EP0149116A2 - Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur - Google Patents

Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur Download PDF

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Publication number
EP0149116A2
EP0149116A2 EP84114978A EP84114978A EP0149116A2 EP 0149116 A2 EP0149116 A2 EP 0149116A2 EP 84114978 A EP84114978 A EP 84114978A EP 84114978 A EP84114978 A EP 84114978A EP 0149116 A2 EP0149116 A2 EP 0149116A2
Authority
EP
European Patent Office
Prior art keywords
polyacrylonitrile
alkyl
retarder
acrylonitrile copolymers
dyeing
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.)
Withdrawn
Application number
EP84114978A
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German (de)
English (en)
Other versions
EP0149116A3 (fr
Inventor
Günther Dr. Boehmke
Karlhans Dipl.-Ing. Jakobs
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.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0149116A2 publication Critical patent/EP0149116A2/fr
Publication of EP0149116A3 publication Critical patent/EP0149116A3/fr
Withdrawn legal-status Critical Current

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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
    • D06P1/655Compounds containing ammonium groups
    • D06P1/66Compounds containing ammonium groups containing quaternary ammonium groups
    • 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
    • D06P3/70Material containing nitrile groups
    • D06P3/76Material containing nitrile groups using basic dyes

Definitions

  • the compounds (I) are prepared by known processes from unsaturated fatty acids or from mixtures of saturated and unsaturated fatty acids, for example mixtures obtained from natural fats, or from their esters or chlorides and the unsymmetrical dialkylalkylenediamines.
  • the amidamines are then again quaternized by known processes using quaternizing agents such as benzyl chloride, methyl, ethyl, butyl chloride, dimethyl and diethyl sulfate and dimethyl methane phosphoric acid.
  • quaternizing agents such as benzyl chloride, methyl, ethyl, butyl chloride, dimethyl and diethyl sulfate and dimethyl methane phosphoric acid.
  • oleic acid, soy oleic acid Suitable for palm kernel acid, poppy oil acid, sunflower oil acid, rapeseed acid and tallow fatty acid.
  • Unsymmetrical alkylated alkylenediamines for example N, N-dimethyl-ethylenediamine, NN-diethylethylenediamine, N, N-dimethyl-propylenediamine and N, N-diethyl-propylenediamine, are to be mentioned as diamines.
  • Suitable cationic dyes are dyes of the most varied classes of compounds, for example diphenylmethane, triphenylmethane and rhodamine dyes, azo or anthraquinone dyes containing onium groups, furthermore thiazine, oxazine, methine and azomethine dyes, as described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 3 Edition 1970, supplement volume p. 225 are described.
  • the required amounts of the compounds of formula (I) to be used according to the invention can easily be determined by preliminary tests. In general, amounts of about 0.25 to 2.5%, based on the weight of the dye material used, of these compounds are used.
  • Suitable Acrylnitrilmischpolymerisate are for example copolymers of Acyrlnitril with vinyl chloride, vinylidene chloride, vinyl acetate, vinyl chloroacetate, vinyl alcohol, acrylic and methacrylic acid, Acyrl and methacrylic acid esters, allyl or basi - specific vinyl compounds such as vinyl imidazole, Vinylbenzimidazol, vinylpyridine, Vinylmethylpyridin, vinylpyrimidine, the proportion provided that Co-monomers is not more than 20 percent by weight.
  • the dyeing of the polyacrylonitrile fiber materials can be carried out in the customary manner in the exhaust process by introducing the material to be dyed into an aqueous dye liquor heated to about 50-85 ° C. which contains the cationic dye, compounds of the formula (I), additions of salts such as sodium acetate or Sodium sulfate, also contains acids such as acetic acid or formic acid, then the temperature of the dyebath is raised to approximately 100 ° C. in the course of about 30 minutes and then the dyebath is kept at this temperature until it is exhausted.
  • the material to be dyed can also be pretreated at a temperature of 40-100 ° C.
  • fiber materials consisting of polyacrylonitrile or acrylonitrile-containing copolymers or containing such copolymers or copolymers, which can be present in various processing stages, for example as spun tow, sliver, flakes, threads, yarns, woven or knitted fabrics, are excellently uniform and to color in deep tones.
  • DE-A-1 127 865 discloses the use of retarders of the formula (I), in which R 1 is a saturated aliphatic hydrocarbon radical when dyeing with poly fiber materials containing acrylonitrile are known.
  • R 1 is a saturated aliphatic hydrocarbon radical when dyeing with poly fiber materials containing acrylonitrile are known.
  • a compound with R 1 C 11 H 23 b eschrie- ben.
  • ammonium compounds (I) of the present invention ß compared to the corresponding saturated derivatives have improved activity as retarder, so that one can operate with smaller amounts of auxiliaries. In general, 3-4 times the amount of saturated ammonium compound is required to achieve comparable effectiveness.
  • the dyeing curve of the dyes has a uniform slope with a constant temperature increase in the drawing phase.
  • the compounds prepared according to the following examples show a band at 6.1-6.25 p in the IR spectrum.
  • the effectiveness against the corresponding ammonium compound from stearic acid is about 3 times.
  • 250 g of palm kernel fatty acid are converted into the fatty acid amine amine using 114 g of N, N-diethylethylenediamine.
  • the quaternization is carried out by mixing with excess butyl chloride by heating in an autoclave at 100 ° C. for 1 hour, at 120 ° C. for 1 hour and at 130 ° C. for 2 hours. Excess butyl chloride is then stripped off with steam. A slightly water-soluble product is obtained.
  • Example 4 Of a substance produced by the process described in Example 4 from the coconut fat consisting of over 95% saturated fatty acid glycerides, three times the amount of the compound of Example 4 is required in order to achieve the same retarding effect.
  • Example 4 400 g of the tallow fatty acid amidamine used in Example 4 are reacted with 100 g of butyl chloride at 110 ° C. in an autoclave for 6 hours. The pressure initially increased to 2 bar drops to 0.3 bar towards the end of the reaction.
  • the quaternary compound obtained is readily soluble in water and shows an activity which is three times as great on both dry-spun and wet-spun acrylic fibers as that of the compound prepared from the correspondingly hydrogenated tallow fat.
  • Yarn made of polyacrylonitrile fibers is introduced in a liquor ratio of 1:40 into a bath heated to 80 ° C., which contains 0.06 g of a cationic dye of the formula in liters
  • a knitted fabric made from staple polyacrylonitrile fibers is introduced in a liquor ratio of 1:15 into a bath at 85 ° C., which contains 0.3 g of a dye of the formula

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP84114978A 1983-12-20 1984-12-08 Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur Withdrawn EP0149116A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3345900 1983-12-20
DE19833345900 DE3345900A1 (de) 1983-12-20 1983-12-20 Verfahren zum faerben von fasermaterialien aus polyacrylnitril oder acrylnitrilmischpolymerisaten und retarder enthaltende mittel

Publications (2)

Publication Number Publication Date
EP0149116A2 true EP0149116A2 (fr) 1985-07-24
EP0149116A3 EP0149116A3 (fr) 1985-08-14

Family

ID=6217376

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84114978A Withdrawn EP0149116A3 (fr) 1983-12-20 1984-12-08 Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur

Country Status (3)

Country Link
EP (1) EP0149116A3 (fr)
JP (1) JPS60151390A (fr)
DE (1) DE3345900A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0327379A2 (fr) * 1988-02-05 1989-08-09 CRODA INTERNATIONAL plc Humectants
WO1993002042A1 (fr) * 1991-07-18 1993-02-04 Eastman Kodak Company Sels d'ammonium quaternaires contenant un amide
WO1997034041A1 (fr) * 1996-03-11 1997-09-18 High Point Chemical Corporation Composes d'unisson biodegradables pour fibres acryliques

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2963339A (en) * 1960-12-06 Retarding and levelling agents
GB866335A (en) * 1956-07-31 1961-04-26 Ciba Ltd Process for the dyeing of fibres of polyacrylonitrile
GB969855A (en) * 1960-01-14 1964-09-16 Sandoz Ltd Process for the level dyeing of natural or synthetic polyamide fibres
JPS444609Y1 (fr) * 1965-06-18 1969-02-19
DE2430853A1 (de) * 1974-06-27 1976-01-08 Cassella Farbwerke Mainkur Ag Hilfsmittel zum egalen faerben von gebilden aus polyacrylnitril oder sauer modifizierten polyestern
DE2548009A1 (de) * 1974-10-29 1976-05-06 Ciba Geigy Ag Verfahren zum egalen faerben von langsam-, normal- und schnellziehenden polyacrylnitrilmaterialien
EP0105034A1 (fr) * 1982-09-27 1984-04-04 Ciba-Geigy Ag Adjuvant de teinture et procédé pour la teinture de fibres en matériel polyacrylonitrilique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2963339A (en) * 1960-12-06 Retarding and levelling agents
GB866335A (en) * 1956-07-31 1961-04-26 Ciba Ltd Process for the dyeing of fibres of polyacrylonitrile
GB969855A (en) * 1960-01-14 1964-09-16 Sandoz Ltd Process for the level dyeing of natural or synthetic polyamide fibres
JPS444609Y1 (fr) * 1965-06-18 1969-02-19
DE2430853A1 (de) * 1974-06-27 1976-01-08 Cassella Farbwerke Mainkur Ag Hilfsmittel zum egalen faerben von gebilden aus polyacrylnitril oder sauer modifizierten polyestern
DE2548009A1 (de) * 1974-10-29 1976-05-06 Ciba Geigy Ag Verfahren zum egalen faerben von langsam-, normal- und schnellziehenden polyacrylnitrilmaterialien
EP0105034A1 (fr) * 1982-09-27 1984-04-04 Ciba-Geigy Ag Adjuvant de teinture et procédé pour la teinture de fibres en matériel polyacrylonitrilique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DERWENT JAPANESE PATENTS REPORT, Band 8, Nr. 8, 1969, Sektion 2, Seite 3; & JP-Y-44 004 609 (MORIN KAGAKU KOGYO CO., LTD.) 25.02.1969 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0327379A2 (fr) * 1988-02-05 1989-08-09 CRODA INTERNATIONAL plc Humectants
EP0327379A3 (fr) * 1988-02-05 1991-01-09 CRODA INTERNATIONAL plc Humectants
WO1993002042A1 (fr) * 1991-07-18 1993-02-04 Eastman Kodak Company Sels d'ammonium quaternaires contenant un amide
WO1997034041A1 (fr) * 1996-03-11 1997-09-18 High Point Chemical Corporation Composes d'unisson biodegradables pour fibres acryliques

Also Published As

Publication number Publication date
DE3345900A1 (de) 1985-06-27
JPS60151390A (ja) 1985-08-09
EP0149116A3 (fr) 1985-08-14

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Inventor name: BOEHMKE, GUENTHER, DR.

Inventor name: JAKOBS, KARLHANS, DIPL.-ING.