US2930693A - Photographic materials containing n-substituted phthalimide compounds - Google Patents
Photographic materials containing n-substituted phthalimide compounds Download PDFInfo
- Publication number
- US2930693A US2930693A US619137A US61913756A US2930693A US 2930693 A US2930693 A US 2930693A US 619137 A US619137 A US 619137A US 61913756 A US61913756 A US 61913756A US 2930693 A US2930693 A US 2930693A
- Authority
- US
- United States
- Prior art keywords
- photographic materials
- substituted
- materials containing
- substituted phthalimide
- layers
- 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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000463 material Substances 0.000 title description 12
- 239000000839 emulsion Substances 0.000 claims description 17
- 229910052709 silver Inorganic materials 0.000 claims description 12
- 239000004332 silver Substances 0.000 claims description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000005543 phthalimide group Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- AEADBBUECVLTRS-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC(CC)=NC2=CC=1C1=CC=CC=C1 AEADBBUECVLTRS-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- -1 silver halide Chemical class 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/42—Developers or their precursors
-
- 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
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Definitions
- This invention relates to photographic materials and more particularly to light-sensitive photographic materials containing developers.
- the photographic materials are passed through a tank containing the developer insolution.
- the concentration of the developer falls so that the processing conditions vary and it is eventually necessary to add new developer to the tank.
- the developer solution has to ditluse through the upper layers of the photographic materials before it can reach the lower layers so that an' even development of the various layers cannot'be achieved.
- correct development of the bottom layer can only be obtained by having a high concentration of developer in the developer solution, but under these conditions there is a tendency forthe top layer to be over-developed.
- a light sensitive gelatino-silver halide emulsion layer which contains a substituted phthalimide of the formula R1 C i 1 RI ⁇ C O J wherein R and R are substituted or unsubstituted alkyl radicals or R and R may be joined together or each or both joined to the benzene ring to form with the nitrogen atom a heterocyclic ring, X is hydrogen, an alkyl, substituted alkyl, alkyloxy, substituted alkyloxy, amino or substituted amino radical, and Y is a solubilising group, and wherein the benzene nuclei may carry substituents.
- the solubilising group may be for example a carboxylic or sulphonic acid group or a salt of one of these, for example an alkali metal or ammonium salt.
- the substitutedphthalimidea may- :be made-iby.1-.-heating.-.
- R R and X have the meaning given above and thephenyl nucleus may carry further.substituents,,with1: phthalic anhydride or a substituted phthalic anhydrideg.. and, where both the amine and; phthalicranhydride-are groups, further treatingthe free from water solubilising product to introduce a water solubilisinggroupr
- the gelatinosilver halideiemulsion nlayer also contains a ,colour coupler.
- the emulsions vused .for forming -the-layers ofounirb; vention may be made by simply.,mixing;an- .aqueousisolu tion or dispersion of the substituted phthalim de with a normal gelatino-silver halide emulsiqn prepared in thre known manner and if desiredadding one. onmore sen-1:
- halide emulsion layer containing a substituted phthalimide as hereinbefore-- defined forms a further feature of our invention.
- Photographic materials containing the light-sensitive emulsion layers of our invention may be exposed to light in the normal way and then developed with an alkaline solution containing hydroxylamine or hydrazine and this process of development forms a further feature of our invention. If desired other adjuvants for example sodium sulphite and potassium bromide may be added to the developer solution. The material may then be fixed and, when the emulsion layer contains a colour coupler, the developed silver may be bleached.
- Example parts of a gelatin-silver iodo-bromide emulsion containing 7.25% of gelatine, 3.35% of silver bromide and 0.05 of silver iodide are stirred and there are added 3 parts of a 0.05% solution in methanol of bis (3 ethyl 5 phenyl benzoxazole 2-) 9-ethy1trimethineyanine iodide (the iodide of the green sensitising dyestuit Rl340 described in B.I.O.S. Final Report No. 1355, page 86).
- the mixture is stirred at 40 C.
- the paper is washed and then transferred to a stop bath of the following composition:
- the paper is washed and the developed silver is bleached and fixed in a solution of the following composition:
- the paper is finally washed and dried.
- a light sensitive gelatino-silver halide emulsion which contains a substituted phthalimide of the formula:
- R and R are alkyl radicals
- X is selected from the group consisting of alkyl, alkoxy and amino
- Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups.
- a light sensitive gelatino-silver halide emulsion ac cording to claim 1 which contains, in addition to the substituted phthalimide as defined in claim 1, a colour coupler capable of coupling with the oxidation product of a primary aromatic amino developer to form a dye.
- a photographic material comprising a plurality of layers coated on a support, at least one of said layers being a light sensitive gelatino-silver halide emulsion layer which contains a substituted phthalimide of the formula:
- R and R are alkyl radicals
- X is selected from the group consisting of alkyl, alkoxy and amino
- Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups, and which further contains a colour coupler capable of coupling with the oxidation product of a primary aromatic amino developer to form a dye.
- a 'colour photographic process which comprises imagewise exposing to light a light sensitive gelatino-silver halide emulsion which contains a substituted phthalimide of the formula:
- R and R are allcyl radicals
- X is selected from the group consisting of alltyl, alkoxy and amino
- Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups, and subsequently developing with an alkaline solution of a member of the class consisting of hydroxylamine and hydrazine.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3117955A GB803783A (en) | 1955-11-01 | 1955-11-01 | Photographic materials |
| GB2930693X | 1956-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2930693A true US2930693A (en) | 1960-03-29 |
Family
ID=32396010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US619137A Expired - Lifetime US2930693A (en) | 1955-11-01 | 1956-10-30 | Photographic materials containing n-substituted phthalimide compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2930693A (enrdf_load_html_response) |
| BE (1) | BE552264A (enrdf_load_html_response) |
| DE (1) | DE1019560B (enrdf_load_html_response) |
| FR (1) | FR1159499A (enrdf_load_html_response) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1167650B (de) * | 1960-08-22 | 1964-04-09 | Polaroid Corp | Mehrschichtiges, fuer Mehrfarben-Diffusionsverfahren geeignetes photographisches Material mit Entwicklersubstanzen in der Emulsionsschicht |
| US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
| US4157915A (en) * | 1977-05-02 | 1979-06-12 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material containing development precursor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2137785A (en) * | 1936-10-09 | 1938-11-22 | Truecolour Film Ltd | Color photography and cinematography |
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2706157A (en) * | 1951-07-21 | 1955-04-12 | Grant Photo Products Inc | Processing photographic paper and film |
-
0
- BE BE552264D patent/BE552264A/xx unknown
-
1956
- 1956-10-30 US US619137A patent/US2930693A/en not_active Expired - Lifetime
- 1956-11-01 DE DEI12400A patent/DE1019560B/de active Pending
- 1956-11-02 FR FR1159499D patent/FR1159499A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2137785A (en) * | 1936-10-09 | 1938-11-22 | Truecolour Film Ltd | Color photography and cinematography |
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2706157A (en) * | 1951-07-21 | 1955-04-12 | Grant Photo Products Inc | Processing photographic paper and film |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
| DE1167650B (de) * | 1960-08-22 | 1964-04-09 | Polaroid Corp | Mehrschichtiges, fuer Mehrfarben-Diffusionsverfahren geeignetes photographisches Material mit Entwicklersubstanzen in der Emulsionsschicht |
| US4157915A (en) * | 1977-05-02 | 1979-06-12 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material containing development precursor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1019560B (de) | 1957-11-14 |
| BE552264A (enrdf_load_html_response) | |
| FR1159499A (fr) | 1958-06-27 |
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