US2611697A - Light-sensitive photographic element - Google Patents
Light-sensitive photographic element Download PDFInfo
- Publication number
- US2611697A US2611697A US741684A US74168447A US2611697A US 2611697 A US2611697 A US 2611697A US 741684 A US741684 A US 741684A US 74168447 A US74168447 A US 74168447A US 2611697 A US2611697 A US 2611697A
- Authority
- US
- United States
- Prior art keywords
- light
- acid
- layers
- sensitive
- photographic element
- 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
- -1 SILVER HALIDE Chemical class 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- SWHSXWLSBBYLGM-UHFFFAOYSA-N 2-[(2-carboxyphenoxy)methoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCOC1=CC=CC=C1C(O)=O SWHSXWLSBBYLGM-UHFFFAOYSA-N 0.000 claims description 3
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- CCJWAFRVAHAVKQ-UHFFFAOYSA-N 2-(dibromoamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N(Br)Br CCJWAFRVAHAVKQ-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- FZRCKLPSHGTOAU-UHFFFAOYSA-N 6-amino-1,4-dimethylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound CC1=CC(N)C(C)(C=O)C=C1 FZRCKLPSHGTOAU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002966 varnish Substances 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
Definitions
- Anti-halation layers have to meet the following requirements: their absorptive power should be adapted to the optical sensitivity of the silver halide emulsions; they should lose color quickly,
- the layers should also withstand mechanical influences which remove the dyestufi itself or which could damage the thin layer.
- a further object of our present invention is to provide a photographic light-sensitive single or multi-layer silver halide material containing at least one of the said colored photographic layers.
- our invention consists in the prodnot and the method of producing same, as hereinafter are more particularly described in the methine dyestuffs of the type that is obtainable as, for, instance," by condensationof substituted or unsubstituted aliphatic, aromatic or heterocyclic' aldehydes with suitablesubstituted anilcines' oramines, preferably in equimolar' quanti
- the color intensity of the dyestuffs is considerably increased.
- para-anisidin para-amidodiphenylam-ine, ortho-anisidin, para-toluylediamine, l m. dibromoanthranilic acid, aminophenyltliiocarbamide.
- Suitable aldehydes are, ea g.,. para-dimethyl- Example 1 1 mol anthranilic acid and 1 mol para-dimethylaminobenzaldehyde are heated in a diluted alcoholic solution. A colored combination separates immediately and is crystallised from alcohol (iJOOBK 3 .ErampZe 2 1 mol anisic aldehyde is condensed as in Example 1 with 1 mol amidodiphenylamine to an azomethine dyestufi of the following probable structure This azomethlne dye base is condensed in equimolar proportions with salicyclic acid in alcohol.
- Example 3 COOH All of the above dyestuffs are suitable for all photographic purposes where a layer discolorable in a weak alkaline medium is required, as e. g. for filter layers, anti-halation layers, back layers, and also for direct addition to the silver halide emulsion.
- Photographic material containing at least one light-sensitive silver'halide emulsion layer and a colored non-sensitive layer including the reaction product of a basic azomethine dyestuif, obtained by condensing in equimolar proportions an aldehyde selected from the group consisting of p-dimethylaminobenzaldehyde and p-dimethylaminocinnamic aldehyde, and anthranilic acid, with methylene disalicylic acid, said reaction product; corresponding to the following formula:
- A represents the atoms necessary to complete with H benzoic acid
- B represents the atoms necessary to complete with OHC- an aldehyde selected from said group of aldehydes
- R represents the atoms necessary to complete with H methylene disalicylic acid, the radical of the latter acid being linked to the N-atom so that 4 the salt-formingOI-I remains intact
- n represents a positive integer of from 1 to 2.
- Photographic material containing at least one light-sensitive silver halide emulsion layer and a colored non-sensitive layer including the dyestuff of the formula:
- Photographic material containing at least one' light-sensitive silver halide emulsion layer and a colored non-sensitive layer including the dyestuff of the formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Color Printing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE622731X | 1942-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2611697A true US2611697A (en) | 1952-09-23 |
Family
ID=6577754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US741684A Expired - Lifetime US2611697A (en) | 1942-04-22 | 1947-04-15 | Light-sensitive photographic element |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2611697A (en, 2012) |
| BE (1) | BE450286A (en, 2012) |
| FR (1) | FR894181A (en, 2012) |
| GB (1) | GB622731A (en, 2012) |
| NL (1) | NL60349C (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727821A (en) * | 1954-05-26 | 1955-12-20 | Gen Aniline & Film Corp | Photographic filter layers irreversibly dischargeable by the use of photographic bleaching agents |
| US3457301A (en) * | 1965-04-29 | 1969-07-22 | Ugine Kuhlmann | Disazomethine pigments |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2696438A (en) * | 1950-04-11 | 1954-12-07 | Gaspar | Light screening photographic layer |
| US2677612A (en) * | 1950-04-11 | 1954-05-04 | Gaspar | Photographic light-sensitive element |
| US2695233A (en) * | 1950-12-09 | 1954-11-23 | Gen Aniline & Film Corp | Irreversibly dischargeable photographic filter layers and method of processing film containing the same |
| BE525719A (en, 2012) * | 1953-01-14 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1879537A (en) * | 1929-10-31 | 1932-09-27 | Agfa Ansco Corp | Anti-halation layers for photographic material |
| GB539070A (en) * | 1940-02-21 | 1941-08-27 | Eastman Kodak Co | Improvements relating to the use of substituted aromatic amines in photography |
| US2276158A (en) * | 1940-01-22 | 1942-03-10 | Universal Oil Prod Co | Suppression of metal catalysis |
| US2282890A (en) * | 1939-03-28 | 1942-05-12 | Gen Aniline & Film Corp | Antihalo coating for photographic material |
| US2336215A (en) * | 1941-03-15 | 1943-12-07 | Eastman Kodak Co | Isoalkylidene aminophenol |
| US2388903A (en) * | 1943-04-29 | 1945-11-13 | Gulf Oil Corp | Manufacture of azo-methine compounds |
| US2396580A (en) * | 1940-06-25 | 1946-03-12 | Kulz Fritz | Method for preparation of oxyphenyl-amino-propane and its derivatives |
-
0
- BE BE450286D patent/BE450286A/xx unknown
- NL NL60349D patent/NL60349C/xx active
-
1943
- 1943-04-22 FR FR894181D patent/FR894181A/fr not_active Expired
-
1945
- 1945-09-24 GB GB24732/45A patent/GB622731A/en not_active Expired
-
1947
- 1947-04-15 US US741684A patent/US2611697A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1879537A (en) * | 1929-10-31 | 1932-09-27 | Agfa Ansco Corp | Anti-halation layers for photographic material |
| US2282890A (en) * | 1939-03-28 | 1942-05-12 | Gen Aniline & Film Corp | Antihalo coating for photographic material |
| US2276158A (en) * | 1940-01-22 | 1942-03-10 | Universal Oil Prod Co | Suppression of metal catalysis |
| GB539070A (en) * | 1940-02-21 | 1941-08-27 | Eastman Kodak Co | Improvements relating to the use of substituted aromatic amines in photography |
| US2396580A (en) * | 1940-06-25 | 1946-03-12 | Kulz Fritz | Method for preparation of oxyphenyl-amino-propane and its derivatives |
| US2336215A (en) * | 1941-03-15 | 1943-12-07 | Eastman Kodak Co | Isoalkylidene aminophenol |
| US2388903A (en) * | 1943-04-29 | 1945-11-13 | Gulf Oil Corp | Manufacture of azo-methine compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727821A (en) * | 1954-05-26 | 1955-12-20 | Gen Aniline & Film Corp | Photographic filter layers irreversibly dischargeable by the use of photographic bleaching agents |
| US3457301A (en) * | 1965-04-29 | 1969-07-22 | Ugine Kuhlmann | Disazomethine pigments |
Also Published As
| Publication number | Publication date |
|---|---|
| FR894181A (fr) | 1944-12-15 |
| BE450286A (en, 2012) | |
| GB622731A (en) | 1949-05-06 |
| NL60349C (en, 2012) |
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