DE1064016B - Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds - Google Patents

Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds

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Publication number
DE1064016B
DE1064016B DEF23761A DEF0023761A DE1064016B DE 1064016 B DE1064016 B DE 1064016B DE F23761 A DEF23761 A DE F23761A DE F0023761 A DEF0023761 A DE F0023761A DE 1064016 B DE1064016 B DE 1064016B
Authority
DE
Germany
Prior art keywords
polymers
copolymers
vinylidenecyanide
same
vinyl compounds
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.)
Pending
Application number
DEF23761A
Other languages
German (de)
Inventor
Walter Hees
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
Priority to DEF23761A priority Critical patent/DE1064016B/en
Publication of DE1064016B publication Critical patent/DE1064016B/en
Pending 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
    • 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
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/18Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/28Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/38Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising unsaturated nitriles as the major constituent
    • 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
    • D06P1/38General 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 reactive dyes
    • 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
    • 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
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • D06P3/241Polyamides; Polyurethanes using acid dyes

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)

Description

Es wurde gefunden, daß sich Gebilde aus Acrylnitrilpolymerisaten, Vinylidencyanidpolymerisaten bzw. aus Mischpolymerisaten derselben mit anderen Vinylverbindungen in hervorragender Gleichmäßigkeit mit kätiönischen Farbstoffen färben lassen, wenn man" das- Färben in Gegenwart von quaternären Ammoniumverbindungen durchführt, die einen gegebenenfalls dufch Halogen substituierten Benzylrest und einen mindestens 8 Kohlenstoffatome aufweisenden Alkylrest enthalten.It has been found that structures made of acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds with excellent uniformity Can be dyed with Kätiönischen dyes, if one "the-dyeing in the presence of quaternary Performs ammonium compounds which have an optionally halogen-substituted benzyl radical and one having at least 8 carbon atoms Contain alkyl radical.

Geeignete qüaternäre Ammoniumverbindungen sind z. B. solche, die sich von Fettaminen ableiten, welche 8 bis 18, insbesondere 12 bis 16 Kohlenstoffatome enthalten, -und die; hieraus durch Einführung von niederen Alkylr.esteir — etwa von Methylgruppen — sowie durch anschließende Umsetzung mit Benzylchlorid oder 3,4-Dichlorbenzylchlorid erhalten sind.Suitable quaternary ammonium compounds are, for. B. those derived from fatty amines, which 8 to 18, especially 12 to 16 carbon atoms contain, -and the; from this by introducing lower alkyl groups - for example of methyl groups - as well as by subsequent reaction with benzyl chloride or 3,4-dichlorobenzyl chloride.

Wie weiterhin gefunden wurde, erzielt man hierbei besonders vorteilhafte Effekte, i wenn man die in Betracht kommenden quaternären Ammoniumverbindüngen in Form ihrer Addukte mit Harnstoff oder Harnstoffderivaten einsetzt. Solche . Addukte sind z. B. erhältlich durch Verschmelzen der quaternären Ammoniumverbindungen mit Harnstoff oder Harnstoffderivaten, wie beispielsweise Monoacetylharnstoff.As was further found, one achieves here particularly advantageous effects if one uses the quaternary ammonium compounds in question used in the form of their adducts with urea or urea derivatives. Such . Are adducts z. B. obtainable by fusing the quaternary ammonium compounds with urea or urea derivatives, such as monoacetylurea.

Die jeweils erforderlichen Mengen an den quaternären Verbindungen bzw. an ihren Harnstoffaddukte!! lassen sich durch Vorversuche leicht ermitteln; nähere Erläuterungen sind aus den nachfolgenden Beispielen ersichtlich.The respectively required amounts of the quaternary compounds or their urea adducts !! can easily be determined by preliminary tests; more detailed explanations can be found in the following examples evident.

Kationische Farbstoffe, die sich zum Färben von Gebilden aus Acrylnitrilpolymerisaten, Vinylidencyanidpolymerisaten bzw. aus Mischpolymerisaten derselben mit anderen Vinylverbindungen eignen, sind z. B. beschrieben in American Dyestuff Reporter, 1954,S.432und433.Cationic dyes, which are used for coloring structures made from acrylonitrile polymers, vinylidene cyanide polymers or from copolymers of the same with other vinyl compounds are, for. B. described in American Dyestuff Reporter, 1954, 432 and 433.

Das erfindungsgemäße Verfahren gestattet, aus den eingangs erwähnten Polymerisaten hergestellte Gebilde, wie z. B. Fäden, Fasern, Gewebe und Folien, mit kationischen Farbstoffen wesentlich gleichmäßiger zu färben, als dies in Gegenwart der bislang vorgeschlagenen Egalisierungsmittel möglich ist.The process according to the invention allows structures produced from the polymers mentioned at the outset, such as B. threads, fibers, fabrics and films, with cationic dyes much more evenly to color than is possible in the presence of the leveling agents proposed so far.

Be i s ρ i e 1 1Be i s ρ i e 1 1

Garne aus Polyacrylnitrilfasern werden im Flottenverhältnis 1 : 40 in ein 50° C warmes Bad eingebracht, welches im Liter 0,05 g des kationischen FarbstoffesYarns made from polyacrylonitrile fibers are in the liquor ratio 1:40 placed in a 50 ° C warm bath containing 0.05 g of the cationic dye per liter

H3C CH3 H 3 C CH 3

Verfahren zum Färben von aus Acrylnitrilpolymerisaten,Process for coloring acrylonitrile polymers,

VinylidencyanidpolymerisatenVinylidenecyanide polymers

bzw. aus Mischpolymerisaten derselbenor from copolymers of the same

mit anderen .Vinylverbindungenwith other vinyl compounds

hergestellten Gebildenmanufactured structures

Anmelder: , , .,;Applicant:,,.,;

Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk

Walter Hees, Köln-Höhenberg, ist als Erfinder genannt wordenWalter Hees, Cologne-Höhenberg, has been named as the inventor

sowie 0,2 Dimethyl-cetyl-benzyl-ammoniumchlorid, 0,25 g Natriumacetat und 0,2 g Eisessig enthält. Man erhöht die Temperatur der Flotte von 50° C allmählich auf 96 bis 98° C und hält das Färbebad 1 Stunde auf dieser Temperatur. Es wird eine helle Rosafärbung von ausgezeichneter Gleichmäßigkeit erzielt.as well as 0.2 dimethyl-cetyl-benzyl-ammonium chloride, Contains 0.25 g of sodium acetate and 0.2 g of glacial acetic acid. The temperature of the liquor is gradually increased from 50.degree to 96 to 98 ° C and keeps the dyebath at this temperature for 1 hour. It turns a light pink color achieved with excellent evenness.

Beispiel 2Example 2

Ein Gewebe aus Polyacrylnitrilfäden wird im Flottenverhältnis 1 : 40 in ein Bad gebracht, welches im Liter 0,1 g des kationischen FarbstoffesA fabric made of polyacrylonitrile threads is placed in a bath in a liquor ratio of 1:40, which 0.1 g of the cationic dye per liter

HaCH a C

CH,CH,

C-CH = CH-NHC-CH = CH-NH

, C Ho C Ho Cl , C Ho C Ho Cl

-n:-n:

CH, sowie 0,15 g der durch Umsetzung von Dimethyl-Palmkernfettamin mit Benzylchlorid erhaltenen quaternären Ammoniumverbindung, 0,2 g Natriumacetat und 0,3 g Eisessig enthält. Man beginnt mit dem Färben bei 60° C, erhöht die Temperatur allmählich auf 98° C und färbt hierbei in 1 Stünde zu Ende. EsCH, and 0.15 g of the reaction of dimethyl palm kernel fatty amine quaternary ammonium compound obtained with benzyl chloride, 0.2 g of sodium acetate and contains 0.3 g of glacial acetic acid. You start dyeing at 60 ° C, gradually increasing the temperature to 98 ° C and colors in 1 hour to the end. It

909 609/382909 609/382

wird eine hervorragend '. gleichmäßige zitronengelbe Ausfärbung erzielt.will be an excellent '. Even lemon yellow color achieved.

"x , Beispiels " x , example

Polyacrylnitrilfasern werden im Flottenverhältnis Il 40. in ein Bad eingebracht, welches im Liter 0,125 g des kationischen FarbstoffesPolyacrylonitrile fibers are introduced into a bath in a liquor ratio of II 40, which contains 0.125 g per liter of the cationic dye

HXHX

GH.,GH.,

CH3 CH 3

sowie 0,5 g des Adduktes aus 30 Gewichtsteilen Dimethyl-cetyl-benzyl-ammonium-chlorid, 55 Gewichtsteilen Harnstoff und 15 Gewichtsteilen Monoacetylharnstoff nebst 0,25 g Natriumacetat und 0,3 g Eisessig enthält. Man beginnt mit dem Färben bei 50Q C, erhöht die · Temperatur allmählich auf 98° C und beläßt hierbei etwa V-U Stunden. Man erhält eine rotstichige Orangefärbung, die sich durch eine vollkommene Egalität auszeichnet.and 0.5 g of the adduct of 30 parts by weight of dimethyl-cetyl-benzyl-ammonium chloride, 55 parts by weight of urea and 15 parts by weight of monoacetylurea together with 0.25 g of sodium acetate and 0.3 g of glacial acetic acid. One begins with the dyeing at 50 Q C · the temperature gradually increased to 98 ° C and leaves this as VU hours. A reddish-tinged orange color is obtained, which is characterized by complete levelness.

B ei s ρ ie I 4For s ρ ie I 4

Ein Gewebe aus Polyacrylnitrilfasern wird im Flottenverhältnis 1 : 40 in ein 60° C warmes Bad eingebracht) welches im Liter 0,1 g des kationischen Farbstoffes des Beispiels 1 sowie 0,3 g des nachstehend näher erläuterten Adduktes 0,3 g Natriumacetat und 0,3 g Eisessig enthält. Man erhöht die Temperatur der Flotte allmählich von 60 auf 98° C und hält das Bad etwa 90 Minuten bei dieser Temperatur. Es wird eine Rosafärbung von vollkommener Gleichmäßigkeit erzielt.A fabric made of polyacrylonitrile fibers is im Liquor ratio 1:40 introduced into a 60 ° C bath) which per liter of 0.1 g of the cationic Dyestuff of Example 1 and 0.3 g of the adduct explained in more detail below, 0.3 g of sodium acetate and Contains 0.3 g of glacial acetic acid. The temperature of the liquor is gradually increased from 60 to 98 ° C. and the bath is kept about 90 minutes at this temperature. It becomes a pink color of perfect uniformity achieved.

Das benutzte Addukt war dadurch erhalten worden, daß 30 Gewichtsteile der quaternären Ammoniumverbindung, die durch Umsetzung von Dimethyl-Palmkernfettamin mit Benzylchlorid bereitet war, mit Gewichtsteilen Harnstoff und 15 Gewichtsteilen Monoacetylharnstoff verschmolzen wurden.The adduct used was obtained by adding 30 parts by weight of the quaternary ammonium compound, which was prepared by reacting dimethyl palm kernel fatty amine with benzyl chloride Parts by weight of urea and 15 parts by weight of monoacetylurea were fused.

Claims (2)

Patentansprüche:Patent claims: 1. Verfahren zum Färben von aus Acrylnitrilpolymerisaten, Vinylidencyanidpolymerisaten bzw.1. Process for dyeing acrylonitrile polymers, vinylidenecyanide polymers or so aus Mischpolymerisaten derselben mit anderen Vinylverbindungen hergestellten Gebilden mit kationischen Farbstoffen, dadurch gekennzeichnet, daß man das Färben in Gegenwart von quarternären Ammoniumverbindungen, die einen gegebenenfalls durch Halogen substituierten Benzylrest und einen mindestens 8 Kohlenstoffatome aufweisenden Alkylrest enthalten, durchführt.so from copolymers of the same with others Buildings made from vinyl compounds with cationic dyes, characterized in that that the dyeing in the presence of quaternary ammonium compounds, which may be halogen-substituted benzyl radical and one having at least 8 carbon atoms Contain alkyl radical, performs. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die quaternären Ammoniumverbindüngen in Form ihrer Umsetzungsprodukte mit Harnstoff bzw. Harnstoffderivaten verwendet werden.2. The method according to claim 1, characterized in that the quaternary ammonium compounds used in the form of their reaction products with urea or urea derivatives will. In Betracht gezogene Druckschriften:
Britische Patentschrift Nr. 751 865.
Considered publications:
British Patent No. 751 865.
DEF23761A 1957-08-14 1957-08-14 Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds Pending DE1064016B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF23761A DE1064016B (en) 1957-08-14 1957-08-14 Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF23761A DE1064016B (en) 1957-08-14 1957-08-14 Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds

Publications (1)

Publication Number Publication Date
DE1064016B true DE1064016B (en) 1959-08-27

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ID=7090982

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF23761A Pending DE1064016B (en) 1957-08-14 1957-08-14 Process for coloring structures made from acrylonitrile polymers, vinylidenecyanide polymers or from copolymers of the same with other vinyl compounds

Country Status (1)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB751865A (en) * 1953-12-09 1956-07-04 Courtaulds Ltd Improvements in and relating to the dyeing of polymeric products

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB751865A (en) * 1953-12-09 1956-07-04 Courtaulds Ltd Improvements in and relating to the dyeing of polymeric products

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