US3723118A - Diffusion transfer process for photographic silver halide emulsion - Google Patents
Diffusion transfer process for photographic silver halide emulsion Download PDFInfo
- Publication number
- US3723118A US3723118A US00150932A US3723118DA US3723118A US 3723118 A US3723118 A US 3723118A US 00150932 A US00150932 A US 00150932A US 3723118D A US3723118D A US 3723118DA US 3723118 A US3723118 A US 3723118A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- transfer process
- diffusion transfer
- group
- photographic silver
- 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 abstract description 33
- 229910052709 silver Inorganic materials 0.000 title abstract description 23
- 239000004332 silver Substances 0.000 title abstract description 23
- -1 silver halide Chemical class 0.000 title abstract description 22
- 238000012546 transfer Methods 0.000 title abstract description 18
- 238000009792 diffusion process Methods 0.000 title abstract description 17
- 239000000839 emulsion Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 238000012545 processing Methods 0.000 abstract description 22
- 150000003839 salts Chemical class 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 2
- UEUIKXVPXLWUDU-UHFFFAOYSA-O 4-sulfobenzenediazonium Chemical compound OS(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-O 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RMXNSQWYMVTLEU-UHFFFAOYSA-N 2,6-bis(prop-2-enyl)phenol Chemical compound OC1=C(CC=C)C=CC=C1CC=C RMXNSQWYMVTLEU-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- VJBNTMUSFMRWSH-UHFFFAOYSA-N 3,5-dimethyl-2-prop-2-enylphenol Chemical compound CC1=CC(C)=C(CC=C)C(O)=C1 VJBNTMUSFMRWSH-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- XPAZGLFMMUODDK-UHFFFAOYSA-N 6-nitro-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N=CNC2=C1 XPAZGLFMMUODDK-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000552 p-cresyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1O*)C([H])([H])[H] 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 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 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/04—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
- G03C8/06—Silver salt diffusion transfer
-
- 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
- G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring
Definitions
- the present invention relates to a process for processing an exposed photographic silver halide light-sensitive material. More particularly, the present invention relates to a process for processing exposed silver halide photographic material by diffusion transfer process.
- a latent image formed in a negative emulsion layer by imagewise exposure is developed and, simultaneously, a residual unexposed silver halide, i.e., undeveloped silver halide, in the negative emulsion layer, is reacted with a silver halide solvent to form a soluble silver complex in an amount corresponding to the amount of the exposure.
- soluble, silver complex is reduced in a print-receiving layer which is brought into contact with the exposed silver halide emulsion layer and contains a suitable silver precipitating layer, whereby the reduced silver is precipitated to give the desired positive image.
- An object of the present invention is to prepare a processing solution for a high speed diffusion transfer process, which is suitable for forming satisfactory images from a silver halide emulsion exposed to a small quantity of light, for example, of exposure index ASA 1,000.
- the processing solution to be employed in the diffusion transfer process according to the present invention is a viscous liquid which is uniformly spread between the negative and positive layers, and develops a latent image in the silver halide emulsion layer, even when formed by a small quantity of exposure index more than ASA 1,000, followed by the same step as above to form positive images. Moreover, it is desirable to finish the processings to form the positive image within short periods of time, that is, within 1 minute.
- An object of the present invention is to prepare a processing solution for use in a high speed diffusion transfer process which is suitable for the purpose of forming a satisfactory positive image from a silver halide emulsion which has been exposed to small quantities of light, for ixgrple, to light showing an exposure index of ASA More particularly, this invention provides highly active developing agents suitable for use in processing solutions employed in the above-described high speed diffusion transfer process.
- X is a lower alkenyl or a lower alkenoxy group
- R is hydrogen or a lower alkyl group
- R R and R each is hydrogen, a lower alkyl group, a lower alkenyl group, or a lower alkoxy group, the term lower indicating that the total number of carbon atoms is not more than 4.
- the compounds of the above-described formula to be employed according to the present invention may be used in either the form of a free amine, as shown by the general formula itself, or in the more stable form of acid addition salts, such as sulfates and hydrochlorides.
- the images obtained by the high speed diffusion transfer process using, as a developing agent, a compound of the above-described general formula can yield a satisfactory positive image.
- the compounds represented by the general formula are very soluble in water. Since a quantity of the highly active developing agent is to be employed in the process ng solution of the high speed diffusion transfer process, the great solubility in water can be extremely advantageous.
- the compounds of the general formula may be used singly as highly active developing agents or may be used together with other reducing agents, such as phenols, such as cresol, and hydroxylamines, such as N,N-diethylhydroxylamine.
- Synthesis 1 (4-amino-2-allylphenol hydrochloride) While a solution consisting of 97 g. of sulfanilic acid, 39.2 g. of sodium carbonate monohydrate and 1 liter of water was maintained at 8 C., 168 ml. of concentrated hydrochloric acid and then 40.6 g. of sodium nitrite dissolved in a small amount of water were added to obtain a reaction mixture containing White diazonium salt.
- the resulting mixture was added to a solution composed of 112 g. of caustic soda, 164 g. of sodium carbonate monohydrate, 75 g. of 2-allylphenol and 2 liters of water with stirring, wherein the temperature of the reaction mixture should be kept below C. in a water bath. After the addition, the water bath was removed and, after stirring for an hour, 400 g. of sodium hydrosulfite was added thereto followed by heating to 70 C. to provide precipitated white crystals of the amine. After cooling, the crystalline amine was collected and converted into its hydrochloride, whereby 67 g. of 4-amino-2-allylphenyl hydrochloride, as colorless crystals having a melting point of from 177 to 190 C. (decomposed), was obtained in a yield of 64.4%.
- Synthesis 2 (4-amino-2,fi-diallylphenol hydrochloride)
- 2,6-diallylphenol was coupled with a diazonium salt of sulfanilic acid followed by treatment with sodium hydrosulfite.
- the resulting amine was converted into its hydrochloride to obtain the desired product, as colorless needles having a melting point of from 125 to 165 C. (decomposed), in a yield of 51.0%.
- Synthesis 3 (4-amino-2-allyl-3,5-dimethylphenol hydrochloride)
- 2-allyl-3,5-dimethylphenol was coupled with a diazonium salt of sulfanilic acid followed by treatment with sodium hydrosulfite.
- the resulting amine was formed into its hydrochloride to obtain the desired product as colorless crystals having a melting point of from 236 to 237 C. in a yield of 55.1%.
- the developing agents represented by the general formula are very useful as developing agents in the silver salt diffusion transfer process.
- the negative materials employed in the invention may be film or paper having coated thereon black-white negative emulsions intended for use in usual photography or negative emulsions for use in X-ray photography. These negative emulsions contain silver halide, such as silver iodobromide, which may be spectrally and/or chemically sensitized.
- the positive materials are composed of a film or paper having coated thereon a layer containing nuclei of physical development. Among such positive materials is, for example, a Positive Paper for Neo-Copy made by Fuji Photo Film Co., Ltd.
- the print-receiving layer was stripped to obtain a positive image of satisfactory gradation.
- Example 1 was repeated, except that compound (4) was employed as the hydrochloride in place of compound (1).
- Example 2 was repeated, except that compound (4) was employed as the hydrochloride in place of compound (1).
- Example 3 was repeated, except that compound (4) was employed as the hydrochloride in place of compound (1).
- a high speed difi'usion transfer process which comprises processing an exposed photographic silver halide material with a processing solution containing a compound represented by the following general formula or acid salt thereof:
- X is a lower alkenyl or a lower alkenoxy group
- R is hydrogen, or a lower alkyl group
- R R and R each is hydrogen, a lower alkyl group, a lower alkenyl group or a lower alkoxy group, in which the term lower indicates that the total number of carbon atoms is not more than 4.
- processing solution contains an alkaline agent, an antifoggant and/or viscosity-increasing agent thickeners.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45049338A JPS492624B1 (enrdf_load_stackoverflow) | 1970-06-08 | 1970-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3723118A true US3723118A (en) | 1973-03-27 |
Family
ID=12828193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00150932A Expired - Lifetime US3723118A (en) | 1970-06-08 | 1971-06-08 | Diffusion transfer process for photographic silver halide emulsion |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3723118A (enrdf_load_stackoverflow) |
| JP (1) | JPS492624B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2128497A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1309365A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298673A (en) * | 1972-03-10 | 1981-11-03 | Fuji Photo Film Co., Ltd. | Lithographic type diffusion transfer developing composition |
| WO1995017877A1 (de) * | 1993-12-24 | 1995-07-06 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von allylaminophenolen in oxidationsfärbemitteln |
| US20080277084A1 (en) * | 2007-05-09 | 2008-11-13 | Buckman Laboratories International, Inc. | ASA Sizing Emulsions For Paper and Paperboard |
-
1970
- 1970-06-08 JP JP45049338A patent/JPS492624B1/ja active Pending
-
1971
- 1971-06-04 GB GB1908471*[A patent/GB1309365A/en not_active Expired
- 1971-06-08 DE DE19712128497 patent/DE2128497A1/de active Granted
- 1971-06-08 US US00150932A patent/US3723118A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298673A (en) * | 1972-03-10 | 1981-11-03 | Fuji Photo Film Co., Ltd. | Lithographic type diffusion transfer developing composition |
| WO1995017877A1 (de) * | 1993-12-24 | 1995-07-06 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von allylaminophenolen in oxidationsfärbemitteln |
| US20080277084A1 (en) * | 2007-05-09 | 2008-11-13 | Buckman Laboratories International, Inc. | ASA Sizing Emulsions For Paper and Paperboard |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2128497B2 (enrdf_load_stackoverflow) | 1974-03-28 |
| GB1309365A (en) | 1973-03-07 |
| DE2128497A1 (de) | 1971-12-23 |
| JPS492624B1 (enrdf_load_stackoverflow) | 1974-01-22 |
| DE2128497C3 (enrdf_load_stackoverflow) | 1974-10-31 |
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