US2843481A - Photographic processes - Google Patents
Photographic processes Download PDFInfo
- Publication number
- US2843481A US2843481A US444365A US44436554A US2843481A US 2843481 A US2843481 A US 2843481A US 444365 A US444365 A US 444365A US 44436554 A US44436554 A US 44436554A US 2843481 A US2843481 A US 2843481A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- silver
- image
- hydroxy
- developing
- 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
- 238000000034 method Methods 0.000 title claims description 24
- 229910052709 silver Inorganic materials 0.000 claims description 34
- 239000004332 silver Substances 0.000 claims description 34
- -1 SILVER HALIDE Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B30/00—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images
- G02B30/20—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes
- G02B30/22—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type
- G02B30/25—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type using polarisation techniques
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3014—Hydrazine; Hydroxylamine; Urea; Derivatives thereof
-
- 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
- G03C7/22—Subtractive cinematographic processes; Materials therefor; Preparing or processing such materials
- G03C7/25—Dye-imbibition processes; Materials therefor; Preparing or processing such materials
-
- 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
- G03C9/00—Stereo-photographic or similar processes
- G03C9/04—Vectographic-image
Definitions
- This invention relates to photography and, more particularly, to compositions and processes useful in the development of photosensitive silver halide elements.
- a further object of the present invention is to provide novel chemical compounds capable of developing silver halide emulsions.
- the invention accordingly comprises the several steps and the relation and order of one or more of such steps with respect to each of the others, and the compositions possessing the features, properties and the relation of elements which are exemplified in the following detailed disclosure, and the scope of the application of which will be indicated in the claims.
- heterocyclic N-hydroxylamines and their salts are effective to develop exposed silver halide emulsions. These compounds contain at least one nitrogen in the ring, are monocyclic and may also contain oxygen in the ring.
- the preferred heterocyclic N-hydroxylamines are N-hydroxy morpholine, N- hydroxy piperidine and N-hydroxy pyrrolidine, and their salts.
- novel photographic developing agents of this invention may be prepared as follows:
- Example 1 Molecular equivalents of pyrolidine and 6% hydrogen peroxide are allowed to stand together at room temperature for 20-24 hours. The solution is then extracted with ether, the ether extract dried, and the ether distilled off. The residue is vacuum fractionated to yield N-hydroxy pyrrolidine. The product boils at 74-76" C. at a pressure of 25 mm. and is soluble in alcohol, ether and alkali and moderately soluble in Water.
- Example 2 N-hydroxy morpholine is prepared by allowing morpholine and hydrogen peroxide to react in a manner similar to that set forth in Example 1. The product is soluble in alcohol, ether and alkali, moderately soluble in water, and boils at 76-79 C. at a pressure of 3 mm.
- Example 3 Nhydroxy piperidine is prepared by allowing piperidine and hydrogen peroxide to react in a manner similar to that described in Example 1.
- the product is soluble in alkali, alcohol and ether, moderately soluble in water, boils at 75-80 C. at a pressure of 18 mm. and melts at 3236 C.
- This developer composition fully develops a latent image present in a photosensitive silver halide emulsion, such as Kodak Verichrome, in about 5-8 minutes.
- the relative proportions of the novel developing agents and the other ingredients of the above developer composition may be varied to suit the requirements of the operator.
- modify the above developer composition by the substitution of preservatives or alkalies other than those specifically mentioned.
- the above developer composition may be modified by the inclusion of other common components of developer compositions, such as restrainers, accelerators, etc.
- novel developing agents herein disclosed are colorless, stain-free, stable and relatively nonvolatile (especially in the salt form) and give black silver deposits on development. They may be employed in the form of the free base or as acid salts thereof, such as the oxalate.
- the salt form may be employed where the developing agent is to be incorporated in, on or behind the emulsion, or Where one desires to prepare a dry leveloper composition, the solvent being added to the dry composition prior to use.
- Reference in this specification and in the claims to the developing agents in the form of the free base are therefore intended also to include instances where the developing agent is introduced as a salt.
- an alkaline solution will contain the free base even though it may have been initially added as a salt.
- heterocyclic N-hyclroxylamines of this invention are also useful as developing agents in diffusion-transfer reversal processes, both dye and silver, and are especially useful in such photographic processes wherein it is desired to eliminate or minimize the need for washing or stabilizing operations in liquid baths subsequent to the formation of the silver print. Examples of such processes are disclosed in U. S. Patent No. 2,647,056 to Edwin H. Land.
- the utility of the developers of this invention is by no means limited to diffusiontransfer reversal processes, for they may be satisfactorily employed in conventional multistage and multibath photoglraphic processing procedures either in black-andwhile or color photography.
- a method of developing a silver halide emulsion which comprises treating an exposed silver halide emulsion containing a latent image with an aqueous solution containing an alkaline material and a compound selected from the group consisting of N-hydroxy morpholine, N- hydroxy pyrrolidine and N-hydrox'y piperidine for a sufficient time to develop the latent image to a silver image.
- a method of developing a silver halide emulsion which comprises treating an exposed silver halide emulsion containing a latent image with an aqueous solution containing an alkaline material and N-hydroxy pyrrolidine for a suflicient time to develop the latent image to a silver image.
- a method of developing a silver halide emulsion which comprises treating an exposed silver halide emulsion containing a latent image with an aqueous solution containing an alkaline material and N -hydroXy piperidine for a sufficient time to develop the latent image to a silver image.
- N- hydroXyl heterocyclic amine is selected from the group consisting of N-hydroxy morpholine, N-hydroxy pyrorolidine and N-hydroxy piperidine.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Polarising Elements (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US444365A US2843481A (en) | 1954-07-19 | 1954-07-19 | Photographic processes |
| US444074A US2868077A (en) | 1954-07-19 | 1954-07-19 | Film stock for dichroic dye images |
| GB17383/55A GB782217A (en) | 1954-07-19 | 1955-06-16 | Improvements relating to film stock for dichroic dye images |
| FR1134839D FR1134839A (fr) | 1954-07-19 | 1955-07-18 | Perfectionnements à un film vierge pour l'obtention d'images à colorants ou teintures dichroïques |
| DEI10447A DE1031637B (de) | 1954-07-19 | 1955-07-18 | Filmmaterial fuer dichroitische Farbbilder |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US444365A US2843481A (en) | 1954-07-19 | 1954-07-19 | Photographic processes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2843481A true US2843481A (en) | 1958-07-15 |
Family
ID=23764591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US444365A Expired - Lifetime US2843481A (en) | 1954-07-19 | 1954-07-19 | Photographic processes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2843481A (de) |
| DE (1) | DE1031637B (de) |
| FR (1) | FR1134839A (de) |
| GB (1) | GB782217A (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362961A (en) * | 1963-06-26 | 1968-01-09 | Polaroid Corp | N-substituted hydroxylamines |
| JPS62212363A (ja) * | 1986-03-11 | 1987-09-18 | Sumitomo Chem Co Ltd | ヒドロキサム酸化合物およびその製造法 |
| US5618652A (en) * | 1995-03-22 | 1997-04-08 | Fuji Photo Film Co., Ltd. | Image formation method by silver salt diffusion transfer |
| WO2003106390A1 (en) * | 2002-06-13 | 2003-12-24 | A H Marks & Company Limited | Polymerisation inhibitor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE581344A (de) * | 1959-08-04 | |||
| US3388994A (en) * | 1967-02-20 | 1968-06-18 | Polaroid Corp | Photographic image-receiving elements having been treated with ammonia after drying |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1658177A (en) * | 1923-06-04 | 1928-02-07 | Sulzberger Nathan | Photography |
| US1937844A (en) * | 1931-03-23 | 1933-12-05 | Goodrich Co B F | Photographic developer and method of developing |
| US2030336A (en) * | 1932-12-24 | 1936-02-11 | Agfa Ansco Corp | Photographic developer |
| US2550617A (en) * | 1946-06-06 | 1951-04-24 | Fr Corp | Fine grain photographic developer containing morpholine |
| US2623880A (en) * | 1948-12-10 | 1952-12-30 | Hopff Heinrich | N-(beta-n'-phenyl-n'-benzylaminoethyl) pyrrolidine |
| US2648673A (en) * | 1950-10-10 | 1953-08-11 | Monsanto Chemicals | Nu-thio pyrrolidines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE656293C (de) * | 1934-12-15 | 1938-02-02 | Friedrich Lierg Dr Ing | Blankpapier fuer den Absaugedruck |
| BE465036A (de) * | 1940-06-07 | |||
| US2289715A (en) * | 1940-06-07 | 1942-07-14 | Polaroid Corp | Composite film for receiving stereoscopic prints |
| US2315373A (en) * | 1941-05-28 | 1943-03-30 | Polarold Corp | Process for forming light-polarizing images |
-
1954
- 1954-07-19 US US444365A patent/US2843481A/en not_active Expired - Lifetime
-
1955
- 1955-06-16 GB GB17383/55A patent/GB782217A/en not_active Expired
- 1955-07-18 DE DEI10447A patent/DE1031637B/de active Pending
- 1955-07-18 FR FR1134839D patent/FR1134839A/fr not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1658177A (en) * | 1923-06-04 | 1928-02-07 | Sulzberger Nathan | Photography |
| US1937844A (en) * | 1931-03-23 | 1933-12-05 | Goodrich Co B F | Photographic developer and method of developing |
| US2030336A (en) * | 1932-12-24 | 1936-02-11 | Agfa Ansco Corp | Photographic developer |
| US2550617A (en) * | 1946-06-06 | 1951-04-24 | Fr Corp | Fine grain photographic developer containing morpholine |
| US2623880A (en) * | 1948-12-10 | 1952-12-30 | Hopff Heinrich | N-(beta-n'-phenyl-n'-benzylaminoethyl) pyrrolidine |
| US2648673A (en) * | 1950-10-10 | 1953-08-11 | Monsanto Chemicals | Nu-thio pyrrolidines |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362961A (en) * | 1963-06-26 | 1968-01-09 | Polaroid Corp | N-substituted hydroxylamines |
| JPS62212363A (ja) * | 1986-03-11 | 1987-09-18 | Sumitomo Chem Co Ltd | ヒドロキサム酸化合物およびその製造法 |
| US5618652A (en) * | 1995-03-22 | 1997-04-08 | Fuji Photo Film Co., Ltd. | Image formation method by silver salt diffusion transfer |
| WO2003106390A1 (en) * | 2002-06-13 | 2003-12-24 | A H Marks & Company Limited | Polymerisation inhibitor |
| US20060167244A1 (en) * | 2002-06-13 | 2006-07-27 | Emyr Philips | Polymerisation inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1134839A (fr) | 1957-04-18 |
| DE1031637B (de) | 1958-06-04 |
| GB782217A (en) | 1957-09-04 |
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