US3265502A - Photographic developing compositions - Google Patents

Photographic developing compositions Download PDF

Info

Publication number
US3265502A
US3265502A US203750A US20375062A US3265502A US 3265502 A US3265502 A US 3265502A US 203750 A US203750 A US 203750A US 20375062 A US20375062 A US 20375062A US 3265502 A US3265502 A US 3265502A
Authority
US
United States
Prior art keywords
group
bath
developing
hydroquinone
compound
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
US203750A
Other languages
English (en)
Inventor
Willems Jozef Frans
George Frans Van Veclen
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.)
Gevert Photo Producten N V
Gevert Photo-Producten N V
Original Assignee
Gevert Photo Producten N V
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
Application filed by Gevert Photo Producten N V filed Critical Gevert Photo Producten N V
Application granted granted Critical
Publication of US3265502A publication Critical patent/US3265502A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29Development processes or agents therefor
    • G03C5/30Developers

Definitions

  • a further object of this invention is to provide developing compositions comprising hydroquinone and a p-phenylene diamine derivative as described hereinafter.
  • Each of R and R represents a member selected from the group consisting of an alkyl radical such as an ethyl radical and a substituted alkyl radical such as a hydroxyethyl radical, and
  • X represents an electro-negative group suchas an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonamido group and an alkoxy group, and
  • R represents a member selected from the group consisting of a hydrogen atom and an alkyl radical
  • Each of R and R represents a member selected from the group consisting of a hydrogen atom and an alkyl radical
  • n represents an integer from at least 2 and at most 3,
  • X represents a member selected from the group consisting of a hydrogen atom, an alkyl radical and anelectronegative group such as an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonamido group and an alkoxy group.
  • N,N,N,N' tetramethyl p phenylene diamine dihydrochloride (2) N,N,N',N'-tetraethyl-p-phenylene diamine dihydrochloride (3) N,N-diethyl-N,N-dimethyl-p-phenylene diamine dihydrochloride (4) N,N diethyl N Z-hydroxyethyl N ethyl pphenylene diamine disulfate (5) N,N diethyl N 4 sulfobutyl N ethyl pphenylene diamine (b) Compounds according to general Formula II:
  • Compound 11 is prepared by the alkylation of tetrahydroquinoline with butane sultone followed by coupling with the diazonium salt of 2,4-dichloroaniline and reduction of the azo dyestufl.
  • Said compounds are weak developing agents if used in the absence of hydroquinone.
  • a developing bath according to this invention may also contain ingredients such as buffer compositions which may comprise salts such as carbonates, borates, phosphates, bisulfites, metabisulfites, sulfites and acids such as boric acid and citric acid.
  • the developing bath may further contain potassium bromide, water-softening agents such as polyphosphates or derivatives of ethylene diamine tetraacetic acid, antifogging agents and moistening agents, as well as other compounds known in the developing technique.
  • the pH of the baths can vary within wide limits, preferably between 8 and 11, so that a quick and hard development or a slow and soft development can be obtained at will.
  • the ratio of hydroquinone to a p-phenylene diamine derivative used in the present invention can be chosen in such a way that the bath composition is suited for the development of all kinds of materials including materials having silver chloride emulsion layers of low sensitivity as well as materials having highly sensitive silver brornoiodide emulsion layers.
  • the ratio of hydroquinone to the p-phenylene diamine derivatives used in the present invention can vary within lwide limits.
  • the amounts are, however, generally chosen in such a way that the hydroquinone strongly outweighs the said p-phenylene diamine derivatives.
  • a strong superadditive effect is already obtained with a ratio of 50 mg. of a p-phenylene diamine derivative used in this invention to 5 g. of hydroquinone per litre. Larger amounts can also be used, although the superadditive effect which is obtained with concentrations of 1 to 2 g. of said p-phenylene diamine derivative and 5 to g. of hydroquinone per litre, is not much higher than With concentrations which are 10 times lower.
  • the developing solutions according to this invention containing a combination of developing agents as described above, show with regard to the developing combination of hydroquinone and p-monomethylaminophenol hemisulfate the advantage that for a same developing activity a lower concentration of developing agents can be used.
  • the developing agents used in the present invention show more particularly with regard to the developing combination of hydroquinone and l-phenyl-B-pyrazolidone the advantage of being stable to hydrolysis, even in strong alkaline medium.
  • Example I Strips of a photographic material comprising a lightsensitive silver bromoiodide emulsion layer, coated onto a cellulose triacetate support, are exposed through a grey filter with a light-quantity (E) which corresponds to the shoulder part of the density/log E curve.
  • E light-quantity
  • Each of these exposed strips are developed at 20 C. in separate developing baths.
  • One of them is developed in a bath A containing as developing agent only hydroquinone and having the following composition:
  • the other strips are respectively developed in baths, having the same composition as bath A but containing moreover an equivalent amount of a developing agent as listed in Table 1 given hereinafter.
  • the densities are determined respectively after a developing time of 1, 3, 5
  • Example 2 Strips of a photographic material comprising a lightsensitive silver bromoiodide emulsion layer, coated on a cellulose triacetate support, are exposed through a grey filter with a light-quantity ('E) which corresponds to the shoulder part of the density/ log E curve.
  • 'E light-quantity
  • One of these film strips is developed in a bath B having the following composition:
  • the other strips are respectively developed in baths having the same composition as bath B but moreover containing an equivalent amount of a developing agent as listed in Table 2 given hereinafter.
  • the other strips are respectively developed in developing baths having the same composition as bath D, but containing moreover an equivalent amount of a developing agent as listed in Table 4 given hereinafter.
  • Photographic developing solution comprising hydroquinone and a derivative of p-phenylene diamine having a pol-arographic half-wave potentialwhich is at least 40 mv. more negative than that of N,N-diethyl-p-phenylene diamine and corresponding to a general formula selected from the group consisting of:
  • each of R R and R represents a lower alkyl radical
  • Y represents a member selected from the group consisting of a hydrogen atom, a hydroxyl group, and a sulfonic acid group and salts thereof
  • n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group; and an integer of at least 3 and at most 8 when Y represents a sulfonic acid group
  • each of R and R represents a member selected from the group consisting of an alkyl radical a lower and a hydroxy-substituted lower alkyl radical, and X represents an electro-negative group selected from the group consisting of an amino group, a monoalkylamino group, a dialkylamino group, a sulfonamido group and an alkoxy group;
  • R is a lower alkyl radical
  • R and R each represent a member selected from the group consisting of a hydrogen atom and a lower alkyl radical
  • n an integer of at least 2 and at most 3
  • X represents a member selected firom the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonam-ide group and an alkoxy (IV H3 H;
  • X represents a member selected from the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a sulfonamido group and an alkoxy p;
  • Photographic developing solution containing per liter from 5 g. to g. of hydroquinone and from 50 mg. to 2 g. of a p-phenylene diamine derivative having a polarographic half-wave potential which is at least 40 mv. more negative than that of N,N-diethyl-p-phenylene diamine and corresponding to a general formula selected from the group consisting of:
  • each of R R and R represents a lower alkyl radical
  • Y represents a member selected from the group consisting of a hydrogen atom a hydroxyl group, and a sulfonic acid group and salts thereof,
  • n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group; and an integer of at least 3 and at most 8 when Y represents a sulfonic acid group;
  • each of R and R represents a member selected from the group consisting of a lower alkyl radical and a hydroxy substituted lower alkyl radical
  • n represents an integer of at least 2 and at most 3
  • X represents a member selected from the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a monalkylamino group, a dialkyl amino group, a sulfonamide group and an alkoxy group;
  • each of R R and R represents a lower alkyl radical
  • Y represents a member selected from the group consisting of a hydrogen atom, a hydroxyl group and a sulfonic acid group in free acid and salt form
  • n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group, but an integer of at least 3 and at most 8 when Y represents a sulfonic acid group;
  • each of R and R represents a member selected from the group consisting of a lower alkyl radical and .a hydroxy-substituted lower alkyl radical
  • X represents an electro-negative group selected from the group consisting of an amino group, a monoalkylamino group, a dialkylamino group, a sulfonwherein:
  • amido group and X represents a member selected from the group conan alkoxy group; sisting of a hydrogen atom, a lower alkyl radical, an amino group, a sulfonamido group and an alkoxy (III) 1 5 group; RFN (V.) and the salts thereof.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US203750A 1961-06-21 1962-06-20 Photographic developing compositions Expired - Lifetime US3265502A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE2040745 1961-06-21

Publications (1)

Publication Number Publication Date
US3265502A true US3265502A (en) 1966-08-09

Family

ID=3864750

Family Applications (1)

Application Number Title Priority Date Filing Date
US203750A Expired - Lifetime US3265502A (en) 1961-06-21 1962-06-20 Photographic developing compositions

Country Status (4)

Country Link
US (1) US3265502A (no)
BE (1) BE605204A (no)
DE (1) DE1282454B (no)
GB (1) GB989383A (no)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3723117A (en) * 1969-10-27 1973-03-27 Agfa Gevaert Method for developing silver halide emulsions
US3767403A (en) * 1970-12-01 1973-10-23 Agfa Gevaert Nv Tetra-alkyl p-phenylene diamine with aromatic primary amino color developing agent
US4004926A (en) * 1974-04-02 1977-01-25 Agfa-Gevaert N.V. Formation of azine dyes
US4514494A (en) * 1982-11-12 1985-04-30 Agfa-Gevaert N.V. Photographic color material incorporating developing agents for color development
US5492796A (en) * 1993-10-28 1996-02-20 Fuji Photo Film Co., Ltd. Silver halide color photographic material and processing method thereof
US6265141B1 (en) * 1993-07-24 2001-07-24 Fuji Photo Film Co., Ltd. Color developing agent, processing liquid composition and color image-forming method

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE969677C (de) * 1952-04-25 1958-07-03 Hauff G M B H Verfahren zur Herstellung eines aktivierten photographischen Schwarzweissentwicklers
US2848326A (en) * 1955-09-26 1958-08-19 Eastman Kodak Co Method for preparing masked images

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE969677C (de) * 1952-04-25 1958-07-03 Hauff G M B H Verfahren zur Herstellung eines aktivierten photographischen Schwarzweissentwicklers
US2848326A (en) * 1955-09-26 1958-08-19 Eastman Kodak Co Method for preparing masked images

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3723117A (en) * 1969-10-27 1973-03-27 Agfa Gevaert Method for developing silver halide emulsions
US3767403A (en) * 1970-12-01 1973-10-23 Agfa Gevaert Nv Tetra-alkyl p-phenylene diamine with aromatic primary amino color developing agent
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
US4004926A (en) * 1974-04-02 1977-01-25 Agfa-Gevaert N.V. Formation of azine dyes
US4514494A (en) * 1982-11-12 1985-04-30 Agfa-Gevaert N.V. Photographic color material incorporating developing agents for color development
US6265141B1 (en) * 1993-07-24 2001-07-24 Fuji Photo Film Co., Ltd. Color developing agent, processing liquid composition and color image-forming method
US5492796A (en) * 1993-10-28 1996-02-20 Fuji Photo Film Co., Ltd. Silver halide color photographic material and processing method thereof

Also Published As

Publication number Publication date
GB989383A (en) 1965-04-14
BE605204A (no)
DE1282454B (de) 1968-11-07

Similar Documents

Publication Publication Date Title
US2691589A (en) Photographic developer compositions
US3867151A (en) General purpose monobath
US3265502A (en) Photographic developing compositions
US2371740A (en) Developers containing silver halide solvents
US3232761A (en) Hardening of photographic gelatin layers
US3552969A (en) Photographic compositions and processes
US3705806A (en) Polyquaternary ammonium bisulfites,sulfites and pyrosulfites as developer preservatives
US3157502A (en) Stabilized physical developers containing ionogenic surfactants
US3772018A (en) Azodicarbonamides as photographic bleaching agents
US3628955A (en) Inhibition of silvering in photographic solutions
ATE199461T1 (de) Photographische entwicklerzusammensetzung ohne hydrochinon und verarbeitungsverfahren
US3769014A (en) Beta-disulfone silver halide solubilizing agents
US3740221A (en) Development of photographic material
US3883354A (en) Color reversal process and developer
JPS5837644A (ja) 露光剤写真用ハロゲン化銀x線フィルムの自動処理法
US3809563A (en) Method for processing light-sensitive silver halide color photographic materials
US3574621A (en) Process for the development of photographic silver images in acid medium 1,4-diazine
US2782120A (en) Combined developer and fixer
US2404774A (en) Photographic developing process
US3295975A (en) Black-and-white developer for photographic reversal processes
US3667951A (en) Photographic stabilizing baths inhibited against corrosion with polyalkylene glycols
US2477323A (en) Photographic developers
US2374563A (en) Stabilized diazo-type sensitive material
US3318701A (en) Photographic monobaths containing a dl 6-8 dithio-octanoic acid antisludging agent
US3723117A (en) Method for developing silver halide emulsions