US3679428A - Spectrally sensitized photographic emulsions - Google Patents
Spectrally sensitized photographic emulsions Download PDFInfo
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- US3679428A US3679428A US57607A US3679428DA US3679428A US 3679428 A US3679428 A US 3679428A US 57607 A US57607 A US 57607A US 3679428D A US3679428D A US 3679428DA US 3679428 A US3679428 A US 3679428A
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- 239000000839 emulsion Substances 0.000 title abstract description 18
- -1 SILVER HALIDE Chemical class 0.000 abstract description 52
- 230000001235 sensitizing effect Effects 0.000 abstract description 37
- 229910052709 silver Inorganic materials 0.000 abstract description 14
- 239000004332 silver Substances 0.000 abstract description 14
- 239000000203 mixture Chemical group 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 10
- 150000001450 anions Chemical class 0.000 abstract description 10
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical class C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 abstract description 9
- 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 abstract description 8
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 abstract description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 7
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 abstract description 6
- 150000002367 halogens Chemical group 0.000 abstract description 6
- 150000001556 benzimidazoles Chemical class 0.000 abstract description 5
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 48
- 125000000217 alkyl group Chemical group 0.000 description 22
- 230000035945 sensitivity Effects 0.000 description 17
- 230000003595 spectral effect Effects 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 206010070834 Sensitisation Diseases 0.000 description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000008313 sensitization Effects 0.000 description 4
- 235000010724 Wisteria floribunda Nutrition 0.000 description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical compound C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- 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 1
- 241000575946 Ione Species 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 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
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 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
- 239000012716 precipitator Substances 0.000 description 1
- 230000001737 promoting effect Effects 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
Images
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
- G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed
Definitions
- R is an alkyl group having from l to 4 carbon atoms
- R3 and R4 which may be the same or different, each represents an alkyl group, an allyl group and an alkyl group substituted by hydroxy, alkoxy, carboxy, sulfo or mixtures thereof
- Z3 and Z4, which may be the same or dilerent each represents a non-metallic atomic group necessary to complete a benzothiazole or a benzoselenazole nucleus, which may be substituted by halogen, phenyl, alkoxyphenyl, hydroxyphenyl, carboxyphenyl, an alkyl hafving from l to 4 carbon atoms, hydroxyl, alkoxy, carboxyl, carboxylic acid ester, carbamoyl or alkyl carbamoyl groups;
- X2 is an acid anion and m is 1 or 2.
- This invention relates to a spectrally sensitized silver halide photographic emulsion and more particularly, it is concerned with a high sensitivity silver halide photographic emulsion which is supersensitized, by the use of a combination of at least two sensitizing dyes over the absorption light wavelength region of each of the sensitizing dyes.
- the spectral sensitization over the visible region is required for light-sensitive materials for photography in general, but having a high spectral sensitivity up to very long wavelengths is not always preferred from the viewpoint of tone reproduction.
- Two or more sensitizing dyes are generally used in combination in order to obtain the most suitable distribution of spectral sensitivity.
- the spectral sensitivity obtained in the case of using two or more sensitizing dyes in combination to regulate the spectral sensitivity distribution is often lower than in the case of using each of them individually.
- the spectral sensitizing action is alfected not only by the chemical structure of the sensitizing dye but also by the properties of the silver halide emulsion employed, for example, the crystal habit of the silver halide line crystals, the particle size, the halogen composition, the hydrogen ion concentration and the silver ion concentration.
- additives present in the emulsion such as, for example, inhibitors, stabilizers, sensitizers, hardeners, binders, precipitators, plasticizers, color formers and photographic dyes, have many influences thereupon, many of them acting so as to weaken the special sensitizing action.
- the spectral sensitizing action obtained by adding one sensitizing dye is superadditively strengthened by also adding therewith another sensitizing dye or organic compound, in particular, an aromatic compound.
- Another sensitizing dye or organic compound in particular, an aromatic compound.
- the action of this type is known as supersensitization.
- the use of a cyanine dye alone scarcely gives a maximum sensitivity over relatively long wavelengths, such as 625 mm. to 640 mm.
- It is therefore an object of the present invention to nd the spectral sensitization capable of raising the spectral sensitivity of a photographic light-sensitive material, in particular, to a wavelength region of 625 to 640 mm.
- Such a technique is very important for improving the productivity in making photographic light-sensitive materials.
- R represents a hydrogen atom or a lower alkyl group, such as methyl or ethyl
- R1 and R2 which may be the same or different, are selected from groups of the alkyl series, such as alkyl .groups (e.g., methyl, ethyl and propyl), allyl groups and substituted alkyl groups (e.g.,
- R1 and R2 being a substituted alkyl group of the type indicated;
- Z1 represents a non-metallic atomic group necessary to complete a heterocyclc nucleus of the naphthothiazole series (e.g., a-naphthothiazole, -naphthothiazole, 5methoxy naphthothiazole, S-ethoxy--naphthothiazole, 8-methoxya-naphthothiazole, 7 methoxy a naphthothiazole), the naphthoselenazole series (e.g., a-naphthoselenazole or naplithoselenazole), or the naphthox
- R5 represents a lower alkyl group, such as ethyl or butyl
- R3 and R4, which may be the same or dilerent each represents groups of the alkyl series, such as alkyl groups (e.g., methyl, ethyl and butyl), allyl groups and substituted alkyl groups (e.g., Z-,hydroxyethyL Z-methoxyethyl, carboxymethyl, 3-carboxypropyl, 4-carboxybutyl, 3- sulfopropyl, 4-su1fobutyl, 3-sulfoisobutyl, 2-(3-sulfopropoxy)ethyl and 2hydroxy3sulfopropyl);
- Z3 and Z4, which may be the same ordiiferent each represents a non-metallic atomic group necessary to complete a benzothiazole or a benzoselenazole nucleus which may be substituted by a group capable of promoting the alky
- the gure represents spectrograms of samples containing a dye of Formula I, a dye of Formula II and a combination thereof, respectively.
- the sensitizing dye represented by Formula I the nitrogen atom in the cyanine dye nuclei consisting of the naphthothiazole, naphthoselenamle, naphthoxazole or naphthoimidazole nucleus is substituted by at least one substituted Ialkyl group as described above, and that the cyanine dye represented by Formula II is liable to form a relatively strong J-aggregate.
- the supersensitizing action over the whole wavelength region which the dyes absorb is obtained and the spectral sensitivity distribution is regulated relatively optional by the use of, in combination, the sensitizing dye characterized by the chemical structure of Formula I and the cyanine dye represented by Formula II in suitable amounts.
- the spectral sensitivity within a wavelength region of 625 mm. to 640 mm. can be raised.
- a further feature of the presentrinvention consists in the advantage that theV supersensitization given by the sensitizing dye of Formula I'serves to markedly improve the stability and reproducivity of the spectral sensitivity obtained.
- the sensitizing dyes of the present invention are dissolved in .an aqueous solution or in a water-soluble organic solvent such as methanol, ethanol, acetone, methyl Cellosolve or pyridine and then added to a silver halide emulsion separately or as a mixture thereof.
- lStirrng by ultrasonic Waves may be applied during the dissolving of the' sensitizing dyes.
- the amount of addition, order of addition land addition procedure may be varied with the production process of the light-sensitive material.
- the amount of Vaddition of the sensitizing dyes is preferably from 1 10 mole to 5 X10-4 mole per mole of silver halide, the molar n is coated onto a suitable support, for examle, a cellulose derivative lm, a polyethylene terephthalate lm, a polycarbonate film, baryta paper, resin coated paper, synthetic paper, resin laminated paper or a glass sheet.
- sensitizing dyes -according tothe present invention are given below, these compounds being merely illustrative 'and not limiting in nature.
- Sensitizing dyes represented by Formulae I and II were separately dissolved in methanol to give a predetemined concentration (shown in Table I).
- a predetermined amount (shown in Table I) of each of the sensitizing dye H Co 0 a l/ N OCH solutions was added to the emulsion with agitation. After H minute, 7 ml. of each emulsion was applied to a glass Ems o i 5 sheet of cabinet size and dried to obtain a sample.
- the sensitizing dyes represented by Formulae I and II Metol g 2 may be synthesized in any known manner.
- Anhydrous sodium sulte g 100 dyes IA, IB, IIA, IIB, IIC, IID and IIE can be readily 4Hydroquinone g-- 5 synthesized by the methods disclosed in U.S. Pat. No. Borax g y 2 2,503,776, German Pats. Nos. 929,080 and 1,072,765 and Water to make 1000 ml.
- curve 1 is a spectrogram of the sample obtained by adding 20 ml. of sensitizing dye (IA) of No. 1 in Table I;
- curve 2 is va spectrogram of the sample obtained by adding 10 ml. of sensitizing dye (IIA) of No. 2 in Table I; and curve 3 is a spectrogram of the sample obtained by adding a mixture of 20 ml. of dye (IA) and 10 ml. of dye (IIA) according to the present invention.
- R is a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms
- Z1 is a Lnon-metallic ⁇ atomic group necessary to ⁇ complete a heterocyclic nucleus of the naphthothiazole, naphthoselenazole or naphthoxazole series
- Z2 is a non-metallic group necessary to complete a nucleus of the napthoselenazole, naphthoxazole, naphthoimidazole or benzimidazole series
- X1 is an acid anion and n is 1 or 2, and at least one sensitizing dye represented by the following Formula II:
- R is a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms
- R1 and R1 which may be the same or diterent, each represents analkyl group, an allyl group and an alkyl group substituted by hydroxy, carboxy, ⁇ sulfo or mixtures thereof, at least one of R1 and R2 being a substituted alkyl group
- Z1 is a non-metallic atomic group necessary to complete a heterocyclic nucleus of the naphthothiazole, or naphthoselenazole series
- Z1 is a non-metallic group necessary to complete a nucleus of the naphthoselenazole, naphthoimidazole or benzimidazole series
- X1- is an :acid anion and n is 1 or 2, and at least one sensitizing dye represented by the following Formula II:
- R5 is an alkyl group having from l to 4 carbon atoms
- R3 and R1 each represents a member selected from the group consisting of sulfo alkyl and hydroxyalkyl groups
- Z3 and Z4 which may be the same or different, each represents a non-metallic atomic group necessary to complete a benzothiazole or a benzoselenazole nucleus, which may be substituted by halogen, phenyl, Aalkoxyphenyl, hydroxyphenyl, carboxyphenyl, an alkyl having from l to 4 carbon atoms, hydroxyl, alkoxy, carboxyl, carboxylic acid ester, carbamoyl or alkyl carbamoyl groups;
- X1 is an acid anion and m is 1 or 2.
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44058180A JPS4825653B1 (enrdf_load_stackoverflow) | 1969-07-23 | 1969-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3679428A true US3679428A (en) | 1972-07-25 |
Family
ID=13076792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US57607A Expired - Lifetime US3679428A (en) | 1969-07-23 | 1970-07-23 | Spectrally sensitized photographic emulsions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3679428A (enrdf_load_stackoverflow) |
| JP (1) | JPS4825653B1 (enrdf_load_stackoverflow) |
| BE (1) | BE753807A (enrdf_load_stackoverflow) |
| CA (1) | CA971813A (enrdf_load_stackoverflow) |
| DE (1) | DE2036641C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2053101B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1321427A (enrdf_load_stackoverflow) |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3770449A (en) * | 1970-09-24 | 1973-11-06 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3808008A (en) * | 1970-09-10 | 1974-04-30 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3907575A (en) * | 1972-10-27 | 1975-09-23 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3922170A (en) * | 1972-07-20 | 1975-11-25 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3967967A (en) * | 1973-12-06 | 1976-07-06 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| US3977882A (en) * | 1972-07-20 | 1976-08-31 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| DE2615971A1 (de) * | 1975-04-14 | 1976-10-28 | Konishiroku Photo Ind | Lichtempfindliches farbphotographisches silberhalogenid-aufzeichnungsmaterial |
| US4028115A (en) * | 1975-08-26 | 1977-06-07 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion sensitized to red with four carbocyanine dyes |
| DE2711267A1 (de) * | 1976-03-15 | 1977-09-22 | Fuji Photo Film Co Ltd | Photographische silberhalogenidemulsion |
| US4277353A (en) * | 1980-01-07 | 1981-07-07 | Exxon Research & Engineering Co. | Oil-soluble substituted mono and bicyclic oxazolidines, their preparation and use as additives for functional fluids |
| US4282108A (en) * | 1980-01-07 | 1981-08-04 | Exxon Research & Engineering Co. | Oil-soluble spiro-[cycloalkane-oxazolidines], their preparation and use as additives and chelating agents for functional fluids |
| US4369118A (en) * | 1980-12-29 | 1983-01-18 | Exxon Research & Engineering Co. | Process of inhibiting haze in lubricating oil compositions |
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0239363A2 (en) | 1986-03-25 | 1987-09-30 | Konica Corporation | Light-sensitive silver halide photographic material feasible for high speed processing |
| US4710631A (en) * | 1984-08-28 | 1987-12-01 | Fuji Photo Film Co., Ltd. | Temperature compensation for a semiconductor light source used for exposure of light sensitive material |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP1624337A2 (en) | 2004-08-02 | 2006-02-08 | Fuji Photo Film Co., Ltd. | Silver halide holographic sensitive material and system for taking holographic images by using the same |
| EP1691237A2 (en) | 2005-02-15 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Holographic recording material and holographic recording method |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
| EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5228659B2 (enrdf_load_stackoverflow) * | 1973-04-23 | 1977-07-28 |
-
1969
- 1969-07-23 JP JP44058180A patent/JPS4825653B1/ja active Pending
-
1970
- 1970-07-21 CA CA088,783A patent/CA971813A/en not_active Expired
- 1970-07-22 GB GB3553370A patent/GB1321427A/en not_active Expired
- 1970-07-23 US US57607A patent/US3679428A/en not_active Expired - Lifetime
- 1970-07-23 FR FR707027174A patent/FR2053101B1/fr not_active Expired
- 1970-07-23 DE DE2036641A patent/DE2036641C3/de not_active Expired
- 1970-07-23 BE BE753807D patent/BE753807A/xx unknown
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3808008A (en) * | 1970-09-10 | 1974-04-30 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3770449A (en) * | 1970-09-24 | 1973-11-06 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3922170A (en) * | 1972-07-20 | 1975-11-25 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3977882A (en) * | 1972-07-20 | 1976-08-31 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| US3907575A (en) * | 1972-10-27 | 1975-09-23 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3967967A (en) * | 1973-12-06 | 1976-07-06 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| DE2615971A1 (de) * | 1975-04-14 | 1976-10-28 | Konishiroku Photo Ind | Lichtempfindliches farbphotographisches silberhalogenid-aufzeichnungsmaterial |
| US4028115A (en) * | 1975-08-26 | 1977-06-07 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion sensitized to red with four carbocyanine dyes |
| DE2711267A1 (de) * | 1976-03-15 | 1977-09-22 | Fuji Photo Film Co Ltd | Photographische silberhalogenidemulsion |
| US4152163A (en) * | 1976-03-15 | 1979-05-01 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion containing cyanine and hemicyanine sensitizing dyes |
| US4277353A (en) * | 1980-01-07 | 1981-07-07 | Exxon Research & Engineering Co. | Oil-soluble substituted mono and bicyclic oxazolidines, their preparation and use as additives for functional fluids |
| US4282108A (en) * | 1980-01-07 | 1981-08-04 | Exxon Research & Engineering Co. | Oil-soluble spiro-[cycloalkane-oxazolidines], their preparation and use as additives and chelating agents for functional fluids |
| US4369118A (en) * | 1980-12-29 | 1983-01-18 | Exxon Research & Engineering Co. | Process of inhibiting haze in lubricating oil compositions |
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US4710631A (en) * | 1984-08-28 | 1987-12-01 | Fuji Photo Film Co., Ltd. | Temperature compensation for a semiconductor light source used for exposure of light sensitive material |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0239363A2 (en) | 1986-03-25 | 1987-09-30 | Konica Corporation | Light-sensitive silver halide photographic material feasible for high speed processing |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
| EP1624337A2 (en) | 2004-08-02 | 2006-02-08 | Fuji Photo Film Co., Ltd. | Silver halide holographic sensitive material and system for taking holographic images by using the same |
| EP1691237A2 (en) | 2005-02-15 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Holographic recording material and holographic recording method |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CA971813A (en) | 1975-07-29 |
| DE2036641B2 (de) | 1974-01-10 |
| FR2053101A1 (enrdf_load_stackoverflow) | 1971-04-16 |
| GB1321427A (en) | 1973-06-27 |
| FR2053101B1 (enrdf_load_stackoverflow) | 1973-05-25 |
| DE2036641C3 (de) | 1981-02-12 |
| DE2036641A1 (de) | 1972-01-27 |
| JPS4825653B1 (enrdf_load_stackoverflow) | 1973-07-31 |
| BE753807A (fr) | 1970-12-31 |
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