US3918902A - Dyeing of synthetic organic material with aliphatic and halogenated aliphatic solution - Google Patents

Dyeing of synthetic organic material with aliphatic and halogenated aliphatic solution Download PDF

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US3918902A
US3918902A US349893A US34989373A US3918902A US 3918902 A US3918902 A US 3918902A US 349893 A US349893 A US 349893A US 34989373 A US34989373 A US 34989373A US 3918902 A US3918902 A US 3918902A
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dyeing
polyhalogenated
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aliphatic hydrocarbon
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Hansruedi Hoster
Jurgen Markert
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Novartis AG
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Ciba Geigy AG
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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
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/56—Mercapto-anthraquinones
    • C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester 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
    • Y10S8/92—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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • a dye liquor consisting of 20 to 75 per cent by weight of a waterinsoluble. aliphatic or cycloaliphatic hydrocarbon having at least 8 carbon atoms. and to 25 per cent by weight of a polyhalogenated. lower alphatic hydrocarbon boiling between 70 and C. and at least one advantageously finely divided dispersion dyestuff. and optionally further additives; and. optionally. the subse quent rinsing and drying of the dyed synthetic organic material. whereby deeply coloured dyeings are ob tained which are even and fast to light. wetprocessing. sublimation and rubbing even on poorly absorbing material.
  • the present invention relates to a process for the dyeing of synthetic organic material, particularly textile material, from organic dye liquors, to the organic dye liquors usable in this process, as well as to the material dyed by this process.
  • the new process comprises the discontinuous or continuous dyeing, at temperatures of above 100C, preferably above 120C, of the synthetic organic material from a dye liquor consisting of to 75, advantageously 50 to 70, per cent by weight of a water-insoluble, aliphatic or cycloaliphatic hydrocarbon having at least 8 carbon atoms, and 80 to 25, advantageously 50 to 30, per cent by weight of a polyhalogenated, lower aliphatic hydrocarbon boiling between 70 and 180C, and at least one advantageously finely divided dispersion dyestuff, and possible further additives; and, optionally, the subsequent rinsing and drying of the dyed synthetic organic material.
  • a dye liquor consisting of to 75, advantageously 50 to 70, per cent by weight of a water-insoluble, aliphatic or cycloaliphatic hydrocarbon having at least 8 carbon atoms, and 80 to 25, advantageously 50 to 30, per cent by weight of a polyhalogenated, lower aliphatic hydrocarbon boiling between 70 and 180C, and at least one advantageously
  • Suitable water-insoluble, aliphatic and cycloaliphatic hydrocarbons usable according to the invention, having at least 8 carbon atoms are, for example, the following: both straight-chain and branched alkanes, advantageously having 12 to 25 carbon atoms; cycloalkanes such as, e.g. ethylcyclohexane, cyclooctane, cyclodecane or Decalin; halogenation products of higher molecular hydrocarbons which, for example, are obtained by addition of chlorine to hard paraffin; oxygen-containing waxes, e.g.
  • the mixtures (forming by atmospheric oxidation of aliphatic hydrocarbons) of esters, acids and oxyacids of the corresponding higher molecular hydrocarbons; also aliphatic hydrocarbons of which the carbon chain is interrupted by hetero atoms, particularly by -O-, -S- or NI-L, such as, e.g. di-n-octyl ether, di-n-decyl-thio ether or di-n-dodecylamine.
  • paraffin e.g. the petroleum fraction of mineral oil containing the paraffins C, C and boiling within the range of 220 to 270C, or gas oil fractions also containing solid hydrocarbons having up to about 25 carbon atoms.
  • High-boiling ligroin or petroleum fractions obtainable under the designation of Schwerbenzin, Kerosin and especially "Paraffinol (heavy petrol, kerosene and paraffin oil).
  • Heavy petrol contains ca. 20 to 25 percent of fractions boiling at 100C, the remainder mostly at I50 l80C, occasionally even higher.
  • Kerosene is the distillate passing over after the ligroin fraction; it has a boiling range of I 288C and a density of 0.7 to 0.8, and consists essentially of a hydrocarbon mixture of C to C
  • paraffin oil consists of a higher molecular mixture of aliphatic hydrocarbons obtained from the liquid fractions in the obtaining of paraffin, and having a boiling point of at least 280C and a density of at least 0.75.
  • Suitable polyhalogenated, lower aliphatic hydrocarbons boiling between 70 and 180C for the process according to the invention are, for example: carbon tetrachloride, dichloroethane, trichloroethane, tetrachloroethane, pentachloroethane, trichlorotrifluoroethane, dibromoethylene, dichloropropane, trichloropropane, pentachloropropane, dichlorobutane a'nd dichlorohexane.
  • Particularly advantageous are chlorinated hydrocarbons boiling between and C, such as trichloroethylene, l,l,l-trichloroethane, and especially tetrachloroethylene (perchloroethylene").
  • Applicable anti-oxidants are all the important classes of compounds having an anti-oxidising action, such as, e.g.:
  • hydroquinone and its functional derivatives such as hydroquinone-monoand dialkyl of arylalkyl ethers
  • esters of gallic acid or citraconic acid as well as mixtures thereof;
  • dialkylphosphonates particularly those with sterically inhibited phenols, or also p-hydroxyphenylphosphonates and compounds of p-phenylenediamine or of p-aminophenol;
  • compounds of the formamidinesulphinic acid type or inorganic complex hydrides such as NaBl-L, etc., of which the hydrogen can be partially replaced by organic radicals, such as NaBI-KOCHQ; or NaBH- (OC,H Preferred antioxidants, since they are effective in extremely small amounts, are those which are sufficiently soluble in the mixture ratios of tetrachloroethylene and paraffin oil according to the invention.
  • the quantity ratios of the employed anti-oxidants can vary within wide limits; in general, amounts of 0.00] to 5 g/l of dye liquor, particularly 0.01 to 1.0 g/l, have proved effective.
  • the dispersion dyestuffs usable according to the invention can belong to the most diverse classes of dyestuffs. They are, in particular, azo, anthraquinone, nitro, phthalocyanine, methine, styryl, naphthoperinone, quinophthalone, acridone or 5-amino-8-hydroxyl-l,4- naphthoquinoneimine dyestuffs.
  • Preferred dyestuffs are metal-free monoor disazo dyestuffs, nitro dyestuffs, methine dyestuffs and anthraquinone dyestuffs.
  • dyestuffs are meant also optical dispersion brighteners, e.g. brighteners from the coumarin, azole or naphthalamide series.
  • the amounts in which the dispersion dyestuffs are used in the organic dye baths according to the inven- 4 tion can vary, depending on the desired depth of colour, within wide limits; in general, amounts of from 0.001 to 10 per cent by weight, relative to the material to be dyed, of one or more of the stated dyestuffs have proved advantageous.
  • dispersion dyestuffs soluble in boiling perchloroethylene are used, then the commercial dyestuffs containing no dispersing agents can be employed direct. If the dyestuffs are at least partially in the dispersed state in the organic dye liquor, then the presence of dispersing agents is advisable.
  • dispersion dyestuffs are used which are difficulty soluble in boiling perchloroethylene and which contain a dispersing agent soluble in polyhalogenated lower aliphatic hydrocarbon, but which does not solubilise the dispersion dyestuff.
  • Particularly preferred dispersion dyestuffs are ones which have a solubility in boiling perchloroethylene of at most 0.05, preferably 0.03, per cent by weight, and a particle size of at most 5 1., preferably one between 0.1 and 3 u.
  • the finely divided dispersion dyestuffs can be obtained by known processes; for example, by mechanical particle-size reduction of the dyestuff together with a dispersing agent, and optionally smallish amounts of halogenated aliphatic hydrocarbon, particularly perchloroethylene, e.g. in a kneading apparatus, preferably however in a grinding mill. Especially suitable for this purpose are ball or sand mills.
  • Suitable dispersing agents are commercial anionic, cationic, ampholytic and, in particular, nonionic surface-active agents which advantageously are soluble in the organic dye liquor, but which do not solubilise the dyestuffs.
  • alkylene oxides particularly ethylene oxide
  • higher fatty acids fatty acids
  • fatty amides aliphatic alcohols
  • mercaptans or amines with alkyl phenols of which the alkyl radicals contain at least 7 carbon atoms
  • esters of polyalcohols especially monoor diglycerides of fatty acids, e.g. the monoglycerides of lauric, stearic, palmitic or oleic acid, as well as fatty acid esters of sugar alcohols, such as of sorbitol, sorbitans and saccharose, e.g.
  • sorbitan monolaurate (Span 20), -palmitate (Span 40), -stearate (Span 60), -oleate (Span -sesquioleate, -trioleate (Span or their oxethylation products; and, finally, also quaternary ammonium salts such as dodecylammonium acetate, cetylpyridinium acetate, or quaternated alkylammonium polyglycol ethers such as are described in the Swiss Pat. Specification No.
  • Sapamines such as Sapamine CH, KW, MS or DC, polydiene resins, fatty acid amides, or substances which contain the amide groups in ring form, such as in the case of the derivatives of polyvinylpyrrolidone, that are obtainable commercially, e.g. under the name of Antaron V 216 and V 220," and have a molecular weight of about 7000 to 9000.
  • the organic dye liquor according to the invention can contain as further additives dispersing agents such as the above mentioned, or acids such as formic acid or glacial acetic acid.
  • the organic dye liquors according to the invention are suitable for the dyeing of synthetic organic material of the most diverse kinds of processes known per se.
  • materials are: fibre materials made from synthetic polyamide, such as condensation products from hexamethylenediamine and 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 polymerisation products from e-caprolactam, known under the trade-name of Polyamide 6," Perlon, Grilon" or Enkalon," or from m-aminoundecanoic acid, Polyamide 11" or Rilsan.
  • synthetic polyamide such as condensation products from hexamethylenediamine and adipic acid (polyamide 6.6) or sebacic acid (polyamide 6.10), or mixed condensation products, e.g. from hexamethylenediamine, adipic acid and
  • acid modified synthetic fibres such as acid modified polyamide, polyurethane and polyester fibres, and particularly polyacrylonitrile or polyacrylonitrile copolymer fibres.
  • polyacrylonitrile copolymer fibres the acrylonitrile proportion is preferably at least 80 per cent by weight of the copolymer.
  • comonomers there are used, besides acrylonitrile, normally other vinyl compounds, e.g. vinylidine chloride, vinylidene cyanide, vinyl chloride, methacrylate, methylvinylpyridine, N-vinylpyrrolidone, vinyl acetate, vinyl alcohol or styrenesulphonic acid, or polyolefin fibres such as Polycrest.”
  • polyester materials such as linear high-molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols, e.g. those from terephthalic acid and ethylene glycol or dimethylolcyclohexane, and mixed polymers from terephthalic acid and isophthalic acid and ethylene glycol.
  • mixtures of the mentioned fibres can be used, particularly mixtures of synthetic polyamide and polyester fibres.
  • the process according to the invention which is preferably carried out in closed, pressure-tight apparatus, e.g. in circulation apparatus, jet-machines, winchdyeing machines, drum-type dyeing machines, vats, paddle-dyeing machines and cheese dyeing apparatus, can be carried out, for example, as follows:
  • the material to be dyed is placed into the organic dye bath at room temperature, with a ratio of material to liquor of 1:3 to 1:40, preferably 1:5 to 1:20; the finely dispersed dyestufi is added to the liquor; and the dye bath is then, heated to above 100C, advantageously to between 120 and 150C, and held at this temperature for ca. 5 to 120 minutes, advantageously for to 45 minutes.
  • the bath After attainment of the desired depth of colour, or with complete exhaustion of the dye bath, the bath is cooled; the dyed material removed from the bath; and, optionally after rinsing, e.g. by treatment twice with perchloroethylene for 5 minutes at 85C, dried, advantageously in vacuo with saturated steam for ca. 10 minutes.
  • organic dye liquors instead of water as the dye bath offers a number of advantages: in the solventexhaust process, the exhaustion of the dye bath occurs more quickly than in aqueous media, resulting in shorter dyeing times; furthermore, the organic dye liquor can be easily recovered, e.g. by passage through an activecharcoal filter, in consequence of which the ever increasing difficulties associated with the cleansing of effluent are completely avoided.
  • the purified recovered dye liquors can be used afresh as organic dye liquors to an unlimited extent.
  • EXAMPLE 1 An amount of 0.1 g of the dyestuff of the formula is dissolved in 32 g 20 ml) of tetrachloroethylene at The warm dyestuff solution and 10 g of textured polyethylene glycol terephthalate knitted fabric are placed into a closable dyeing apparatus, which is designed to enable movement of the textile material to be effected and which contains 64 g 80 ml) of paraffin oil heated to 80. The apparatus is then closed and, with continuous movement of the textile material, the bath temperature raised within 10 minutes to 140, and this temperature maintained for 30 minutes.
  • the dyed knitwear is removed, and squeezed out to leave as little residual liquor as possible in the material; it is subsequently rinsed twice by being heated with tetrachloroethylene, with a material to liquor ratio of 1:8, in the above mentioned apparatus for 5 minutes at the material is afterwards squeezed out and finally dried azeotropically with aqueous saturated steam for 30 minutes.
  • the stock dispersion employed in the example was produced as described in Example 8, but with the use of 15 g of the dyestuff of the formula given in Example 9, 15 g of Antaron V 216 and 70 g of paraffin oil.
  • EXAMPLE 10 10 g of textured polyethylene glycol terephthalate fabric (TREVlRA) is placed, with a material to liquor ratio of 1:10, into a dye bath at 60 contained in a closable dyeing apparatus, the said dye bath having been 10 prepared by dispersion of 0.22 g of the stock dispersion containing 0.03 g of the dyestuff of the formula 0.006 g of Pluronic P 104 and 0.184 g of paraffin oil, and 0.27 g of the stock dispersion given in Example 9, in 58 g 40 ml) of trichloroethylene, heating of the dispersion to 60 and subsequent addition thereof to 48 g 60 ml) of paraffin oil at 60.
  • TSVlRA textured polyethylene glycol terephthalate fabric
  • the dyeing apparatus is then closed and, with continuous movement of the material being dyed, the temperature of the dye bath raised within 5 minutes to 140 and this temperature maintained for 30 minutes.
  • the dyed fabric is removed and squeezed out; it is then rinsed twice by being heated with trichloroethylene, with a material to liquor ratio of 1:10, in the above mentioned apparatus for 5 minutes at squeezed out, and afterwards azeotropically dried with aqueous saturated steam for 15 minutes.
  • the stock dispersion of the formula given in the example was produced in the manner described in Example 8, but with employment of 15 g of the dyestuff of the above formula, 3 g of Pluronic P 104 (a polyoxypropylenepolyoxyethylene compound, mol. weight 2500) and 82 g of paraffin oil.
  • Pluronic P 104 a polyoxypropylenepolyoxyethylene compound, mol. weight 2500
  • Example 10 If there is used, instead of the dyestuff mixture employed in Example 10, 0.1 g of one of the undiluted dyestuffs listed in the following Table 11, Column 11, added as a l0 percent stock dispersion, the procedure otherwise being as described in Example 10, then on textured polyester material there are obtained dyeings in the shades described in Column ll].
  • Example 8 the procedure otherwise being as described in Example 8, then there is obtained on the cellulose triacetate fabric a deeply coloured, even red dyeing which is well dyed throughout, and which has good fastness to wet processing and to light.
  • EXAMPLE 36 An amount of 0.22 g of the stock dispersion of the formula given in Example is dispersed in 32 g 20 ml) of tetrachloroethylene; the dispersion is heated to 60 and then added to 64 g 80 ml) of paraffin oil at 60 contained in a closable dyeing apparatus. There is then introduced into the dye liquor 10 g of a polyamide-6.6-tricot; the dyeing apparatus is closed and the dye bath heated, with continuous movement of the material being dyed, within 5 minutes to 140, and this temperature maintained for 30 minutes.
  • the dyed material After cooling to 80, the dyed material is removed and squeezed out; it is rinsed twice by being heated with tetrachloroethylene in the dyeing apparatus, with a material to liquor ratio of 1:10, for 5 minutes at 50, and subsequently azeotropically dried with aqueous saturated steam for minutes.
  • EXAMPLE 37 If 10 g of polyacrylonitrile fabric are used instead of the polyamide-6.6-tricot mentioned in Example 36, with the procedure otherwise as described in Example 36, then there is obtained on the said polyacrylonitrile fabric a deeply coloured, even yellow dyeing.
  • EXAMPLE 38 An amount of 10 g of textured polyethylene glycol terephthalate knitted fabric is placed into a bath (ratio of material to liquor 1:10) contained in a closable dyeing apparatus, the said bath having been prepared by the dispersion of 0. l 5 g of a stock dispersion consisting of 0.012 g of Antaron V 216 (modified polyvinylpyrrolidone), 0.128 g of paraffin oil and 0.01 g of 2,6-di-tert- .butylphenol in 32 g ml) of commercial tetrachloroethylene stabilised with an aliphatic, cycloaliphatic, aromatic or heterocyclic amine.
  • a bath ratio of material to liquor 1:10
  • the said bath having been prepared by the dispersion of 0. l 5 g of a stock dispersion consisting of 0.012 g of Antaron V 216 (modified polyvinylpyrrolidone), 0.128 g of par
  • the temperature is raised to 60; an addition is made of 64 g 80 ml) of paraffin oil at 60, the dyeing apparatus is closed and, with continual movement of the material to be treated, the bath heated within 10 minutes to 140 and this temperature maintained for 30 minutes.
  • the thus treated knitted fabric is removed and squeezed out to leave as little residual liquor as possible in the material; it is then rinsed twice by being heated with tetrachloroethylene, in the ratio of material to liquor of I :8, in the above mentioned apparatus for 5 minutes at 85, squeezed out, and subsequently azeotropically dried with aqueous saturated steam for 30 minutes.
  • the polyethylene glycol terephthalate knitted fabric treated in this manner displays absolutely no grey discolouration or modification of its fibre-physical properties compared with an untreated comparative sample. Similar results are obtained if, instead of 2,6-di-tert- .butylphenol, other oxidation-inhibitors are employed, such as, e.g. 4-tert.butylphenol, 2,6-di-tert.butyl-4- methylphenol or their alkoxy derivatives, such as, for
  • EXAMPLE 39 An amount of 10 g of polyethylene glycol terephthalate fabric (TREVlRA) is placed into a bath (ratio of material to liquor 1:10) contained in a closable dyeing apparatus, the said bath having been prepared by the dispersion of 0. 1 71 g of a stock dispersion consisting of 0.012 g ofAntaron V 216, 0.128 g ofparaffin oil, 0,001 g of hydroquinone and 0.03 g of the finely dispersed dyestuff in 32 g 20 ml) of commercial tetrachloroethylene stabilised with an aliphatic, cycloaliphatic, aromatic or heterocyclic amine.
  • a bath ratio of material to liquor 1:10
  • the said bath having been prepared by the dispersion of 0. 1 71 g of a stock dispersion consisting of 0.012 g ofAntaron V 216, 0.128 g ofparaffin oil, 0,001 g of hydroquinone and 0.
  • a process for the exhaust dyeing of synthetic organic materiaL'the process comprising the step of contacting the synthetic organic material, at a temperature above C, with a dye liquor consisting essentially of 20 to 75 percent by weight of a water-insoluble, aliphatic or cycloaliphatic hydrocarbon having 8 to 25 carbon atoms, and 80 to 25 percent by weight of a polyhalogenated, lower aliphatic hydrocarbon boiling between 70 and 180C, and at least one finely-divided dispersion dyestuff which is difficutly soluble in boiling perchloroethylene.
  • a dye liquor consisting essentially of 20 to 75 percent by weight of a water-insoluble, aliphatic or cycloaliphatic hydrocarbon having 8 to 25 carbon atoms, and 80 to 25 percent by weight of a polyhalogenated, lower aliphatic hydrocarbon boiling between 70 and 180C, and at least one finely-divided dispersion dyestuff which is difficutly soluble in boiling perchloroethylene.
  • waterinsoluble, aliphatic hydrocarbon is heavy petrol, kerosene or paraffin oil.
  • polyhalogenated, lower aliphatic hydrocarbon is trichloroethylene, l,l,1-trichloroethane or tetrachloroethylene (perchloroethylene).
  • the antioxidant is selected from the class consisting of a. the derivatives of alkylated, arylated or mixed phenols, phenol ethers of phenol esters, as well as bisphenols with or without alkylene bridging, particularly those of the general formula OH HO wherein R represents an alkyl group having 1 to 6 carbon atoms, an aryl or an alkylaryl group, and n denotes the numbers to 6;
  • hydroquinone and its functional derivatives such as hydroquinone-mono and dialkyl or arylalkyl ethers
  • esters of gallic acid or citraconic acid as well as mixtures thereof;
  • dialkylphosphonates particularly those with stearically inhibited phenols, or also p-hydroxyphenyl-phosphonates and compounds of pphenylenediamine or of p-aminophenol;
  • dispersion dyestuff is selected from metalfree monoand disazo dyestuffs, nitro dyestuffs, methine dyestuffs and anthraquinone dyestuffs.
  • dispersion dyestuff contains a nonionic dispersing agent which is soluble in polyhalogenated, lower aliphatic hydrocarbon, but which does not solubilise the dispersion dyestuff.
  • the dispersion dyestuff has a solubility in boiling perchloroethylene of at most 0.05 percent by weight, and which has a particle size of at most 5 p" 15.
  • the synthetic organic material is polyester, polyamide or polyacrylonitrile fibre material.
  • the synthetic organic material is fibre material made from linear, highmolecular esters of aromatic polycarboxylic acids with polyfunctional alcohols.
  • a dye liquor for the dyeing of synthetic organic material consisting essentially of a finely-divided dispersion dyestuff, 5 to percent by weight of a water-insoluble, aliphatic or cycloaliphatic hydrocarbon having 8 to 25 carbon atoms, and 95 to 5 percent by weight of a polyhalogenated, lower aliphatic hydrocarbon boiling between 70 and C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US349893A 1972-04-12 1973-04-10 Dyeing of synthetic organic material with aliphatic and halogenated aliphatic solution Expired - Lifetime US3918902A (en)

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CH535672A CH559818A (de) 1972-04-12 1972-04-12 Verfahren zum faerben von synthetischem organischem material.

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US (1) US3918902A (en。)
JP (1) JPS4914779A (en。)
AU (1) AU5432973A (en。)
BE (1) BE798064A (en。)
CA (1) CA995862A (en。)
CH (2) CH559818A (en。)
ES (1) ES413560A1 (en。)
FR (1) FR2180012B1 (en。)
GB (1) GB1402232A (en。)
IL (1) IL42010A (en。)
IT (1) IT980151B (en。)
NL (1) NL7304936A (en。)
ZA (1) ZA732468B (en。)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080166A (en) * 1975-02-15 1978-03-21 Hoechst Aktiengesellschaft Emulsifiers for dyeing accelerators based on alkylnaphthalenes
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

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50153677A (en。) * 1974-05-31 1975-12-10
JPS5254365A (en) * 1975-10-30 1977-05-02 Ise Electronics Corp Dot matrix fluorescent character display tube
JPS5273670A (en) * 1975-12-17 1977-06-20 Ise Electronics Corp Multiicharacter fluorescent display tube
JPS5753409Y2 (en。) * 1979-09-25 1982-11-19
JPS5810284Y2 (ja) * 1980-11-13 1983-02-24 伊勢電子工業株式会社 ドツトマトリツクス螢光文字表示管

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1925602A (en) * 1931-09-05 1933-09-05 Du Pont Stabilized solvent
US2492048A (en) * 1945-08-24 1949-12-20 Du Pont Stabilization of trichloroethylene and tetrachloroethylene
US2828180A (en) * 1952-05-31 1958-03-25 Anonima Italiana Colori E Affi Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers
US3040108A (en) * 1960-11-14 1962-06-19 Hooker Chemical Corp Stabilization of perchloroethylene
US3046076A (en) * 1959-08-25 1962-07-24 Burlington Industries Inc Process for coloring polyolefinic textile materials
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
US3758272A (en) * 1967-09-29 1973-09-11 Ciba Geigy Ag Process for dyeing hydrophobic textile material
US3792971A (en) * 1969-10-18 1974-02-19 Bayer Ag Exhaust process for the dyeing of synthetic fibre materials
US3807953A (en) * 1971-05-28 1974-04-30 Sandoz Ltd Method of disperse dyeing and carrier composition therefor
US3822992A (en) * 1970-10-12 1974-07-09 Bayer Ag Exhaustion dyeing process with anthraquinone dyestuffs in water immiscible organic solvent

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Publication number Priority date Publication date Assignee Title
GB504558A (en) * 1937-10-22 1939-04-22 Percy Frederick Combe Sowter Improvements in the colouration of textile and other materials
FR1603051A (fr) * 1968-08-06 1971-03-15 Ugine Kuhlman S.A Teinture des fibres textiles comportant des fonctions basiques

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1925602A (en) * 1931-09-05 1933-09-05 Du Pont Stabilized solvent
US2492048A (en) * 1945-08-24 1949-12-20 Du Pont Stabilization of trichloroethylene and tetrachloroethylene
US2828180A (en) * 1952-05-31 1958-03-25 Anonima Italiana Colori E Affi Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers
US3046076A (en) * 1959-08-25 1962-07-24 Burlington Industries Inc Process for coloring polyolefinic textile materials
US3040108A (en) * 1960-11-14 1962-06-19 Hooker Chemical Corp Stabilization of perchloroethylene
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
US3758272A (en) * 1967-09-29 1973-09-11 Ciba Geigy Ag Process for dyeing hydrophobic textile material
US3792971A (en) * 1969-10-18 1974-02-19 Bayer Ag Exhaust process for the dyeing of synthetic fibre materials
US3822992A (en) * 1970-10-12 1974-07-09 Bayer Ag Exhaustion dyeing process with anthraquinone dyestuffs in water immiscible organic solvent
US3807953A (en) * 1971-05-28 1974-04-30 Sandoz Ltd Method of disperse dyeing and carrier composition therefor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080166A (en) * 1975-02-15 1978-03-21 Hoechst Aktiengesellschaft Emulsifiers for dyeing accelerators based on alkylnaphthalenes
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

Also Published As

Publication number Publication date
AU5432973A (en) 1974-10-10
NL7304936A (en。) 1973-10-16
ZA732468B (en) 1974-04-24
FR2180012A1 (en。) 1973-11-23
CH535672A4 (en。) 1974-07-15
IL42010A (en) 1976-09-30
JPS4914779A (en。) 1974-02-08
CH559818A (de) 1975-03-14
FR2180012B1 (en。) 1976-09-10
GB1402232A (en) 1975-08-06
BE798064A (fr) 1973-10-11
CA995862A (en) 1976-08-31
ES413560A1 (es) 1976-01-16
IT980151B (it) 1974-09-30
IL42010A0 (en) 1973-06-29
CH559818B5 (en。)

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