US3660096A - Speed increasing additives for non-silver light sensitive systems - Google Patents
Speed increasing additives for non-silver light sensitive systems Download PDFInfo
- Publication number
- US3660096A US3660096A US746008A US3660096DA US3660096A US 3660096 A US3660096 A US 3660096A US 746008 A US746008 A US 746008A US 3660096D A US3660096D A US 3660096DA US 3660096 A US3660096 A US 3660096A
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- US
- United States
- Prior art keywords
- composition
- compound
- represented
- photographic
- addition
- 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
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- 229910052709 silver Inorganic materials 0.000 title abstract description 4
- 239000004332 silver Substances 0.000 title abstract description 4
- 239000000654 additive Substances 0.000 title description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims abstract description 11
- 239000012190 activator Substances 0.000 claims description 7
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical class C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 20
- 239000000975 dye Substances 0.000 abstract description 14
- 235000010290 biphenyl Nutrition 0.000 abstract description 3
- 239000004305 biphenyl Substances 0.000 abstract description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- IWYYIZOHWPCALJ-UHFFFAOYSA-N 4-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C=C1 IWYYIZOHWPCALJ-UHFFFAOYSA-N 0.000 description 5
- -1 5-[3-ethyl-2(3H) benzoxazolylidene-ethylidene]- 3-phenyl-2phenylimino-4- thiazolidinone Chemical compound 0.000 description 5
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 3
- 239000005041 Mylar™ Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052736 halogen Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 3
- 239000011022 opal Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QFVDKARCPMTZCS-UHFFFAOYSA-N methylrosaniline Chemical compound C1=CC(N(C)C)=CC=C1C(O)(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 QFVDKARCPMTZCS-UHFFFAOYSA-N 0.000 description 2
- 229960003926 methylrosaniline Drugs 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PLPFBVXTEJUIIT-UHFFFAOYSA-N 1,2-dimethylanthracene Chemical compound C1=CC=CC2=CC3=C(C)C(C)=CC=C3C=C21 PLPFBVXTEJUIIT-UHFFFAOYSA-N 0.000 description 1
- DZNJMLVCIZGWSC-UHFFFAOYSA-N 3',6'-bis(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N(CC)CC)C=C1OC1=CC(N(CC)CC)=CC=C21 DZNJMLVCIZGWSC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
-
- 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
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
- G03C1/732—Leuco dyes
Definitions
- An exemplary composition according to that patent application contained 100 mg of Leuco Crystal Violet, 1.4 grams of CBq, and 15 mg. of '4-picoline-N-oxide, dispersed in a film of polystyrene.
- the L.E.S. of this composition approximated '5 X 10 L.E.S. stands for Light Exposure Speed and is defined as the reciprocal of the exposure, expressed in meter candle second, which is required to produce a density (diffuse transmission density) of 0.2 density units above the density o'f'base I plus fog (see Photographic Science and Engineering, Vol; 8 1964, page 98, last paragraph).
- sensitivity dyes and/or polyphenylmethane ca'rbiriol bases and/or tertiary amines enhances the sensitivity of the composition and improves the photographic speed thereof.
- These additives may be used either singly or in combination with one another to produce the enhanced photographic speeds characteristic of the present invention.
- N-vinyl carbazole may be added to increase the contrast (gamma) and maximum derisity.
- compositions hereinafter described are prepared in'the same manner as those described in the above-noted patent application and in Photographic Science and Engineering, Vol. 5, number 2, Man-April 1961, pp. 98 et seq. I
- compositions are each prepared by bringing'the constituents together in a suitable solvent-binder solution under a safelight or in total darkness, each of the constituents usually being added to the solution in the order set forth in the examples, then mixed to effect solution before addition of the'next named constituent. After thorough mixing, the composition is applied to a suitable substrate which may be barytapaper or a film of polyester, glass or other support.
- composition After the composition has been laid down as athin film, itis permitted to dry in air in the dark or under a safelight, drying here meaning the elimination of the solvent(s) from the composition by evaporation. Then the composition is photographically exposed for a time sufficient to produce at least a latent image in the composition.
- the latent image in the film is developed by exposing the entire film to radiant energy of an appropriate intensity (e.g.) 50 watt tungsten light source) and suitable wavelength (e.g. between about 600 and 900g).
- radiant energy e.g. 50 watt tungsten light source
- suitable wavelength e.g. between about 600 and 900g.
- composition of the type described in the above noted US. Patent is as follows:
- EXAMPLE 1 The addition of 6 mg. of Rhodamine B base of the above formulation produced a speed of 0.013 L.E.S., 1), of 1.32 and base plus fog 0.36. This illustrates the benefits of adding a dye to such a composition.
- EXAMPLE 2 A photographic speed of 0.04 L.E.S. with acceptable base plus fog levels was achieved by the addition of minor amounts of merocyanine dyes with or without xanthene'type dyes '(R- ho'damine B,etc.). In addition, it was found that carbinol compounds of the leuco triphenylr'nethane derivatives appear to be beneficialand increase the density 'of the image formed. The following composition produced photographic speedsof 0.04 L.E.S.:
- EXAMPLE 3 A photographic speed-of 0.1 L.E.S. with acceptable base plus fog levels was achieved by the addition of 5 mg of Crystal Violet carbinol to the formulation represented in Example 2.
- One composition producing photographic speeds of 0.1 L.E.S. was asfollows:
- EXAMPLE 4 Theaddition of a small quantity of a tertiary amine, such as EXAMPLE 5
- EXAMPLE 6 The addition of 5 mg. of N-vinylcarbazole to the formulation of Example 5 increased the maximum density to 2.0 and increased the gamma (slope of H & D plot) of the film.
- EXAMPLE 7 A substantial improvement was obtained by the increased amounts of both the leuco anthracene and carbinol of crystal violet and omitting the leuco crystal violet, as shown in the following formula:
- composition produced photographic speeds of 1.0 L.E.S., base fog 0.14, with D,,,,, rendition of 1.46.
- EXAMPLE 8 Still a further improvement in speed is attained with the following which exhibits an L.E.S. of 2.0 to 4.0, a maximum density of 1.4 and a base plus fog ofO.2:
- dimethylanthracene 5 mg. 5-[3-ethyl-2(3H)- benzoxazolylidene-ethylidene]- 3-phenyl-2phenylimino4- thiazolidinone 2 mg. 4-picoline-N-oxide l0 mg.
- Carbinol of crystal violet (stabilized*) 1.3 mg.
- Carbinol of opal blue (stabilized') 6 drops N-methyldiphenylamine solution 1.4 g. Carbon tetrabromide 4.5 cc. 10% polystyrene in benzene Stabilized by digestion with alkali I drop N-methyldiphenylamine in 5 cc.
- compositions described in the preceding examples are utilized by exposing the same to a pattern of radiation and then developing a visible image by a blanket exposure to radiation in a narrow band corresponding to that region to which the composition has been sensitized by the dye formed during the photographic exposure.
- Example 8 the amount of N-oxide hasbeen considerably diminished as compared with the amounts utilized in the earlier indicated U.S. patent, this being due in part to the use of a combination of sensitizers as described.
- the purpose of the addition of the sensitizing dye such as a merocyanine'dye is to increase the absorption of visible light so as to increase the photographic speed.
- the purpose of the addition of the polyphenylmethane carbinols is to increase the photographic speed by an increase in the quantum yield of dye, i.e., by an increase in the inherent sensitivity of the system to an absorbed photon of visible light.
- the purpose of the addition of the tertiary amine is to reduce formation of dye from the color-former by thermal reactions with atmospheric ingredients or with other ingredients of the film coating.
- a photosensitive composition comprising:
- each R is selected from the group consisting of H, alkyl with up to 4 carbon atoms and halogen substituted alkyl with up to 4 carbon atoms and each R' is selected from the group consisting of H and lower alkyl;
- said activator being at least one compound represented by the general formula AiC-X wherein A represents a monovalent radical selected from the group consisting of halogen, alkyl, substituted alkyl, including halogen substituted alkyl, aryl, substituted aryl, aroyl and aralkyl and each X represents a halogen atom selected from the group consisting of chlorine, bromine and iodine and all of the Xs need not be the same;
- N 0 compound at least one organic N 0 compound; the improvement which comprises including in said composition one or more additional compounds selected from the group consisting of merocyanine dyes, polyphenylmethane carbinol bases and N-methyl diphenyl amines whereby the photographic speed of the initial composition is increased as compared with the speed of said composition absent said additional compounds.
- N 0 compound is one represented by the general fonnula R-N 0 wherein R represents an organic moiety such that the resulting compound is an N-oxide selected from the group consisting of tertiary amines, nitrones, and di-nitrones.
- N 0 compound is one represented by the general formula wherein R represents atoms of carbon, oxygen, nitrogen or sulfur necessary to complete a 5 or 6 member ring or a fused ring.
- composition of claim 1 wherein the activator is a bromine substituted alkane.
- composition including both a leucoanthracene and a merocyanine dye according to claim 1.
- composition of claim 1 wherein there are between 0.1 and 2 parts by weight of N 0 compound for each part by weight of color forming compound.
- composition of claim 1 which includes, in addition, a film forming resin binder.
- composition of claim 1 wherein R" and R are all CH groups in the anthracene.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74600868A | 1968-07-19 | 1968-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3660096A true US3660096A (en) | 1972-05-02 |
Family
ID=24999124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US746008A Expired - Lifetime US3660096A (en) | 1968-07-19 | 1968-07-19 | Speed increasing additives for non-silver light sensitive systems |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3660096A (enrdf_load_stackoverflow) |
| JP (1) | JPS4824539B1 (enrdf_load_stackoverflow) |
| DE (1) | DE1919025A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1264193A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980706A (en) * | 1975-11-06 | 1976-09-14 | Horizons Incorporated A Division Of Horizons Research Incorporated | Synthesis of 2,7-bisdimethylamino-10-P-dimethylaminophenyl-9,10-dihydro-9,9-dimethylanthracene |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52164926U (enrdf_load_stackoverflow) * | 1976-06-09 | 1977-12-14 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3503745A (en) * | 1963-05-06 | 1970-03-31 | Bell & Howell Co | Dye sensitization of light sensitive systems |
-
1968
- 1968-07-19 US US746008A patent/US3660096A/en not_active Expired - Lifetime
-
1969
- 1969-04-15 DE DE19691919025 patent/DE1919025A1/de active Pending
- 1969-04-15 GB GB1264193D patent/GB1264193A/en not_active Expired
- 1969-04-18 JP JP44029709A patent/JPS4824539B1/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3503745A (en) * | 1963-05-06 | 1970-03-31 | Bell & Howell Co | Dye sensitization of light sensitive systems |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980706A (en) * | 1975-11-06 | 1976-09-14 | Horizons Incorporated A Division Of Horizons Research Incorporated | Synthesis of 2,7-bisdimethylamino-10-P-dimethylaminophenyl-9,10-dihydro-9,9-dimethylanthracene |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1264193A (enrdf_load_stackoverflow) | 1972-02-16 |
| JPS4824539B1 (enrdf_load_stackoverflow) | 1973-07-21 |
| DE1919025A1 (de) | 1970-01-22 |
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