GB826405A - New monoazo dyestuffs containing dichlorotriazinylamino groups - Google Patents

New monoazo dyestuffs containing dichlorotriazinylamino groups

Info

Publication number
GB826405A
GB826405A GB3380955A GB3380955A GB826405A GB 826405 A GB826405 A GB 826405A GB 3380955 A GB3380955 A GB 3380955A GB 3380955 A GB3380955 A GB 3380955A GB 826405 A GB826405 A GB 826405A
Authority
GB
United Kingdom
Prior art keywords
methyl
pyrazolone
sulphophenyl
group
groups
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
GB3380955A
Inventor
William Elliott Stephen
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 GB3380955A priority Critical patent/GB826405A/en
Priority to ES0232091A priority patent/ES232091A1/en
Publication of GB826405A publication Critical patent/GB826405A/en
Priority to MY6000044A priority patent/MY6000044A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C09B62/02Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08Azo dyes
    • C09B62/085Monoazo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention comprises monoazo dyes of formula <FORM:0826405/IV(c)/1> wherein the benzene nucleus X may be substituted but is free from hydroxy groups in all positions and from carboxyl groups ortho to the azo group, the benzene nucleus Z may be substituted other than by hydroxyl groups, Y is a methyl, carboalkoxy or carboxyl group, the dichloro-s-triazinylamino group is attached to X in meta- or para-position to the azo group or to Z in meta- or para-position to the nitrogen atom of the pyrazolone ring and the molecule contains at least two carboxyl and/or sulphonic acid groups. The dyes are prepared by reacting at least one molecular proportion of cyanuric chloride with a monoaminoazo compound of formula <FORM:0826405/IV(c)/2> wherein the amino group is attached to the nuclei X and Z in the way defined for the dichloro-s-triazinylamino group above and Y and the substituents in X and Z and the final product are as defined above. Alternatively the dyes are prepared by coupling a diazonium compound of the benzene series with a 1-phenyl-3 - methyl -, carboalkoxy - or carboxy - 5-pyrazolone wherein either the diazonium compound or the pyrazolone contains in the benzene ring, in meta- or para-position to the attached nitrogen atom, a 4 : 6 - dichloro - s - triazin - 2-ylamino group and the diazonium and pyrazolone components are so chosen that the final product is substituted as defined above. The aminoazo compounds of formula II wherein the amino group is in the nucleus X are prepared by diazotizing a suitable monoamine of the benzene series containing a nitro or acylamino group meta or para to the amino group, coupling with a 1-phenyl-3-methyl, carboalkoxy- or carboxy-5-pyrazolone free from hydroxyl, amino, nitro or acylamino groups and reducing the nitro group or hydrolysing the acylamino group of the resultant monoazo dye, the final product having at least two carboxyl and/or sulphonic acid groups. Specified components are: m- or p-nitroaniline, 3-nitroaniline - 6 - sulphonic acid, m - or p - aminoacetanilide, 4 - or 3 - aminoacetanilide - 3 or 4 - sulphonic acid and 4 - amino - 2 - acettoluidide - 5 - sulphonic acid; 1 - (61 - chloro - 31-methyl - 41 - sulphophenyl) - or - (41 - chloro-21 - sulphophenyl) - or - (21 - chloro - 41-methyl - 51 - sulphophenyl) - or (41 - methyl-21 - sulphophenyl) - or - (21:51 - or 31 : 51 - disulphophenyl) - or - (41 - ethoxy - 21 - sulphophenyl) - or - (21:41 - dichloro - 51 - sulphophenyl) - or - (61 - chloro - 31 - sulpho - 21-methylphenyl) - or (31 - or 41 - carboxyphenyl)-3 - methyl - 5 - pyrazolone, 1 - (61 - chloro - 41-sulpho - 21 - methylphenyl) - 3 - carboethoxy-5 - pyrazolone and 1 - (41 - sulphophenyl) - or - phenyl - or - p - tolyl - 3 - carboxy - 5-pyrazolone. The aminoazo compounds of formula II wherein the amino group is in the nucleus are prepared by coupling a suitable amine of the benzene series with a 1-(31- or 41 aminophenyl) - 3 - methyl, carboalkoxy - or carboxy - 5- pyrazolone, the final product having at least two carboxyl and/or sulphonic acid groups. Specified components are: orthanilic and sulphanilic acids, 4-methyl-2-sulphoaniline, 4- or 5-chloro-, 5- or 4-methyl-2-sulphoaniline, 5 - methoxy - 2 - sulphoaniline, and 2 : 5 - dichloro - 4 - sulphoaniline ; 1 - (31 - or 41-aminophenyl) - 3 - methyl -, carboxy - and carboethoxy - 5 - pyrazolones and 1 - (41-amino - 31 - carboxyphenyl) - 3 - methyl - 5-pyrazolone. The components used in the coupling method for the preparation of the compounds of formula I are prepared by reacting at least one molecular proportion of cyanuric chloride with a 1-(31- or 41-aminophenyl)-3-methyl, carboalkoxy- or carboxy-5-pyrazolone such as those specified above or a phenylene diamine such as 2-sulpho-1 : 4-phenylenediamine, 6 - sulpho - 1 : 3 - phenylenediamine and 2 : 4-diaminotoluene-5-sulphonic acid. The reaction of cyanuric chloride with amino compounds is preferably carried out in aqueous medium at between 0 DEG and 5 DEG C. and in the presence of an acid-binding agent such as sodium carbonate. The dyes are preferably isolated at a pH of 6-8 and dried at 20 DEG to 45 DEG C. in the presence of buffering agents such as mixtures of disodium hydrogen phosphate and sodium dihydrogen phosphate or of disodium hydrogen phosphate and potassium dihydrogen phosphate. The dyes may be used to colour silk, wool, regenerated protein, polyamide, polyacrylonitrile, cotton, linen and rayon in yellow to orange shades. In examples, cyanuric chloride is reacted with aminoazo compounds obtained from the following components with reduction of nitro groups or hydrolysis of acylamino groups where necessary, to give dyestuffs of formula I : diazo components: aniline - 2 : 5 - disulphonic acid, 4 - nitroaniline - 2 - sulphonic acid and 5-acetylamino - aniline - 2 - sulphonic acid; coupling components: 1 - (3 - aminophenyl)-or - (21 - methyl - 51 - sulphophenyl) - or - (21-or 41 - sulphophenyl) - or - (21:51 - dichloro-4 - sulphophenyl) - or - (61 - chloro - 41 - sulpho-21 - methylphenyl) - or - (21 - chloro - 51 - sulphenyl) - 3 - methyl - 5 - pyrazolone and 1 - (41-sulphophenyl) - 3 - carboxy - 5 - pyrazolone. Specifications 209,723, [Class 2 (iv)], 486,660, 515,066, [both in Group IV], and 797,946 are referred to.
GB3380955A 1955-11-25 1955-11-25 New monoazo dyestuffs containing dichlorotriazinylamino groups Expired GB826405A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB3380955A GB826405A (en) 1955-11-25 1955-11-25 New monoazo dyestuffs containing dichlorotriazinylamino groups
ES0232091A ES232091A1 (en) 1955-11-25 1956-11-24 New monoazo dyestuffs containing dichlorotriazinylamino groups
MY6000044A MY6000044A (en) 1955-11-25 1960-12-31 New monoazo dyestuffs containing dichlorltriazinylamino groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3380955A GB826405A (en) 1955-11-25 1955-11-25 New monoazo dyestuffs containing dichlorotriazinylamino groups

Publications (1)

Publication Number Publication Date
GB826405A true GB826405A (en) 1960-01-06

Family

ID=10357722

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3380955A Expired GB826405A (en) 1955-11-25 1955-11-25 New monoazo dyestuffs containing dichlorotriazinylamino groups

Country Status (3)

Country Link
ES (1) ES232091A1 (en)
GB (1) GB826405A (en)
MY (1) MY6000044A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125403A (en) * 1964-03-17 New colouration process
US4038267A (en) * 1973-05-24 1977-07-26 Sumitomo Chemical Company, Limited Triazine reactive dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125403A (en) * 1964-03-17 New colouration process
US4038267A (en) * 1973-05-24 1977-07-26 Sumitomo Chemical Company, Limited Triazine reactive dyes

Also Published As

Publication number Publication date
ES232091A1 (en) 1957-05-16
MY6000044A (en) 1960-12-31

Similar Documents

Publication Publication Date Title
GB1576237A (en) Dyestuffs containing the triazine ring their preparation and use
US3758470A (en) Triazinyl anthraquinones
US2945021A (en) Monoazo and disazo triazine dyes
US2929809A (en) New complex metal compounds of monoazo-dyestuffs
US3518245A (en) Azo dyestuffs and their metal complex compounds
US5789557A (en) Reactive azo dyes with a coupler of the aminonaphthalene series
US2945022A (en) Monoazo and disazo triazine dyes
US3226176A (en) Cellulose, wool, silk and leather fibers fast-dyed with chlorotriazine containing reactive dyestuffs
GB885815A (en) New water-soluble dyestuffs containing halogen acylamino groups and their manufacture and use
US3426008A (en) Water-soluble monoazo dyestuffs and their metal complex compounds
US3859271A (en) Reactive yellow &#39; -sulfatoethylsulfonyl phenylazo-4-(1-substituted phenyl-3-methyl-5-amino)-pyrazole dyes
US2860128A (en) Triazine disazo-dyestuffs
US3950128A (en) Disazo dyestuffs
US4314818A (en) 1-Amino-7-[3&#39;-(5&#34;-chloro-2&#34;,4&#34;-difluoropyrimidyl-6&#34;-amino)-6&#39;-sulfophenylazo]-8-hydroxy-2-sulfamoyl or substituted sulfamoyl-phenylazo naphthalene-3,6-disulfonic acids
US3697500A (en) Water-soluble disazo pyrazole dyestuffs containing fiber-reactive substituents
GB826405A (en) New monoazo dyestuffs containing dichlorotriazinylamino groups
US3163635A (en) Water-soluble azo dyestuffs
US3133909A (en) Monoazo dyestuffs
US3197456A (en) Azo-dyestuffs
US3349074A (en) Water-soluble azo dyestuffs
US3126370A (en) Oh nhc
US4297278A (en) Pentakis-and heptakis-azoxy dyestuffs
US2910464A (en) Triazine monoazo-dyestuffs
US2741655A (en) Cupriferous azo-dyestuffs
EP0592105B1 (en) Reactive dyes