US3846070A - Process for the dyeing of polyester textile materials - Google Patents

Process for the dyeing of polyester textile materials Download PDF

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Publication number
US3846070A
US3846070A US00211727A US21172771A US3846070A US 3846070 A US3846070 A US 3846070A US 00211727 A US00211727 A US 00211727A US 21172771 A US21172771 A US 21172771A US 3846070 A US3846070 A US 3846070A
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United States
Prior art keywords
dyeing
water
parts
dyebath
polyester textile
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Expired - Lifetime
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US00211727A
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English (en)
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W Langmann
R Kuth
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Bayer AG
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Bayer 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
    • D06P1/922—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
    • Y10S8/90—Basic emulsifiers for dyeing
    • 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
    • Y10S8/903—Triple mixture of anionic, cationic, and nonionic emulsifiers for dyeing
    • 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
    • Y10S8/904—Mixed anionic and nonionic emulsifiers for dyeing
    • 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
    • Y10S8/905—Mixed anionic and cationic emulsifiers for dyeing
    • 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
    • Y10S8/907—Nonionic emulsifiers for dyeing
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/91—Soap
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/912—Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
    • 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

Definitions

  • the invention relates to a process for the dyeing of polyester textile materials with disperse dyestuffs; more particularly it concerns an exhaust process for the dyeing of polyester textile materials with disperse dyestuffs from organic water-immiscible solvents, which is characterised in that dyebaths of organic water-immiscible solvents are used which contain, besides the disperse dyestuffs, (a) water-soluble anionic dispersing agents and (b) cationic and/or non-ionic tensides.
  • Suitable organic water-immiscible solvents are solvents the boiling point of which lies between 40' and 150 C., e.g. aromatic hydrocarbons such as toluene and xylene; aliphatic halogenated hydrocarbons, especially chlorinated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, t-etrachloroethane, dichloropropane, chlorobutane and dichlorobutane; aliphatic fluorinated and fiuoro-chlorinated hydrocarbons such as perfiuoro-n-hexane, 1,2,2- trifluoro-trichloroethane, and trifluoro-pentachloropropane; aromatic chlorinated and fiuorinated hydrocarbons such as chlorobenzene, fluorobenzene, chlorotoluene and benzo-trifiuoride.
  • Tetrachloroethylene, trichloroethylene, 1,1,1-trichloroethane and 1,1,1-trichloropropane have proved particularly satisfactory. Mixtures of these solvents can also be used.
  • the disperse dyestuffs used for the dyeing process according to the invention are disperse dyestuffs conventionally used for dyeing polyesters and cellulose esters, such as are described, for example, in Colour Index, vol. 1, pp. 1655-1742, 2nd edition (1956). It must be emphasized that the term disperse dyestuffs also refers to optical brightening agents. Disperse brightening agents of this 'kind are described, for example, in H. Hefti, Textilveredelung 4 (1969), Pp 94 seq., and in British patent specification No. 1,113,918.
  • the water-soluble anionic dispersing agents to be used according to the invention are primarily the known dispersing agents derived from aromatic sulphonic acids, for example, the condensation products of naphthalene-sulphonic acid with formaldehyde, or of cresol, B-naphtholsulphonic acid and formaldehyde; or polystyrene-sulphonic acid, or the disulphonate of heptadecyl benzimidazole; furthermore, the known dispersing agents derived from sulphite cellulose waste liquor and its reaction products with aniline.
  • These dispersing agents are described, for example, in Lindner, Tenside-Textilhesstoff-Waschrohstoffer, 2nd edition (1964), vol. I, pp. 767, 809, vol. II, p. 1585.
  • R and R independently of one another, mean hydrogen; a c -C -alkyl or C -C -alkenyl group; or a group of the formula -(C H O) R
  • R stands for hydrogen, a C C -alkyl, a phenyl or a C -C -alkyl phenyl radical
  • n stands for a number from 1 to 10
  • At least one of the radicals R, R or R contains an alkyl chain with at least 5 carbon atoms and that the total number of (C H O) units in the amine molecule is not higher than 10.
  • amines of the formula (I) are, for example: primary amines, such as pentylamine, iso-pentylamine, octylamine, 2-ethylhexylamine, decylamine, d0- decylamine, stearylamine, oleylamine, eicosylamine, docosylamine; secondary amines, such as N-methyl-pentylamine, N-butyl-Z-ethylhexylamine, N-methyl-dodecylamine, N-methyl-stearylamine, N-ethyl-oleylamine, N- methyldocosylamine; tertiary amines, such as N,N-dimethyl-pentylamine, N,N dimethyl-Z-ethylhexylamine, N,N bis (B-hydroxyethyl)-stearylamine, the reaction products of one mol stearylamine with 5 mol ethylene oxide
  • the amines of the formula (I) may also be present as quarternised compounds; representatives are, for example: N,N-dimethyl-N-benZyl-stearyl ammonium chloride, N,N,N-trimethyl-N-dodecyl ammonium metasulphate, N,N-dimethyl-N-dodecyl-N-benzyl ammonium chloride, N,N-dimethyl-N,N-distearyl ammonium chloride and N,N-dimethyl-N-benzyl-N 2 [2-(4-isooctylphenoxy) ethoxy]-ethyl ammonium chloride.
  • the cationic tensides to be used according to the invention must be soluble or at least dispersible in the organic solvents.
  • the quaternisation products frequently do not meet this requirement.
  • mixtures are obtained which are soluble or dispersible in the organic solvents and are eminently suitable as components (b) in the mixtures of auxiliaries to be used according to the invention.
  • non-ionic tensides in the mixtures of auxiliaries to be used according to the invention there may be used the known non-ionic tensides, provided they are soluble or dispersible in the organic solvents or yield with the cationic tensides mixtures which are soluble or dispersible in organic solvents.
  • the reaction products of ethylene oxide with fatty alcohols, fatty acids, fatty amines, alkylphenols and fatty acid amides have mainly proved satisfactory; furthermore, carboxylic acid amides which are free from amino groups, e.g. fatty acid monoor dialkylamides or fatty acid monoand dialkanolamides.
  • the quantitative proportions between the dyestuffs and the mixtures of auxiliaries to be used according to the invention may vary within wide limits; they depend on the type of dyestulf and can easily be established in each case by preliminary experiments. In general, 0.3 to 3 parts of the water-soluble anionic dispersing agent and 0.5 to 4 parts of non-ionic and/or cationic tenside are used for every part of dyestuif.
  • auxiliaries can be advantageous to add to the mixture of auxiliaries small amounts of lower alcohols, e.g. ethanol or butanol, and/ or water; however, the quantitative proportion of these additives should not exceed the total amount of auxiliaries (a) and (b).
  • lower alcohols e.g. ethanol or butanol
  • the dyebaths to be used according to the invention are advantageously prepared by first pasting or grinding the dyestuff with the anionic dispersing agent; subsequently adding to the resultant paste the remaining auxiliaries together with small amounts of the solvent used for dyeing; and working up all the components together to form a homogeneous mixture. The latter is subsequently diluted to the desired concentration by the addition of more solvent.
  • Dyeing of the polyester textile materials in the baths so obtained is carried out in known manner by introducing the textile materials into the dyebath at to 60 C., heating the bath to 100 to 120 C., and dyeing at the same temperature until the desired depth of colour has been attained. The dyed textile material is then rinsed with fresh solvent, first hot, then cold, and subsequently dried.
  • dyebaths to be used according to the invention are not prepared with the use of pure disperse dyestuffs, but with commercial disperse dyestuffs, i.e. those formulated with anionic dispersing agents, these dyestuffs may immediately be worked up together with the nonionic and/or cationic tensides to form the homogeneous mixture which can be diluted with the organic solvents.
  • the polyesters primarily comprise polyethylene terephthalates, polycyclohexane-dimethylene terephthalate, or polycarbonates of 2,2-bis-(phyd'roxyphenyl)-propane, and cellulose triacetate.
  • the materials may be present in various stages of processing, e.g. as filaments, yarn, fabrics, knitted fabrics, or ready-made goods.
  • the advantage of the process according to the invention over the known processes for the dyeing of polyester materials from organic water-immiscible solvents consists in a higher exhaustion of the bath within a shorter period of time that is to say that a higher dyeing speed is achieved. Furthermore, the process according to the invention offers the advantage of permitting of the use of the commercial disperse dyestuffs formulated for dyeing from aqueous baths and is not subject to the use of pure dyestuffs.
  • water-soluble anionic dispersing agents are not suitable for dispensing non-ionic dyestuffs in organic water-immiscible solvents because they are insoluble in these solvents. It is further known that although nonionic and/or cationic tensides can be used as auxiliaries for dyeing polyester materials from organic water-immis proficient solvents, their effectiveness in furthering the drawing of the dyestuff is unsatisfactory.
  • auxiliaries which cannot be used as such for the dyeing from organic waterirnmiscible solvents, with auxiliaries whose effectiveness in this dyeing process is unsatisfactory should lead to a mixture of auxiliaries enabling very level dyeings to be obtained not only with excellent dyestuff yields but also in shorter dyeing times.
  • the parts used in the examples are parts by weight.
  • EXAMPLE 1 1 part of the dyestuff of the formula OH O OH is ground in a ball mill with 1 part of the sodium salt of formaldehyde (prepared according to Can. patent speci- 4 the reaction product of B-naphthalene-sulphonic acid and fication No. 347,865) and 1 part of water. 3 parts of this mixture are stirred with 1 part of the emulsifier mixture described below in 10 parts perchloroethylene and then diluted with 1600 parts of the same solvent.
  • formaldehyde prepared according to Can. patent speci- 4 the reaction product of B-naphthalene-sulphonic acid and fication No. 347,865
  • a fabric of polyethylene glycol terephthalate is introduced in a liquor ratio of 1:20 into the dyebath so prepared.
  • the dyebath is heated in a closed dyeing vessel to 120 C. and this temperature is maintained for 1 hour.
  • the fabric is subsequently rinsed with warm and then with cold perchloroethylene, and then dried. A deep and level blue dyeing of the fabric is obtained.
  • the emulsifier mixture used above had been prepared by mixing 1 part oleic acid ethanolamide, 1 part of the reaction product of 20 mol ethylene oxide with 1 mol oleyl alcohol and 1 part of water.
  • the quantity of dyestuff absorbed by the polyester fabric amounts to 5.2 mg./ g. fabric.
  • EXAMPLE 2 1 part of the dyestuff of the formula H OH 0 is stirred with 2 parts of the reaction product of 2 mol naphthalene-sulphonic acid and 1 mol formaldehyde, and with 8 parts dodecylamine and 10 parts perchloroethylene. The mixture is subsequently diluted with 1600 parts of the solvent.
  • EXAMPLE 3 1 part of the dyestuff of the formula CH7CHCN is ground in a ball mill with 2 parts of a product prepared from a sulphite-cellulose waste liquor product and aniline, and with 1 part isobutanol. 5 parts of this mixture are stirred with 2 parts nonylphenol decaethylene glycol ether and 20 parts perchloroethylene, and diluted with a further 800 parts perchloroethylene.
  • EXAMPLE 4 6 parts of the dyestuff of the formula CH CH;4O oooHi N CHz-CHz-O C CH3 are worked up with 5 parts of the Water-soluble dispersing agent described in Example 3, 5 parts of the 1:1:1 reaction product of cresol, ,B-naphthalene-sulphonic acid and formaldehyde (sodium salt) and 4 parts of water to form a paste. 7 parts of this paste are stirred with 10 parts of the reaction product of 10 mol ethylene oxide and 1 mol hexadecylamine, 3 parts isobutanol and 40 parts perchloroethylene, and subsequently diluted with 1600 parts of the solvent.
  • Dyeing is carried out with this dyebath as described in Example 1. A brilliant red dyeing is obtained on the polyester fabric.
  • EXAMPLE 5 1 part of the dyestuff of the formula is ground in a ball mill With 2 parts of the sodium salt of lignin-sulphonic acid and 1 part isobutanol. 5 parts of this mixture are diluted with 2 parts hexadecylamine and parts perchloroethylene, and subsequently diluted with a further 800 parts perchloroethylene.
  • polyester fabric 50 parts are dyed in the dyebath so prepared, as described in Example 1. A level brilliant yellow dyeing is obtained on the polyester fabric.
  • Process for dyeing polyester textile material comprising the steps of (1) immersing the polyester textile material in a nonaqueous dyebath consisting essentially of (a) water-immiscible organic solvent having a boiling point of 40 C.150 C.;
  • the cationic dispersing agent (d) is an amine or the quaternization product thereof said amine having the formula in which R is C -C -alkyl or C -C -alkenyl; R and R independently of one another, are hydrogen; C C alkyl; C C -alkenyl; or --(C H O) R where R is hydrogen, C C -alkyl, phenyl or C C -alkylphenyl; and n is a number from 1 to 10; with the proviso that at least one of the radicals R, R or R contains an alkyl chain with at least 5 carbon atoms, and that the total number of (C H O)- units in the amine molecule is not greater than 10.
  • non-ionic dispersing agent (d) is the reaction product of ethylene oxide with fatty alcohol, fatty acid, fatty amine, alkylphenol or fatty acid amide; or amino group-free carboxylic acid amides; which are soluble or dispersible, or are soluble or disersible in mixture with the cationic dispersing agent, in the organic solvents.
  • Claim 1 is conducted by immersing the polyester textile material in said dyebath at 20 C. 60 C., heating the dyebath to C. C. and maintaining the dyebath at 100 C.-120 C. until the desired depth of color has been achieved.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US00211727A 1970-12-23 1971-12-23 Process for the dyeing of polyester textile materials Expired - Lifetime US3846070A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702063330 DE2063330A1 (de) 1970-12-23 1970-12-23 Verfahren zu Färben von Polyester-Textilmaterialien

Publications (1)

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US3846070A true US3846070A (en) 1974-11-05

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US00211727A Expired - Lifetime US3846070A (en) 1970-12-23 1971-12-23 Process for the dyeing of polyester textile materials

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US (1) US3846070A (enrdf_load_stackoverflow)
BE (1) BE777231A (enrdf_load_stackoverflow)
CH (2) CH560798A (enrdf_load_stackoverflow)
DE (1) DE2063330A1 (enrdf_load_stackoverflow)
FR (1) FR2119076B1 (enrdf_load_stackoverflow)
GB (1) GB1318810A (enrdf_load_stackoverflow)
IT (1) IT945565B (enrdf_load_stackoverflow)
NL (1) NL7117521A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065259A (en) * 1974-05-03 1977-12-27 E. I. Du Pont De Nemours And Company Fluorocarbon dye dispersion for exhaust disperse dyeing
US4115057A (en) * 1975-10-30 1978-09-19 Montedison S.P.A. Process for the dyeing of fibrous materials containing basic functions in dyeing baths based on organic solvents
US4220449A (en) * 1974-03-08 1980-09-02 Sandoz Ltd. Quaternated polyamine salts
US5112370A (en) * 1989-12-13 1992-05-12 Michele Gazzano Device for sterilizing a forced air flow by means of ultraviolet radiations

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1535352A (fr) * 1966-09-01 1968-08-02 Henkel & Cie Gmbh Procédé de teinture d'une matière fibreuse dans des solvants organiques

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4220449A (en) * 1974-03-08 1980-09-02 Sandoz Ltd. Quaternated polyamine salts
US4065259A (en) * 1974-05-03 1977-12-27 E. I. Du Pont De Nemours And Company Fluorocarbon dye dispersion for exhaust disperse dyeing
US4115057A (en) * 1975-10-30 1978-09-19 Montedison S.P.A. Process for the dyeing of fibrous materials containing basic functions in dyeing baths based on organic solvents
US5112370A (en) * 1989-12-13 1992-05-12 Michele Gazzano Device for sterilizing a forced air flow by means of ultraviolet radiations

Also Published As

Publication number Publication date
NL7117521A (enrdf_load_stackoverflow) 1972-06-27
CH560798A (enrdf_load_stackoverflow) 1975-04-15
DE2063330A1 (de) 1972-07-06
IT945565B (it) 1973-05-10
CH1864971A4 (enrdf_load_stackoverflow) 1974-11-15
GB1318810A (en) 1973-05-31
FR2119076B1 (enrdf_load_stackoverflow) 1975-08-29
FR2119076A1 (enrdf_load_stackoverflow) 1972-08-04
BE777231A (fr) 1972-06-23

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