US3576635A - Light-sensitive silver halide color-photographic material - Google Patents

Light-sensitive silver halide color-photographic material Download PDF

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Publication number
US3576635A
US3576635A US714976A US3576635DA US3576635A US 3576635 A US3576635 A US 3576635A US 714976 A US714976 A US 714976A US 3576635D A US3576635D A US 3576635DA US 3576635 A US3576635 A US 3576635A
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United States
Prior art keywords
color
light
coupler
silver halide
photographic material
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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
US714976A
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English (en)
Inventor
Kenro Sakamoto
Teruo Hanzawa
Isabro Inoue
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.)
Konica Minolta Inc
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Konica Minolta Inc
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Publication date
Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc
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Publication of US3576635A publication Critical patent/US3576635A/en
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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
    • G03C7/32—Colour coupling substances
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore

Definitions

  • a light-sensitive silver halide color-photographic material incorporated with a novel magenta coupler compound of the general formula This invention relates to a light-sensitive silver halide color-photographic material, characterized by that it contains a new magenta coupler of the general formula wherein X is C -C alkyl or alkoxy, or halogen atom; R is an aliphatic hydrocarbon radical of 12 to 30 carbon atoms; and M is hydrogen, alkali metal or ammonium group. 7
  • Yellow, magenta and cyan colored images which constitute a color-photographic image have undesired absorptions at the spectral regions of green light, blue-red light and blue-green light, respectively.
  • a magenta image has undesired absorption particularly at the spectral region of blue light, and so, it is necessary to have a yellowcolored coupler incorporated in a green-sensitive emulsion layer which can yield a magenta image upon color development, while a yellow positive image (i.e. yellow masking image) is formed by the action of unreacted coupler, thereby to corroborate undesired absorption of the magenta image at the spectral region of blue light.
  • a colored magenta coupler which can provide such masking eifect as above and which is usable in commercial practice should fulfill the following requirements:
  • magenta coupler has a good dispersibility in a silver halide emulsion
  • magenta coupler can be produced in pure form and in low cost from a readily available starting material.
  • HON N(
  • J-NHCO-C15Har 0: N H OaNa H0g N N(:J- IE NHC 0-017113; f
  • a colored magenta coupler used in a light-sensitive SOa & photographic material of this invention is substantially free from the above-mentioned drawbacks.
  • Precipitate formed is filtered off and Washed with a solution of 10 g. of sodium acetate, 50 ml. of ethyl alcohol and 50 ml. of water and then with 100 ml. of ethyl alcohol, and dried.
  • 3.4 g. of orange-yellow powder decomposing at above 320 C. were obtained after recrystallizing twice from 75% of ethyl alcohol.
  • the light-sensitive material of this invention is prepared by dissolving a color magenta coupler of the aforesaid general formula in an aqueous or alcoholic solution of caustic alkali or alkali carbonate, dispersing the resulting solution in a green-sensitized silved halide emulsion and applying the resulted dispersion on film base and then drying.
  • An amount of the coupler added varies with the sort of a silver halide emulsion as well as the sort of a coupler used.
  • Preferable amount of a coupler is 1-50 g. per 1 mol of silver halide emulsion and more or less amount may be acceptable.
  • Magenta color negative image of good spectral absorption and yellow masking image resulting from unreacted coupler are formed simultaneously, when a silver halide emulsion layer containing color magenta couplers is subjected to light-exposure and then treated with a devolping bath comprising p-phenylenediamine as a devolping agent, bleached, fixed and dried.
  • Any color developers are commonly used for development of color-photographic materials of this invention.
  • the colored magenta coupler used in this invention has the better water solubility than the 'known coupler has. Because of this, the magenta coupler of this invention is improved in dispersibility in a silver halide photographic emulsion so that it can produce a highly transparent photographic film. Further, the film produced has a high photographic sensitivity even in the conventionally known color development, with the formation of a magenta color negative image having little absorption at the spectral region of red light. Further, a very stable masking effect can be obtained, since the spectral absorption characteristic of the yellow masking image is little influenced by the color development. Thus, the colored magenta coupler of this invention which has many advantageous features as mentioned above is very useful in' a light-sensitive color-photographic material.
  • EXAMPLE 1 One gram of each of the couplers -(1), (3), (4) and (6) are dissolved respectively in ml. each of 1 N KOH aqueous solution. Each of respective solutions is diluted with water to make up 30 ml. and then dispersed into 100 ml. of a green-sensitive silver halide emulsion. The resulting dispersion is adjusted to pH 6.8 with an aqueous citric acid and then coated on a film base and dried. The thus prepared photographic films are used as test samples.
  • the known couplers [I] and [IH] are individually used for the preparation of photographic films which are control samples. These samples are subjected to exposure to light through an optical wedge and then treated at 20 C. for 10 minutes with a developing solution of the following formulation:
  • the films are washed with water for 10 minutes and then treated for 5 minutes with a fixing solution of the following formulation:
  • the films are then washed with water for 20-25 minutes and dried.
  • the films now have a magenta color negative image and an yellow masking image.
  • photographic speed and absorption maximum of the masking image and magenta color negative image are measured. The results are set forth in Table 2.
  • the photographic film containing the magenta coupler of the present invention is highly ex- 8 cellent in photographic speed and has less red absorption when compared with the film containing the known magenta coupler.
  • EXAMPLE 2 Two photographic films which are test samples are prepared by using one gram of each of the couplers (l) and (6) in the same manner as in Example 1. These films are subjected to sensitometric exposure and color development in the same manner as in Example 1. The films now have a yellow masking image and a magenta color negative image. The density of the masking image of the unexposed portion when said density is measured through a blue filter (absorption maximum at 535 m is expressed as D'B. Separately, the corresponding unexposed film are treated for 5 minutes with a fixing solution containing 250 g. of sodium thiosulfate in 1000 ml. of water and then washed with water and dried. The density of the resulting image is measured as DB. The value of D'B is expressed as an index of DB which is rated as 100. As a control sample, a photographic film containing the known coupler [III] is employed. The results are set forth in Table 3.
  • the thus obtained photographic film has a high speed and can yield, simultaneously by color development, a magenta color negative image having good spectral absorption characteristics and a yellow positive masking image having adequate gradient.
  • a light-sensitive silver halide color-photographic material characterized by that it contains a magenta coupler of the general formula wherein X is C C alkyl or alkoxy group or halogen 10 2.
  • Alight-sensitive silver halide color-photographic mamaterial as claimed in claim 1, wherein said magenta terial as claimed in claim 1, wherein said magenta coupler coupler is a compound of the structural formula is a compound of the structural formula I HO N N(]-
  • a light-sensitive silver halide color-photographic material as claimed in claim 1, wherein said magenta coupler SO Na is a compound of the structural formula 3 H I HON N '3(
  • JNHCOC11H11 o '1 1% S OaNa ⁇ N/ CHa-O Cl SOzN8 5.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US714976A 1967-03-23 1968-03-21 Light-sensitive silver halide color-photographic material Expired - Lifetime US3576635A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1786167 1967-03-23

Publications (1)

Publication Number Publication Date
US3576635A true US3576635A (en) 1971-04-27

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US714976A Expired - Lifetime US3576635A (en) 1967-03-23 1968-03-21 Light-sensitive silver halide color-photographic material

Country Status (5)

Country Link
US (1) US3576635A (en:Method)
BE (1) BE712617A (en:Method)
DE (1) DE1770014A1 (en:Method)
FR (1) FR1558164A (en:Method)
GB (1) GB1194762A (en:Method)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4070191A (en) * 1973-03-31 1978-01-24 Konishiroku Photo Industry Co., Ltd. Silver halide emulsion containing colored magenta coupler for photography
US4163670A (en) * 1973-04-21 1979-08-07 Fuji Photo Film Co., Ltd. Color photographic material
US5241058A (en) * 1990-05-29 1993-08-31 Agfa-Gevaert Aktiengesellschaft Azo dye salts useful as masking couplers and preparation thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS557702A (en) * 1978-06-01 1980-01-19 Konishiroku Photo Ind Co Ltd Silver halide color photographic material
US6010839A (en) * 1998-06-26 2000-01-04 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers
US6132943A (en) * 1999-10-14 2000-10-17 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4070191A (en) * 1973-03-31 1978-01-24 Konishiroku Photo Industry Co., Ltd. Silver halide emulsion containing colored magenta coupler for photography
US4163670A (en) * 1973-04-21 1979-08-07 Fuji Photo Film Co., Ltd. Color photographic material
US5241058A (en) * 1990-05-29 1993-08-31 Agfa-Gevaert Aktiengesellschaft Azo dye salts useful as masking couplers and preparation thereof

Also Published As

Publication number Publication date
FR1558164A (en:Method) 1969-02-21
GB1194762A (en) 1970-06-10
DE1770014A1 (de) 1972-04-13
BE712617A (en:Method) 1968-07-31

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