US3779765A - Silver halide emulsions containing coupler solvents - Google Patents

Silver halide emulsions containing coupler solvents Download PDF

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Publication number
US3779765A
US3779765A US00285288A US3779765DA US3779765A US 3779765 A US3779765 A US 3779765A US 00285288 A US00285288 A US 00285288A US 3779765D A US3779765D A US 3779765DA US 3779765 A US3779765 A US 3779765A
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United States
Prior art keywords
coupler
silver halide
solvent
halide emulsion
color photographic
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Expired - Lifetime
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US00285288A
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English (en)
Inventor
F Mccrossen
H Osborn
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent

Definitions

  • This invention relates to color photography and pargraphic systems.
  • each of said emulsion layers in r r? Rm I turn, normally contain dispersed particles consisting of 0- cH,
  • the 5 ratio of coup1er-to solvent can usefully vary from about 0.5l:23 (ref. .lelley U.S. Pat. Nos.
  • Emulsion layers thickened by coupler sol- R" is defined as an arylcarbonyl group such as a phevents tend to be less durable and image resolution of nylcarbonyl or a naphthylcarbonyl group, or an alkylpoorer quality.
  • nyl group of two to 13 carbon atoms such as mebeing made to cut down on the amount of solvent withhylcarbonyl and dodecylcarbony out corresponding loss in coupler reactivity or dye stais defined as an alkoxy carbonyl group having up bility.
  • known high boiling crystalloidal I0 15 Carbon atoms, particularly two to 13 carbon coupler solvents have been used in combination with atoms u a methoxycarbonyl ordodecyloxycarboremovable auxiliary solvents to initially dissolve the y ,and n is an integer of 1-1000.
  • coupler (ref. Julian U.S. Pat. No. 2,949,360; Mannes Of particular interest as coupler solvents are esters of U.S. Pat. No. 2,304,939; .lelley et al. U.S. Pat. No. f fQl'mulae 2,322,827; Vittum U.S. Pat. No. 2,801,170; Fierke U.S. Pat. Nos. 2,801,171 and 2,490,749; Rinaura U.S. (F) 0 R Pat. No. 3,554,755, Thirtle et al. U.S. Pat. No. 11
  • H CH J H CH: 495a,, t e saw in which R and n are defined as above; permanent coupler solvents are defined as highboiling hydrophobic coupler solvents having a boiling point of about 175 C. which are permanently retained (H) i 10 as droplets dispersed within the silver halide emulsion (CH3)2CHCOCHEC$HCH(CHB)Z layer of a color photographic element.
  • Permanent sol- CH; 0CCH(CH,); vents of particular interest are specifically described in the following table l-lV relating to formulae B-F supra.
  • Permanent solvents such as group (D), supra, are obtainable, for instance, by reacting pentaerithritol with methyllaurate in the presence of titanium butoxide as catalyst at a molar ratio of about I 1-4 with continuous removal of methanol-by-product.
  • 1 I I9 250 CHF CH supplemental amount in reference to additional per- 20 850 CHi- CHi- C2H,-,- manent coupler solvents is intended to cover about 1 s. percent-67 percent (by volume) of the total amount of (D) CH,--0- - ⁇ 1v permanent coupler solvent used in dissolving a coupler, 33 percent or less (by volume) being preferred; low- H2 boiling auxiliary solvent” is defined as an organic solor vent of either hydrophilic or hydrophobic type which (E) Hic-R has a low-boiling point within the range of about 65 to about C.
  • Hi -R" litallast d non diffusible cyan dye-forming couplers suitable for use in the present invention are exemplified or suggested in U.S. Pat. Nos. 2,373,293; 2,423,730; 2,801,171; 2,895,826; 2,908,573; 3,046,- 129; 3,516,831; 3,311,476; 3,253,294; 3,458,315; 3,227,550; 3,476,563; 3,458,315; 3,419,390 and 3,034,892.
  • DIR Development Inhibitor Releasing
  • couplers can also be usefully included in the silver halide emulsion layers within the present invention.
  • Compounds of this type are exemplified, for instance, in U.S. Pat. Nos. 3,227,554; 3,148,062 and in U.S.
  • An effective amount for non-diffusible couplers of the above type can range from about 5-200 mg/ft per emulsion layer of coated material, a concentration of l050 mg/ft' being generally satisfactory.
  • DIR coupler is utilized in addition to 2- and/or 4- equivalent dye-forming couplers, it is found thatabout 5-30 mole percent of the former (i.e. DIR coupler) is adequate.
  • Color photographic elements within the scope of the present invention are preferably multilayered an usefully contain one or more of the following components:
  • a support layer as described, for instance, in Section X of Product Licensing Index, Vol. 92, Publication 9232 (Dec. 1971).
  • Typical supports include cellulose acetate film, polystyrene film,
  • polyethylene film polypropylene film, polyethylene terephthalate film, etc.
  • Typical suitable silver halide emulsions include silver chloride, silver bromide, silver chlorobromide, silver bromoiodide, silver chlorobromoiodide, and silver chloroiodide-emulsions.
  • gelatin spacer layers can also be included between the light-sensitive emulsion layers and also a Carey-Lea filter layer; spacer layers of this type can optionally contain removable additives -to further improve dye stability and improve color separation and D.
  • a protective gelatin overcoat layer can also be included between the light-sensitive emulsion layers and also a Carey-Lea filter layer; spacer layers of this type can optionally contain removable additives -to further improve dye stability and improve color separation and D.
  • a protective gelatin overcoat layer can be included between the light-sensitive emulsion layers and also a Carey-Lea filter layer; spacer layers of this type can optionally contain removable additives -to further improve dye stability and improve color separation and D.
  • the emulsified material was chill set, water washed and dired to remove auxiliary solvent and the melted dispersioiiblended w i tli a light sensitive 'gel'afi' manner and loss in dye density reported in Table IV in terms of density units.
  • R" is defined as an arylcarbonyl group or an alkylcarbonyl group
  • R" is defined as an alkoxy carbonyl group having up to carbon atoms and n is an integer of l-lOOO.
  • the improvement comprising utilizing as permanent coupler solvent at least one compound of the formulae wherein R'-" are individually defined at each occurrence as a hydrogen atom, or an alkyl group of one to eight carbon atoms; and
  • R" is a phenyl carbonyl group or an alkyl carbonyl group of two to 13 carbon atoms.
  • the improvement comprising utilizing as permanent coupler solvent at least one compound of the formulae wherein R'-'-R" and R"" are individually defined at each occurrence as a hydrogen. atom or an alkyl group of one to eight carbon atoms; and n is an integer of 1-1000.
  • the improvement comprising utilizing as permanent coupler solvent at least one compound of the formula HzC-R RVI. vr
  • R is defined as an alkoxy carbonyl group of two to 15 carbon atoms.
  • the permanent coupler solvent is a member selected from the group consisting of pentaerythritol tetrabenzoate; tetracarbethoxy propane; pentaerythritol tetralaurate; tris (2,2,4-trimethylpentyl) trimellitate; 1,2,4-benzenetricarboxylic acid, tris (2- ethylhexyl)ester; 2,2,4-
  • trimethylpentanediol-l,3-adipic acid polyester terminated with isobutyric acid.
  • a light sensitive photographic silver halide emulsion having dispersed therein finely divided particles containing at least one color photographic coupler compound in a solvent system comprising at least one compound of the formulae II (R wherein R'" and'R" are individually defined ateach occurrence as a hydrogen atom or a lower alkyl group;
  • R" is defined as an arylcarbonyl group or an alkylcarbonyl group
  • R is defined as an alkoxy carbonyl group having up to 15 carbon atoms and n is an integer of 1-1000.
  • a light sensitive photographic silver halide emulsion having dispersed therein finely divided particles having at least one color photographic coupler and a permanent coupler solvent of the formulae R-R" are individually defined at each occurrence as a hydrogen atom or an alkyl group of one to eight carbon atoms; and R is a phenyl carbonyl group or an alkyl carbonyl group of two to 13 carbon atoms.
  • R'R" and R" are individually defined at'each occurrence as a hydrogen atom or an alkyl group of one to eight carbon atoms;
  • n is an integer of 1-1000.
  • a light sensitive photographic silver halide emulsion having dispersed therein finely divided particles containing at least one photographic coupler and a permanent coupler solvent of the formula R is defined as an alkoxy carbonyl group of two to 15 carbon atoms.
  • a light sensitive photographic silver halide emulsion of claim 8 having dispersed therein finely divided particles containing at least one coupler compound and a permanent coupler solvent selected from the group consisting of pentaerythritol tetrabenzoate; 1,2,2,3- tetracarbethoxy propane; pentaerythritol tetralaurate; tris (2,2,4-trimethylpentyl)trimellitate; 1,2,4-benzenetricarboxylic acid, tris (Z-ethylhexyl) ester; 2,2,4- trimethyl-l,3-pentanediol isobutyrate, and a 2,2,4- trimethylpentanediol-1,3-adipic acid polyester terminated with isobutyric acid.
  • a permanent coupler solvent selected from the group consisting of pentaerythritol tetrabenzoate; 1,2,2,3- tetracarbethoxy propane; pen
  • a color photographic element comprising a support and at least one light-sensitive photographic silver halide emulsion layer applied thereto, said emulsion layer having dispersed therein finely divided particles containing a coupler compound in a solvent system comprising at least one compound of the formulae R" and R"" are individually defined at each occurrence as a hydrogen atom or a lower alkyl group;
  • R is defined as an arylcarbonyl group or an alkylcarbonyl group
  • R is defined as an alkoxy carbonyl group having up to 15 carbon atoms and n is an integer of 1-1000.
  • a color photographic element of claim 19 wherein the coupler compound is a phenolic-or a-naphtholic-cyan dye-forming coupler.
  • a color photographic element of claim 19 wherein the coupler compound is an open chain ketomethylene yellow dye-forming coupler.
  • a color photographic element of claim 19 wherein the coupler compound is a S-pyrazolone magenta dye-forming coupler.
  • a color photographic element comprising a support and at least one light sensitive photographic silver halide emulsion layer applied thereto, said emulsion layer having dispersed therein finely divided particles containing a coupler compound in a solvent system comprising at least one compound of the formulae R'-R" are individually defined at each occurrence as a hydrogen atom or an alkyl group of one to eight carbon atoms; and R" is a phenyl carbonyl group or an alkyl carbonyl group of two to 13 carbon atoms.
  • a color photographic element comprising a support and at least one light sensitive photographic silver halide emulsion layer applied thereto, said emulsion layer having dispersed therein finely divided particles containing a coupler compound in a solvent system comprising at least one compound of the formulae R is defined as an alkoxy carbonyl group of two to 15 carbon atoms.
  • a color photographic element comprising a support layer and at least one light sensitive photographic silver halide emulsion layer applied thereto, said emulsion layer having dispersed therein finely divided particles containing at least one coupler compound and a permanent coupler solvent selected from the group I CH I ilIl wherein R'R and R"" are individually defined at each occurrence as a hydrogen atom or an alkyl group of one, to eight carbon atoms; and
  • n is an integer of l-lOOO.
  • a color photographic element comprising a support and at least one light sensitive photographic silver halide emulsion layer applied thereto, said emulsion layer having dispersed therein finely divided particles containing a coupler compound in a solvent system comprising at least one compound of the formula consisting of pentaerythritol tetrabenzoate; l,2,2,3-

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US00285288A 1972-08-31 1972-08-31 Silver halide emulsions containing coupler solvents Expired - Lifetime US3779765A (en)

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CA (1) CA1006032A (enrdf_load_stackoverflow)
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GB (1) GB1439052A (enrdf_load_stackoverflow)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50140126A (enrdf_load_stackoverflow) * 1974-04-26 1975-11-10
JPS5126037A (ja) * 1974-08-28 1976-03-03 Mitsubishi Paper Mills Ltd Karaashashinzairyo
US4003748A (en) * 1974-03-07 1977-01-18 Agfa-Gevaert, A.G. Incorporation process
US4004928A (en) * 1974-08-28 1977-01-25 Mitsubishi Paper Mills, Ltd. Color photographic material
US4430422A (en) 1982-01-26 1984-02-07 Agfa-Gevaert, N.V. Method of dispersing photographic adjuvants in a hydrophilic colloid composition
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4684606A (en) * 1985-12-24 1987-08-04 Eastman Kodak Company Sterically hindered photographic coupler solvents and photographic elements employing same
US4728599A (en) * 1985-12-02 1988-03-01 Eastman Kodak Company Sterically hindered phenolic ester photographic coupler dispersion addenda and photographic elements employing same
DE3700570A1 (de) * 1987-01-10 1988-07-21 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial
EP0289820A1 (en) * 1987-05-08 1988-11-09 Minnesota Mining And Manufacturing Company Light-sensitive silver halide photographic materials and process for incorporating hydrophobic photographic additives into hydrophilic colloid compositions
US4827019A (en) * 1985-12-24 1989-05-02 Eastman Kodak Company Sterically hindered aromatic carboxylic esters
EP0357069A3 (en) * 1988-09-01 1990-09-05 Eastman Kodak Company Color photographic elements with polymeric couplers
US5162197A (en) * 1988-02-29 1992-11-10 Fuji Photo Film Co., Ltd. Silver halide photographic material
EP0711804A2 (de) 1994-11-14 1996-05-15 Ciba-Geigy Ag Kryptolichtschutzmittel

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4916050A (en) * 1987-05-26 1990-04-10 Konica Corporation Silver halide light-sensitive photographic material

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287134A (en) * 1964-03-09 1966-11-22 Du Pont Photgraphic layers and their preparation
US3409439A (en) * 1964-02-01 1968-11-05 Fuji Photo Film Co Ltd Color photographic materials
US3413123A (en) * 1964-08-20 1968-11-26 Agfa Gevaert Ag Gelatine compositions containing alkylene oxide hydrophobic plasticizers
US3554755A (en) * 1966-11-17 1971-01-12 Ferrania Spa Photographic emulsions containing chemical adjuvants dispersed in crystalloidal solvents
US3676141A (en) * 1968-08-22 1972-07-11 Fuji Photo Film Co Ltd Process for the preparation of color-photographic sensitive materials using nonionic and anionic surface active agents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409439A (en) * 1964-02-01 1968-11-05 Fuji Photo Film Co Ltd Color photographic materials
US3287134A (en) * 1964-03-09 1966-11-22 Du Pont Photgraphic layers and their preparation
US3413123A (en) * 1964-08-20 1968-11-26 Agfa Gevaert Ag Gelatine compositions containing alkylene oxide hydrophobic plasticizers
US3554755A (en) * 1966-11-17 1971-01-12 Ferrania Spa Photographic emulsions containing chemical adjuvants dispersed in crystalloidal solvents
US3676141A (en) * 1968-08-22 1972-07-11 Fuji Photo Film Co Ltd Process for the preparation of color-photographic sensitive materials using nonionic and anionic surface active agents

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4003748A (en) * 1974-03-07 1977-01-18 Agfa-Gevaert, A.G. Incorporation process
JPS50140126A (enrdf_load_stackoverflow) * 1974-04-26 1975-11-10
JPS5126037A (ja) * 1974-08-28 1976-03-03 Mitsubishi Paper Mills Ltd Karaashashinzairyo
US4004928A (en) * 1974-08-28 1977-01-25 Mitsubishi Paper Mills, Ltd. Color photographic material
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4430422A (en) 1982-01-26 1984-02-07 Agfa-Gevaert, N.V. Method of dispersing photographic adjuvants in a hydrophilic colloid composition
US4728599A (en) * 1985-12-02 1988-03-01 Eastman Kodak Company Sterically hindered phenolic ester photographic coupler dispersion addenda and photographic elements employing same
US4827019A (en) * 1985-12-24 1989-05-02 Eastman Kodak Company Sterically hindered aromatic carboxylic esters
US4684606A (en) * 1985-12-24 1987-08-04 Eastman Kodak Company Sterically hindered photographic coupler solvents and photographic elements employing same
DE3700570A1 (de) * 1987-01-10 1988-07-21 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial
EP0289820A1 (en) * 1987-05-08 1988-11-09 Minnesota Mining And Manufacturing Company Light-sensitive silver halide photographic materials and process for incorporating hydrophobic photographic additives into hydrophilic colloid compositions
US4873182A (en) * 1987-05-08 1989-10-10 Minnesota Mining And Manufacturing Company Light-sensitive silver halide photographic materials and process for incorporating hydrophobic photographic additives into hydrophilic colloid compositions
JP2612898B2 (ja) 1987-05-08 1997-05-21 ミネソタ マイニング アンド マニユフアクチユアリング カンパニー 感光性ハロゲン化銀写真材料
US5162197A (en) * 1988-02-29 1992-11-10 Fuji Photo Film Co., Ltd. Silver halide photographic material
EP0357069A3 (en) * 1988-09-01 1990-09-05 Eastman Kodak Company Color photographic elements with polymeric couplers
EP0711804A2 (de) 1994-11-14 1996-05-15 Ciba-Geigy Ag Kryptolichtschutzmittel

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Publication number Publication date
GB1439052A (en) 1976-06-09
FR2198177B1 (enrdf_load_stackoverflow) 1977-05-13
FR2198177A1 (enrdf_load_stackoverflow) 1974-03-29
CA1006032A (en) 1977-03-01

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