CA1119449A - Photosensitive material containing an organic polymeric photoconductor, phthalocyanine derivative and an electron acceptor polycyclic aromatic nitro compound - Google Patents
Photosensitive material containing an organic polymeric photoconductor, phthalocyanine derivative and an electron acceptor polycyclic aromatic nitro compoundInfo
- Publication number
- CA1119449A CA1119449A CA000295001A CA295001A CA1119449A CA 1119449 A CA1119449 A CA 1119449A CA 000295001 A CA000295001 A CA 000295001A CA 295001 A CA295001 A CA 295001A CA 1119449 A CA1119449 A CA 1119449A
- Authority
- CA
- Canada
- Prior art keywords
- photosensitive material
- phthalocyanine
- nitro compound
- polycyclic aromatic
- aromatic nitro
- 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
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000000463 material Substances 0.000 title claims abstract description 45
- -1 aromatic nitro compound Chemical class 0.000 title claims abstract description 31
- 125000003367 polycyclic group Chemical group 0.000 title description 10
- 239000011230 binding agent Substances 0.000 claims abstract description 22
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 239000004925 Acrylic resin Substances 0.000 claims description 9
- 229920000178 Acrylic resin Polymers 0.000 claims description 9
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 5
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 24
- 238000012546 transfer Methods 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 5
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000008199 coating composition Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000002828 nitro derivatives Chemical class 0.000 description 7
- 229920002545 silicone oil Polymers 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000000630 rising effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 229940117958 vinyl acetate Drugs 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [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 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- SXNLZNGQJWKPAM-UHFFFAOYSA-N 2,9,16,23-tetraphenyl-29h,31h-phthalocyanine Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C3NC(C4=CC=C(C=C43)C=3C=CC=CC=3)=NC=3NC([C]4C=CC(=CC4=3)C=3C=CC=CC=3)=NC=3N=C([C]4C=CC(=CC4=3)C=3C=CC=CC=3)N=C3N=2)C3=C1 SXNLZNGQJWKPAM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101150039033 Eci2 gene Proteins 0.000 description 2
- 102000006835 Lamins Human genes 0.000 description 2
- 108010047294 Lamins Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241000282337 Nasua nasua Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
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- 230000035945 sensitivity Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SKKUAUZTZZRYPW-UHFFFAOYSA-N 1-chloro-2,4-dinitronaphthalene Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CC([N+]([O-])=O)=C21 SKKUAUZTZZRYPW-UHFFFAOYSA-N 0.000 description 1
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- XFLONXIGNOXKCG-UHFFFAOYSA-N 2,7-dinitroanthracene-9,10-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 XFLONXIGNOXKCG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 1
- AEPGKFYDDKSQBC-UHFFFAOYSA-N 9-butyl-3-nitrocarbazole Chemical compound [O-][N+](=O)C1=CC=C2N(CCCC)C3=CC=CC=C3C2=C1 AEPGKFYDDKSQBC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
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- 229910052776 Thorium Inorganic materials 0.000 description 1
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- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- ROJMAHHOFDIQTI-UHFFFAOYSA-L calcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;hydron;piperazine Chemical compound [Ca+2].C1CNCCN1.OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ROJMAHHOFDIQTI-UHFFFAOYSA-L 0.000 description 1
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- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
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- 238000009713 electroplating Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
- G03G5/047—Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport layers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP292277A JPS5389433A (en) | 1977-01-17 | 1977-01-17 | Photosensitive body for electrophotography |
| JP2922/77 | 1977-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1119449A true CA1119449A (en) | 1982-03-09 |
Family
ID=11542830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000295001A Expired CA1119449A (en) | 1977-01-17 | 1978-01-16 | Photosensitive material containing an organic polymeric photoconductor, phthalocyanine derivative and an electron acceptor polycyclic aromatic nitro compound |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5389433A (en, 2012) |
| CA (1) | CA1119449A (en, 2012) |
| DE (1) | DE2801914C2 (en, 2012) |
| FR (1) | FR2377655B1 (en, 2012) |
| GB (1) | GB1570576A (en, 2012) |
| IT (1) | IT1092743B (en, 2012) |
| NL (1) | NL7800575A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8951702B2 (en) | 2008-07-18 | 2015-02-10 | Fuji Electric Co., Ltd. | Charge transport material that is an ethylene compound, electrophotographic photoreceptor containing the charge transport material, and process for producing the electrophotographic photoreceptor |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5424026A (en) * | 1977-07-26 | 1979-02-23 | Mita Industrial Co Ltd | Photoconductive composition for electrophotography |
| JPS61123848A (ja) * | 1984-11-21 | 1986-06-11 | Canon Inc | 電子写真感光体 |
| JP2003015334A (ja) | 2001-04-27 | 2003-01-17 | Fuji Denki Gazo Device Kk | 電子写真用感光体およびその製造方法 |
| JP2007108474A (ja) | 2005-10-14 | 2007-04-26 | Fuji Electric Device Technology Co Ltd | 電子写真用感光体 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3672979A (en) * | 1970-01-02 | 1972-06-27 | Xerox Corp | Method of producing a phthalocyanine photoconductive layer |
| FR2095660A5 (en) * | 1970-06-01 | 1972-02-11 | Eastman Kodak Co | Electrophotographic composition of high sensitivity |
| NL7302762A (en, 2012) * | 1972-02-29 | 1973-08-31 | ||
| US3903107A (en) * | 1973-06-04 | 1975-09-02 | Xerox Corp | Direct alpha to X phase conversion of metal containing phthalocyanine |
-
1977
- 1977-01-17 JP JP292277A patent/JPS5389433A/ja active Granted
-
1978
- 1978-01-16 GB GB1714/78A patent/GB1570576A/en not_active Expired
- 1978-01-16 CA CA000295001A patent/CA1119449A/en not_active Expired
- 1978-01-17 NL NL7800575A patent/NL7800575A/xx not_active Application Discontinuation
- 1978-01-17 FR FR7801206A patent/FR2377655B1/fr not_active Expired
- 1978-01-17 IT IT19314/78A patent/IT1092743B/it active
- 1978-01-17 DE DE2801914A patent/DE2801914C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8951702B2 (en) | 2008-07-18 | 2015-02-10 | Fuji Electric Co., Ltd. | Charge transport material that is an ethylene compound, electrophotographic photoreceptor containing the charge transport material, and process for producing the electrophotographic photoreceptor |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1570576A (en) | 1980-07-02 |
| JPS6148149B2 (en, 2012) | 1986-10-22 |
| NL7800575A (nl) | 1978-07-19 |
| FR2377655B1 (en, 2012) | 1984-03-23 |
| IT1092743B (it) | 1985-07-12 |
| DE2801914A1 (de) | 1978-07-27 |
| IT7819314A0 (it) | 1978-01-17 |
| FR2377655A1 (en, 2012) | 1978-08-11 |
| DE2801914C2 (de) | 1985-02-28 |
| JPS5389433A (en) | 1978-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |