US3330663A - Silver salts of sulfur-containing aliphatic carboxylic acids as lightsensitive compounds - Google Patents
Silver salts of sulfur-containing aliphatic carboxylic acids as lightsensitive compounds Download PDFInfo
- Publication number
- US3330663A US3330663A US472308A US47230865A US3330663A US 3330663 A US3330663 A US 3330663A US 472308 A US472308 A US 472308A US 47230865 A US47230865 A US 47230865A US 3330663 A US3330663 A US 3330663A
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- US
- United States
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- beilstein
- solution
- vol
- 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
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- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 title description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 4
- 239000011593 sulfur Substances 0.000 title description 4
- 229910052717 sulfur Inorganic materials 0.000 title description 4
- 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 claims description 22
- 239000000839 emulsion Substances 0.000 claims description 19
- -1 MERCAPTO GROUP Chemical group 0.000 claims description 15
- 239000000243 solution Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 150000003378 silver Chemical class 0.000 description 9
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- 229910001961 silver nitrate Inorganic materials 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- 235000010443 alginic acid Nutrition 0.000 description 6
- 229920000615 alginic acid Polymers 0.000 description 6
- 150000004781 alginic acids Chemical class 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000783 alginic acid Substances 0.000 description 5
- 229960001126 alginic acid Drugs 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- 150000007949 saponins Chemical class 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 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
- 239000002904 solvent Substances 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- NCNYEGJDGNOYJX-NSCUHMNNSA-N (e)-2,3-dibromo-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Br)=C(/Br)C=O NCNYEGJDGNOYJX-NSCUHMNNSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JPHVSDWIWBDHOC-UHFFFAOYSA-N 2-(carboxymethylsulfanyl)butanedioic acid Chemical compound OC(=O)CSC(C(O)=O)CC(O)=O JPHVSDWIWBDHOC-UHFFFAOYSA-N 0.000 description 1
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 1
- 241000857945 Anita Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- 238000001016 Ostwald ripening Methods 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- PKDBSOOYVOEUQR-UHFFFAOYSA-N mucobromic acid Natural products OC1OC(=O)C(Br)=C1Br PKDBSOOYVOEUQR-UHFFFAOYSA-N 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005542 phthalazyl group Chemical group 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- OGFYIDCVDSATDC-UHFFFAOYSA-N silver silver Chemical class [Ag].[Ag] OGFYIDCVDSATDC-UHFFFAOYSA-N 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
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- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
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- 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
Definitions
- This invention relates to a light-sensitive photographic material which contains silver salts of sulfur-containing aliphatic carboxylic acids as light-sensitive compounds.
- Silver halides are used as light-sensitive compounds in conventional photographic materials.
- Organic silver salts, for example mercaptides, have also been proposed for this purpose, but have not been used in practice because they are not sufficiently light-sensitive or suffer from other disadvantages.
- photographic elements which contain silver salts of sulfur-containing aliphatic carboxylic acids as light-sensitive compounds.
- alkyl preferably with up to 18 carbon atoms, such as benzyl or phenylethyl, aryl such as phenyl or naphthyl, or heterocyclic rings such as diazolyl, oxazolyl, triazolyl, oxidiazolyl, thiadiazolyl, azaindenyl, preferably tetraor pentaazaindenyl, benzthiazo'lyl, naphthiothiazolyl, benzooxazolyl, naphthoxazolyl, pyridyl, quino-linyl, pyrimidyl, quinoxalinyl, quinazolinyl, which radicals may in turn be substituted, for example, by alkyl, preferably with up to 18 carbon atoms, aryl such as phenyl or naphthyl, hydroxyl, alkoxy with preferably up to 12 carbon atoms, aroxy such as phenoxy, acyl preferably
- alkyl groups of which having up to 5 carbon atoms acylamino with preferably acyl groups being derived from aliphatic carboxylic acids having up to 18 carbon atoms or aryl-substituted amino preferably a phenylamino, mercapto groups, mercapto groups substituted with alkyl having up to 18 carbon atoms, a phenyl, a naphthyl or a heterocyclic radical, halogen such as chlorine or bromine, sulfo groups or carboxyl groups and the like, and
- Sulfur-containing aliphatic carboxylic acids useful accord- R'(S) XCOOAg ing to the invention include the following: 1 184 C:
- the compounds can be isolated in the form of free acids or as alkali metal salts.
- the compounds can be purified by recrystallisation from or by solution and reprecipitation from water or alcohol. This is more fully described in the following examples:
- the solution is heated for 15 minutes on a steam bath while stirring.
- 50 g. of soda are then added in portions at about 60 C., after which the solution is heated for 3 hours on a steam bath and after cooling the product is precipitated by acidification with 50% aqueous acetic acid.
- the crude product is purified by washing with water.
- the resulting 65 g. of crude product are dissolved in an equivalent quantity of 5% aqueous soda solution, after which the sodium salt of the product is isolated in the form of fine needles by concentration.
- the salt melts at 218 C. after washing with acetone and drying in vacuo.
- Compounds 129-135 are prepared by reacting a Scange base with a mercapto-substituted aliphatic carboxylic acid as described for example by Stacy et al., J.A.C.S. 77, 3869, 1955.
- the preparation of conventional silver halide emulsion involves three separate steps: (1) precipitation of the silver halide in the presence of a protective colloid preferably gelatin and physical or Ostwald ripening, (2) flocculation and freeing of the emulsion of excess water-soluble salts, and (3) the chemical or after-ripening to obtain increased speed and sensitivity (compare Mees The Theory of the Photographic Process).
- novel photographic emulsions of the present invention can be prepared in analogous manner.
- the silver salts are prepared from equimolar quantities of the thioaliphatic carboxylic acid and the soluble salt such as silver nitrate.
- the reaction takes place in an aqueous solution of the reaction components, preferably in the presence of a protective colloid such as gelatin, polyvinyl alcohol, or sodium alginate.
- a protective colloid such as gelatin, polyvinyl alcohol, or sodium alginate.
- the components are forming binding agent reacted in a molar ratio about 1:1. That molar ratio relates to the number of carboxyl groups.
- an acid Which contains two carboxyl groups is preferably reacted with 2 mols of water-soluble silver salt such as silver nitrate.
- Acids which contain 3 or more oarboxyl groups are preferably reacted with a least 2 mols of silver salt.
- the most effective and suitable molar ratio will be apparent to those skilled in the art upon making the ordinary tests and observations customarily used in the :art of emulsion making. It has been found that an excess of water soluble silver salt produces fogging in the photographic emulsion. On the other hand, an excess of thioaliphatic carboxylic acid up to about 10 mol percent reduce the fog level without affecting sensitivity. A higher excess of the thioaliphatic carboxylic acid is not desirable since the lightsensitivity of the silver salts of the said acid is considerably reduced.
- Water soluble organic as silver complexes may thioaliphatic carboxylic salts used to prepare the vention may itself for example, as a quired pH-value.
- the silver salts according to the invention may also be employed in admixture with one another or with conventional silver halides.
- silver silver salts as well be used for the reaction with the acid.
- si-ons can also be sensitized with by R. Koslowsky, Z. wiss. photo.
- the emulsion can also be optically sensitized with the
- the emulsions may be hardened by any suitable hardener, such as formaldehyde, halogen substituted aliphatic acids such as mucobromic acid.
- Example I 30 ml. of a 40% aqueous citric acid solution and 20 g. of diethyldisulfide-1,2,1',2-tetracarboxylic acid (comequimolar quantity of aqueous sodium hydroxide solution, are added to 1 litre of an 8% C. ml. of a 10% C. After the addition of a wetting agent, for example 5 ml.
- the material may be developed, fixed and treated with water in the usual way.
- the following developer mixture is used:
- Example 2 30 ml. of a 40% aqueous solution of citric acid are added to 1 litre of an 8% aqueous gelatin solution, and the solution is heated to 45 C. 20 g. of carboxymethylmercaptosuccinic acid (compound 18) dissolved in an equimolar quantity of aqueous sodium hydroxide solution are added, after which precipitation is carried out while stirring vigorously with 100 ml. of a 10% aqueous silver nitrate solution. Before coating, 3 ml. of a 1% alcoholic solution of 1-phenyl-S-mercaptotetrazole, 5 ml. of a 1% alcoholic solution of benzotriazole, 1 ml. of a 30% aqueous formaldehyde solution and 5 ml. of 30% aqueous solution of saponin are added. The emulsion is applied in known manner on to a sheet of paper and is then dried.
- carboxymethylmercaptosuccinic acid compound 18
- this material may be employed as lightsensitive photographic material in the silver salt diffusion process without applying a silver salt solvent such as sodium thiosulfate.
- the exposed element is developeld in the usual way using thiosulfate-free transfer materials, containing development nuclei and thiosulfate-free aqueous developers.
- the materials are processed in accordance with common practice. After the materials have been separated, an excellent copy of the original is obtained in the transfer material.
- Example 3 2 ml. of a 40% aqueous solution of citric acid are added to 1 litre of an 8% aqueous gelatin solution, and the solution is heated to 40 C. 22 g. of s-[2-n-octylthio- 1,3,4-thiadiazolyl-(5)]thioglycollic acid (compound 96), dissolved in an equimolar quantity of an aqueous sodium hydroxide solution, are then added, after which precipitation is carried out while stirring vigorously with 100 ml. of a 10% aqueous solution of silver nitrate. Before coating, 125 g. of crystalline sodium acetate, 5 g. of potassium metabisulfate, 5 g.
- Example 4 30 ml. of a 40% aqueous solution of citric acid and 18 g. of compound 126 dissolved in water which, if desired,
- aqueous sodium hydroxide solution can be mixed with a small amount of aqueous sodium hydroxide solution to facilitate solution, are added at 40 C. to 1 litre of an 8% by weight aqueous gelatin solution. ml. of a 10% aqueous solution of silver nitrate are then added with vigorous stirring and digested for a few minutes at 40 C. After the addition of a wetting agent, for example 5 ml. of 30% by weight aqueous solution of saponin, and a hardening agent, for example 1 ml. of a 30% by weight formaldehyde solution, the emulsion is applied in known manner into a sheet of paper or into a transparent support for example of polyethylene terephthalate and dried.
- a wetting agent for example 5 ml. of 30% by weight aqueous solution of saponin
- a hardening agent for example 1 ml. of a 30% by weight formaldehyde solution
- the sensitivity of the coated material is similar to that of conventional photographic silver chloride contact-copying papers. After exposure, the material may be developed, fixed and treated with water in the usual way.
- the developer composition referred to an Example 1 can be used. Since the silver salt is precipitated in a very fine-grain form, these emulsions can be prepared which have a low silver content as compared with a conventional silver halide emulsion without affecting the density of the final images.
- compound 126 it is also possible to employ the following compounds in the quantities indicated: 14 g. of compound 111; 13 g. of compound 121; 21 g. of compound 16 g. of compound 124 or 16 g. of compound 119.
- Example 5 30 ml. of a 40% aqueous solution of citric acid are added to 1 litre of an 8% by weight aqueous gelatin solution, and the solution is heated to 45 C. 15 g. of compound 109 dissolved in water mixed with a little aqueous sodium hydroxide solution are then added, after which precipitation is carried out while stirring vigorously with 100 ml. of a 10% by weight aqueous solution of silver nitrate. Before casting, 3 ml. of a 1% by weight alcoholic solution of 1-phenyl-5-mercaptotetrazole, 5 ml. of a 1% by weight alcoholic solution of benztriazole, 1 ml. of a 30% by weight formaldehyde solution and 5 ml. of a 30% aqueous solution of saponin are added. The emulsion is applied to a sheet of paper in known manner and dried.
- the material is exposed and further processed in accordance with the silver salt diffusion process by developing the exposed light-sensitive layer, while in contact with a transfer sheet containing development nuclei and separating the sheets when the transfer of the silver salt is completed. Since the silver salt dissolves readily in an alkaline sulfite solution, it is not necessary to apply a silver salt solvent such as sodium thiosulfate in the developer bath or in the transfer sheet. An excellent copy of the original is obtained.
- Example 6 2 ml. of a 40% aqueous solution of citric acid are added to 1 litre of an 8% by weight aqueous gelatine solution, and the solution is heated to 40% C. 15 g. of compound 118 dissolved in water mixed with a small amount of sodium hydroxide solution are then added, after which precipitation is completed while stirring vigorously with 100 ml. of a 10% by weight aqueous silver nitrate solution. Before casting, 125 g. of crystalline sodium acetate, 5 g. of potassium metabisulfite, 5 g. of sodium 4-diethylaminobenzene-l-aminomethane sulfonate and 5 ml. of a 30% aqueous solution of saponin, are added. The solution is applied to a sheet of paper and dried.
- the material After exposure, the material can be developed under heat, or used as a light-sensitive material for a developer sublimation process as described for example in German patent specification No. 1,159,758.
- a light-sensitive photographic element having at 2.
- X represents an alkylene radical having up to 5 carbon atoms.
- R is a heterocyclic radical of the group consisting of a quinolyl, a pyrimidyl, a quinoxalyl, quinazolyl, phthalazyl, triazolyl and thiazolyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEA46854A DE1214083B (de) | 1964-08-14 | 1964-08-14 | Lichtempfindliches photographisches Material mit mindestens einer lichtempfindlichen Silbersalzemulsionsschicht |
DEA48186A DE1255484B (de) | 1964-08-14 | 1965-01-21 | Lichtempfindliches photographisches Material mit mindestens einer lichtempfindlichen Silbersalzemulsionsschicht |
Publications (1)
Publication Number | Publication Date |
---|---|
US3330663A true US3330663A (en) | 1967-07-11 |
Family
ID=25964088
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US472308A Expired - Lifetime US3330663A (en) | 1964-08-14 | 1965-07-15 | Silver salts of sulfur-containing aliphatic carboxylic acids as lightsensitive compounds |
Country Status (9)
Country | Link |
---|---|
US (1) | US3330663A (de) |
AT (1) | AT259366B (de) |
BE (1) | BE668340A (de) |
CH (1) | CH458056A (de) |
DE (2) | DE1214083B (de) |
DK (1) | DK113969B (de) |
GB (1) | GB1111492A (de) |
NL (1) | NL6510643A (de) |
SE (1) | SE310120B (de) |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3528810A (en) * | 1965-05-08 | 1970-09-15 | Agfa Gevaert Ag | Process for the production of direct positive images by the silver salt diffusion process |
US3532502A (en) * | 1967-09-14 | 1970-10-06 | Eastman Kodak Co | Silver salts of pyridine carboxylic acids and photographic emulsions containing the same |
US3647439A (en) * | 1968-10-01 | 1972-03-07 | Eastman Kodak Co | Photographic element, composition and process |
US3819382A (en) * | 1970-06-26 | 1974-06-25 | Agfa Gevaert Ag | Light-sensitive material having developers embedded therein |
US3960908A (en) * | 1973-01-22 | 1976-06-01 | Fuji Photo Film Co., Ltd. | Process for preparing organosilver carboxylates |
US4123274A (en) * | 1977-03-16 | 1978-10-31 | Eastman Kodak Company | Heat developable imaging materials and process |
US4451561A (en) * | 1982-04-28 | 1984-05-29 | Konishiroku Photo Industry Co., Ltd. | Heat-development-type image recording material |
US4543309A (en) * | 1982-05-07 | 1985-09-24 | Konishiroku Photo Industry Co., Ltd. | Heat-developable image-pattern recording material |
EP0200011A1 (de) | 1985-03-30 | 1986-11-05 | Fuji Photo Film Co., Ltd. | Wärmeentwickelbares lichtempfindliches Material |
US5238792A (en) * | 1992-04-20 | 1993-08-24 | Minnesota Mining And Manufacturing Company | Imageable articles having dye selective interlayers |
US5240809A (en) * | 1992-04-20 | 1993-08-31 | Minnesota Mining And Manufacturing Company | Imageable articles having dye selective interlayers |
US5262272A (en) * | 1992-10-08 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Dye permeable polymer interlayers |
US5264321A (en) * | 1992-07-16 | 1993-11-23 | Minnesota Mining And Manufacturing Company | Photothermographic elements with novel layer structures |
US5491059A (en) * | 1994-10-31 | 1996-02-13 | Minnesota Mining And Manufacturing Company | Silver carboxylate compounds as silver sources in photothermographic and thermographic elements |
US5492804A (en) * | 1994-06-30 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Chromogenic leuco redox-dye-releasing compounds for photothermographic elements |
US5492805A (en) * | 1994-06-30 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Blocked leuco dyes for photothermographic elements |
US5492803A (en) * | 1995-01-06 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Hydrazide redox-dye-releasing compounds for photothermographic elements |
US5891615A (en) * | 1997-04-08 | 1999-04-06 | Imation Corp. | Chemical sensitization of photothermographic silver halide emulsions |
US5928857A (en) * | 1994-11-16 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Photothermographic element with improved adherence between layers |
US5939249A (en) * | 1997-06-24 | 1999-08-17 | Imation Corp. | Photothermographic element with iridium and copper doped silver halide grains |
US6171707B1 (en) | 1994-01-18 | 2001-01-09 | 3M Innovative Properties Company | Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent |
US6472131B1 (en) | 2000-05-04 | 2002-10-29 | Eastman Kodak Company | Asymmetric silver salt dimers and imaging compositions, materials and methods using same |
US7468241B1 (en) | 2007-09-21 | 2008-12-23 | Carestream Health, Inc. | Processing latitude stabilizers for photothermographic materials |
EP2042871A1 (de) | 2007-09-28 | 2009-04-01 | Fujifilm Corporation | Verfahren zum Mischen zweier oder mehrerer Arten von Flüssigkeiten in einem porösen Träger |
US7524621B2 (en) | 2007-09-21 | 2009-04-28 | Carestream Health, Inc. | Method of preparing silver carboxylate soaps |
EP2065706A2 (de) | 2007-11-29 | 2009-06-03 | Fujifilm Corporation | Messkit und Immunochromatografieverfahren |
US7622247B2 (en) | 2008-01-14 | 2009-11-24 | Carestream Health, Inc. | Protective overcoats for thermally developable materials |
WO2015148028A1 (en) | 2014-03-24 | 2015-10-01 | Carestream Health, Inc. | Thermally developable imaging materials |
WO2016073086A1 (en) | 2014-11-04 | 2016-05-12 | Carestream Health, Inc. | Image forming materials, preparations, and compositions |
WO2016195950A1 (en) | 2015-06-02 | 2016-12-08 | Carestream Health, Inc. | Thermally developable imaging materials and methods |
WO2017123444A1 (en) | 2016-01-15 | 2017-07-20 | Carestream Health, Inc. | Method of preparing silver carboxylate soaps |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE787868A (fr) * | 1971-09-03 | 1973-02-23 | Agfa Gevaert Nv | Procede voor de vervaardiging van een voor vlekken ongevoelige fotografische zilverhalogenideemulsie |
DE2623942A1 (de) * | 1976-05-28 | 1977-12-08 | Agfa Gevaert Ag | Schmalfilmkassette |
US4275065A (en) * | 1979-06-21 | 1981-06-23 | American Home Products Corporation | Modulating the immune response with 2-substituted-3-hydroxythiazolo[2,3-b]be |
DE2950095A1 (de) * | 1979-12-13 | 1981-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Benzothiazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
HU193951B (en) * | 1985-03-11 | 1987-12-28 | Richter Gedeon Vegyeszet | Process for producing new sulfur-containing 5-substituted benzimidazol derivatives and pharmaceutical compositions containing them |
DE4331162A1 (de) * | 1993-09-14 | 1995-03-16 | Bayer Ag | Verfahren zur Herstellung von Cyaninfarbstoffen |
EP0687572B1 (de) | 1994-06-15 | 1997-08-20 | Agfa-Gevaert N.V. | Wärmeempfindliches Aufzeichnungsverfahren |
DE69505605T2 (de) | 1994-07-13 | 1999-05-27 | Agfa-Gevaert N.V., Mortsel | Wärmeempfindliches Aufzeichnungsmaterial |
DE69514648T2 (de) | 1995-06-27 | 2000-07-13 | Agfa-Gevaert N.V., Mortsel | Verfahren zur Herstellung eines Bildes nach dem Wärmeverfahren |
EP0779539B1 (de) | 1995-11-27 | 2002-07-17 | Agfa-Gevaert | Thermographisches Material mit einer organischen antistatischen Aussenschicht |
EP0775595B1 (de) | 1995-11-27 | 1999-09-15 | Agfa-Gevaert N.V. | Wärmeempfindliches Auszeignungsmaterial, das Phosphorsäurederivaten als Schmiermitteln enthält |
EP0775592B1 (de) | 1995-11-27 | 2002-09-11 | Agfa-Gevaert | Wärmeempfindliches Bildaufzeichnungsverfahren |
EP0782043B1 (de) | 1995-12-27 | 2003-01-15 | Agfa-Gevaert | Wärmeempfindliches Aufzeichnungsmaterial mit verbesserter Tonwiedergabe |
EP0845709B1 (de) | 1996-11-29 | 2006-01-18 | Agfa-Gevaert | Wärmeempfindliches Aufzeichnungselement und Verfahren zur Herstellung einer lithographischen Druckform damit |
-
1964
- 1964-08-14 DE DEA46854A patent/DE1214083B/de active Pending
-
1965
- 1965-01-21 DE DEA48186A patent/DE1255484B/de active Pending
- 1965-07-15 US US472308A patent/US3330663A/en not_active Expired - Lifetime
- 1965-07-22 CH CH1028065A patent/CH458056A/de unknown
- 1965-08-13 GB GB34819/65A patent/GB1111492A/en not_active Expired
- 1965-08-13 DK DK416665AA patent/DK113969B/da unknown
- 1965-08-13 SE SE10616/65A patent/SE310120B/xx unknown
- 1965-08-13 NL NL6510643A patent/NL6510643A/xx unknown
- 1965-08-16 AT AT752065A patent/AT259366B/de active
- 1965-08-17 BE BE668340D patent/BE668340A/xx unknown
Non-Patent Citations (1)
Title |
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None * |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3528810A (en) * | 1965-05-08 | 1970-09-15 | Agfa Gevaert Ag | Process for the production of direct positive images by the silver salt diffusion process |
US3532502A (en) * | 1967-09-14 | 1970-10-06 | Eastman Kodak Co | Silver salts of pyridine carboxylic acids and photographic emulsions containing the same |
US3647439A (en) * | 1968-10-01 | 1972-03-07 | Eastman Kodak Co | Photographic element, composition and process |
US3819382A (en) * | 1970-06-26 | 1974-06-25 | Agfa Gevaert Ag | Light-sensitive material having developers embedded therein |
US3960908A (en) * | 1973-01-22 | 1976-06-01 | Fuji Photo Film Co., Ltd. | Process for preparing organosilver carboxylates |
US4123274A (en) * | 1977-03-16 | 1978-10-31 | Eastman Kodak Company | Heat developable imaging materials and process |
US4128557A (en) * | 1977-03-16 | 1978-12-05 | Eastman Kodak Company | Silver salts of 1,2,4-mercaptotriazole derivatives |
US4451561A (en) * | 1982-04-28 | 1984-05-29 | Konishiroku Photo Industry Co., Ltd. | Heat-development-type image recording material |
US4543309A (en) * | 1982-05-07 | 1985-09-24 | Konishiroku Photo Industry Co., Ltd. | Heat-developable image-pattern recording material |
EP0200011A1 (de) | 1985-03-30 | 1986-11-05 | Fuji Photo Film Co., Ltd. | Wärmeentwickelbares lichtempfindliches Material |
US5238792A (en) * | 1992-04-20 | 1993-08-24 | Minnesota Mining And Manufacturing Company | Imageable articles having dye selective interlayers |
US5240809A (en) * | 1992-04-20 | 1993-08-31 | Minnesota Mining And Manufacturing Company | Imageable articles having dye selective interlayers |
US5264321A (en) * | 1992-07-16 | 1993-11-23 | Minnesota Mining And Manufacturing Company | Photothermographic elements with novel layer structures |
US5364733A (en) * | 1992-07-16 | 1994-11-15 | Minnesota Mining And Manufacturing Company | Photothermographic elements with novel layer structures, each of which contains a thermally-diffusible oxidizable leuco dye and process for producing a color image from leuco dye |
US5262272A (en) * | 1992-10-08 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Dye permeable polymer interlayers |
US6171707B1 (en) | 1994-01-18 | 2001-01-09 | 3M Innovative Properties Company | Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent |
US5492804A (en) * | 1994-06-30 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Chromogenic leuco redox-dye-releasing compounds for photothermographic elements |
US5492805A (en) * | 1994-06-30 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Blocked leuco dyes for photothermographic elements |
US5705676A (en) * | 1994-06-30 | 1998-01-06 | Minnesota Mining And Manufacturing Company | Chromogenic leuco redox-dye-releasing compounds for photothermographic elements |
US5696289A (en) * | 1994-06-30 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Blocked leuco dyes for photothermographic elements |
EP0710877A3 (de) * | 1994-10-31 | 1996-10-30 | Minnesota Mining & Mfg | Neue Silbercarboxylatverbindungen als Silberquellen in photothermographischen und thermographischen Elementen |
US5491059A (en) * | 1994-10-31 | 1996-02-13 | Minnesota Mining And Manufacturing Company | Silver carboxylate compounds as silver sources in photothermographic and thermographic elements |
EP0710877A2 (de) * | 1994-10-31 | 1996-05-08 | Minnesota Mining And Manufacturing Company | Neue Silbercarboxylatverbindungen als Silberquellen in photothermographischen und thermographischen Elementen |
US5928857A (en) * | 1994-11-16 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Photothermographic element with improved adherence between layers |
US5492803A (en) * | 1995-01-06 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Hydrazide redox-dye-releasing compounds for photothermographic elements |
US5891615A (en) * | 1997-04-08 | 1999-04-06 | Imation Corp. | Chemical sensitization of photothermographic silver halide emulsions |
US5939249A (en) * | 1997-06-24 | 1999-08-17 | Imation Corp. | Photothermographic element with iridium and copper doped silver halide grains |
US6060231A (en) * | 1997-06-24 | 2000-05-09 | Eastman Kodak Company | Photothermographic element with iridium and copper doped silver halide grains |
US6472131B1 (en) | 2000-05-04 | 2002-10-29 | Eastman Kodak Company | Asymmetric silver salt dimers and imaging compositions, materials and methods using same |
US6566045B1 (en) | 2000-05-04 | 2003-05-20 | Eastman Kodak Company | Asymmetric silver salt dimers and imaging compositions, materials and methods using same |
US7524621B2 (en) | 2007-09-21 | 2009-04-28 | Carestream Health, Inc. | Method of preparing silver carboxylate soaps |
US7468241B1 (en) | 2007-09-21 | 2008-12-23 | Carestream Health, Inc. | Processing latitude stabilizers for photothermographic materials |
EP2042871A1 (de) | 2007-09-28 | 2009-04-01 | Fujifilm Corporation | Verfahren zum Mischen zweier oder mehrerer Arten von Flüssigkeiten in einem porösen Träger |
EP2065706A2 (de) | 2007-11-29 | 2009-06-03 | Fujifilm Corporation | Messkit und Immunochromatografieverfahren |
US7622247B2 (en) | 2008-01-14 | 2009-11-24 | Carestream Health, Inc. | Protective overcoats for thermally developable materials |
WO2015148028A1 (en) | 2014-03-24 | 2015-10-01 | Carestream Health, Inc. | Thermally developable imaging materials |
US9335623B2 (en) | 2014-03-24 | 2016-05-10 | Carestream Health, Inc. | Thermally developable imaging materials |
WO2016073086A1 (en) | 2014-11-04 | 2016-05-12 | Carestream Health, Inc. | Image forming materials, preparations, and compositions |
US9523915B2 (en) | 2014-11-04 | 2016-12-20 | Carestream Health, Inc. | Image forming materials, preparations, and compositions |
WO2016195950A1 (en) | 2015-06-02 | 2016-12-08 | Carestream Health, Inc. | Thermally developable imaging materials and methods |
US9746770B2 (en) | 2015-06-02 | 2017-08-29 | Carestream Health, Inc. | Thermally developable imaging materials and methods |
WO2017123444A1 (en) | 2016-01-15 | 2017-07-20 | Carestream Health, Inc. | Method of preparing silver carboxylate soaps |
Also Published As
Publication number | Publication date |
---|---|
CH458056A (de) | 1968-06-15 |
NL6510643A (de) | 1966-02-15 |
DE1255484B (de) | 1967-11-30 |
BE668340A (de) | 1966-02-17 |
DE1214083B (de) | 1966-04-07 |
SE310120B (de) | 1969-04-14 |
AT259366B (de) | 1968-01-10 |
GB1111492A (en) | 1968-04-24 |
DK113969B (da) | 1969-05-12 |
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