EP0000505B1 - Complexes de métaux, leur procédé de préparation et leur application comme pigments - Google Patents

Complexes de métaux, leur procédé de préparation et leur application comme pigments Download PDF

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Publication number
EP0000505B1
EP0000505B1 EP78100373A EP78100373A EP0000505B1 EP 0000505 B1 EP0000505 B1 EP 0000505B1 EP 78100373 A EP78100373 A EP 78100373A EP 78100373 A EP78100373 A EP 78100373A EP 0000505 B1 EP0000505 B1 EP 0000505B1
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Prior art keywords
metal complex
complex compounds
substituted
parts
methyl
Prior art date
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EP78100373A
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German (de)
English (en)
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EP0000505A1 (fr
Inventor
Horst Dr. Tappe
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Sanofi Aventis Deutschland GmbH
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Cassella AG
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Publication date
Priority claimed from US05/819,756 external-priority patent/US4157446A/en
Application filed by Cassella AG filed Critical Cassella AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/06—Cobalt compounds
    • C07F15/065—Cobalt compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • C09B55/00—Azomethine dyes
    • C09B55/002—Monoazomethine dyes
    • C09B55/003—Monoazomethine dyes with the -C=N- group attached to an heteroring

Definitions

  • Metal complexes of the formula II the benzene nucleus I can also be substituted as stated above, in particular simply in the para position to the oxygen, that is to say the 4-position, are of particular interest.
  • reaction temperatures Temperatures from 60 ° C. to the reflux temperature of the solvent can be considered as reaction temperatures.
  • the preferred reaction temperatures are from 80 to 120 ° C.
  • the reaction is usually complete within 2 to 8 hours.
  • the azomethine formed in this reaction can be metallized without isolation, but isolation of the azomethine before the metallization is also possible. However, it is generally sufficient to metallize the azomethine in a suitable solvent without isolation.
  • the metal-free azomethine is reacted in the solvent or solvent mixture used for the azomethine condensation with a metal salt, preferably an acetate, for example copper (II) acetate, under the same conditions as in the production of azomethine. It may be advisable to keep the pH of the solution between 5 and 6, which can be done, for example, by the successive addition of sodium acetate solution.
  • the conversion of the potassium or sodium salt into the metal-free compound takes place in such a way that 19.1 parts of the product obtained are suspended in 200 parts of a mixture of 160 parts of acetic acid and 40 parts of water and the reaction mixture is concentrated to 50 parts in vacuo. After the concentrated solution has been left to stand, the metal-free compound crystallizes out. By redissolving and recrystallizing from a mixture of 160 parts of ethanol and 40 parts of water, the pure 3-formyl-4-methyl-2,6-dihydroxypyridine with a melting point of 180 to 182 ° C. is obtained.
  • alkyd-melamine resin stoving enamel Containing 2 parts by weight of a 5 weight percent of pigment, by for 60 minutes rubbing on the Paint Shaker according to Example 5 prepared alkyd-melamine resin stoving enamel be 2.5 parts by weight of mixed a Einbrenn volunteerlacks which also contains alkyd-melamine resin-based 20 weight percent TiO 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Pyridine Compounds (AREA)

Claims (11)

1. Complexes métalliques qui répondent à la formule 1
Figure imgb0019
dans laquelle X représente
Figure imgb0020
et le noyau bezénique ou naphtalénique formé par X avec la partie restante de la molécule peut également porter un ou deux substituants pris dans l'ensemble constitué par les radicaux méthyle et méthoxy, les atomes de chlore et de brome, le radical trifluorométhyle, les groupes nitro et cyano, et les radicaux―CONR1R2 et-COOR3 dans lesquels R1 et R2 représentent chacun un atome d'hydrogène ou un alkyle contenant de 1 à 4 atomes de carbone et R3 représente un alkyle contenant de 1 à 4 atomes de carbone, et Me représente un atome de nickel, de cuivre, de zinc ou de cobalt.
2. Complexes métalliques répondant à la formule Il
Figure imgb0021
dans laquelle le noyau benzénique 1 peut être substitué comme indiqué à la revendication 1.
3. Complexes métalliques selon les revendications 1 et 2, caractérisés en ce que le noyau porte pas de substituants.
4. Complexes métalliques selon les revendications 1 et 2, caractérisés en ce que lé noyau benzénique I porte un substituant en position 4.
5. Complexes métalliques selon les revendications 1, 2 et 4, caractérisés en ce que le noyau benzénique porte un atome de chlore ou de brome ou un groupe nitro ou méthoxycarbonyle.
6. Utilisation des complexes métalliques selon les revendications 1 à 5 comme pigments.
7. Utilisation des complexes métalliques selon les revendications 1 à 5 pour la pigmentation de vernis.
8. Procédé de préparation des complexes métalliques selon les revendications 1 à 5, caractérisé en ce qu'on fait réagir la formyl-3 méthyl-4 dihydroxy-2,6 pyridine, ou l'un de ses sels de métaux alcalins ou de métaux alcalino-terreux, avec un composé ortho-amino-hydroxylique répondant à la formule
Figure imgb0022
dans laquelle X a la signification donnée à la revendication 1 et le noyau benzénique ou naphtalénique formé par X avec le reset de la molécule peut également être substitué comme indiqué aux revendications 1 à 5, et on métallise le produit de condensation formé.
9. Procédé selon la revendication 8, caractérisé en ce que la réaction et/ou la métallisation sont effectuées dans un solvant organique ou dans l'eau, à des températures comprises entre 60°C et la température de reflux du solvant.
10. Procédé selon les revendications 8 ou 9, caractérisé en ce qu'on effectue la réaction et/ou la métallisation dans une atmosphère de gaz inerte.
11. Procédé selon les revendications 8 à 10, caractérisé en ce qu'on maintient un pH compris entre 5 et 6 lors de la métallisation.
EP78100373A 1977-07-29 1978-07-12 Complexes de métaux, leur procédé de préparation et leur application comme pigments Expired EP0000505B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/819,756 US4157446A (en) 1976-08-05 1977-07-29 3-Formyl-pyridines and process for making them
US819756 1977-07-29

Publications (2)

Publication Number Publication Date
EP0000505A1 EP0000505A1 (fr) 1979-02-07
EP0000505B1 true EP0000505B1 (fr) 1980-09-03

Family

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EP78100373A Expired EP0000505B1 (fr) 1977-07-29 1978-07-12 Complexes de métaux, leur procédé de préparation et leur application comme pigments

Country Status (6)

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EP (1) EP0000505B1 (fr)
JP (1) JPS5440825A (fr)
BR (1) BR7804874A (fr)
CA (1) CA1107738A (fr)
DE (1) DE2860135D1 (fr)
IT (1) IT1097775B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4494745A (en) * 1981-12-16 1985-01-22 The Ward Machinery Company Feeding apparatus for paperboard sheets
DE3315596A1 (de) * 1983-04-29 1984-10-31 Basf Ag, 6700 Ludwigshafen Verwendung von polyurethanpraepolymeren als flockungsmittel
JPS6293142A (ja) * 1985-10-18 1987-04-28 Fuji Xerox Co Ltd 用紙送行装置
JPH02225218A (ja) * 1989-02-27 1990-09-07 Tomomura Seisakusho:Kk 板状物の送り出し装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2008938A1 (en) * 1970-02-26 1971-09-09 Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen Azomethine-metal complex pigment dyes
CH562301A5 (fr) * 1971-12-13 1975-05-30 Ciba Geigy Ag

Also Published As

Publication number Publication date
IT7826284A0 (it) 1978-07-28
EP0000505A1 (fr) 1979-02-07
DE2860135D1 (en) 1980-12-11
IT1097775B (it) 1985-08-31
CA1107738A (fr) 1981-08-25
JPS5440825A (en) 1979-03-31
BR7804874A (pt) 1979-04-24

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