US2950970A - Color developers containing polyethylene glycols - Google Patents

Color developers containing polyethylene glycols Download PDF

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Publication number
US2950970A
US2950970A US644744A US64474457A US2950970A US 2950970 A US2950970 A US 2950970A US 644744 A US644744 A US 644744A US 64474457 A US64474457 A US 64474457A US 2950970 A US2950970 A US 2950970A
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United States
Prior art keywords
color
cyan
developer
emulsion
water
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
US644744A
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English (en)
Inventor
Judith A Schwan
Catherine Marilyn Spath
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.)
Eastman Kodak Co
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Eastman Kodak Co
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Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US644744A priority Critical patent/US2950970A/en
Priority to FR1205205D priority patent/FR1205205A/fr
Priority to GB7693/58A priority patent/GB859632A/en
Application granted granted Critical
Publication of US2950970A publication Critical patent/US2950970A/en
Priority to BE703341D priority patent/BE703341A/xx
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
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407Development processes or agents therefor
    • G03C7/413Developers

Definitions

  • the cyan development of the red-sensitive emulsion layer There are two important problems in connection withthe first color development step, that is, the cyan development of the red-sensitive emulsion layer.
  • the desired maximum cyan density must be obtained in the exposed regions with a minimum of cyan fog in the unexposed areas (i.e., cyan development in the green-sensitive or blue-sensitive layers which have not been re-exposed). Any attempt to increase cyan D-max. such as by prolonged cyan development is usually accompanied by an increase in cyan fog.
  • all of the exposedsllver halide grainsfrom the first re-exposure' must be completely reduced before subsequent magenta and yellow development in order to avoid magenta or yellow contamination. of the cyan layer.
  • a further object is to provide a color development giving dye images of increased maximum density or'D-max.
  • a still further object is to provide a methodfor increasing the density of. color developeddye images.
  • the remaining two emulsion layers are then successively exposed or rendered developable and developed in aplitiste color-forming developers, yellow for the bluesensitive emulsion and magenta for the green-sensitive emulsion. This produces positive dye images in each of the emulsion layers. All of the developed silver is then removed in a bleach which does not affect the dye images.
  • the maximum density of the dye images may be increased in this process by incorporating a non-ionic or iomc Patented Aug.. 30, 11960 tionare polymers derived from ethylene oxide.
  • the polymers which we employ should have a molecular weight of at least 600since the lower molecular weight. polymers do not show any appreciable accelerating effect.
  • NON-IONIC HO( C zc z 14CH2CH2OH Polyethylene glycolM.W. about 600 2) HO-(CH CH 0) CH CH OH Polyethylene g1ycolM.W. about 1500
  • a useful polyethylene glycol is Carbowax 1540, a product of'Car-b-id'e and Carbon Chemicals Corporation, which has the formula HO(CH CH O) CH CH OH where n has an'averagevalue of 35.
  • This polyethylene glycol is believed to be a mixture of compounds, and has an average molecular weight of 1300 to 1600,- a specific gravity of 1.15, a. freezing point of 43 to 46 C., a viscosity at 210 F. of 25 to 32 centistokes, a Cleveland Open Cup flash point of 510 F., and is by weight soluble in waterat 20 C.
  • Concentration of the benzene extracts yielded 102 g. (59 percent) of a light yellow viscous oil which turned to a semi-solid upon standing, Carbowax l540-,w-bis(methanesulfonate) (the yield can be improved by extracting the ester continuously in a liquid-liquid extractor from the weakly acidic solution).
  • COMPOUND 8 A mixture of 151 g. of Carbowax 4000 and g. of dimethyl isocyanatoglutarate was heated at 70 C. for hours, protected from atmospheric moisture. The resulting product was treated gradually with 6 g. of sodium hydroxide in 15 ml. of water. The mixture was heated at 60-70 C. for 3 hours, water being added occasionally to maintain the product in a fluid state. It was finally diluted with water to a total weight of 332 g. The resulting solution contained an estimated 166 g. of
  • the water can be removed from the product to yield a pale yellow solid.
  • Compound 7 is prepared as described in Carroll, Elins, Graham and Wilson application Serial No. 627,136.
  • Example 1 A high-speed gelatino-silver bromoiodide emulsion containing 0.24 mole of silver halide per liter was digested with a sulfur compound such as disclosed in Sheppard U.S. Patent 1,574,944 and potassium chloroaurate and optically sensitized to red light. To a portion of this emulsion there was added 0.66 gram per gram mole of silver halide of the condensation product of one mole of oleyl alcohol with approximately 25 moles of ethylene oxide (polyethylene glycol oleyl ether). These emulsions were separately coated on film base and were exposed on an Eastman type Ib sensitometer and developed for 3 minutes at 70 F. in a developer of the following" formula:
  • the films were flashed for 10 seconds with a No. 2 Reflector Photoflood 5 feet away. .
  • the portions of the films were then de-v veloped for from 3 to 5 minutes at F. in a cyan developer of the following composition and also in thissame developer to which 1 gram per liter of several.
  • films were bleached for two minutes in a solution having the following com- Water to 1 liter.
  • magenta developer had the following composition:
  • Emulsion without Emulsion contain- PEG ing PEG Daveloper Addenda Magenta Magenta Magenta Magenta D-ma.x. Fog D-max. Fog
  • Example 3 The eifect of the polyethylene glycols in a p-phenylene diamine developer containing a yellow coupler was also investigated. Development acceleration was noted with no increase in maximum color density but with shorter development time required for producing equal maximum densities. With the emulsion coating of Examples 1 and 2 containing the polyethylene glycol oleyl ether a maximum density of 1.45 at fog of 0.65 was attained after five minutes in the color developer containing w-benzoylacet-(p-toluene sulfonamido) anilide as the yellow coupler. These same values were attained with the developer containing the polyethylene glycol after only four minutes development.
  • a photographic color developer capable of producing dye images of increased dye density with no increase of color fog upon color development of a silver halide emulsion comprising a developing solution separate from said emulsion, containing an alkylamino paraphenylenediamine color developer, a coupler compound capable of coupling with the oxidation product of said developer to form a dye upon photographic development, and a polyethyleneglycol selected from the group consisting of (1) polyethylene glycols having the formula HO(CH CH 0),,CH CH OH where n is from 14 to 85, (2) polyethoxyethyl-bispyridinium methane sulfonate, and (3) polyethoxyethylbis-sulfuric acid.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US644744A 1957-03-08 1957-03-08 Color developers containing polyethylene glycols Expired - Lifetime US2950970A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US644744A US2950970A (en) 1957-03-08 1957-03-08 Color developers containing polyethylene glycols
FR1205205D FR1205205A (fr) 1957-03-08 1958-03-07 Nouveau révélateur pour la photographie en couleurs
GB7693/58A GB859632A (en) 1957-03-08 1958-03-10 Colour photography processes and developers therefor
BE703341D BE703341A (lt) 1957-03-08 1967-08-31

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US644744A US2950970A (en) 1957-03-08 1957-03-08 Color developers containing polyethylene glycols
FR1205205T 1958-03-07

Publications (1)

Publication Number Publication Date
US2950970A true US2950970A (en) 1960-08-30

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ID=33436248

Family Applications (1)

Application Number Title Priority Date Filing Date
US644744A Expired - Lifetime US2950970A (en) 1957-03-08 1957-03-08 Color developers containing polyethylene glycols

Country Status (4)

Country Link
US (1) US2950970A (lt)
BE (1) BE703341A (lt)
FR (1) FR1205205A (lt)
GB (1) GB859632A (lt)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51848B1 (lt) * 1970-01-16 1976-01-12
US3955983A (en) * 1971-04-02 1976-05-11 Fuji Photo Film Co., Ltd. Process for forming a color image on an exposed photosensitive material
JPS5240334A (en) * 1975-09-27 1977-03-29 Mitsubishi Paper Mills Ltd Method of processing color photographic elements
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
WO1987004533A1 (en) 1986-01-23 1987-07-30 Fuji Photo Film Company Limited Process for forming colored image
USH1020H (en) 1989-09-25 1992-02-04 Konica Corporation Developing solution for light-sensitive silver halide photographic material and method of forming photographic image making use of it
US5215873A (en) * 1989-11-21 1993-06-01 E. I. Du Pont De Nemours And Company Process for developing silver halide recording materials
JPH0648376B2 (ja) 1986-05-01 1994-06-22 コニカ株式会社 ハロゲン化銀カラ−写真感光材料の処理方法
US5344750A (en) * 1992-05-12 1994-09-06 Fuji Photo Film Co., Ltd. Color development processing method of silver halide color photographic material using a color developer where the color developing agent concentration and processing temperature are a function of bromide ion concentration
US5384232A (en) * 1991-12-02 1995-01-24 E. I. Du Pont De Nemours And Company Process for rapid access development of silver halide films using pyridinium as development accelerators
US5468594A (en) * 1991-09-02 1995-11-21 Fuji Photo Film Co., Ltd. Image forming process
EP1016917A2 (en) * 1998-12-31 2000-07-05 Eastman Kodak Company Color developing composition and method of use in photoprocessing
WO2012035314A1 (en) 2010-09-17 2012-03-22 Fujifilm Manufacturing Europe Bv Photographic paper
WO2021213762A1 (en) 2020-04-24 2021-10-28 Fujifilm Manufacturing Europe Bv Photographic paper

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2366737A (en) * 1941-05-27 1945-01-09 Du Pont 1,3-dioxolane modified organic products
US2531832A (en) * 1947-06-12 1950-11-28 Du Pont Silver halide developers containing polyethylene glycols
US2716062A (en) * 1953-07-01 1955-08-23 Eastman Kodak Co 4-hydroxy-6-alkyl-1, 3, 3a, 7-tetrazaindene stabilizers for emulsions sensitized with alkylene oxide polymers
US2772162A (en) * 1954-11-03 1956-11-27 Eastman Kodak Co Diacylaminophenol couplers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2366737A (en) * 1941-05-27 1945-01-09 Du Pont 1,3-dioxolane modified organic products
US2531832A (en) * 1947-06-12 1950-11-28 Du Pont Silver halide developers containing polyethylene glycols
US2716062A (en) * 1953-07-01 1955-08-23 Eastman Kodak Co 4-hydroxy-6-alkyl-1, 3, 3a, 7-tetrazaindene stabilizers for emulsions sensitized with alkylene oxide polymers
US2772162A (en) * 1954-11-03 1956-11-27 Eastman Kodak Co Diacylaminophenol couplers

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51848B1 (lt) * 1970-01-16 1976-01-12
US3955983A (en) * 1971-04-02 1976-05-11 Fuji Photo Film Co., Ltd. Process for forming a color image on an exposed photosensitive material
JPS5240334A (en) * 1975-09-27 1977-03-29 Mitsubishi Paper Mills Ltd Method of processing color photographic elements
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
WO1987004533A1 (en) 1986-01-23 1987-07-30 Fuji Photo Film Company Limited Process for forming colored image
JPH0648376B2 (ja) 1986-05-01 1994-06-22 コニカ株式会社 ハロゲン化銀カラ−写真感光材料の処理方法
USH1020H (en) 1989-09-25 1992-02-04 Konica Corporation Developing solution for light-sensitive silver halide photographic material and method of forming photographic image making use of it
US5215873A (en) * 1989-11-21 1993-06-01 E. I. Du Pont De Nemours And Company Process for developing silver halide recording materials
US5468594A (en) * 1991-09-02 1995-11-21 Fuji Photo Film Co., Ltd. Image forming process
US5384232A (en) * 1991-12-02 1995-01-24 E. I. Du Pont De Nemours And Company Process for rapid access development of silver halide films using pyridinium as development accelerators
US5344750A (en) * 1992-05-12 1994-09-06 Fuji Photo Film Co., Ltd. Color development processing method of silver halide color photographic material using a color developer where the color developing agent concentration and processing temperature are a function of bromide ion concentration
EP1016917A2 (en) * 1998-12-31 2000-07-05 Eastman Kodak Company Color developing composition and method of use in photoprocessing
EP1016917A3 (en) * 1998-12-31 2002-01-02 Eastman Kodak Company Color developing composition and method of use in photoprocessing
WO2012035314A1 (en) 2010-09-17 2012-03-22 Fujifilm Manufacturing Europe Bv Photographic paper
WO2021213762A1 (en) 2020-04-24 2021-10-28 Fujifilm Manufacturing Europe Bv Photographic paper

Also Published As

Publication number Publication date
FR1205205A (fr) 1960-02-01
BE703341A (lt) 1968-01-15
GB859632A (en) 1961-01-25

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