DE2435653A1 - PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS - Google Patents

PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS

Info

Publication number
DE2435653A1
DE2435653A1 DE19742435653 DE2435653A DE2435653A1 DE 2435653 A1 DE2435653 A1 DE 2435653A1 DE 19742435653 DE19742435653 DE 19742435653 DE 2435653 A DE2435653 A DE 2435653A DE 2435653 A1 DE2435653 A1 DE 2435653A1
Authority
DE
Germany
Prior art keywords
formula
carboxyphenyl
dichloro
production
xanthen
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.)
Withdrawn
Application number
DE19742435653
Other languages
German (de)
Inventor
Rudolf Dipl Chem Dr Neeb
Theodor Dipl Chem Dr Papenfuhs
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.)
Hoechst AG
Original Assignee
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
Priority to DE19732344443 priority Critical patent/DE2344443A1/en
Application filed by Hoechst AG filed Critical Hoechst AG
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 IT2685874A priority patent/IT1020394B/en
Priority to JP9999174A priority patent/JPS5082071A/ja
Priority to AU72894/74A priority patent/AU483678B2/en
Priority to DK466174A priority patent/DK466174A/da
Priority to IN1992/CAL/1974A priority patent/IN142239B/en
Priority to FR7430017A priority patent/FR2242390A1/fr
Priority to BE148187A priority patent/BE819522A/en
Priority to GB3866874A priority patent/GB1432754A/en
Publication of DE2435653A1 publication Critical patent/DE2435653A1/en
Withdrawn legal-status Critical Current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
    • 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

Description

HOECHST AKTIENGESELLSCHAFT Aktenzeichen: HOE 74/F 214 Datum:HOECHST AKTIENGESELLSCHAFT file number: HOE 74 / F 214 Date:

23. Juli 1974July 23, 1974

Dr.ST/ζDr.ST/ζ

Verfahren zur Herstellung von 3»6-Dichlor-9-(2'-carboxyphenyl) xanthen-9-olen bzw. deren LaktonenProcess for the preparation of 3 »6-dichloro-9- (2'-carboxyphenyl) xanthene-9-ols or their lactones

Zusatz zu Patent (Patentanmeldung P 23 hk khj.1)Addendum to patent (patent application P 23 hk khj. 1)

Gegenstand des Patents . ... ... (Patentanmeldung P 23 kh ist ein Verfahren zur Herstellung von 3»6-Dichlor-9-xanthylium chloriden der Formel (l)Subject of the patent. ... ... (Patent application P 23 kh is a process for the production of 3 »6-dichloro-9-xanthylium chlorides of the formula (l)

(I)(I)

und 3,6-Dichlor-9-phenyl-xanthen-9-olen der Formel (il)and 3,6-dichloro-9-phenyl-xanthen-9-ols of the formula (il)

(H)(H)

509886/1 122509886/1 122

in welchen R1 und R0 gleich oder verschieden sind und jedes ein Wasserstoffatom oder ein Halogenatom bedeutet, dadurch gekennzeichnet, daß man ein Benzotrichlorid der Formel (ill)in which R 1 and R 0 are identical or different and each denotes a hydrogen atom or a halogen atom, characterized in that a benzotrichloride of the formula (ill)

(in)(in)

in welcher R1 und R9 die obigen Bedeutungen haben, mit Resorcin in Gegenwart von überschüssigem Phosphoroxychlorid umsetzt und gegebenenfalls die erhaltenen 3»6-Dichlor-9-phenyl-xanthyliumchloride der Formel (l) durch Behandlung mit Alkalien in die 3»6-Dichlor-9-phenyl-xanthen-9-ole der Formel (il) überführt.in which R 1 and R 9 have the above meanings, reacts with resorcinol in the presence of excess phosphorus oxychloride and optionally converts the 3 »6-dichloro-9-phenylxanthylium chlorides of the formula (l) obtained into the 3» 6- Dichloro-9-phenyl-xanthene-9-ols of the formula (II) are transferred.

In weiterer Ausgestaltung dieses Erfindungsgedankens wurde nun gefunden, daß man 3>6-Dichlor-9-(2'-carboxyphenyl)-xanthen-9-ole der Formel (iv)In a further embodiment of this inventive concept, it has now been found that 3> 6-dichloro-9- (2'-carboxyphenyl) -xanthene-9-ols of formula (iv)

(IV) COOH(IV) COOH

worin R^ und Rj gleich oder verschieden sind und jedes ein Wasserstoffatom, ein Halogenatom, insbesondere Chlor- oder Bromatome, eine Alkyl-Gruppe, vorzugsweise mit 1 bis 4 Kohlenstoff-Atomen, die Hydroxy-, Carbonsäure- oder Sulfonsäuregruppen bedeutet, bzw. deren Laktone der Formelwhere R ^ and Rj are the same or different and each is a hydrogen atom, a halogen atom, in particular chlorine or bromine atoms, an alkyl group, preferably with 1 to 4 carbon atoms, denotes the hydroxyl, carboxylic acid or sulfonic acid groups, or their lactones of the formula

509886/1122509886/1122

(ν)(ν)

erhält, wenn man in Abänderung des Verfahrens des Patentsobtained when changing the procedure of the patent

. - (Patentanmeldung P 23 hh ^3,1) ein Phthalsäureanhydrid. - (Patent application P 23 hh ^ 3.1) a phthalic anhydride

der Formel (Vl)of the formula (Vl)

(VI)(VI)

worin R„ und Rr die oben angegebene Bedeutung besitzen, mit Resorcin in Gegenwart von überschüssigem Phosphoroxychlorid umsetzt und anschließend mit Alkalien behandelt.in which R "and Rr have the meaning given above, with resorcinol reacted in the presence of excess phosphorus oxychloride and then treated with alkalis.

Das erfindungsgemäße Verfahren wird in der Weise durchgeführt, daß man eine Mischung aus 1 Mol eines Phthalsäureanhydrids der Formel (Vj), 2 Mol Resorcin und etwa 3 bis h Mol Phosphoroxychlorid etwa 15 bis 20 Stunden auf etwa 4θ bis 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, das Gemisch dann auf etwa 70 bis 80 C abkühlt, langsam bei etwa 60 C bis 100 C, vorzugsweise 70 bis 90 C, in überschüssiges Alkali, beispielsweise in wäßrige Natronlauge oder Kalilauge, einträgt, und "das abgeschiedene 3 *6-Dichlor-9-xanthen-9-ol bzw. das entsprechende Lakton anschließend isoliert.The inventive method is carried out in such a manner that a mixture of 1 mol of phthalic anhydride of the formula (Vj), 2 moles of resorcinol and about 3 to h mol of phosphorus oxychloride for about 15 to 20 hours to about 4θ to 70 C, preferably 50 to 60 C., and then for about 2 to 3 hours to about 90 to 125 ° C, preferably 100 to 120 ° C, then the mixture is cooled to about 70 to 80 C, slowly at about 60 to 100 ° C, preferably 70 to 90 C, enters in excess alkali, for example in aqueous sodium hydroxide solution or potassium hydroxide solution, and "the separated 3 * 6-dichloro-9-xanthen-9-ol or the corresponding lactone is then isolated.

Sofern die Substituenten R„ bzw.If the substituents R "or

eine Carbonsäure- oder SuI-a carboxylic acid or suI

fonsäuregruppe bedeuten, erfolgt die Abscheidung der Laktone durch, anschließende Zugabe einer anorganischen Säure, beispiels-Fonsäuregruppe mean, the lactones are deposited by, subsequent addition of an inorganic acid, for example

509886/ 1122509886/1122

weise Salzsäure oder Schwefelsäure, oder einer organischen Säure.wise hydrochloric acid or sulfuric acid, or an organic acid.

Die so erhältlichen 3,6-Dichlor-9-(2'-carboxyphenyl)-xanthen-9-ole bzw. deren Laktone sind gut filtrierbare, gegen Alkalien sehr beständige Verbindungen, die bevorzugt für die Herstellung von Xanthenfarbstoffen verwendet werden (vgl. Bios 959 und Ullmanns Encyklopädie der technischen Chemie, 3· Auflage, Band 18 (1967), Seite 716).The 3, 6-dichloro-9- (2'-carboxyphenyl) -xanthene-9-ols or their lactones are easily filterable, very alkaline-resistant compounds that are preferably used for the production of xanthene dyes (cf. Bios 959 and Ullmanns Encyklopadie der technischen Chemie, 3rd edition, Volume 18 (1967), page 716).

Gegenüber den bekannten Verfahren zur Herstellung der 3,6-Dichlor-9-(2'-carboxyphenyl)-xanthen-9-ole bzw. deren Laktone, die zweistufige Verfahren darstellen, bei denen zunächst Phthalsäureanhydrid mit Resorcin zum Fluoreszein verschmolzen (vgl. Ullmanns Encyklopädie der technischen Chemie, 3· Auflage, Band 18 (I967)» Seite 712 bis 513) und dieses nach Isolierung durch Behandlung mit Phosphoroxychlorid in einem organischen Lösungsmittel, beispielsweise o-Dichlorbenzol, in das 3»6-Dichlor~9-(2'-carboxyphenyl )-xanthen-9-ol bzw. dessen Lakton überführt wird (vgl. Bios 986, I, 156)f besitzt das erfindungsgemäße Verfahren den Vorteil, daß es wesentlich einfacher ohne Isolierung von Zwischenstufen und in Abwesenheit von organischen Lösungsmitteln durchgeführt werden kann.Compared to the known processes for the production of 3,6-dichloro-9- (2'-carboxyphenyl) -xanthene-9-ols or their lactones, which represent two-stage processes in which phthalic anhydride is fused with resorcinol to form fluorescein (cf. Ullmanns Encyklopadie der technischen Chemie, 3rd edition, Volume 18 (1967) »pages 712 to 513) and this after isolation by treatment with phosphorus oxychloride in an organic solvent, for example o-dichlorobenzene, into the 3» 6-dichloro ~ 9- (2nd '-carboxyphenyl) -xanthene-9-ol or its lactone is converted (cf. Bios 986, I, 156) f the process according to the invention has the advantage that it can be carried out much more easily without isolating intermediate stages and in the absence of organic solvents can.

Das nachstehende Beispiel dient zu seiner Erläuterung.The following example serves to explain it.

509886/ 1 1 22509886/1 1 22

Beispiel: Example :

In eine Mischung aus 110 Gewichlsteil en Resorcin und 251 Gewichtstoilon Phosphoroxychlorid trägt man bei 50 bis 55 C innerhalb von einer Stunde 74 Gewichtsteile Phthalsäureanhydrid ein. Dann rührt man etwa 16 Stunden bei 50 bis 55 C, erwärmt dann in einer Stunde auf 110 C und hält 2 Stunden bei dieser Temperatur. Anschließend tropft man die auf 80 C abgekühlte Reaktionsmischung zu einer 70 bis 75 C warmen Mischung aus 2000 Volumenteilen "Wasser und 600 Gewichtsteilen 33 /tiger 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 127 Gewichtsteile (= 76.4 °ß> der Theorie) 3,6-Dichlor-9-(2 '-carboxyphenyl )-xanthen-9-ol in Form dcjs Laittons . ( 3> 6-Dichlorfluoran) vom Schmelzpunkt 248 bis 251°C.74 parts by weight of phthalic anhydride are introduced into a mixture of 110 parts by weight of resorcinol and 251 parts by weight of phosphorus oxychloride at 50 to 55 ° C. within one hour. The mixture is then stirred for about 16 hours at 50 to 55 ° C., then heated to 110 ° C. in one hour and kept at this temperature for 2 hours. The reaction mixture, cooled to 80 ° C., is then added dropwise to a 70 to 75 ° C. mixture of 2000 parts by volume of water and 600 parts by weight of 33% sodium hydroxide solution, the rate of dropping being chosen so that the initial charge boils gently under reflux. The mixture is then stirred without heating for 15 minutes, during which the mixture cools to about 80 ° C., the precipitate is filtered off with suction, washed three times with 250 parts by volume of hot water, sucked dry and dried at 60 ° C. 127 parts by weight (= 76.4 ° ß > of theory) 3,6-dichloro-9- (2'-carboxyphenyl) -xanthene-9-ol in the form of Laittons. (3> 6-dichlorofluorane) with a melting point of 248 to 251 ° C.

In ähnlicher Weise lassen sich die nachstehenden Verbindungen der Formel (v) herstellen:The following compounds of the formula (v) can be prepared in a similar manner:

Beispielexample E3 E 3 4-Cl4-Cl R4 R 4 Alis beut GAli's booty G 22 3- bzw.3- or 4-Cl4-Cl HH 52 io 52 io 33 3- bzw.3- or HH 63 io 63 io 44th 3-ci3-ci 6-Cl6-Cl 51 io 51 io 55 4-OH4-OH 5-COOH5-COOH 72 io 72 io 66th 4-COOH4-COOH HH 78 io 78 io 77th 4-S0„H4-S0 "H HH iy t~r öliy t ~ r oil
I I /οI I / ο 88th --*
4-Br- *
4-Br ■ H■ H 68 io 68 io

509886/ 1 122509886/1 122

Claims (2)

2 43S653 HOE 74/F 214 Patentansprüche2 43S653 HOE 74 / F 214 claims 1. Verfahren zur Herstellung von 3 j 6--Dichlor-9- (2 ' - carboxyphenyl)~xanthen-9~olen der Formel1. Process for the preparation of 3 ~ 6-dichloro-9- (2 '- carboxyphenyl) ~ xanthene-9 ~ ols the formula worin. R„ und R^ Wasserstoff, Halogen a tome, Alkyl-, Alkoxy-, Hydroxy-, Carbonsäure- oder SuIfonstmregruppen bedeuten, bzw. deren Laktone der Formelwherein. R "and R ^ is hydrogen, halogen a tome, are alkyl, alkoxy, hydroxy, carboxylic acid or SuIfonstmregruppen, or their lactones of the formula dadurch gekennzeichnet, daß man in Abänderung des Verfahrenscharacterized in that one in modification of the procedure des Patents (Patentanmeldung P 23 44 443.1) einof the patent (patent application P 23 44 443.1) Phthalsäureanhydrid der FormelPhthalic anhydride of the formula 5 0 9886/11225 0 9886/1122 - 7 - HOE 74/F 214- 7 - HOE 74 / F 214 worin R„ und R. die oben angegebene Bedeutung besitzen, mit Resorcin in Gegenwart von überschüssigem Phosplioroxychlorid umsetzt und anschließend mit Alkalien behandelt.wherein R "and R. have the meaning given above, with Reacts resorcinol in the presence of excess phosphorus oxychloride and then treated with alkalis. 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. The method according to claim 1, characterized in that one the reaction initially at about 50 to 60 C and then at about 100 to 120 C. 509886/ 1 122509886/1 122
DE19742435653 1973-09-04 1974-07-25 PROCESS FOR THE PRODUCTION OF 3,6DICHLORO-9- (2'CARBOXYPHENYL) -XANTHEN-9OLEN OR THEIR LACTONS Withdrawn DE2435653A1 (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
IN1992/CAL/1974A IN142239B (en) 1973-09-04 1974-09-04
FR7430017A FR2242390A1 (en) 1973-09-04 1974-09-04
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
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

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
DE2435653A1 true DE2435653A1 (en) 1976-02-05

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 Before (1)

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

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
CH613707A5 (en) 1979-10-15
NL7411564A (en) 1975-03-06
DE2344443A1 (en) 1975-04-03
BE819522A (en) 1975-03-04
JPS5082071A (en) 1975-07-03
AU7289474A (en) 1976-03-04
DK466174A (en) 1975-05-05
CH608799A5 (en) 1979-01-31
FR2242390A1 (en) 1975-03-28
IT1020394B (en) 1977-12-20
GB1432754A (en) 1976-04-22
IN142239B (en) 1977-06-18

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