AT156356B - Process for sensitizing halogenated silver gelatin photographic emulsions. - Google Patents
Process for sensitizing halogenated silver gelatin photographic emulsions.Info
- Publication number
- AT156356B AT156356B AT156356DA AT156356B AT 156356 B AT156356 B AT 156356B AT 156356D A AT156356D A AT 156356DA AT 156356 B AT156356 B AT 156356B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- sensitizing
- photographic emulsions
- halogenated silver
- silver gelatin
- Prior art date
Links
- 239000000839 emulsion Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 5
- 108010010803 Gelatin Proteins 0.000 title claims description 4
- 229920000159 gelatin Polymers 0.000 title claims description 4
- 239000008273 gelatin Substances 0.000 title claims description 4
- 235000019322 gelatine Nutrition 0.000 title claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 title claims description 4
- 230000001235 sensitizing effect Effects 0.000 title description 3
- 206010070834 Sensitisation Diseases 0.000 claims description 7
- 230000008313 sensitization Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- -1 silver halide Chemical class 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002916 oxazoles Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- XGZVPYGIUMLWIE-UHFFFAOYSA-N ethyl hypoiodite Chemical compound CCOI XGZVPYGIUMLWIE-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Conversion Of X-Rays Into Visible Images (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
Gegenstand der Erfindung ist ein Verfahren zur Sensibilisierung von photographischen Halogen- silbergelatineemulsionen, wobei am mittelständigen Kohlenstoffatom substituierte symmetrische Oxocarboeyanine verwendet werden, die durch Umsetzung eines quartären Ammoniumsalzes eines einfachen oder substituierten Oxazols, das eine reaktionsfähige Methylgruppe in -Stellung zum Stickstoff enthält, von der allgemeinen Formel
EMI1.2
worin R'= Vinylen, Phenylen, Naphthylen usw.,
R = Alkyl,
X = Cl, Br, J, SO, CH" CIO, oder ein anderer Säurerest ist, mit einem Alkylester einer arylierten Thioimidsäure von der allgemeinen Formel
EMI1.3
erhalten werden. In der allgemeinen Formel ist Ei = Alkyl oder Aryl,
R2 = Alkyl,
Bs = Phenyl oder substituiertes Phenyl.
Die am mittelständigen Kohlenstoffatom substituierten Oxocarbocyanine sind besonders wert- volle Sensibilisatoren für photographische Halogensilbergelatineemulsionen. Sie übertreffen hinsichtlich ihrer sensibilisierenden Wirkung die entsprechenden nicht substituierten Farbstoffe. Die damit sensibilisierten Emulsionen arbeiten sehr klar und lassen sich gut desensibilisieren.
Die Ssnsibilisatoren sind für Kochemulsionen ebenso wie für Ammoniakemulsionen geeignet.
Sie können während der Emulsionsherstellung zugesetzt oder auch der fertigen Emulsionsschicht im Badeverfahren einverleibt werden. Die Farbstoffe werden in üblichen Mengen der Emulsion zugesetzt.
Diese betragen gewöhnlich 15-30 mg auf 1 kg giessfertiger Emulsion, doch können für besondere Zwecke auch grössere oder kleinere Mengen angewendet werden.
Im folgenden werden Beispiele der Farbstoffe dieser Klasse mit ihren entsprechenden Sensibilisierungsdaten und ihre Herstellungsweise angegeben.
Beispiel 1 : 10 g 2-Methylbenzoxazoljodäthylat werden mit 10 cm3 Äthylisothioacetanilid und 10 em3 Pyridin unter öfterem Rühren eine Stunde lang auf 130 C erhitzt.
Nach Erkalten wird die dickflüssige Farbstoffmasse mit 5 cm3 Methanol verrührt und 10 CM !" heisse 10% ige Kaliumjodidlösung zugegeben. Langsam kristallisiert der Farbstoff (orangefarbiges Pulver) aus, der abgesaugt und aus Alkohol umkristallisiert wird.
<Desc/Clms Page number 2>
EMI2.1
<tb>
<tb> Absorptionsmaximum...................................... <SEP> 488
<tb> Sensibilisierungsmaximum <SEP> 517 <SEP>
<tb> Sensibilisierungsbereich <SEP> ................................................ <SEP> 490-570 <SEP>
<tb>
EMI2.2
EMI2.3
EMI2.4
10 em3 Pyridin werden eineinhalb Stunden unter häufigem Rühren auf 130 C erhitzt. Die Farbstofflösung wird mit 5 em3 Methanol und 10 cm3 10%iger Kaliumjodidlösung versetzt.
Das ausfallende Öl wird durch Abgiessen von Wasser und Pyridin befreit, mit Wasser und dann mit Äther verrieben und schliesslich aus Alkohol umkristallisiert.
Der Farbstoff bildet ein rotgelbes Pulver.
EMI2.5
<tb>
<tb>
Absorptionsmaximum <SEP> 511 <SEP> lit
<tb> Sensibilisierungsmaximum <SEP> ................................................ <SEP> 500 <SEP>
<tb> Semibilisierungsbereich <SEP> 500-570 <SEP>
<tb>
Formel :
EMI2.6
Beispiel 3.10 g 2-Methylbenzoxazoljodäthylat, 5 cm3 Äthylisothiobutyranilid, 20 ein3 Pyridin werden eineinhalb Stunden auf 130 C erhitzt. Der Rohfarbstoff wird durch Verreiben mit Äther und dann mit Wasser gereinigt und schliesslich mit 20 em3 10% iger Natriumperchloratlosung versetzt. Der auskristallisierte Farbstoff wird abgesaugt und aus Alkohol umkristallisiert. Gelbrutes Pulver.
EMI2.7
<tb>
<tb> Absorptionsmaximum <SEP> 494 <SEP>
<tb> Sensibilisierungsmaximum.................................. <SEP> 535 <SEP> u. <SEP> u.
<tb>
Sensibilisierungsbereich <SEP> ................................................ <SEP> 490-500 <SEP>
<tb>
Formel :
EMI2.8
<Desc / Clms Page number 1>
EMI1.1
The invention relates to a process for sensitizing photographic halogen silver gelatin emulsions, using substituted symmetrical oxocarboeyanines on the central carbon atom, which are obtained by reacting a quaternary ammonium salt of a simple or substituted oxazole containing a reactive methyl group in -position to nitrogen from the general formula
EMI1.2
where R '= vinylene, phenylene, naphthylene, etc.,
R = alkyl,
X = Cl, Br, I, SO, CH "CIO, or another acid residue, with an alkyl ester of an arylated thioimidic acid of the general formula
EMI1.3
can be obtained. In the general formula, Ei = alkyl or aryl,
R2 = alkyl,
Bs = phenyl or substituted phenyl.
The oxocarbocyanines substituted on the central carbon atom are particularly valuable sensitizers for photographic silver halide gelatin emulsions. In terms of their sensitizing effect, they outperform the corresponding unsubstituted dyes. The emulsions sensitized with it work very clearly and can be easily desensitized.
The sensitizers are suitable for cooking emulsions as well as for ammonia emulsions.
They can be added during the preparation of the emulsion or can also be incorporated into the finished emulsion layer in the bath process. The dyes are added to the emulsion in the usual amounts.
These are usually 15-30 mg per 1 kg of ready-to-pour emulsion, but larger or smaller amounts can also be used for special purposes.
The following are examples of the dyes of this class with their respective sensitization data and their method of preparation.
Example 1: 10 g of 2-methylbenzoxazole iodoethylate are heated to 130 ° C. for one hour with 10 cm3 of ethylisothioacetanilide and 10 cm3 of pyridine with frequent stirring.
After cooling, the viscous dye mass is stirred with 5 cm3 of methanol and 10 cm! "Of hot 10% potassium iodide solution is added. The dye (orange powder) slowly crystallizes out, which is suctioned off and recrystallized from alcohol.
<Desc / Clms Page number 2>
EMI2.1
<tb>
<tb> absorption maximum ...................................... <SEP> 488
<tb> Sensitization maximum <SEP> 517 <SEP>
<tb> Sensitization area <SEP> ........................................... ..... <SEP> 490-570 <SEP>
<tb>
EMI2.2
EMI2.3
EMI2.4
10 cubic meters of pyridine are heated to 130 C for one and a half hours with frequent stirring. The dye solution is mixed with 5 em3 methanol and 10 cm3 10% potassium iodide solution.
The precipitated oil is freed from water and pyridine by pouring off, rubbed with water and then with ether and finally recrystallized from alcohol.
The dye forms a red-yellow powder.
EMI2.5
<tb>
<tb>
Absorption maximum <SEP> 511 <SEP> lit
<tb> Sensitization maximum <SEP> ........................................... ..... <SEP> 500 <SEP>
<tb> Semibilization range <SEP> 500-570 <SEP>
<tb>
Formula:
EMI2.6
Example 3.10 g of 2-methylbenzoxazole iodoethylate, 5 cm3 of ethylisothiobutyranilide, 20 cm3 of pyridine are heated to 130 ° C. for one and a half hours. The crude dye is cleaned by trituration with ether and then with water and finally 20 cubic meters of 10% sodium perchlorate solution is added. The dyestuff that has crystallized out is filtered off with suction and recrystallized from alcohol. Yellow powder.
EMI2.7
<tb>
<tb> Maximum absorption <SEP> 494 <SEP>
<tb> Sensitization maximum .................................. <SEP> 535 <SEP> u. <SEP> u.
<tb>
Sensitization area <SEP> .............................................. .. <SEP> 490-500 <SEP>
<tb>
Formula:
EMI2.8
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE156356X | 1932-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT156356B true AT156356B (en) | 1939-06-26 |
Family
ID=5677760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT156356D AT156356B (en) | 1932-01-18 | 1932-12-14 | Process for sensitizing halogenated silver gelatin photographic emulsions. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT156356B (en) |
-
1932
- 1932-12-14 AT AT156356D patent/AT156356B/en active
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