US3832386A - Color photographic material - Google Patents

Color photographic material Download PDF

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Publication number
US3832386A
US3832386A US00143241A US14324171A US3832386A US 3832386 A US3832386 A US 3832386A US 00143241 A US00143241 A US 00143241A US 14324171 A US14324171 A US 14324171A US 3832386 A US3832386 A US 3832386A
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US
United States
Prior art keywords
coupler
group
color photographic
couplers
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
US00143241A
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English (en)
Inventor
I Inoue
T Hanzawa
T Endo
H Deguchi
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.)
KANISHIROKU PHOTO IND CO Ltd
KANISHIROKU PHOTO IND CO Ltd JA
Original Assignee
KANISHIROKU PHOTO IND CO Ltd
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Publication of US3832386A publication Critical patent/US3832386A/en
Assigned to KONICA CORPORATION reassignment KONICA CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: KONISAIROKU PHOTO INDUSTRY CO., LTD.
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Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • 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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/362—Benzoyl-acetanilide couplers

Definitions

  • the coupler has the general formula I X I (camcQ-c oomooNHQ wherein X is hydrogen, halogen, a lower alkoxy group, a lower alkyl group or an aryloxy group; and Y is where R is a lower alkyl group; R is a hydrocarbon residue having eight to 18 carbon atoms; and COR is an acyl group having nine to 20 carbon atoms.
  • This invention relates to a light-sensitive color photographic material. More particularly, the invention pertains to a color photographic material containing a yellow color image-forming novel coupler belonging to the so-called protect type coupler. i.e., a waterinsoluble or difficulty water-soluble coupler to be used by dissolving the same in a difficulty water-miscible 1 high boiling solvent and dispersing the resulting solution in a photographic emulsion.
  • the novel yellow coupler is represented by the general formula,
  • X is hydrogen, halogen, a lower alkoxy group, a lower alkyl group or an aryloxy group
  • Y is a group of the formula
  • R is a lower alkyl group
  • R is a hydrocarbon residue having eight to 18 carbon atoms
  • COR- is an acyl group having nine to 20 carbon atoms.
  • the coupler of the aforesaid general formula, which is used in the present invention has a t-butyl group substituted in the p-position of the benzoyl portion, so that it can overcome the abovementioned drawbacks of the conventional couplers and gives such effects that the resulting color image becomes unexpectedly excellent in color reproduction and comes to be improved in stability as well. These effects are considered to be ascribable to the branched tertiary alkyl group in the p-position.
  • the coupler is easily soluble in such a high boiling solvent as di butyl phthalate or tricresyl phosphate, so that the amount of solvent for the coupler can be decreased to give a high concentration dispersion, which is difficultly crystallized in a photographic emulsion or a film formed by coating and drying the emulsion.
  • a high boiling solvent as di butyl phthalate or tricresyl phosphate
  • coupler of the present invention has greatly overcome the drawbacks of the conventional couplers.
  • reaction product was deacetylated by boiling in sodium alcoholate. poured into water, and then acidified with hydrochloric acid to deposit an oily substance. This'oily substance was extracted with ether, and the ether layer was concentrated and subjected to distillation to obtain a fraction of l42l45C/ 3 mm in a yield of 63 percent.
  • the exemplified coupler 2 was obtained from 2-chloro-5-(adodecyloxycarbonyl ethoxycarbonyl) aniline; the exemplified coupler v 3 from 2-phenoxy-5- dodecyloxycarbonyl aniline; the exemplified coupler 4 from 2-methyl-5-myristarnidoaniline; the exemplified coupler 5 from 2-chloro-5-(2,4-di-tertamylphenoxyacetamide) aniline; the exemplified .coupler 6 from 3-(2,4,6-tri-sec-butylphenoxyacetamide) aniline; the exemplified coupler 7 from 2-ethoxy-5-(adi-tert-amylphenoxybutylamide) aniline; the exempli- Table l Excmplificd Melting Nitrogen analysis $7: I
  • the present invention couplers are compared in spectral absorption characteristic of the resulting color images with known couplers, and the value (m;t) is the absorption wave length at an optical density (D) of 0.2, the value of Amax(mp.) is the absorption maximum wave length at an optical density of 1.0,
  • test results showing the fact that the of to 100 g. per mole of silver halide, but may be varied so as to be in conformity to application purposes, without being limited to the above-mentioned range. Further, it is not objectionable to add the coucolor images of photographic materials containing the pler of the present invention to 2 or more of emulsion couplers l, 2 and 3 of the present invention are excellayers of a multi-layered color photographic material. lent in stability are set forth in Table 3, in which the numerals percentages of residual color density.
  • the emulsion used inthe present invention may be 'rABLi'I's T Fading resistance (irra- Moisture resistance (allowdiation with are lamp ing to stand at 50 C. Coupler for 16 hours) 80% RH for 14 days) Known coupler (1,11, 83 96 tCsHnQ-OCHCONH OCH:
  • the coupler, or a mixture of the couplers, of the present invention is dissolved in a high boiling solvent (b.p. 175C. or more) such as tricresyl phosphate or dibutyl phthalate, or in a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
  • a high boiling solvent b.p. 175C. or more
  • tricresyl phosphate or dibutyl phthalate or in a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
  • This solution is mixed with an aqueous gelatine solution containing a surface active agent, and then emulsified by means of a high speed rotary mixer of a colloid mill to form a dispersion.
  • dispersion is directly added to a silver halide photographic emulsion, which is then coated on a support such as glassplate, synthetic resin sheet, resin film base, baryta paper or laminated paper, followed by drying, to prepare a light-sensitive color photographic ln th e above case, the
  • coupler to be added to the photographic emulsion is preferably in the range N-hydroxyethyl-Z-methyl-p-phenylenediamine
  • the emulsion may have been incorporated with any of ordinary photographic additives such as, for example, antifoggant, stabilizers, anti-stain agents, anti-irradiation agents, physical property-improving high molecular additives, hardeners and coating aids. Still further, the emulsion may contain a known carbocyanine or merocyanine dye as an optical sensitizer therefor.
  • a chemical sensitizer e.g., sulfur sensitizer, a natural sensitizer present in gelatine, a reducing sensitizer or a noble metal salt.
  • the emulsion may have been incorporated with any of ordinary photographic additives such as, for example, antifoggant, stabilizers, anti-stain agents, anti-irradiation agents, physical property-improving high molecular additives, hardeners and coating aids.
  • the emulsion may contain a known carbocyanine or merocyanine dye as an optical sensitizer therefor.
  • the thus obtained light-sensitive color photographic material of the present invention is exposed to radioactive rays such as a-rays or B-rays, visible rays or infrared rays, developed with a developer containing a pphenylenediamine type developing agent as a main ingredient, and then bleached, desilvered and fixed to obtain a high density color image which is excellent in spectral absorption characteristic and durability and high in transparency.
  • radioactive rays such as a-rays or B-rays, visible rays or infrared rays
  • a developer containing a pphenylenediamine type developing agent as a main ingredient
  • bleached, desilvered and fixed to obtain a high density color image which is excellent in spectral absorption characteristic and durability and high in transparency.
  • a color photographic material containing the coupler of the present invention is incorporated with an UV-absorber of the benzephenone type (e.g.
  • 2-hydroxy-4- dodecyloxybenzophenone or the triazole type [e.g., 2-( 2-hydroxy-3 ,5 '.-di-tert-butylphenyl) benzotriazole], whereby the resulting color image can further be increased in durability.
  • the triazole type e.g., 2-( 2-hydroxy-3 ,5 '.-di-tert-butylphenyl) benzotriazole
  • Typical examples of the main ingredient of the developer used for development of the present color photographic material are sulfates, sulfites and hydrochlorides of N,N-diethyl-p-phenylenediamine, N-ethyl-N-B- methanesulfonamidoethyl-3-methyl-4-aminoaniline, N-ethyl-N-hydroxyethyl-p-phenylenediamine, N-ethyl- N,N- diethyl-2-methyl-p-phenylenediamine and N,N-diethyl- Z-methyl-p-phenylenediamine.
  • the developer may contain a development-controlling agent such as citrazinic acid, in addition to the above-mentioned main ingredient.
  • Example 1 20.0 Grams of the exemplified to a mixed solution comprising 20 ml. of dibutyl phthalate and 60 ml. of butyl acetate, and the resulting mixture was heated to 60C., whereby the coupler was completely dissolved.
  • the thus formed solution was Alkanol B v(alltylriaphthalenesulfonate, produced by Du Font and 200'rnl..of a Spercent aqueous gelatine coupler l was added
  • the thus prepared photographic material was exposed and then developed at 21C. for 12 minutes with r a developer of the following composition:
  • Example 2 l0 Grams of the exemplified coupler (2) was added to a mixed solution comprising 10 ml. of tricresyl phosphate and 30 ml. of butyl acetate, and the resulting mixture was heated to 50C., whereby the coupler was completely dissolved.
  • the thus formed solution was mixed with 5 ml. of a 10 percent aqueous Alkanol B solution and 800 ml. of a 5 percent aqueous gelatine solution, and the mixture was subjected to a colloid mill to form a dispersion.
  • This coupler dispersion was added to 500 g. of a gelatine silver iodobromide emulsion, which was then coated on a polyester film base and then dried coating film.
  • g Y a gelatine silver iodobromide emulsion
  • the material . was subjected to'sec-. ond exposure by use of a white ligh t gand then developed at 21C; for 3 minutes with adeyelo'per of the following composition: i "1 I N,N-Diethyl2-mcthyl-p-phenylcnediamine Anhydrous sodium sulfite 5 Sodium carbonate (monohydrate) Potassium bromide Water to make Subsequently, the thus treated material'was j to ordinary stopping, water-washing, bleachingandi fix ing treatments, washed with running water for 20 n1 utes and then dried to obtain a yellow positive color image which had an absorption maximum at 455 mp.
  • Example 3 l0 Grams of the exemplified coupler (3) was added to 20 ml. of dibutyl phthalate, and the resulting mixture was heated 'to 50C., whereby the coupler was completely dissolved. The thus formed solution was mixed with 5 ml. of a 10 percent aqueousAlkanol B solution. and 200 ml. of a 5 percent aqueous gelatine. solution,
  • R is a lower alkyl grou ariiifigigfiydibcibon' had an absorption maximum at 445 my. and was excel- I lent, in resistance to light and moisture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00143241A 1970-05-14 1971-05-13 Color photographic material Expired - Lifetime US3832386A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45040492A JPS4917371B1 (2) 1970-05-14 1970-05-14

Publications (1)

Publication Number Publication Date
US3832386A true US3832386A (en) 1974-08-27

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US00143241A Expired - Lifetime US3832386A (en) 1970-05-14 1971-05-13 Color photographic material

Country Status (4)

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US (1) US3832386A (2)
JP (1) JPS4917371B1 (2)
DE (1) DE2123448C3 (2)
GB (1) GB1310627A (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4266019A (en) * 1978-09-13 1981-05-05 Fuji Photo Film Co., Ltd. Silver halide photographic material containing yellow coupler

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644498A (en) * 1963-10-01 1972-02-22 Eastman Kodak Co Yellow dye forming couplers for color photography

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644498A (en) * 1963-10-01 1972-02-22 Eastman Kodak Co Yellow dye forming couplers for color photography

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4266019A (en) * 1978-09-13 1981-05-05 Fuji Photo Film Co., Ltd. Silver halide photographic material containing yellow coupler

Also Published As

Publication number Publication date
DE2123448A1 (2) 1972-04-06
DE2123448B2 (de) 1979-05-10
GB1310627A (en) 1973-03-21
JPS4917371B1 (2) 1974-04-30
DE2123448C3 (de) 1980-01-24

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Date Code Title Description
AS Assignment

Owner name: KONICA CORPORATION, JAPAN

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302

Effective date: 19871021