US3663161A - Process for continuous dyeing polyacrylonitrile textile material for a hydrophobic solvent dyebath - Google Patents

Process for continuous dyeing polyacrylonitrile textile material for a hydrophobic solvent dyebath Download PDF

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Publication number
US3663161A
US3663161A US837926A US3663161DA US3663161A US 3663161 A US3663161 A US 3663161A US 837926 A US837926 A US 837926A US 3663161D A US3663161D A US 3663161DA US 3663161 A US3663161 A US 3663161A
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United States
Prior art keywords
dyestuff
textile material
dyeing
solvent
amino group
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Expired - Lifetime
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US837926A
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English (en)
Inventor
Alfred Litzler
Visvanathan Ramanathan
Gert Hegar
Eugen Johann Koller
Branimir Milicevic
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BASF Schweiz AG
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Ciba AG
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Classifications

    • 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
    • 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
    • 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
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • ABSTRACT A process for dyeing textile material based on aromatic polyester fibers or acrylic fibers, wherein the textile material is impregnated with a solution containing at least one basic disperse dyestufi in an organic solvent and the dyestufi is fixed on the fiber by heat.
  • An advantage of the use of an organic solvent as the dyeing medium is the substantially improved uniformity of the dyed material, especially its improved uniformity of the over the whole surface.
  • the present process has the advantage that it results in less waste water.
  • Another advantage of the process of the invention over conventional dyeing with aqueous dyestuff dispersions is the possibility of using unconditioned disperse dyestuffs, whereas when dyeing by the conventional process from an aqueous dyebath it is always necessary to use conditioned dyestuff preparations to facilitate their dispersion in water.
  • the present invention provides a process for dyeing textile material based on hydrophobic polymers containing polar groups, ready for weaving, wherein the textile material is impregnated or printed, preferably padded, with a solution of at least one basic disperse dyestuff in at least one hydrophobic or in at least one hydrophilic solvent; the hydrophilic solvent concerned may contain up to 99 percent by weight of a hydrophobic component and must remain inert towards the textile material even at the dyeing temperature. To fix the dyestuff on the fiber the textile material is then subjected to a heat treatment at a temperature below the softening point of the fibrous material.
  • the present process is applicable to all fully synthetic, hydrophobic fibers containing polar groups, for example, to fibers of polyurethanes and polyamide fibers, for example, nylon 6, nylon 6.6 and nylon l l, fibers of aromatic polyesters, for example those of terephthalic acid and ethyleneglycol or l,4-dimethylolcyclohexane, or copolymers of terephthalic acid or isophthalic acid and ethyleneglycol, and especially acrylic or acrylonitrile fibers of polyacrylonitrile or of copolymers of acrylonitrile and other vinyl compounds, for example, acrylic esters, acrylamides, vinylpyridine, vinylchloride or vinylidene-chloride, copolymers of dicyanoethylene and vinyl acetate or of acrylonitrile block copolymers.
  • polyurethanes and polyamide fibers for example, nylon 6, nylon 6.6 and nylon l l
  • fibers of aromatic polyesters for example those of terephthalic
  • hydrophobic solvents that are at most only partially miscible with water, for example, acetophenone, cyclohexanol, benzyl alcohol, esters, for example, ethyl acetate, propylacetate, butyl acetate; hydrocarbons, for example, benzene, xylene or toluene and halogenated hydrocarbons, for example, carbon tetrachloride, chloroform, methylenechloride, trichloroethylene, perchloroethylene, trichloroethane, tetrachloroethane, dibromoethylene or chlorobenzene.
  • hydrocarbons for example, benzene, xylene or toluene
  • halogenated hydrocarbons for example, carbon tetrachloride, chloroform, methylenechloride, trichloroethylene, perchloroethylene, trichloroethane, tetrachloroethane
  • Water-miscible hydrophilic solvents which boil preferably above 70 C, especially above 100 C but not at a temperature of greater than 220 C, form a preferred group of solvents, including for example aliphatic alcohols, for example, methanol, ethanol, n-propanol, isopropanol, ketones, for example, acetone, methylethylketone, cyclohexanone, ethers and acetals for example, diisopropyl ether, diphenylene oxide,
  • glycol derivatives for example, ethyleneglycol mono-methyl, -ethyl and -butyl ethers and diethyleneglycolmono-methyl or -ethyl ether, thiodiglycol, polyethyleneglycols insofar as they are liquid at room temperature, ethylenecarbonate, 'y-butyrolactone and especially the group of watermiscible active solvents boiling at a temperature of greater than 120 C, for example, N,N-dimethylformamide, N,N- dimethylacetamide, bis-(dimethylamido)-methanephosphate, tris-(dimethylamido)-phosphate, N-methylpyrrolidone, 1,5- dimethylpyrrolidone, N,N-dimethylmethoxy acetamide, N,N,N',N-tetramethylurea, tetramethylenesulphone (
  • hydrophilic solvents suitable for use in the present invention there are three preferred subgroups, namely (1) those which can dissolve linear, spinnable, fully synthetic polymers or polycondensates such, for example, as acrylonitrile polymers; (2) the group of the solvents miscible with water in any desired proportion and (3) the group of solvents free from hydroxyl groups.
  • Any sulphur atom present in a solvent is preferably divalent or hexavalent.
  • solvents capable of dissolving polyacrylonitrile When solvents capable of dissolving polyacrylonitrile are to be used for dyeing acrylic fibers, they must of course be admixed with a sufficient quantity of non-solvents to prevent dissolution of or damage to the acrylic fiber, or else the contact time in the continuously performed process is kept so short that the fiber swells at most only on its surface.
  • a mixture of solvents When a mixture of solvents is to be used, it may consist of two or more hydrophobic or of two or more hydrophilic constituents.
  • hydrophilic and hydrophobic solvents which are compatible with each other, it may contain up to 99 percent, preferably at least 50 percent by weight of the hydrophobic constituent.
  • the hydrophobic solvent will boil at a lower temperature than the hydrophilic solvent. It is, however, also possible to use solvent pairs in which the hydrophobic share has a higher boiling point than the hydrophilic solvent.
  • the hydrophobic constituent of such solvent mixtures is preferably a chlorinated hydrocarbon, especially an aliphatic chlorinated hydrocarbon, for example, perchloroethylene or trichloroethylene.
  • a preferred hydrophilic constituent is an N- alkylated amide of a lower fatty acid, for example, dimethylformamide, dimethylacetamide, N-methylpyrrolidone or tris- (dimethyl)-phosphoric acid triamide.
  • a preferred mixing ratio of chlorocarbon hydrophilic constituent is 95 to 5 to 30 percent.
  • the basic disperse dyestuffs suitable for use in the present dyeing process are free from acid groups, and do not contain any quaternary nitrogen atoms.
  • dyestuffs in the following structural groups monoazo, disazo and polyazo dyestuffs, anthraquinone, perinone, quinophthalone, nitroso, nitro, stilbene and methine dyestuffs, including the styryl, azamethine, polymethine and azostyryl dyestuffs.
  • A20 dyestuffs (6) Porinone dyestuffs-Th0 mixtures of dyestuffs of the formula.
  • Ethers of polyhydroxy compounds for example, polyoxyalkylated aliphatic alcohols, polyoxyalkylated polyols, polyoxyalkylated mercaptans and aliphatic amines, polyoxyalkylated alkylphenols and alkylnaphthols, polyoxyalkylated alkylarylmer'captans and alkylarylamines;
  • N-hydroxyalkylcarbonamides polyoxyalkylated carbonamides and sulphonamides.
  • tensides in these groups which may be advantageously used are: adducts of 8 mols of ethylene oxide with 1 mol of para-tertiaryoctylphenol, or of 15 or 6 mols of ethylene oxide with castor oil, or of 20 mols of ethylene oxide with the alcohol C l-l OH, ethylene oxide adducts with di-[aphenylethyl1-phenols, polyethylene oxide-tertiary dodecyl thioether, polyamine-polyglcol ether or adducts of 15 or 30 mols respectively of ethylene oxide with 1 'mol of the amine C, H ,,NHB2 or C l-l Nl-l Suitable mixtures with tensides have been proposed in German Specification No. 1,261,613.
  • Textile materials suitable for dyeing by the present process are primarily woven fabrics or suitable knitted fabrics or carpets of all kinds, the textile material being impregnated or printed, preferably padded, and then, to fix the dyestuff on the fiber, subjected to a heat treatment, preferably a dry heat treatment, at a temperature below the softening point of the fibrous material.
  • the treatment on the padder is carried out either at room temperature or with heating. After the dyestuff solution has been conveyed through the textile material, the latter is expressed to a content of impregnating solution of about 50 percent to 130 percent referred to the weight of the dry fibrous material.
  • the impregnated or printed material leaving the padder or the printing machine respectively is either dried for a short time in a warm current of air (heated for example to 30 to C), or it is freed from the major portion of the adhering dyestuff solution in another manner, for example by centrifugation, or it is subjected to the fixation or thermofixation without drying.
  • the thermofixation is carried out at a temperature of greater than C, preferably at a temperature of at least within the range of from to 240 C. At any rate, the temperature prevailing during the fixation must not reach the softening point of the fiber.
  • Thermofixation is carried out, for example, by steaming with saturated or unsaturated water vapor or preferably by a dry heat treatment, for example, with contact heat, by a treatment with high-frequency A.C. or by irradiation with infra-red rays.
  • thermofixing conditions that prevent the fiber being damaged, are ascertained by a simple preliminary test.
  • EXAMPLE 1 A fabric of polyacrylonitrile staple fibers (rlon regular) is padded with a cold solution of parts of the dyestuff of the formula in 1,000 parts of dimethylacetamide, then expressed to a weight increase of 67 percent referred to the weight of the fiber, dried in a current of air heated to 40 to 50 C, and then heat-set for 90 seconds at 200 C. A yellow dyeing is obtained which is fast to light and washing.
  • EXAMPLE 2 The procedure is as described in Example 1, except that Modacryl staple fiber fabric (Acrylan regular type 36) is used with a weight increase after expression of 104 percent. The resulting yellow dyeing is also fast to light and washing.
  • EXAMPLE'3 The procedure is as described in Example 1, except that a polyester staple fiber fabric (Dacron) with a weight increase of 60 percent after expression is used. The resulting dyeing is analogous to that described in Example 1.
  • EXAMPLE 4 Polyacrylonitrile staple fiber fabric is padded with a cold solution of 10 parts of the dyestuff of the formula in 1,000 parts of a mixture of 90 percent of perchloroethylene and 10 percent of dimethylacetamide, expressed to a weight increase of 103 percent, dried in a current of air heated at 40 to 50 -C and then heat-set for 90 seconds at 200 C. The resulting red-brown dyeing is fast to light and washing.
  • EXAMPLE 5 Dyeing is performed as described in Example 4, but a polyester staple fiber fabric (Dacron) is used and expressed to a weight increase of 81 percent. The resulting red-brown dyeing is fast to light and washing.
  • a polyester staple fiber fabric Dacron
  • EXAMPLE 6 Dyeing is carried out as described in Example 4, but the textile material dyed is a Modacryl staple fiber fabric (Acrylan regular type 36) the material being expressed to a weight increase of 164 percent. The resulting red-brown dyeing is fast to light and washing.
  • EXAMPLE 7 Dyeing is carried out as described in Example 6, but the textile material dyed is a polyamide staple fiber fabric (nylon 6.6)
  • EXAMPLE 8 A polyacrylonitrile staple fiber fabric (Orlon) is padded with a cold solution of 10 parts of the dyestuff of the formula H ITYHCH:
  • EXAMPLE 9 A Modacryl staple fiber fabric (Acrylan regular type 36) is dyed as described in Example 8 and then expressed to a weight increase of 171 percent. The resulting dyeing corresponds to that obtained in Example 8.
  • EXAMPLE 10 A polyester staple fiber fabric (Dacron) is dyed as described in Example 8 and expressed to a weight increase of 86 percent. A result similar to that in Example 8 is obtained.
  • EXAMPLE 1 l A polyamide staple fiber fabric (nylon 6.6) is dyed as described in Example 8 and expressed to a weight increase of 100 percent. The result obtained is similar to that described in Example 8.
  • EXAMPLE 12 A woollen fabric is padded with a cold solution of 10 parts of the dyestuff used in Example 8 in 1,000 .parts' of perchloroethylene, expressed to a weight increase of 100 percent, dried in a current of air heated at 40 to 50 C and then heat-set for 90 seconds at 200- C. The fabric is then after treated for 30 minutes in an aqueous solution of 2 parts of an adduct of 9 mols of ethylene oxide with 1 mol of nonylphenol in 1,000 parts of boiling water, whereupon a brilliant blue dyeing develops which is fast to washing.
  • EXAMPLE 14 Polyester webbing is dyed as described in Example 13. The webbing was dyed red-brown shades fast to light and washing.
  • a process for the continuous dyeing of textile material comprising polymers and copolymers of acrylonitrile which comprises padding said textile with a solution comprising at least one basic disperse dyestuff in a hydrophobic solvent which is inert towards the textile and thereafter heating the dyed textile at a temperature of from C to below the softening point of the textile fibers to fix the dye.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US837926A 1968-07-01 1969-06-30 Process for continuous dyeing polyacrylonitrile textile material for a hydrophobic solvent dyebath Expired - Lifetime US3663161A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH980768A CH526679A (de) 1968-07-01 1968-07-01 Verfahren zum kontinuierlichen Färben oder Bedrucken von Textilmaterial aus Polyacrylnitril

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US (1) US3663161A (enrdf_load_stackoverflow)
BE (1) BE735369A (enrdf_load_stackoverflow)
BR (1) BR6910363D0 (enrdf_load_stackoverflow)
CA (1) CA927055A (enrdf_load_stackoverflow)
CH (2) CH980768A4 (enrdf_load_stackoverflow)
DE (1) DE1931911A1 (enrdf_load_stackoverflow)
FR (1) FR1594323A (enrdf_load_stackoverflow)
GB (1) GB1260014A (enrdf_load_stackoverflow)
NL (1) NL6910009A (enrdf_load_stackoverflow)
SE (1) SE348773B (enrdf_load_stackoverflow)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB348383I5 (enrdf_load_stackoverflow) * 1969-09-03 1975-01-28
US3884626A (en) * 1971-03-16 1975-05-20 Ciba Geigy Ag Process for the dyeing of textile material containing amino or amide groups
US3891390A (en) * 1971-03-16 1975-06-24 American Cyanamid Co Basic dye-bath and method for dyeing acrylic fibers therewith
US3923457A (en) * 1972-10-12 1975-12-02 Hoechst Ag Mixtures of fixing auxiliaries containing novel dye carrier
US3930794A (en) * 1972-10-21 1976-01-06 Hoechst Aktiengesellschaft Process for the dyeing of synthetic fiber materials from organic solvents
US3930793A (en) * 1972-10-21 1976-01-06 Hoechst Aktiengesellschaft Process for the dyeing of synthetic fiber materials from organic solvents
US3951591A (en) * 1972-10-24 1976-04-20 Hoechst Aktiengesellschaft Process for dyeing synthetic fiber materials
US3958288A (en) * 1972-03-29 1976-05-25 Hoechst Aktiengesellschaft Process for the continuous dyeing of high quality polyester fibers
US4160760A (en) * 1977-08-22 1979-07-10 Northwestern University Process for preparing polyacrylonitrile doped with Prussion blue
US20050221070A1 (en) * 2004-04-01 2005-10-06 Uni-Charm Corporation Wiper and method for manufacturing the same
US10214836B1 (en) * 2017-08-18 2019-02-26 Glen Raven, Inc. Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same
US11767616B2 (en) 2017-08-18 2023-09-26 Glen Raven, Inc. Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2186934A1 (en) * 2008-11-14 2010-05-19 Alix 161 S.R.L. Device and method for dyeing fibres and fabrics

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3120423A (en) * 1960-11-07 1964-02-04 Crown Zellerbach Corp Process for coloring synthetic polymeric materials
US3129053A (en) * 1962-05-21 1964-04-14 Du Pont Dispersions of organic dyes and pigments in fluoroalcohols
US3510243A (en) * 1965-12-09 1970-05-05 Geigy Ag J R Process for the continuous dyeing and printing of fibre material from linear,high molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3120423A (en) * 1960-11-07 1964-02-04 Crown Zellerbach Corp Process for coloring synthetic polymeric materials
US3129053A (en) * 1962-05-21 1964-04-14 Du Pont Dispersions of organic dyes and pigments in fluoroalcohols
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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chem. Eng. News 47, No. 15, p. 46 (1969) TP11418. *
WAS White, Amer. Dyestuff Reporter, July 31, 1967, pp. 591 597 TP890 A512. *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB348383I5 (enrdf_load_stackoverflow) * 1969-09-03 1975-01-28
US3923452A (en) * 1969-09-03 1975-12-02 Ciba Geigy Ag Amine salt of a dyestuff in a ketone solution
US3884626A (en) * 1971-03-16 1975-05-20 Ciba Geigy Ag Process for the dyeing of textile material containing amino or amide groups
US3891390A (en) * 1971-03-16 1975-06-24 American Cyanamid Co Basic dye-bath and method for dyeing acrylic fibers therewith
US3958288A (en) * 1972-03-29 1976-05-25 Hoechst Aktiengesellschaft Process for the continuous dyeing of high quality polyester fibers
US3923457A (en) * 1972-10-12 1975-12-02 Hoechst Ag Mixtures of fixing auxiliaries containing novel dye carrier
US3930793A (en) * 1972-10-21 1976-01-06 Hoechst Aktiengesellschaft Process for the dyeing of synthetic fiber materials from organic solvents
US3930794A (en) * 1972-10-21 1976-01-06 Hoechst Aktiengesellschaft Process for the dyeing of synthetic fiber materials from organic solvents
US3951591A (en) * 1972-10-24 1976-04-20 Hoechst Aktiengesellschaft Process for dyeing synthetic fiber materials
US4160760A (en) * 1977-08-22 1979-07-10 Northwestern University Process for preparing polyacrylonitrile doped with Prussion blue
US20050221070A1 (en) * 2004-04-01 2005-10-06 Uni-Charm Corporation Wiper and method for manufacturing the same
US7820277B2 (en) * 2004-04-01 2010-10-26 Uni-Charm Corporation Wiper and method for manufacturing the same
US20110005676A1 (en) * 2004-04-01 2011-01-13 Uni-Charm Corporation Wiper and method for manufacturing the same
US10214836B1 (en) * 2017-08-18 2019-02-26 Glen Raven, Inc. Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same
US11767616B2 (en) 2017-08-18 2023-09-26 Glen Raven, Inc. Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same

Also Published As

Publication number Publication date
NL6910009A (enrdf_load_stackoverflow) 1970-01-05
CH526679A (de) 1972-03-15
GB1260014A (en) 1972-01-12
BE735369A (enrdf_load_stackoverflow) 1969-12-30
BR6910363D0 (pt) 1973-01-11
DE1931911A1 (de) 1970-01-15
SE348773B (enrdf_load_stackoverflow) 1972-09-11
CH980768A4 (enrdf_load_stackoverflow) 1972-03-15
CA927055A (en) 1973-05-29
FR1594323A (enrdf_load_stackoverflow) 1970-06-01

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