US3894840A - Process for the single-bath dyeing of unmodified polyolefin fibers with metal complex dyestuffs - Google Patents

Process for the single-bath dyeing of unmodified polyolefin fibers with metal complex dyestuffs Download PDF

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Publication number
US3894840A
US3894840A US336904A US33690473A US3894840A US 3894840 A US3894840 A US 3894840A US 336904 A US336904 A US 336904A US 33690473 A US33690473 A US 33690473A US 3894840 A US3894840 A US 3894840A
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United States
Prior art keywords
dyestuffs
dyeing
dyestuff
steaming
metal
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Expired - Lifetime
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US336904A
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English (en)
Inventor
Der Eltz Hans-Ulrich Von
Armand Lehinant
Hans-Peter Maier
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Hoechst AG
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Hoechst AG
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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
    • 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
    • D06P3/79Polyolefins
    • D06P3/795Polyolefins using metallisable or mordant dyes, dyeing premetallised fibres
    • 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
    • D06P1/60General 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 polyethers
    • D06P1/613Polyethers without nitrogen
    • D06P1/6131Addition products of hydroxyl groups-containing compounds with oxiranes
    • 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
    • D06P1/673Inorganic compounds
    • D06P1/67333Salts or hydroxides
    • D06P1/67341Salts or hydroxides of elements different from the alkaline or alkaline-earth metals or with anions containing those elements
    • 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
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/928Polyolefin fiber

Definitions

  • ABSTRACT Process for the single-bath dyeing or printing of unmodified polyolefin fibers with metal-complex dyestuffs, by reacting under high-temperature dyeing conditions on these textile materials aqueous liquors or printing pastes containing water-s0lub1e or dispersed metallizable dyestuffs and compounds yielding polyvalent heavy-metal ions in the presence of a dispersion system on the basis of polyglycol ethers.
  • the present invention relates to a process for the single-bath dyeing f unmodified polyolefin fibers with metal complex dyestuffs.
  • unmodified polyolefin fibers for example, polypropylene fibers
  • polypropylene fibers are, generally, difficult to dye by direct dyeing methods.
  • the dyeing of piece goods made of such fibers with aqueous suspensions of pigment dyestuffs and curable binding systems is described which form a correspondingly coloured film layer fast to washing on the fiber surface when being heated.
  • Disperse dyes used for dyeing polyester fibers and other hydrophobic fibers yield under comparable thermal conditions only very fair dyeings when being fixed the yield of which is unproportioned with respect to the amount of dyestuff used.
  • polystyrene resin Various methods for the modification of the polyolefin material allow to improve the dye receptivity of the fiber considerably.
  • nitrogen-containing copolymers having a basic effect are introduced into the spinning melt of the fibrous ground substance of which the fibers consist and so anchored in the macromolecule.
  • the fibers, so modified then have affinity towards the anionic dyestuffs.
  • Polypropylene can also be modified in such a manner that compounds of such metals which can form fast colour lakes with metallizable dyestuffs are incorporated into the mass or fiber.
  • the fiber properties are influenced either by a metal-containing copolymer or by special aftertreatment operations of the finished, unmodified fibrous material before dyeing, for example, as described in German Auslegeschriften Nos.
  • unmodified polyolefin fibers preferably polypropylene fibers
  • metal complex dyestuffs when allowing aqueous liquors or printing pastes containing water-soluble or dispersed, metallizable dyestuffs and compounds yielding polyvalent heavy-metal ions to act, under high-temperature dyeing conditions, on these textile materials in the presence of a dispersion system on the basis of polyglycol ethers.
  • the present invention is based on the observation that when using metallizable dyestuffs and metallizing agents in the same bath in the presence of a certain dispersion system the colour lake formed in the liquid is obtained in a particular colloidal state of dispersion in which it shows a technically useful affinity towards the unmodified polyolefin fiber under suitable thermal conditions.
  • the dyeings or prints can be effected according to the process claimed using the exhaustion method, the pad-steaming method or a printing method together with steam fixation of the dyes.
  • the exhaustion method requires temperatures within the range of from 120 to 135C, preferably about 130C, and a period of action of 40 to 70 minutes, preferably about 60 minutes; the
  • pad-steaming and the print steaming method require temperatures within the range of from C to C, preferably about 130C, and a period of action of from 10 to 40 minutes, preferably about 30 minutes. These temperatures suggested are, while maintaining a technical safety zone, below the range of temperature (from to C) at which the polyolefin (or polypropylene) fiber melts.
  • the metal-free dyestuff and the second component necessary for the formation of the colour lakes, the metallizing agent are applied from a liquor, i.e. at the same time and according to the single-bath method, in order to enable the formation of the metal complex compound under determined conditions.
  • the dyeing of metal-modified polypropylene fibers also leads to the formation of the colour lakes from the dyestuff and the metallizing agent contained in the fiber, this process can, at best, take place at the fiber surface, ie at the places where a metal ion is situated on the metal-modified fiber. As the metal is in these cases placed in the external layer of the fiber, the dyestuff can no longer be deposited in the internal part of the fiber.
  • the colour lake is, however, formed outside the fibers in the liquor.
  • those colour lakes are necessarily water-insoluble, a dispersion system is required which maintains the colour lake formed in a suitable state of dispersion allowing a diffusion into and, thus, an absorption of the metal complex dyestuff by the fiber.
  • This dispersion system essentially consists of a nonionic auxiliary on the basis of alkyl or alkylaryl-polyglycol ethers or oxethylated fatty acid polyglycol esters, preferably a reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide, which is combined in the exhaustion method with anionic protective colloids having a dispersing effect, preferably those on the basis of ligninsulfonic acid, and in the pad-steaming or printsteaming method with non-ionic protective colloids having a thickening effect, preferably a completely etherified locust bean flour.
  • the metallizable dyestuffs to be used for carrying out the dyeings according to the novel method may be watersoluble (mordant dyestuffs) or water-insoluble (metallizable disperse dyestuffs). Chemically spoken, these types of dyestuffs are compounds which form a coordinative complex with polyvalent metal atoms because of determined constitutional conditions, the metal being linked partially by a principal, partially by a secondary valency. These dyestuffs are products selected from different chemical classes of compounds.
  • dyestuffs of different categories of compounds are suitable which contain an o-hydroxycarbonyl-group (for example o-hydroxyanthraquinones) or a o-hydroxycarboxyl-group (for example salicylic acid derivatives) or which contain in orthoor peri-position two hydroxyl groups or one hydroxy and one carboxyl group (for example alizarines).
  • Dyestuffs of the type disclosed above are described in detail in literature.
  • Suitable metallizing agents are, according to the invention, compounds of chromium, copper, iron, cobalt, nickel, zinc and aluminium which split off corresponding metal ions, especially under heat without having a negative influence on the bath stability, for example, by the formation of hydroxides, for example, salts of organic or inorganic acids, such as chelates relatively unstable under the action of heat of these metal ions forming colour lakes with nitriloacetates, ethylenediaminetetraacetates, polyphosphates, tartrates, citrates or with aliphatic amines, especially triethanol amine, or also with ammonia.
  • hydroxides for example, salts of organic or inorganic acids, such as chelates relatively unstable under the action of heat of these metal ions forming colour lakes with nitriloacetates, ethylenediaminetetraacetates, polyphosphates, tartrates, citrates or with aliphatic amines, especially triethanol amine, or also with am
  • mordant dyestuffs metallizable with chromium are especially important because of the fact that their colour lakes yield fat dyeings of pleasant shades.
  • the chromium (lIl)-acetato-sulfate used in accordance with the invention is of outstanding importance. It has the following formula:
  • Flock material of unmodified polypropylene fibers was dyed in a dyeing apparatus under high-temperature conditions, with a goods-to-liquor ratio of l 20, for 60 minutes at 130C with an aqueous liquid which contained, calculated on the weight of the dry material, the following components:
  • the dyeing was carried out in an analogous manner as described in Example 1, using, however 2 of the mordant dyestuff of the formula Ho 0 NH A brilliant, fast green dyeing was obtained.
  • Dyeing was carried out as described in Example 1, using, however, an aqueous liquid of a dispersed azo pigment which was formed by diazotizing and coupling 1 percent of the aromatic primary amine 6-chloro-3- amino-indazole with the Azoic Coupling Component 12- C.I.No. 37.550 and containing as metallizing agent the following combination of chemicals:
  • a dyeing was prepared in an analogous manner as described in Example 1, using, however 2 percent of the disperse dye of the formula Ho '0' on" l HO O CHg-CHg-CHg-CHn described in German Auslegeschrift No. 1,619,601 in Example 12 and as metallizing agent a combination of 1 percent of nickel (ll)-sulfate-hexahydrate, 3 percent of sodium-nitrilotriacetate, 1 percent of the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide and 5 percent of an anionic protective colloid on the basis of lignin-sulfonic acid. A fast blue dyeing was obtained.
  • Piece-goods of unmodified polypropylene fibers were padded, with a liquor-pick up of percent by weight, with an aqueous liquid at room temperature which contained per liter 20 g of the mordant dyestuff mentioned in Example 20 g of chromium (lll)- acetate-sulfate,
  • a process for the single-bath dyeing or printing of unmodified polypropylene fibers with metal-complex dyestuffs which comprises: reacting under hightemperature dyeing conditions above C on these textile materials aqueous liquors or printing pastes containing dispersed metallizable dyestuffs and compounds yielding polyvalent heavy-metal ions capable of forming color lakes in the presence of a dispersion system based upon polyglycol ethers or esters.
  • polyphosphates tartrates, citrates, triethanol amine or with ammonia are used.
  • anionic protective colloids having a dispersing effect based upon lignin-sulfonic acid, in combination with a non-ionic auxiliary based upon the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide are used.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
US336904A 1972-03-07 1973-03-01 Process for the single-bath dyeing of unmodified polyolefin fibers with metal complex dyestuffs Expired - Lifetime US3894840A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2210878A DE2210878C3 (de) 1972-03-07 1972-03-07 Verfahren zum einbadigen Färben von Textilmaterialien aus unmodifizierten Potyolefinfasern mit Metallkomplexfarbstoffen

Publications (1)

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US3894840A true US3894840A (en) 1975-07-15

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US (1) US3894840A (US07579456-20090825-P00002.png)
JP (1) JPS4899472A (US07579456-20090825-P00002.png)
CH (2) CH561328A (US07579456-20090825-P00002.png)
DE (1) DE2210878C3 (US07579456-20090825-P00002.png)
GB (1) GB1418795A (US07579456-20090825-P00002.png)
IT (1) IT981124B (US07579456-20090825-P00002.png)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4300900A (en) * 1977-04-19 1981-11-17 Ciba-Geigy Corporation Process and dye preparations for pad-dyeing
US20060106173A1 (en) * 2002-10-11 2006-05-18 Basf Aktiengesellschaft Polymeric derivatives for permanently modifying hydrophobic polymers

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097044A (en) * 1960-04-04 1963-07-09 Geigy Chem Corp Process for coloring polypropylene
US3362781A (en) * 1964-05-15 1968-01-09 Kuhlmann Ets 7-(2', 5'-dichlorophenylazo)-6-methyl-8-hydroxy-quinoline dyeing of metallized polyolefin fibers
US3515506A (en) * 1964-09-02 1970-06-02 Eastman Kodak Co Polypropylene dyed with metal complexes of azo compounds
US3556709A (en) * 1964-05-15 1971-01-19 Ugine Kuhlmann Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097044A (en) * 1960-04-04 1963-07-09 Geigy Chem Corp Process for coloring polypropylene
US3362781A (en) * 1964-05-15 1968-01-09 Kuhlmann Ets 7-(2', 5'-dichlorophenylazo)-6-methyl-8-hydroxy-quinoline dyeing of metallized polyolefin fibers
US3556709A (en) * 1964-05-15 1971-01-19 Ugine Kuhlmann Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed
US3515506A (en) * 1964-09-02 1970-06-02 Eastman Kodak Co Polypropylene dyed with metal complexes of azo compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4300900A (en) * 1977-04-19 1981-11-17 Ciba-Geigy Corporation Process and dye preparations for pad-dyeing
US20060106173A1 (en) * 2002-10-11 2006-05-18 Basf Aktiengesellschaft Polymeric derivatives for permanently modifying hydrophobic polymers
US7498386B2 (en) 2002-10-11 2009-03-03 Basf Se Derivatives of polymers for permanent modification of hydrophobic polymers

Also Published As

Publication number Publication date
CH314673A4 (US07579456-20090825-P00002.png) 1974-11-15
DE2210878A1 (de) 1973-09-20
CH561328A (US07579456-20090825-P00002.png) 1975-04-30
GB1418795A (en) 1975-12-24
DE2210878B2 (de) 1977-10-20
IT981124B (it) 1974-10-10
DE2210878C3 (de) 1978-06-15
JPS4899472A (US07579456-20090825-P00002.png) 1973-12-15

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