DE167159C - - Google Patents
Info
- Publication number
- DE167159C DE167159C DENDAT167159D DE167159DA DE167159C DE 167159 C DE167159 C DE 167159C DE NDAT167159 D DENDAT167159 D DE NDAT167159D DE 167159D A DE167159D A DE 167159DA DE 167159 C DE167159 C DE 167159C
- Authority
- DE
- Germany
- Prior art keywords
- cyanines
- toluchinaldine
- dye
- quinoline
- red
- 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.)
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- 239000000975 dye Substances 0.000 claims description 15
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M CHEMBL593252 Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 7
- 230000001235 sensitizing Effects 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
- 231100000202 sensitizing Toxicity 0.000 claims description 3
- 230000001476 alcoholic Effects 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- RDFLLVCQYHQOBU-GPGGJFNDSA-O Cyanin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@H](CO)O1)c1c(-c2cc(O)c(O)cc2)[o+]c2c(c(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O3)cc(O)c2)c1 RDFLLVCQYHQOBU-GPGGJFNDSA-O 0.000 description 19
- -1 lepidine alkyl iodide Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 3
- YLAUVUQZNJMLEC-UHFFFAOYSA-N 2-methylquinoline;quinoline Chemical compound N1=CC=CC2=CC=CC=C21.C1=CC=CC2=NC(C)=CC=C21 YLAUVUQZNJMLEC-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N Quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Unter Cyanin versteht man bekanntlich den blauen Farbstoff, der erhalten wird, wenn man ein Gemenge von Chinolin- und Lepidinalkyljodid in alkoholischer Lösung mit Ätzalkali erhitzt. Als Spalteholz aus dem Gemenge der Chinaldinalkylhalogene und Chinolinalkylhalogene bei Behandeln derselben mit Alkali einen rotvioletten Farbstoff von ähnlichen Eigenschaften erhielt, wurde derAs is well known, cyanine is understood to mean the blue dye which is obtained when a mixture of quinoline and lepidine alkyl iodide in alcoholic solution is heated with caustic alkali. As split timber from the Mixture of the quinaldine alkyl halogens and quinoline alkyl halogens in treating the same obtained a red-violet dye with similar properties with alkali, the
ίο Name Cyanin auch auf diesen übertragen.ίο Name cyanine also transferred to this one.
Die Cyanine besitzen die sehr wertvolle Eigenschaft, die photographische Platte für gelbes, und rotes Licht zu sensibilisieren, und zwar erstreckt sich bei den blauen Lepidincyaninen die sensibilisierende Wirkung etwa bis zur Linie C im Rot des Spektrums, während die rotvioletten Chinaldincyanine nur bis -D Y2 C im Orange sensibilisieren.The cyanines have the very valuable property of sensitizing the photographic plate to yellow and red light; the sensitizing effect of the blue lepidine cyanines extends approximately to line C in the red of the spectrum, while the red-violet quinaldine cyanines only up to -DY 2 Sensitize C in orange.
Da die Chinaldincyanine vor den Lepidincyaninen in photographischer Beziehung verschiedene Vorzüge besitzen, eine möglichst weit ins Rot hineinreichende Sensibilisierung aber sehr erwünscht ist, so wurde versucht, Chinaldincyanine aufzufinden, deren sensibilisierende Wirkung über D 1J2 C hinausginge. Als Ausgangsprodukte für die Herstellung derartiger Cyanine wurden die im Benzolkern methylierten Chinolinbasen verwendet. Versuche mit Chinaldin- und o-Toluchinolinalkyljodid ergaben kein Resultat; es bildete sich überhaupt kein Farbstoff. Auch 0-T0-luchinaldin in Form seines Alkyljodids gab mit Chinolinalkyljodid nur eine ganz minimale Ausbeute an Farbstoff, so daß auch jene Base zur Herstellung von Cyaninen praktisch nicht geeignet ist.Since the quinaldine cyanines have various advantages over the lepidine cyanines in photographic terms, but a sensitization reaching as far into the red as possible is very desirable, an attempt was made to find quinaldine cyanines whose sensitizing effect went beyond D 1 J 2 C. The quinoline bases methylated in the benzene nucleus were used as starting materials for the production of such cyanines. Experiments with quinaldine and o-toluquinoline alkyl iodide gave no result; no dye formed at all. Even 0-T0-luchinaldine in the form of its alkyl iodide gave only a very minimal yield of dye with quinoline alkyl iodide, so that even that base is practically unsuitable for the production of cyanines.
Es war hiernach nicht zu erwarten, daß bei Verwendung der m- und p-substituierten Chinolinbase die gewünschte Farbstoffbildung eintreten würde. Die Versuche ergaben aber, daß in der Tat aus diesen Cyanin farbstoffen in guter Ausbeute erhalten werden können, die sich von dem bekannten Chinaldinchinolincyanin durch blauere Nuance unterscheiden.It was then not to be expected that when using the m- and p-substituted Quinoline base the desired dye formation would occur. But the experiments showed that in fact from these cyanine dyes can be obtained in good yield, which differ from the well-known quinaldine quinoline cyanine by a bluer shade.
Es wurden z. B. folgende neue Cyaninfarbstoffe
unter Verwendung der von m- und p-Toluchinolin und m- und p-Toluchinaldin
sich ableitenden Ammoniumbasen hergestellt: Chinaldin-m-toluchinolinalkylcyanin,
Chinaldin-p-toluchinolinalkylcyanin,There were z. B. produced the following new cyanine dyes using the ammonium bases derived from m- and p-toluchinoline and m- and p-toluchinaldine: quinaldine-m-toluchinoline-alkylcyanine,
Quinaldine-p-toluchinoline-alkylcyanine,
m-Toluchinaldinchinolinalkylcyanin,
m-Toluchinaldin-m-toluchinolinalkylcyanin,
m-Toluchinaldin-p-toluchmolinalkylcyanin,
p-Toluchinaldinchinolinalkyl cyanin,
p-Toluchinaldin-m-toluchinolinalkylcyanin,
p-Toluchinaldin-p-toluchinolinalkylcyanin.
Die neuen Cyanine, besonders diejenigen, die Derivate des p-Toluchinaldins sind, und
unter diesen speziell das p-Toluchmaldinchinolinmethylcyanin
und das p-Toluchinaldin-p-Toluchinolinäthylcyanin,
zeigen das gewünschte Sensibilisierungsvermögen für Rot und verleihen der photographischen Platte
eine 2Y2- bezw. 1 ^2 mal so große Empfindlichkeit
für Rot als das alte Chinaldinchinolincyanin. Diese Wirkung ist deutlich ausm-Toluchinaldinquinolinalkylcyanin,
m-toluchinaldine-m-toluchinoline-alkylcyanine, m-toluchinaldine-p-toluchinaldine-alkyl-cyanine, p-toluchinaldine-quinoline-alkyl-cyanine,
p-Toluchinaldine-m-toluchinoline alkylcyanine, p-Toluchinaldine-p-toluchinoline alkylcyanine. The new cyanines, especially those which are derivatives of p-Toluchinaldins, and among these especially p-Toluchmaldinchinolinmethylcyanin and p-Toluchinaldin-p-Toluchinolinäthylcyanin, show the desired sensitizing power for red and give the photographic plate a 2Y 2 - respectively. 1 ^ 2 times as sensitive to red as the old quinaldine quinoline cyanine. This effect is clearly evident
den betreffenden Spektrumphotographien zu ersehen, und es sind daher die neuen Cyanine für die Herstellung panchromatischer Platten wertvoll.can be seen in the relevant spectrum photographs, and it is therefore the new cyanines valuable for the production of panchromatic plates.
p-Toluchinaldin-p-toluchinolinäthylcyaninj odid.p-Toluchinaldin-p-toluchinolinäthylcyaninj odid.
30 g p-Toluchinaldinjodäthylat und 58 g p-Toluchinolinjodäthylat werden in etwa 800 ecm Alkohol gelöst und die heiße Lösung mit 6 g Ätzkali, in Alkohol gelöst, versetzt. Nach wenigen Minuten ist die Farbstoffbildung vollendet. Die tiefrote Lösung wird mit Äther versetzt, der ausgefällte Farbstoff durch Umkristallisieren aus Wasser und Alkohol gereinigt. Der reine Farbstoff bildet dunkelgrüne, glänzende Prismen, die sich leicht in heißem Alkohol, schwerer in heißem Wasser, sehr schwer in kaltem Wasser mit rotvioletter Farbe lösen.30 g of p-toluchinal dinjodethylate and 58 g p-Toluchinolinjodäthylat are approximately 800 ecm of alcohol dissolved and the hot solution with 6 g of caustic potash, dissolved in alcohol, offset. The dye formation is complete after a few minutes. The deep red solution ether is added and the precipitated dye is recrystallized from water and alcohol cleaned. The pure dye forms dark green, shiny prisms that Easily in hot alcohol, heavier in hot water, very difficult in cold Dissolve water with a red-violet color.
p-Toluchinaldinchinolinmethylcyaninjodid. p-Toluchinaldinequinoline methylcyanine iodide.
28 g p-Toluchinaldinjodmethylat werden m't 55 S Chinolinjodmethylat in etwa 800 ecm Alkohol gelöst und die heiße Lösung mit 6 g Ätzkali versetzt. Der gebildete Farbstoff scheidet sich beim Erkalten zum Teil aus. Aus Äthylalkohol kristallisiert der Farbstoff in feinen blaugrünen Nadeln; aus Methylalkohol erhält man zunächst die gleichen Kristalle, die sich bei einigem Stehen in der Mutterlauge in derbe messingglänzende Prismen verwandeln. Der Farbstoff löst sich ziemlich schwer in absolutem Alkohol und Wasser, leicht in verdünntem Alkohol mit rotvioletter Farbe und zeigt eine etwas gelbere Nuance als der in Beispiel I beschriebene Farbstoff.28 g p-Toluchinaldinjodmethylat be m 't 55 S Chinolinjodmethylat in about 800 cc of alcohol dissolved and the hot solution with 6 g of potassium hydroxide was added. Some of the dye formed separates out when it cools. The dye crystallizes in fine blue-green needles from ethyl alcohol; the same crystals are obtained from methyl alcohol, which transform into coarse, shiny brass prisms when standing in the mother liquor for a while. The dye dissolves rather poorly in absolute alcohol and water, easily in dilute alcohol with a red-violet color and shows a slightly more yellow shade than the dye described in Example I.
Die Herstellung der anderen neuen Cyanine unter Verwendung von Ammoniumbasen aus p- und m-Toluchinolinen und Toluchinaldinen erfolgt in analoger Weise, und sie sind in ihren Eigenschaften den -oben beschriebenen Cyaninen sehr ähnlich.The production of the other new cyanines made using ammonium bases p- and m-toluchinolines and toluchinaldines takes place in an analogous manner, and their properties are those described above Very similar to cyanines.
Die neuen Farbstoffe finden, wie erwähnt, Verwendung zum Sensibilisieren photographischer Platten bezw. Halogensilberemulsionen.As mentioned, the new dyes are used for photographic sensitization Plates resp. Halogen silver emulsions.
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