US3776739A - Spectrally sensitized silver halide photographic emulsion - Google Patents
Spectrally sensitized silver halide photographic emulsion Download PDFInfo
- Publication number
- US3776739A US3776739A US00115550A US3776739DA US3776739A US 3776739 A US3776739 A US 3776739A US 00115550 A US00115550 A US 00115550A US 3776739D A US3776739D A US 3776739DA US 3776739 A US3776739 A US 3776739A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- group
- photographic emulsion
- emulsion
- 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 claims abstract description 45
- -1 silver halide Chemical class 0.000 title claims abstract description 34
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 30
- 239000004332 silver Substances 0.000 title claims abstract description 30
- 230000001235 sensitizing effect Effects 0.000 claims abstract description 34
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 8
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QMUXKZBRYRPIPQ-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzothiazole Chemical compound C1=C(C)C(C)=CC2=C1SC=N2 QMUXKZBRYRPIPQ-UHFFFAOYSA-N 0.000 claims description 3
- SEBIXVUYSFOUEL-UHFFFAOYSA-N 5-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC=NC2=C1 SEBIXVUYSFOUEL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- BREUOIWLJRZAFF-UHFFFAOYSA-N 1,3-benzothiazol-5-ol Chemical compound OC1=CC=C2SC=NC2=C1 BREUOIWLJRZAFF-UHFFFAOYSA-N 0.000 claims description 2
- KFDDRUWQFQJGNL-UHFFFAOYSA-N 5-bromo-1,3-benzothiazole Chemical compound BrC1=CC=C2SC=NC2=C1 KFDDRUWQFQJGNL-UHFFFAOYSA-N 0.000 claims description 2
- DUMYZVKQCMCQHJ-UHFFFAOYSA-N 5-chloro-1,3-benzoselenazole Chemical compound ClC1=CC=C2[se]C=NC2=C1 DUMYZVKQCMCQHJ-UHFFFAOYSA-N 0.000 claims description 2
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 claims description 2
- AHIHYPVDBXEDMN-UHFFFAOYSA-N 5-methoxy-1,3-benzoselenazole Chemical compound COC1=CC=C2[se]C=NC2=C1 AHIHYPVDBXEDMN-UHFFFAOYSA-N 0.000 claims description 2
- PNJKZDLZKILFNF-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2SC=NC2=C1 PNJKZDLZKILFNF-UHFFFAOYSA-N 0.000 claims description 2
- LDDVDAMRGURWPF-UHFFFAOYSA-N 5-methyl-1,3-benzoselenazole Chemical compound CC1=CC=C2[se]C=NC2=C1 LDDVDAMRGURWPF-UHFFFAOYSA-N 0.000 claims description 2
- WNQUVISWQMJLHS-UHFFFAOYSA-N 6-ethoxy-5-methyl-1,3-benzothiazole Chemical compound C1=C(C)C(OCC)=CC2=C1N=CS2 WNQUVISWQMJLHS-UHFFFAOYSA-N 0.000 claims description 2
- NWEHEPFZSDXPBK-UHFFFAOYSA-N methyl 1,3-benzoselenazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2[se]C=NC2=C1 NWEHEPFZSDXPBK-UHFFFAOYSA-N 0.000 claims description 2
- UQGOTDUTYINDJD-UHFFFAOYSA-N methyl 1,3-benzothiazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2SC=NC2=C1 UQGOTDUTYINDJD-UHFFFAOYSA-N 0.000 claims description 2
- UUJOCRCAIOAPFK-UHFFFAOYSA-N 1,3-benzoselenazol-5-ol Chemical compound OC1=CC=C2[se]C=NC2=C1 UUJOCRCAIOAPFK-UHFFFAOYSA-N 0.000 claims 1
- GWKNDCJHRNOQAR-UHFFFAOYSA-N 5-ethoxy-1,3-benzothiazole Chemical compound CCOC1=CC=C2SC=NC2=C1 GWKNDCJHRNOQAR-UHFFFAOYSA-N 0.000 claims 1
- AAKPXIJKSNGOCO-UHFFFAOYSA-N 5-phenyl-1,3-benzothiazole Chemical compound C=1C=C2SC=NC2=CC=1C1=CC=CC=C1 AAKPXIJKSNGOCO-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract description 8
- 125000004964 sulfoalkyl group Chemical group 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 150000001450 anions Chemical class 0.000 abstract description 4
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical class C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 34
- 230000035945 sensitivity Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 206010070834 Sensitisation Diseases 0.000 description 4
- 235000010724 Wisteria floribunda Nutrition 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LKYACPKTRPDPLE-UHFFFAOYSA-N C1=NC(C=CC=C2)=C2[S+]1C1=CC=CC=C1 Chemical compound C1=NC(C=CC=C2)=C2[S+]1C1=CC=CC=C1 LKYACPKTRPDPLE-UHFFFAOYSA-N 0.000 description 1
- ZYZQNUBOMHNNED-UHFFFAOYSA-N CCO[S+]1C(C=CC=C2)=C2N=C1 Chemical compound CCO[S+]1C(C=CC=C2)=C2N=C1 ZYZQNUBOMHNNED-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 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
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation 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
- 229910021538 borax Inorganic materials 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000006081 fluorescent whitening agent 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
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 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
- 150000003839 salts Chemical class 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 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
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- G03C1/10—Organic substances
- G03C1/12—Methine and polymethine dyes
- G03C1/14—Methine and polymethine dyes with an odd number of CH groups
- G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups
-
- 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
Definitions
- the emulsion is highly sensitive to red light.
- the present invention generally relates to a silver halide photographic emulsion containing a novel sensitizing dye. More particularly, the present invention relates to a silver halide photographic emulsion having a high sensitivity to red.
- the present invention provides-a silver halide photographic emulsion which is highly sensitive to red.
- the present invention can be achievedby incorporating a novel sensitizing dye into a silver halide photographic emulsion.
- the novel sensitizing dye is represented by the following general formula (I):
- Z and Z represent the atomic groups neces sary to complete a benzothiazole nucleus (for example, the nucleus of benz'othiazole, 5-chlorobenzothiazole, 5-bromobenzothiazole, 5-methylbenzothiazole, 5,6-dimethylbenzothiazole, S-phenylbenzothiazole, 5- methoxybenzothiazole, S-ethoxybenzothiazole, 5- methoxycarbonylbenzothiazole, 5- hydroxybenzothiazole, 5-methyl-6-ethoxybenzothiazole, and the like), a benzoselenazole nucleus (for example, the nucleus of benzoselenazole, 5- chlorobenzoselenazole, 5-methylbenzoselenazole, 5- methoxybenzoselenazole, S-hydroxybenzoselenazole, 5-methoxycarbonylbenzoselenazole, and the like) or a naphtho
- novel sensitizing dyes of the general formula (i) employed in accordance with the present invention can be prepared in a conventional manner. For example, they maybe readily synthesized by one skilled in the art in the manner described in US. Pat. No. 2,503,776, in German Patent No. 929,080, or in German Patent No. l,072,765.
- novel sensitizing dyes represented by the general formula (l) can be prepared by reacting a compound represented by the following general formula I CH:
- R ')n (II) wherein Z, R, X and n have the same meaning asae fined in the above-described general formula (I), and R" represents an alkyl group, such as a methyl and an ethyl group, with a compound repre'sented by thefollowing general formula (III):
- reaction can be effected by heating the reactants-under reflux in a suitable solvent, such as methanol, ethanol and isopropanol, in the presence of a basic condensing agent, such as triethylamine.
- a suitable solvent such as methanol, ethanol and isopropanol
- the sensitizing dyes employed according to the present invention are capable of spectrally sensitizing a silver halide photographic emulsion. They are particularly effective in broadening the spectrally sensitizable region of a gelatino-silver halide photographic em'ulsion. They are also capable of sufficiently sensitizing a photographic emulsion containing a hydrophilic colloid other than gelatin, for example, agar collodion, watersoluble cellulose derivatives, polyvinyl alcohol and other synthetic or natural hydrophilic resins. They are further effective as sensitizing dyes for use in electrophotographs prepared by the zinc oxide method.
- various kinds of the silver salts for example, silver bromide and mixed silver halides, such as silver iodobromide, silver chlorobromide and silver chloroiodobromide, can be used.
- one or more than one of the sensitizing dyes have only to be incorporated into a photographic emulsion in any conventional manner.
- the dyes are dissolved in a suitable solvent, such as methanol and ethanol, and the resulting solution is added into the photographic emulsion.
- the amount of the sensitizing dye incorporated into the emulsion can be varied over a wide range gf flrorr 5 to 200 mg/kg of theemulsion containing 0.5 mole of silver halide, depending upon the effect desired.
- additives such as sensitizers, stabilizers, toning agents, film hardening agents, surface active agents, antifogging agents, plasticizers,
- the photographic emulsion according to the present invention may be coated in a conventional manner on a suitable support, suchasa glass sheet, a cellulose derivative film, a synthetic resin film, and a 'baryta-coated paper.
- a suitable support such as a glass sheet, a cellulose derivative film, a synthetic resin film, and a 'baryta-coated paper.
- the sensitivity to red was expressed as relative sensitivity to red with respect to that estimated as 100 for Sensitizing Dye B which was obtained by its exposure to light using Fuji 4 filter (red filter).
- the silver halide photographic emulsion of the present invention provides superior photographic properties. e.g., higher red sensitivity, to the silver halide photographic emulsion containing a sensitizing dye outside the scope of the present invention.
- Dye #141 4 A silver halide photographic emulsion as claimed in claim 1, wherein the amount of the sensitizing dye ranges from to 200 mg of dye per kg of emulsion containing 0.5 mole of silver halide.
- a photographic light-sensitive material comprising H: a support having thereon at least one layer containing A; the silver halide emulsion as claimed in claim 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45013284A JPS4842174B1 (enExample) | 1970-02-16 | 1970-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3776739A true US3776739A (en) | 1973-12-04 |
Family
ID=11828885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00115550A Expired - Lifetime US3776739A (en) | 1970-02-16 | 1971-02-16 | Spectrally sensitized silver halide photographic emulsion |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3776739A (enExample) |
| JP (1) | JPS4842174B1 (enExample) |
| BE (1) | BE762957A (enExample) |
| DE (1) | DE2107359C3 (enExample) |
| FR (1) | FR2078587A5 (enExample) |
| GB (1) | GB1340126A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501811A (en) * | 1982-10-16 | 1985-02-26 | Mitsubishi Paper Mills, Ltd. | Process for making lithographic printing plates |
| US5326876A (en) * | 1991-06-26 | 1994-07-05 | Fuji Photo Film Co., Ltd. | Process for preparing an alkyl sulfonate derivative |
-
1970
- 1970-02-16 JP JP45013284A patent/JPS4842174B1/ja active Pending
-
1971
- 1971-02-15 FR FR7104945A patent/FR2078587A5/fr not_active Expired
- 1971-02-15 BE BE762957A patent/BE762957A/xx unknown
- 1971-02-16 US US00115550A patent/US3776739A/en not_active Expired - Lifetime
- 1971-02-16 DE DE2107359A patent/DE2107359C3/de not_active Expired
- 1971-04-19 GB GB2194071A patent/GB1340126A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501811A (en) * | 1982-10-16 | 1985-02-26 | Mitsubishi Paper Mills, Ltd. | Process for making lithographic printing plates |
| US5326876A (en) * | 1991-06-26 | 1994-07-05 | Fuji Photo Film Co., Ltd. | Process for preparing an alkyl sulfonate derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2107359B2 (de) | 1973-11-15 |
| BE762957A (fr) | 1971-07-16 |
| DE2107359A1 (de) | 1971-09-02 |
| GB1340126A (en) | 1973-12-12 |
| JPS4842174B1 (enExample) | 1973-12-11 |
| FR2078587A5 (enExample) | 1971-11-05 |
| DE2107359C3 (de) | 1974-06-20 |
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