CA953291A - Basic azo compounds, their production and use - Google Patents

Basic azo compounds, their production and use

Info

Publication number
CA953291A
CA953291A CA051,493A CA51493A CA953291A CA 953291 A CA953291 A CA 953291A CA 51493 A CA51493 A CA 51493A CA 953291 A CA953291 A CA 953291A
Authority
CA
Canada
Prior art keywords
production
azo compounds
basic azo
basic
compounds
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
CA051,493A
Other languages
English (en)
Inventor
Hermann Burkhard
Roland Entschel
Curt Mueller
Willy Steinemann
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.)
Sandoz Patent Ltd
Original Assignee
Sandoz Patent Ltd
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 Sandoz Patent Ltd filed Critical Sandoz Patent Ltd
Application granted granted Critical
Publication of CA953291A publication Critical patent/CA953291A/en
Expired legal-status Critical Current

Links

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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
    • 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
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/08—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing heterocyclic rings
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
    • C09B62/447—Azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA051,493A 1968-05-15 1969-05-14 Basic azo compounds, their production and use Expired CA953291A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH721868A CH503781A (de) 1968-05-15 1968-05-15 Verfahren zur Herstellung von basischen Farbstoffen
CH1119568A CH506591A (de) 1968-05-15 1968-07-25 Verfahren zur Herstellung von Monoazoverbindungen
CH1158168 1968-08-02
CH1213668A CH506592A (de) 1968-05-15 1968-08-13 Verfahren zur Herstellung von basischen Verbindungen der Azoreihe
CH1689868 1968-11-13
CH1758068A CH520753A (de) 1968-05-15 1968-11-26 Verfahren zur Herstellung von Azoverbindungen

Publications (1)

Publication Number Publication Date
CA953291A true CA953291A (en) 1974-08-20

Family

ID=27543801

Family Applications (1)

Application Number Title Priority Date Filing Date
CA051,493A Expired CA953291A (en) 1968-05-15 1969-05-14 Basic azo compounds, their production and use

Country Status (9)

Country Link
US (1) US4213898A (fr)
JP (2) JPS5227174B1 (fr)
BE (2) BE727081A (fr)
CA (1) CA953291A (fr)
CH (4) CH503781A (fr)
DE (3) DE1901711C3 (fr)
FR (2) FR2024762B1 (fr)
GB (5) GB1274941A (fr)
NL (2) NL160596C (fr)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH552661A (de) * 1968-11-12 1974-08-15 Ciba Geigy Ag Verfahren zur herstellung neuer azofarbstoffe.
DE1813385A1 (de) * 1968-12-07 1970-07-02 Cassella Farbwerke Mainkur Ag Verfahren zum Faerben und Bedrucken von Fasergut aus synthetischen Materialien
DE2251719A1 (de) * 1972-10-21 1974-04-25 Basf Ag 6700 Ludwigshafen Dispersionsfarbstoffe der 2,6diaminopyridinreihe
DE2120095A1 (de) * 1971-04-24 1972-11-02 Cassella Farbwerke Mainkur Ag, 6000 Frankfurt Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung
US3954396A (en) * 1971-09-24 1976-05-04 Cassella Farbwerke Mainkur Aktiengesellschaft Dyeing synthetic materials with a dodecyl benzoicacid ester-azo-(3-cyano-4-methyl-6-hydroxy-2-pyridone)
DE2222099A1 (de) * 1972-05-05 1973-11-22 Hoechst Ag Basische azofarbstoffe, ihre herstellung und verwendung
US4005069A (en) * 1972-05-15 1977-01-25 Sandoz Ltd. Azo dyes having a 3-halo-4-cyano or acyl-6-hydroxypyridone-2 coupling component radical
DE2300940A1 (de) * 1973-01-10 1974-07-18 Basf Ag Azopigmente
US4038268A (en) * 1973-02-14 1977-07-26 Bayer Aktiengesellschaft Process for preparing azo dyestuffs containing 2,4,6-tri-amino-3-(cyano ester or carbonamide)pyridine
DE2345161C2 (de) * 1973-09-07 1982-11-04 Wilhelm 2000 Hamburg Genz Verfahren und Vorrichtung zum Regenerieren eines Lösungsmittels bei der chemischen Reinigung
AR207988A1 (es) 1974-07-16 1976-11-22 Ciba Geigy Ag Complejos de cobre niquel cromo y cobalto de colorantes azoicos y azometinicos y procedimiento para su obtencion
GB1552220A (en) * 1975-12-17 1979-09-12 Ici Ltd Azo dyestuffs
CH621813A5 (fr) * 1976-03-30 1981-02-27 Sandoz Ag
IT1061811B (it) * 1976-06-25 1983-04-30 Montedison Spa Coloranti monoazoici gialli insolubili in acqua
CH623844A5 (fr) * 1976-09-23 1981-06-30 Sandoz Ag
FR2381808A1 (fr) * 1976-12-27 1978-09-22 Sandoz Sa Nouveaux colorants azoiques basiques exempts de groupes sulfo et leur preparation
CH627201A5 (fr) * 1977-03-14 1981-12-31 Sandoz Ag
IT1088557B (it) * 1977-11-29 1985-06-10 Montedison Spa Coloranti cationici monoazoici idrosolubili
DE2842186A1 (de) * 1978-09-28 1980-04-10 Basf Ag Azofarbstoffe
DE3021555A1 (de) * 1979-06-18 1981-01-22 Sandoz Ag Pyridon-dispersionsfarbstoffe
JPS5910748B2 (ja) * 1980-05-12 1984-03-10 チバ−ガイギ−・アクチエンゲゼルシヤフト アゾ染料
JPS5910749B2 (ja) * 1980-05-13 1984-03-10 チバ−ガイギ−、アクチエンゲゼルシヤフト アゾ染料
FR2536082B1 (fr) * 1982-11-11 1986-08-22 Sandoz Sa Nouveaux composes azoiques, leur preparation et leur utilisation comme colorants
CH663417A5 (de) * 1984-05-19 1987-12-15 Sandoz Ag Basische verbindungen, deren herstellung und verwendung.
DE3419138A1 (de) * 1984-05-23 1985-11-28 Basf Ag, 6700 Ludwigshafen Azoreaktivfarbstoffe
EP0268897A1 (fr) * 1986-11-15 1988-06-01 BASF Aktiengesellschaft Colorants azoiques de la série des pyridones
FR2637289B1 (fr) * 1988-10-05 1992-11-06 Sandoz Sa Composes azoiques de la serie de la pyridone, leur preparation et leur utilisation comme colorants
DE4227590A1 (de) * 1992-08-20 1994-02-24 Basf Ag Azofarbstoffe mit einer Kupplungskomponente aus der Reihe der N-(Hydroxysulfonylphenylalkyl)pyridone
GB2315493B (en) * 1996-07-24 2001-01-03 Lexmark Int Inc Ink jet ink dyes
DE19714582A1 (de) * 1997-04-09 1998-10-15 Bayer Ag Verfahren zur Herstellung stark basischer Anionenaustauscher mit Ethylenoxid
AU7667798A (en) * 1997-06-21 1999-01-04 Avecia Limited Pyridonazo dyes and inks containing them
JP4530570B2 (ja) * 2001-04-09 2010-08-25 富士フイルム株式会社 着色画像のオゾンガス堅牢性改良方法
JP4512507B2 (ja) * 2004-07-09 2010-07-28 富士フイルム株式会社 ピリドンアゾ化合物およびこの互変異性体を含み着色剤含有硬化性組成物、カラーフィルタおよびその製造方法
JP4727351B2 (ja) * 2005-04-12 2011-07-20 富士フイルム株式会社 感光性組成物、カラーフィルタ及びその製造方法
JP2007058085A (ja) * 2005-08-26 2007-03-08 Fujifilm Holdings Corp 着色剤含有硬化性組成物、カラーフィルタ及びその製造方法
JP2009280691A (ja) * 2008-05-22 2009-12-03 Sumitomo Chemical Co Ltd アゾ化合物又はその塩
US9382426B2 (en) 2012-01-20 2016-07-05 Canon Kabushiki Kaisha Water-insoluble coloring compound, ink, thermal transfer recording sheet, and color filter resist composition
US20150140487A1 (en) * 2012-06-27 2015-05-21 Canon Kabushiki Kaisha Yellow toner

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR767690A (fr) * 1934-07-20
US2099525A (en) * 1935-02-19 1937-11-16 Gen Aniline Works Inc Production of water-soluble azo dyestuffs
US2234723A (en) * 1939-10-11 1941-03-11 Eastman Kodak Co Azo compounds and material colored therewith
US2431190A (en) * 1946-06-12 1947-11-18 Gen Aniline & Film Corp Diazotype prints with hydroxy pyridone couplers
BE625467A (fr) * 1961-12-01
DE1901712U (de) 1961-12-04 1964-10-08 Licentia Gmbh Kuehlschrank mit schaumstoffisolation.
DE1286666B (de) * 1962-04-05 1969-01-09 Hoechst Ag Verfahren zur Herstellung von wasserloeslichen, kationischen Farbstoffen
CH464392A (de) * 1964-03-25 1968-10-31 Sandoz Ag Verfahren zur Herstellung von basischen Farbstoffen
GB1047293A (fr) * 1964-04-21 1900-01-01
GB1052002A (fr) * 1964-04-21
DE1544362A1 (de) * 1964-07-16 1969-07-31 Basf Ag Verfahren zur Herstellung von Disazofarbstoffen
CH469785A (de) * 1964-08-28 1969-03-15 Sandoz Ag Verfahren zur Herstellung von basischen Farbstoffen
FR1489492A (fr) * 1965-08-13 1967-07-21 Cassella Farbwerke Mainkur Ag Nouveaux colorants azoïques insolubles dans l'eau et leur préparation
CH482785A (de) * 1966-05-23 1969-12-15 Ciba Geigy Verfahren zur Herstellung neuer basischer Azofarbstoffe
DE1956142U (de) 1966-07-21 1967-02-23 Constructa Werke G M B H Schlauchverbindung.
DE1644220A1 (de) * 1967-07-15 1971-05-06 Bayer Ag Azofarbstoffe
US3577404A (en) * 1967-08-11 1971-05-04 Sandoz Ltd Basic pyrazolone monoazo dyes containing an ammonium or hydrazinium group
US3487060A (en) * 1968-02-23 1969-12-30 Du Pont Production of granular polyvinyl alcohol

Also Published As

Publication number Publication date
BE727081A (fr) 1969-07-01
CH506591A (de) 1971-04-30
NL146198B (nl) 1975-06-16
CH503781A (de) 1971-02-28
GB1274941A (en) 1972-05-17
DE1901711A1 (de) 1970-04-09
DE1901711C3 (de) 1985-05-30
DE1924770C2 (de) 1985-10-17
CH520753A (de) 1972-03-31
CH506592A (de) 1971-04-30
GB1274944A (en) 1972-05-17
FR2008615A1 (fr) 1970-01-23
DE1966451A1 (de) 1972-09-28
NL160596B (nl) 1979-06-15
DE1966451C2 (de) 1982-07-29
JPS5227174B1 (fr) 1977-07-19
FR2008615B1 (fr) 1973-11-30
US4213898A (en) 1980-07-22
GB1274942A (en) 1972-05-17
GB1274943A (en) 1972-05-17
FR2024762A1 (fr) 1970-09-04
BE733186A (fr) 1969-11-03
DE1924770A1 (de) 1970-11-19
FR2024762B1 (fr) 1973-02-02
NL6900655A (fr) 1970-01-27
GB1273748A (en) 1972-05-10
JPS5216729B1 (fr) 1977-05-11
NL160596C (nl) 1979-06-15
NL6907356A (fr) 1969-11-18

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