US3776690A - Process for dyeing textiles made of polyester or cellulose triacetate - Google Patents

Process for dyeing textiles made of polyester or cellulose triacetate Download PDF

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Publication number
US3776690A
US3776690A US00205718A US3776690DA US3776690A US 3776690 A US3776690 A US 3776690A US 00205718 A US00205718 A US 00205718A US 3776690D A US3776690D A US 3776690DA US 3776690 A US3776690 A US 3776690A
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United States
Prior art keywords
dyeing
emulsifier
percent
perchloroethylene
polyester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00205718A
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English (en)
Inventor
S Wiatrowski
C Heid
K Keil
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cassella Farbwerke Mainkur AG
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Cassella Farbwerke Mainkur AG
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Priority claimed from DE19702060565 external-priority patent/DE2060565C3/de
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
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Publication of US3776690A publication Critical patent/US3776690A/en
Anticipated expiration legal-status Critical
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/651Compounds without nitrogen
    • D06P1/6515Hydrocarbons
    • D06P1/65156Halogen-containing hydrocarbons
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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 dispersed, e.g. acetate, dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/36Material containing ester groups using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/20Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D06P5/2044Textile treatments at a pression higher than 1 atm
    • D06P5/2055Textile treatments at a pression higher than 1 atm during dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/907Nonionic emulsifiers for dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • Y10S8/912Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/921Cellulose ester or ether
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber

Definitions

  • carrier is to be understood as defining such substances as loosen up the fiber structure and, thus, facilitate the absorption of the dyestuff.
  • the carriers customarily used are aromatic compounds, such as diphenyl, halogeno benzenes, esters of the benzoic, salicylic or cresotic acids, naphthalene and alkylnaphthalenes, o-phenylphenol and others as well as tripropyl-phosphate.
  • the use of carriers is impaired by a number of disadvantages, such as the formation of unpleasant smells during the dyeing, the toxicity of the carrier and the adverse influence on the fastness to light of the dyeings obtained.
  • a further known process for dyeing polyester and cellulose triacetate fibers which is described in DOS 1,918,340, consists in that the fibers are treated with halogenated hydrocarbons prior to getting into contact with the dyeing liquor.
  • This treatment normally consists in that the fibers are placed, for several minutes, into a more or less heated halogenated hydrocarbon solvent. Subsequently, the excess halogenated hydrocarbon solvent is removed by dipping the fiber material into hot water or by treating it with steam. Dyeing is then carried out in an appropriate manner with an aqueous dye-bath being heated to the boil.
  • This process involves, however, the disadvantage that it does require two specific additional pre-treatments, i.e.
  • a further process known from French patent 1,141,819 consists in dyeing linear aromatic polyesters by adding to the dye-bath halogenated aliphatic hydrocarbons having a boiling point below 125C. together with sodium olely sulfate as emulsifier. Dyeing is then carried out in an open vessel at temperatures below 2 C. This process leads to only poor dye yields and involves the risk that the dyeings obtained are uneven. Consequently, neither this known process nor the use of halogenated aliphatic hydrocarbons as carriers have been approved of in practice.
  • trichloroethylene or perchloroethylene is excellently suited as carriers for dyeing textiles made of polyester or cellulose triacetate provided that the trichloroethylene or the perchloroethylene or a mixture of both is employed in small amounts ranging from 0.5 to 10 c.c./l. and that the dyeing is carried out under pressure at temperatures above 100C.
  • the present invention relates to a process for dyeing textiles made of polyester or cellulose triacetate in an aqueous medium with dispersed dyes, at an elevated temperature and with the use of trichloroethylene and/or perchloroethylene as carrier and an emulsifier.
  • the process of the present invention is characterized in that the dyeing is carried out under pressure at temperatures above 100C. with 0.5 to 10 c.c./l. of the carrier.
  • the carrier is employed in amounts ofl.5 to 5 c.c.ll.
  • the emulsifier to be used according to the present invention may be any known emulsifier, whereby this term is to be understood as defining any substance or mixture of substances preventing the separate phase of an emulsion, in the instant case the individual drops of 'the trichloroethylene and/or perchloroethylene, from fusing together.
  • One condition of such effect is the activity of the interfaces.
  • a useful emulsifier has to show a stabilizing effect which is due either to the electric charge involving an electrostatic repulsion of the particles, or to the formation of a stable protective film. These effects may also be superposed.
  • Suitable emulsifiers are for instance: anion active substances, such as alkyl sulfates (for instance sodium lauryl sulfate and sodium cetyl sulfate), Turkey red oils, sulphonated oils, alkyl sulfonates,alkylarylsulfonates, such as alkylbenzyl sulfonates and alkyl naphthalene sulfonates.
  • emulsifiers are nonionic ethyleneoxide and/or propyleneoxide adducts, such as oxethylated alkylphenols, alcohols, aliphatic or unsaturated carboxylic acids, fatty amines, hydroxyl group-containing esters of saturated or unsaturated carboxylic acids. It is also possible to employ mixtures of emulsifiers as are described, for instance, in DOS 1,619,489 and DOS 1,802,210.
  • mixtures of emulsifiers consist, for instance, of addition compounds obtained by adding ethyleneoxide on alkylphenols (component 1), alkali salts of alkylbenzene sulfonic acids (component 11) and aliphatic primary or secondary alcohols having three to six carbon atoms (component 111).
  • the emulsifier employed is a mixture of oxethylated castor oil and the calcium salt of the dodecylbenzene sulfonic acid,
  • a dispersing agent in order to avoid a flocculation of the standardizing agent which may be present in commerical dispersed dye preparations.
  • a dispersing agent is, for instance, the sodium methylene-bisnaphthalene sulfonate.
  • the emulsifier or the mixture of emulsifiers may be added to the aqueous dye liquor. Subsequently, the trichloro or perchloroethylene, or a mixture of trichloro and perchloroethylene may be added with stirring. In general, however, it is simpler and more advisable to add the emulsifier or the mixture of emulsifiers to the trichloro and/or perchloroethylene and to introduce while stirring the mixture thus obtained to the dye liquor.
  • an amount of 5 M45 percent by weight of emulsifier is employed which means that, if a mixture of the emulsifier and the trichloro or perchloroethylene is used, about 4.8 to 31 percent by weight of emulsifier may be present in such mixture.
  • emulsifier ie those ranging from 5 to percent by weight related to the carrier, rather than large amounts.
  • Dyeing is preferably carried out with pressure and at temperatures ranging from 105 to 130C.
  • polyester or cellulose triacetate materials to be dyed may be employed, for instance, in the form of yarn or woven or knitted fabrics. They may furthermore contain other materials, such as wool or polyacrylonitrile.
  • the process of the present invention is substantially simpler and less expensive and yields dyeings that are at least on a par with the dyeings obtained according to the known process.
  • the process of the present invention leads in many cases to a substantial improvement of the levelling power of dispersed dyes, whichhas favorable consequences in particular onthe appearance of textured materials.
  • a barry dyeing may be avoided or at least may thus disadvantage considerably be reduced. Consequently, it is possible to use in the process of the present invention also those dispersed dyes which strongly mark.
  • Such dyes have in most cases excellent fastness properties, but could hitherto practically not be used on textured materials due to the strong marks of the barriness (barre effect).
  • a very good dye yield is obtained which normally exceeds that obtained with the use of the customary carriers.
  • a further advantage of the instant process consists in that the fastness to light of the dyeings obtained is not disadvantageously influenced evenif the dyeings are not re-fixed.
  • EXAMPLE 1 A fabric containing polyester fibers that are heat-set in different ways is dyed at a liquor ratio of 1:20 from an aqueous dye-bath with 2.5 percent (related to the weight of the fabric) of a finely dispersed dye of the formula and with the addition of 3 c.c.ll. of a mixture of 95 percent perchloroethylene and 5 percent emulsifier. The temperature is raised within 30 minutes to 120 and dyeing is carried out during 90 minutes at this temperature.
  • the emulsifier employed consists of a mixture of calcium-dodecylbenzene sulfonate and .oxethylated castor oil (containing 30 oxethyl groups in the molecule) at a weight ratio of 1:1.
  • Polyester yarn is dyed at a liquor ratio of 1:10 from an aqueous dye-bath containing 3 percent (related to the weight of the fabric) Palanilviolett. 38 (Cl. Disperse .Violet 8; C.I. No. 62030), 5 c.c./l. of a mixture of 90 percent perchloroethylene and 10 percent emulsifier as well as l g./l. sodium methylene-bis-naphthalenesulfonate. The mixture is heated within 30 minutes to 120 and dyeing is carried out during 90 minutes at 120.
  • the emulsifier employed is an ethoxylated coconut oil amine with 10 ethoxyl groups in the molecule as may be prepared by reaction of coconut oil amine with 10 mol ethyleneoxide.
  • EXAMPLE 3 A mixed fabric made of polyester and'wool is dyed at a liquor ratio of 1:30 from a dye-bath containing 2 percent (related to the weight of the fabric) of Setacylblau PRS (C.I. Disperse Blue 19; CI. No. 61110), 2 c.c.ll. of a mixture of percent perchloroethylene and 20 percent nonylphenoloxethylate with 10 oxethyl groups in the molecule. The temperature is raised in the closed apparatus within 30 minutes to 105 and dyeing is carried out during minutes at this temperature.,0btained is a blue dyeing showing good fastness properties. The dye yield obtained is substantially higher than in the case of the concurrent use of aromatic chlorinated hydrocarbons. A similar result as obtained with perchloroethylene is achieved if instead of perchloroethylene trichloroethylene or a mixture of perchloroethylene and trichloroethylene is employed.
  • Setacylblau PRS C.I. Disperse Blue 19; CI
  • E AMPLE V r A polyester fabric is dyed in a closed apparatus during 90 minutes at a liquor ratio of 1:20 from a dye-bath containing 3 percent (related to the weight of the fabric) of the finely dispersed dyestuffpf the formula A CHzCH: CN
  • the emulsifier employed is a mixture of oxethylated coconut oil amine (with ethoxyl groups in the molecule) and stearylalcohol oxethylate (with 8 ethoxyl groups in the molecule).
  • a cellulose triacetate fabric is heated to 105 during 25 minutes in a dye-bath at a liquid ratio of 1:20, the bath containing 2.5 percent (related to the weight of the fabric) Resolinrubin BL (Disperse Violet 40) and 3 c.c./l. of a mixture of 85 percent perchloroethylene and percent emulsifier. Subsequently, it is dyed for 60 minutes at this temperature. As compared with a dyeing without the addition of perchloroethylene one obtains a substantially deeper shade as well as a markedly better appearance of the fabric.
  • the emulsifier employed is a mixture of oxethylated castor oil (prepared from castor oil and 36 mols ethyleneoxide), calcium dodecylbenzenesulfonate and isobutanol at a weight ratio of 3:2:1.
  • the emulsifier employed is a mixture of oxethylated castor oil (with 36 mols ethyleneoxide), calcium dodecylbenzenesulfonate and isobutanol at a weight ratio of 312:1.
  • a process for dyeing a polyester or cellulose triacetate textile material which comprises dyeing said textile material under pressure and at a temperature above 100C. with an aqueous dyebath containing dispersed trichloroethylene, perchloroethylene or a mixture thereof, as carrier, in an amount of 0.5-10 c.c./l., an emulsifier and dispersed dye.
  • said emulsifier is a mixture of oxethylated castor oil and calcium dodecylbenzene sulfonate.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Polyesters Or Polycarbonates (AREA)
US00205718A 1970-12-09 1971-12-07 Process for dyeing textiles made of polyester or cellulose triacetate Expired - Lifetime US3776690A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702060565 DE2060565C3 (de) 1970-12-09 Verfahren zum Färben von Textilien aus Polyester oder Zellulose-Triacetat

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US3776690A true US3776690A (en) 1973-12-04

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US00205718A Expired - Lifetime US3776690A (en) 1970-12-09 1971-12-07 Process for dyeing textiles made of polyester or cellulose triacetate

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US (1) US3776690A (enrdf_load_stackoverflow)
AT (1) AT326082B (enrdf_load_stackoverflow)
AU (1) AU449838B2 (enrdf_load_stackoverflow)
BE (1) BE776478A (enrdf_load_stackoverflow)
CA (1) CA968506A (enrdf_load_stackoverflow)
CH (2) CH1789071A4 (enrdf_load_stackoverflow)
FR (1) FR2117940B1 (enrdf_load_stackoverflow)
GB (1) GB1316720A (enrdf_load_stackoverflow)
IT (1) IT943771B (enrdf_load_stackoverflow)
NL (1) NL7116298A (enrdf_load_stackoverflow)
ZA (1) ZA718225B (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926554A (en) * 1972-11-10 1975-12-16 Brueckner Apparatebau Gmbh Method of dyeing textile material made of synthetic fibres
US4348203A (en) * 1973-05-05 1982-09-07 Ciba-Geigy Corporation Dyeing process

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US119187A (en) * 1871-09-19 Improvement in processes for treating textile fabrics with hydrocarbons
US290110A (en) * 1883-12-11 With hydrocarbons
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US119187A (en) * 1871-09-19 Improvement in processes for treating textile fabrics with hydrocarbons
US290110A (en) * 1883-12-11 With hydrocarbons
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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926554A (en) * 1972-11-10 1975-12-16 Brueckner Apparatebau Gmbh Method of dyeing textile material made of synthetic fibres
US4348203A (en) * 1973-05-05 1982-09-07 Ciba-Geigy Corporation Dyeing process

Also Published As

Publication number Publication date
GB1316720A (en) 1973-05-16
CH555938A (enrdf_load_stackoverflow) 1974-11-15
FR2117940B1 (enrdf_load_stackoverflow) 1976-06-04
DE2060565A1 (de) 1972-06-22
AU449838B2 (en) 1974-06-20
DE2060565B2 (de) 1977-02-03
CA968506A (en) 1975-06-03
FR2117940A1 (enrdf_load_stackoverflow) 1972-07-28
CH1789071A4 (enrdf_load_stackoverflow) 1974-06-14
ZA718225B (en) 1972-08-30
ATA1051071A (de) 1975-02-15
IT943771B (it) 1973-04-10
NL7116298A (enrdf_load_stackoverflow) 1972-06-13
BE776478A (fr) 1972-06-09
AT326082B (de) 1975-11-25
AU3661671A (en) 1973-06-14

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