DE1038916B - Process for producing color photographic images - Google Patents
Process for producing color photographic imagesInfo
- Publication number
- DE1038916B DE1038916B DEG22339A DEG0022339A DE1038916B DE 1038916 B DE1038916 B DE 1038916B DE G22339 A DEG22339 A DE G22339A DE G0022339 A DEG0022339 A DE G0022339A DE 1038916 B DE1038916 B DE 1038916B
- Authority
- DE
- Germany
- Prior art keywords
- dye
- color photographic
- photographic images
- producing color
- former
- 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
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/362—Benzoyl-acetanilide couplers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Nach der von Fischer gefundenen Farbentwicklung kann man Farbbilder durch Entwicklung eines reduzierbaren Silbersalzbildes mit einer primären aromatischen Aminoentwicklersubstanz in Anwesenheit einer solchen Verbindung erzeugen, die eine reaktionsfähige Methylengruppe, wie beispielsweise ein /?-Diketon, enthält.According to the color development found by Fischer one can obtain color images by developing a reducible silver salt image with a primary generate aromatic amino developing agent in the presence of such a compound that a reactive methylene group, such as a /? - diketone contains.
Später wurde bekannt, Farbstoffbildner des Typus CH3COCH2CONHZ zu verwenden, worin Z einen heterocyclischen Ring bedeutet. Wegen der sehr geringen Farbdichte der entwickelten Bilder sind diese Farbstoffbildner praktisch nur wenig geeignet. Die Ersetzung der CH3-Gruppe durch eine höhere Alkylgruppe zum Diffusionsfestmachen des Farbstoffbildners kann diesen Nachteil nicht aufheben.It later became known to use dye formers of the type CH 3 COCH 2 CONHZ, in which Z denotes a heterocyclic ring. Because of the very low color density of the developed images, these dye formers are not very suitable in practice. The replacement of the CH 3 group by a higher alkyl group to make the dye former resistant to diffusion cannot eliminate this disadvantage.
Ferner ist bekannt, daß Farbstoffe mit guten Eigenschaften erzielt werden, wenn als Farbstoffbildner, welche eine reaktionsfähige Methylengruppe enthalten. Derivate von Benzoylaceton oder Benzoylacetanilid verwendet werden.It is also known that dyes with good properties are obtained if, as dye formers, which contain a reactive methylene group. Derivatives of benzoylacetone or benzoylacetanilide be used.
Es ist weiter bekannt, daß die Absorption der aus Acylacetaniliden erhaltenen Farbstoffe durch eine Alkoxysubstitution in die Acylgruppe und somit die Verwendung dieser Acylaeetanilide als hypsochrome Farbstoffbildner in negativem photographischem Material vorteilhaft beeinflußt wird.It is also known that the absorption of the dyes obtained from acylacetanilides by a Alkoxy substitution in the acyl group and thus the use of these Acylaeetanilide as hypsochromic Dye formers in negative photographic material is beneficially influenced.
Aus der deutschen Patentschrift 1 000 233 sind nur im Arylidteil alkoxylierte, eine Acylamidogruppe enthaltende Benzoylacetanilidfarbstoffbildner bekannt, welche durch Farbentwicklung Farbstoffe erzeugen, deren geradliniger Teil der Absorptionskurve scharf gezeichnet ist, deren Absorptionsmaximum aber zu hypsochrom ist, so daß diese Farbstoffbildner sich beispielsweise nicht zur Herstellung eines Positivmaterials verwenden lassen, weil hier ein bathochromes Absorptionsmaximum zu fordern ist.From the German patent specification 1 000 233 there is only one acylamido group which is alkoxylated in the arylide part containing benzoylacetanilide dye formers known which produce dyes through color development, whose straight-line part of the absorption curve is drawn sharply, but whose absorption maximum closes is hypsochromic, so that these dye formers cannot be used, for example, to produce a positive material can be used because here a bathochromic absorption maximum is required.
Weiter sind aus der USA.-Patentschrift 2 395 776 Farbstoffbildner bekannt, welche die GruppierungUS Pat. No. 2,395,776 also discloses dye formers which form the group
>— CO — CH8 — CO — NH — Heterorest> - CO - CH 8 - CO - NH - hetero radical
enthalten. Die Farbdichte, die mittels der in dieser USA.-Patentschrift beschriebenen Farbstoffbildner durch Farbentwicklung erzeugt wird, ist aber äußerst schwach.contain. The color density obtained by means of the dye formers described in this USA patent generated by color development, but it is extremely weak.
Es wurde nun gefunden, daß durch Entwicklung eines reduzierbaren Silbersalzbildes mittels einer primären aminoaromatischen Entwicklersubstanz in Anwesenheit eines Benzoylacetamides nach der FormelIt has now been found that by developing a reducible silver salt image by means of a primary aminoaromatic developer in the presence of a Benzoylacetamides after formula
R — 0— <R - 0 - <
CO-CH2-CO-NH-YCO-CH 2 -CO-NH-Y
in der R eine diffusionsfestmachende Alkylgruppe Verfahren zur Herstellung
photographischer Farbbilderin which R is a diffusion-proofing alkyl group. Process for the preparation
photographic color images
Anmelder:Applicant:
Gevaert Photo-Producten N. V.,
Mortsel, Antwerpen (Belgien)Gevaert Photo-Products NV,
Mortsel, Antwerp (Belgium)
Vertreter: Dr. W. Müller-Bore, Patentanwalt,
Braunschweig, Am Bürgerpark 8Representative: Dr. W. Müller-Bore, patent attorney,
Braunschweig, Am Bürgerpark 8
Jan Jaeken, Hove, Antwerpen (Belgien),
ist als Erfinder genannt wordenJan Jaeken, Hove, Antwerp (Belgium),
has been named as the inventor
und Y einen Heterorest bedeutet, sehr intensive und bathochrome Farbstoffe mit einem hervorragenden Absorptionsbereich erzeugt werden. Diese Farbstoffbildner unterscheiden sich im wesentlichen von den bekannten in Rede stehenden Farbstoffbildnern durch die ausgezeichnet wertvollen Effekte, welche durch ihre Verwendung, insbesondere beim Aufbauen eines Positivmaterials, erreicht werden.and Y denotes a hetero radical, very intense and bathochromic dyes with an excellent one Absorption area are generated. These dye formers differ essentially from the known in question dye formers by the excellent valuable effects, which by their use, especially when building a positive material, can be achieved.
Die Herstellung dieser Farbstoffbildner und der erforderlichen Zwischenprodukte erfolgt in leichter Weise nach den üblichen chemischen Synthesemethoden. The preparation of these dye formers and the necessary intermediates is easier Way according to the usual chemical synthesis methods.
Die Anwesenheit von Farbstoffbildnern nach der vorliegenden Erfindung während des Farbentwicklungsprozesses kann dadurch herbeigeführt werden, daß man in das photographische Material eine Verbindung einführt, die sich von dem Farbstoffbildner nur dadurch unterscheidet, daß ein Wasserstoffatom der reaktionsfähigen Methylengruppe durch eine Gruppe substituiert ist, die sich entweder vor dem Einsetzen der Farbentwicklung durch die Wirkung des in der Entwicklerlösung anwesenden Alkalis oder während der Farbentwicklung abspaltet.The presence of dye formers according to the present invention during the color development process can be brought about by making a compound in the photographic material introduces, which differs from the dye former only in that a hydrogen atom the reactive methylene group is substituted by a group that is either in front of the Onset of color development due to the action of the alkali present in the developer solution or splits off during color development.
Die neuen Farbstoffbildner können einer Kolloidschicht zugesetzt werden, sei es einer lichtempfindlichen Silberhalogenidemulsionsschicht oder einer benachbarten unempfindlichen Schicht bzw. einer unempfindlichen Schicht, die mittels einer wasserdurchlässigen Kolloidschicht vor der lichtempfindliehen Schicht getrennt ist.The new dye formers can be added to a colloid layer, be it a light-sensitive one Silver halide emulsion layer or an adjacent insensitive layer or a insensitive layer, which by means of a water-permeable colloid layer in front of the light-sensitive Layer is separated.
Die aromatischen Aminoverbindungen, die erfindungsgemäß als Entwicklersubstanz verwendet werden können, umfassen die Mono-, Di- und Tri-aminoarylverbindungen, insbesondere Ν,Ν-Di-The aromatic amino compounds used according to the invention as a developer substance can be, include the mono-, di- and tri-aminoaryl compounds, in particular Ν, Ν-di-
809 637/426809 637/426
alkyl-p-phenylendiamine und deren Derivate, wie Ν,Ν-Dialkyl-N'-sulfomethyl- oder -carboxymethylp-phenylendiamine. Als Monoaminoentwickler kommen Aminophenole und Aminokresole bzw. deren Halogenderivate sowie auch Aminonaphthole in Betracht.alkyl-p-phenylenediamines and their derivatives, such as Ν, Ν-dialkyl-N'-sulfomethyl- or -carboxymethylp-phenylenediamines. Aminophenols and aminocresols or their halogen derivatives as well as aminonaphthols can be used as monoamino developers Consideration.
Die folgenden Beispiele dienen der Erläuterung des beschriebenen Verfahrens* ohne es in irgendeiner Weise zu beschränken.The following examples serve to illustrate the process described * without it in any way Way to restrict.
32,3 g 4-{beta-[4-(l,l,3,3-Tetramethylbutyl)-phenoxy] - äthoxy} - benzoylessigsäuremethylester (hergestellt nach der deutschen Patentanmeldung G 15463) und 18,3 g 2-Amino-4,5-dicarbäthoxythiazol (hergestellt nach L. Conover, J. Am. Chem. Soc, 72 [1950], S. 5221 bis 5225) werden in 800 cm3 Xylol 3 Stunden am Rückflußkühler gekocht. Das gebildete Methanol wird mit 1 Teil des Xylols abdestilliert, wobei das Niveau des Reaktionsvolumens durch Zusatz von frischem Xylol auf gleicher Höhe gehalten wird.32.3 g of 4- {beta- [4- (l, l, 3,3-tetramethylbutyl) -phenoxy] -ethoxy} -benzoyl acetic acid methyl ester (prepared according to German patent application G 15463) and 18.3 g of 2-amino-4 , 5-dicarbäthoxythiazol (prepared according to L. Conover, J. Am. Chem. Soc, 72 [1950], pp. 5221 to 5225) are refluxed in 800 cm 3 of xylene for 3 hours. The methanol formed is distilled off with 1 part of the xylene, the level of the reaction volume being kept at the same level by adding fresh xylene.
Beim Abkühlen kristallisiert das Amid aus. Nach Umkristallisieren aus n-Butanol erhält man ein Produkt mit einem Schmelzpunkt von 181° C, das die folgende Struktur besitzt:The amide crystallizes out on cooling. After recrystallization from n-butanol, a Product with a melting point of 181 ° C, which has the following structure:
CH3 CH3 CH 3 CH 3
H3C-C-CH2-C-/H 3 CC-CH 2 -C- /
CH3 CH3 CH 3 CH 3
-0-CH2-CH2-O^ ^CO-CH2-CO-NH-C-0-CH 2 -CH 2 -O ^ ^ CO-CH 2 -CO-NH-C
S-C-COOC9H,SC-COOC 9 H,
N-C-COOC2H5 NC-COOC 2 H 5
Eine Lösung von 4 g dieses Farbstoffbildners wird zu 1 kg einer photographischen Silberhalogenidemulsion zugesetzt. Nach dem Vergießen dieser Emulsion auf einen Schichtträger und Belichten und Entwickeln erhält man ein gelbes Bild mit einem Absorptionsmaximum bei 460 πιμ.A solution of 4 g of this dye-former becomes 1 kg of a silver halide photographic emulsion added. After casting this emulsion on a layer support and exposure and Developing gives a yellow image with an absorption maximum at 460 πιμ.
Wenn im Beispiel 1 das 2-Amino-4,5-dicarbäthoxythiazol durch ein Produkt folgender FormelIf in Example 1 the 2-amino-4,5-dicarbäthoxythiazol by a product of the following formula
C-COOCH,C-COOCH,
-CH9-COOCH,-CH 9 -COOCH,
—C—C
N — C — CH,N - C - CH,
(hergestellt nach Conrad, Ann., 285 [1895], S. 208) und das zum Umkristallisieren verwendete n-Butanol durch Acetonitril ersetzt werden, erhält man einen Farb.stoffbildner, der bei 178° C schmilzt und nach Farbentwicklung ein gelbes Bild mit einem Absorptionsmaximum bei 450 πιμ ergibt.(prepared according to Conrad, Ann., 285 [1895], p. 208) and the n-butanol used for recrystallization are replaced by acetonitrile, one obtains a Farb.stoffbildner which melts at 178 ° C and after Color development gives a yellow image with an absorption maximum at 450 πιμ.
Wenn im Beispiel 1 das 2-Amino-4,5-dicarbäthoxythiazol durch ein Produkt folgender FormelIf in Example 1 the 2-amino-4,5-dicarbäthoxythiazol by a product of the following formula
H2N-C"H 2 NC "
S-C-COOC2H5 SC-COOC 2 H 5
• I• I
. ι. ι
N-^C-CH3 N- ^ C-CH 3
(hergestellt nach Dodsori., J. Am. Chem. Soc., 67 [1945], S. 2242) und das zur Umkristallisierung verwendete n-Butanol durch Äthanol ersetzt werden, erhält man einen Farbstoffbildner, der bei 181° C schmilzt und nach Farbentwicklung ein gelbes Bild mit einem Absorptionsmaximum bei 460 τημ ergibt.(prepared according to Dodsori., J. Am. Chem. Soc., 67 [1945], p. 2242) and the n-butanol used for recrystallization is replaced by ethanol, a dye former is obtained which melts at 181 ° C. and after color development a yellow image with an absorption maximum at 460 τημ results.
Wenn im Beispiel 1 das 2-Amino-4,5-dicarbäthoxythiazol durch ein Produkt folgender FormelIf in Example 1 the 2-amino-4,5-dicarbäthoxythiazol by a product of the following formula
N-CHN-CH
(hergestellt nach Erlenmeyer, HeIv. Chim. Acta, 27 [1944], S. 1432, oder Dann, Ber., 76 [1943], S. 419) und das zur Umkristallisierung verwendete n-Butanol durch Eisessig ersetzt werden, erhält man einen Farbstoffbildner, der bei 195° C schmilzt und nach Farbentwicklung ein gelbes Bild mit einem Absorptionsmaximum bei 460 πιμ ergibt.(prepared according to Erlenmeyer, HeIv. Chim. Acta, 27 [1944], p. 1432, or Dann, Ber., 76 [1943], P. 419) and the n-butanol used for recrystallization is replaced by glacial acetic acid, is obtained a dye former which melts at 195 ° C and after color development a yellow image with a Absorption maximum at 460 πιμ results.
910 g Ketoester nach Beispiel 1 und 262 g 2-Amino-5-nitropyridin (hergestellt nach Plazek, Ber., 61 [1928], S. 1815) werden in 3 1 Toluol + 3 1 Xylol 24 Stunden am Rückflußkühler gekocht, und zwar so, daß das Toluol teilweise mit dem gebildeten Methanol abdestillieren kann. Beim Abkühlen des Reaktionsgemisches kristallisiert eine Verbindung aus, welche nach dem Umkristallisieren aus Acetonitril bei 143° C schmilzt.910 g of keto ester according to Example 1 and 262 g of 2-amino-5-nitropyridine (manufactured according to Plazek, Ber., 61 [1928], p. 1815) are refluxed in 3 1 toluene + 3 1 xylene for 24 hours, as follows: that the toluene can partially distill off with the methanol formed. When the reaction mixture cools A compound crystallizes out, which after recrystallization from acetonitrile at 143 ° C melts.
140 g dieser Verbindung werden in Anwesenheit von 85 g feinem Eisen in einer kochenden Mischung von 625 cm3 Acetonitril, 625 cm3 Eisessig und 125 cm3 Wasser reduziert. Nach dem Absaugen des nicht reagierten Eisens wird das Filtrat in ein Gemisch aus 1250 g Eis und 1250 cm3 konzentriertem Chlorwasserstoff gegossen. Der erhaltene Niederschlag wird abgesaugt, mit einer wäßrigen 2,5 n-Chlorwasserstofflösung gewaschen, bis kein Eisen mehr anwesend ist und dann in Chloroform aufgelöst. Die Lösung wird mit einer wäßrigen Natriumcarbonatlösung bis zur Säurefreiheit gewaschen, durch eine trockene Natriumsulfatschicht filtriert und zur Trockene eingedampft.140 g of this compound are reduced in the presence of 85 g of fine iron in a boiling mixture of 625 cm 3 of acetonitrile, 625 cm 3 of glacial acetic acid and 125 cm 3 of water. After the unreacted iron has been filtered off with suction, the filtrate is poured into a mixture of 1250 g of ice and 1250 cm 3 of concentrated hydrogen chloride. The precipitate obtained is filtered off with suction, washed with an aqueous 2.5 N hydrogen chloride solution until iron is no longer present and then dissolved in chloroform. The solution is washed with an aqueous sodium carbonate solution until it is free from acid, filtered through a dry layer of sodium sulfate and evaporated to dryness.
Der Rückstand wird mit Äther gewaschen; man erhält ein Amin, das nach Umkristallisierung aus Benzol bei 137° C schmilzt.The residue is washed with ether; an amine is obtained which, after recrystallization from benzene, is obtained Melts at 137 ° C.
89 g des Amins werden in 1 1 kochendem Benzol aufgelöst. Nach Zusatz von 37 g Maleinsäureanhydrid in 270 cm3 Benzol wird V2 Stunde unter Rückflußkühlung gekocht, dann abgekühlt, abgesaugt und mit Äther gewaschen. Man erhält einen Farbstoffbildner, der der folgenden Formel entspricht:89 g of the amine are dissolved in 1 liter of boiling benzene. After adding 37 g of maleic anhydride in 270 cm 3 of benzene, the mixture is refluxed for 1/2 hour, then cooled, filtered off with suction and washed with ether. A dye former is obtained which corresponds to the following formula:
CH3 CH 3
CH,CH,
CH3 CH 3
NH-CO-CH=CH-COOhNH-CO-CH = CH-COOh
-0-CH2-CH2-O--0-CH 2 -CH 2 -O-
CO-CHp-CO-NH-.CO-CHp-CO-NH-.
'N'N
CH3 CH 3
190° C (Zersetzung). Benzol ist der190 ° C (decomposition). Benzene is that
austhe end
Der Schmelzpunkt liegt bei
Nach dem Umkristallisieren
Schmelzpunkt unverändert.The melting point is
After recrystallization
Melting point unchanged.
Eine Lösung von 4 g dieses Farbstoffbildners wird zu 1 kg einer photographischen Silberhalogenidemulsion zugesetzt. Nach Vergießen dieser Emulsion auf einen Schichtträger sowie Belichten und Entwickeln erhält man ein gelbes Bild mit einem Absorptionsmaximum bei 445 πιμ.A solution of 4 g of this dye-former becomes 1 kg of a silver halide photographic emulsion added. After this emulsion has been poured onto a layer support, as well as exposure and development a yellow image is obtained with an absorption maximum at 445 πιμ.
8,6 g 2-Amino-5-carbäthoxythiazol werden in cm3 kochendem Xylol mit 25 g p-Cetyloxybenzoylessigsäureäthylester (hergestellt nach der deutschen Patentschrift 23 267) 6 Stunden kondensiert. Nach Abkühlen wird der Niederschlag abgesaugt und mit Benzol gewaschen. Man erhält einen Farbstoff bildner mit einem Schmelzpunkt von 150° C. Durch Kristallisation aus Methylcellosolve wird der Schmelzpunkt ίο nicht erhöht.8.6 g of 2-amino-5-carbäthoxythiazole are condensed in cm 3 of boiling xylene with 25 g of p-cetyloxybenzoyl acetic acid ethyl ester (prepared according to German Patent 23 267) for 6 hours. After cooling, the precipitate is filtered off with suction and washed with benzene. A dye former with a melting point of 150 ° C. is obtained. Crystallization from methyl cellosolve does not increase the melting point.
Der Farbstoffbildner entspricht der folgenden Formel:The dye former corresponds to the following formula:
H3C — (CH2)15 — O—/ V- CO — CH2- CO —NH-H 3 C - (CH 2 ) 15 - O— / V- CO - CH 2 - CO —NH-
Eine Lösung von 4 g dieses Farbstoffbildners wird zu 1 kg einer photographischen Silberhalogenidemulsion zugesetzt. Nach Vergießen dieser Emulsion ao auf einen Schichtträger sowie Belichten und Entwickeln erhält man ein gelbes Bild mit einem Absorptionsmaximum bei 455 ΐημ.A solution of 4 g of this dye-former becomes 1 kg of a silver halide photographic emulsion added. After this emulsion has been poured onto a layer support, as well as exposure and development a yellow image is obtained with an absorption maximum at 455 ΐημ.
Claims (2)
;N —CH.SC-COOC 2 H 5
; N - CH
festmachende Alkylgruppe und
cyclischen Ring bedeutet.is used in the R
mooring alkyl group and
means cyclic ring.
zeichnet, daß der Farbstoffbildner dem photo
graphischen Material einverleibt wird.2. The method according to claim 1, characterized
draws that the dye former corresponds to the photo
graphic material is incorporated.
Deutsche Auslegeschrift Nr. 1 000 233;
USA.-Patentschriften Nr. 2 357 395, 2 357 776.Considered publications:
German Auslegeschrift No. 1 000 233;
U.S. Patent Nos. 2,357,395, 2,357,776.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE568688D BE568688A (en) | 1957-06-19 | ||
| FR1239317D FR1239317A (en) | 1957-06-19 | ||
| DEG22339A DE1038916B (en) | 1957-06-19 | 1957-06-19 | Process for producing color photographic images |
| US742756A US3008827A (en) | 1957-06-19 | 1958-06-18 | Production of colored photographic images |
| GB19634/58A GB873125A (en) | 1957-06-19 | 1958-06-19 | Benzoyl acetamide colour couplers and their use in the production of coloured photographic images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG22339A DE1038916B (en) | 1957-06-19 | 1957-06-19 | Process for producing color photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1038916B true DE1038916B (en) | 1958-09-11 |
Family
ID=7121923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG22339A Pending DE1038916B (en) | 1957-06-19 | 1957-06-19 | Process for producing color photographic images |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3008827A (en) |
| BE (1) | BE568688A (en) |
| DE (1) | DE1038916B (en) |
| FR (1) | FR1239317A (en) |
| GB (1) | GB873125A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3186846A (en) * | 1960-06-10 | 1965-06-01 | Polaroid Corp | Process for producing silver halide emulsions containing gelatin derivatives |
| NL268720A (en) * | 1960-08-29 | |||
| BE634670A (en) * | 1963-07-09 | |||
| US3841880A (en) * | 1973-04-03 | 1974-10-15 | Eastman Kodak Co | Silver halide emulsion containing ketomethylene photographic color-forming couplers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2357395A (en) * | 1940-07-17 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2357776A (en) * | 1942-02-16 | 1944-09-05 | Colt S Mfg Co | Barrel support for automatic firearms |
| DE1000233B (en) * | 1954-12-20 | 1957-01-03 | Eastman Kodak Co | Color photographic material comprising at least one photographic silver halide emulsion containing an alkoxylated benzoylacetanilide coupler |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL49334C (en) * | 1935-08-07 | |||
| US2166181A (en) * | 1937-09-21 | 1939-07-18 | Pont Film Mfg Company Du | Color photography |
| GB524557A (en) * | 1938-10-26 | 1940-08-08 | Kodak Ltd | Improvements in and relating to photographic materials and the processing thereof |
| US2395776A (en) * | 1943-10-01 | 1946-02-26 | Gen Aniline & Film Corp | Color photography |
-
0
- FR FR1239317D patent/FR1239317A/fr not_active Expired
- BE BE568688D patent/BE568688A/xx unknown
-
1957
- 1957-06-19 DE DEG22339A patent/DE1038916B/en active Pending
-
1958
- 1958-06-18 US US742756A patent/US3008827A/en not_active Expired - Lifetime
- 1958-06-19 GB GB19634/58A patent/GB873125A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2357395A (en) * | 1940-07-17 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2357776A (en) * | 1942-02-16 | 1944-09-05 | Colt S Mfg Co | Barrel support for automatic firearms |
| DE1000233B (en) * | 1954-12-20 | 1957-01-03 | Eastman Kodak Co | Color photographic material comprising at least one photographic silver halide emulsion containing an alkoxylated benzoylacetanilide coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1239317A (en) | 1960-12-16 |
| GB873125A (en) | 1961-07-19 |
| BE568688A (en) | |
| US3008827A (en) | 1961-11-14 |
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