GB757047A - New metalliferous trisazo-dyestuffs and process for making them - Google Patents

New metalliferous trisazo-dyestuffs and process for making them

Info

Publication number
GB757047A
GB757047A GB5505/54A GB550554A GB757047A GB 757047 A GB757047 A GB 757047A GB 5505/54 A GB5505/54 A GB 5505/54A GB 550554 A GB550554 A GB 550554A GB 757047 A GB757047 A GB 757047A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
amino
methyl
naphthol
phenyl
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
GB5505/54A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB757047A publication Critical patent/GB757047A/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
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/36Trisazo dyes of the type

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises dyestuffs of formula <FORM:0757047/IV(c)/1> where Me is a nickel or copper atom bound in complex union, Y is -CH=CH or a direct bond, Py is a pyrazolone residue, R1 and R2 are benzene residues, R3 is a benzene or napthalene residue bound in para-position to the azo-linkages, R4 is a naphthalene residue, the azo linkages bound to R1 and R2 are in para-position to Y and the -O-Me-O- group is connected to R3 and R4 in positions vicinal to the azo linkage. They are made by metallizing in conventional fashion the corresponding o-alkoxy, o1-hydroxycompound, R4 containing the hydroxy group. Theoalkoxy, o1-hydroxy compound may be made by coupling a tetrazo compound of a diamine of formula H2N-R1-Y-R2-NH2 with a pyrazolone, advantageously in a weakly acid medium, and with an appropriate amine as middle component in a weakly acid to weakly alkaline medium diazotizing the amino diazo dyestuffs thus obtained and coupling with the necessary naphthalene derivative. Alternatively the diamine may be diazotized and coupled with the pyrazolone, the resulting dyestuff diazotized and coupled with the middle component and the preparation completed as above. They may also be made by diazotizing a compound of formula A-R2-Y-R2-A where one A is NH2 and the other a group convertible to NH2 and the other a group convertible to NH2, coupling with a pyrazolone, converting the remaining A to NH2, diazotizing the monazo dyestuff thus obtained and coupling with an appropriate middle component and then proceeding as in the previous preparations. Alternatively in the preparation of the previous sentence initial coupling may be effected with the middle component and the dyestuff thus obtained diazotized and coupled with the end component before the remaining A is converted to NH2 and the coupling with the pyrazolone effected. Coupling with the end component is preferably effected in an alkaline medium in the presence of pyridine or picoline. The diamines used may contain further substituents such as chlorine, methyl, ethoxy, methoxy and sulphonic acid groups, those specified being 4, 41- diaminodiphenyl and its -3-mono- and -2, 21- and -3, 31- disulphonic acids and 3, 31- dichloro- and -dimethyl- 4, 41-diamino-diphenyl. Specified compounds of formula A-R1-Y-R2-A which may contain the substituents similar to those of the diamines are 4-amino-41-acetylaminodiphenyl and its -3-sulphonic acid and 4-nitro-41-aminostilbene-2, 21-disulphonic acid. Specified pyrazolones are 3-methyl-5-pyrazolone, 1-alkyl-3-methyl-5-pyrazolone and especially 1-phenyl-3-methyl-5-pyrazolone and its 41-methyl- and -chloro-phenyl derivative and particularly 1-phenyl-5-pyrazolone-3-carboxylic acid, 1-phenyl-3-methyl-5-pyrazolone-31- and -41-sulphonic acid, 1-(41-methylphenyl)-3-methyl-5-pyrazolone-31-sulphonic acid, 1-(21-chlorophenyl)-3-methyl-5-pyrazolone-41 -sulphonic acid, 1-phenyl-3-methyl-5-pyrazolone-41-carboxylic acid, 1-phenyl-5-pyrazolone-3-carboxylic acid-31sulphonic acid and 1-phenyl-3-methyl-5-pyrazolone-31-sulphonic acid amide. Specified middle components are 1-amino-2-methoxybenzene, 1-amino-2-methoxy-5-methyl- and -ethoxy-benzene, 1-amino-2, 5-dimethoxy-and -diethoxy-benzene, 1-amino-2-ethoxy-5 1-methoxy-benzene, 1-amino-2-methoxy and-ethoxy-naphthalene and then -6- and -7-sulphonic acids. Specified end components are 2-naphthol and its 6-mono- and 3, 6-disulphonic acids, 1-naphthol-4-mono-and -3, 6- and -3, 8-disulphonic acids, 1, 8-dioxynaphthalene- 3, 6-disulphonic acid, 1-amino-5-naphthol-7- and 1-amino -8-naphthol-4-sulphonic acids, 2-amino-8-naphthol-6- and 2-amino-6-napthol-8-sulphonic acids, 2-amino-5-naphthol-7-sulphonic acid, 2-acetyl, -benzoyl-, -(41chlorobenzoyl-), -phenyl-, -(21- and 41-methoxyphenyl)-, -(31- and 41-carboxy-methoxyphenyl) -amino-5-naphthol-7-sulphonic acids, and 2 -(41-methyl- and -chloro-phenyl) and -phenyl-amino-5-naphthol-7, 31-disulphonic acids. Preferred dyestuffs are those where O-R3 is of formula <FORM:0757047/IV(c)/2> where the SO3H group is in a b -position of ring I and in which the naphthalene residue R4 contains an arylamino or acylamino group and one or two sulphonic acid groups as substituents. Dyestuffs in which R3 is a naphthalene residue, e.g. those in which R3 corresponds to a 2-methoxy-6 -sulpho-naphthalene residue, are preferably coppered with copper sulphite and an alkali acetate, and those in which R3 is an alkoxy-benzene residue, e.g. 1-methyl-4-methoxy-, 1, 4-dimethoxy- and 1-methoxy-4 diethoxy benzene are preferably treated with copper tetramine sulphates. The dyestuffs dye wool, silk and especially cellulose containing fibres, e.g. cotton, linen, artificial silk and regenerated cellulose in grey to olive green tints. Examples and a table are provided illustrating the preparation of the dyestuffs from certain of the above components and their use in dyeing cotton, additional components used to those previously mentioned are 1-phenyl-5-pyrazolone-3-carboxylic and -41-suphonic acid, 4-amino-41-oxalylamino-diphenyl, 1-benzoyl- and -acetylamino-8-naphthol-4-sulphonic acids, 2-benzoylamino-6-naphthol-8-sulphonic acid and 2-phenylamino-5-naphthol-7-sulphonic acid-31-carboxylic acid. Specifications 644,883 and 738,309 are referred to.
GB5505/54A 1953-02-26 1954-02-24 New metalliferous trisazo-dyestuffs and process for making them Expired GB757047A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH757047X 1953-02-26

Publications (1)

Publication Number Publication Date
GB757047A true GB757047A (en) 1956-09-12

Family

ID=4534363

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5505/54A Expired GB757047A (en) 1953-02-26 1954-02-24 New metalliferous trisazo-dyestuffs and process for making them

Country Status (1)

Country Link
GB (1) GB757047A (en)

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