DE2344443A1 - PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN - Google Patents

PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN

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Publication number
DE2344443A1
DE2344443A1 DE19732344443 DE2344443A DE2344443A1 DE 2344443 A1 DE2344443 A1 DE 2344443A1 DE 19732344443 DE19732344443 DE 19732344443 DE 2344443 A DE2344443 A DE 2344443A DE 2344443 A1 DE2344443 A1 DE 2344443A1
Authority
DE
Germany
Prior art keywords
phenyl
dichloro
xanthylium
chlorides
formula
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.)
Pending
Application number
DE19732344443
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German (de)
Inventor
Rudolf Dipl Chem Dr Neeb
Theodor Dipl Chem Dr Papenfuhs
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Hoechst AG
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Hoechst 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 Hoechst AG filed Critical Hoechst AG
Priority to DE19732344443 priority Critical patent/DE2344443A1/en
Priority to DE19742435653 priority patent/DE2435653A1/en
Priority to CH1184374A priority patent/CH608799A5/en
Priority to NL7411564A priority patent/NL7411564A/en
Priority to CH93978A priority patent/CH613707A5/en
Priority to AU72894/74A priority patent/AU483678B2/en
Priority to JP9999174A priority patent/JPS5082071A/ja
Priority to IT2685874A priority patent/IT1020394B/en
Priority to DK466174A priority patent/DK466174A/da
Priority to GB3866874A priority patent/GB1432754A/en
Priority to BE148187A priority patent/BE819522A/en
Priority to FR7430017A priority patent/FR2242390A1/fr
Priority to IN1992/CAL/1974A priority patent/IN142239B/en
Publication of DE2344443A1 publication Critical patent/DE2344443A1/en
Pending legal-status Critical Current

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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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132—Chemical colour-forming components; Additives or binders therefor
    • B41M5/136—Organic colour formers, e.g. leuco dyes
    • B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/323—Organic colour formers, e.g. leuco dyes
    • B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/3275—Fluoran compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes 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 in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

FARBWERKE HOECHST AG vormals Meister Lucius & BrüningFARBWERKE HOECHST AG formerly Master Lucius & Brüning

Aktenzeichen: HOE 73/F 272File number: HOE 73 / F 272

Datums 3. September 1973 Dr.ST/PRDate September 3, 1973 Dr.ST/PR

Verfahren zur Herstellung von 3*6-Dichlor-9-phenyl-xanthylium» Chloriden und 3»6-Dichlor-9-phenyl-XEnchen-9-olenProcess for the preparation of 3 * 6-dichloro-9-phenyl-xanthylium »chlorides and 3» 6-dichloro-9-phenyl-XE n chen-9-ols

Die vorliegende Erfindung betrifft ein verbessertes Verfahren zur Herstellung von 3f6-Dichlor-9-phenyl-xanthyliumchloriden und 3t6-Dichlor~9-phenyl-xanthen-9-olen.The present invention relates to an improved process for the preparation of 3f6-dichloro-9-phenyl-xanthylium chlorides and 3 t 6-dichloro-9-phenyl-xanthen-9-ols.

3t6-Dichlor-9-phenyl-xanthyliumchlorid ist ein wertvolles Zwischenprodukt zur Herstellung von Xanthenfarbstoffen (vgl. die deutschen Reichspatente 5I 3^8 und 52 030).3t6-dichloro-9-phenyl-xanthylium chloride is a valuable intermediate for the production of xanthene dyes (cf. the German imperial patents 5I 3 ^ 8 and 52 030).

Es kann in einem zweistufigen Verfahren erhalten werden, indem man zunächst Benzotrichlorid mit Resorcin in einem indifferenten, ox-ganischen Lösungsmittel zum Resorcinbenzein umsetzt (vgl. Liebigs Ann. 217 (I883), S. 23^ und J.pr.Ch. [2] , Ji^" (1912), S. Zkk) und dieses nach Isolierung und Reinigung durch' Behandeln mit Phosphorpentachlorid, gegebenenfalls unter Zusatz von Phosphoroxychlorid, in das 3»6-Dichlor-9-phenyl-xanthyliumchlorid überführt (vgl. J. Chem. Soc. J9J? (1911), S. 550, dito 105 (191*01 S. 259 sowie das deutsche Reichspatent 5IIt can be obtained in a two-stage process by first reacting benzotrichloride with resorcinol in an inert ox-ganischen solvent to resorcinol benzein (cf. Liebigs Ann. 217 (1883), p. 23 ^ and J.pr.Ch. [2 ], Ji ^ "(1912), S. Zkk) and this after isolation and purification by treatment with phosphorus pentachloride, optionally with the addition of phosphorus oxychloride, converted into the 3-6-dichloro-9-phenylxanthylium chloride (cf. J. Chem. Soc. J9J? (1911), p. 550, ditto 105 (191 * 01 p. 259 as well as the German imperial patent 5I

5098U/109S5098U / 109S

Dieses Verfahren besitzt den Nachteil, daß es in zwei Stufen und teilweise in organischen Lösungsmitteln durchgeführt wird. Außerdem fällt das in der ersten Stufe entstehende Resorcinben-2ein in stärk verunreinigter Form an, so daß es gereinigt werden muß. Da es in Lösungsmitteln schwer löslich ist, bereitet auch die Reinigung aus Lösungsmitteln Schwierigkeiten.This process has the disadvantage that it is carried out in two stages and partly in organic solvents. In addition, the resorcinben-2 produced in the first stage falls in a highly contaminated form, so that it has to be cleaned. Since it is sparingly soluble in solvents, it also prepares Solvent cleaning difficulties.

Es wurde nun gefunden, daß man 3»6-Dichlor-9-phenyl-xanthyliumchloride der Formel (i)It has now been found that 3 »6-dichloro-9-phenyl-xanthylium chlorides of formula (i)

(D(D

und 3,6-Dichlof-9-phenyl-xanthen-9-ole der Formel (il)and 3,6-Dichlof-9-phenyl-xanthene-9-ols of the formula (II)

(II)(II)

in welchen R1 und R„ gleich oder verschieden sind und jedes ein Wasserstoffatom oder ein Halogenatom, insbesondere ein Chlor-in which R 1 and R "are the same or different and each is a hydrogen atom or a halogen atom, in particular a chlorine atom

5098U/10965098U / 1096

oder Pluoratom, bedeutet, wesentlich einfacher und in besserer Ausbeute und Reinheit erhält, wenn man ein Benzotrichlorid der Formel (ill)or Pluoratom, means much simpler and better Yield and purity are obtained by using a benzotrichloride of the formula (ill)

(III)(III)

in welcher R1 und R2 die obigen Bedeutungen haben, mit Resorcin in Gegenwart von überschüssigem Phosphoroxychlorid umsetzt und gegebenenfalls die erhaltenen 3»6-Dichlor-9-phenyl-xanthyliurachloride der Formel I durch Behandlung mit Alkalien in die 3,6-Dichlor-9-phenyl-xanthen-0—öle der Formel II überführt.in which R 1 and R 2 have the above meanings, reacted with resorcinol in the presence of excess phosphorus oxychloride and optionally the resulting 3 »6-dichloro-9-phenyl-xanthyliurachloride of the formula I by treatment with alkalis in the 3,6-dichloro 9-phenyl-xanthene- 0 oils of the formula II converted.

Das erfindungsgemäße Verfahren wird in der ¥eise durchgeführt, daß man eine Mischung aus 1 Mol eines Benzotrichlorids der Formel III, 2 Mol Resorcin und etwa 3 bis h Mol Phosphoroxychlorid etwa 15 bis 20. Stunden auf etwa kO° C - 70° C, vorzugsweise 50 bis 60° C und anschließend etwa 2 bis 3 Stunden auf etwa 90°bis 125° C, vorzugsweise 100°bis 120° C erwärmt.The process according to the invention is carried out in such a way that a mixture of 1 mole of a benzotrichloride of the formula III, 2 moles of resorcinol and about 3 to h moles of phosphorus oxychloride for about 15 to 20 hours at about kO ° C - 70 ° C, preferably 50 to 60 ° C and then heated to about 90 ° to 125 ° C, preferably 100 ° to 120 ° C for about 2 to 3 hours.

Das so erhaltene 3*.6-Dichlor~9-phenyl-xanthyliumchlorid kann direkt für weitere Synthesen verwendet oder durch Zugabe von Wasser isoliert werden. Zweckmäßig überführt man es jedoch in das entsprechende Xanthen-9-ol, indem man die Lösung des 3t6-Dichlor-9-phenyl-xanthyliumchlorids auf etwa 70 bis 80 C abkühlt, sie dani/Langsam bei etwa 60 C - 100 C, vorzugsweise 70 - 90° C in überschüssiges Alkali, beispielsweise in wäßrige Natronlauge oder Kalilauge, einträgt und das abgeschiedene 3 »6-Dichlor-9-phenyl-xanthen-9-ol anschließend isoliert.The 3 * .6-dichloro-9-phenyl-xanthylium chloride thus obtained can used directly for further syntheses or isolated by adding water. However, it is expedient to transfer it to the corresponding xanthen-9-ol by adding the solution of 3t6-dichloro-9-phenyl-xanthylium chloride cools to about 70 to 80 ° C, dani / slowly at about 60 ° to 100 ° C., preferably 70-90 ° C. in excess alkali, for example in aqueous sodium hydroxide solution or potassium hydroxide solution, and the separated 3 »6-dichloro-9-phenyl-xanthene-9-ol then isolated.

Die so erhältlichen 3,6~Dichlor-9-phenyl-xanthen-9-ole sind gut filtrierbare, gegen Alkalien sehr beständige Verbindungen, dieThe 3,6 ~ dichloro-9-phenyl-xanthene-9-ols obtainable in this way are good filterable compounds, very resistant to alkalis, which

5098U/109&5098U / 109 &

bevorzugt für die Herstellung von Xanthenfarbstoff en verwendet werden.preferably used for the production of xanthene dyes will.

Gegentiber den bekannten Verfahren besitzt das erfindungsgemäße Verfahren den Vorteil, daß es ohne organische Lösungsmittel durchgeführt werden kann und ohne Isolierung von Zwischenstufen in hohen Ausbeuten zu den 3»ö-Dichlor-0—phenyl-xanthenverbinduhgen führt.In contrast to the known processes, the process according to the invention has the advantage that it can be carried out without organic solvents and leads to the 3 » 6-dichloro-0- phenyl-xanthene compounds in high yields without isolating intermediate stages.

Das nachstehende Beispiel dient zu seiner Erläuterung. Gewichtsteile und Volumenteile verhalten sich zueinander wie Kilogramm zu Liter.The following example serves to explain it. Parts by weight and parts by volume relate to one another like kilograms to liters.

Beispielexample

Zu einer Mischung aus 110 Gewichtsteilen Resorcin und 251 Gewichtsteilen Phosphoroxychlorid tropft man bei 50 bis 55 C innerhalb von 3 Stunden 98 Gewichtsteile Benzotrichlorid. Dann rührt man etwa 16 Stunden bei 50 bis 55° C, erwärmt dann in 1 Stunde auf i'iO° C und hält 2 Stunden bei dieser Temperatur. Anschließend tropft man die auf 80° C abgekühlte Reaktionsmischung zu einer 70 bis 75 0 warmen Mischung aus 2000 Volumenteilen Wasser und 750 Gewichtsteilen 33 #iger Natronlauge, wobei die Geschwindigkeit des Zutropfens so gewählt wird, daß die Vorlage schwach unter Rückfluß siedet.Dann rührt man ohne Heizung 15 Minuten nach, wobei sich das Gemisch auf ca. 80 C abkühlt, saugt den Niederschlag ab, wäscht dreimal mit Je 250 Volumenteilen heißem Wasser, saugt gut trocken und trocknet bei 60° C. Man erhält 13** Gewichtsteile (= 78,1 # der Theorie) 3,6-Dichlor-9-phenyl-xanthen-9-ol. 98 parts by weight of benzotrichloride are added dropwise at 50 to 55 ° C. over the course of 3 hours to a mixture of 110 parts by weight of resorcinol and 251 parts by weight of phosphorus oxychloride. The mixture is then stirred for about 16 hours at 50 to 55 ° C., then heated to 10 ° C. in 1 hour and kept at this temperature for 2 hours. The reaction mixture, which has been cooled to 80 ° C., is then added dropwise to a 70-75 ° C. mixture of 2000 parts by volume of water and 750 parts by weight of 33% sodium hydroxide solution, the speed of the dropping being chosen so that the initial charge is gently refluxed. Then the mixture is stirred without heating 15 minutes, during which the mixture is cooled to about 80 C, the precipitate is suctioned off, washed three times with 250 parts by volume of hot water, sucked dry well and dried at 60 ° C. this gives 13 ** parts by weight (= 78 , 1 # of theory) 3,6-dichloro-9-phenyl-xanthen-9-ol.

Analog lassen sich das 3,6-Dichlor-9-(2'-chlorphenyl)-, -9-(4·- chlorphenyl)-, -9-(2»,4f-dichlorphenyl)- oder das -9-(2'-fluorphenyl)-xanthen-9-ol herstellen.The 3,6-dichloro-9- (2'-chlorophenyl) -, -9- (4 · - chlorophenyl ) -, -9- (2 », 4 f -dichlorophenyl) - or the -9- ( Prepare 2'-fluorophenyl) -xanthen-9-ol.

5098U/1096 * /55098U / 1096 * / 5

Claims (2)

hoe 73/f 272hoe 73 / f 272 Patentansprüche ϊ · .Claims ϊ ·. Tl U Verfahren zur Herstellung von 3»6-Dichlor-9-xanthyliumchloriden der Formel (l)Tl U Process for the preparation of 3 »6-dichloro-9-xanthylium chlorides the formula (l) (I)(I) und 3j6-Dichlor-9-phenyl-xanthen-9-ole der Formel (il)and 3j6-dichloro-9-phenyl-xanthene-9-ols of the formula (II) in welchen R1 und R2 gleich oder verschieden sind und jedes ein Wasserstoffatom oder ein Halogenatom bedeutet, dadurch gekennzeichnet, daß man ein Benzotrichlorid der Formelin which R 1 and R 2 are identical or different and each denotes a hydrogen atom or a halogen atom, characterized in that a benzotrichloride of the formula CCl.CCl. (III)(III) 509814/1096509814/1096 in welcher R1 und R„ die obigen Bedeutungen haben, mit Resorcin in Gegenwart von überschüssigem Phosphoroxychlorid umsetzt und gegebenenfalls die erhaltenen 3i6-Dichlor-9-phenyl-xanthyliumchloride der Formel I durch Behandlung mit Alkalien in die 3f6-Dichlor-9-phenyl-xanthen-9-ole der Formel II überführt. in which R 1 and R "have the above meanings, reacts with resorcinol in the presence of excess phosphorus oxychloride and optionally converts the 3i6-dichloro-9-phenyl-xanthylium chlorides of the formula I into the 3f6-dichloro-9-phenyl- xanthene-9-ols of the formula II transferred. 2) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Umsetzung zunächst bei etwa 50 bis 60 C und dann bei
etwa 100 bis 120° C vornimmt.2) Process according to claim 1, characterized in that the reaction is first carried out at about 50 to 60 C and then at
about 100 to 120 ° C. 509814/1096509814/1096
DE19732344443 1973-09-04 1973-09-04 PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN Pending DE2344443A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DE19732344443 DE2344443A1 (en) 1973-09-04 1973-09-04 PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN
DE19742435653 DE2435653A1 (en) 1973-09-04 1974-07-25 PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS
CH1184374A CH608799A5 (en) 1973-09-04 1974-08-30 Process for the preparation of 3,6-dichloro-9-phenylxanthylium chlorides
NL7411564A NL7411564A (en) 1973-09-04 1974-08-30 PROCESS FOR PREPARING 3,6-DICHLOR-9-PHENYL-XANTHENE-9-OLEN AND 3,6-DICHLOR-9-FE-NYL-XANTHYLIUM CHLORIDES.
CH93978A CH613707A5 (en) 1973-09-04 1974-08-30 Process for the preparation of lactones of 3,6-dichloro-9-(2'-carboxyphenyl)-xanthen-9-ols
AU72894/74A AU483678B2 (en) 1973-09-04 1974-09-02 Process for preparing 3, 6-dichloro-9 phenyl-xanthene-9-ols, lactones thereof and 3, 6-dichloro-9-phenyl-xanthylium chlorides
JP9999174A JPS5082071A (en) 1973-09-04 1974-09-02
IT2685874A IT1020394B (en) 1973-09-04 1974-09-02 PROCESS FOR PREPARATION 3.6 DICHLORO 9 PHENYL XANTHEN 9 OILS AND 3.6 DICHLORINE CHLORIDES 9 PHENYL XANTYL
DK466174A DK466174A (en) 1973-09-04 1974-09-03
GB3866874A GB1432754A (en) 1973-09-04 1974-09-04 Process for preparing 3,6-dichloro-9-phenyl-xanthene-9-ols lactones thereof and 3,6-dichloro-9-phenyl-xanthylium chlorides
BE148187A BE819522A (en) 1973-09-04 1974-09-04 PROCESS FOR PREPARATION OF 3,6-DICHLORO-9-PHENYL-XANTHENE-9-OLS AND 3,6-DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES
FR7430017A FR2242390A1 (en) 1973-09-04 1974-09-04
IN1992/CAL/1974A IN142239B (en) 1973-09-04 1974-09-04

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19732344443 DE2344443A1 (en) 1973-09-04 1973-09-04 PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN
DE19742435653 DE2435653A1 (en) 1973-09-04 1974-07-25 PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS

Publications (1)

Publication Number Publication Date
DE2344443A1 true DE2344443A1 (en) 1975-04-03

Family

ID=25765733

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19732344443 Pending DE2344443A1 (en) 1973-09-04 1973-09-04 PROCESS FOR THE PREPARATION OF 3,6DICHLORO-9-PHENYL-XANTHYLIUM CHLORIDES AND 3,6-DICHLORO-9-PHENYL-XANTHEN-9-OLEN
DE19742435653 Withdrawn DE2435653A1 (en) 1973-09-04 1974-07-25 PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19742435653 Withdrawn DE2435653A1 (en) 1973-09-04 1974-07-25 PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS

Country Status (10)

Country Link
JP (1) JPS5082071A (en)
BE (1) BE819522A (en)
CH (2) CH608799A5 (en)
DE (2) DE2344443A1 (en)
DK (1) DK466174A (en)
FR (1) FR2242390A1 (en)
GB (1) GB1432754A (en)
IN (1) IN142239B (en)
IT (1) IT1020394B (en)
NL (1) NL7411564A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61137876A (en) * 1984-12-07 1986-06-25 Hodogaya Chem Co Ltd Xanthene compound, its preparation, and image-forming composition containing same

Also Published As

Publication number Publication date
FR2242390A1 (en) 1975-03-28
IN142239B (en) 1977-06-18
NL7411564A (en) 1975-03-06
DK466174A (en) 1975-05-05
IT1020394B (en) 1977-12-20
BE819522A (en) 1975-03-04
AU7289474A (en) 1976-03-04
JPS5082071A (en) 1975-07-03
DE2435653A1 (en) 1976-02-05
CH608799A5 (en) 1979-01-31
CH613707A5 (en) 1979-10-15
GB1432754A (en) 1976-04-22

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