US3525622A - Light-sensitive silver halide emulsions - Google Patents
Light-sensitive silver halide emulsions Download PDFInfo
- Publication number
- US3525622A US3525622A US623207A US3525622DA US3525622A US 3525622 A US3525622 A US 3525622A US 623207 A US623207 A US 623207A US 3525622D A US3525622D A US 3525622DA US 3525622 A US3525622 A US 3525622A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- emulsion
- series
- ethyl
- silver
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 silver halide Chemical class 0.000 title description 45
- 239000000839 emulsion Substances 0.000 title description 41
- 229910052709 silver Inorganic materials 0.000 title description 26
- 239000004332 silver Substances 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 description 16
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 229910021607 Silver chloride Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 230000001235 sensitizing effect Effects 0.000 description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- ZEUDGVUWMXAXEF-UHFFFAOYSA-L bromo(chloro)silver Chemical compound Cl[Ag]Br ZEUDGVUWMXAXEF-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 150000004867 thiadiazoles Chemical class 0.000 description 3
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 2
- IAYYOJKXEURELC-UHFFFAOYSA-N 4-benzylsulfanylthiadiazole Chemical compound C(C1=CC=CC=C1)SC=1N=NSC=1 IAYYOJKXEURELC-UHFFFAOYSA-N 0.000 description 2
- UMTVJJXGYYZKAV-UHFFFAOYSA-N 4-ethylsulfanylthiadiazole Chemical compound CCSC1=CSN=N1 UMTVJJXGYYZKAV-UHFFFAOYSA-N 0.000 description 2
- AWPNFXRMNNPKDW-UHFFFAOYSA-N 4-phenylthiadiazole Chemical compound S1N=NC(C=2C=CC=CC=2)=C1 AWPNFXRMNNPKDW-UHFFFAOYSA-N 0.000 description 2
- KDYVCOSVYOSHOL-UHFFFAOYSA-N 7-methylquinoline Chemical compound C1=CC=NC2=CC(C)=CC=C21 KDYVCOSVYOSHOL-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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical class C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- UUJOCRCAIOAPFK-UHFFFAOYSA-N 1,3-benzoselenazol-5-ol Chemical compound OC1=CC=C2[se]C=NC2=C1 UUJOCRCAIOAPFK-UHFFFAOYSA-N 0.000 description 1
- ORIIXCOYEOIFSN-UHFFFAOYSA-N 1,3-benzothiazol-6-ol Chemical compound OC1=CC=C2N=CSC2=C1 ORIIXCOYEOIFSN-UHFFFAOYSA-N 0.000 description 1
- SAHAKBXWZLDNAA-UHFFFAOYSA-N 1,3-benzoxazol-6-ol Chemical compound OC1=CC=C2N=COC2=C1 SAHAKBXWZLDNAA-UHFFFAOYSA-N 0.000 description 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical class C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 1
- UHXUPSPGFPYATJ-UHFFFAOYSA-N 1-ethylbenzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2N(CC)C=NC2=C1 UHXUPSPGFPYATJ-UHFFFAOYSA-N 0.000 description 1
- UHUPEGPJJKTCML-UHFFFAOYSA-N 1-ethylbenzimidazole-5-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C2N(CC)C=NC2=C1 UHUPEGPJJKTCML-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ODPJQZNJZWLTJH-UHFFFAOYSA-N 2,3-dihydrotriazolo[4,5-d]pyrimidin-5-one Chemical class O=C1N=CC2=NNNC2=N1 ODPJQZNJZWLTJH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 1
- NMIDXKUVKWNWQY-UHFFFAOYSA-N 3-ethylbenzimidazole-4-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2N(CC)C=NC2=C1 NMIDXKUVKWNWQY-UHFFFAOYSA-N 0.000 description 1
- OZOATVDNYIWEEY-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzoselenazole Chemical compound C1CCCC2=C1N=C[se]2 OZOATVDNYIWEEY-UHFFFAOYSA-N 0.000 description 1
- RMFVVPBBEDMZQI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole Chemical compound C1CCCC2=C1N=CS2 RMFVVPBBEDMZQI-UHFFFAOYSA-N 0.000 description 1
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 1
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical compound O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 description 1
- BGTVICKPWACXLR-UHFFFAOYSA-N 4,5-diphenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BGTVICKPWACXLR-UHFFFAOYSA-N 0.000 description 1
- NDUHYERSZLRFNL-UHFFFAOYSA-N 4,6-dimethyl-1,3-benzoxazole Chemical compound CC1=CC(C)=C2N=COC2=C1 NDUHYERSZLRFNL-UHFFFAOYSA-N 0.000 description 1
- NDKYVRQAANNPQD-UHFFFAOYSA-N 4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=CSC=2)=C1 NDKYVRQAANNPQD-UHFFFAOYSA-N 0.000 description 1
- SZHUYYAEKCCJAR-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC=N1 SZHUYYAEKCCJAR-UHFFFAOYSA-N 0.000 description 1
- GQPBBURQQRLAKF-UHFFFAOYSA-N 4-ethyl-1,3-oxazole Chemical compound CCC1=COC=N1 GQPBBURQQRLAKF-UHFFFAOYSA-N 0.000 description 1
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-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
- NTFMLYSGIKHECT-UHFFFAOYSA-N 4-phenyl-1,3-oxazole Chemical compound O1C=NC(C=2C=CC=CC=2)=C1 NTFMLYSGIKHECT-UHFFFAOYSA-N 0.000 description 1
- GYVLFYQMEWXHQF-UHFFFAOYSA-N 5,6-dichloro-1-ethylbenzimidazole Chemical compound ClC1=C(Cl)C=C2N(CC)C=NC2=C1 GYVLFYQMEWXHQF-UHFFFAOYSA-N 0.000 description 1
- HYXKRZZFKJHDRT-UHFFFAOYSA-N 5,6-dimethoxy-1,3-benzothiazole Chemical compound C1=C(OC)C(OC)=CC2=C1SC=N2 HYXKRZZFKJHDRT-UHFFFAOYSA-N 0.000 description 1
- QMUXKZBRYRPIPQ-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzothiazole Chemical compound C1=C(C)C(C)=CC2=C1SC=N2 QMUXKZBRYRPIPQ-UHFFFAOYSA-N 0.000 description 1
- RWNMLYACWNIEIG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzoxazole Chemical compound C1=C(C)C(C)=CC2=C1OC=N2 RWNMLYACWNIEIG-UHFFFAOYSA-N 0.000 description 1
- AHIHYPVDBXEDMN-UHFFFAOYSA-N 5-methoxy-1,3-benzoselenazole Chemical compound COC1=CC=C2[se]C=NC2=C1 AHIHYPVDBXEDMN-UHFFFAOYSA-N 0.000 description 1
- NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 description 1
- GKJSZXGYFJBYRQ-UHFFFAOYSA-N 6-chloroquinoline Chemical compound N1=CC=CC2=CC(Cl)=CC=C21 GKJSZXGYFJBYRQ-UHFFFAOYSA-N 0.000 description 1
- AJAKVPMSAABZRX-UHFFFAOYSA-N 6-ethoxyquinoline Chemical compound N1=CC=CC2=CC(OCC)=CC=C21 AJAKVPMSAABZRX-UHFFFAOYSA-N 0.000 description 1
- FKYKJYSYSGEDCG-UHFFFAOYSA-N 6-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2N=COC2=C1 FKYKJYSYSGEDCG-UHFFFAOYSA-N 0.000 description 1
- HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 description 1
- SZWNDAUMBWLYOQ-UHFFFAOYSA-N 6-methylbenzoxazole Chemical compound CC1=CC=C2N=COC2=C1 SZWNDAUMBWLYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- RUSMDMDNFUYZTM-UHFFFAOYSA-N 8-chloroquinoline Chemical compound C1=CN=C2C(Cl)=CC=CC2=C1 RUSMDMDNFUYZTM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JYHZYGLHIATDLE-UHFFFAOYSA-N CCOC([S+]1C(C)=NC=C1)=O Chemical group CCOC([S+]1C(C)=NC=C1)=O JYHZYGLHIATDLE-UHFFFAOYSA-N 0.000 description 1
- WLHBRQYVZLNQFE-UHFFFAOYSA-N O[S+]1C2=CC=CC=C2N=C1 Chemical compound O[S+]1C2=CC=CC=C2N=C1 WLHBRQYVZLNQFE-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical class C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical class C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- IEICFDLIJMHYQB-UHFFFAOYSA-N benzo[g][1,3]benzoselenazole Chemical compound C1=CC=CC2=C([se]C=N3)C3=CC=C21 IEICFDLIJMHYQB-UHFFFAOYSA-N 0.000 description 1
- IIUUNAJWKSTFPF-UHFFFAOYSA-N benzo[g][1,3]benzothiazole Chemical compound C1=CC=CC2=C(SC=N3)C3=CC=C21 IIUUNAJWKSTFPF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
- 150000001661 cadmium Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HMWONSCWEVYKNG-UHFFFAOYSA-N ethyl 3-ethylbenzimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1N(CC)C=N2 HMWONSCWEVYKNG-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B26/00—Hydrazone dyes; Triazene dyes
- C09B26/02—Hydrazone dyes
-
- 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- This invention relates to light-sensitive silver halide emulsions.
- Light-sensitive silver halide emulsions are in general characterized by their sensitivity, gradation and fog.
- sensitivity, gradation and fog can be regulated by the way of preparing the silver halide and the use of special chemical ingredients effecting a desired improvement or result.
- Addenda to the emulsion which are of particular importance for the stability of the lightsensitive characteristics of a silver halide emulsion are the so-called stabilizers.
- Stabilizers or antifoggants protect the light-sensitive silver halide emulsions against spontaneous growth of fog during prolonged storage or storage at high temperatures and humidities or during development to maximum contrast and speed.
- photographic silver halide emulsions can be stabilized against the formation of spontaneous fog by incorporating in the emulsions certain silver complexing agents, more particularly heterocyclic hydrazone compounds which can be represented by the following general formula (I):
- benzoxazole S-chlorobenzoxazole, S-methylbenzoxazole, 5-phenylbenzoxazole, 6-methylbenzoxazole, 5,6-dimethylbenzoxazole, 4,6- dimethylbenzoxazole, S-methoxybenzoxazole, 6-methoxybenzoxazole, S-hydroxybenzoxazole, 6-hydroxybenzoxazole), those of the naphthoxazole series (e.g. naphtho [2, l-d] oxazole, naphtho 1,2-d] oxazole) those of the selenazole series (e.g.
- 4-methylselenazo1e, 4-phenylsele'nazole those of the benzoselenazole series (e.g. benzoselenazole, S-chlorobenzoselenazole, 5-methoxybenzoselenazole, 5-hydroxybenzoselenazole, 4,5,6,7-tetrahydrobenzoselenazole), those of the naphthoselenazole series (e.g. naphtho [2,1-d] selenazole, naphtho[1,2-d]selenazole), those of the Z-quinoline series (e.g.
- benzimidazole series e.gL l-ethylbenzimidazole, l-phenylbenzimidazole, 1-ethyl-5,6-dichlorobenzimidazole, 1-hydroxy-ethyl-5,6-dichlorobenzimidazo1e, 1-ethyl-S-chlorobenzimidazole, l-ethyl-5,6-dibromobenzimidazole, 1-ethyl-5-chloro-6-amino-benzirnidazole, 1-ethy1-5-chloro-6-bromobenzimidazole, 1-ethyl-S-phenylbenzimidazole, l-ethyl-S-fluorobenzimidazole, 1-ethyl-5,6-difiuorobenzimidazole, 1-ethyl-5-cyanobenzimidazole, 1-
- Z' represents the necessary atoms to close a heterocyclic ring containing as heteroatoms one or more nitrogen atoms e.g. a 2H-pyrrole, imidazole, benzimidazole, l-H-indazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, s-triazine, isoquinoline, quinoline, phthalazine, quinoxaline, quinazoline, cinnoline, phenanthridine or condensed ring systems containing said nuclei e.g. B-purine, pteridine, fi-carboline and phenanthroline.
- nitrogen atoms e.g. a 2H-pyrrole, imidazole, benzimidazole, l-H-indazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, s-triazine, isoquinoline
- HaC N 02 mCUChMHj CH NNH-W [000mm OJhN-NH-).
- Z represents the necessary atoms to close a heterocyclic nucleus of the thiazole series (e.g. thiazole, 4- (p-t01yl)- thiazole, 4,5-diphenylthiazole, 4-m-nitrophenylthiazole, 4-p-bromophenylthiazole, 4 methyl-S-ethoxycarbonylthiazole, benzthiazole, carboxylic acid substituted benzthiazole and sulphonic acid substituted benzthiazole) and those of the thiadiazole series (e.g. 4-phenylthiadiazole, 4-ethylthiothiadiazole, 4 -benzylthiothiadiazole and 4-benzylsulphonylthiadiazole), and
- the addenda of the present invention can be added to photographic emulsions using any of the well-known techniques in emulsion preparation. For example, they can be added in dissolved state to the silver halide emulsion, or they can be added to the emulsion in the form of a dispersion similar to techniques used to incorporate colour couplers in the emulsion.
- the stabilizing agents are preferably added to the photographic emulsion after the final digestion or after-ripening, although they can advantageously be added prior to digestion.
- hydrazone compounds described above can 'be used in combination with other stabilizing agents e.g. of the hydroxy-triazolopyrimidine series (azaindolizines), cadmium salts, mercury compounds and with chemically sensitizing compounds, for instance sulphur compounds and noble metal salts e.g. gold salts.
- other stabilizing agents e.g. of the hydroxy-triazolopyrimidine series (azaindolizines), cadmium salts, mercury compounds and with chemically sensitizing compounds, for instance sulphur compounds and noble metal salts e.g. gold salts.
- addenda such as hardening agents, wetting agents, plasticizers, developing agents, and optical sensitizing agents can be incorporated into the emulsion in the usual way.
- the amount of hydrazone compounds employed in the silver halide emulsion depends on the particular type of the emulsion and the desired effect, usually said compounds are employed in a ratio of 0.05 millimole to 50 millimole per mole of silver halide.
- silver chlorlide and silver chloride-bromide emulsions wherein they show useful spectral sensitizing effects (a sensitizing maximum in the range of 420 nm to 520 nm) they are preferably used in an amount of 0.05 millimole to 10 millimole per mole silver halide.
- the stabilizing addenda of the invention can be used in various kinds of photographic emulsion, e.g. spectrally nonsensitized emulsions, spectrally sensitized emulsions, X-ray emulsions, and emulsions sensitive to infrared radiation.
- Various silver salts may be used as lightsensitive salt, e.g., silver bromide, silver iodide, silver chloride, or mixed silver halides, e.g., silver chlorobromide or silver bromo-iodide.
- They may be used in silver halide emulsions for application in the silver halide complex diffusion transfer process or other transfer processes based on silver halide photography, in which, e.g., tlie diifusion of a developer, a coupler, or a dye is appied.
- the stabilizing and anti-fogging action is determined by an incubation test of the emulsions as indicated in the following Table 2.
- the fog, gradation and sensitivity values are expressed as a relative increase or decrease in respect of a control emulsion (blank).
- the tested emulsion is a silver bromide-iodide (4.5 mole percent iodide) emulsion.
- the incubated emulsions are for 5 min. at 20 C. developed in a developing bath of the following composition:
- a photographic material comprising a silver halide emulsion layer containing a compound according to the following general formula:
- R is hydrogen or an alkyl radical
- Z represents the atoms necessary for completing a heterocyclic ring
- Z represents the atoms necessary for completing a heterocyclic ring, containing as hetero atoms only one or more nitrogen atoms.
- a photographic material according to claim 1 comprising a silver halide emulsion layer containing silver chloride or silver chloride-bromide, the speed of which has been increased by a compound according to the following general formula:
- a photographic material according to claim 1 comprising a silver halide emulsion layer containing a compound according to the following general formula:
- R is hydrogen or a methyl group
- Z represents the atoms necessary for completing a pyridine nucleus, a quinoline nucleus, a pyrimidine nucleus, a quinazoline nucleus, a phthalazine nucleus, a quinoxaline nucleus, a benzimidazole nucleus, a thiazole nucleus or a benzithiazole nucleus, and
- Z represents the atoms necessary to complete a pyridine nucleus or a quinoline nucleus.
- a photographic silver chloride or silver chloridebromide material according to claim 2 containing said compound in a ratio of 0.05 millimole to 10 millimole per mole silver halide.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11345/66A GB1118654A (en) | 1966-03-15 | 1966-03-15 | Improved light-sensitive silver halide emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3525622A true US3525622A (en) | 1970-08-25 |
Family
ID=9984567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US623207A Expired - Lifetime US3525622A (en) | 1966-03-15 | 1967-03-15 | Light-sensitive silver halide emulsions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3525622A (en:Method) |
| BE (1) | BE695443A (en:Method) |
| DE (1) | DE1522429A1 (en:Method) |
| FR (1) | FR1515642A (en:Method) |
| GB (1) | GB1118654A (en:Method) |
| NL (1) | NL6702919A (en:Method) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075019A (en) * | 1974-04-15 | 1978-02-21 | Eastman Kodak Company | High gain cobalt(III)complex composition and element |
| US4094683A (en) * | 1975-06-27 | 1978-06-13 | Fuji Photo Film Co., Ltd. | Direct positive silver halide photographic materials |
| US4243737A (en) * | 1977-11-25 | 1981-01-06 | Eastman Kodak Company | Image forming composition and elements with Co(III) complex, conjugated π bonding compounds and photoreductant |
| EP0147105A3 (en) * | 1983-12-20 | 1985-08-28 | Eastman Kodak Company | Photographic products employing novel nondiffusible hydrazone dye-releasing compounds |
| US20030166658A1 (en) * | 2000-06-05 | 2003-09-04 | Johann Hofmann | Heterocyclic hydrazones for use as anti-cancer agents |
| US20040056378A1 (en) * | 2002-09-25 | 2004-03-25 | Bredt James F. | Three dimensional printing material system and method |
| CZ303748B6 (cs) * | 2011-10-11 | 2013-04-17 | Vysoká skola chemicko - technologická v Praze | Ftalazin-1-ylhydrazony a jejich pouzití k lécbe nádorových onemocnení |
| US20170290830A1 (en) * | 2016-04-08 | 2017-10-12 | Baylor College Of Medicine | Small molecule regulators of steroid receptor coactivators and methods of use thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB447109A (en) * | 1934-08-03 | 1936-05-04 | John David Kendall | Improvements in or relating to the sensitisation of photographic emulsions |
| US2295008A (en) * | 1940-03-12 | 1942-09-08 | Eastman Kodak Co | Photographic color forming compound |
| GB636403A (en) * | 1946-07-16 | 1950-04-26 | Gen Aniline & Film Corp | Azamerocyanine dyes and a process for the preparation thereof |
| US2588538A (en) * | 1948-08-06 | 1952-03-11 | Ilford Ltd | Stabilizers in photographic emulsions and developers |
-
1966
- 1966-03-15 GB GB11345/66A patent/GB1118654A/en not_active Expired
-
1967
- 1967-02-24 NL NL6702919A patent/NL6702919A/xx unknown
- 1967-03-09 FR FR100351A patent/FR1515642A/fr not_active Expired
- 1967-03-10 DE DE19671522429 patent/DE1522429A1/de active Pending
- 1967-03-14 BE BE695443D patent/BE695443A/xx unknown
- 1967-03-15 US US623207A patent/US3525622A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB447109A (en) * | 1934-08-03 | 1936-05-04 | John David Kendall | Improvements in or relating to the sensitisation of photographic emulsions |
| US2295008A (en) * | 1940-03-12 | 1942-09-08 | Eastman Kodak Co | Photographic color forming compound |
| GB636403A (en) * | 1946-07-16 | 1950-04-26 | Gen Aniline & Film Corp | Azamerocyanine dyes and a process for the preparation thereof |
| US2588538A (en) * | 1948-08-06 | 1952-03-11 | Ilford Ltd | Stabilizers in photographic emulsions and developers |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075019A (en) * | 1974-04-15 | 1978-02-21 | Eastman Kodak Company | High gain cobalt(III)complex composition and element |
| US4094683A (en) * | 1975-06-27 | 1978-06-13 | Fuji Photo Film Co., Ltd. | Direct positive silver halide photographic materials |
| US4243737A (en) * | 1977-11-25 | 1981-01-06 | Eastman Kodak Company | Image forming composition and elements with Co(III) complex, conjugated π bonding compounds and photoreductant |
| EP0147105A3 (en) * | 1983-12-20 | 1985-08-28 | Eastman Kodak Company | Photographic products employing novel nondiffusible hydrazone dye-releasing compounds |
| US20030166658A1 (en) * | 2000-06-05 | 2003-09-04 | Johann Hofmann | Heterocyclic hydrazones for use as anti-cancer agents |
| US7112680B2 (en) * | 2000-06-05 | 2006-09-26 | Austria Wirtschaftsservice Gesellschaft Mit Beschrankter Haftung | Heterocyclic hydrazones for use as anti-cancer agents |
| US20040056378A1 (en) * | 2002-09-25 | 2004-03-25 | Bredt James F. | Three dimensional printing material system and method |
| CZ303748B6 (cs) * | 2011-10-11 | 2013-04-17 | Vysoká skola chemicko - technologická v Praze | Ftalazin-1-ylhydrazony a jejich pouzití k lécbe nádorových onemocnení |
| US20170290830A1 (en) * | 2016-04-08 | 2017-10-12 | Baylor College Of Medicine | Small molecule regulators of steroid receptor coactivators and methods of use thereof |
| US10265315B2 (en) * | 2016-04-08 | 2019-04-23 | Baylor College Of Medicine | Small molecule regulators of steroid receptor coactivators and methods of use thereof |
| US10512647B2 (en) | 2016-04-08 | 2019-12-24 | Baylor College Of Medicine | Small molecule regulators of steroid receptor coactivators and methods of use thereof |
| US11253517B2 (en) | 2016-04-08 | 2022-02-22 | Baylor College Of Medicine | Small molecule regulators of steroid receptor coactivators and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6702919A (en:Method) | 1967-08-25 |
| FR1515642A (fr) | 1968-03-01 |
| DE1522429A1 (de) | 1969-09-11 |
| BE695443A (en:Method) | 1967-09-14 |
| GB1118654A (en) | 1968-07-03 |
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