US2373821A - Production of color photographic images - Google Patents

Production of color photographic images Download PDF

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Publication number
US2373821A
US2373821A US431272A US43127242A US2373821A US 2373821 A US2373821 A US 2373821A US 431272 A US431272 A US 431272A US 43127242 A US43127242 A US 43127242A US 2373821 A US2373821 A US 2373821A
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United States
Prior art keywords
color
phenol
radical
images
production
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Expired - Lifetime
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US431272A
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English (en)
Inventor
Frohlich Alfred
Schneider Wilhelm
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GAF Chemicals Corp
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General Aniline and Film Corp
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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
    • G03C7/34—Couplers containing phenols
    • G03C7/344—Naphtholic couplers

Definitions

  • the present invention relates to the produc-' .tion of color photographic .images and in particular of images obtained by color forming development. II
  • the present invention is based on the observation that dyestufi formers yielding quinoneimine dyestuiis which exhibit an especially high absorption in the short wave infra-red and hence satisfy the requirements of the negative process as to the spectral properties of the dyestuffs to a large extentand are moreover suitable for the urposesof sound recording owing to the high absorption in the long wave red can be produced by using as dyestufi formers condensable aromatic "hydroxy compounds containing in theirmolecule a 5 -membered heterocyclic nucleus.
  • radicals which are especially favorable for photographic purposes as, for instance, nondiflusing radicals and groupsrenderi'ng the components soluble indiluted alkalies. ,Owing to the I easy introduction of several substituents it is also I possible to' influence the color tone in any desired manner.
  • the heterocyclic nucleus may be a free sub- "stituent as, ,for instance, the 5-membered ring in the condensation product from u-hydroxynaphthoic acid and nitroaminobenzthia'zole corre- I spending with the followingformula 1-hydroxy-2-naphthoyl-5'-nitro-2-amino benz 40 thiazole) and in the product obtained by condensing u -hydroxynaphthoic acid with o-am'inophenol and heating the reaction product to split oil water and having the following formula:
  • the heterocyclic nucleus may also directly be fused on the phenol or naphthol capable of coupling as, for instance, in hydroxynaphthylamino- I phenylthiazole sulionic acid of the following formula:
  • the preferred compounds. according to the present invention are salts of phenols having joined thereto in ortho position to the phenolic hydroxyl group a radical such as a benzthiazole, a benzoxazole or a benzimidaaole, the carbon atom between the heteroatoms of the flve-membered ring of such heterocyclic radical being linked to the phenol through a nuclear carbon to carbon linkage and said salt having linked thereto a radical rendering, the salt fast to diflusion in gelatin. Examples of such compounds are given above.
  • non-diflusing dyestui! formers may be cast to form single layers or worked up into multilayer materials containing the several emulsion layers on one or bothsides of the support and, if necessary, filter layers,intermediate layers or anti-halation layers.
  • Example Y 4 Into l-hydroxynaphthyl-5.6-3' sminophenylthiazole-2-sulfonic acid prepared in themanner described in German Patent 165,126 a radical preventing difl'usion may be introduccd'by reacting the dyestui! component with stearlc acid chloride or abietic acid chloride or perhydrodiphenylcarbonylic acid chloride. Owing to the presence of the suite group the non-diffusing solubility.
  • the curve i represents the absorption curve of the dyestufl formed from 1-hydroxy- 2' naphthyl- 2 -benzimidazole -4'-sulfonic acid and p-dimethylaminoaniline and the curve 2 the absorption curve of the dyestufi formed from l'-hydroxy-2'-naphthyl-2-benzoxazole and p-dimethylaminoaniline.
  • the curves 3 and 5 repre- .sent the absorption'ourves of the dyestuffs from the known dyestufl formers a'-naphthol and 2.4- dibromonaphthol respectively.
  • the absorption curve I is that of the dyestufi from l-hydroxynaphthyl-5.6-3'*-aminophenylthiazole-2-sulfonic acid whereas the.
  • curves 2 and 3 are the absorption curves of the dyestufls from nz-naphthol and 2.4-dibromonaphthol respectively.
  • the improvement which comprises developing an exposed silver halide emulsion with an aromatic primary amino developer in the presence of a i water-soluble saltggof a phenol having joined thereto in ortho position to the phenolic hydroxyl group a radical selected from the class consisting of benzthiazole, benzoxazole' and benzimidazole radicals, the carbon atom between the hetero atoms of the flve-membered ring of said radical being linked to said phenol through a nuclear carbon to carbonlinkage.
  • the improvement which comprises developing an exposed photographic silver halide emulsion with an aromatic primary amino developer containing in ortho position to the phenolic hydroxyl group a radical selected from the classconsisting of benzthiazole, benzoxazole and benzimidazole-radicals, the carbon atom between the hetero atoms ot'the nve-membered ring of said radicalbei'ng linked to said phenol through a nuclear carbon 9 to carbon linkage.
  • the improvement which comprises developing with an aromatic primary-amino developer, a silver halide emulsion containing a soluble salt of a phenol having joined thereto in ortho position to the phenolic hydroxyl group a'radical selected from the class consisting of benzthiazole, benzoxazole andibensimidasole radicals, the carbon atom between-the hetero atoms of the flve-membered ring or said radical, being linked to said phenol through a nuclear carbon to carbon linkage.
  • a silver halide gelatin emulsion for color i'orming development containing a soluble salt of a phenol having joined thereto in ortho positionto the phenolic hydroxyl; groupa radical se- I lected from the class consisting of. benzthi'azole, benzoxazole and benzimidazole radicals, the carbon atom between thehetero atoms of the fivemembered ring of said radical being linked to" said phenol through a linkage.
  • a color forming developer comprising an aqueous solution containing an aromatic primary amino developing agent and a solubielsalt' of a nuclear carbon to carbon phenol having joined thereto in ortho position to the phenolic hydroxyl group aradical selected from the class consisting of benzthiazole, benzoxazole andbenzimidazole radicals, the carbon atom between the hetero atoms of the five-membered ring of said radical being linked to said phenol through a nuclear carbon to carbon linkage.
  • the-improvement which comprises developing an exposed silver halide emulsion with an aromatic primary amino developer in the presence of a salt of a phenol havingjoinedthereto in ortho position to the phenolic hydroxyl group aradicalselected from the class consisting of benzthiazoie, benzo'xazole and benzimidazole radicals, thecarbon atom between the hetero atoms of the flve membered ring of said radical being linked to said phenol through a nuclear carbon to-carbon linkage, said salt having joined thereto a radical rendering the salt fast to diflusion,
  • a silver halide emulsion for color-forming development containing a'compound of the following constitution:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US431272A 1940-10-19 1942-02-17 Production of color photographic images Expired - Lifetime US2373821A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI0068058 1940-10-19

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US2373821A true US2373821A (en) 1945-04-17

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US (1) US2373821A (enrdf_load_stackoverflow)
BE (1) BE443157A (enrdf_load_stackoverflow)
CH (3) CH231844A (enrdf_load_stackoverflow)
FR (1) FR881899A (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2500487A (en) * 1948-11-09 1950-03-14 Gen Aniline & Film Corp Yellow diffusion-fast color formers of the benzimidazole class
US2530349A (en) * 1947-04-30 1950-11-14 Gen Aniline & Film Corp Cyan color formers capable of yielding fine grain images
US2545687A (en) * 1947-04-30 1951-03-20 Gen Aniline & Film Corp N-substituted benzimidazoles
US3056705A (en) * 1958-06-19 1962-10-02 Owens Corning Fiberglass Corp Surface treated glass and similar fibers
US4178183A (en) * 1978-07-27 1979-12-11 Eastman Kodak Company Thiazolyl coupler compositions and photographic elements suited to forming integral sound tracks
US4208210A (en) * 1974-12-19 1980-06-17 Fuji Photo Film Co., Ltd. Process for forming an optical soundtrack
US4233389A (en) * 1979-07-23 1980-11-11 Eastman Kodak Company Fluorinated 1-hydroxy-2-naphthamide coupler compositions and photographic elements suited to forming integral sound tracks
US4250251A (en) * 1978-07-27 1981-02-10 Eastman Kodak Company Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US5030544A (en) * 1984-09-28 1991-07-09 Agfa-Gevaert, N.V. Photographic elements comprising thiazolyl couplers capable of forming infrared-absorbing dyes for integral sound track
WO2001050192A1 (en) * 1999-12-31 2001-07-12 Applied Science Fiction, Inc. Digital film processing method

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2530349A (en) * 1947-04-30 1950-11-14 Gen Aniline & Film Corp Cyan color formers capable of yielding fine grain images
US2545687A (en) * 1947-04-30 1951-03-20 Gen Aniline & Film Corp N-substituted benzimidazoles
US2500487A (en) * 1948-11-09 1950-03-14 Gen Aniline & Film Corp Yellow diffusion-fast color formers of the benzimidazole class
US3056705A (en) * 1958-06-19 1962-10-02 Owens Corning Fiberglass Corp Surface treated glass and similar fibers
US4208210A (en) * 1974-12-19 1980-06-17 Fuji Photo Film Co., Ltd. Process for forming an optical soundtrack
US4178183A (en) * 1978-07-27 1979-12-11 Eastman Kodak Company Thiazolyl coupler compositions and photographic elements suited to forming integral sound tracks
US4250251A (en) * 1978-07-27 1981-02-10 Eastman Kodak Company Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US4233389A (en) * 1979-07-23 1980-11-11 Eastman Kodak Company Fluorinated 1-hydroxy-2-naphthamide coupler compositions and photographic elements suited to forming integral sound tracks
US5030544A (en) * 1984-09-28 1991-07-09 Agfa-Gevaert, N.V. Photographic elements comprising thiazolyl couplers capable of forming infrared-absorbing dyes for integral sound track
WO2001050192A1 (en) * 1999-12-31 2001-07-12 Applied Science Fiction, Inc. Digital film processing method
US20020080409A1 (en) * 1999-12-31 2002-06-27 Keyes Michael P. Digital film processing method
US6664034B2 (en) 1999-12-31 2003-12-16 Eastman Kodak Company Digital film processing method
US20040053175A1 (en) * 1999-12-31 2004-03-18 Keyes Michael P. Digital film processing method
US6824966B2 (en) 1999-12-31 2004-11-30 Eastman Kodak Company Digital film processing method
US20050008981A1 (en) * 1999-12-31 2005-01-13 Keyes Michael P. Digital film processing method
US6910816B2 (en) 1999-12-31 2005-06-28 Eastman Kodak Company Digital film processing method

Also Published As

Publication number Publication date
CH234044A (de) 1944-08-31
CH226702A (de) 1943-04-30
BE443157A (enrdf_load_stackoverflow) 1941-11-29
FR881899A (fr) 1943-05-11
CH231844A (de) 1944-04-15

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