GB755450A - Improvements in or relating to polyazo dyestuffs - Google Patents

Improvements in or relating to polyazo dyestuffs

Info

Publication number
GB755450A
GB755450A GB8126/54A GB812654A GB755450A GB 755450 A GB755450 A GB 755450A GB 8126/54 A GB8126/54 A GB 8126/54A GB 812654 A GB812654 A GB 812654A GB 755450 A GB755450 A GB 755450A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
naphthol
azo
hydroxynaphthalene
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
GB8126/54A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB755450A publication Critical patent/GB755450A/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
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24Disazo or polyazo compounds
    • C09B45/28Disazo or polyazo compounds containing copper
    • 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
    • C09B35/362D is benzene

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:0755450/IV(c)/1> where <FORM:0755450/IV(c)/2> is the residue of a naphthol compound of formula:- <FORM:0755450/IV(c)/3> where n is 0, 1 and 2, y is H, OH or an amino group which may be alkylated, cycloalkylated, aralkylated, arylated or acylated, or the residue of a naphthol sulphonic acid of formula:- <FORM:0755450/IV(c)/4> where one Z is OH and the other an -N=N-pyrazolone or -N=N-aryl residue containing a metallizable group in an ortho position to -N=N-, or the residue of a metal complex compound of such a naphthol sulphonic acid, <FORM:0755450/IV(c)/5> is the residue of a middle component of the benzene or naphthalene series, m is 1, 2 or 3, x is H or an alkylated, cycloalkylated, aralkylated, arylated or acylated amino group, and wherein the -OH groups and "alkoxy" are in ortho position to the respective azo groups and -azois in the para position to the respective azo group. The invention also includes copper and nickel complexes of the above dyestuffs. The dyestuffs may be made by the alkaline coupling of a diazo compound of 1-aminobenzene-2carboxylic acid substituted in the 4 position with a group capable of conversion to an amino group with the desired naphthol sulphonic acid, converting the said 4-substituent into an amino group, diazotizing, advantageously by an indirect method, coupling, e.g. in an acetic or formic acid medium, with an appropriate ortho-alkoxy-aminomiddle component diazotizing and coupling, advantageously in a weakly alkaline medium and optionally in the presence of an organic base, with the necessary naphthol or naphthol sulphonic acid or metal complex thereof, and, if required, the polyazo dyestuff thus obtained is treated with a copper- or nickel-yielding agent. Alternatively a 4-aminobenzene-2-carboxylic acid substituted in the 1-position with a group convertible to an amino group may be coupled with the above middle and final components before conversion of the 1-substituent and the aminodisazo compound thus obtained is diazotized and coupled with an appropriate naphthol and the product metallized if desired, the conditions of diazotization and coupling being as in the previous method except that the final coupling is advantageously effected in a weakly alkaline medium, optinally in the presence of an organic base. When the middle component is a 1-amino-2-alkoxynaphthalene-6-sulphonic acid coupling is advantageously effected in an alkaline medium, 4-substituted 1-amino-benzene-2-carboxylic acids specified are 1-amino-4-nitro-, -acetylamino-, -oxalylamino-, -benzoylamino-, and carbo-methoxy- and ethoxyamino - benzene - 2 - carboxylic acids. Specified naphthol sulphonic acids containing the group (SO3H)m are 1-naphthol-3-, -4- and -5- mono-, -3, 6- and -3, 8- di- and 3, 5, 7- and -3, 6, 8- tri-sulphonic acids, 2-naphthol-4-, -6- and -8- mono-, -3, 6- and -6, 8- di- and -3, 6, 8- tri-sulphonic acids, 2-methyl-, -ethyl-, -propyl-, -cyclohexyl-, -benzyl-, -phenyl-, (31 or 41-carboxy-, or 41-methoxy-)-phenyl-, acetyl-, -propionyl-butyryl-, -benzoyl- and -carbo-methoxy- or -ethoxy - amino - 5(8) - hydroxy - naphthalene - 7(6) - sulphonic acid, 2-acetyl- or -benzoylamino -5- hydroxynaphthalene -1, 7-disulphonic acid, 1-acetyl- or benzoyl-amino-8-hydroxynaphthalene -4- mono- and -3, 6- disulphonic acids and 2-acetyl- or benzoyl-amino -6- hydroxynaphthalene -8- sulphonic acid. Specified middle components are 1 - amino - 2 - methoxy - or - ethoxy - benzene, -naphthalene, - naphthalene - 6 - sulphonic acid and - 5 - methyl - or - acetylamino - ben - zene and 1 - amino - 2, 5 - dimethoxy - or - diethoxy - benzene. Specified naphthols containing y or sulphonic acids containing z used in both preparations are those containing (SO3H)m (except trisulphonic acids) and 1 - and 2 - naphthol, 1 - amino - 8 -hydroxynaphthalene - 4 - sulphonic acid, 2 - amino - 5(8) - hydroxynaphthalene - 7 (6) - sulphonic acid, 2 - amino - 5 - hydroxynaphthalene - 1, 7 - disulphonic acid, 1 - (21 - carboxybenzene - 11 - azo and - 41 - nitro - 21 - carboxybenzene - 11 - azo) - 2, 5 - dihydroxynaphthalene - 7 - sulphonic acid, 1 - (21-carboxy - and -hydroxy - benzene - 11 - azo) - 2, 5 - hydroxynaphthalene - 7, 51 - disulphonic acid, 1 - (21 - hydroxybenzene - 11 - azo) - 2, 5 - dihydroxynaphthalene - 7, 41 - disulphonic acid, 1, 5 - dihydroxy - 2 - (21 - hydroxy - benzene and - naphthalene - 11 - azo) - naphthalene - 7, 41 - disulphonic acid, 1, 5 - dihydroxy - 2 - (21 - hydroxynaphthalene - 11 - az - naphthalene - 7, 61 - disulphonic acid, 1, 5 - dihydroxy - 2 (11 - hydroxynaphthalene - 21 - azo) - naphthalene - 7, 41 - di - and 7, 31, 61 - trisulphonic acid and 1, 5 - dihydroxy - 2 (11 - phenyl - 31 - methyl -51 - pyrazolone - 41 - azo) - naphthalene - 7, 411 - disulphonic acid. Naphthol compounds which may be obtained as metal complexes may be coupled in their metallized form with the diazotized amino - dis - or mono - azo compounds. Specified 4 - aminobenzene - 2 - carboxylic acids are 1 - nitro -, acetylamino - , oxalylamino - , - benzoylamino - and -carbomethoxy - or - ethoxyamino - 4 - aminobenzene - 2 - carboxylic acid. Metallization is effected in the usual way. The dyestuffs dye cotton and regenerated cellulose in blue grey shades. Examples and a Table are provided illustrating the use of certain of the above specified components in the preparation of dyestuffs, an additional end component used being 1 - (21 - carboxybenzene - 11 - azo) - 2, 5 - dihydroxynaphthalene - 7, 41 - disulphonic acid.
GB8126/54A 1953-03-20 1954-03-19 Improvements in or relating to polyazo dyestuffs Expired GB755450A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH755450X 1953-03-20

Publications (1)

Publication Number Publication Date
GB755450A true GB755450A (en) 1956-08-22

Family

ID=4534234

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8126/54A Expired GB755450A (en) 1953-03-20 1954-03-19 Improvements in or relating to polyazo dyestuffs

Country Status (1)

Country Link
GB (1) GB755450A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046222B (en) * 1956-12-21 1958-12-11 Bayer Ag Process for the preparation of metal-containing polyazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046222B (en) * 1956-12-21 1958-12-11 Bayer Ag Process for the preparation of metal-containing polyazo dyes

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