GB876815A - Copper complexes of monoazo-dyestuffs and process for their manufacture - Google Patents

Copper complexes of monoazo-dyestuffs and process for their manufacture

Info

Publication number
GB876815A
GB876815A GB1300/59A GB130059A GB876815A GB 876815 A GB876815 A GB 876815A GB 1300/59 A GB1300/59 A GB 1300/59A GB 130059 A GB130059 A GB 130059A GB 876815 A GB876815 A GB 876815A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydroxy
prepared
copper
dimethyl
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
GB1300/59A
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 GB876815A publication Critical patent/GB876815A/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
    • 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
    • C09B45/02—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
    • 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
    • C09B45/22—Monoazo compounds containing other metals
    • 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
    • C09B45/24—Disazo or polyazo compounds
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1:2:3- Trimethyl-4- aminopyrazolinone-(5) is obtained by nitrosation and subsequent reduction with zinc dust of 1:2:3-trimethyl-pyrazolinone-(5) in an aqueous solution, and is reacted with salicylaldehyde to form the corresponding azomethine. 1-n-butyl- or-(21-methyl-61- chlorophenyl) -2:3-dimethyl-4-amino-pyrazolinone-(5) is prepared by treating 1-n-butyl- or-(21-methyl-61-chlorophenyl) -3-methylpyrazolone-(5) with dimethyl sulphate to give 1-n-butyl- or-(21-methyl-61-chlorophenyl) - 2:3- dimethyl-pyrazolinone-(5) and then proceeding as above. 1-methyl-4-hydroxy-6-chloroquinolone-(2) is prepared by treating 2:5-dichlorobenzoic acid with methylamine in the presence of copper oxychloride to give N-methyl-5-chloro-anthranilic acid which is boiled in a mixture of glacial acetic acid and acetic anhydride. Specification 697,056 is referred to.ALSO:The invention comprises copper complexes containing in complex union 1 atom of copper and 1 mol of a monoazo dyestuff of formula:- <FORM:0876815/IV(c)/1> wherein A1 and A2 are alkyl or phenyl residues free from acid water-solubilizing groups, R is a 4-hydroxyquinolone-(2) residue free from acid water-solubilizing groups and coupled in the 3-position, and "alk" is an alkyl group. They are prepared by treating 1 mol of an azo dyestuff of the above formula with 1 mol of a copper-yielding agent such as copper sulphate or acetate in water, acetic acid or dimethyl formamide. The monoazodyestuffs are prepared by diazotizing a suitable aminopyrazolinone and coupling with a 4-hydroxy-quinolone-(2). They give yellow shades on polyacrylonitrile fibres. In examples the following dyestuffs are prepared and converted into their 1 : 1-copper complexes : aminoantipyrine --> 2 : 4-dihydroxyquinoline or N-methyl-4-hydroxy-quinolone-(2) or N-methyl-4-hydroxy-6-chloroquinoline-(2); 1 : 2 : 3-trimethyl-4-aminopyrazolinone-(5) --> N-n-butyl-4-hydroxy-quinolone-(2); isoantipyrine --> N-methyl-4-hydroxyquinolone-(2) and 1(21-methyl- 61-chlorophenyl)-2 : 3-dimethyl- 4-aminopyrazolinone-(5) --> N-methyl- 4-hydroxyquinolone-(2).
GB1300/59A 1958-02-06 1959-01-13 Copper complexes of monoazo-dyestuffs and process for their manufacture Expired GB876815A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH876815X 1958-02-06

Publications (1)

Publication Number Publication Date
GB876815A true GB876815A (en) 1961-09-06

Family

ID=4544480

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1300/59A Expired GB876815A (en) 1958-02-06 1959-01-13 Copper complexes of monoazo-dyestuffs and process for their manufacture

Country Status (1)

Country Link
GB (1) GB876815A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007007748A1 (en) * 2005-07-14 2007-01-18 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007007748A1 (en) * 2005-07-14 2007-01-18 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound
US8075976B2 (en) 2005-07-14 2011-12-13 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound
US8309196B2 (en) 2005-07-14 2012-11-13 Mitsubishi Kagaku Media Co., Ltd. Optical recording medium, optical recording material and metal complex compound

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