CA1046330A - Photoconductive composition and elements with a styryl amino group containing photoconductor - Google Patents
Photoconductive composition and elements with a styryl amino group containing photoconductorInfo
- Publication number
- CA1046330A CA1046330A CA197,318A CA197318A CA1046330A CA 1046330 A CA1046330 A CA 1046330A CA 197318 A CA197318 A CA 197318A CA 1046330 A CA1046330 A CA 1046330A
- Authority
- CA
- Canada
- Prior art keywords
- photoconductive
- tolylamino
- radical
- alkyl
- composition
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 125000005504 styryl group Chemical group 0.000 title claims 9
- 125000003277 amino group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- -1 alkyl radical Chemical class 0.000 claims description 136
- 238000000034 method Methods 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 21
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 229910000464 lead oxide Inorganic materials 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 6
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 6
- 235000021286 stilbenes Nutrition 0.000 claims 6
- CMYGZXUTDIOAOV-UHFFFAOYSA-N 4-methyl-n-[4-[2-[10-[2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]anthracen-9-yl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C=CC=2C3=CC=CC=C3C(C=CC=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=C3C=CC=CC3=2)=CC=1)C1=CC=C(C)C=C1 CMYGZXUTDIOAOV-UHFFFAOYSA-N 0.000 claims 1
- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 claims 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract description 3
- 239000011593 sulfur Substances 0.000 abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 41
- 239000010410 layer Substances 0.000 description 30
- 239000000975 dye Substances 0.000 description 25
- 238000009740 moulding (composite fabrication) Methods 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 15
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 14
- 231100000489 sensitizer Toxicity 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 231100000202 sensitizing Toxicity 0.000 description 11
- 230000001235 sensitizing effect Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 9
- 150000001491 aromatic compounds Chemical class 0.000 description 8
- 239000008199 coating composition Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 239000004020 conductor Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 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 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 239000000298 carbocyanine Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 208000013469 light sensitivity Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 230000000153 supplemental effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UKXDHEBARGMWMO-ARJAWSKDSA-N (z)-4-(2-methylpropoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)COC(=O)\C=C/C(O)=O UKXDHEBARGMWMO-ARJAWSKDSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical group C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- TZIVKFFJHJSKID-UHFFFAOYSA-N 1,5-bis(diethoxyphosphorylmethyl)-2,4-dimethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC(CP(=O)(OCC)OCC)=C(C)C=C1C TZIVKFFJHJSKID-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- XCGLXUJEPIVZJM-UHFFFAOYSA-N 4-(4-methyl-n-(4-methylphenyl)anilino)benzaldehyde Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C=O)=CC=1)C1=CC=C(C)C=C1 XCGLXUJEPIVZJM-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- XKACUVXWRVMXOE-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C)C1=CC=C(C(O)=O)C=C1 XKACUVXWRVMXOE-UHFFFAOYSA-N 0.000 description 1
- YXYUIABODWXVIK-UHFFFAOYSA-N 4-methyl-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 YXYUIABODWXVIK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 229940122361 Bisphosphonate Drugs 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
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- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
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- 239000000025 natural resin Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- NTQLADLBRQMNQJ-UHFFFAOYSA-M pyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=[O+]C=C1 NTQLADLBRQMNQJ-UHFFFAOYSA-M 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
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- 239000011550 stock solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
- G03G5/087—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic and being incorporated in an organic bonding material
-
- 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
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
-
- 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
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
- G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings
-
- 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
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/07—Polymeric photoconductive materials
-
- 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
- G03G5/09—Sensitisors or activators, e.g. dyestuffs
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35744173A | 1973-05-04 | 1973-05-04 | |
| US443657A US3873312A (en) | 1973-05-04 | 1974-02-19 | Photoconductive composition and elements containing a styryl amino group containing photoconductor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1046330A true CA1046330A (en) | 1979-01-16 |
Family
ID=26999657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA197,318A Expired CA1046330A (en) | 1973-05-04 | 1974-04-10 | Photoconductive composition and elements with a styryl amino group containing photoconductor |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3873312A (enExample) |
| JP (1) | JPS5857739B2 (enExample) |
| AU (1) | AU6854974A (enExample) |
| BE (1) | BE814571A (enExample) |
| CA (1) | CA1046330A (enExample) |
| CH (1) | CH589877A5 (enExample) |
| FR (1) | FR2228243B1 (enExample) |
| GB (1) | GB1465142A (enExample) |
| IT (1) | IT1010451B (enExample) |
| NL (1) | NL7406027A (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2364396A1 (de) * | 1973-12-22 | 1975-07-10 | Basf Ag | Neue bisstyrylarylverbindungen |
| CA1086410A (en) * | 1977-08-02 | 1980-09-23 | Ching W. Tang | Organic photovoltaic elements |
| JPS5799648A (en) | 1980-12-13 | 1982-06-21 | Copyer Co Ltd | Electrophotographic receptor |
| US4423129A (en) | 1980-12-17 | 1983-12-27 | Canon Kabushiki Kaisha | Electrophotographic member having layer containing methylidenyl hydrazone compound |
| US4446217A (en) * | 1981-02-03 | 1984-05-01 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member having a hydrazone containing layer |
| US4418133A (en) | 1981-03-27 | 1983-11-29 | Canon Kabushiki Kaisha | Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer |
| JPS57195255A (en) | 1981-05-26 | 1982-11-30 | Canon Inc | Electrophotographic receptor |
| US4427753A (en) | 1981-06-02 | 1984-01-24 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member with disazo or trisazo compound |
| US4456671A (en) * | 1981-12-23 | 1984-06-26 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound |
| DE3347905C2 (enExample) * | 1982-04-30 | 1992-03-12 | Ricoh Co., Ltd., Tokio/Tokyo, Jp | |
| JPS58199353A (ja) * | 1982-05-17 | 1983-11-19 | Canon Inc | 電子写真感光体 |
| JPS5931964A (ja) * | 1982-08-16 | 1984-02-21 | Fuji Photo Film Co Ltd | 電子写真感光体 |
| US4423203A (en) * | 1982-08-20 | 1983-12-27 | Eastman Kodak Company | Electrically photosensitive polymers containing vinylene-1,4-phenylene-imino-1,4-phenylene-vinylenearylene groups |
| JPS59191060A (ja) * | 1983-04-14 | 1984-10-30 | Ricoh Co Ltd | 電子写真用感光体 |
| JPS6236674A (ja) * | 1985-08-05 | 1987-02-17 | Fuji Photo Film Co Ltd | 電子写真感光体 |
| JPH0693124B2 (ja) * | 1986-05-12 | 1994-11-16 | ミノルタ株式会社 | 感光体 |
| JP2552695B2 (ja) * | 1987-04-21 | 1996-11-13 | 株式会社リコー | ジオレフィン芳香族化合物 |
| DE3813459A1 (de) * | 1987-04-24 | 1988-11-10 | Minolta Camera Kk | Funktionsmaessig geteiltes photoempfindliches element |
| DE3814105C2 (de) * | 1987-04-27 | 1999-02-04 | Minolta Camera Kk | Elektrophotographisches Aufzeichnungsmaterial |
| US4900645A (en) * | 1987-04-27 | 1990-02-13 | Minolta Camera Kabushiki Kaisha | Electrophotographic photosensitive member comprises styryl compound as transport material |
| JP2595531B2 (ja) * | 1987-04-27 | 1997-04-02 | ミノルタ株式会社 | 感光体 |
| US4886720A (en) * | 1987-08-31 | 1989-12-12 | Minolta Camera Kabushiki Kaisha | Photosensitive medium having a styryl charge transport material |
| JP2520452B2 (ja) * | 1988-06-30 | 1996-07-31 | 三菱製紙株式会社 | 電子写真感光体 |
| JP3272257B2 (ja) * | 1997-02-26 | 2002-04-08 | 京セラミタ株式会社 | 電子写真感光体 |
| US6022998A (en) * | 1997-07-24 | 2000-02-08 | Mita Industrial Co., Ltd. | Stilbene derivative and method for producing the same |
| JP3646012B2 (ja) | 1998-10-29 | 2005-05-11 | 京セラミタ株式会社 | 電子写真感光体 |
| JP3568431B2 (ja) | 1999-09-29 | 2004-09-22 | 京セラミタ株式会社 | スチルベン誘導体、その製造方法およびそれを用いた電子写真感光体 |
| EP1542083B1 (en) * | 2002-07-23 | 2006-10-04 | Osaka Gas Co., Ltd. | Electrophotographic photoreceptor and electrophoto- graphic apparatus equipped with the same |
| JP4082586B2 (ja) * | 2003-02-18 | 2008-04-30 | 高砂香料工業株式会社 | 電子写真感光体 |
| US7381511B2 (en) * | 2003-06-02 | 2008-06-03 | Ricoh Company, Ltd. | Photoreceptor, image forming method and image forming apparatus using the photoreceptor, process cartridge using the photoreceptor and coating liquid for the photoreceptor |
| KR100750163B1 (ko) * | 2006-02-16 | 2007-08-21 | 삼성전자주식회사 | 고감도이고 반복대전 안정성이 우수한 전자사진 감광체 및이를 채용한 전자사진 화상형성장치 |
| US20070212626A1 (en) * | 2006-03-10 | 2007-09-13 | Tetsuya Toshine | Electrophotographic photoreceptor, and image forming apparatus and process cartridge using the same |
| US20090185821A1 (en) * | 2008-01-10 | 2009-07-23 | Ricoh Company, Ltd | Electrophotographic photoreceptor, and image formihg appratus and process cartridge using same |
| JP5402279B2 (ja) * | 2008-06-27 | 2014-01-29 | 株式会社リコー | 電子写真感光体、その製造方法、及びそれを使用した画像形成装置 |
| US8173343B2 (en) * | 2008-07-15 | 2012-05-08 | Ricoh Company, Ltd. | Electrophotographic photoconductor, image forming apparatus using the same, and process cartridge |
| CN102471263A (zh) | 2009-07-28 | 2012-05-23 | 保土谷化学工业株式会社 | 吲哚衍生物 |
| JP5753788B2 (ja) | 2009-11-06 | 2015-07-22 | 保土谷化学工業株式会社 | ジフェニルナフチルアミン誘導体 |
| JPWO2012002227A1 (ja) | 2010-06-29 | 2013-08-22 | 保土谷化学工業株式会社 | トリフェニルアミン誘導体 |
| JP6095107B2 (ja) | 2013-01-29 | 2017-03-15 | 高砂香料工業株式会社 | トリフェニルアミン誘導体、並びにそれを用いた電荷輸送材料及び電子写真感光体 |
| US10795272B2 (en) | 2016-02-08 | 2020-10-06 | Takasago International Corporation | Triphenylamine derivative, and charge transport material and electrophotographic photoreceptor using the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE558078A (enExample) * | 1956-06-04 | |||
| BE589373A (enExample) * | 1959-04-08 | |||
| US3085935A (en) * | 1961-04-24 | 1963-04-16 | Burroughs Wellcome Co | Method for the elimination of nematode infestations |
| BE617032A (enExample) * | 1961-04-29 | |||
| US3615415A (en) * | 1966-10-14 | 1971-10-26 | Eastman Kodak Co | Method for the preparation of photoconductive compositions |
| CH508692A (de) * | 1968-01-15 | 1971-06-15 | Ciba Geigy Ag | Verwendung von Styryl-naphthalin-Derivaten als optische Aufhellmittel ausserhalb der Textilindustrie |
| US3615414A (en) * | 1969-03-04 | 1971-10-26 | Eastman Kodak Co | Photoconductive compositions and elements and method of preparation |
| US3615396A (en) * | 1969-04-16 | 1971-10-26 | Eastman Kodak Co | Method for the preparation of multiphase heterogeneous photoconductive compositions containing at least one pyrylium dye and an electrically insulating polymer |
| BE758335A (fr) * | 1969-11-04 | 1971-04-01 | Eastman Kodak Co | Nouveaux composes photoconducteurs utilisables dans des produits electrophotographiques |
| CH540958A (de) * | 1970-07-23 | 1973-08-31 | Ciba Geigy Ag | Verwendung von Styrylverbindungen als optische Aufhellmittel für organische Materialien ausserhalb der Textilindustrie |
-
1974
- 1974-02-19 US US443657A patent/US3873312A/en not_active Expired - Lifetime
- 1974-04-10 CA CA197,318A patent/CA1046330A/en not_active Expired
- 1974-05-03 CH CH607074A patent/CH589877A5/xx not_active IP Right Cessation
- 1974-05-03 GB GB1959174A patent/GB1465142A/en not_active Expired
- 1974-05-03 BE BE143943A patent/BE814571A/xx unknown
- 1974-05-03 NL NL7406027A patent/NL7406027A/xx unknown
- 1974-05-03 AU AU68549/74A patent/AU6854974A/en not_active Expired
- 1974-05-04 JP JP49050203A patent/JPS5857739B2/ja not_active Expired
- 1974-05-06 IT IT22343/74A patent/IT1010451B/it active
- 1974-05-06 FR FR7415498A patent/FR2228243B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2421502B2 (de) | 1976-07-29 |
| IT1010451B (it) | 1977-01-10 |
| CH589877A5 (enExample) | 1977-07-15 |
| JPS5857739B2 (ja) | 1983-12-21 |
| GB1465142A (en) | 1977-02-23 |
| US3873312A (en) | 1975-03-25 |
| FR2228243B1 (enExample) | 1977-06-24 |
| AU6854974A (en) | 1975-11-06 |
| DE2421502A1 (de) | 1974-11-14 |
| FR2228243A1 (enExample) | 1974-11-29 |
| BE814571A (fr) | 1974-11-04 |
| JPS5031773A (enExample) | 1975-03-28 |
| NL7406027A (enExample) | 1974-11-06 |
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