[go: up one dir, main page]

GB1039379A - Reactive dyestuffs containing a quinoxaline nucleus - Google Patents

Reactive dyestuffs containing a quinoxaline nucleus

Info

Publication number
GB1039379A
GB1039379A GB37354/63A GB3735463A GB1039379A GB 1039379 A GB1039379 A GB 1039379A GB 37354/63 A GB37354/63 A GB 37354/63A GB 3735463 A GB3735463 A GB 3735463A GB 1039379 A GB1039379 A GB 1039379A
Authority
GB
United Kingdom
Prior art keywords
group
dyestuffs
formula
groups
radical
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.)
Expired
Application number
GB37354/63A
Inventor
Gerald Booth
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
Original Assignee
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 GB37354/63A priority Critical patent/GB1039379A/en
Publication of GB1039379A publication Critical patent/GB1039379A/en
Expired legal-status Critical Current

Links

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
    • D06P1/38General 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507Azo dyes
    • C09B62/513Disazo or polyazo 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
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention comprises dyestuffs containing attached to a carbon atom present in the dyestuffs at least one group of the formula <FORM:1039379/C4-C5/1> wherein R represents hydrogen or C1 to C4 alkyl; X represents Cl or Br or -SO3M wherein M represents Na or K; and the benzene ring A may contain further substituents. Each of the groups of the above formula is attached to a carbon atom present in the dyestuffs. The said carbon atom may form part of an aryl residue present in the dyestuffs or may form part of an alkyl chain which is directly attached to an aryl residue present in the dyestuffs or is attached to an aryl residue through a bridging atom or group. The dyestuffs may be dyestuffs of the azo, nitro, anthraquinone or phthalocyanine series; and may contain co-ordinately bound metal atoms. They also preferably contain at least one water-solubilizing group. The dyestuffs containing groups of the above formula, wherein X represents Cl or Br may be obtained by reacting a dyestuff compound which contains at least one -NHR group with a compound of the formula <FORM:1039379/C4-C5/2> wherein X1 represents Cl or Br (see Division C2 for preparation) at least one molecular proportion of the said compound being used for each -NHR group present in the dyestuff compound. The dyestuffs containing groups of the above general formula wherein X represents -SO3M may be obtained by reacting a dyestuff wherein X represents Cl or Br with a Na or K salt of sulphurous acid. Specified examples of dyestuffs containing at least one -NHR group are as follows: (1) Monoazo compounds of the formula <FORM:1039379/C4-C5/3> wherein D1 represents a mono- or di-cyclic aryl radical which is free from azo groups and NHR groups. (2) Disazo compounds of Formula III, wherein D1 represents a radical of the azobenzene, azonaphthalene or phenylazonaphthalene series and the naphthalene nucleus is substituted by the NHR group. (3) Monoazo compounds of the formula <FORM:1039379/C4-C5/4> wherein D1 represents a mono or dicyclic aryl radical as defined in class (1) and the benzene nucleus may contain halogen atoms, alkyl, alkoxy, carboxylic acid or acylamino groups. (4) Mono- or dis-azo compounds of the formula <FORM:1039379/C4-C5/5> wherein D1 represents a radical as defined for class (2) or a mono- or dicyclicarylene radical of the benzene or naphthalene series and K represents the radical of a naphthol sulphonic acid or the radical of an enolized or enolizable ketomethylene compound having the OH group oto the azo group. (5) Mono- or dis-azo compounds of the formula D1-N = N-K2-NHR wherein D1 is as defined in classes (1) and (2), K2 represents the radical of an enolizable ketomethylene compound having the -OH group oto the azo group. (6) The metal complex compounds of dyes of Formulae III, V and VI which contain a metallizable group ortho to the azo group in D1. (7) Anthraquinone compounds of the formula <FORM:1039379/C4-C5/6> wherein the anthraquinone nucleus may contain an additional SO3H group in the 5-, 6-, 7- or 8-position and Y represents a bridging group which is preferably a divalent radical of the benzene series. (8) Phthalocyanine compounds of the formula <FORM:1039379/C4-C5/7> wherein Pc represents the phthalocyanine nucleus preferably of copper phthalocyanine, o represents -OH and/or NH2 or substituted amino, Y1 represents a bridging group preferably an aliphatic, cycloaliphatic or aromatic bridging group, n and m each represent a value of from 1 to 3 and may be the same or different provided that n+m is not greater than 4. (9) Nitro dyestuffs of the formula O2N-B1-NH-B2-NHR wherein B1 and B2 represent monocyclic aryl nuclei, the nitro group in B1 being ortho to the NH group. The dyestuffs can also be obtained by reacting dyestuff intermediates containing reactive halogen atoms, such as 1-amino-4-bromo - anthraquinone - 2 - sulphonic acid or phthalocyanine sulphonylchlorides can be reacted with amines containing a group of Formula I, such as an amine of the formula <FORM:1039379/C4-C5/8> wherein the benzene ring A1 can be substituted by halogen, methyl, methoxy or sulphonic acid groups. The dyestuffs can also be obtained by diazotizing a primary aromatic amine and coupling the resulting diazo compound with a coupling component, the primary aromatic amine and the coupling component together containing at least one group of Formula I. A preferred class of the dyestuffs are those of the formula <FORM:1039379/C4-C5/9> wherein p represents 1 or 2, and D5 represents a dyestuff radical of the azo, anthraquinone or phthalocyanine series which contains at least one -SO3H or -COOH group. The dyestuffs may be applied to natural and artificial textile materials, for example, cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile, modified polyacrylonitrile and aromatic polyester fibres, by dyeing, padding or printing processes, whereby the textile materials are coloured in bright shades (see Division D1 for dyeing processes).ALSO:Compounds of the formula <FORM:1039379/C2/1> II wherein X1 represents Cl or Br and the benzene ring A may contain further substituents such as chlorine, alkyl, alkoxy and nitro groups, are obtained by treating the corresponding compound wherein X1 represents an -OH group with a chlorinating or brominating agent, for example POCl3, POBr3, PCl5 or PBr5. Compounds of the formula <FORM:1039379/C2/2> VII wherein R is H or C1-C4 alkyl and X is Cl, Br or SO3M, and the benzene ring A1 may be substituted by halogen, methyl, methoxy or sulphonic groups, are obtained by reacting the corresponding amino- or nitro-benzene containing a -NHR group with a compound of Formula II, and subsequently reducing the nitro group to an amino group.ALSO:Dyestuffs containing at least one group of the formula <FORM:1039379/D1-D2/1> wherein R represents hydrogen or C1 to C4 alkyl; X represents Cl or Br or -SO3M wherein M represents Na or K; and the benzene ring A may contain further substituents (see Division C4 for preparation), are applied to natural and artificial textile materials for example, cotton, viscose rayon regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile, modified polyacrylonitrile and aromatic polyester fibres by dyeing, padding or printing processes. Dyestuffs containing water-solubilizing groups may be applied to cellulose textiles in conjunction with an acid-binding agent. The aqueous solution of one or more of the said dyestuffs may also contain substances which are known to assist the application of dyestuffs to textile materials. The cellulose textile materials can be printed with a printing paste containing one or more of the said dyestuffs. This may be brought about by pretreating the cellulose textile material with acid-binding agent, by incorporating an acid-binding agent in the printing paste, by applying the printing paste and subsequently immersing the textile material in a hot aqueous solution or suspension of the acid-binding agent or the printed textile material impregnated with an aqueous solution or suspension of the acid binding agent. At the conclusion of the dyeing and/or printing process the so-coloured cellulose textiles may be subjected to a "soaping" treatment. Dyestuffs not containing water-solubilizing groups are applied to textiles in the form of an aqueous dispersion which may be obtained by gravel-milling the dyestuff with water in the presence of a dispersing agent. The dyestuffs may be applied to nitrogen-containing textiles such as wool and polyamide textiles, from a mildly alkaline, neutral or acid dyebath.
GB37354/63A 1963-09-23 1963-09-23 Reactive dyestuffs containing a quinoxaline nucleus Expired GB1039379A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB37354/63A GB1039379A (en) 1963-09-23 1963-09-23 Reactive dyestuffs containing a quinoxaline nucleus

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB37354/63A GB1039379A (en) 1963-09-23 1963-09-23 Reactive dyestuffs containing a quinoxaline nucleus

Publications (1)

Publication Number Publication Date
GB1039379A true GB1039379A (en) 1966-08-17

Family

ID=10395824

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37354/63A Expired GB1039379A (en) 1963-09-23 1963-09-23 Reactive dyestuffs containing a quinoxaline nucleus

Country Status (1)

Country Link
GB (1) GB1039379A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7182806B2 (en) 2003-07-18 2007-02-27 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
US7189283B2 (en) 2003-07-18 2007-03-13 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
US7326287B2 (en) 2003-07-18 2008-02-05 Fujifilm Imaging Colorants Limited Cyan inks and their use in ink-jet printers
US7678899B2 (en) 2003-07-18 2010-03-16 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
WO2020059483A1 (en) * 2018-09-18 2020-03-26 富士フイルム株式会社 Composition, film, optical filter, solid-state imaging device, infrared sensor, method for manufacturing optical filter, camera module, compound, and dispersion composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7182806B2 (en) 2003-07-18 2007-02-27 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
US7189283B2 (en) 2003-07-18 2007-03-13 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
US7326287B2 (en) 2003-07-18 2008-02-05 Fujifilm Imaging Colorants Limited Cyan inks and their use in ink-jet printers
US7678899B2 (en) 2003-07-18 2010-03-16 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
WO2020059483A1 (en) * 2018-09-18 2020-03-26 富士フイルム株式会社 Composition, film, optical filter, solid-state imaging device, infrared sensor, method for manufacturing optical filter, camera module, compound, and dispersion composition
JPWO2020059483A1 (en) * 2018-09-18 2021-08-30 富士フイルム株式会社 Compositions, membranes, optical filters, solid-state image sensors, infrared sensors, methods for manufacturing optical filters, camera modules, compounds, and dispersion compositions.

Similar Documents

Publication Publication Date Title
US2892674A (en) Treatment of cellulosic materials
US3007762A (en) Process for dyeing polyhydroxylated materials
US3127389A (en) Hojs-i
GB1039379A (en) Reactive dyestuffs containing a quinoxaline nucleus
GB901434A (en) Azo dyestuffs
US2192127A (en) Process of producing fast dyeings
US3157630A (en) Copper-containing monoazo dyestuffs having a cyanuric halide radical
DE1089095B (en) Process for the production of dyes
US2940812A (en) New textile treatment process
US2475228A (en) Dinitro monoazo compound
US3125562A (en) Disazo dyestuffs
US2345010A (en) Azo dye
US3123595A (en) Cihzc-cichxhzcxen-o c
GB1498669A (en) Azo dyestuffs
US3498967A (en) Fiber reactive azo-dyestuffs
US3117962A (en) Azo dyes containing a halomethylbenzoylamino radical
US3458496A (en) Reactive monoazo dyes containing 2,4-dihalopyrimidine groups
US3051542A (en) Process for dyeing or printing poly-
US3939141A (en) Water-soluble copper complex phenyl azo naphthalene reactive dyestuffs
GB952619A (en) New pyrimidine dyestuffs
US3577405A (en) Water-soluble,yellow mono-azo dyes with active methylene coupler
GB885814A (en) Water-soluble dyestuffs containing unsaturated carboxylic acid residues
US2213193A (en) Process of producing fast dyeings
US3040023A (en) Monoazo-dyestuffs
US3154533A (en) New azo dyestuffs