GB660196A - Manufacture of new monoazo-dyestuffs - Google Patents

Manufacture of new monoazo-dyestuffs

Info

Publication number
GB660196A
GB660196A GB23751/48A GB2375148A GB660196A GB 660196 A GB660196 A GB 660196A GB 23751/48 A GB23751/48 A GB 23751/48A GB 2375148 A GB2375148 A GB 2375148A GB 660196 A GB660196 A GB 660196A
Authority
GB
United Kingdom
Prior art keywords
methyl
acid
amino
sulphon
aminobenzene
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
GB23751/48A
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 GB660196A publication Critical patent/GB660196A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/24Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28Amino naphthols
    • C09B29/30Amino naphtholsulfonic acid

Landscapes

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

Abstract

Compounds of the general formula <FORM:0660196/IV (b)/1> (wherein R1 represents an aromatic nucleus of the benzene series and R2 an aliphatic hydrocarbon radical of 8-12 carbon atoms) are manufactured by condensing a compound RSO2X (wherein R represents an aromatic nucleus of the benzene series and X a halogen atom or a reactive residue) with an amine H2N-R2, introducing into the nucleus R (if not already present therein) a substituent convertible into -NH2, and then so converting this substituent. Thus the compound RSO2X may be a benzene sulphonic acid halide containing a nitro group, subsequently reduced (e.g. with iron and hydrochloric acid), or an acylamino group, subsequently hydrolysed, and the condensation may be effected in an anhydrous or aqueous medium, advantageously in the presence of an acid-binding agent (e.g. a tertiary base such as pyridine). The nucleus R in the starting material may contain further substituents (e.g. halogen atoms such as chlorine, or alkoxy groups such as ethoxy or especially methoxy), or additional substituents may be introduced after the condensation, or substituents already present may be replaced by others.ALSO:Monoazo dyestuffs are manufactured by coupling a diazo compound of an amine of the general formula <FORM:0660196/IV (c)/1> wherein R1 represents an aromatic nucleus of the benzene series, which may contain further substituents (e.g. halogen atoms or alkoxy groups) and R2 represents an aliphatic hydrocarbon radical of 8-12 carbon atoms, with a naphthalene coupling component containing a nuclear sulphonic acid group and a nuclear hydroxy group, and free from aliphatic radicals of more than 9 carbon atoms. Suitable components are on the one hand 3- or 4-amino-, 4-alkoxy-3-amino-, 3-alkoxy-4-amino-, 6-chloro-3-amino- and 4- or 6-methyl-3-amino-benzene-1-sulphonalkylamides (in which the alkyl group contains 8-12 carbon atoms, preferably in an unbranched chain), and on the other hand naphthol-mono- and especially -di-sulphonic acids coupling in o-position to the hydroxy group, and aminonaphtholsulphonic acids (including N-substituted derivatives thereof), preferably coupling in o-position to the amino group. The products are suitable for dyeing nitrogen-containing fibres, e.g. animal fibres such as leather, silk and especially wool, or artificial fibres of superpolyamides or superpolyurethanes. Examples describe the preparation of the following dyestuffs: (1) 4-methoxy-3 - aminobenzene - 1 - sulphon - n - dodecylamide-->2 - naphthol - 6 : 8 - disulphonic acid; (2) the same amine-->1-naphthol-3 : 6-disulphonic or -4-sulphonic acid; (3) the same amine, or the corresponding 4-methyl compound -->1 - p - toluenesulphonylamino - 8 - naphthol - 3 : 6 - disulphonic acid; (4) 3 - aminobenzene - 1 - sulphon - n - dodecylamide or its 4 - methyl derivative-->2 - naphthol - 6 : 8-disulphonic acid; (5) 3 - aminobenzene - 1 - sulphon - n - octylamide or n - decylamide--> 2 : 8 : 6 - aminonaphtholsulphonic acid. In a further example: (6) wool is dyed scarlet with the first product of (2) from a bath containing sodium sulphate and acetic acid. Lists of additional coupling components are given. The Specification as open to inspection under Sect. 91 comprises also the use of other coupling components containing a sulphonic acid group, e.g. naphthylamine-mono- and di-sulphonic acids coupling in o-position to the amino group, and 1-phenyl-3-methyl-5-pyrazolones containing sulphonic acid groups. Additional examples describe the preparation of the dyestuffs 4 - methoxy or 6 - methyl - 3 - aminobenzene - 1 - sulphon - n - dodecylamide-->1-(21-chloro-51-sulpho or 21 : 51-disulpho)-phenyl-3 - methyl - 5 - pyrazolone, 3 - aminobenzene-1 - sulphon - n - dodecylamide or its 6-methyl or 6-chloro derivatives-->1-(41-sulpho)-phenyl - 3 - methyl - 5 - pyrazolone, and 3-aminobenzene - 1 - sulphon - n - octylamide--> 2 - naphthylamine - 6 - sulphonic acid or 1-(21 - chloro - 51 - sulpho) - phenyl - 3 - methyl-5 - pyrazolone. This subject-matter does not appear in the Specification as accepted.
GB23751/48A 1947-09-24 1948-09-09 Manufacture of new monoazo-dyestuffs Expired GB660196A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH660196X 1947-09-24

Publications (1)

Publication Number Publication Date
GB660196A true GB660196A (en) 1951-10-31

Family

ID=4526833

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23751/48A Expired GB660196A (en) 1947-09-24 1948-09-09 Manufacture of new monoazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB660196A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5106960A (en) * 1980-03-28 1992-04-21 Ciba-Geigy Corporation Azo dyes and the production and use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5106960A (en) * 1980-03-28 1992-04-21 Ciba-Geigy Corporation Azo dyes and the production and use thereof

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