GB470356A - Manufacture of dyestuffs containing metal in complex union - Google Patents

Manufacture of dyestuffs containing metal in complex union

Info

Publication number
GB470356A
GB470356A GB6685/36A GB668536A GB470356A GB 470356 A GB470356 A GB 470356A GB 6685/36 A GB6685/36 A GB 6685/36A GB 668536 A GB668536 A GB 668536A GB 470356 A GB470356 A GB 470356A
Authority
GB
United Kingdom
Prior art keywords
acid
copper
treated
glycocoll
dyestuff
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
GB6685/36A
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
Priority to CH193242D priority Critical patent/CH193242A/en
Priority to CH193244D priority patent/CH193244A/en
Priority to CH190154D priority patent/CH190154A/en
Priority to CH193241D priority patent/CH193241A/en
Priority to CH193238D priority patent/CH193238A/en
Priority to CH193243D priority patent/CH193243A/en
Priority to CH193237D priority patent/CH193237A/en
Application filed by Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Priority to GB6685/36A priority patent/GB470356A/en
Priority to FR818329D priority patent/FR818329A/en
Publication of GB470356A publication Critical patent/GB470356A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
    • C09B1/06—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/12—Dyes containing sulfonic acid groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/48—Preparation from other complex metal compounds of azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Abstract

Complex metal compounds of dyestuffs are made by treating in the presence of an aliphatic aminocarboxylic acid or a salt thereof a dyestuff containing a group capable of binding metal in complex union with an agent yielding a metal of atomatic weight between 58 and 64, i.e. copper, nickel and cobalt. The dyestuff may also be treated with a copper, nickel or cobalt salt of an aliphatic aminocarboxylic acid or a dyestuff containing copper, nickel or chromium in complex combination may be treated with an aliphatic aminocarboxylic acid or a salt thereof. Water soluble products are obtained useful for dyeing wool, silk and leather. The dyeing of an oxide film on aluminium is also mentioned. In examples: (1) the dyestuff 4 : 4<1>-diaminodiphenylurea \sQ salicylic acid is treated with ammoniacal copper oxide and the insoluble product mixed with sodium glycocoll; (2) the dyestuff (salicylic acid-azo-hydroquinone dimethylether-azo)2-dinaphthyl J acid is treated with copper glycocoll or with a copper salt of ethyl- or diethylaminoacetic acid, aminosuccinic acid, a -aminopropionic acid or a -amino-butyric acid; (3) the dyestuff (salicylic acid-azo-p-cresol methyl ether-azo)2-dinaphthyl J acid is treated with copper sulphate and the insoluble product treated with glycocoll and sodium carbonate; ethyl glycocoll and a -amino-propionic or butyric acid may be used; (4) the starting dyestuff of (2) is converted into an insoluble copper compound by means of copper sulphate or ammoniacal copper oxide and ground with sodium glycocoll; (5) the dyestuffs salicylic acid-azo-p-cresol methyletherazo - dinaphthyl J acid - azo - hydroquinone-dimethylether-azo-salicylic acid, [5-nitrophenol-2-azo-dinaphthyl J acid-azo]2-p : p<1>-dihydroxy-diphenylsulphone, salicyclic acid - azo - naphthalene - 6 - sulphonic acid - azo - naphthalene-6-sulphonic acid-azo-J acid and the dyestuffs obtained by condensing monoacetyl-p-phenylenediamine --> salicylic acid or 4-amino-1-phenol-2-carboxylic acid --> m-phenylenediamine with 4 : 4<1>-dinitrostilbene-2 : 2<1>disulphonic acid (cf. Specification 348,283) are treated with copper glycocoll; (6) the mixed urea from 4-chloraniline-3-sulphonic acid --> cresidine and p-aminosalicylic acid --> aniline, the mixed urea from metanilic acid --> o-anisidine and p-aminosalicylic acid --> aniline and the dyestuff o-cresotinic acid \sM benzidine --> 1-(m-sulphophenyl)-3-methyl-5-pyrazolone are treated with copper glycocoll; (7) the dyestuff 6-nitro-2-aminophenol-4-sulphonic acid --> b -naphthol is treated with copper glycocoll and the product precipitated on a substratum of aluminium sulphate and heavy spar; the dyestuffs 5-nitro-2-aminophenol --> 2-naphthylamine-6-sulphonic acid, 4-nitro-2-aminophenol-6-sulphonic acid --> 1-phenyl-3-methyl-5-pyrazolone, 4-chlor-2-aminophenol --> 2-naphthol - 6 - sulphonic acid, 4-nitro-2-aminophenol --> resorcinol or 1-phenyl-3-methyl-5-pyrazolone, and 1-amino-2-naphthol-4-sulphonic acid --> a - or b -naphthol may be similarly treated; (8) the dyestuff 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol is similarly treated; (9) the dyestuff 2-amino-1-naphthol-4-sulphonic acid --> b -naphthol is treated with cobalt glycocoll; (10) 1 : 2-dihydroxyanthraquinone - 3 - sulphonic acid (Alizarine Red S) is treated with copper glycocoll; (11) 1 : 2 : 4 : 5 : 6 : 8-hydroxy-anthraquinone-3 : 7-disulphonic acid (Anthracene Blue SWX) is treated with copper glycocoll; the product may be used for dyeing oxide films on aluminium; (12) highly oxidized log-wood extract is treated with copper glycocoll; (13) the dyestuffs Naphthochrome Green G and Naphthochrome Azurine B are treated with copper glycocoll; (14) the copper or nickel compound of the dyestuff from 6-nitro-1-diazo-2-naphthol-4-sulphonic acid and b -naphthol is treated with sodium glycocoll; the copper and nickel compounds of the dyestuff 1-amino-2-naphthol-4-sulphonic acid --> a - or b -naphthol may be similarly treated; (15) the starting dyestuff of (3) is treated with copper or nickel sulphate and the insoluble compound stirred with sodium carbonate and glycocoll; (16) the dyestuff from 6-nitro-1-diazo-2-naphthol-4-sulphonic acid and b -naphthol is treated with sodium glycocoll and copper sulphate or other copper sulphate or a nickel or cobalt salt; (17) the starting dyestuff of (2) is treated with sodium glycocoll, sodium carbonate and copper sulphate or other salt. Samples have been furnished under Sect. 2 (5) of the dyestuffs obtained by treating (1) Brilliant Alizarine Blue SD with copper glycocoll; (2) Gallocyanine DH with copper diethanolamino acetate (from copper chloracetate and diethanolamine); and (3) Gallein with copper diethylamino acetate. Specifications 446,746 and 458,501 also are referred to.
GB6685/36A 1936-02-27 1936-03-05 Manufacture of dyestuffs containing metal in complex union Expired GB470356A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CH193242D CH193242A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193244D CH193244A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH190154D CH190154A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193241D CH193241A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193238D CH193238A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193243D CH193243A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
CH193237D CH193237A (en) 1936-02-27 1936-02-27 Process for the preparation of a complexed metal-containing dye.
GB6685/36A GB470356A (en) 1936-02-27 1936-03-05 Manufacture of dyestuffs containing metal in complex union
FR818329D FR818329A (en) 1936-02-27 1937-02-24 Dyes containing metals bound in the form of metal complexes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH190154T 1936-02-27
GB6685/36A GB470356A (en) 1936-02-27 1936-03-05 Manufacture of dyestuffs containing metal in complex union

Publications (1)

Publication Number Publication Date
GB470356A true GB470356A (en) 1937-08-13

Family

ID=9818927

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6685/36A Expired GB470356A (en) 1936-02-27 1936-03-05 Manufacture of dyestuffs containing metal in complex union

Country Status (3)

Country Link
CH (7) CH193241A (en)
FR (1) FR818329A (en)
GB (1) GB470356A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399186A (en) * 1962-01-24 1968-08-27 Kanegafuchi Spinning Co Ltd Cationic metal-containing azo dyes from 8-hydroxyquinoline
US4801302A (en) * 1986-05-07 1989-01-31 L'oreal Process for dyeing human hair with brazilin or its hydroxyl derivative and compositions employed
CN116376312A (en) * 2023-03-31 2023-07-04 南通大学 High-temperature-resistant red vegetable dye and preparation method and application thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH618728A5 (en) 1975-11-18 1980-08-15 Ciba Geigy Ag
LU83177A1 (en) * 1981-02-27 1982-09-10 Oreal USE OF HYDROXYANTHRAQUINONES FOR COLORING HUMAN KERATINIC FIBERS, METHOD AND COMPOSITION USING THE SAME
US4901824A (en) * 1984-12-12 1990-02-20 Shimano Industrial Company Limited Bicycle brake shoe having slit surfaces

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399186A (en) * 1962-01-24 1968-08-27 Kanegafuchi Spinning Co Ltd Cationic metal-containing azo dyes from 8-hydroxyquinoline
US4801302A (en) * 1986-05-07 1989-01-31 L'oreal Process for dyeing human hair with brazilin or its hydroxyl derivative and compositions employed
GB2190104B (en) * 1986-05-07 1990-05-02 Oreal Process for dyeing human hair with brazilin or its hydroxyl derivatives and compositions employed therein
CN116376312A (en) * 2023-03-31 2023-07-04 南通大学 High-temperature-resistant red vegetable dye and preparation method and application thereof

Also Published As

Publication number Publication date
CH193237A (en) 1937-09-30
CH193243A (en) 1937-09-30
FR818329A (en) 1937-09-24
CH193238A (en) 1937-09-30
CH193242A (en) 1937-09-30
CH193241A (en) 1937-09-30
CH193244A (en) 1937-09-30
CH190154A (en) 1937-04-15

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