groups comprise all cationic dyestuffs which contain at least one cationic nitrogen atom and the anion of an acid which forms a salt soluble in chlorinated hydrocarbons with the cationic dyestuff.
  • the cationic dyestuffs from which the dyestuff salts to be used according to the invention, which contain at least one cationic nitrogen atom and are soluble in chlorinated hydrocarbons are derived may belong to a variety of dyestuff classes, for example, to the azo, anthraquinone, azine, oxazine, xanthene, methine, triphenyl-methane and phthalocyanine dyestuffs.
  • the dyestuffs include optical brightening agents, e.g. optical brightening agents from the stilbehe, couinarin, azole, and naphthalimide series.
  • Anions suitable for the dyestuff salts are: anions of acidic esters of inorganic acids, such as the dodecyl sulphate, I stearyl sulphate, oleyl sulphate, oleic acid sulphate, oleic acid butyl ester sulphate, ricinoleic acid ethyl ester sulphate, ricinoleic acid monoethyl glycol ester sulphate, oleic acid ethylamide sulphate, oleic acid ethanolamide sulphate, oleic acid diethanolamide sulphate, oleic acid diisobutylamide sulphate, oleic acid anilicle sulphate,
  • acidic esters of inorganic acids such as the dodecyl sulphate, I stearyl sulphate, oleyl sulphate, oleic acid sulphate, oleic acid but
  • N-acetyloleylamine sulphate undecylethylene glycol ether sulphate, tetradecyltriglycol ether sulphate, hexadecyldiglycol ether sulphate, octadecylpentaglycol ether sulphate, N-oleyl-4-aminobutano-Z-sulphate ions and anions of organic acids, such as oleic acid-N-dimethylamide sulphonate,
  • the amounts in which the dyestuff amine salts or addition products or the salts of dyestuff bases with aliphatic or aromatic carboxylicor sulphonic acids to be used according to the invention are added to the chlorinated hydrocarbon paddingliquors may vary within wide limits, dependent upon the desired depth of colour; in general, amounts of 5 gm 30 g in 1000 g of padding liquor have proved satisfactory.
  • Suitable thickening emulsifiers are commercial non-ionic, anion-active, cation-active or zwitterionic emulsifiers, for example, oleic acid ethanolamide, oleyl alcohol eicosaglycol ether, nonylphenol heptaglycol ether, nonylphenol decaglycol ether, dodecylbenzene sulphonate, stearyl alcohol sulphate, N,N-dimethyl-N-benzyl-N-oleyl ammonium chloride and N,N-dimethyl-N-hexadecyl-N-(2-hydroxy-3- sulpho)-propylbetaine.
  • oleic acid ethanolamide for example, oleyl alcohol eicosaglycol ether, nonylphenol heptaglycol ether, nonylphenol decaglycol ether, dodecylbenzene sulphonate, stearyl alcohol
  • the chlorinated hydrocarbon dyebaths may contain auxiliaries which further the fixing of the dyestuff and/or improve the quality of the dyeing, for example, the levelness.
  • auxiliaries which have proved satisfactory are, for example, interface-active compounds which are soluble in chlorinated hydrocarbons, such as alkylbenzene sulphonates, fatty alcohol sulphates, ethoxylation products of fatty alcohols, alkylphenols, fatty amines, fatty acid amides and fatty acids; furthermore, fatty acid ethanolamides, fatty amine oxides, fatty acid amideamine oxides, as well as mixtures thereof.
  • the quantities in which the auxiliaries are added to the dyebath amount to 0 4%, preferably 0.5 2%, referred to the fibre material to be dyed.
  • the dyebaths may contain 0.1 2 per cent by weight, referred to the weight of the chlorinated hydrocarbons, of a lower carboxylic acid, suchas formic acid or acetic acid.
  • the process according to the invention is advantageously carried out by spraying or impregnating the fibre materials with the chlorinated hydrocarbon liquors, squeezing to a liquor absorption of 60 160%, and then treating them, optionally after an intermediate drying, with saturated steam or overheated steam at 100 200C.
  • the fibre materials are subsequently rinsed with chlorinated hydrocarbons, in order to remove the non-fixed dyestuff, and subsequently dried by blowing with hot air.
  • the dyestuffs soluble in chlorinated hydrocarbons can be added to the chlorinated hydrocarbons liquors in undissolved form. However, it has also proved satisfactory to add them to the chlorinated hydrocarbons in the form of concentrated, e.g., 25 50%, solutions in chlorinated hydrocarbons or in organic solvents of unlimited miscibility with the latter, such as dimethyl formamide, isopropanol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, benzyl alcohol or butyrolactone.
  • the process according to the invention in which dyestuffs soluble in chlorinated hydrocarbons are used is superior in that it yields stronger and more brilliant dyeing and prints, since the good solubility of the dyestuffs to be used according to the invention, in chlorinated hydrocarbons even without the addition of solubilizers enables stable single-phase padding liquors of high dyestuff concentrations to be prepared.
  • the use of dyestuffs soluble in chlorinated hydrocarbons according to the invention makes it pos- ,sible to rinse the fibre materials with chlorinated hydrocarbons so that the whole dyeing process can be carried out without the occurrence of waste water.
  • EXAMPLE 1 A wool fabric is padded on a foulard with a thickened padding liquor consisting of 20 parts of the dyestuff of the formula [coconut fatty aminel oas- 2 parts nonylphenol decaglycol ether,
  • EXAMPLE 2 A wool fabric is impregnated with a padding liquor 7 8 consisting of l i 2 parts N,N-dimethyl-N-hexadecyl-N-(2-oxy-3-sul- 20 parts of the dyestuff of the formula pho)-propyl-betaine,
  • the fabric is subsequently rinsed in perchloroeth- CJHNGSO) ylene at 40C for 3 minutes and freed from the adher- 6 parts 1,3-bis-(2-ethyl-hexyl)-glycerol e h ing solvent by blowing with air.
  • a clear brilliant yellow h 20 dyeing is obtained without the occurrence of waste wap ate, 2 parts isononyl phenol heptaglycol ether, 2 parts N,N-dimethyl-N-hexadecyl-N-(2-oxy-3-sulpho)-propyl-betaine, EXAMPLE 4 4 parts benzyl alcohol, 4 A polyacrylonitrile rope is impregnated with a pad- 200 parts water and ding liquor consisting of 756 parts perchloroethylene 20 parts of a dyestuff preparation consisting of with a liquor absorption of 104%, and, without inter- 34 parts f th d t ff f the formula Mfll CHa aim Q [-1 CH3 CH3 H mediate drying, steamed with steam at 103C for 15 8 Parts water minut 32 parts benzyl alcohol an The fabric is subsequently rinsed with a solution at 26 Parts p pf 60C f 1 part glacial acetic acid 2 parts of a
  • nium chloride 17.5 parts oleic acid heptaglycol ether 57.9 parts of water in 45 1600 parts perchloroethylene. After drying, an intense red dyeing is obtained without the occurrence of waste water.
  • EXAMPLE 7 A yarn of p0lyhexamethylene-diamine adipate threads is sprayed in stripes with a dyestuff solution consisting of parts of a dyestuff preparation consisting of 15 parts of the dyestuff of the formula and parts diethylene glycol monobutyl ether in 950 parts trichloroethylene dried and steamed at l03C for 15 minutes. The yarn is subsequently rinsedin trichloroe'thylene at 45C for 5 minutes and then dried by blowing with hot air. A clear yellow unlevel dyeing of good fastness properties is obtained without the occurrence of waste water.
  • EXAMPLE 9 l0 2. The process of claim 1 in which the fiber material A fabric of poly-e-caprolactam is impregnated with a is subjected to an intermediate drying step before the padding liquor consisting of steam treatment step (B).
  • the fabric is subsequently rinsed in tri- 8 amomc groups Selected t Sulflnlc aCld, sulfichloroethylene at room temperature for 4 minutes, ii carboxyl and P acld p p y ers then centrifuged and freed from the adhering solvent wit carboxyl or Sulfomc acld groups; or polyamlde with sulfonic acid groups.
  • Pad steaming process for the continuous dyeing Stuff and printing of fiber material containing ionic groups comprising the steps of A. impregnating said fiber material which is selected from the group consisting of natural polyamides, synthetic polyamides, anionically modified synthetic polyamides, anionically modified polyacrylo- 40 -nitrile and anionically modified polyesters with by blowing with hot air. A strongly and evenly bright- 3O ened white fabric is obtained without the occurrence'of 6.
  • the process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition product (1) and the chlorinated hydrocarbon solvent (2); (3) an auxiliary which improvesthe levelness of the dyeing.
  • organic solvent said organic solvent consisting of The fiber material d by the process of claim a chlorinated hydrocarbon solvent having a boil-

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US00062651A 1969-08-16 1970-08-10 Process for the continuous dyeing and printing of fibre materials containing ionic groups Expired - Lifetime US3785767A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691941698 DE1941698C3 (de) 1969-08-16 Verfahren zum kontinuierlichen Färben und Bedrucken ionische Gruppen enthaltender Fasermaterialien

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US3785767A true US3785767A (en) 1974-01-15

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US00062651A Expired - Lifetime US3785767A (en) 1969-08-16 1970-08-10 Process for the continuous dyeing and printing of fibre materials containing ionic groups

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Country Link
US (1) US3785767A (enrdf_load_stackoverflow)
JP (1) JPS5029074B1 (enrdf_load_stackoverflow)
BE (1) BE754886A (enrdf_load_stackoverflow)
CA (1) CA977904A (enrdf_load_stackoverflow)
CH (2) CH1219270A4 (enrdf_load_stackoverflow)
FR (1) FR2058330B1 (enrdf_load_stackoverflow)
GB (1) GB1274134A (enrdf_load_stackoverflow)
NL (1) NL7012054A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989455A (en) * 1973-05-29 1976-11-02 Allied Chemical Corporation Tertiary amines, substituted piperidine, morpholine or piperazine containing fatty acid moieties to prevent ozone fading of nylon fibers
US4030882A (en) * 1975-01-02 1977-06-21 Eastman Kodak Company Solvent dyeing compositions and a method of dyeing polyester fibers therewith
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
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4413998A (en) * 1978-07-27 1983-11-08 Ciba-Geigy Corporation Process for the treatment of textile fibre materials

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274751A (en) * 1942-03-03 Materials
US2721111A (en) * 1951-08-01 1955-10-18 American Cyanamid Co Oil and spirit soluble azo dyestuffs
US3164449A (en) * 1961-03-01 1965-01-05 Du Pont Anthraquinone dyes for gasoline
BE682830A (enrdf_load_stackoverflow) * 1965-06-22 1966-12-01
CH454084A (de) * 1966-01-05 1967-12-29 Geigy Ag J R Verfahren zum kontinuierlichen Färben oder Bedrucken von Textilmaterial aus synthetischem Polyamid
FR1581325A (enrdf_load_stackoverflow) * 1967-09-29 1969-09-12
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
US3523749A (en) * 1965-09-30 1970-08-11 Ici Ltd Process for dyeing viscose rayon and nylon with subsequent fixation in a halogenated hydrocarbon bath

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH337566A (fr) * 1954-06-23 1959-04-15 Valantin Lucien Installation pour le revêtement des routes
GB1241899A (en) * 1968-08-02 1971-08-04 Bayer Ag Improved exhaustion process for dyeing fibre material containing-nh-groups
US3630663A (en) * 1968-08-30 1971-12-28 Bayer Ag Process for dyeing anionic modified synthetic fibers in dye baths containing an organic nitrogen compound

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274751A (en) * 1942-03-03 Materials
US2721111A (en) * 1951-08-01 1955-10-18 American Cyanamid Co Oil and spirit soluble azo dyestuffs
US3164449A (en) * 1961-03-01 1965-01-05 Du Pont Anthraquinone dyes for gasoline
BE682830A (enrdf_load_stackoverflow) * 1965-06-22 1966-12-01
US3523749A (en) * 1965-09-30 1970-08-11 Ici Ltd Process for dyeing viscose rayon and nylon with subsequent fixation in a halogenated hydrocarbon bath
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
CH454084A (de) * 1966-01-05 1967-12-29 Geigy Ag J R Verfahren zum kontinuierlichen Färben oder Bedrucken von Textilmaterial aus synthetischem Polyamid
US3623834A (en) * 1966-01-05 1971-11-30 Ciba Geigy Ag Dye solution or print paste containing chlorinated hydrocarbon with an alcohol ketone dioxane alkanoic acid amide tetramethyl urea or pyridine and polyamide dyeing therewith
FR1581325A (enrdf_load_stackoverflow) * 1967-09-29 1969-09-12

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Colour Index, and Ed., 1956, Vol. 2, pp. 2815 and 2816. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US3989455A (en) * 1973-05-29 1976-11-02 Allied Chemical Corporation Tertiary amines, substituted piperidine, morpholine or piperazine containing fatty acid moieties to prevent ozone fading of nylon fibers
US4030882A (en) * 1975-01-02 1977-06-21 Eastman Kodak Company Solvent dyeing compositions and a method of dyeing polyester fibers therewith
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
US4413998A (en) * 1978-07-27 1983-11-08 Ciba-Geigy Corporation Process for the treatment of textile fibre materials

Also Published As

Publication number Publication date
CA977904A (en) 1975-11-18
BE754886A (fr) 1971-01-18
FR2058330B1 (enrdf_load_stackoverflow) 1975-02-21
FR2058330A1 (enrdf_load_stackoverflow) 1971-05-28
CH544183A (de) 1973-05-30
CH1219270A4 (enrdf_load_stackoverflow) 1973-05-30
GB1274134A (en) 1972-05-10
JPS5029074B1 (enrdf_load_stackoverflow) 1975-09-20
NL7012054A (enrdf_load_stackoverflow) 1971-02-18
DE1941698A1 (de) 1971-02-18
DE1941698B2 (de) 1977-06-16

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