GB211223A - Manufacture of new azo-dyestuffs - Google Patents

Manufacture of new azo-dyestuffs

Info

Publication number
GB211223A
GB211223A GB3125422A GB3125422A GB211223A GB 211223 A GB211223 A GB 211223A GB 3125422 A GB3125422 A GB 3125422A GB 3125422 A GB3125422 A GB 3125422A GB 211223 A GB211223 A GB 211223A
Authority
GB
United Kingdom
Prior art keywords
chlor
acid
oxynaphthalene
carboxylic acid
aminophenol
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
GB3125422A
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
Priority to GB3125422A priority Critical patent/GB211223A/en
Publication of GB211223A publication Critical patent/GB211223A/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
    • C09B29/10Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group

Landscapes

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

Abstract

Azo dyes are prepared by coupling diazo compounds with derivatives of 1-naphthol of the general formula <FORM:0211223/2/1> wherein B represents an aryl group or an NH-aryl group. Such derivatives are the 4 : 41-dioxy-dinaphthyl-ketone and its 3 : 31-dicarboxylic acid described in Specifications 181,000 and 195,513, the 4-oxynaphthalene-1-arylketones and their carboxylic acids described in Specification 203,824, and the arylamides of 1-naphthol-4-carboxylic acid. Acid dyestuffs for wool, or dyestuffs for pigments or lakes may be produced according to the nature of the diazo compound used; with unsulphonated diazo compounds fast shades may be produced by forming the dyestuffs on the fibre; red, orange-red, violet-red, &c. shades are thus obtained. The following examples are given: (1) diazotized 2-anisidine-4-sulphonic acid is coupled with 4 : 41-dioxydinaphthylketone-3 : 31-dicarboxylic acid; (2) diazotized metanilic acid is coupled with 4-oxynaphthalene-1-phenylketone or its 3-carboxylic acid; the product gives red barium lakes; 2-naphthylamine-1-or 6-sulphonic acid and the ketone also give blood-red lake dyestuffs; (3) diazotized 4-chlor-2-aminodiphenylether is coupled with 4-oxynaphthalene-1-(21-chloro)-phenylketone or its 3-carboxylic acid; (4) red shades are produced on cotton by impregnating with 4 : 41-dioxydinaphthyl-ketone, or the anilide of 1-naphthol-4-carboxylic acid, or 4-oxynaphthalene-1-phenylketone, and passing through a bath of diazotized o-toluidine, o-aminoazotoluene, or 1-chlor-2-naphthylamine, or by printing with a paste containing diazotized 5-nitro-2-anisidine. A table is also given showing the shades obtainable from the following combinations:-4 : 41-dioxydinaphthylketone or its 3 : 31-dicarboxylic acid and o-toluidine, 2 anisidine-4-sulphonic acid, o-and p-toluidine sulphonic acids (CH3 : NH2 : SO3H=1 : 2 : 4 or 1 : 4 : 3), or dianisidine: 4-oxynaphthalene-1-phenylketone or its 3-carboxylic acid and metanilic or sulphanilic acid, naphthylamine sulphonic acids 1 : 4, 2 : 1, 2 : 6, p-nitraniline, 4-chlor-2-anisidine, 4-nitro-2-toluidine, 5-nitro-2-anisidine, p-chloraniline, 2 : 5-dichloraniline, a -naphthylamine, 1-chlor-2-naphthylamine, 4-chlor-2-amino phenol-phenylether, -4-chlorphenylether, -benzylether, -p-cresylether, or -4-chlor-3-cresylether, 2-aminophenol-phenylether, 3-amino-1-methyl-4-phenol-benzylether, 4-ethylsulphon-2-aminophenol-phenylether, benzidine, dianisidine, 4 : 41-diaminodiphenylamine, 4 : 41-diaminodiphenylether, or o-aminoazotoluene : 4-oxynaphthalene-1-(21-chloro)-phenylketone or its 3-carboxylic acid and 1-chlor-2-naphthylamine, 4-ethylsulphon-2-aminophenol-benzylether, or dianisidine: 1-chloro-41-oxy-2 : 11-dinaphthylketone or its 31-carboxylic acid and 4-chlor-2-aminophenolphenyl- or benzyl-ether, or dianisidine; 1-oxynaphthalene-4-carboxylic anilide, p-toluidide, or methylanilide, and 4-chlor-2-aminophenol-phenylether. Arylamides of 1 -oxynaphthalene-4-carboxylic acid are obtained by action of aromatic amines on one of the esters of 1-oxynaphthalene-4-carboxylic acid described in Specification 181,009. 4-Chlor-3-cresylether of 4-chlor-2-aminophenol is prepared by condensing chlorcresol (OH : Cl : CH3 = 1 : 4 : 3) with 1 : 4-dichlor-2-nitrobenzene and reducing. 4-Ethylsulphon-2-aminophenol-phenyl- or benzyl-ether is obtained by reducing the corresponding nitro compound which can be made by converting 1-chlor-2-nitrobenzene-4-sulphonic chloride into the sulphonic acid, ethylating the product and exchanging Cl for O.C6H5 or O.CH2-C6H5.ALSO:Textile fibres are dyed in fast red to blue shades by impregnating with derivatives of 1-naphthol of the general formula <FORM:0211223/15/1> wherein R represents an aryl group or an NH-aryl-group, and developing or printing with a non-sulphonated diazo compound. Such derivatives are the 4 : 41-dioxy-dinaphthylketone and its 3 : 31-dicarboxylic acid described in Specifications 181,009 and 195,513, the 4-oxynaphthalene-1-arylketones and carboxylic acids described in Specification 203,824, and the arylamides of 1-naphthol-4-carboxylic acid. Examples are given in which red shades are produced on cotton by impregnating with 4 : 41-dioxydinaphthylketone, or the anilide of 1-naphthol-4-carboxylic acid, or 4-oxynaphthalene-1-phenylketone, and passing through a bath of diazotized o-toluidine, o-aminoazotoluene, or 1-chlor-2-naphthylamine, or by printing with a paste containing diazotized 5-nitro-2-anisidine. A table is also given showing the shades obtainable from the following pairs of components :-4 : 41-dioxydinaphthylketone or its 3 , 31-dicarboxylic acid and o-toluidine, 2-anisidine-4-sulphonic acid, o- or p-toluidine sulphonic acids (CH3 : NH2 : SO3H=1 : 2 : 4 or 1 : 4 : 3) or dianisidine; 4oxynaphthalene-1-phenyl-ketone or its 3-carboxylic acid and metanilic acid, sulphanilic acid, naphthylamine sulphonic acids 1 : 4, 2 : 1, 2 :6, p-nitraniline, 4-chlor-2-anisidine, 4-nitro-2-toluidine, 5-nitro-2-anisidine, p-chloraniline, 2 : 5-dichloraniline, a -naphthylamine, 1-chlor-2-naphthylamine, 4-chlor-2-aminophenol-phenylether, 4-chlorphenylether, -benzylether, -p-cresylether, or 4-chlor-3-cresylether, 2-aminophenol-phenylether, 3-amino-1-methyl-4-phenol-benzylether, 4-ethyl-sulphon-2-aminophenol-phenylether, benzidine, dianisidine, 4 : 41-diamino-diphenylamine, 4 : 41 diamino - diphenylether, or o - aminoazotoluene: 4 - oxynaphthalene - 1 - (21 - chloro) - phenylketone or its 3-carboxylic acid and 1-chlor-2-naphthylamine, 4-ethylsulphon-2-aminophenolbenzylether, or dianisidine : 1-chlor-41-oxy-2 : 11-dinaphthylketone or its 31-carboxylic acid and 4-chlor-2-aminophenol-phenyl-or-benzyl-ether, or dianisidine; 1-oxynaphthalene-4-carboxylic anilide, p-toluidide, or methylanilide, and 4-chlor-2-aminophenol-phenylether.
GB3125422A 1922-11-15 1922-11-15 Manufacture of new azo-dyestuffs Expired GB211223A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3125422A GB211223A (en) 1922-11-15 1922-11-15 Manufacture of new azo-dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3125422A GB211223A (en) 1922-11-15 1922-11-15 Manufacture of new azo-dyestuffs

Publications (1)

Publication Number Publication Date
GB211223A true GB211223A (en) 1924-02-15

Family

ID=10320339

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3125422A Expired GB211223A (en) 1922-11-15 1922-11-15 Manufacture of new azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB211223A (en)

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