GB736922A - Improvements in photographic colour couplers - Google Patents

Improvements in photographic colour couplers

Info

Publication number
GB736922A
GB736922A GB17750/53A GB1775053A GB736922A GB 736922 A GB736922 A GB 736922A GB 17750/53 A GB17750/53 A GB 17750/53A GB 1775053 A GB1775053 A GB 1775053A GB 736922 A GB736922 A GB 736922A
Authority
GB
United Kingdom
Prior art keywords
tert
amylphenoxy
prepared
methoxybenzoyl
chloride
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
Application number
GB17750/53A
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.)
Kodak Ltd
Original Assignee
Kodak Ltd
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 Kodak Ltd filed Critical Kodak Ltd
Publication of GB736922A publication Critical patent/GB736922A/en
Expired 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
    • G03C7/362—Benzoyl-acetanilide couplers

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

4 - (a - 21 - Methoxybenzoyl - a - chloroacetamido) - 311 - (4111 - tert. - amylphenoxy) - benzanilide is prepared by adding sulphuryl chloride with stirring to 4-(21-methoxybenzoylacetamido) - 311 - (4111 - tert. - amylphenoxy)-benzanilide in dry chloroform. 4-(a -21-Methoxybenzoyl - a - chloroacetamido) - 211 : 411 - di-tert. - amylphenoxyacetanilide, a - o - methoxybenzoyl - a - chloro - 4 - [a - (2 : 4 - di - tert.-amylphenoxy) - n - butyramido] - acetanilide, a - chloro - a - (o - methoxybenzoyl) - 4 - [21-(2111 : 4111 - di - tert. - amylphenoxy) - 51-(3111 : 5111 - dicarbomethoxyphenylcarbamyl]-methoxyacetanilide, and a -(o-methoxybenzoyl)-a - chloro - 3 - [a - (21 : 41 - di - tert. - amylphenoxy) - n - butyramido] - acetanilide are similarly prepared. 4 - (21 - Methoxybenzoylacetamido) - 311 - (4111 tert. - amylphenoxy) - benzanilide is prepared by adding m-(p-tert.-amylphenoxy)-benzoyl chloride to a mixture of o-methoxybenzoylacet-4-aminoanilide and sodium acetate-acetic acid solution. 4-(21-Methoxybenzoylacetamido)-211 : 411 - di - tert. - amylphenoxyacetanilide and a - o - methoxybenzoyl - 4 - [a - (2 : 4 - di tert.-amylphenoxy) - n - butyramido) - acetanilide are similarly prepared. o - Methoxybenzoylacet - 4 - aminoanilide is prepared by reducing o-methoxybenzoylacet-4-nitroanilide either with iron powder and acetic acid or with hydrogen over Raney nickel. o - Methoxybenzoylacet - 4 - nitroanilide is prepared by reacting p-nitroaniline with ethyl o-methoxybenzoylacetate in dry xylene containing anhydrous sodium acetate. 4 - (21 - Methoxybenzoylacetamido) - 211 : 411-di - tert. - amylphenoxyacetanilide is alternatively prepared by refluxing together 4-amino - a - (21 : 41 - di - tert. - amylphenoxy)-acetanilide and ethyl o-methoxybenzoylacetate in xylene. a - (o - Methoxybenzoyl) - 4 - [21 - (2111 : 4111-di - tert. - amylphenoxy) - 51 - (3111 : 5111 - dicarbomethoxyphenylcarbamyl) - phenylcarbamyl]-methoxyacetanilide and a -(o-methoxybenzoyl)-3-[a - (21 : 41 - di - tert. - amylphenoxy) - butyramido]-acetanilide are similarly prepared. 4 - Amino - a - (21 : 41 - di - tert. - amylphenoxy-acetanilide is prepared by reacting 2 : 4 - di - tert. - amylphenoxyacetyl chloride with p-phenylenediamine. a - (2 : 4 - Di - tert. - amylphenoxy) - n - butyryl chloride is prepared by refluxing together di-tert.-amylphenol, sodium hydroxide, and a -bromobutyric acid to give a -(2 : 4-di-tert.-amylphenoxy)-n-butyric acid, and refluxing this acid with thionyl chloride. a - (2 : 4 - Di - tert. - amylphenoxy) - 3 - nitrobutyranilide is prepared by reacting a -(2 : 4-di - tert. - amylphenoxy) - butyryl chloride with m-nitroaniline in dioxane containing quinoline. a - (2 : 4 - Di - tert. - amylphenoxy) - 3 - aminobutyranilide is prepared by reducing a -(2 : 4-di - tert. - amylphenoxy) - 3 - nitrobutyranilide in ethanol with hydrogen in presence of Raney nickel. 4 - [21 - (211 : 411 - Di - tert. - amylphenoxy-51 - (3111 : 5111 - di - carbomethoxyphenylcarbamyl) - phenylcarbamyl] - methoxyaniline is prepared by reducing 4-[21-(211 : 411-di-tert.-amyl phenoxy) - 51 - (3111 : 5111 - di - carbomethoxy phenylcarbamyl) - phenylcarbamyl] - methoxynitrobenzene with hydrogen in the presence of Raney nickel, sodium carbonate, and ethanol. 4 - [21 - (211 : 411 - Di - tert. - amylphenoxy) 51 - (3111 : 5111 - di - carbomethoxyphenylcarbamyl) - phenylcarbamyl] - methoxynitrobenzene is prepared by heating together 2-(21 : 41-di-tert. - amylphenoxy) - 5 - (311 : 511 - dicarbomethoxyphenylcarbamyl) - aniline, p - nitrophenoxyacetyl chloride, acetic acid, and anhydrous sodium acetate. 2 - (21 : 41 - Di - tert. - amylphenoxy) - 5-(311 : 511 - dicarbomethoxyphenylcarbamyl) - aniline is prepared by reducing with iron and acetic acid 2-(21 : 41-di-tert.-amylphenoxy)-5-(311 : 511 - dicarbomethoxyphenylcarbamyl) - nitrobenzene, itself prepared by heating together 4 - (21 : 41 - di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride, methyl 5-amino-isophthalate, acetic acid, and anhydrous sodium acetate. 4 - (21 : 41 - Di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride is prepared by refluxing with thionyl chloride 4-(21 : 41-di-tert.-amylphenoxy)-3-nitrobenzoic acid, itself prepared by heating together di-tert.-amylphenol, 4-chloro-3-nitrobenzoic acid, and potassium hydroxide.
GB17750/53A 1952-06-26 1953-06-26 Improvements in photographic colour couplers Expired GB736922A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US295806A US2728658A (en) 1952-06-26 1952-06-26 Benzoyl acetanilide couplers for color photography

Publications (1)

Publication Number Publication Date
GB736922A true GB736922A (en) 1955-09-14

Family

ID=23139302

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17750/53A Expired GB736922A (en) 1952-06-26 1953-06-26 Improvements in photographic colour couplers

Country Status (4)

Country Link
US (1) US2728658A (en)
BE (1) BE521004A (en)
FR (1) FR1098025A (en)
GB (1) GB736922A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB784422A (en) * 1955-01-29 1957-10-09 Ilford Ltd Improvements in or relating to colour photography
BE560907A (en) * 1956-09-18
US3077403A (en) * 1960-05-31 1963-02-12 Gen Aniline & Film Corp Color former containing bis coupling functions
BE607498A (en) * 1960-08-24
CH627562A5 (en) * 1977-04-29 1982-01-15 Ciba Geigy Ag COLOR PHOTOGRAPHIC MATERIAL.
DE19539073A1 (en) * 1995-10-20 1997-04-24 Bayer Ag Process for the preparation of alkylaryl ethers containing carboxyl groups

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2407210A (en) * 1944-04-14 1946-09-03 Eastman Kodak Co Color couplers
FR959910A (en) * 1944-11-02 1950-04-07

Also Published As

Publication number Publication date
BE521004A (en)
US2728658A (en) 1955-12-27
FR1098025A (en) 1955-07-15

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