GB975932A - Improvements in or relating to the production of colour photographic images - Google Patents

Improvements in or relating to the production of colour photographic images

Info

Publication number
GB975932A
GB975932A GB3855159A GB3855159A GB975932A GB 975932 A GB975932 A GB 975932A GB 3855159 A GB3855159 A GB 3855159A GB 3855159 A GB3855159 A GB 3855159A GB 975932 A GB975932 A GB 975932A
Authority
GB
United Kingdom
Prior art keywords
prepared
methyl
iodide
phenyl
refluxing
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
GB3855159A
Inventor
Jozef Frans Willems
Jan Jaeken
Robert Leopold Jansseune
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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
Priority to NL295656D priority Critical patent/NL295656A/xx
Priority to FR79706D priority patent/FR79706E/fr
Priority to NL263254D priority patent/NL263254A/xx
Priority to BE602250D priority patent/BE602250A/xx
Priority to BE634930D priority patent/BE634930A/xx
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Priority to GB3855159A priority patent/GB975932A/en
Priority to US71117A priority patent/US3245787A/en
Priority to DEG30927A priority patent/DE1300019B/en
Priority to FR843846A priority patent/FR1287364A/en
Priority to US100010A priority patent/US3245788A/en
Priority to DEG31993A priority patent/DE1297470B/en
Priority to GB29127/62A priority patent/GB993749A/en
Priority to CH778163A priority patent/CH428435A/en
Priority to FR941295A priority patent/FR84327E/en
Priority to DE1447678A priority patent/DE1447678C3/en
Publication of GB975932A publication Critical patent/GB975932A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/18—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • G03C7/18—Processes for the correction of the colour image in subtractive colour photography

Landscapes

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

Abstract

Sulphonyl hydrazones of one of the following formulae <FORM:0975932/C1/1> , <FORM:0975932/C1/2> , <FORM:0975932/C1/3> wherein Y and Z are the non-metallic atoms required to complete a heterocyclic ring, X1 is alkyl or substituted phenyl, R2 is alkyl sulphonyl, R3 and R4 are alkyl, allyl, or phenyl and R5 is phenyl, substituted phenyl, benzyl or a heterocyclic radical are prepared by heating a sulphonyl hydrazide with a methyl mercapto cycloammonium salt or by refluxing a sulphonyl chloride with an unsubstituted hydrazone. Sulphonyl hydrazones prepared include those wherein X1 is cetyl, or 4-carboxyphenyl-4-methylphenyl or 3-decanoyl-amino-phenyl, R3 and R4 are methyl or ethyl, R5 is phenyl, thienyl or alkoxy- or chloro-phenyl, Z completes a thiazoline, benzothiazoline, benzoxazoline, quinoline or benzimidazoline ring and Y completes a piperazine or morpholine ring. N;N1 - dimethyl - N;N1-diphenyl-N1 -aminoguanidine is prepared by heating N,N1-dimethyl-N,N1-diphenyl-S-methyl-isothiouranium iodide with hydrazine hydrate. N11, N11, N111, N111-diethylene - di (N-n-hexadecylsulphonylbenzamidrazone) is prepared by refluxing N:N-dibenzoyl piperazine with phosphorus pentasulphide to give N:N-dibenzothiopiperazide which is reacted with methyl iodide to give the salt. The salt is reacted with n-hexadecylsulphonylhydroxide to produce the desired compound. 3-methyl-2-benzothiazolone semicarbazone is prepared by refluxing semicarbazide hydrochloride with 2-methyl-thio-3-methylbenzothiazolium methylsulphate under alkaline conditions. 1-phenyl-3-N-carbethoxythioureido-5-pyrazolone is prepared by refluxing 1-phenyl-3-amino-5-pyrazolone with carbethoxyisothiocyanate. p-Hexadecyloxyacetophenone is prepared by refluxing p-hydroxy acetophenone with hexadecylbromide in caustic potash. p-Hexadecylphenacylbromide is prepared by heating the acetophenone with bromine. 1-Phenyl-3-\sT 31-carbethoxy-41-(411-hexadecyloxyphenyl) -thiazolylidene-21\sV-amino-5-pyrazolone is prepared by refluxing p-hexadecylphenacylbromide with 1-phenyl-3-N-carbethoxythioureido -5-pyrazolone. N - ethyl - benzothiazolone - (m - nitrophenyl)-sulphonyl hydrazone is produced by refluxing N-ethyl-benzothiazolone with m-nitrobenzene sulphochloride. The amino compound is prepared by reduction with iron filings. Cetyl sulphonyl hydrazide is prepared by adding hydrazine hydrate to cetyl sulphonyl chloride. 4 - (alpha - methylthiothienylidene) - morpholinium iodide is prepared by heating sulphur, 2-thiophene-2-aldehyde and morpholine to produce 4-(thiothienoyl)-morpholine which on refluxing with methyl iodide gives the desired product. 1-a -methylthio-3-methoxy -4- n - hexadecyloxybenzylidene-piperidinium iodide is prepared by refluxing sodium, 3-methoxy-4-hydroxybenzaldehyde and n-hexadecylbromide to give 3-methoxy-4-n-hexadecyloxybenzaldehyde. This aldehyde is heated with sulphur and piperidine to give 3-methoxy-4-n-hexadecyloxy-benzothiopiperide which is reacted with methyl iodide to give the piperidinium iodide. 3-methoxy-4-hydroxy-benzothiopiperidide is produced by heating sulphur, piperidine and 3-methoxy-4-hydroxy benzaldehyde. The iodide is prepared as above. 4-methoxybenzothiomorpholide is prepared by heating sulphur, morpholine and p-methoxybenzaldehyde. 2, 4-dichlorobenzothiomorpholide is prepared by adding 2, 4-dichlorobenzoylchloride to morpholine in alkaline solution to obtain 2, 4-dichlorobenzomorpholide which is refluxed with phosphorus pentasulphide to give the thiomorpholide. 2-chlorobenzothiomorpholide is prepared as above using o-chloro-benzoyl chloride. a -methylthio -3, 4-dimethoxybenzylidene - N - methyl-N-n-hexadecyl-ammonium iodide is prepared by adding 3, 4-dimethoxybenzoylchloride to N-methyl-N-n-hexadecylamine in alkali to give 3, 4-dimethoxy-benzoic acid-N-methyl-N-n-hexadecylamide. This is reacted with phosphorus pentasulphide to give 3, 4-dimethoxy-benzothio-N-methyl-N-n-hexadecylamide which is quaternized with methyl iodide. a -methylthio -4- methoxybenzylidene-N-methyl-N-n-hexadecyl ammonium iodide is prepared as above using p-methoxybenzoylchloride instead of 3, 4-dimethoxybenzoyl chloride. a -methylthiobenzylidene-N-allylanilinium iodide is prepared by refluxing N-allylaniline with benzoylchloride to give N-aleylbenzanilide. This anilide is reacted with phosphorus pentasulphide to give N-allyl-benzothioanilide which is quaternized with methyliodide. 4-Carboxybenzene sulphonylhydrazide is prepared from hydrazine and 4-carboxybenzene sulphonyl chloride. Specifications 502,665, 880,862, 975,930, 975,939 and 975,940 are referred to.
GB3855159A 1959-11-13 1959-11-13 Improvements in or relating to the production of colour photographic images Expired GB975932A (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
NL295656D NL295656A (en) 1959-11-13
FR79706D FR79706E (en) 1959-11-13
NL263254D NL263254A (en) 1959-11-13
BE602250D BE602250A (en) 1959-11-13
BE634930D BE634930A (en) 1959-11-13
GB3855159A GB975932A (en) 1959-11-13 1959-11-13 Improvements in or relating to the production of colour photographic images
DEG30927A DE1300019B (en) 1959-11-13 1960-11-14 Process for the production of a multicolor image comprising integral colored mask images
US71117A US3245787A (en) 1959-11-13 1960-11-14 Production of color photographic images
FR843846A FR1287364A (en) 1959-11-13 1960-11-14 Process for the production of color photographic images
US100010A US3245788A (en) 1959-11-13 1961-04-03 Production of color photographic images
DEG31993A DE1297470B (en) 1959-11-13 1961-04-06 Process for the production of a multicolor image comprising integral colored mask images
GB29127/62A GB993749A (en) 1959-11-13 1962-07-30 Production of colour photographic images
CH778163A CH428435A (en) 1959-11-13 1963-06-24 Method for obtaining a color corrected photographic image
FR941295A FR84327E (en) 1959-11-13 1963-07-12 Process for the production of color photographic images
DE1447678A DE1447678C3 (en) 1959-11-13 1963-07-30 Color photographic recording material and process for the production of color masked single or multicolor photographic images

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3855159A GB975932A (en) 1959-11-13 1959-11-13 Improvements in or relating to the production of colour photographic images

Publications (1)

Publication Number Publication Date
GB975932A true GB975932A (en) 1964-11-25

Family

ID=10404207

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3855159A Expired GB975932A (en) 1959-11-13 1959-11-13 Improvements in or relating to the production of colour photographic images

Country Status (1)

Country Link
GB (1) GB975932A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6124242A (en) * 1998-06-26 2000-09-26 Basf Aktiengesellschaft Herbicidal compositions and processes based on ferrodoxin:NADP reductase inhibitors

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6124242A (en) * 1998-06-26 2000-09-26 Basf Aktiengesellschaft Herbicidal compositions and processes based on ferrodoxin:NADP reductase inhibitors

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