GB545444A - Improvements in or relating to primary aromatic hydrazine solutions and to the use of such solutions in photographic processes - Google Patents
Improvements in or relating to primary aromatic hydrazine solutions and to the use of such solutions in photographic processesInfo
- Publication number
- GB545444A GB545444A GB15343/40A GB1534340A GB545444A GB 545444 A GB545444 A GB 545444A GB 15343/40 A GB15343/40 A GB 15343/40A GB 1534340 A GB1534340 A GB 1534340A GB 545444 A GB545444 A GB 545444A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solution
- added
- long chain
- hydrazine
- per cent
- 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
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title abstract 10
- 125000003118 aryl group Chemical group 0.000 title abstract 3
- 239000000243 solution Substances 0.000 abstract 11
- 239000002253 acid Substances 0.000 abstract 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 6
- -1 hydrocarbon radical Chemical class 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229960003237 betaine Drugs 0.000 abstract 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- XBCIOBSQHJYVBQ-UHFFFAOYSA-N naphthalen-1-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=CC2=C1 XBCIOBSQHJYVBQ-UHFFFAOYSA-N 0.000 abstract 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 abstract 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 2
- 229940067157 phenylhydrazine Drugs 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 1
- WBMWGMDZEAONHM-UHFFFAOYSA-N 1-bromo-1-naphthalen-1-ylhydrazine Chemical class BrN(N)C1=CC=CC2=CC=CC=C12 WBMWGMDZEAONHM-UHFFFAOYSA-N 0.000 abstract 1
- NBXGIIMMSBYDKU-UHFFFAOYSA-N 1-bromo-1-phenylhydrazine Chemical class NN(Br)C1=CC=CC=C1 NBXGIIMMSBYDKU-UHFFFAOYSA-N 0.000 abstract 1
- PGSFPEKGAPZEEU-UHFFFAOYSA-N 1-chloro-1-naphthalen-1-ylhydrazine Chemical class ClN(N)C1=CC=CC2=CC=CC=C12 PGSFPEKGAPZEEU-UHFFFAOYSA-N 0.000 abstract 1
- UMKLWBFJFMDZAH-UHFFFAOYSA-N 1-chloro-1-phenylhydrazine Chemical class NN(Cl)C1=CC=CC=C1 UMKLWBFJFMDZAH-UHFFFAOYSA-N 0.000 abstract 1
- LFPDULKFWCXVIV-UHFFFAOYSA-N 1-methoxy-1-phenylhydrazine Chemical class CON(N)C1=CC=CC=C1 LFPDULKFWCXVIV-UHFFFAOYSA-N 0.000 abstract 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 abstract 1
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000021360 Myristic acid Nutrition 0.000 abstract 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 229910021607 Silver chloride Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- ZWWXDCOPVYATOQ-UHFFFAOYSA-N amino-(4-nitrophenyl)azanium;chloride Chemical compound [Cl-].N[NH2+]C1=CC=C([N+]([O-])=O)C=C1 ZWWXDCOPVYATOQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- JYYDHGMTXHCSKZ-UHFFFAOYSA-N ethyl 4-hydrazinylbenzoate Chemical class CCOC(=O)C1=CC=C(NN)C=C1 JYYDHGMTXHCSKZ-UHFFFAOYSA-N 0.000 abstract 1
- 159000000011 group IA salts Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- XGFJCRNRWOXGQM-UHFFFAOYSA-N hot-2 Chemical compound CCSC1=CC(OC)=C(CCNO)C=C1OC XGFJCRNRWOXGQM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000001165 hydrophobic group Chemical group 0.000 abstract 1
- 229940045996 isethionic acid Drugs 0.000 abstract 1
- 235000020778 linoleic acid Nutrition 0.000 abstract 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- LGROKZMEHJZWDU-UHFFFAOYSA-N n-amino-n-phenylnitramide Chemical class [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 abstract 1
- 229940038384 octadecane Drugs 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 125000005498 phthalate group Chemical class 0.000 abstract 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 229910000162 sodium phosphate Inorganic materials 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 229960003080 taurine Drugs 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 abstract 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
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3014—Hydrazine; Hydroxylamine; Urea; Derivatives thereof
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Paper (AREA)
Abstract
545,444. Photographic developing solutions. DU PONT FILM MANUFACTURING CORPORATION. Oct. 16, 1940, No. 15343. Convention date, Oct. 16, 1939. [Class 98 (ii)] An aqueous solution of a primary aromatic hydrazine is produced by dissolving the hydrazine or a mineral acid salt thereof in a aqueous solution that contains as a solubilizing agent a surface-active polar compound containing a hydrophobic group comprising an open-chain hydrocarbon radical of at least eight carbon atoms. The hydrazine may be added to an aqueous medium having a pH value of approximately 7 or greater, followed by the addition of a 2 per cent solution of the solubilizing agent so that the concentration of the solubilizing agent is less than one per cent, and heating until solution is complete. Alternatively a mineral acid salt (such as the hydrochloride or sulphate) of the hydrazine is dissolved in water, a 2 per cent solution of the solubilizing agent is added, and the mixture heated while an alkaline solution is added until the desired pH (approximately 7 or greater) is reached. The solution may be used as a photographic developing solution for latent, re-halogenized, or reversed images in silver chloride or bromide emulsions. Hydrazines referred to are phenylhydrazine, nitrophenylhydrazines such as p-nitrophenylhydrazine, α- naphthylhydrazine, tolylhydrazines, bromophenylhydrazines, chlorophenylhydrazines, chloronaphthylhydrazines, bromonaphthylhydrazines, p-diphenylhydrazine, p:p<SP>1</SP>diphenyldihydrazines, methoxyphenylhydrazines, and p-carbethoxyphenylhydrazines. Antifoamants such as hexyl alcohol, hexylacetate, octyl alcohol, octylacetate, and 2-ethylhexyl acetate, and alkaline salts such as carbonates, sulphites, phosphates, acetates, phthalates, and citrates, or bases such as alkali hydroxides, ammonia, and amines may be added. Solubilizing agents specified are the watersoluble salts of the long chain aliphatic carboxylic or sulphonic acids, the long chain aliphatic sulphates, mineral oil sulphonates, long chain alkylated aromatic sulphonic acids, and long chain aliphatic hydrocarbon substituted betaines. Particular examples are the water-soluble alkali metal, ammonium, and amine (such as methyl- and ethyl-amine and mono-, di-, and tri-ethanolamine) salts of stearic, palmitic, oleic, arachidic, oleostearic, ricinoleic, 12-hydroxystearic, myristic, and linoleic acids,-of dodecane, tetradecane, octadecane, and 3:10-diethyltridecanesulphonic acids, of p-dodecylphenolsulphonic acid, and of oleo-p-anisidinesulphonic acid ; dodecyl-, tetradecyl-, octadecyl-, oleyl-, and diethylcyclohexylaminedodecylsulphate ; and the reaction products of long chain carboxylic acids with taurine or isethionic acid, e.g. C-(n-hexadecyl)-α-betaine, C-(n-dodecyl)-α- betaine, and the salts of the corresponding open chain betaine compounds. Turkey Red Oil may also be used. In example (1), a photographic developing solution is prepared by adding phenylhydrazine to an aqueous solution of sodium oleate and then adding a small quantity of an alkali metal acetate. In example (2), the acetate is replaced by sodium phosphate. In example (3), α-naphthylhydrazine is used, and a small quantity of sodium carbonate is added. In example (4), p-nitrophenylhydrazine hydrochloride is dissolved in boiling water, a hot 2 per cent aqueous sodium oleate solution is added, followed by a sodium carbonate solution. Finally the solution is diluted with a dilute sodium carbonate solution. Specification 545,443 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US299762A US2220929A (en) | 1939-10-16 | 1939-10-16 | Photographic developing solutions containing aromatic hydrazines, their preparation and use |
Publications (1)
Publication Number | Publication Date |
---|---|
GB545444A true GB545444A (en) | 1942-05-27 |
Family
ID=23156183
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15343/40A Expired GB545444A (en) | 1939-10-16 | 1940-10-16 | Improvements in or relating to primary aromatic hydrazine solutions and to the use of such solutions in photographic processes |
Country Status (2)
Country | Link |
---|---|
US (1) | US2220929A (en) |
GB (1) | GB545444A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2419974A (en) * | 1943-08-26 | 1947-05-06 | Eastman Kodak Co | Silver halide emulsions containing water-insoluble hydrazine derivatives |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2419975A (en) * | 1943-08-26 | 1947-05-06 | Eastman Kodak Co | Increasing speed and contrast of photographic emulsions |
US2544772A (en) * | 1947-06-04 | 1951-03-13 | Olin Ind Inc | Aqueous emulsions containing hydrazine derivatives as emulsifying agents |
US2892715A (en) * | 1954-07-01 | 1959-06-30 | Antioch College Of Yellow Spri | Antifoggant for photographic developers and solubilizing agent for hydrazines |
US3157502A (en) * | 1958-10-11 | 1964-11-17 | Philips Corp | Stabilized physical developers containing ionogenic surfactants |
-
1939
- 1939-10-16 US US299762A patent/US2220929A/en not_active Expired - Lifetime
-
1940
- 1940-10-16 GB GB15343/40A patent/GB545444A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2419974A (en) * | 1943-08-26 | 1947-05-06 | Eastman Kodak Co | Silver halide emulsions containing water-insoluble hydrazine derivatives |
Also Published As
Publication number | Publication date |
---|---|
US2220929A (en) | 1940-11-12 |
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