US2852374A - Photographic developer - Google Patents

Photographic developer Download PDF

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Publication number
US2852374A
US2852374A US494687A US49468755A US2852374A US 2852374 A US2852374 A US 2852374A US 494687 A US494687 A US 494687A US 49468755 A US49468755 A US 49468755A US 2852374 A US2852374 A US 2852374A
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United States
Prior art keywords
developer
group
aryl
developing
silver halide
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Expired - Lifetime
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US494687A
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English (en)
Inventor
Ulrich Hans
Mersch Rudolf
Wahl Ottmar
Delfs Detlef
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Agfa Gevaert NV
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Agfa AG
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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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/30—Developers
    • G03C5/3028—Heterocyclic compounds
    • G03C5/3035—Heterocyclic compounds containing a diazole ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/167—X-ray

Definitions

  • 1-phenyl-3-amino-pyrazoline has only a very slight activity as a photographic developer, so that it is of no practical value. The same also applies for its sulpho acid or carboxylic acid derivatives which are readily soluble in alkali. Moreover, the substitution of the aryl radical by aliphatic substituents does not provide any substantial change as regards the developing power.
  • 1-aryl-3-amino-pyrazolines which contain OH or NH groups as substituents in the aryl radical in the 4-position are highly active developers with very valuable photographic properties, it being possible for the hydrogen atoms of the NH group to be replaced by organic radicals as for instance by alkyl, oxalkyl, sulpho-alkyl or carboxy-alkyl groups. If necessary, the aryl radical may also carry other substituents apart from OH or NH groups, such as alkyl' groups and halogen atoms.
  • Such compounds are not only very rapidly acting photographic developers when used alone in alkaline solution, but they show super-additive effects to a degree not hitherto known, particularly in combination with known types of silver halide developing substances, such as pyrocatech'ol, pyrogallol', hydroquinone, p-aminophenol, oaminopl'ienol, oand p-aminophenols substituted in the aromatic nucleus of in the amino group, such as p-methylaminophenol and N-p-oxyphenyl'glycin, 2.4-diaminophenol, oand p-pheriylendiarnin and derivatives thereof.
  • the special action of the developer substances is also obtained, if they are present for instance in developing solutions which are used for developing silver halide layers, which contain known developing substances. Furthermore the developing substances according to the present invention may be incorporated into silver halide layers by themselves or in combi-nation with other known developing substances, whereafter these layers are developed either in alkaline aqueous solution or in alkaline aqueous solution containing developing substances.
  • developer mixtures are, therefore, characterizedby being particularly inexpensive. Furthermore, it is possible therewith to produce special developers for a wide variety of purposes in' the photographic art.
  • Example 1 A grey step wedge (factor f: ⁇ /5) is exposed on normal silver chloride paper (Agfa Lupex) of normal gradationon a sensitometer. The development is carried out at 20 C. in solutions of the following composition:
  • Developer B shows one grey stepmore
  • Developer C shows one grey step less
  • 7 Developer D shows eight grey steps more
  • Developer E shows only a flat image trace
  • Developer F shows only aflat image trace.
  • Example 2 Grey step wedges are exposed as in Example 1 on silver chloride or silver .bromide papers and developed in developers of the following composition:
  • This ratio is not changed in any way if the developer is subjected to the action of air in such manner that a moderate current of air is drawn in for twenty hours in gas-washing bottles.
  • developer B shows the deepest blackening.
  • Water NB S O s anhyd. Hydro quinone K 0 KBr p-Methylaminophenol 5 l-(p-hydroxyphenyD-B-ammopyrazoline 1- (p-acetaminzr phenyD-3-aminopyravnl in p l-(p-N-methylacetaminophenyl)-3-aminopyrum] in n From the diagram shown in the accompanying drawing it is readily possible to read off the sequence of the developers as regards their activity. It increases from the developer Pin the sequence F, E, D, B, A, C.
  • Example 4 In a developer A for silver chloride and silver bromide papers, of the following composition:
  • Prints are produced from a negative and developed in the aforesaid developers.
  • the printing process using the developer B takes only of the time of exposure required by developer A.
  • development of the image with developer B proceeds at higher velocity than with developer A.
  • the advance in time is about 15%.
  • Developer C works slowly and yields only a flat trace of an image.
  • the l-(p-methylaminophenyl) 3 amino-pyrazoline is obtained by refluxing 23.2 grams of l-(p-acetmethylaminophenyl)-3-aminoyrazoline (freezing point P. P. 263 C.) with 270 ml. of 10% aqueous sodium hydroxide solution for 10 hours and cooling the reaction mass, whereby the first mentioned compound crystallizes. It is transformed into the hydrochloride according to customary methods.
  • the 1-(p-ethylaminophenyl)-3-aminopyrazoline is produced by the same method from l-(pacetethylaminophenyl)-3-aminopyrazoline. (F. P. about C. under decomposition.)
  • Example 6 In a developer A for silver chloride and silver bromide papers, of the following composition:
  • developer B is more stable to oxidation by air and of higher capacity than developer A.
  • a solution containing a given amount of developer B is exhausted by developing 10 m? of a silver chloride paper, whereas 6 m. of the same paper suifice to exhaust the same amount of developer A.
  • Example 8 A highly active developer A for X-ray films has the composition
  • developer B contains, instead of p-methylaminophenol, only 0.09 gram of l-(p-aminophenyl)-3-amino-pyrazoline or 0.095 gram of l-(p-amino-m-methylphenyl)-3-amino-pyrazoline.
  • a comparison of the developing process with Agfa X-ray film shows that developer B has a greater capacity than developer A.
  • the 1(p-amino-m-methylphenyl)-3-aminopyrazoline is obtained by refluxing 23.2 grams of 1-(4'- acetylamino-3'-methylphenyl)-3-arninopyrazoline (F. P. 237 C.) with 230 ml. of 10% aqueous sodium hydroxide solution for 12 hours and thereafter cooling the reaction mass.
  • the crystals formed melt at 166 C. under decomposition.
  • a photographic developing agent which consists essentially of 1-aryl-3-aminopyrazoline, wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of OH and wherein R and R are members of the group consisting of hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl, in admixture with a silver halide developing substance comprising a benzene derivative having at least two sub stituents in the benzene nucleus, said substituents being selected from the group consisting of hydroxy and amino groups and being attached to the benzene nucleus at a position selected from the group consisting of the 1.4 and the 1.2 positions.
  • a photographic developing agent consisting essentially of an alkaline solution of hydroquinone and 1- aryl-3-aminopyrazoline, wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of H and wherein R and R are members of the group consisting of hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl.
  • a developing agent consisting essentially of l-paminophenyl-3-aminopyrazoline and hydroquinone.
  • a developing agent consisting essentially of 1-p-hydroxyphenyl-3-aminopyrazoline and hydroquinone.
  • the process of developing photographic silver halide layers which comprises treating the silver halide layers with a developing agent consisting essentially of an alkaline solution of l-aryl-3-aminopyrazoline wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of OH and wherein R and R are members of the group consisting of hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl.
  • a developing agent consisting essentially of an alkaline solution of l-aryl-3-aminopyrazoline wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of OH and wherein R and R are members of the group consisting of hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl.
  • the process of developing photographic silver halide layers which comprises treating the silver halide layers with a developing agent consisting essentially of l-aryl-3-aminopyrazoline wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of OH and wherein R and R are members of the group consisting of hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl in admixture with a silver halide developing substance comprising a benzene derivative having at least two substituents in the benzene nucleus, said substituents being selected from the group consisting of hydroxy and amino groups and being attached to the benzene nucleus at a position selected from the group consisting of the 1.4 and the 1.2 positions.
  • a developing agent consisting essentially of l-aryl-3-aminopyrazoline wherein the aryl group is substituted in the 4-position by a radical selected from the group consisting of OH and wherein
  • the process of developing photographic silver halide layers which comprises treating the silver halide layers with a developing agent consisting essentially of an alkaline solution of hydroquinone and 1-aryl-3-amin0- wherein R and R are members of the group consisting of pyrazoline wherein the aryl group is substituted in the hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl.
  • a developing agent consisting essentially of an alkaline solution of hydroquinone and 1-aryl-3-amin0- wherein R and R are members of the group consisting of pyrazoline wherein the aryl group is substituted in the hydrogen, alkyl, oxalkyl, sulfoalkyl, and carboxyalkyl.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
US494687A 1954-03-18 1955-03-16 Photographic developer Expired - Lifetime US2852374A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA19910A DE945606C (de) 1954-03-18 1954-03-18 Photographischer Entwickler

Publications (1)

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US2852374A true US2852374A (en) 1958-09-16

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US494687A Expired - Lifetime US2852374A (en) 1954-03-18 1955-03-16 Photographic developer

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US (1) US2852374A (enrdf_load_stackoverflow)
BE (1) BE536578A (enrdf_load_stackoverflow)
CH (1) CH333551A (enrdf_load_stackoverflow)
DE (1) DE945606C (enrdf_load_stackoverflow)
FR (1) FR1120915A (enrdf_load_stackoverflow)
GB (1) GB768071A (enrdf_load_stackoverflow)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE570596A (enrdf_load_stackoverflow) * 1957-08-26
BE598399A (enrdf_load_stackoverflow) * 1959-12-21
BE637358A (enrdf_load_stackoverflow) * 1962-09-15

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB679678A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to the production of 3-amino pyrazolines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB679678A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to the production of 3-amino pyrazolines

Also Published As

Publication number Publication date
CH333551A (de) 1958-10-31
BE536578A (enrdf_load_stackoverflow)
GB768071A (en) 1957-02-13
FR1120915A (fr) 1956-07-17
DE945606C (de) 1956-07-12

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