US2482546A - Phenoxyalkylamines as accelerators for photographic developers - Google Patents

Phenoxyalkylamines as accelerators for photographic developers Download PDF

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Publication number
US2482546A
US2482546A US37965A US3796548A US2482546A US 2482546 A US2482546 A US 2482546A US 37965 A US37965 A US 37965A US 3796548 A US3796548 A US 3796548A US 2482546 A US2482546 A US 2482546A
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United States
Prior art keywords
color
development
developer
silver
developing
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Expired - Lifetime
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US37965A
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English (en)
Inventor
Frank J Kaszuba
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.)
GAF Chemicals Corp
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General Aniline and Film Corp
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Filing date
Publication date
Priority to BE490074D priority Critical patent/BE490074A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US37965A priority patent/US2482546A/en
Priority to GB14279/49A priority patent/GB658575A/en
Priority to DEP45570A priority patent/DE851719C/de
Priority to CH280519D priority patent/CH280519A/fr
Priority to FR990475D priority patent/FR990475A/fr
Application granted granted Critical
Publication of US2482546A publication Critical patent/US2482546A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C5/305Additives other than developers

Definitions

  • Thistinvention relates to photographic develop'ers'and particularly to phenoxyalkylamines as accelerators for photographic developers.
  • amines such as primary and secondary alkyl and alkylene amines containing from 3 to '7. carbon atoms, 7 and heterocycli'c amines. such as morpholine' and piperidine as disclo'sed in United States Patent No'. 2,304,025, maybe added to photographic black and white and color developing solutions for the purpose of increasing the rate of development.
  • these amines accelerate the development so as. to cause thedeveloping agent to form the image .(silverl er cio'ljr im' e). more rapidly than i-s"po'ssible without the'preserlfce of suchfamines;
  • an object of the present invention to provide a black and white and color developer having an increased rate of development so that the developing time is substantially decreased to about one-half of the normal time, and which developer is less toxic than those heretofore used.
  • phenoxyalkylamines employed in accordancewith the present invention are represented by the following general formulae:
  • chlorine, bromine and the n is a positive integer of from 2 to 3
  • X ' is hydrogen, a nitro group, or a halogen such as The following are examples of such phenoxy- 'fl Phenoxyethylamine .sstationsamateurish fl-ti-nitroph euoxy) -ethylaniine o emeemase,
  • the sulfate and hydrochloride salts are readily prepared by the addition of a stoichiometrical quantity of dilute sulfuric acid and hydrochloric acid, respectively, and the carbonate is prepared by bubbling CO2, into an alcohol, ether, or benzene solution of the base.
  • the developing time is cut from 20-30 minutes to 2-10 minutes. All of the layers are simultaneously developed, and the dye images formed are of excellent quality.
  • the developing time with black and white developers for instance, solutions of hydroquinone and p-monomethylaminephenol sulfate and the like, is also out to about one-half without causing fog when such solutions contain a phenoxyalkylamine. 7
  • the most useful concentrations in black and White and color developers range from about 1 to 8 grams per liter of developer solution.
  • Example I p-Monomethylaminophenol sulfate grams 0.08 Sodium sulfite (anhydrous) do 45 Hydroquinone do 1.2 Sodium carbonate (monohydrate) do 8 Potassium metabisulfite do 4 Potassium bromide do 1.5 fi-Phenoxyethylamine do 4 Water to make liter 1
  • This tank developer gives, on development at 20 C. of the usual roll film, a negative in about 6 to 8 minutes after fixing and washing. The time required to develop a similar roll in the same developer and at the same temperature, but containing no B-phenoxyethylamine, ranges from 15 to 20 minutes. Increasing the concentration of the ,8-phenoxyethy1amine to 6 grams per liter eifects a further decrease in time.
  • Example II The following developer requires 30 minutes at 20 C. to give a satisfactory degree of color development with color paper:
  • the color photographic multi-layer element utilized in the foregoing example consists of an integral tri-pack emulsion coated on either the usual paper base, or a clear cellulose acetate or nitrate film base, or in some cases an opaque white film base.
  • Each of the emulsion layers is sensitized to one of the primary colors of light, namely, blue, green, and red.
  • the top layer is ..-blue sensitive.
  • a filter layer, yellow in color and blue absorbing, lies under the top layer. Below this filter layer, lies a green sensitive emulsion layer, and below this a red sensitive emulsion layer.
  • Each of the three silver-halide emulsion layers contains dye forming compounds which unite during the development of a silver image in an aromatic amine developing agent to form a dye with the oxidation product of the developing agent.
  • a yellow dye is formed in the blue sensitive emulsion; a magenta dye is formed in the green sensitive emulsion; and a cyan dye is formed in the red sensitive emulsion.
  • the combination of the dye images from these three printing primaries yields the color picture.
  • Suitable methods for the preparation of multi-color emulsion layers have been described in the literature relating to color photography, and are, therefore, not described here.
  • Example III The following developer requires 19 minutes at 20 C. to give a satisfactory degree of color de-
  • a color paper of excellent color rendition is developed in about 8 minutes.
  • Increasing the concentration of the amine to 6 grams reduces the time of development to 6 minutes with the same results.
  • Example IV The color developer of the preceding example with the addition of 5 grams of [3-phenoxyethy1- amine developed a multi-layer color film sheet, of the reversal type, and containing color formers fast to diffusion, in about 8 minutes at 20 C whereas without the 18-phenoxyethylamine, the,
  • time required to color develop the said film sheet is over 30 minutes.
  • R and R1 represent a group selected from the class consisting of hydrogen and methyl, R being hydrogen when R1 is methyl and R1 being hydrogen when R is methyl, 'n is a positive integer of from 2 to 3, and X is a group selected from the class consisting of hydrogen, nitro and halogen, and the salts of said amines.
  • the step comprising the development of an exposed silver-halide emulsion in an alkaline developer containing an aromatic silver-halide developing agent for said emulsion and a developing accelerator selected from the class consisting of phenoxyalkylamines corresponding to thefollowing formulae:
  • R and R1 represent a group selected from the class consisting of hydrogen and methyl, R being hydrogen when R1 is methyl and R1 being hydrogen when R is methyl, n is a positive integer of from 2 to 3, and X is a group selected from the class consisting of hydrogen, nitro and halogen, and the salts of said amines.
  • the step comprising the development of an exposed silver-halide emulsion an; alkaline developer: containing" 18.1! aromatic siliverehalide developing agent for said" emulsionand a deyelrfi oping accelerator characterized by the formula:
  • the step comprising the development of an exposed silver-halide emulsion in an alkaline developer containing an aromatic silver-halide developingagent for said emulsion and a developing accelerator characterized by the formula:
  • the step comprising the development of an exposed silver-halide emulsion in an alkaline developer containing an aromatic silver-halide developing agent for said emulsion and a developing accelerator characterized by the formula:
  • a color -forming photographic developer comprising a primary aromatic amino developing agent and a phenoxyalkylamine selected from the class consisting of those corresponding to the following formulae:
  • a color-forming photographic developer 7 8 cqmprismg a primary aromatiearnino develoging REFERENCES CITED agent and a phenoxyalkylamlne characterlzed by the following formula: v V
  • the following references are of record in the file of this patent:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US37965A 1948-07-09 1948-07-09 Phenoxyalkylamines as accelerators for photographic developers Expired - Lifetime US2482546A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE490074D BE490074A (US20080138455A1-20080612-C00006.png) 1948-07-09
US37965A US2482546A (en) 1948-07-09 1948-07-09 Phenoxyalkylamines as accelerators for photographic developers
GB14279/49A GB658575A (en) 1948-07-09 1949-05-27 Phenoxyalkylamines as accelerators for photographic developers
DEP45570A DE851719C (de) 1948-07-09 1949-06-12 Beschleuniger fuer photographische Entwickler
CH280519D CH280519A (fr) 1948-07-09 1949-07-04 Révélateur photographique contenant un accélérateur.
FR990475D FR990475A (fr) 1948-07-09 1949-07-09 Phénoxyalkylamines employées comme accélérateurs pour les révélateurs photographiques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US37965A US2482546A (en) 1948-07-09 1948-07-09 Phenoxyalkylamines as accelerators for photographic developers

Publications (1)

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US2482546A true US2482546A (en) 1949-09-20

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US37965A Expired - Lifetime US2482546A (en) 1948-07-09 1948-07-09 Phenoxyalkylamines as accelerators for photographic developers

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US (1) US2482546A (US20080138455A1-20080612-C00006.png)
BE (1) BE490074A (US20080138455A1-20080612-C00006.png)
CH (1) CH280519A (US20080138455A1-20080612-C00006.png)
DE (1) DE851719C (US20080138455A1-20080612-C00006.png)
FR (1) FR990475A (US20080138455A1-20080612-C00006.png)
GB (1) GB658575A (US20080138455A1-20080612-C00006.png)

Cited By (17)

* 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
US3002997A (en) * 1958-01-29 1961-10-03 Polaroid Corp Photographic products, processes and compositions
US3129100A (en) * 1961-03-16 1964-04-14 Agfa Ag Developing accelerators for silver halide emulsion layers
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
EP0452886A2 (en) 1990-04-17 1991-10-23 Fuji Photo Film Co., Ltd. Method of processing a silver halide color photographic material
WO1991019399A1 (en) * 1990-06-01 1991-12-12 Thomson Consumer Electronics, Inc. Chrominance processing system
EP0507145A1 (en) * 1991-04-03 1992-10-07 Minnesota Mining And Manufacturing Company Alkaline black-and-white developer for silver halide photographic material
US5310633A (en) * 1992-05-13 1994-05-10 Fuji Photo Film Co., Ltd. Bleach-fixing composition for color photographic material and method for processing a color photographic material with the same
US5362610A (en) * 1991-10-28 1994-11-08 Konica Corporation Photographic processing agent
US5366853A (en) * 1991-11-06 1994-11-22 Konica Corporation Tablet-shaped processing agent and method for processing silver halide photographic light sensitive materials
EP0631185A1 (en) 1993-06-11 1994-12-28 Fuji Photo Film Co., Ltd. Method for continuously processing silver halide color photosensitive material
US5409805A (en) * 1993-07-29 1995-04-25 Konica Corporation Solid processing agent for silver halide photographic light-sensitive materials
US5452045A (en) * 1992-10-30 1995-09-19 Konica Corporation Apparatus for processing a light-sensitive silver halide photographic material
EP0686875A1 (en) 1994-06-09 1995-12-13 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic materials
EP0720049A2 (en) 1990-05-09 1996-07-03 Fuji Photo Film Co., Ltd. Photographic processing composition and processing method using the same
US5576161A (en) * 1994-08-12 1996-11-19 Konica Corporation Silver halide light-sensitive photographic material and method of processing thereof
US5766830A (en) * 1994-09-09 1998-06-16 Konica Corporation Photographic processing method for processing a silver halide photographic light-sensitive material

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2181941A (en) * 1936-12-14 1939-12-05 Agfa Ansco Corp Photographic developer
US2327813A (en) * 1939-08-03 1943-08-24 Eastman Kodak Co Photographic solution
US2371740A (en) * 1942-03-20 1945-03-20 Eastman Kodak Co Developers containing silver halide solvents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2181941A (en) * 1936-12-14 1939-12-05 Agfa Ansco Corp Photographic developer
US2327813A (en) * 1939-08-03 1943-08-24 Eastman Kodak Co Photographic solution
US2371740A (en) * 1942-03-20 1945-03-20 Eastman Kodak Co Developers containing silver halide solvents

Cited By (18)

* 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
US3002997A (en) * 1958-01-29 1961-10-03 Polaroid Corp Photographic products, processes and compositions
US3129100A (en) * 1961-03-16 1964-04-14 Agfa Ag Developing accelerators for silver halide emulsion layers
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
EP0452886A2 (en) 1990-04-17 1991-10-23 Fuji Photo Film Co., Ltd. Method of processing a silver halide color photographic material
EP0720049A2 (en) 1990-05-09 1996-07-03 Fuji Photo Film Co., Ltd. Photographic processing composition and processing method using the same
WO1991019399A1 (en) * 1990-06-01 1991-12-12 Thomson Consumer Electronics, Inc. Chrominance processing system
US5478706A (en) * 1991-04-03 1995-12-26 Minnesota Mining And Manufacturing Company Alkaline black-and-white developer for silver halide photographic material
EP0507145A1 (en) * 1991-04-03 1992-10-07 Minnesota Mining And Manufacturing Company Alkaline black-and-white developer for silver halide photographic material
US5362610A (en) * 1991-10-28 1994-11-08 Konica Corporation Photographic processing agent
US5366853A (en) * 1991-11-06 1994-11-22 Konica Corporation Tablet-shaped processing agent and method for processing silver halide photographic light sensitive materials
US5310633A (en) * 1992-05-13 1994-05-10 Fuji Photo Film Co., Ltd. Bleach-fixing composition for color photographic material and method for processing a color photographic material with the same
US5452045A (en) * 1992-10-30 1995-09-19 Konica Corporation Apparatus for processing a light-sensitive silver halide photographic material
EP0631185A1 (en) 1993-06-11 1994-12-28 Fuji Photo Film Co., Ltd. Method for continuously processing silver halide color photosensitive material
US5409805A (en) * 1993-07-29 1995-04-25 Konica Corporation Solid processing agent for silver halide photographic light-sensitive materials
EP0686875A1 (en) 1994-06-09 1995-12-13 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic materials
US5576161A (en) * 1994-08-12 1996-11-19 Konica Corporation Silver halide light-sensitive photographic material and method of processing thereof
US5766830A (en) * 1994-09-09 1998-06-16 Konica Corporation Photographic processing method for processing a silver halide photographic light-sensitive material

Also Published As

Publication number Publication date
BE490074A (US20080138455A1-20080612-C00006.png)
FR990475A (fr) 1951-09-21
CH280519A (fr) 1952-01-31
DE851719C (de) 1952-10-06
GB658575A (en) 1951-10-10

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