US2436007A - Dye intermediates for colour photography - Google Patents
Dye intermediates for colour photography Download PDFInfo
- Publication number
- US2436007A US2436007A US591831A US59183145A US2436007A US 2436007 A US2436007 A US 2436007A US 591831 A US591831 A US 591831A US 59183145 A US59183145 A US 59183145A US 2436007 A US2436007 A US 2436007A
- Authority
- US
- United States
- Prior art keywords
- colour photography
- dye intermediates
- colour
- image
- acylanilido
- 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
Links
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- -1 acylanilido Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- CIXAYNMKFFQEFU-UHFFFAOYSA-N (4-Methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 description 1
- 241001093575 Alma Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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
Definitions
- ⁇ and particularly ⁇ tofzdyestuil ,intermediatesjgr nitro group, and R5 is either' agroupf'of the same -use in colour ,photographic@processes class-as' Re or is a hydrogen atoin'"o a hydrocar- Processes of colour; photographyf-a1e Welle-lil ibonfgrouxhw; .51,1 .V
- a process of colour photography which comprises forming a reducible silver salt image in an emulsion layer of a photographic element vhich contains a compound of the general forula:
- Ra RI-CHT-CH C/ Rl
- R1 is an aryl group
- R2 is a group selected from the class consisting of -CN radicals.
- R3 is a group selected from the class consisting of the hydrogen atom -CN radicals, acyl, acylanilido, carboxy, alkoxy, carbethoxy, nitro and hydrocarbon groups, and developing said image with an N,Ndialky1pphenylene diamine.
- a process of colour photography which comprises forming a reducible silver salt image in an emulsion layer of a photographic element which includes, adjacent thereto, a layer containing a compound of the general formula:
- a process of colour photography which comprises forrning a reducible silver salt image in an emulsion layer of a photographic element which includes ⁇ adjacent thereto. a layer containing a compound of the general formula:
- R1 is an aryl group
- Rz is a group selected from the class consisting of -CN radicals. acyl, acylanilido, carboxy, alkoXy, carbethoxy. and nitro groups
- R3 is a group selected from the class consisting of the hydrogen atom -CN radicals, acyl, acylanilido, carboxy, alkoxy. carbethoXy, nitro and hydrocarbon groups, and developing said image with an N,Ndia1kylpphenylene diamine.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
infested Peb. 17, i948 I r 2,436,007
PATan/r ori-'Ica Drmufrnannm'ms Fon cocoon John Davidm Kendall and Douglas James' Fry,
Ilford, England, asslgnors to llfrd"Lmited, y Vlllford, England, a British company y L No llrawing. Application May 3, 1945, Serial No. 591,831. In Great Britain May 412,A 1944 y ss-s) 1 s .This invention re1ates,;to` colour photography carboxy, alkoxy,"carbethoxy acyl,"acylanilido, or
`and: particularly` tofzdyestuil ,intermediatesjgr nitro group, and R5 is either' agroupf'of the same -use in colour ,photographic@processes class-as' Re or is a hydrogen atoin'"o a hydrocar- Processes of colour; photographyf-a1e Welle-lil ibonfgrouxhw; .51,1 .V
known in` which zcoloured; images are-produced 5 .l :Thesescompounds'maybe prpled bryan dibn,"
'bythe developmentlof redueble silver salt images :.veni'ent, methodu suitable `method is by "e l bysmeans of aromatic primary-amino developing .condensation of 'an Varyl acetalgehyde with conru l f Y Aabove.there may .belemployedforexampla'fw I `1min-1tA isls'uitable for the particular colour .proc- .naphthyraeeraldehyee ,s-aphthylf aeetamehyoe..
" .esswithWhichvltiscintenddto be'usedi :i203 vlinethoxyphenyl 'u "fac'etaldehyde, p-chlorphe'nyl f According-to='the`pesentinventionlsaprocess 40.. cetaldehydg p-tolyl acetaldehyde, 1 ,fp-nitro offcol'olur photographylcomprisesrrdevelopinga lienylfacetaldehyde or pfethXl/Dhenyl acetabreducible silver-'salt image by means of an aroehydenfOther. compounds' for re'action there matic primary anrw.4 developing agent in the Vwith lnenrale.oyen?,mammeT and )aceto acetic;
presence of a eompoundof the general formula `fesgigsl and` alvnilid'es@` malodinitrile, Lcyaae'etpl-pigs;linoylacet estrsand'anilides', phenyl acetonitrile, diaroyll methanes, ,and quaternai'ygisalta f Y Y 'f y Y alma:@Ethyl-@cunningaorlrposltbfrdlh where R1 is an aryl group, Rz is a -CN radical. 50 Quaternary nitrgen 810m.
class consisting of the hydrogen atom -CN radicals, acyl,`acylanilido. carboxy. alkoxy, carbethoxy, nitro and hydrocarbon groups, and developing said image with an aromatic primary amino developing agent.
6. A process of colour photography which comprises forming a reducible silver salt image in an emulsion layer of a photographic element vhich contains a compound of the general forula:
Ra RI-CHT-CH=C/ Rl Where R1 is an aryl group, R2 is a group selected from the class consisting of -CN radicals. acyl, acylanilido, carboxy, alkoxy, carbethoxy, and ni` tro groups and R3 is a group selected from the class consisting of the hydrogen atom -CN radicals, acyl, acylanilido, carboxy, alkoxy, carbethoxy, nitro and hydrocarbon groups, and developing said image with an N,Ndialky1pphenylene diamine.
7. A process of colour photography which comprises forming a reducible silver salt image in an emulsion layer of a photographic element which includes, adjacent thereto, a layer containing a compound of the general formula:
6 ing said image with an aromatic primary amino developing agent.
8. A process of colour photography which comprises forrning a reducible silver salt image in an emulsion layer of a photographic element which includes` adjacent thereto. a layer containing a compound of the general formula:
where R1 is an aryl group, Rz is a group selected from the class consisting of -CN radicals. acyl, acylanilido, carboxy, alkoXy, carbethoxy. and nitro groups and R3 is a group selected from the class consisting of the hydrogen atom -CN radicals, acyl, acylanilido, carboxy, alkoxy. carbethoXy, nitro and hydrocarbon groups, and developing said image with an N,Ndia1kylpphenylene diamine.
JOHN DAVTD KENDALL.
DOUGLAS JAMES FRY.
REFERENCES CITED The following references are of record in the le of this patent:
UNITED STATES PATENTS Number Name Date 2,126,337 Mannes et al. Aug. 9. 1938 2,186,736 Schneider et al. Jan. 9. 1940 2,295,009 Porter et al. Sept. 8. 1942 2,328,652 Kirby et al Sept. 7, 1943 2,338,676 Vittum et al. Jan. 4, 1944 FOREIGN PATENTS Number Country Date 478,991 Great Britain Jan. 24, 1938
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2436007X | 1944-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2436007A true US2436007A (en) | 1948-02-17 |
Family
ID=10906875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US591831A Expired - Lifetime US2436007A (en) | 1944-05-12 | 1945-05-03 | Dye intermediates for colour photography |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2436007A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2494054A (en) * | 1948-04-06 | 1950-01-10 | Eastman Kodak Co | Antistatic photographic film |
| US2537001A (en) * | 1947-08-06 | 1951-01-02 | Gen Aniline & Film Corp | Diazotype layers having cyan acetyl amides as azo components |
| US2552355A (en) * | 1947-08-06 | 1951-05-08 | Gen Aniline & Film Corp | Diazotype layers having organic esters and nitriles containing an active methylene group as azo components |
| US3052636A (en) * | 1959-05-26 | 1962-09-04 | Gen Aniline & Film Corp | Ultra-violet light stabilized organic compositions |
| US3074971A (en) * | 1959-01-23 | 1963-01-22 | Gen Aniline & Film Corp | alpha-cyanocinnamic acid esters |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB478991A (en) * | 1936-04-23 | 1938-01-24 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| US2126337A (en) * | 1935-03-21 | 1938-08-09 | Eastman Kodak Co | Photographic color-forming compounds |
| US2186736A (en) * | 1937-07-03 | 1940-01-09 | Agfa Ansco Corp | Coupling compounds for color forming development |
| US2295009A (en) * | 1940-03-12 | 1942-09-08 | Eastman Kodak Co | Photographic color forming compound |
| US2328652A (en) * | 1941-04-18 | 1943-09-07 | Du Pont | Process of color photography and composition thereof |
| US2338676A (en) * | 1941-12-12 | 1944-01-04 | Eastman Kodak Co | Phenolic coupler compound |
-
1945
- 1945-05-03 US US591831A patent/US2436007A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126337A (en) * | 1935-03-21 | 1938-08-09 | Eastman Kodak Co | Photographic color-forming compounds |
| GB478991A (en) * | 1936-04-23 | 1938-01-24 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| US2186736A (en) * | 1937-07-03 | 1940-01-09 | Agfa Ansco Corp | Coupling compounds for color forming development |
| US2295009A (en) * | 1940-03-12 | 1942-09-08 | Eastman Kodak Co | Photographic color forming compound |
| US2328652A (en) * | 1941-04-18 | 1943-09-07 | Du Pont | Process of color photography and composition thereof |
| US2338676A (en) * | 1941-12-12 | 1944-01-04 | Eastman Kodak Co | Phenolic coupler compound |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537001A (en) * | 1947-08-06 | 1951-01-02 | Gen Aniline & Film Corp | Diazotype layers having cyan acetyl amides as azo components |
| US2552355A (en) * | 1947-08-06 | 1951-05-08 | Gen Aniline & Film Corp | Diazotype layers having organic esters and nitriles containing an active methylene group as azo components |
| US2494054A (en) * | 1948-04-06 | 1950-01-10 | Eastman Kodak Co | Antistatic photographic film |
| US3074971A (en) * | 1959-01-23 | 1963-01-22 | Gen Aniline & Film Corp | alpha-cyanocinnamic acid esters |
| US3052636A (en) * | 1959-05-26 | 1962-09-04 | Gen Aniline & Film Corp | Ultra-violet light stabilized organic compositions |
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