US3134673A - Photographic developers - Google Patents

Photographic developers Download PDF

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Publication number
US3134673A
US3134673A US88317A US8831761A US3134673A US 3134673 A US3134673 A US 3134673A US 88317 A US88317 A US 88317A US 8831761 A US8831761 A US 8831761A US 3134673 A US3134673 A US 3134673A
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US
United States
Prior art keywords
parts
methyl
salt
naphthalene
hydroxy
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.)
Expired - Lifetime
Application number
US88317A
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English (en)
Inventor
Ganguin Karl Otto
Crichton David William
Kaye Albert Edward
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ilford Imaging UK Ltd
Original Assignee
Ilford Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
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Publication of US3134673A publication Critical patent/US3134673A/en
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • 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
    • 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
    • G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring

Definitions

  • photographic developing compositions which comprise, in association with an alkaline substance, a compound of the general Formula I:
  • R is an alkyl group containing 1 to 6 carbon atoms
  • R is a methyl, ethyl, hydroxymethyl or hydroxyethyl group, or R and R together with the nitrogen atom to which they are joined constitute a pyrrolidine or piperidine nucleus
  • one of R and R is a trimethylene grouping of which the free valency is connected to the carbon atom of the benzene ring which is in ortho position to the nitrogen atom and the other ofR and R has any of the meanings assigned individually to R and R above or is a hydrogen atom
  • X is an alkyl group containing 1 or 2 carbon atoms or an alkoxy or substituted alkoxy group containing 1 to 6 carbon atoms or, where R or R forms part of a cyclic residue, is either a said alkyl, or alkoxy or substituted alkoxy group or a hydrogen atom.
  • Preferred compounds of the general Formula I are those in which the sum total number of carbon atoms in the groups R and R whether joined together or not, is at most four.
  • Preferred classes of compounds according to the present invention are:
  • R is alkyl of 1-6 carbon atoms
  • R is methyl, ethyl, hydroxymethyl or hydroxyethyl
  • X is methyl, methoxy, ethoxy or ,B-hydroxye-thoxy.
  • R is hydrogen or methyl and X is hydrogen.
  • the developing compositions contain, in addition to an alkaline substance and a compound of general Formula I, a proportion of hydroquinone.
  • the developing compounds of general Formula I can be used in association with other developing substances, apart from hydroquinone just mentioned, e.g. hydroquinone monosulphonate, phenyl glycine, ascorbic acid and reductones, pyrogallol and gentisic acid.
  • the invention further includes colour developing compositions which contain, in addition to a compound of general Formula I and an alkaline substance, a developing substance based on N.N-dialkyl p-phenylene diamine and derivatives thereof, e.g. the toluene analogues.
  • a developing substance based on N.N-dialkyl p-phenylene diamine and derivatives thereof e.g. the toluene analogues.
  • the compounds of general Formula I tend to increase the activity of the developers. It is a particularly important advantage of the compounds, however, that when present in such colour developing compositions which also contain colour couplers which tend to oxidise in the air, their presence, even in minor proportions, acts to minimise or inhibit such oxidation, i.e. developers thus formulated have a reduced tendency to the formationof a dye scum, in use or on keeping.
  • the developing compositions may contain either compounds of general Formula I per se or salts or anils thereof.
  • an oxidising agent e.g. ferric chloride
  • the compoiuid II is dissolved in water containing sufiicient acid to form a salt at temperature, e.g. between 15 and C., and an aqueous solution of between 0.1 and 0.2 mol. proportions of ferric chloride is added.
  • the reaction proceeds at room temperature but may be boiled to speed up the reaction and allowed to cool to room temperature.
  • the developer product may then be extracted from the reaction mixture by known methods such as crystallisation or solvent extraction.
  • the extract is shaken with a solution of 12.5 parts of sulphuric acid in 200 parts of water.
  • the aqueous layer is separated, concentrated to half volume and cooled.
  • the product is collected, washed with ethanol and crystallised from water.
  • 4-hydroxy-3-methyl N:N diethylaniline hemisulphate separates as colourless prisms, which melt with decomposition at between 256 C. and 258 C.
  • the product is found to contain 57.6% of carbon and 7.5% of hydrogen.
  • C11H17ON1/2H2SO4 requires 58.0% of carbon and 7.9% of hydrogen.
  • N-(4'-hydroxy-3-methylphenyl)-pyrrolidine separates as colourless needles which melt at between 84 C. and 85 C.
  • C H ON requires 74.6% of carbon and 8.5% of hydrogen.
  • the naphthalene-1:S-disulphonate (2:1 salt) of N-(4'-hydroxy-3-methylphenyl)pyrrolidine separates from water as colourless prisms which melt with decomposition at 272 C.
  • 4-amino-3-methyl-N-ethyl-N-/3- hydroxyethylaniline naphthalene-1:5-disulphonate (1:1 salt) used in making Developer B there are used 54 parts of 4-amino-3-rnethyl-N-n-heXyl-N-,B-hydroxyethylaniline naphthalene-1:S-disulphonate (1:1 salt) and in place of 6 parts of ferric chloride there are used 6 parts of potassium persulphate.
  • Example 1 Identical strips of a high speed black and White panchromatic negative film material (sold under the trade name Ilford HP3, the Word Ilford being a registered trademark) are exposed behind a sensitometric step wedge and equal numbers are then developed for different times in the following two developer solutions:
  • the processed step wedges are measured and the densit-ies plotted individually for each development time.
  • Example 2 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.386 part of N- (4 hydroxy-3'-methylphenyl)-pyrrolidine naphthalene- 1:5-disulphonate (2:1 salt) is incorporated in solution (b).
  • Example 3 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.179 part of 6- hydroxy-lz2z3z4-tetrahydroquinoline is incorporated in solution (b).
  • Example 4 The compound 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate was added in a proportion of 1 g./litre to a cyan colour developer which in the absence of said addition commenced to develop dye scum almost immediately after making. By the addition of the said compound the onset of dye scum was prevented for 36 hours.
  • Example 5 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.441 part of 4- :hydroxy 3 methyl-N-n-butyl-N 3-hyd-roxyethylaniline naphthalene-1:S-disulphona-te (2:1 salt) is incorporated in solution (b).
  • Example 6 In place 'of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.475 part of 4- hydroxy 3 methyl-N-n-hexyl-N-p-hydroxyethylaniline naphthalene-1:S-disulphonate (2:1 salt) is incorporated in solution (b).
  • Example 7 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.407 part of 4- hydroxy-3-methoxy-N:N-diethylaniline naphthalene-1 :5 disulphonate (2:1 salt) is incorporated in solution (b).
  • Example 8 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.327 part of N- (4-hydroxy-3-methy1phenyl) piperidine hydrobromide is incorporated in solution (b).
  • Example 9 In place of 0.274 part of 4-hydroxy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.370 part of 6- hydroxy 1 methyl-1z2z3z4-tetrahydroquinoline naphthalene-1:5-disulphonate (2:1 salt) is incorporated in solution (b).
  • Example 10 In place of 0.274 part of 4-hydroXy-3-methyl-N:N-diethylaniline hemisulphate in Example 1, 0.444 part of 4- hydroxy-B-(B-hydroxyethoXweN:N-diethylaniline naphthalene-lzS-disulphonate (2:1 salt) is incorporated in solution (b).
  • a photographic developing composition comprising an alkaline substance, hydroquinone and a salt of N-(4'-hydroxy-3-methylphenyl)pyrrolidine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US88317A 1960-02-19 1961-02-10 Photographic developers Expired - Lifetime US3134673A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6023/60A GB928671A (en) 1960-02-19 1960-02-19 Improvements in or relating to photographic developers

Publications (1)

Publication Number Publication Date
US3134673A true US3134673A (en) 1964-05-26

Family

ID=9807013

Family Applications (1)

Application Number Title Priority Date Filing Date
US88317A Expired - Lifetime US3134673A (en) 1960-02-19 1961-02-10 Photographic developers

Country Status (4)

Country Link
US (1) US3134673A (fr)
ES (1) ES264960A1 (fr)
GB (1) GB928671A (fr)
NL (1) NL261409A (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300305A (en) * 1962-10-25 1967-01-24 Eastman Kodak Co Color developers containing competing developing agents
US3549364A (en) * 1965-03-08 1970-12-22 Polaroid Corp Photographic processes and compositions
US3656950A (en) * 1970-12-03 1972-04-18 Eastman Kodak Co Color photographic processes
US3658525A (en) * 1970-12-03 1972-04-25 Eastman Kodak Co Reversal color photographic processes
US3790383A (en) * 1970-12-21 1974-02-05 Fuji Photo Film Co Ltd Infectious developer composition
US3804624A (en) * 1970-10-27 1974-04-16 Fuji Photo Film Co Ltd Method for developing silver halide photosensitive material
US3939164A (en) * 1974-02-08 1976-02-17 Smithkline Corporation 7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds
US3988339A (en) * 1974-02-08 1976-10-26 Smithkline Corporation Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase
US20050027751A1 (en) * 2003-04-23 2005-02-03 Dot Hill Systems Corporation Network, storage appliance, and method for externalizing an internal I/O link between a server and a storage controller integrated within the storage appliance chassis
WO2007059901A1 (fr) * 2005-11-22 2007-05-31 Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung_E.V. Capteur/indicateur d'oxygene a base organique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1937844A (en) * 1931-03-23 1933-12-05 Goodrich Co B F Photographic developer and method of developing
US2417514A (en) * 1940-09-23 1947-03-18 Spectrum Products Company Inc Method and means for producing colored photographic images
US2943109A (en) * 1957-05-27 1960-06-28 Ici Ltd Photographic developers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1937844A (en) * 1931-03-23 1933-12-05 Goodrich Co B F Photographic developer and method of developing
US2417514A (en) * 1940-09-23 1947-03-18 Spectrum Products Company Inc Method and means for producing colored photographic images
US2943109A (en) * 1957-05-27 1960-06-28 Ici Ltd Photographic developers

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300305A (en) * 1962-10-25 1967-01-24 Eastman Kodak Co Color developers containing competing developing agents
US3549364A (en) * 1965-03-08 1970-12-22 Polaroid Corp Photographic processes and compositions
US3804624A (en) * 1970-10-27 1974-04-16 Fuji Photo Film Co Ltd Method for developing silver halide photosensitive material
US3656950A (en) * 1970-12-03 1972-04-18 Eastman Kodak Co Color photographic processes
US3658525A (en) * 1970-12-03 1972-04-25 Eastman Kodak Co Reversal color photographic processes
US3790383A (en) * 1970-12-21 1974-02-05 Fuji Photo Film Co Ltd Infectious developer composition
US3939164A (en) * 1974-02-08 1976-02-17 Smithkline Corporation 7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds
US3988339A (en) * 1974-02-08 1976-10-26 Smithkline Corporation Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase
US20050027751A1 (en) * 2003-04-23 2005-02-03 Dot Hill Systems Corporation Network, storage appliance, and method for externalizing an internal I/O link between a server and a storage controller integrated within the storage appliance chassis
WO2007059901A1 (fr) * 2005-11-22 2007-05-31 Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung_E.V. Capteur/indicateur d'oxygene a base organique
US20080272336A1 (en) * 2005-11-22 2008-11-06 Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. Organic Oxygen Scavenger/Indicator
US8158019B2 (en) 2005-11-22 2012-04-17 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Organic oxygen scavenger/indicator

Also Published As

Publication number Publication date
GB928671A (en) 1963-06-12
NL261409A (fr)
ES264960A1 (es) 1961-05-16

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