GB498051A - Manufacture of dyestuffs - Google Patents

Manufacture of dyestuffs

Info

Publication number
GB498051A
GB498051A GB19520/37A GB1952037A GB498051A GB 498051 A GB498051 A GB 498051A GB 19520/37 A GB19520/37 A GB 19520/37A GB 1952037 A GB1952037 A GB 1952037A GB 498051 A GB498051 A GB 498051A
Authority
GB
United Kingdom
Prior art keywords
amino
pseudo
azimidobenzene
nitro
methoxy
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
GB19520/37A
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
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB498051A publication Critical patent/GB498051A/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
    • C09B29/32Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group

Landscapes

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

Abstract

Azo dyes; azo dyes, forming upon the material; regenerated celluloses, dyeing; printing; pseudo-azimidobenzene derivatives.-Azo dyestuffs are manufactured by coupling, in substance or on the fibre, a diazo compound containing no hydroxy, sulphonic acid or carboxylic acid group with an arylide of acetoacetic acid of the general formula <FORM:0498051/IV/1> where R is a residue of the benzene series, (obtainable by condensing the corresponding amines with ethyl acetoacetate). The production of the dyes on the fibre may be applied to the colouring of vegetable fibres, regenerated celluloses, silk or wool, e.g. by padding the fibre in alkaline solution with the arylides and developing with a diazo compound, or by using preparations or printing colours containing an alkali salt of one of the arylides and a stabilized diazo compound in the form of a nitrosamine or a diazoamino compound, and developing, e.g. by passage through an acid, or by printing with mixtures of the free diazo components or the corresponding N-nitramines and alkali salts of the arylides and treating with nitrous acid, followed, if desired, by alkali. The dyes produced in substance are useful as pigments or for colouring lacquers or varnishes. In examples: (1) o-nitraniline is diazotized and coupled with the product obtained by heating 5-amino-2-phenyl-pseudo-azimidobenzene with ethyl acetoacetate in chlorobenzene in the presence of dimethylaniline; (2) cotton is impregnated with the coupling component of (1), and a greenish-yellow dyeing is developed with diazotized 1-amino-2-methyl-4-nitrobenzene, 1 - amino - 2 - methyl - 4 - chlorobenzene, 1-amino-2-nitro-4-chlorobenzene or 1-amino-2-nitro-4-methylbenzene, or redder shades with diazotized 1-amino-2-nitro-4-methoxybenzene or o-aminoazotoluene. Other diazo components specified are: aniline, ethers or esters of aminophenols, e.g. o- or p-anisidine or 4-chlor-2-aminodiphenyl ether, monoacylated products from 2 : 5-diaminohydroquinone diethyl or dimethyl ether and benzoyl or phenoxyacetyl chloride, aminoazo compounds, e.g. 4-amino-5-methoxy- or -2 : 5-dimethoxyazobenzene, chlorotoluidines, e.g. 4-chloro-1-methyl-2-aminobenzene, nitranilines, e.g. 4-nitro-2-methoxy-1-aminobenzene, o- or m-chloraniline or a - or b -naphthylamine. Samples have been furnished under Sect. 2 (5) of cotton yarn dyed by the formation thereon of the following dyestuffs: (I) o-nitraniline --> the condensation product from ethyl acetoacetate and 5 - amino - 2 - (41 - methoxy) - phenyl-pseudo-azimidobenzene (obtainable by oxidizing the azo dyestuff p-anisidine --> m-phenylenediamine); (II) 1-amino-2-nitro-4-methylbenzene --> the same coupling component; (III) 1-amino-2-nitro-4-methoxybenzene --> the same coupling component; (IV) o-nitraniline --> the condensation product from ethyl acetoacetate and 5-amino-2-(41-ethoxy)-phenyl-pseudo-azimidobenzene (obtainable by oxidizing the azo dyestuff p-phenetidine --> m-phenylenediamine); (V) p-nitraniline --> the same coupling component; (VI) 1 - amino - 2 - nitro - 4 - methoxybenzene --> the same coupling component; (VII) o-aminoazotoluene --> the condensation product from 5-amino-6-methyl-2-phenyl-pseudo-azimidobenzene; (VIII) 1-amino-2-nitro-4-chlorobenzene --> the condensation product from ethyl acetoacetate and 5-amino-6-methyl-2-(41-methoxy)-phenyl-pseudo-azimidobenzene (obtainable by oxidizing the azo dyestuff p-anisidine --> 2 : 4-diaminotoluene); (IX) 2 : 5-dichloraniline --> the condensation product from ethyl acetoacetate and 5-amino-6-methoxy-2-(41-methoxy) -phenyl-pseudo-azimidobenzene (obtainable by oxidizing the azo dyestuff p-anisidine --> 1 : 3-diamino-6-methoxybenzene; (X) 4 : 41-dichloro-2-aminodiphenyl ether --> the condensation product from ethyl acetoacetate and 5-amino-6-methoxy - 2 - (41 - methoxy) - phenyl - pseudo - azimidobenzene; (XI) 1-amino-2-nitro-4-chlorobenzene --> the same coupling component; (XII) o-nitraniline --> the same coupling component. The Specification as open to inspection under Sect. 91 comprises also the manufacture of intermediate products by condensing esters of b -ketocarboxylic acids in general with 5-amino-2-aryl-pseudo-azimidobenzenes, and the manufacture of azo dyes by coupling the products in substance or on the fibre with diazo compounds in general. Additional starting materials specified for use in the preparation of the intermediates are, on the one hand, benzoylacetic and terephthaloylacetic esters, and, on the other hand, 5-amino - 6 - methyl- and 6-methoxy-2-(41-ethoxy)-phenyl-pseudo-azimidobenzene and 5-amino-2-(11-naphthyl) - pseudo - azimidobenzene. Reference is made to the use of sulphonated diazo components, e.g. sulphanilic acid, whereby wool dyestuffs are obtained, and of o-hydroxylated or o-carboxylated diazo components, which yield products which may be converted in substance or on the fibre into metalliferous dyestuffs. This subject - matter does not appear in the Specification as accepted.
GB19520/37A 1936-07-14 1937-07-14 Manufacture of dyestuffs Expired GB498051A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH498051X 1936-07-14

Publications (1)

Publication Number Publication Date
GB498051A true GB498051A (en) 1939-01-03

Family

ID=4516807

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19520/37A Expired GB498051A (en) 1936-07-14 1937-07-14 Manufacture of dyestuffs

Country Status (1)

Country Link
GB (1) GB498051A (en)

Similar Documents

Publication Publication Date Title
US2072252A (en) Coloring textile material
GB498051A (en) Manufacture of dyestuffs
US2166487A (en) Condensation products from cyanoacetic acid arylides
GB883550A (en) New triazine disazo dyestuffs and their manufacture and use
US2040927A (en) Coloration of textile materials
US2694713A (en) Fast bases of the acridone series
US2136135A (en) Pseudo-azimido-benzene-amino-acyloacetic acid esters
US2154509A (en) Certificate op correction
US2725376A (en) Ice colors of the quinoline series
US1858928A (en) Azo dyestuffs derived from amino-ethers of hydroxydiaryls
US2031651A (en) Azo dyes and methods for their preparation
US2098276A (en) Azo dyes and methods for their preparation
SU11028A1 (en) The method of obtaining water-insoluble azo dyes
GB560298A (en) Dyes and dyeing
GB379555A (en) Manufacture of azo-dyestuffs on the fibre
GB541730A (en) Improvements relating to dyestuff preparations
US1872034A (en) Azo dye from diphenyloxide derivatives
US1907793A (en) Azo dyes from orthodichlorobenzene derivatives
DE1117241B (en) Process for the production of water-insoluble azo dyes
GB1019579A (en) New disazo pigments and process for their manufacture
GB515381A (en) Manufacture of arylides of 2:3-oxynaphthalene carboxylic acid and dyestuffs
GB449267A (en) Process for producing fast prints on the fibre
GB403621A (en) Colouration of textile materials
GB430252A (en) Process for the manufacture of trisazodyestuffs
GB817311A (en) Water-insoluble monoazo dyestuffs of the hydroxynaphthoyl amine series and a process for the production thereof