GB2033401A - Mass colouration of polyacrylonitrile using iodides of cationic dyes - Google Patents

Mass colouration of polyacrylonitrile using iodides of cationic dyes Download PDF

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Publication number
GB2033401A
GB2033401A GB7930575A GB7930575A GB2033401A GB 2033401 A GB2033401 A GB 2033401A GB 7930575 A GB7930575 A GB 7930575A GB 7930575 A GB7930575 A GB 7930575A GB 2033401 A GB2033401 A GB 2033401A
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United Kingdom
Prior art keywords
dyestuff
spinning
cationic
acrylonitrile
iodides
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Withdrawn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
GB7930575A
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.)
Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB7930575A priority Critical patent/GB2033401A/en
Publication of GB2033401A publication Critical patent/GB2033401A/en
Withdrawn legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/18—Monocomponent 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/207—Dyes with amino groups and with onium groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
    • C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
    • C09B23/164—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/08—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—Dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)

Abstract

Polymers and copolymers of acrylonitrile are coloured by incorporating iodides of cationic dyes in the polymer spinning solution. The iodide is dissolved in the same solvent used in the spinning process to give a 5 to 20% or more by weight solution of the dyestuff salt. Clear solutions are obtained which do not clog the spinning nozzles.

Description

SPECIFICATION Mass colouration of poylacrylonitrile using iodides of cationic dyes This invention relates to the mass colouration of polymers or copolymers of acrylonitrile in a preextrusion process where the dyestuff is incorporated in the spinning solution before the spinning process.
The colouration of polymers and copolymers of acryionitrile by incorporating the tetrafluoroborate salts of certain quaternised triazole azo dyestuffs in the spinning solution prior to spinning of the polymer or copolymerfibre has been proposed in British Patent No. 1514263.
We have now found that the iodide salts of a wide range of cationic dyestuffs can be incorporated in the spinning solutions used for the production of fibres of acrylonitrile polymers and copolymers to give coloured polymers of high tinctorial strength having high fastness.
Thus according to the present invention there is provided a process for the spin-dyeing of the polymers and copolymers of acrylonitrile which comprises incorporating into the spinning solution of the polymer or copolymer an iodide salt of a cationic dyestuff.
The process of the invention is applicable to the wide variety of polymers and copolymers of acrylonitrile. It may be applied for example to homopolymers of acrylonitrile and to copolymers thereof with other vinyl compounds for example vinyl chloride, vinyl acetate and acrylic and methacrylic esters and amides. Polymers and copolymers of acrylonitrile available as articles of commerce corltain acid groups which are essential for the attachment of basic dyestuff molecules to the polymer or copolymer.
It will be realised that the presence of acid groups in the polymers or copolymers of acrylonitrile is essential for the application of the present process.
There my be used in the present process any of the iodide salts of the many known classes of cationic dyestuffs or basic dyestuffs as thay are often called. Thus there may be used the iodide salts of cationic or basic dystuffs of the azo, anthraquinone, methine, styryl, naphtholactam, oxazine, thiazine, triphenylmethane, coomarin, quinophthalone and nitro series. The process is particularly useful with iodides of cationic monoazo dyestuffs of the carbocyclic and heterocyclic series for example azobenzene derivatives, azopyridones, diazahemicyanines and diazacarbocyanines and also with odides of hemicyanines, azacarbocyanines and triazacarbocyanines.
The foilowing classes of dyestuffs are given as more specific examples of cationic dyestuff types which may be used in the present process, the formula of specific dyestuffs in each class are given by way of exemplification.
Azobenzenes from para-eounling aminesZ for example
Azole,yridones, for example
Hemicyanines, for example
Diazahemieyanine, for example
Azacarbocyanines, for example
Diazacarbocyanines, for example
Anthraguizone, for example
Triphenylmethane. for example
Malachite Green Iodide Oxazine, for example
Thiamine, for example
r# Methylene Blue Iodide Triazacarbocyanine, for example
Naphthostyrols (Naphtholactams), for example
Coomarin, for example
lodide salts of cationic dyestuffs may be made by normal double decomposition reaction. For example the dyestuff of formula
may be dissolved in 5% aqueous acetic acid by warming to 400 C, the solution screened from trace insoluble matter by filtration with a filter aid and the filtrate treated with 20% aqueous sodium iodide to precipitate the dyestuff iodide salt which can be recovered by filtration.
The process of the invention may be carried out by dissolving the dyestuff iodide salt in the same solvent as is used in the spinning process for dissolution of iihe acrylonitrile polymer or copolymer, for example dimethyl formamide, dimethylacetamide or dimethylsulphoxide and then adding this solution of dyestuff iodide salt to the spinning solution. The mixture is then adequately mixed and the polymer or copolymer spun in the normal way, for example by a dry spinning process or by a wet spinning process.
The spun fibres may be given any of the after-treatments known in the art.
The solution of the dyestuff iodide salt is preferably a concentrated solution containing for example 5% to 20% by weight or more of the dyestuff salt. The dyestuff iodides possess high solubility in the solvents normally used in spinning processes.
We have found that by use of the iodide salts it is possible to obtain clear spinning solutions which do not clog the spinning nozzles. The dyed fibres produced by the process of the invention have high fastness to wet treatments and good light fastness.
The physical properties of the fibres were not impaired by the process of colouration.

Claims (7)

1. A process for the spin-dyeing of polymers and copolymers of acrylonitrile which comprises incorporating into the spinning solution of the polymer or copolymer an iodide salt of a cationic dyestuff.
2. A process as claimed in claim 1 in which the cationic dyestuff is a dyestuff of the azo, anthraquinone, methine, styryl, naphtholactam, oxazine, thiazine, triphenylmethane, coomarin, quinophthalone or nitro series.
3. A process as claimed in claim 1 which the cationic dyestuff is a monoazo dyestuff of the carbocyclic or heterocyclic series.
4. A process as claimed in claim 1 in which the cationic dyestuff is an azobenzene derivative or an azopyridone, a hemicyanine, a diazohemicyanine, or an azadiaza- or triazacarbocyanine.
5. A process as claimed in any one of the preceding claims in which the dyestuff iodide salt is dissolved in the same solvent as is used in the spinning process for dissolution of the acrylonitrile polymer or copolymer.
6. A process as claimed in claim 5 in which the dyestuff solution so obtained contains 5% to 20% by weight of the dystuff salt.
7. A process as claimed in claim 1 substantially as herein described.
GB7930575A 1978-10-10 1979-09-04 Mass colouration of polyacrylonitrile using iodides of cationic dyes Withdrawn GB2033401A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB7930575A GB2033401A (en) 1978-10-10 1979-09-04 Mass colouration of polyacrylonitrile using iodides of cationic dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7840022 1978-10-10
GB7930575A GB2033401A (en) 1978-10-10 1979-09-04 Mass colouration of polyacrylonitrile using iodides of cationic dyes

Publications (1)

Publication Number Publication Date
GB2033401A true GB2033401A (en) 1980-05-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB7930575A Withdrawn GB2033401A (en) 1978-10-10 1979-09-04 Mass colouration of polyacrylonitrile using iodides of cationic dyes

Country Status (1)

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GB (1) GB2033401A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055222A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Salts of cationic anthraquinone dyes, their preparation and their use
EP0055221A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Monocationic dyestuff salts
EP0055224A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Process for spun-dyeing polymers or copolymers of acrylonitrile
EP0055223A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Salts of basic oxazine dyes
EP0178832A2 (en) * 1984-10-16 1986-04-23 Imperial Chemical Industries Plc Thermal transfer printing
EP0373432A2 (en) * 1988-12-14 1990-06-20 Bayer Ag Malachite green-mixing salts

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055222A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Salts of cationic anthraquinone dyes, their preparation and their use
EP0055221A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Monocationic dyestuff salts
EP0055224A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Process for spun-dyeing polymers or copolymers of acrylonitrile
EP0055223A2 (en) * 1980-12-24 1982-06-30 Ciba-Geigy Ag Salts of basic oxazine dyes
EP0055222A3 (en) * 1980-12-24 1983-06-15 Ciba-Geigy Ag Salts of cationic anthraquinone dyes, their preparation and their use
EP0055221A3 (en) * 1980-12-24 1983-06-15 Ciba-Geigy Ag Monocationic dyestuff salts
EP0055223A3 (en) * 1980-12-24 1983-06-22 Ciba-Geigy Ag Salts of basic oxazine dyes
EP0055224A3 (en) * 1980-12-24 1983-06-22 Ciba-Geigy Ag Process for spun-dyeing polymers or copolymers of acrylonitrile
EP0178832A2 (en) * 1984-10-16 1986-04-23 Imperial Chemical Industries Plc Thermal transfer printing
US4664671A (en) * 1984-10-16 1987-05-12 Imperial Chemical Industries Plc Thermal transfer printing cationic dye with soft anionic base
EP0178832A3 (en) * 1984-10-16 1987-06-03 Imperial Chemical Industries Plc Thermal transfer printing
EP0373432A2 (en) * 1988-12-14 1990-06-20 Bayer Ag Malachite green-mixing salts
EP0373432A3 (en) * 1988-12-14 1991-11-13 Bayer Ag Malachite green-mixing salts

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