US2186045A - Production of color photographic pictures - Google Patents

Production of color photographic pictures Download PDF

Info

Publication number
US2186045A
US2186045A US254235A US25423539A US2186045A US 2186045 A US2186045 A US 2186045A US 254235 A US254235 A US 254235A US 25423539 A US25423539 A US 25423539A US 2186045 A US2186045 A US 2186045A
Authority
US
United States
Prior art keywords
photographic
silver halide
acid
production
indolinone
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
US254235A
Other languages
English (en)
Inventor
Schneider Wilhelm
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.)
GAF Chemicals Corp
Original Assignee
Agfa Ansco Corp
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
Application filed by Agfa Ansco Corp filed Critical Agfa Ansco Corp
Application granted granted Critical
Publication of US2186045A publication Critical patent/US2186045A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/381—Heterocyclic compounds
    • G03C7/3815—Heterocyclic compounds with one heterocyclic ring

Definitions

  • My present invention relates to the production of color photographic pictures.
  • a further object of this invention is to provide a photographic material one emulsion layer of which contains a-indolinone as the dyestufi component. Another object is the provision of a photographic material which comprises .an emulsion layer containing a-indolinone substituted at the nitrogen atom.
  • Yet another object is to provide a photographic material comprising an emulsion layer which contains a-indolinone substituted in the benzene nucleus.
  • a still further object is to provide a photo- Q graphic material having an emulsion layer which contains a-indolinone substituted by 'alkyl droxy groups or nitro groups.
  • Yet another object is the provision of a photogroups, alkoxy groups, aryl groups,'halogen, hy-
  • the groups which impart fastness to diffusion may be introduced, for example, by the methods described in the U. S. Patents 2,179,238, 2,178,612 and 2,179,244 and 'U. S. Patent applications 94,340 filed August 5, 1936, 159,518 filed August 17, 1937, 164,499 filed September 18, 1937, 166,832 filed October 1, 1937, 171,705 filed October 29, 1937, 175,285 filed November 18, 1937, 176,058 filed November 23, 1937 and 191,952 filed February 23, 1938.
  • the last named application describes components which contain in addition to a group rendering the component fast to diffusion a solubilizing group such as a carboxy group.
  • the components are prepared by reacting the internal anhydride of apolybasic organic acid, such as the anhydrides of maleic acid, succinic acid, pyro-tartaric acid and the like containing for example a long aliphatic chain 1. e. of at least 5 carbon atoms such as octadecylene, isodecylene, iso-nonylene and the like with a color former containing a reactive group such as an aminoor hydroxy group.
  • the ring of the anhydride is thereby split in such a manner that one C0- group'units with the reactive group and the other forms a 'carboxy group.
  • the color former there may be used p-amino-aceto-acetic' anilide, 4 q amino 1-phenyl-3-methyl-5-pyrazolone,- 1- amiho-S-naphthol .and the like.
  • the. anhydride there may be used octadecylene succinic acid anhydride, u-dodecyl-m-hexahydrobenzenepyro-tartaric acid anhydride and the like.
  • nitrogen atom of a-indolinone may carry a radicle prescribed in one or other of the foregoing applications, for instance an undecyl group. Furthermore, as described in the speciflcation of the U. S. Patent application Ser. No.
  • the molecule of the dyestufi component maybe in the form of a chain.
  • radicles lending fastness to diffusion may be introduced in known manner, for example, by
  • the photographic emulsions having different dyestuif components may be distributed in particles on a support. With the aid of this material screen pictures may be made.
  • the silver halide emulsion layers provided with layers being sensitized for differentregions of the dyestuif components may be combined with NH N Ali-111a:
  • the dyestufl component is produced in following manner: d-indolinone is dissolved in concentrated 4 sulfuric acid and nitrated by addition of 1 mol of sodium nitrate with cooling. The reaction product is precipitated by pouring out the mixture on ice and after recrystallizing from water is reduced with stannous chloride and hydrochloric acid. The tin is removed with hydrogen sulfide and the whole is concentrated by evaporation. The reaction product is then acylated with 1 moi of oleic acid chloride in pyr i e. After 7 sulfonation with sulfuric acid containing 30 per cent S0; with cooling a product easily soluble in water is obtained. This dyestufl component is then dissolved in a solution of sodium carbonate and added to a silver halide emulsion.
  • Example 2 A of the 'followmg formula may be Q incorporated in a photographic layer: I i
  • Example 4 1 mol of fi-alninO-a-lndOllIlOIle produced in the manner described in Example 1 is reacted with 1 mol of abietic acid chloride.
  • the product thus obtained of the following formula 0 NH N lo emetic acldradicle is dissolved in methanol and added to a photographic emulsion.
  • a photographic multi-layer material comprising at least one silver halide gelatin emulsion layer containing a compound selected from the class of a-indolinone and substituted aindolinone,-said compound containing inits U molecule a group capable of making said compound fast to diffusion in gelatin.
  • a photographic multi-layer material comprising at least one silver halide emulsion layer containing a compound of the formula ll prising at least one silver halide emulsion layer containing a compound of the formula C1a a1 '7.
  • a photographic multi-layer material comprising at least one silver halide emulsion layer containing a compound of the formula 8.
  • the photographic silver halide emulsion defined in claim 2 wherein the group capable of making said compounds fast to diffusion is an aliphatic radicle of high molecular weight.
  • the photographic silver halide emulsion deflnedin claim 2 wherein the group capable of making said compounds fast to diffusion is an aliphatic radicle of high molecular weight which is linked to the indolinone nucleus by a linkage selected from the class consisting of a direct carbon to direct nuclear carbon linkage, an ester linkage and an acid amide linkage.
  • the photographic silver halide emulsion defined in claim 2 wherein the group capable of making said compounds fast to difiusion is an aliphatic radicle containing from 18 to, 22 carbon atoms and having a solubilizing group selected from the class consisting of 'sulfonic acid and carboxylic acid groups.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US254235A 1938-02-05 1939-02-02 Production of color photographic pictures Expired - Lifetime US2186045A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI0060443 1938-02-05

Publications (1)

Publication Number Publication Date
US2186045A true US2186045A (en) 1940-01-09

Family

ID=7195236

Family Applications (1)

Application Number Title Priority Date Filing Date
US254235A Expired - Lifetime US2186045A (en) 1938-02-05 1939-02-02 Production of color photographic pictures

Country Status (4)

Country Link
US (1) US2186045A (en))
BE (1) BE432544A (en))
CH (1) CH232384A (en))
FR (1) FR849861A (en))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3199983A (en) * 1961-02-01 1965-08-10 Agfa Ag 3-indazolone color couplers
US5573892A (en) * 1994-11-04 1996-11-12 Agfa-Gevaert Ag Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2829975A (en) * 1956-04-26 1958-04-08 Gen Aniline & Film Corp 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
BE561850A (en)) * 1956-10-23

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3199983A (en) * 1961-02-01 1965-08-10 Agfa Ag 3-indazolone color couplers
US5573892A (en) * 1994-11-04 1996-11-12 Agfa-Gevaert Ag Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process

Also Published As

Publication number Publication date
BE432544A (en))
FR849861A (fr) 1939-12-04
CH232384A (de) 1944-05-31

Similar Documents

Publication Publication Date Title
CA1225270A (en) Silver halide color photographic material
JPS5912169B2 (ja) ハロゲン化銀カラ−感光材料
US4009035A (en) Process for forming cyan dye photographic images
US3002836A (en) Cyan color former for color photography
JPS60205447A (ja) ハロゲン化銀写真感光材料
US3938995A (en) Silver halide color photographic element and process containing leuco dyes
US2186045A (en) Production of color photographic pictures
US4501898A (en) Photographic development inhibitor (1H- or 2H-) indazolyl hydroquinone derivatives
US4012258A (en) Process for forming color photographic images
US3551155A (en) Light sensitive silver halide materials containing yellow-forming couplers
JPS62134642A (ja) 写真要素
US3876428A (en) Multilayer silver halide material containing a white coupler
US2186736A (en) Coupling compounds for color forming development
US2357395A (en) Photographic emulsion
US3684514A (en) Light-sensitive silver halide color photographic emulsions
US2357394A (en) Photographic emulsion
US4871652A (en) Photographic silver halide material and process
JPH06504536A (ja) カラーカップラーとしての活性化プロペン及びその製造方法
US2154918A (en) Coupling compounds for color forming development
JPH04124661A (ja) ハロゲン化銀カラー写真感光材料
US2536010A (en) Preparation of azine dyestuff images
US2376679A (en) Production of color photographic images
US3888680A (en) Light-sensitive silver halide color photographic material containing bis-pyrazolone couplers
US2186733A (en) Color photography
US3849140A (en) Diffusion-resistant dispersible yellow couplers for the production of photographic color images