GB1379813A - Benzoylacetanilide yellow forming colour couplers for phtographic silver halide material - Google Patents

Benzoylacetanilide yellow forming colour couplers for phtographic silver halide material

Info

Publication number
GB1379813A
GB1379813A GB1134072A GB1134072A GB1379813A GB 1379813 A GB1379813 A GB 1379813A GB 1134072 A GB1134072 A GB 1134072A GB 1134072 A GB1134072 A GB 1134072A GB 1379813 A GB1379813 A GB 1379813A
Authority
GB
United Kingdom
Prior art keywords
methoxy
ester
methyl ester
itself
compound
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
GB1134072A
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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 Gevaert AG filed Critical Agfa Gevaert AG
Publication of GB1379813A publication Critical patent/GB1379813A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • 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

  • 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)

Abstract

1379813 Benzoylacetanilides; intermediates therefor AGFA-GEVAERT 10 March 1972 [25 March 1971] 11340/72 Heading C2C [Also in Division G2] The invention comprises compounds of the formula wherein X represents H or a group that exhibits two-equivalent character, R 1 and R 2 represent straight or branched-chain (C 1 to C 20 )alkyl groups, Y represents COOR 3 , where R 3 and R 6 represent straight or branchedchain alkyl groups of which the carbon chain may be interrupted by -O-, and R 4 , R 5 , R, and R 8 represent H or are the same as R 3 and R 6 ; the molecule comprising at least one (C 5 to C 20 ) alkyl group. In examples specified compounds are obtained by reacting an appropriate benzoyl acetic acid ester with an appropriate aniline derivative. They are useful as colour couplers. 3 - n - Hexadecyloxy - 4 - amino - benzoic acid methyl ester is obtained by hydrogenating the corresponding nitro compound which is itself obtained by etherifying the potassium salt of 3-hydroxy-4-nitrobenzoic acid methyl ester with hexadecyl bromide in DMF. 3 - n - Hexadecyloxy - 4 - aminobenzoic acid 2-methoxy-ethyl ester is obtained by hydrogenating the corresponding nitro compound which is itself obtained by transesterifying 3-n-hexadecyloxy-4-nitrobenzoic acid methyl ester with ethylene glycol monomethyl ether in the presence of Na. 3-Methoxy-4-aminobenzoic acid methyl ester is obtained by hydrogenating the corresponding nitro compound which is itself obtained by etherifying the potassium salt of 3-hydroxy-4- nitrobenzoic acid methyl ester with (CH 3 ) 2 SO 4 in DMF. 3-Methoxy-4-aminobenzoic acid n-hexadecyl ester is obtained by transesterifying the corresponding methyl ester with hexadecyl alcohol in the presence of titanium tetrabutoxide as catalyst. 3-Methoxy-4-aminobenzoic acid isooctadecyl ester and 3-methoxy-4-aminobenzoic acid #-methoxyethyl ester are obtained in a similar manner. 2 - Dodecyloxy - 4 - methylsulphonyl - aniline is obtained by oxidizing with urea peroxide 2 - dodecyloxy - 4 - methylthioacetanilide and hydrolysing the resulting acetanilide. 2- Dodecyloxy-4-methylthioacetanilide is obtained by treating the corresponding 4-thiocyanato compound in methanolic CH 3 I with Na in methanol. The 4-thiocyanato compound is itself obtained by acetylating 2 - dodecyloxy - 4 - thiocyanatoaniline which is itself obtained by treating a mixture of 2-dodecyloxyaniline and ammonium thiocyanate in CH 3 CN with Br 2 . 2-Methoxy-4-methylsulphonyl-aniline is obtained in a similar manner via 2 - methoxy - 4 - methylsulphonylacetanilide, 2 - methoxy - 4 - methylthioacetanilide and 2 - methoxy - 4 - thiocyanatoacetanilide from 2-methoxy-4-thiocyanatoaniline. 2 - Amino - 5 - N,N - dimethylaminosulphonylanisole is obtained by etherifying with CH 3 I in methanolic KOH the corresponding 2-acetylamino-phenol compound and deacetylating the product with hydrochloric acid. 2-Acetylamino- 5-N,N-dimethylaminosulphonyl phenol is itself obtained by acetylating the corresponding amine which is itself obtained by treating 6 - N,N - dimethylaminosulphonyl - benzoxazolone-2 with NaOH and neutralizing the product with hydrochloric acid. The latter compound is obtained by treating 6-chlorosulphonyl-benzoxazolone-2 with dimethylamine in dioxan. 2 - n - Hexadecyloxy - 4 - N,N - dimethylaminosulphonyl-aniline is obtained by hydrolysing the corresponding acetanilide which is itself obtained by etherifying 2-acetylamino-5-N,N-dimethylaminosulphonylphenyl with hexadecyl bromide in the presence of ethylene glycol monomethyl ether and sodium.
GB1134072A 1971-03-25 1972-03-10 Benzoylacetanilide yellow forming colour couplers for phtographic silver halide material Expired GB1379813A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712114578 DE2114578A1 (en) 1971-03-25 1971-03-25 Photographic yellow coupler

Publications (1)

Publication Number Publication Date
GB1379813A true GB1379813A (en) 1975-01-08

Family

ID=5802773

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1134072A Expired GB1379813A (en) 1971-03-25 1972-03-10 Benzoylacetanilide yellow forming colour couplers for phtographic silver halide material

Country Status (6)

Country Link
US (1) US3843366A (en)
BE (1) BE780164A (en)
DE (1) DE2114578A1 (en)
FR (1) FR2130156B1 (en)
GB (1) GB1379813A (en)
IT (1) IT960497B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1460585A (en) * 1973-04-06 1977-01-06 Agfa Gevaert Acylacetanilide derivatives as colour couplers for yellow
DE2361471A1 (en) * 1973-12-10 1975-06-12 Agfa Gevaert Ag YELLOW COUPLER CONTAINING PHOTOGRAPHIC MATERIAL
US4193559A (en) * 1978-04-07 1980-03-18 E. I. Du Pont De Nemours And Company Film web winding assembly
DE3441525A1 (en) * 1984-11-14 1986-05-15 Agfa-Gevaert Ag, 5090 Leverkusen COLOR PHOTOGRAPHIC COLOR COUPLING RECORD MATERIAL

Also Published As

Publication number Publication date
FR2130156B1 (en) 1976-10-29
FR2130156A1 (en) 1972-11-03
BE780164A (en) 1972-09-04
IT960497B (en) 1973-11-20
DE2114578A1 (en) 1972-10-05
US3843366A (en) 1974-10-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
435 Patent endorsed 'licences of right' on the date specified (sect. 35/1949)
PCNP Patent ceased through non-payment of renewal fee