US3681080A - Silver halide photographic emulsion - Google Patents
Silver halide photographic emulsion Download PDFInfo
- Publication number
- US3681080A US3681080A US57766A US3681080DA US3681080A US 3681080 A US3681080 A US 3681080A US 57766 A US57766 A US 57766A US 3681080D A US3681080D A US 3681080DA US 3681080 A US3681080 A US 3681080A
- Authority
- US
- United States
- Prior art keywords
- agbr
- sulfobutyl
- groups
- silver halide
- halide photographic
- 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 52
- -1 Silver halide Chemical class 0.000 title abstract description 36
- 229910052709 silver Inorganic materials 0.000 title abstract description 29
- 239000004332 silver Substances 0.000 title abstract description 29
- 230000001235 sensitizing effect Effects 0.000 abstract description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001450 anions Chemical class 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 8
- 239000011593 sulfur Substances 0.000 abstract description 8
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical group 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 63
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 53
- 206010070834 Sensitisation Diseases 0.000 description 22
- 230000008313 sensitization Effects 0.000 description 22
- 230000035945 sensitivity Effects 0.000 description 21
- 230000003595 spectral effect Effects 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004964 sulfoalkyl group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 5
- 235000010724 Wisteria floribunda Nutrition 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 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
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 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
- 229920001817 Agar Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100455877 Caenorhabditis elegans misc-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- XCFIVNQHHFZRNR-UHFFFAOYSA-N [Ag].Cl[IH]Br Chemical compound [Ag].Cl[IH]Br XCFIVNQHHFZRNR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000004429 atom Chemical group 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
- 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000004081 cilia Anatomy 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000003897 fog Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- R1 (X1 wherein Z and Z which may be the same or different, are sulfur or selenium atoms; R; is hydrogen or alkyl having from 1 to 4 carbon atoms; W is hydrogen, halogen, an alkyl group having from 1 to 4 carbon atoms, alkoxy, hydroxyl, or aryl; R and R which may be the same or difierent, are ethyl, n-propyl, 'y-sulfopropyl, 'y-sulfobutyl, 6-sulfobutyl, or vinylmethyl groups with the proviso that R and R may not simultaneously be sulfoalkyl groups selected from the group consisting of 'y-sulfopropyl, 'y-sulfobutyl and fi-sulfobutyl groups, at least one of R and R being -sulfopropyl, 'y-rsulfobutyl or a-sulfobutyl when R
- R4 a h wherein Z and 2,, which may be the same or diiferent, are sulfur or selinium atoms; R, and R which may be the same or difierent, are alkyl groups having from 1 to 4 carbon atoms, sulfoalkyl groups, carboxyalkyl groups or allyl groups; X is an anion; and n is 0 or 1, nbeing 0 when an intramolecular salt is formed.
- This invention relates to a silver halide photographic emulsion, in particular, an emulsion supersensitized by using a combination of two different types of sensitizing dyes, and more particularly, it is concerned with a silver halide photographic emulsion having a high red sensitivity, wherein the spectral sensitization maximum is within a range of 625-660 m,u.
- the spectral sensitization in the case of using two or more sensitizing dyes is generally less than in the case of using each of the sensitizing dyes above, but the use of ditferent types of sensitizing dyes in combination, in some cases, produces a remarkable rise in the spectral sensitization as compared with the case of using each of them individually. This phenomenon is called supersensitization of the sensitizing dyes. Sometimes the sensitization wavelength region falls in between these regions when the dyes are individually used.
- a desired spectral sensitization wavelength region may be sensitized, a higher spectral sensitization than occurs when using them individually may be obtained through their interaction and the spectral sensitization wavelength region may be adjusted to a desired sensitization wavelength region.
- the principal object of the present invention can be accomplished by incorporating in a silver halide photographic emulsion sensitizing dyes represented by the following general Formulae I and II, in combination:
- Z, and Z which may be the same or different, are either sulfur or selenium atoms;
- R is hydrogen or a lower alkyl group such as methyl or ethyl:
- W is hydrogen, halogen (such as chlorine or bromine), a lower alkyl group .(such as methyl or ethyl group), alkoxy (such as methoxy or ethoxy), hydroxyl or aryl (such as phenyl);
- R and R which may be the same or dilferent are ethyl, n-propyl, -sulfopropyl, 'y-sulfobutyl, a-sulfobutyl or vinylmethyl groups with the proviso that R and R may not simultaneously be sulfoalkyl groups selected from the group consisting of 'y-sulfopropyl, 'y-sulfobutyl and E-sulfobutyl groups, at least one of R and R being
- R are either sulfur or selenium atoms
- R; and R which may be the same or different, are lower alkyl groups (such as methyl and ethyl), substituted alkyl groups (such as sulfoalkyl and carboxyalkyl) and allyl groups (such as vinylmethyl);
- X is an anion such as halogen, perchlorate, thiocyanate, benzenesulfonate, ethylsulfate, p toluenesulfonate, methylsulfate, and the like; and n is or 1, n being 0 when an intramolecular salt is formed.
- sensitizing dyes represented by Formulae I and II in combination gives a remark-able supersensitizing efiect and a high red sensitivity over a spectral sensitization wavelength region of 625 660 m Furthermore, the sensitizing dyes of the present invention are available for general black-and-white high sensitivity photographic materials since the combination eifect of the sensitizing dyes represented by Formulae I and II according to the present invention is not afl ected by the further addition of a known green-sensitive sensitizing dye.
- sensitizing dyes of the present invention are merely illustrative, and not limiting in nature.
- sensitizing dyes used in the present invention can readily be synthesized by suitable methods known to those skilled in the art, for example, the methods disclosed in US. Pats. Nos. 2,647,051 and 2,503,776 and German Pats. Nos. 929,080 and 1,072,765.
- the method of spectral sensitization according to the present invention is suitable for the spectral sensitization of not only gelatino-silver halide emulsions but also emulsions containing a hydrophilic colloid other than gelatin, for example, agar, water-soluble cellulose derivatives, polyvinyl alcohol and other synthetic or natural hydrophilic resins.
- a mixed silver halide emulsion such as silver iodobromide or silver chloroiodobromide is preferably used.
- Preparation of a spectrally sensitized photographic emulsion according to the present invention may be carried out by incorporating the sensitizing dyes (I) and (II) in a photographic emulsion in a conventional manner.
- the dyes are added to an emulsion in the form of a solution in a suitable solvent such as methanol or ethanol. 1
- the molar ratio of sensitizing dye (I) to dye (II), incorporated in an emulsion, may be varied within a wide range of from 9:1 to 1:9, depending on the desired effect.
- the photographic emulsion of the present invention may be subjected to hypersensitization, as well as supersensitization, in any known manner.
- commonly used additives for example, sensitizers, stabilizers, color tone regulators, hardeners, surfactants, fog inhibitors, plasticizers, development accelerators, color formers and fluorescent whitening agents may be added to the emulsion in any conventional manner.
- the photographic emulsion of this invention may be applied in any conventional manner to a suitable support such as a glass sheet, a cellulose derivative film, a synthetic resin film or a baryta paper.
- Table 2 are shown the spectral sensitivity and sensitization maximum in the case of adding sensitizing dye (I) only.
- Table 3 are shown the spectral sensitivity and sensitization maximum in the case of adding sensitizing dye (II) only.
- Table 4 are shown the spectral sensitivity and sensitization maximum in the case of adding the typical sensitizing dyes selected from sensitizing dyes (I) and (II) in combination.
- Table 5 are shown the spectral sensitivity and sensitization maximum in the case of using sensitizing dyes (I) and (II) with known greensensitive sensitizing dyes A or B in combination.
- the red sensitivity is shown by the relative sensitivity to that of sensitizing dye II-6 being 100 when exposed using a Fuji No. 7 Filter (red filter).
- Such known green-sensitive sensitizing dyes used in combination with sensitizing dyes (I) and (II) have, for example, the following chemical structures:
- Dyes I and II may be added to the emulsion in an amount of from 0.008 to 0.4 mg. mole per kg. of emulsion.
- Z, and Z which may be the same or different, are sulfur or selenium atoms;
- R is hydrogen or alkyl having from 1 to 4 carbon atoms;
- W is hydrogen, halogen, an alkyl group having from 1 to 4 carbon atoms; alkoxy, hydroxyl, or aryl;
- R; and R which may be the same or difierent are ethyl, n-propyl, -sulfopropyl, 'y-sulfobutyl, a-sulfobutyl, or vinylmethyl groups with the proviso that R and R may not simultaneously be sulfoalkyl groups selected from the group consisting of -sulfopropyl, -sulfobutyl and a-sulfobutyl groups, one of R and R being 'y-sulfopropyl, -sulfobutyl or 6-sulfobutyl when R is an alkyl group having from 1
- RzOOC wherein Z;, and Z which may be the same or different, are sulfur or selenium atoms; R and R which may be the same or different, are alkyl groups having from 1 to 4 carbon atoms, sulfoalkyl groups, carboxyalkyl groups or allyl groups; X is an anion; and n is 0 or 1, n being 0 when an intramolecular salt is formed.
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44058179A JPS4910694B1 (enrdf_load_html_response) | 1969-07-23 | 1969-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3681080A true US3681080A (en) | 1972-08-01 |
Family
ID=13076761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US57766A Expired - Lifetime US3681080A (en) | 1969-07-23 | 1970-07-23 | Silver halide photographic emulsion |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3681080A (enrdf_load_html_response) |
| JP (1) | JPS4910694B1 (enrdf_load_html_response) |
| BE (1) | BE753808A (enrdf_load_html_response) |
| CA (1) | CA960502A (enrdf_load_html_response) |
| DE (1) | DE2036640B2 (enrdf_load_html_response) |
| FR (1) | FR2055460A5 (enrdf_load_html_response) |
| GB (1) | GB1309415A (enrdf_load_html_response) |
Cited By (4)
| 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 |
| US4138551A (en) * | 1975-03-18 | 1979-02-06 | Ciba-Geigy Ag | Spectral sensitization of photographic material and new spectral sensitizers |
| US5700623A (en) * | 1997-01-21 | 1997-12-23 | Eastman Kodak Company | Thermally stable photographic bar code label containing an antistatic layer |
| US5747232A (en) * | 1997-02-27 | 1998-05-05 | Eastman Kodak Company | Motion imaging film comprising a carbon black-containing backing and a process surviving conductive subbing layer |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54166995U (enrdf_load_html_response) * | 1978-05-12 | 1979-11-24 | ||
| JPS63184100U (enrdf_load_html_response) * | 1987-05-19 | 1988-11-28 | ||
| JPH0375798U (enrdf_load_html_response) * | 1989-11-21 | 1991-07-30 |
-
1969
- 1969-07-23 JP JP44058179A patent/JPS4910694B1/ja active Pending
-
1970
- 1970-07-21 CA CA088,782A patent/CA960502A/en not_active Expired
- 1970-07-22 FR FR7026998A patent/FR2055460A5/fr not_active Expired
- 1970-07-23 BE BE753808D patent/BE753808A/xx unknown
- 1970-07-23 US US57766A patent/US3681080A/en not_active Expired - Lifetime
- 1970-07-23 GB GB3574270A patent/GB1309415A/en not_active Expired
- 1970-07-23 DE DE19702036640 patent/DE2036640B2/de active Granted
Cited By (4)
| 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 |
| US4138551A (en) * | 1975-03-18 | 1979-02-06 | Ciba-Geigy Ag | Spectral sensitization of photographic material and new spectral sensitizers |
| US5700623A (en) * | 1997-01-21 | 1997-12-23 | Eastman Kodak Company | Thermally stable photographic bar code label containing an antistatic layer |
| US5747232A (en) * | 1997-02-27 | 1998-05-05 | Eastman Kodak Company | Motion imaging film comprising a carbon black-containing backing and a process surviving conductive subbing layer |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2036640C3 (enrdf_load_html_response) | 1973-12-06 |
| BE753808A (fr) | 1970-12-31 |
| DE2036640B2 (de) | 1973-05-17 |
| DE2036640A1 (de) | 1971-02-11 |
| CA960502A (en) | 1975-01-07 |
| FR2055460A5 (enrdf_load_html_response) | 1971-05-07 |
| JPS4910694B1 (enrdf_load_html_response) | 1974-03-12 |
| GB1309415A (en) | 1973-03-14 |
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