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Metal complexes of bis-hydrazones

Assignee: Novartis Corp
•
Filing: 1975-08-26
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Granted: 1977-04-05
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Expires: 1995-08-26
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Abstract

Abstract Bis-hydrazone metal complexes of the formula ##STR1## wherein A denotes an isocyclic or heterocyclic radical, R denotes a H atom, an alkyl group or an aryl radical, M denotes a divalent transition metal and zinc or cadmium, X 1 and X 2 independently of one another represent alkyl, cycloalkyl, aralkyl or aryl radicals, or conjointly form a fused carbocyclic or heterocyclic aromatic ring, L denotes a ligand having one or more coordinating N or S atoms, and n denotes the number 1 - 5, are useful for coloring plastic and lacquers in fast yellow to red shades.

Inventors

  • 👤 Laurent Vuitel
  • 👤 Francois L'Eplattenier
  • 👤 Andre Pugin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 20:29
CPC Classifications
C; C09; C09B; C09B57/00; C09B57/04

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 362 words
A bis-hydrazone metal complex of the formula ##STR49## wherein A denotes ##STR50## wherein M denotes a divalent transition metal, zinc or cadmium, Y 1 and Y 2 denote hydrogen, halogen, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, or nitro; Z denotes --NH-- or -oxygen-, R 8 denotes -OH, alkyl containing 1-4 carbon atoms, phenyl, phenyl substituted with halogen, alkyl of 1-4 carbon atoms, or alkoxy of 1-4 carbon atoms; R 9 denotes cyano, carboxyl, or carbamoyl; R 10 denotes hydrogen, or alkyl; Y 3 denotes hydrogen, carboxyl, carbamoyl, phenylcarbamoyl or alkoxycarbonyl containing 2-6 carbon atoms; Y 4 denotes hydrogen, halogen, methoxy, nitro or cyano; R 11 denotes alkyl of 1-4 carbon atoms, alkoxycarbonyl containing 2-5 carbon atoms, carboxyl, carbamoly, ##EQU2## wherein M 2 denotes Ca, Sr, Ba or Mn; L denotes ##STR51## wherein R' denotes hydrogen, hydroxyl, alkyl having 1-10 carbon atoms, phenalkyl containing 1-4 carbon atoms, cycloalkyl containing 5-6 carbon atoms, an aromatic group selected from the group consisting of phenyl, methylphenyl, chlorophenyl, or methoxyphenyl, amino, alkylamino containing 1-6 carbon atoms, or a group of the formulas ##STR52## wherein R 2 and R 3 denote hydrogen, alkyl of 1-6 carbon atoms, or phenyl; R'" denotes hydrogen, amino, alkyl containing 1-6 carbon atoms, phenyl, phenyl substituted by halogen, alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms; R denotes hydrogen, alkyl containing 1-4 carbon atoms or phenyl; B denotes a radical which, conjointly with the N atoms, forms a heterocyclic ring selected from the group consisting of pyridine, quinoline, piperidine, or morpholine; B 1 denotes alkylene containing 2-10 carbon atoms, phenylene, a group --Ph--X--Ph-- wherein X denotes a direct bond, --O--, --S--, methylene, ethylene, -NH-, --SO 2 --, --CO-- or --N=N--; X 3 denotes hydrogen, halogen, alkoxy containing 1-6 carbon atoms, nitro, carboxyl, carbamoyl, or alkanolyamino containing 2-6 carbon atoms; X 4 denotes hydrogen or chloro; X 5 denotes hydrogen, chloro, alkoxy, containing 1-6 carbon atoms, alkylmercapto containing 1-6 carbon atoms, phenalkoxy having an alkyl containing 1-4 carbon atoms or phenoxy; X 6 denotes hydrogen, chloro, nitro, carboxyl, carbamoyl, alkylcarbamoyl containing 2-6 carbon atoms, alkanoylamino containing 2-6 carbon atoms or phenylcarbamoyl; and m denotes the number 1-2.
Claim 2
Dependent Claim 362 words
A bis-hydrazone metal complex of the formula ##STR49## wherein A denotes ##STR50## wherein M denotes a divalent transition metal, zinc or cadmium, Y 1 and Y 2 denote hydrogen, halogen, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, or nitro; Z denotes --NH-- or -oxygen-, R 8 denotes -OH, alkyl containing 1-4 carbon atoms, phenyl, phenyl substituted with halogen, alkyl of 1-4 carbon atoms, or alkoxy of 1-4 carbon atoms; R 9 denotes cyano, carboxyl, or carbamoyl; R 10 denotes hydrogen, or alkyl; Y 3 denotes hydrogen, carboxyl, carbamoyl, phenylcarbamoyl or alkoxycarbonyl containing 2-6 carbon atoms; Y 4 denotes hydrogen, halogen, methoxy, nitro or cyano; R 11 denotes alkyl of 1-4 carbon atoms, alkoxycarbonyl containing 2-5 carbon atoms, carboxyl, carbamoly, ##EQU2## wherein M 2 denotes Ca, Sr, Ba or Mn; L denotes ##STR51## wherein R' denotes hydrogen, hydroxyl, alkyl having 1-10 carbon atoms, phenalkyl containing 1-4 carbon atoms, cycloalkyl containing 5-6 carbon atoms, an aromatic group selected from the group consisting of phenyl, methylphenyl, chlorophenyl, or methoxyphenyl, amino, alkylamino containing 1-6 carbon atoms, or a group of the formulas ##STR52## wherein R 2 and R 3 denote hydrogen, alkyl of 1-6 carbon atoms, or phenyl; R'" denotes hydrogen, amino, alkyl containing 1-6 carbon atoms, phenyl, phenyl substituted by halogen, alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms; R denotes hydrogen, alkyl containing 1-4 carbon atoms or phenyl; B denotes a radical which, conjointly with the N atoms, forms a heterocyclic ring selected from the group consisting of pyridine, quinoline, piperidine, or morpholine; B 1 denotes alkylene containing 2-10 carbon atoms, phenylene, a group --Ph--X--Ph-- wherein X denotes a direct bond, --O--, --S--, methylene, ethylene, -NH-, --SO 2 --, --CO-- or --N=N--; X 3 denotes hydrogen, halogen, alkoxy containing 1-6 carbon atoms, nitro, carboxyl, carbamoyl, or alkanolyamino containing 2-6 carbon atoms; X 4 denotes hydrogen or chloro; X 5 denotes hydrogen, chloro, alkoxy, containing 1-6 carbon atoms, alkylmercapto containing 1-6 carbon atoms, phenalkoxy having an alkyl containing 1-4 carbon atoms or phenoxy; X 6 denotes hydrogen, chloro, nitro, carboxyl, carbamoyl, alkylcarbamoyl containing 2-6 carbon atoms, alkanoylamino containing 2-6 carbon atoms or phenylcarbamoyl; and m denotes the number 1-2.
Claim 3
Dependent Claim 46 words
A bis-hydrazone metal complex according to claim 1 of the formula ##STR53## wherein A, R, M and X 3 - X 6 have the meaning indicated in claim 1, and B 1 denotes an alkylene group containing 2 - 10 C atoms, or a phenylene group.
Claim 4
Dependent Claim 31 words
A bis-hydrazone metal complex according to claim 1, wherein, in the formulae indicated, R denotes a H atom, an alkyl group containing 1 - 4 C atoms, or a phenyl group.
Claim 5
Dependent Claim 18 words
A bis-hydrazone metal complex according to claim 1, wherein M denotes a copper atom or, a Ni atom.
Claim 6
Dependent Claim 39 words
A bis-hyrazone metal complex according to claim 1, wherein X 4 and X 6 denote H or chlorine atoms, and X 3 and X 5 denote H or chlorine atoms or alkoxy groups containing 1 - 4 C atoms.
Claim 7
Dependent Claim 40 words
A bis-hydrazone metal complex according to claim 1, wherein A denotes a radical of the formula ##STR54## wherein Y 1 Y 2 denote H or halogen atoms, alkyl or alkoxy groups containing 1 - 4 C atoms, or nitro groups.
Claim 8
Dependent Claim 55 words
A bis-hydrazone metal complex according to claim 1, wherein A denotes a radical of the formula ##STR55## wherein R 8 denotes an OH group, an alkyl group containing 1 - 4 C atoms, or a phenyl radical which is optionally substituted by halogen atoms or alkyl or alkoxy groups containing 1 - 4 C atoms.
Claim 9
Dependent Claim 30 words
A bis-hydrazone metal complex according to claim 1, wherein A denotes a radical of the formula ##STR56## wherein Y 1 and Y 2 have the meaning indicated in claim 1.
Claim 10
Dependent Claim 12 words
A bis-hydrazone metal complex according to claim 1, wherein L denotes ammonia.
Claim 11
Dependent Claim 12 words
A bis-hydrazone metal complex according to claim 1, wherein L denotes ethylenediamine.
Claim 12
Dependent Claim 12 words
A bis-hydrazone metal complex according to claim 1, wherein L denotes piperazine.
Claim 13
Dependent Claim 11 words
The compound as claimed in claim 1 of the formula ##STR57##
Claim 14
Dependent Claim 11 words
The compound as claimed in claim 1 of the formula ##STR58##
Claim 15
Dependent Claim 11 words
The compound as claimed in claim 1 of the formula ##STR59##
Claim 16
Dependent Claim 11 words
The compound as claimed in claim 1 of the formula ##STR60##
Claim 17
Dependent Claim 11 words
The compound as claimed in claim 1 of the formula ##STR61##

References Cited (Backward Citations)

US3290299A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-04-04 1980-10-04 1981-04-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-04-04 1984-10-04 1985-04-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-04-04 1988-10-04 1989-04-05 $7700.00 Window Closed / Lapsed

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