US3615572A - Acidic solution of phenylenediamine color developer and sulfite - Google Patents
Acidic solution of phenylenediamine color developer and sulfite Download PDFInfo
- Publication number
- US3615572A US3615572A US676623A US3615572DA US3615572A US 3615572 A US3615572 A US 3615572A US 676623 A US676623 A US 676623A US 3615572D A US3615572D A US 3615572DA US 3615572 A US3615572 A US 3615572A
- Authority
- US
- United States
- Prior art keywords
- developing agent
- sulfite
- phenylenediamine
- amino
- developer
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000003929 acidic solution Substances 0.000 title abstract description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 55
- 239000000243 solution Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- -1 silver halide Chemical class 0.000 claims description 14
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- NPKFETRYYSUTEC-UHFFFAOYSA-N n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN(CC)C1=CC=C(N)C(C)=C1 NPKFETRYYSUTEC-UHFFFAOYSA-N 0.000 claims 1
- 150000004986 phenylenediamines Chemical class 0.000 abstract description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 28
- 235000010265 sodium sulphite Nutrition 0.000 description 14
- 238000011109 contamination Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004989 p-phenylenediamines Chemical class 0.000 description 3
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 3
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-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
- 239000003513 alkali Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 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
- 230000000694 effects Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 1
- FZIPCQLKPTZZIM-UHFFFAOYSA-N 2-oxidanylpropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O FZIPCQLKPTZZIM-UHFFFAOYSA-N 0.000 description 1
- SJSJAWHHGDPBOC-UHFFFAOYSA-N 4,4-dimethyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)CN1C1=CC=CC=C1 SJSJAWHHGDPBOC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- GHXRKGHKMRZBJH-UHFFFAOYSA-N boric acid Chemical compound OB(O)O.OB(O)O GHXRKGHKMRZBJH-UHFFFAOYSA-N 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000005022 packaging material Substances 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
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/264—Supplying of photographic processing chemicals; Preparation or packaging thereof
- G03C5/266—Supplying of photographic processing chemicals; Preparation or packaging thereof of solutions or concentrates
-
- 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
- Holter ABSTRACT The stability of acidic solutions of phenylenediamine compounds and sulfite is enhanced by controlling the phenylenediaminezsulfitc ratio.
- This invention relates to photographic developers.
- this invention relates to photographic color developers and compositions and processes used in the production thereof, especially wherein the color developer components are prepackaged in solution form for ready mixing and use by the trade.
- the minimum amount of sulfite useful in the acid solutions to retard aerial oxidation will vary somewhat depending inter alia upon the particular color developing agent in use since the p-phenylenediamines are oxidized at different rates, and upon the oxidizing agent such as air present in the solution.
- 4-amino-N)-ethyl-N-[fimethanesulfonamidoethyl]m toluidine especially useful results are obtained using more than about 0.08 mole of sulfite (e.g., about 10.l g.
- sodium sulfite i.e., the sO -containing moiety or moieties that are produced when various metallic (especially alkali metal) sulfites, bisulfites, sulfurous acid, etc. in combination or separately are added to water or water contion of the color developing agent.
- metallic (especially alkali metal) sulfites, bisulfites, sulfurous acid, etc. in combination or separately are added to water or water contion of the color developing agent.
- the maximum amount of sulfite desirable will also depend in part upon the particular color developing agent in use since the various p-phenylenediamines can be expected to be degraded at difierent rates.
- the amine-containing developing agents are referred to aboveas being free bases.
- Such amines are usually unstable in their free base form so theyare commonly sold as salts.
- 4-amino-N-ethyl-N-lfi-methanesulfonamidoethyll-m'toluidine is advantageously handled as a sesquisulfate monohydrate salt.
- the amino-containing moiety is the group which effects development.
- the mole ratios recited refer to the moles of amine as though the amine were in its free base state. 1
- Similar molar ratios of the other p-phenylenediamine color developing agents also give improved stability. Accordingly, in the acid solutions, from about 0.08 to 1.50 moles of sulfite per mole of p-phenylenediamine developing agent is useful to retard aerial oxidation and degradation of the color-developing agent.
- the weight ratio advantageously employed ranges about-from 0.1 -l.8 grams sodium sulfite: 3 grams of this developing agent.
- sodium sulfite is used as the sulfite source and 4-amino-3-methyl-N-ethyl-N-[B-hydroxyethyl]- aniline sulfate
- the silver halide developing agents especially useful in the acidic sulfite-containing solution are the p-phenylenediamine color developing agents well known in the art especially those forming nondiffusing dyes with phenolic and reactive methylene couplers.
- These developing agents include p-phenylenediamine and N,N-dialkyl-p-phenylenediamines wherein the alkyl groups or the aromatic nucleus may be substituted, for example: N,N-diethyl-p-phenylenediaminc monohydrochloride, 2-amino-S-diethylaminotoluene monohydrochloride, 4-amino-N-ethyl-N-[B-methanesulfoamidoethyll-m-toluidine sesquisulfate monohydrate; 4- amino-3-methyl-N-ethyl-N-[B-hydroxyethyl]-aniline sulfate,
- the solution be acidic to assist in the-stabilization of the developing agent and also to keep the developing agent in solution.
- the pH is preferably less than about 4. However, the optimum pH will vary depending upon the particular developing agent in use, for example, when 4- have a pH less than I particularly to keep the developing agent in solution in a concentrate.
- sulfite and color developing agents can be prepackaged in the same compartment with sulfite and color developing agents, for example, other substances useful in the color development reaction may 'be present such as antifoggants, e.g., benzotriazole, development restrainers, e.g., bromide and auxiliary black and white developing agents such as the 3-pyrazolidone silver halide developing agents, e.g., 4,4-dimethyl-l-phenyl-3- pyrazolidone.
- antifoggants e.g., benzotriazole
- development restrainers e.g., bromide and auxiliary black and white developing agents
- 3-pyrazolidone silver halide developing agents e.g., 4,4-dimethyl-l-phenyl-3- pyrazolidone.
- concentration of the sulfite and developing agent combined can vary widely. Since the developer package is designed for shipment and storage, it is usually desirable to utilize the highest concentration of ingredients which will readily stay in acid
- the stabilization effect obtained by controlling the ingredient ratio as indicated above is generally advantageous in any acidic solution which contains both a p-phenylenediamine and sulfite. Maintaining the ratio is especially significant in photographic silver halide developer packages which are to be utilized with well known color products having differently sensitized silver halide emulsion layers containing nondiffusing coupler compounds.
- a color product is used of the type having superposed on a support, blue, green and red sensitized emulsion layers containing yellow, magenta and cyan dye forming couplers, respectively, the mentioned degradation of the color developing agent in the presence of excess sulfite results, for example, in magenta dye appearing of the yellow color scale.
- THe developer compositions when mixed and ready for use can and desirably do contain the usual amounts of developing agent, sulfite and alkali as disclosed generally in the Jelley et al. US Pat. No. 2,322,027.
- packaged developer components must be separated to the extent that in compartments containing developing agents, the s'ulfite concentration and the pH is controlled as previously indicated.
- Other components which may form part of the mixed developer package for example, additional sulfite, accelerators, complexing agents, buffers, e.g., citric acid-citrate, boric acid-borate, etc. are advantageously contained in the compartment containing the alkali, e.g., potassium hydroxide, although placing selected addenda in other or separate compartments may be desirable depending upon the particular ingredient chosen.
- the packaged developed effectively may be a single package, for example, an outside container or cardboard box in which the developer components are compartmentalized.
- the compartments can be an integral part of the exterior packaging material but advantageously are, at least in part, merely bottles of, for example, glass and/or plastic enclosed in the outside container.
- the choice of sizes and shapes of the bottles which form the compartments can vary with the selected ingredients, concentrations desired, etc. Usually it is desirable to choosethe bottle size, shape, etc. which will result in a total package of minimum size and weight to minimize shipping and storage costs. As a result, it may in some instances be desirable to place a single component type in a plurality of compartments, e.g., to conserve space.
- Example 1-Unstable package A developer kit containing separate bottles respectively containing:
- *4-umino-N-ethyl-N-[B-methanesullbnumidoethylj-m-toluidine sesquisulfate monohydrate is stored at room temperature for about 6 months or at elevated temperatures (e.g., 90-120 F.) for shorter periods of time.
- the solutions are then added to sufficient water (about 70 F.) to make one liter.
- the solution is then utilized as the developer for a photographic color print material having respectively superposed on a paper support, blue, green and red sensitized emulsion layers containing yellow. magenta and cyan dye-forming couplers respectively which has been exposed to a test pattern. After general processing otthe photographic clement using the developer mentioned above. the test pattern shows serious magenta contamination of the areas which should have appeared yellow.
- EXAMPLE 2 A developer kit containing separate bottles respectively containing:
- the developer kit of example 2, Part B can further be modified by replacing sodium hexametaphosphate by other calcium sequestering agents, such as amino polyacetic acids, e.g., diaminopropanol tetraacetic acid, ethylenediamine tetraacetic acid, nitrilo triacetic acid, etc., sodium carbonate added as a buffer. 7
- amino polyacetic acids e.g., diaminopropanol tetraacetic acid, ethylenediamine tetraacetic acid, nitrilo triacetic acid, etc.
- EXAMPLE 3 A developer kit containing separate bottles respectively containing:
- EXAMPLE 5 The procedure according to example 3 is followed except that 4-amino-3-(B-methylsulfonamidoethyl)-N,N- diethylaniline hydrochloride is utilized as the color developing agent. No detectable magenta contamination appears in the yellow areas.
- EXAMPLE 6 A developer kit containing separate bottles respectively containing:
- EXAMPLE 7 The process of example 6 is carried out in the identical manner except using 0.6 g. of sodium sulfite in part D and 1.5 g. in part B. As a result, no detectable magenta contamination appears in the yellow areas.
- EXAMPLE 8 The process of example 6 is carried out in the identical manner except using 0.8 g. of sodium sulfite in part D and 1.3 g. in part B. As a result, slight magenta contamination appears in the yellow areas but marked improvement over that of example 1.
- EXAMPLE 9 The process of example 6 is carried out in the identical manner except using 1.0 g. of sodium sulfite in part D and 1.1 g. in part B. As a result, slight detectable magenta contamination appears in the yellow areas but marked improvement over that ofexample 1.
- EXAMPLE 10 The process of example 6 is carried out in the identical manner except using 1.2 g. of sodium sulfite in part D and 0.9 g. in part B. As a result, slight detectable magenta contamination appears in the yellow areas but marked improvement over that of example 1
- EXAMPLE 11 The process of example 6 is carried out in the identical manner except using 1.4 g. of sodium sulfite in part D and 0.7 g. in part B. As a result, magenta contamination appears in the yellow areas but there is improvement over that of example 1.
- EXAMPLE 12 The process of example 6 is carried out in the identical manner except using 1.6 g. of sodium sulfite in part D and 0.5 g. in part B. As a result, magenta contamination appears in the yellow areas but there is improvement over that of example 1.
- EXAMPLE 13 The process of example 6 is carried out in the identical g. in part B. Magenta contamination appears in the yellow areas but there is improvement over that ofexample 1.
- An acidic aqueous solution of pH less than about 4 comprising at least one phenylenediamine silver halide developing agent and an amount of sulfite sufficient to retard aerial oxidation of said developing agent and insufficient to cause significant degradation of said latter developing agent upon aging of said solution, the mole ratio of said developing agent to sulfite being about 1 to 0.08 -1.5.
- aqueous solution contains at least one N,N-dialkyl-p-phenylenediamine silver halide developing agent.
- N,N-dialkylp-phenylenediamine silver halide developing agent contains el k ls eemie w 4.
- the developing agent is at least one developing agent selected from the group consisting of N,N-diethyl-p-phenylenediamine, 2-amino-5- diethylaminotoluene, 4-amino-N-ethyl-N-[B-methane-sulfonamidoethyl]-m-toluidine, 4-amino-3-methyl-N-ethyl-N-[B- hydroxyethyl]-aniline, 4-amino-3-(p-methylsulfonamidoethyl)-N,N-diethylaniline, or 4-amino-N,N-diethyl- 3-(N'-methyl-/3-methy1sulfonamidoethyl)-ani
- a method for the production of a photographic silver halide developer composition comprising combining (1) an acidic aqueous solution pH less than about 4 comprising p-
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67662367A | 1967-10-19 | 1967-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3615572A true US3615572A (en) | 1971-10-26 |
Family
ID=24715266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US676623A Expired - Lifetime US3615572A (en) | 1967-10-19 | 1967-10-19 | Acidic solution of phenylenediamine color developer and sulfite |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3615572A (fr) |
| BE (1) | BE722299A (fr) |
| BR (1) | BR6803182D0 (fr) |
| CA (1) | CA939551B (fr) |
| CH (1) | CH489834A (fr) |
| FR (1) | FR1588394A (fr) |
| GB (1) | GB1244623A (fr) |
| IT (1) | IT845033A (fr) |
| NL (1) | NL164137C (fr) |
| SE (1) | SE357631B (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3790381A (en) * | 1971-09-24 | 1974-02-05 | Minnesota Mining & Mfg | Alkaline photographic developer concentrate |
| US4501812A (en) * | 1983-02-10 | 1985-02-26 | Minnesota Mining And Manufacturing Company | Photographic color developer composition packaged in two or more concentrated parts, particularly solutions, and concentrated color developer water solution |
| US4719660A (en) * | 1986-11-17 | 1988-01-19 | Hopkins Manufacturing Corporation | Ice scraper |
| EP0636937A1 (fr) | 1993-07-28 | 1995-02-01 | Chugai Photo Chemical Co. Ltd. | Composition contenant un agent développateur pour la couleur, révélateur pour le traitement de matériaux photographiques couleur à l'halogénure d'argent et méthode à cet effet |
| EP0793141A2 (fr) | 1996-02-29 | 1997-09-03 | Chugai Photo Chemical Co. Ltd. | Composition contenant un agent développateur pour la couleur et procédé de traitement d'un matériau photographique à l'halogénure d'argent |
| US6361820B1 (en) | 1999-01-07 | 2002-03-26 | Honeywell International Inc. | Dielectric films from organohydridosiloxane resins with high organic content |
-
0
- IT IT845033D patent/IT845033A/it unknown
-
1967
- 1967-10-19 US US676623A patent/US3615572A/en not_active Expired - Lifetime
-
1968
- 1968-10-01 CH CH1466368A patent/CH489834A/fr not_active IP Right Cessation
- 1968-10-14 BE BE722299D patent/BE722299A/xx not_active IP Right Cessation
- 1968-10-16 FR FR1588394D patent/FR1588394A/fr not_active Expired
- 1968-10-16 BR BR203182/68A patent/BR6803182D0/pt unknown
- 1968-10-17 NL NL6814905.A patent/NL164137C/xx not_active IP Right Cessation
- 1968-10-18 GB GB49513/68A patent/GB1244623A/en not_active Expired
- 1968-10-21 SE SE14183/68A patent/SE357631B/xx unknown
-
1973
- 1973-04-05 CA CA167,984A patent/CA939551B/xx not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3790381A (en) * | 1971-09-24 | 1974-02-05 | Minnesota Mining & Mfg | Alkaline photographic developer concentrate |
| US4501812A (en) * | 1983-02-10 | 1985-02-26 | Minnesota Mining And Manufacturing Company | Photographic color developer composition packaged in two or more concentrated parts, particularly solutions, and concentrated color developer water solution |
| EP0118693B1 (fr) * | 1983-02-10 | 1988-08-10 | Minnesota Mining And Manufacturing Company | Concentré pour révélateur photographique en couleur conditionné en deux ou plusieurs unités d'emballage en particulier de solutions, et solutions aqueuses concentrées pour révélateurs |
| US4719660A (en) * | 1986-11-17 | 1988-01-19 | Hopkins Manufacturing Corporation | Ice scraper |
| EP0636937A1 (fr) | 1993-07-28 | 1995-02-01 | Chugai Photo Chemical Co. Ltd. | Composition contenant un agent développateur pour la couleur, révélateur pour le traitement de matériaux photographiques couleur à l'halogénure d'argent et méthode à cet effet |
| EP0793141A2 (fr) | 1996-02-29 | 1997-09-03 | Chugai Photo Chemical Co. Ltd. | Composition contenant un agent développateur pour la couleur et procédé de traitement d'un matériau photographique à l'halogénure d'argent |
| US6361820B1 (en) | 1999-01-07 | 2002-03-26 | Honeywell International Inc. | Dielectric films from organohydridosiloxane resins with high organic content |
Also Published As
| Publication number | Publication date |
|---|---|
| CA939551B (en) | 1974-01-08 |
| GB1244623A (en) | 1971-09-02 |
| NL164137B (nl) | 1980-06-16 |
| NL164137C (nl) | 1980-11-17 |
| DE1803928A1 (de) | 1969-07-31 |
| BE722299A (fr) | 1969-03-14 |
| SE357631B (fr) | 1973-07-02 |
| FR1588394A (fr) | 1970-04-10 |
| BR6803182D0 (pt) | 1973-01-18 |
| CH489834A (fr) | 1970-04-30 |
| NL6814905A (fr) | 1969-04-22 |
| IT845033A (fr) |
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