US2787544A - Method of making photographic packet emulsions - Google Patents

Method of making photographic packet emulsions Download PDF

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Publication number
US2787544A
US2787544A US476540A US47654054A US2787544A US 2787544 A US2787544 A US 2787544A US 476540 A US476540 A US 476540A US 47654054 A US47654054 A US 47654054A US 2787544 A US2787544 A US 2787544A
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US
United States
Prior art keywords
color
solvent
dispersion
packet
forming 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
US476540A
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English (en)
Inventor
Godowsky Leopold
Jerome J Duane
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Eastman Kodak Co
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Eastman Kodak Co
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
Priority to BE543744D priority Critical patent/BE543744A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US476539A priority patent/US2801170A/en
Priority to US476540A priority patent/US2787544A/en
Priority to GB34887/55A priority patent/GB798512A/en
Priority to GB35055/55A priority patent/GB791353A/en
Priority to DEE11702A priority patent/DE963295C/de
Priority to FR1151479D priority patent/FR1151479A/fr
Application granted granted Critical
Publication of US2787544A publication Critical patent/US2787544A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor

Definitions

  • This invention relates to color photography and particularly to. a method for making packet emulsions.
  • Our'novel methods consists in (l) mixing the coupler with a low boiling organic solvent for'the coupler as shown in the first three boxes of the drawing, anddisp ersing the mixture in gelatin asshown in tlie fourth bo r of theidrawing, (2) mixing the coupler dispersion withasik ver halide emulsion and forming "a packet dispersion of the coupler and silver halide in 'gelatin;a s 'shown in the fifth box of the drawing, and (3') adding a highboilin'g coupler solvent to the packet dispersionasjshown in the last box of the drawing.” In'thisway the.
  • ratiolof, coupler to high boiling crystalloidal coupler solyent can: be readily adjusted so that any ratiobetween lfi andlflA orlower is obtained.
  • Thismethlod not onlyperrnits improvedcolor separation to be obtainedwlien theliigh boiling solvent is added after formation of.the .pa ckets but it, also has: the advantage, that t'ofthe pa clretsfcon taining couplerwithout couplersolvept. any; number, of
  • Low boiling organic solvents in which the coupler is first dissolved and which may then be removed partially or completely prior to making the packets includenitro methane, nitroethane, methyl, ethyl andpropyl acetates, chloroform, and ethyl and butyl formate.
  • High boiling coupler solvents which are added to the packet dispersions are organic crystalloidal materials which are substantially water-insoluble, have low molecular weight, have a boiling point above 175 C., and have a high solvent action for the color-forming compound. and for the dyes formed from it, and are permeable to photographic developer and its oxidation products.
  • solvents include di-nrbutyl phthalate, triphenyl phosphate, tricresyl phosphate, N,n-butyl acetanilideand. other compounds disclosed on pages 2 and 3 of Jelley and Vittum U. S. Patent 2,322,027.
  • Patent 2,698,794 is preferably employed except that the high hoilingcrystalloidal solvent is not added to the coupler dispersion-or packet dispersion as in that application, but is separately dispersed andadded later.
  • a Wfl'telfiSOlllblQ poiymer such as the sodium salt of a copolymer of methacrylic acid? and methyl-wmethaerylate may be used together withv a packet-forming component such as the ammonium salt of styrene-maleamic acid to polymer.
  • a packet-forming component such as the ammonium salt of styrene-maleamic acid to polymer.
  • This type of water-soluble polymer is..not a necessity for the'formation of packets.
  • Naturallyfoccurring .vater-soluble polymers and modified naturally occurring water solu ble polymers can also be used,.e. g., alginfcarboxy methylcellulose, and cellulose sulfate Our invention will now be, illustrated by the following examples:
  • a cyan coupler dispersion was made by dissolving 3 grams of the coupler 2-[a-(2,4-di-tert-amylphenoxy)-n butyrylamino]-4,6-dichloro--methyl phenol in 300 cc. of ethyl acetate at 40 C., adding the solution to 100 cc. of a 5% solution of Alkanol B dispersing agent in 850 cc. of gelatin solution, and dispersing it therein. The dispersion was set on a chill plate at F., noodled and air dried at 78 C. and relative humidity.
  • Example 2 A cyan packet dispersion was made as in Example 1. A magenta packet dispersion was similarly made, using 100 grams of the magenta coupler 1-(2',4',6'-trichlorophenyl)-3-[3"-(2",4"'-di-tert. amylphenoxy acetamido)- 5 CC. Di-n-butyl phthalate 6 Gelatin (10% solution) 27 Alkanol B (10% solution) 6 Water 2 dispersed in a colloid mill.
  • the amount of coupler solvent (di-n-butyl phthalate) dispersion added to the packet emulsions is such that the ratio of couplers to coupler solvent is about 1:1, in order to obtain adequate dye density in the resulting coating.
  • ratios of coupler to coupler solvent of 1: /2, 1:% and even 1:0 can be employed with certain couplers or if a solvent such as benzyl alcohol is present in the developer. Higher ratios, such as 1:2, 1:3, etc., may also be employed.
  • our invention may be em.- ployed in making packet dispersions in a layer in which the packet emulsion is sensitive only to a single primary spectral region, either in single layer or in multi-layer coatings, or may be used in making packets in which two or more sensitive packets are mixed in a single photographic layer.
  • the method of incorporating a color former in a photographic packet emulsion which comprises mixing a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, with a low boiling water-insoluble organic solvent for the color-forming compound, said low-boiling solvent having a boiling point below C., dispersing the solution of color-forming compound and low boiling organic solvent in gelatin, mixing the colorformer dispersion with a gelatino-silver halide emulsion, forming in a gelatin continuous phase, a packet dispersion of said emulsion and color-former, and then mixing said packet dispersion with a solution of a substantially water-insoluble, low molecular weight organic crystalloidal solvent for the color-forming compound and for dyes formed therefrom, and which solvent has a boiling point above about C. and is permeable to photographic developer oxidation products, to form a packet dispersion of said color-forming compound containing said crystalloidal solvent.
  • the method of incorporating a color former in a photographic packet emulsion which comprises mixing a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, with a low boiling water-insoluble organic solvent for the color-forming compound, said low-boiling solvent having a boiling point below 125 C., dispersing the solution of color-forming compound and low boiling organic solvent in gelatin, drying said dispersion to remove substantially all organic solvent, mixing the color-former dispersion with a gelatino-silver halide emulsion, forming in a gelatin continuous phase, a packet dispersion of said emulsion and color-former, with a styrene interpolymer having carboxyl groups on the polymeric chain, and then mixing said packet dispersion with a solution of a substantially water-insoluble, low molecular weight organic crystalloidal solvent for the colorforming compound and for dyes formed therefrom, and which solvent has a boiling point above about 175 C. and is permeable to
  • the method of incorporating a color former in a photographic packet emulsion which comprises mixing a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, with a low boiling waterinsoluble organic solvent for the color-forming compound, said low-boiling solvent having a boiling point below 125 C., dispersing the solution of color-forming compound and low boiling organic solvent in gelatin, drying said dispersion to remove substantially all organic solvent, mixing the colorformer dispersion with a gelatino-silver halide emulsion, forming in a gelatin continuous phase a packet dispersion of said emulsion and color-former, with a styrene interpolymer having carboxyl groups on the polymeric chain, separately dispersing in gelatin a substantially water- Insoluble, low molecular weight organic crystalloidal solvent for the color-forming compound and for dyes formed therefrom, and which solvent has a boiling point above about 175 C. and is permeable to photographic developer oxidation products, and
  • the method of incorporating a color former in a photographic packet emulsion which comprises mixing a color forming compound capable of reacting with a primary aromaticamino developing agent on photographic development, with ethyl acetate, dispersing the solution of color-forming compound and ethyl acetate in gelatin, drying said dispersion to remove substantially all ethyl acetate, mixing the color-former dispersion with a gelatino-silver halide emulsion, forming in a gelatin continuous phase a packet dispersion of said emulsion and color-former with the ammonium salt of a styrenemaleamic acid polymer, separately dispersing di-n-butyl 5 phthalate in gelatin, and mixing said packet dispersion and said di-n-butyl phthalate dispersion to form a packet dispersion of said color-forming compound and di-n-butyl phthalate.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Pyridine Compounds (AREA)
US476540A 1954-12-20 1954-12-20 Method of making photographic packet emulsions Expired - Lifetime US2787544A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE543744D BE543744A (de) 1954-12-20
US476539A US2801170A (en) 1954-12-20 1954-12-20 Preparation of color former dispersions
US476540A US2787544A (en) 1954-12-20 1954-12-20 Method of making photographic packet emulsions
GB34887/55A GB798512A (en) 1954-12-20 1955-12-06 Method of making photographic packet emulsions
GB35055/55A GB791353A (en) 1954-12-20 1955-12-07 Method of making dispersions of colour couplers for use in light-sensitive silver salt emulsions
DEE11702A DE963295C (de) 1954-12-20 1955-12-18 Verfahren zur Einlagerung eines Kupplers oder Farbstoffbildners in eine photographische Halogensilber-Gelatineemulsion
FR1151479D FR1151479A (fr) 1954-12-20 1955-12-19 Procédé pour l'incorporation de coupleurs chromogènes aux émulsions photosensibles et nouveaux produits obtenus

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US476539A US2801170A (en) 1954-12-20 1954-12-20 Preparation of color former dispersions
US476540A US2787544A (en) 1954-12-20 1954-12-20 Method of making photographic packet emulsions

Publications (1)

Publication Number Publication Date
US2787544A true US2787544A (en) 1957-04-02

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Application Number Title Priority Date Filing Date
US476539A Expired - Lifetime US2801170A (en) 1954-12-20 1954-12-20 Preparation of color former dispersions
US476540A Expired - Lifetime US2787544A (en) 1954-12-20 1954-12-20 Method of making photographic packet emulsions

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Application Number Title Priority Date Filing Date
US476539A Expired - Lifetime US2801170A (en) 1954-12-20 1954-12-20 Preparation of color former dispersions

Country Status (5)

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US (2) US2801170A (de)
BE (1) BE543744A (de)
DE (1) DE963295C (de)
FR (1) FR1151479A (de)
GB (2) GB798512A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2949360A (en) * 1956-08-31 1960-08-16 Eastman Kodak Co Photographic color former dispersions
US3012885A (en) * 1956-12-03 1961-12-12 Eastman Kodak Co Pressure image transfer process
US5008179A (en) * 1989-11-22 1991-04-16 Eastman Kodak Company Increased activity precipitated photographic materials
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US5770352A (en) * 1996-04-18 1998-06-23 Eastman Kodak Company High activity photographic dispersions with ultra low levels of permanent solvent
US5830632A (en) * 1996-10-31 1998-11-03 Eastman Kodak Company Photographic element containing dispersions of high dye-yield couplers having improved photographic activity
US5879867A (en) * 1997-08-22 1999-03-09 Eastman Kodak Company Silver halide light-sensitive element
US5891613A (en) * 1997-08-22 1999-04-06 Eastman Kodak Company Silver halide light-sensitive element
US6420103B1 (en) 1999-03-10 2002-07-16 Eastman Kodak Company Photographic element
US20050089806A1 (en) * 2003-10-24 2005-04-28 Zengerle Paul L. Method of preparation of direct dispersions of photographically useful chemicals

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE590403A (de) * 1959-04-30
US3244524A (en) * 1960-03-01 1966-04-05 Gen Aniline & Film Corp U. v. absorbing composition
US3244518A (en) * 1960-05-19 1966-04-05 Gen Aniline & Film Corp Process for obtaining multicolor images and a multilayer sheet for use therein
US3092495A (en) * 1960-06-09 1963-06-04 Gen Aniline & Film Corp Lower alkyl lactate coupler solvents
US3515557A (en) * 1965-04-12 1970-06-02 Du Pont Photographic color film and process of making same
DE3031404A1 (de) * 1980-08-20 1982-04-01 Agfa-Gevaert Ag, 5090 Leverkusen Verfahren zur herstellung von dispersionen und fotografische materialien
JPS59188641A (ja) 1983-04-11 1984-10-26 Fuji Photo Film Co Ltd ハロゲン化銀写真乳剤
US4725529A (en) 1985-04-30 1988-02-16 Konishiroku Photo Industry Co., Ltd. Developing inhibitor arrangment in light-sensitive silver halide color photographic materials
EP0204530B1 (de) 1985-05-31 1991-09-11 Konica Corporation Verfahren zur Herstellung eines direkt positiven Farbbildes
JPH0711695B2 (ja) 1985-09-25 1995-02-08 富士写真フイルム株式会社 撮影用ハロゲン化銀カラー感光材料の処理方法
AU591540B2 (en) 1985-12-28 1989-12-07 Konishiroku Photo Industry Co., Ltd. Method of processing light-sensitive silver halide color photographic material
JPH0833628B2 (ja) 1987-12-15 1996-03-29 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
US4970139A (en) * 1989-10-02 1990-11-13 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US5089380A (en) * 1989-10-02 1992-02-18 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
DE4433637A1 (de) 1994-09-21 1996-03-28 Agfa Gevaert Ag Farbfotografisches Silberhalogenidmaterial
US5585230A (en) * 1995-03-23 1996-12-17 Eastman Kodak Company Cyan coupler dispersion with improved stability
US5726003A (en) * 1996-08-15 1998-03-10 Eastman Kodak Company Cyan coupler dispersion with increased activity
US5932404A (en) * 1996-12-18 1999-08-03 Eastman Kodak Company Silver halide photographic material containing a polymer with a photographically useful group which is rendered non-diffusible by cross-linking
US7223529B1 (en) 2006-05-05 2007-05-29 Eastman Kodak Company Silver halide light-sensitive element

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB540368A (en) * 1939-01-23 1941-10-15 Eastman Kodak Co Improvements in and relating to colour couplers and to colour photographic materialscontaining them
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2698794A (en) * 1950-04-15 1955-01-04 Eastman Kodak Co Mixed packet photographic emulsions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB540368A (en) * 1939-01-23 1941-10-15 Eastman Kodak Co Improvements in and relating to colour couplers and to colour photographic materialscontaining them
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2698794A (en) * 1950-04-15 1955-01-04 Eastman Kodak Co Mixed packet photographic emulsions

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2949360A (en) * 1956-08-31 1960-08-16 Eastman Kodak Co Photographic color former dispersions
US3012885A (en) * 1956-12-03 1961-12-12 Eastman Kodak Co Pressure image transfer process
US5008179A (en) * 1989-11-22 1991-04-16 Eastman Kodak Company Increased activity precipitated photographic materials
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US5770352A (en) * 1996-04-18 1998-06-23 Eastman Kodak Company High activity photographic dispersions with ultra low levels of permanent solvent
US5830632A (en) * 1996-10-31 1998-11-03 Eastman Kodak Company Photographic element containing dispersions of high dye-yield couplers having improved photographic activity
US5879867A (en) * 1997-08-22 1999-03-09 Eastman Kodak Company Silver halide light-sensitive element
US5891613A (en) * 1997-08-22 1999-04-06 Eastman Kodak Company Silver halide light-sensitive element
US6420103B1 (en) 1999-03-10 2002-07-16 Eastman Kodak Company Photographic element
US20050089806A1 (en) * 2003-10-24 2005-04-28 Zengerle Paul L. Method of preparation of direct dispersions of photographically useful chemicals
US7338756B2 (en) 2003-10-24 2008-03-04 Eastman Kodak Company Method of preparation of direct dispersions of photographically useful chemicals

Also Published As

Publication number Publication date
FR1151479A (fr) 1958-01-30
BE543744A (de)
GB798512A (en) 1958-07-23
DE963295C (de) 1957-05-02
GB791353A (en) 1958-02-26
US2801170A (en) 1957-07-30

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