DE2154659A1 - Color formers - Google Patents
Color formersInfo
- Publication number
- DE2154659A1 DE2154659A1 DE19712154659 DE2154659A DE2154659A1 DE 2154659 A1 DE2154659 A1 DE 2154659A1 DE 19712154659 DE19712154659 DE 19712154659 DE 2154659 A DE2154659 A DE 2154659A DE 2154659 A1 DE2154659 A1 DE 2154659A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- radical
- color formers
- atom
- 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
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
-
- 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
- C09B17/00—Azine dyes
-
- 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
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
PATENTANWÄLTE DR.-ING. H. FINCKE DIPL.-ING. H. BOHR DIPL.-ING. S. STAEGER PATENT LAWYERS DR.-ING. H. FINCKE DIPL.-ING. H. BOHR DIPL.-ING. S. STAEGER
Farn ru fi »24 60 60Fern ru fi »24 60 60
Ifeippe 22720 - Dr. E= Case Ds 23249Ifeippe 22720 - Dr. E = Case Ds 23249
β MÜNCHEN O1 MOlhntrafi· 31β MUNICH O 1 MOlhntrafi 31
3 NOV. 1971 2154659 3 NOV. 1971 2154659
Imperial Chemical Industries Ltd. London, GroßbritannienImperial Chemical Industries Ltd. London, UK
FarbbildnerColor formers
Prioritäten: 4·. 11. 1970 und 20. 10. 1971 - GroßbritannienPriorities: 4 ·. 11th 1970 and 20th 10th 1971 - Great Britain
Die Erfindung bezieht sich auf Farbbildner und insbesondere auf farblose Farbbildner, die sich für die Verwendung in Kopi wewat&m&fi Mit sauberer Handhabung eignen«The invention relates to color formers and more particularly to colorless color formers suitable for use in Kopi wewat & m & fi with clean handling «
ba:? sba :? s
järfiäduag werden farblose Farbbildner wrg;e schlagen, es sich um Verbindungen der allgemeinen iormeljärfiäduag colorless color formers wrg; e beat, these are compounds of the general iormula
CO-Q-VCO-Q-V
\ E \ E
209820/1156 BAD ORIGINAL209820/1156 ORIGINAL BATHROOM
handelt, worin X für ein Wasserstoff atom, eine Bydroxygruppeis where X is a hydrogen atom, a hydroxy group
P -JL P -JL
oder eine Gruppe der Formel -NR Ir steht, D für ein Saueretoffatom, ein Schwefelatom oder eine Gruppe der Formel -NR- steht, Q für ein Sauerstoffatom oder eine Gruppe der Formel -NH-steht, Y für ein Alkylradikal, Arylradikal oder Aralkylradikal steht, jedes der Symbole R3 R , R , R* und R unabhängig für ein Wasserstoffatom oder ein gegebenenfalls substituiertes Kohlenwasserstoff radikal steht, und die Ringe A und B gegebenenfalls weitere Substituenten tragen können«or a group of the formula -NR Ir, D is an oxygen atom, a sulfur atom or a group of the formula -NR-, Q is an oxygen atom or a group of the formula -NH-, Y is an alkyl radical, aryl radical or aralkyl radical , each of the symbols R 3 R, R, R * and R independently represents a hydrogen atom or an optionally substituted hydrocarbon radical, and the rings A and B can optionally carry further substituents «
Kohlenwasserstoff radikale, die durch R, R , R , R^ und R dargestellt werden können, sind insbesondere niedrige Alky!radikale mit 1 bis 4 Kohlenstoffatomen« ganz besonders das Methyl- und Äthylradikal, und Aryiradikale, wie z.B. das Phenylradikal. Radikale, die durch V dargestellt werden können, sind z.B. Alkylradikale, Rienylradikale und Benzylradikale.Hydrocarbon radicals represented by R, R, R, R ^ and R are, in particular, lower alkyl radicals with 1 to 4 carbon atoms «especially the methyl and Ethyl radical, and aryi radicals such as the phenyl radical. Radicals which can be represented by V include, for example, alkyl radicals, rienyl radicals and benzyl radicals.
ule erfindungsgemäßen Farbbildner können dadurch hergestellt werden, daß man einen Farbstoff der Azin-, Oxazin- oder Thiazinreihe zur entsprechenden Leucoverbindung der Formel ule color formers according to the invention can be prepared by adding a dye of the azine, oxazine or thiazine series to the corresponding leuco compound of the formula
reduziert und hierauf die Leucoverbindung mit einem geeigneten Mittel umsetzt, um ein Radikal der Formelreduced and then reacting the leuco compound with a suitable agent to a radical of the formula
- CO - Q - V - CO - Q - V
einzuführen. Geeignete MIttel sind Alkyl-, Aralkyl- und Arylahloroformiata undto introduce. Suitable agents are alkyl, aralkyl and aryl chloroformates and
209820/1156209820/1156
Die erfindungsgemäßen Farbbildner eignen sich besonders .für die Verwendung in Kopiersystemen mit sauberer Handhabung* wie s.B. in Vervielfältigungssystemen« Bei solchen Systemen wird ein Blatt, dae den farblosen Farbbildner trägt,, welcher in einer geeigneten hochsiedenden Flüssigkeit gelöst ist, durch Beschreiben einem Druck ausgesetzt und dabei mit einem-Kopierpapier in Kontakt gebracht * das eine Oberfläche mit einem aktiven Mineral aufweist« wie z.B. Siliciumdioxid oder Attapulgit. Durch Hydrolyse des Farbbildners und Oxidation der so gebildeten Leucoverbindung zum Ausgaagsfarbstoff wird ein farbiges Bild der ursprünglichen Schrift erzeugt. Gegenüber den bereits für diesen Zweck verwendeten Farbbildnern, wie z.B.The color formers according to the invention are particularly suitable the use in copier systems with clean handling * like s.B. in replication systems «In such systems becomes a sheet that bears the colorless color former, which is dissolved in a suitable high-boiling liquid, subjected to pressure by writing and thereby with a copy paper brought into contact * the one surface with an active mineral «such as silicon dioxide or attapulgite. Through hydrolysis of the color former and oxidation the leuco compound thus formed becomes the output dye creates a colored image of the original font. Opposite to the color formers already used for this purpose, e.g.
Eristallviolettlacton und Benzoylleucoiaethylenblautbesitzen sie hineichtlich des Farbtons und der Echtheit Vorteile«. Gegenüber den üblicheren acylierten Leucofarbstoffen besitzen sie insofernEristallviolettlacton and Benzoylleucoiaethylenblau t they have hineichtlich of hue and fastness benefits. " Compared to the more common acylated leuco dyes, they have insofar
Vorteile, als das farbige Bild rascher gebildet wird*Advantages as the colored image is formed faster *
Die Erfindung wird durch die folgenden Beispiele näher erläutert, in denen alle Teile und Pro ζ ent angab en in Gewicht auegedrückt sind οThe invention is illustrated in more detail by the following examples, in which all parts and pro ζ ces are given in weight are ο
7,6 Teile Methylenblau in Form des Zinkchloriddoppelsalzes werden in einer Mischung aus 50 Teilen Wasser und 90 Teilen Monochlorbenzol aufgelöst und durch B€5handlung mit 9»2 Teilen Natriuradithionit in die entsprechende Leucoverbindung reduziert. Die Ifonochlorobenzolschiclit, welche die Leucoverbindung enthält s wird von der wässrigen Phase abgetrennt, über wasserfreiem Magnesiumsulfat getrocknet vmä mit einem Geminch aus 5 Teilen Pyridin und 4^5 Teilen Äthylehloroformiat behandelt. Nachdem das Reaktionsgemisch 2 st bei Raumtemperatur fätehen gelassen ist« wird das Lösungsmittel durch Destillation entfernt.;7.6 parts of methylene blue in the form of the zinc chloride double salt are dissolved in a mixture of 50 parts of water and 90 parts of monochlorobenzene and reduced to the corresponding leuco compound by treatment with 9/2 parts of sodium radithionite. The Ifonochlorobenzolschiclit, which contains the leuco compound s is separated from the aqueous phase, dried over anhydrous magnesium sulfate and treated with a Geminch of 5 parts of pyridine and 4 ^ 5 parts of ethyl chloroformate. After the reaction mixture has left to stand for 2 hours at room temperature, the solvent is removed by distillation.
209820/1156209820/1156
und der Rückstand wird aus Acetonitril kristallisiert. Das Produkt, IO-Äthoxycarbonyl-3»7-ois(dimethylamine)phenothiazin, wird in Form farbloser Kristalle mit einem Schmelzpunkt von 153°C erhalten.and the residue is crystallized from acetonitrile. That Product, IO-ethoxycarbonyl-3 »7-ois (dimethylamine) phenothiazine, comes in the form of colorless crystals with a melting point of 153 ° C obtained.
Wenn das Produkt als Lösung in einem geeigneten hochsiedenden organischen Lösungsmittel mit einer ein aktives Mineral aufweisenden Oberfläche in Berührung gebracht wird, wie z.B. Siliciumdioxid oder Attapulgitton, wie sie beisielsweise als Aufnahmeoberflächen in sogenannten kohlefreien Kopierpapieren verwendet werden, dann wird rasch ein farbiges Methylenblaubild erhalten.If the product as a solution in a suitable high-boiling point organic solvent is brought into contact with a surface having an active mineral, e.g. Silicon dioxide or attapulgite clay, such as those used as receiving surfaces in so-called carbon-free copier papers are used, a colored methylene blue image is quickly obtained.
Anstelle des Pyridine und des Äthylchloroformiats$ welche in Beispiel 1 verwendet worden sind, werden 4*8 Teile Phenylisocyanat verwendet. Das erhaltene Produkt, nämlich 10-Phenylcarbaaoyl-3»7-bi8(dimethylamino)phenothiazin, besitzt einen Schmelzpunkt von 1600G und kann in ähnlicher Weise zur Herstellung eines farbigen Bilds verwendet werden, wenn es mit einer ein aktives Mineral aufweisenden Oberfläche in Berührung gebracht wird.Have been used instead of the pyridines and $ Äthylchloroformiats that in Example 1 are used 4 * 8 parts of phenyl isocyanate. The obtained product, namely 10-Phenylcarbaaoyl-3 »7-BI8 (dimethylamino) phenothiazine has a melting point of 160 0 G, and can be similarly used for preparing a color image, if fitted with an active mineral-containing surface in contact is brought.
209820/1156209820/1156
Die Farbbildner dor Spalte C der folgenden Tabelle können durch das Verfahren des Beispiels üergesteilt werden, wenn man die Leucoform des Farbstoffs dex* Spalte A mit dem mittel der Spalte B umsetzt.The color formers in column C of the following table can be prepared by the method of the example if you compare the leuco form of the dye dex * column A with the by means of column B.
S. 3,7-Bis(diäthylamino)
phenoxazonium-chlorid
7. 3-Diäthylamino-7-di (ß-cyanoäthyl)
amino-phenoxazoni lm-chlorid
8. 3-jDimethylamino-7-hydroxy-
phenoxazonium-chlorid
9♦ 3,7-Bis(dimethylamino)-6-nitro-
phenothiazonium-chlorid
(CI Basic Green 5)
10.3 s7-Bis-(diäthylamino)-5-phenyl-
ph€lazonium-chiorid
(Heliotrope B)3. methylene blue
P. 3,7-bis (diethylamino)
phenoxazonium chloride
7. 3-Diethylamino-7-di (ß-cyanoethyl)
amino-phenoxazoni lm-chloride
8. 3-dimethylamino-7-hydroxy
phenoxazonium chloride
9 ♦ 3,7-bis (dimethylamino) -6-nitro-
phenothiazonium chloride
(CI Basic Green 5)
10.3 s7-bis (diethylamino) -5-phenyl-
ph € lazonium chiorid
(Heliotrope B)
Phenyl-chloroformiat
Benzyl-chloroformiat
Ithyl-chloroformiat
ithyl-chloroformiat
ithyl-chloroformiat
ithyl-chloroformiat
ithyl-chloroformiatn-butyl chloroformate
Phenyl chloroformate
Benzyl chloroformate
Ethyl chloroformate
ethyl chloroformate
ethyl chloroformate
ethyl chloroformate
ethyl chloroformate
(dimethylamino )phenothia zin
10-(Phenoxycarbnnyl)-3,7-bis ι
(dimethylamino )phenothiazin (
10-(Benzyloxycarbonyl)-3,7- |
bis(dimethylamino)phenothiazir.
IO-ithoxycarbonyl-3,7-bis
(diäthylamino )phenoxazin
10-ithoxycarbonyl-3-diäthyl~
amino-7-di(ß-cyanoäthyl)amiuo |
phenoxazin
10-ithoxycarbonyl-3-dimethyl-
amino-7-hydroxyphenoxazin
IO-ithoxycarbonyl-3 *7-bis
(dimethylamino ) -6-nitropheno-
thiazin
IO-ithoxycarbonyl-3 (j7-bis-
(diäthylamino)-5-phenyl-
phenazin10- (butoxycarbonyl) -3> 7-bis
(dimethylamino) phenothia zin
10- (Phenoxycarbnnyl) -3,7-bis ι
(dimethylamino) phenothiazine (
10- (benzyloxycarbonyl) -3.7- |
bis (dimethylamino) phenothiazir.
IO-ithoxycarbonyl-3,7-bis
(diethylamino) phenoxazine
10-ithoxycarbonyl-3-diethyl ~
amino-7-di (ß-cyanoethyl) amiuo |
phenoxazine
10-ithoxycarbonyl-3-dimethyl-
amino-7-hydroxyphenoxazine
IO-ithoxycarbonyl-3 * 7-bis
(dimethylamino) -6-nitropheno-
thiazine
IO-ithoxycarbonyl-3 (j 7-bis-
(diethylamino) -5-phenyl-
phenazine
Anstelle des Pyridine und dem Ithyl-shloroforsiiats voii ".eispiel 1 werden 2Γ9 Teile Ithj-Llsocyanat verwendet. Das gehaltene Produkt ist 10~Äthylcai'bamoyl-3,7-l3is(dimethylamino)-ph^nothiazin. Instead of the pyridines and the Ithyl-shloroforsiiats voii ".eispiel 1 2 Γ 9 parts Ithj-Llsocyanat be used. The product is held 10 ~ Äthylcai'bamoyl-3,7-l3is (dimethylamino) -ph ^ phenothiazine.
209820/1156209820/1156
BAD Ä 'BATHROOM Ä '
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5244870 | 1970-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2154659A1 true DE2154659A1 (en) | 1972-05-10 |
Family
ID=10463962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712154659 Pending DE2154659A1 (en) | 1970-11-04 | 1971-11-03 | Color formers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2154659A1 (en) |
| FR (1) | FR2113509A5 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124296A1 (en) * | 1983-04-05 | 1984-11-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| US4563415A (en) * | 1983-04-05 | 1986-01-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| EP0181085A1 (en) * | 1984-10-01 | 1986-05-14 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US4889932A (en) * | 1984-10-01 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| EP0671393A1 (en) * | 1994-03-11 | 1995-09-13 | Minnesota Mining And Manufacturing Company | Monoaminophenazine leuco dyes and photothermographic materials containing same |
-
1971
- 1971-11-03 DE DE19712154659 patent/DE2154659A1/en active Pending
- 1971-11-03 FR FR7139350A patent/FR2113509A5/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124296A1 (en) * | 1983-04-05 | 1984-11-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| US4563415A (en) * | 1983-04-05 | 1986-01-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| EP0181085A1 (en) * | 1984-10-01 | 1986-05-14 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US4647525A (en) * | 1984-10-01 | 1987-03-03 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| WO1987002048A1 (en) * | 1984-10-01 | 1987-04-09 | Minnesota Mining And Manufacturing Company | Novel phenazine dyes |
| US4889932A (en) * | 1984-10-01 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US5428161A (en) * | 1984-10-01 | 1995-06-27 | Minnesota Mining And Manufacturing Company | Phenazine dyes |
| EP0671393A1 (en) * | 1994-03-11 | 1995-09-13 | Minnesota Mining And Manufacturing Company | Monoaminophenazine leuco dyes and photothermographic materials containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2113509A5 (en) | 1972-06-23 |
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