US3674499A - Silver halide photographic supersensitized emulsion - Google Patents
Silver halide photographic supersensitized emulsion Download PDFInfo
- Publication number
- US3674499A US3674499A US41092A US3674499DA US3674499A US 3674499 A US3674499 A US 3674499A US 41092 A US41092 A US 41092A US 3674499D A US3674499D A US 3674499DA US 3674499 A US3674499 A US 3674499A
- Authority
- US
- United States
- Prior art keywords
- condensate
- emulsion
- sensitizing dye
- silver halide
- formalin
- 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
- 239000000839 emulsion Substances 0.000 title abstract description 49
- -1 Silver halide Chemical class 0.000 title description 40
- 229910052709 silver Inorganic materials 0.000 title description 22
- 239000004332 silver Substances 0.000 title description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 86
- 230000001235 sensitizing effect Effects 0.000 abstract description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 11
- 150000001896 cresols Chemical class 0.000 abstract description 5
- 239000000975 dye Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PSSUGHHHKLRYEN-UHFFFAOYSA-N 4-bromophenol;formaldehyde Chemical compound O=C.OC1=CC=C(Br)C=C1 PSSUGHHHKLRYEN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- DEXXACGTZUBAMY-UHFFFAOYSA-N 4-chlorophenol;formaldehyde Chemical compound O=C.OC1=CC=C(Cl)C=C1 DEXXACGTZUBAMY-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 4
- KNAJYSZHBGJAHK-UHFFFAOYSA-N 2-chlorophenol;formaldehyde Chemical compound O=C.OC1=CC=CC=C1Cl KNAJYSZHBGJAHK-UHFFFAOYSA-N 0.000 description 4
- KDYVCOSVYOSHOL-UHFFFAOYSA-N 7-methylquinoline Chemical compound C1=CC=NC2=CC(C)=CC=C21 KDYVCOSVYOSHOL-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003557 thiazoles 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
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 2
- GUXWVUVLXIJHQF-UHFFFAOYSA-N 2,5-dibromophenol Chemical compound OC1=CC(Br)=CC=C1Br GUXWVUVLXIJHQF-UHFFFAOYSA-N 0.000 description 2
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 2
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-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
- AQVKHRQMAUJBBP-UHFFFAOYSA-N 4-Bromocatechol Chemical compound OC1=CC=C(Br)C=C1O AQVKHRQMAUJBBP-UHFFFAOYSA-N 0.000 description 2
- MPCCNXGZCOXPMG-UHFFFAOYSA-N 4-bromobenzene-1,3-diol Chemical compound OC1=CC=C(Br)C(O)=C1 MPCCNXGZCOXPMG-UHFFFAOYSA-N 0.000 description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 2
- WWOBYPKUYODHDG-UHFFFAOYSA-N 4-chlorocatechol Chemical compound OC1=CC=C(Cl)C=C1O WWOBYPKUYODHDG-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- LMYVCXSKCQSIEQ-UHFFFAOYSA-N 5-methylquinoline Chemical compound C1=CC=C2C(C)=CC=CC2=N1 LMYVCXSKCQSIEQ-UHFFFAOYSA-N 0.000 description 2
- HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical class C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CYHVDCMBRUBZSS-UHFFFAOYSA-N 1,3-diethyl-2h-benzimidazole Chemical compound C1=CC=C2N(CC)CN(CC)C2=C1 CYHVDCMBRUBZSS-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
- ZAQJHSAPJIMKAM-UHFFFAOYSA-N 1-(3-ethyl-1,3-benzothiazol-2-ylidene)propan-2-one Chemical compound C1=CC=C2N(CC)C(=CC(C)=O)SC2=C1 ZAQJHSAPJIMKAM-UHFFFAOYSA-N 0.000 description 1
- QRINVLDPXAXANH-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1,3-benzoselenazole Chemical compound C1C=CC=C2[Se]CNC21 QRINVLDPXAXANH-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- REFDOIWRJDGBHY-UHFFFAOYSA-N 2-bromobenzene-1,4-diol Chemical compound OC1=CC=C(O)C(Br)=C1 REFDOIWRJDGBHY-UHFFFAOYSA-N 0.000 description 1
- DMVRIXQZYFWURI-UHFFFAOYSA-N 2-methoxy-1,3-benzoselenazole Chemical compound C1=CC=C2[se]C(OC)=NC2=C1 DMVRIXQZYFWURI-UHFFFAOYSA-N 0.000 description 1
- OJKLTHIQRARJCE-UHFFFAOYSA-N 2-methoxy-1,3-benzothiazole Chemical compound C1=CC=C2SC(OC)=NC2=C1 OJKLTHIQRARJCE-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 1
- OYTKXVQRRLZCDC-UHFFFAOYSA-N 2-thiophen-2-yl-1,3-thiazole Chemical compound C1=CSC(C=2SC=CN=2)=C1 OYTKXVQRRLZCDC-UHFFFAOYSA-N 0.000 description 1
- NFUQIJZKWLEFAT-UHFFFAOYSA-N 3-chloro-2,6-dihydroxybenzaldehyde Chemical compound ClC1=C(C(=C(O)C=C1)C=O)O NFUQIJZKWLEFAT-UHFFFAOYSA-N 0.000 description 1
- UWSONZCNXUSTKW-UHFFFAOYSA-N 4,5-Dimethylthiazole Chemical compound CC=1N=CSC=1C UWSONZCNXUSTKW-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
- IFEPGHPDQJOYGG-UHFFFAOYSA-N 4-chloro-1,3-benzothiazole Chemical compound ClC1=CC=CC2=C1N=CS2 IFEPGHPDQJOYGG-UHFFFAOYSA-N 0.000 description 1
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
- BJATXNRFAXUVCU-UHFFFAOYSA-N 4-methyl-1,3-selenazole Chemical compound CC1=C[se]C=N1 BJATXNRFAXUVCU-UHFFFAOYSA-N 0.000 description 1
- SRGCYOMCADXFJA-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-thiazole Chemical compound CC1CSC=N1 SRGCYOMCADXFJA-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
- VWMQXAYLHOSRKA-UHFFFAOYSA-N 5-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC=NC2=C1 VWMQXAYLHOSRKA-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
- 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
- QQZVCZXZPSBVML-UHFFFAOYSA-N C=O.ClC1=C(C=CC(=C1)Cl)O Chemical compound C=O.ClC1=C(C=CC(=C1)Cl)O QQZVCZXZPSBVML-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 241001328813 Methles Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- XCFIVNQHHFZRNR-UHFFFAOYSA-N [Ag].Cl[IH]Br Chemical compound [Ag].Cl[IH]Br XCFIVNQHHFZRNR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical compound C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 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
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- G03C1/08—Sensitivity-increasing substances
- G03C1/28—Sensitivity-increasing substances together with supersensitising substances
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/0025—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through an oxygen atom
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
Definitions
- R and R are each respectively alkyl groups, such as methyl, ethyl, and propyl groups; SILVER SUPER substituted alkyl groups such as B-hydroxyethyl, B-acetoxy- Keisuke Shiba, Masanao Hinata, Nobuo Tusji, Takushi ethyl YP PY fl'sulfatoethyl 2 4 3 'Y' Miyazaki, and Akira Sato, Kanagawa, Japan, assignors 5 Sulfatopropyl 3 6 3- carboxymethyl, fiyto Fuji Photo Film, Ltd., Nakanuma, Minami Ashigara e hyl, 2-(2-Carboxyethoxy)ethyl, B-ulfoethyl, 'y-sulfopro- Machi, Ashigara-Kamigun, Kanagawa, Japan
- ABS OF THE DISCLOSURE substituted alkyl group such as a hydroxyalkyl group, a
- a supersensitizing combination for use in a photograph- 1 ic emulsion comprising (1) a sensitizing dye having the general formula Q wherein the symbols R, R R R R R R X, Y, Y Q, group, and when n,,, is 0, R may be connected through the n n n n,, and m are described hereinafter, and -(2) a methine chain with a nitrogen atom in a heterocyclic ring condensate of formalin with a halogenated poly
- n n and n are respectively 0 or 1, n is 0, or 2, Q 15 an oxygen atom, a sulfur atom or NR (1) Field of the invention 'wherein R is an alkyl group such as a methyl or an ethyl
- R is an alkyl group such as a methyl or an ethyl
- This invention relates to a silver halide photographic groupi Y and Y1 each represent for example emulsion More particularly, it is concerned with a metallic atoms necessary to complete a heterocyclic nucleus of the thiazole series for exam le, thiazole, 4-methcalled supersensitlzed silver halide photographic emulsion.
- the silver halide emulsion may be 5-hydfoxybenlfllialole, 0f 6-hydf0Xybe11ZthiflZ01e), 0f the considered to be supersensitized.
- Such compounds which naphthothiazole Series p vl-naphthoflliazole, 1 do not sensitize the same spectral reigon as sensitizing p h hi y-fi- P Y- dyes are called supersensitizers.
- halogenated polyhydroxybenzene thoxazole or B naphthoxazole means a halogen-Substituted benzene having from one to (for example, 4-methylselenazole or 4-phenylselenazo'le), three hydroxyl groups in the benzene n cle s.
- Fur h of the benzselenazole series (for example, benzoselenazole, the tfir H1 halogenated Polyhydroxybenzene'formalin c011- S-chlorobenzselenazole, 5 methoxybenzselenazole, S-hydensate 0f halogenated cfesol-fol'malin condensate Will droxybenzselenazole, or tetrahydrobenzselenazole), of the hereinafter be referred to 38 formalin condensate.
- benzoselenazole the tfir H1 halogenated Polyhydroxybenzene'formalin c011- S-chlorobenzselenazole, 5 methoxybenzselenazole, S-hydensate 0f halogenated cfesol-fol'malin condensate Will droxybenzselenazole, or tetrahydrobenzselen
- naphthoselenazole eries for example -naphthoselena General Formula I zole or fl-naphthoselenazole
- thiazoline series for Y-"-- R3 R4 R5 --Y example, thiazoline or 4-methylthiazoline
- Z-quinoline series for example, quinoline, 3-methylquinoline, 5- methylquinoline, 7-methylquinoline, S-methylquinoline, 6- chloroquinoline, 8 chloroquinoline, 6-methoxyquinoline, G-ethoxyquinoline, 6-hydroxyquinoline or 8-hydroxyquinoline
- 4-quinoline series for example, quinoline, 6-methoxyquinoline, 7-methylquinoline or S-methylquinoline
- the l-isoquinoline series for example, isoquinoline series (for example, isoquinoline itself), of the benzimidazole series (for example, 1,3-diethylbenzimidazole 0r l-ethy
- halogenated polyhydroxybenzene used in the invention is represented by the following general formula (Xrh wherein n ranges from 1 to 3, n ranges from 1 to 3 wherein simultaneously n and n cannot both be 3, wherein X is achlorine or bromine atom.
- Examples of the compounds represented by the above mentioned general formula are o-chlorophenol, m-chlorophenol, p-chlorophenol, o-bromophenol, m-bromophenol, p-bromophenol, 2,4-dichloropheuol, 2,6-dichlorophenol, 2, S-dichlorophenol, 2,4-dibromophenol, 2,5-dibromophenol, 2 chlorohydroquinone, 4-chlororesorcinol, 4-chlorocatechol, Z-bromohydroquinone, 4-bromores0rcinol, 4-bromoresorcinol, 4-bromocatechol, and 2,4,5-trichlorophenol.
- halogenated cresol used in the invention is represented by the following general formula.
- X is a chlorine or bromine atom.
- Examples of compounds represented by the above mentioned general formula are -chloro-m-cresol, p-chloro-ocresol and p-chloro-m-cresol.
- Synthesis of the condensate of the halogenated polyhydroxybenzene and formalin can be carried out according to the concentional synthesis method for a phenolformaldehyde resin of the novolak type.
- the general synthesis method is as follows: The halogenated polyhydroxybenzene is dissolved or dispersed in water, to which a mineral acid, such as concentrated hydrochloric acid or sulfuric acid, and 37% formalin (aqueous solution of formaldehyde) are added, and the mixture is heated at C. for from 30 minutes to 1 hour with agitation. The reaction can be carried out under a pressure in an autoclave. After the reaction, the product is poured in cold water and the resultant precipitate is purified.
- a mineral acid such as concentrated hydrochloric acid or sulfuric acid
- formalin aqueous solution of formaldehyde
- Another example is as follows: 400 parts of o-chlorophenol is dispersed in 1,000 parts of water with vigorous agitation, to which 25 parts of 35% hydrochloric acid and 250 parts of 37% formalin are then added. Then, the reaction mixture is heated at 100 C. with stirring and held for 30 minutes. 20 parts of concentrated hydrochloric acid is added additionally and the reaction is further continued for another 30 minutes. 20 parts of concentrated hydrochloric acid is then added and stirred to give a white turbidity. After about 1 hour and 30 minutes, the stirring is stopped and the mixture is transferred into 3,000 parts of cold water with agitation. The resulting precipitate is filtered, not dried, re-dissolved in 500 parts of methanol and precipitated again with cold water. Then, the precipitate is filtered and dried to obtain the desired product.
- the formalin condensate used in the invention has a condensation unit (degree of polymerization) of from 2 to 10 similar to the conventional novolak resins.
- a degree of polymerization of from 2 to 10, preferably from 2 to 5, as well as a molecular weight of from 250 to 750 is desired.
- the sensitizing dye used in the invention may be synthesized in known manner per se such as the method as disclosed in US. Pat. 2,947,680. Several synthetic examples are as follows:
- ing dye is incorporated in an emulsion.
- the sensitizing dye of the invention is ordinarily used in a silver halide emulsion at a concentration of from 0.002 to 0.2 g./silver halide g. mol and the formalin condensate is used at a concentration of from 0.1 to 5.0 g./silver halide g. mol, the concentration ratio of the sensitizing dye and formalin condensate preferably ranging from 1:5 to 1:500.
- Addition of the sensitizing dye can be carried out using methods known to those skilled in the art.
- the formalin condensate can be added to a silver halide emulsion in the form of a solution in an organic solvent such as methanol or ethanol.
- the sensitizing dye and formalin condensate are preferably added to an emulsion before the application of the emulsion.
- the order of addition to the emulsion is not limited particularly. Any of the sensitizing dyes and the formalin condensate can be added firstly or the both can be added in admixture. Furthermore, they can be added to an emulsion after water washing and during ageing.
- a conventional gelatino-silver halide emulsion is used but other resinous materials and cellulose derivatives, compatible with photographic materials, can be used of course.
- Silver halides such as silver chloride, silver bromide, silver iodobromide, silver chlorobromide or silver chloriodobromide, can be used for the emulsion of the invention.
- the emulsion of the invention also can contain conventional additives such as chemical sensitizers, fog inhibitors, stabilizers, hardeners, coating aids, plasticizers, development accelerators, color tone regulators, whitening agents and couplers.
- the emulsion can be applied in the conventional manner to a suitable support such as a glass sheet, a cellulose derivative film, a synthetic resin film or a baryta paper.
- a silver halide photographic emulsion containing the combination of 1) at least one sensitizing dye having the following general formula wherein Y and Y each represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of the thiazole series, of the benzthiazole series, of the naphthopercent) was used.
- the development is carried out at 20 20 thiazole series, of the oxazole series, of the benzoxa- C. for 2 mnutes with a developer as shown in Table 2 zole series, of the napthoxazole series, of the thiazofor Examples 1 to 16 and at 20 C.
- halogenated polyhydrozybenzene is selected from the group consisting of o-chlorophenol, m-chlorophenol, p-chlorophenol, o-bromophenol, m-bromophenol, p-bromophenol, 2,4-dichlorophenol, 2,6-dichlorophenol, 2,5-dichlorophenol, 2,4-dibromophenol, 2,5-dibromophenol, 2-chlorohydroquinone, 4-chlororesorcinol, 4-chlorocatechol, 2-bromohydroquinone, 4-bromoresorcinol, 4-bromocatechol, and 2,4,5-trichlorophenol.
- halogenated cresol is selected from the group consisting of 6-ch1orom-cresol, p-chloro-o-cresol, and p-chloro-m-cresol.
- the combination of the sensitizing dye with the formalin condensation is selected from the group consisting of o-chlorophenolformaldehyde condensate, p-chlorophenol-formaldehyde condensate, p-brornophenol-formaldehyde condensate, 2,4- dichlorophenol-formaldehyde condensate, 2-chlorohydroquinone-formaldehyde condensate, 4-chlororesorcinolformaldehyde condensate and 6-ch10ro-m-cresol-formaldehyde condensate, wherein the sensitizing dye is and p-chlorophenol-formaldehyde condensate.
- a photographic light-sensitive element comprising a support having thereon at least one layer containing the silver halide emulsion of claim 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44041169A JPS4925500B1 (fr) | 1969-05-27 | 1969-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3674499A true US3674499A (en) | 1972-07-04 |
Family
ID=12600907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US41092A Expired - Lifetime US3674499A (en) | 1969-05-27 | 1970-05-27 | Silver halide photographic supersensitized emulsion |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3674499A (fr) |
| JP (1) | JPS4925500B1 (fr) |
| BE (1) | BE750997A (fr) |
| CA (1) | CA934595A (fr) |
| DE (1) | DE2026091C3 (fr) |
| FR (1) | FR2092173A5 (fr) |
| GB (1) | GB1310760A (fr) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971664A (en) * | 1970-10-27 | 1976-07-27 | Fuji Photo Film Co., Ltd. | Fine grain silver halide emulsions with polyheteronuclear sensitizing dyes |
| EP0219113A2 (fr) | 1985-10-15 | 1987-04-22 | Fuji Photo Film Co., Ltd. | Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent |
| EP0253390A2 (fr) | 1986-07-17 | 1988-01-20 | Fuji Photo Film Co., Ltd. | Support photographique et matériau photosensible couleur |
| EP0313083A2 (fr) | 1987-10-22 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0317983A2 (fr) | 1987-11-27 | 1989-05-31 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0318987A1 (fr) | 1987-12-02 | 1989-06-07 | Fuji Photo Film Co., Ltd. | Matériau photographique directement positif sensible à la lumière |
| EP0320939A2 (fr) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0456210A2 (fr) | 1990-05-09 | 1991-11-13 | Fuji Photo Film Co., Ltd. | Méthode pout traiter un matériau photographique à l'halogénne d'argent et matériau photosensible pour photographie |
| US5439786A (en) * | 1991-11-12 | 1995-08-08 | International Paper Company | Photographic emulsions and materials with reduced pressure sensitivity |
-
1969
- 1969-05-27 JP JP44041169A patent/JPS4925500B1/ja active Pending
-
1970
- 1970-05-22 GB GB2499470A patent/GB1310760A/en not_active Expired
- 1970-05-26 CA CA083948A patent/CA934595A/en not_active Expired
- 1970-05-26 FR FR7019098A patent/FR2092173A5/fr not_active Expired
- 1970-05-27 DE DE2026091A patent/DE2026091C3/de not_active Expired
- 1970-05-27 BE BE750997D patent/BE750997A/fr unknown
- 1970-05-27 US US41092A patent/US3674499A/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971664A (en) * | 1970-10-27 | 1976-07-27 | Fuji Photo Film Co., Ltd. | Fine grain silver halide emulsions with polyheteronuclear sensitizing dyes |
| EP0219113A2 (fr) | 1985-10-15 | 1987-04-22 | Fuji Photo Film Co., Ltd. | Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent |
| EP0253390A2 (fr) | 1986-07-17 | 1988-01-20 | Fuji Photo Film Co., Ltd. | Support photographique et matériau photosensible couleur |
| EP0313083A2 (fr) | 1987-10-22 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0317983A2 (fr) | 1987-11-27 | 1989-05-31 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0318987A1 (fr) | 1987-12-02 | 1989-06-07 | Fuji Photo Film Co., Ltd. | Matériau photographique directement positif sensible à la lumière |
| EP0320939A2 (fr) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Matériau photographique couleur à l'halogénure d'argent |
| EP0456210A2 (fr) | 1990-05-09 | 1991-11-13 | Fuji Photo Film Co., Ltd. | Méthode pout traiter un matériau photographique à l'halogénne d'argent et matériau photosensible pour photographie |
| US5439786A (en) * | 1991-11-12 | 1995-08-08 | International Paper Company | Photographic emulsions and materials with reduced pressure sensitivity |
Also Published As
| Publication number | Publication date |
|---|---|
| CA934595A (en) | 1973-10-02 |
| FR2092173A5 (fr) | 1972-01-21 |
| JPS4925500B1 (fr) | 1974-07-01 |
| GB1310760A (en) | 1973-03-21 |
| DE2026091A1 (de) | 1970-12-17 |
| DE2026091B2 (de) | 1973-03-15 |
| DE2026091C3 (de) | 1973-09-27 |
| BE750997A (fr) | 1970-11-03 |
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