CA1046265A - Electrophotography photosensitive composition - Google Patents
Electrophotography photosensitive compositionInfo
- Publication number
- CA1046265A CA1046265A CA224,836A CA224836A CA1046265A CA 1046265 A CA1046265 A CA 1046265A CA 224836 A CA224836 A CA 224836A CA 1046265 A CA1046265 A CA 1046265A
- Authority
- CA
- Canada
- Prior art keywords
- malononitrile
- cyano
- beta
- alpha
- group
- 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 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 17
- -1 chrycene Chemical compound 0.000 claims description 13
- UUKLIKUNCGVVHN-UHFFFAOYSA-N 2-[(4-cyanophenyl)methylidene]propanedinitrile Chemical compound N#CC(C#N)=CC1=CC=C(C#N)C=C1 UUKLIKUNCGVVHN-UHFFFAOYSA-N 0.000 claims description 11
- GGIHYGVNLFPXSY-UHFFFAOYSA-N 2-[(2-chloro-5-nitrophenyl)methylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=C(C#N)C#N)=C1 GGIHYGVNLFPXSY-UHFFFAOYSA-N 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- UETSUBDMYFNYDL-UHFFFAOYSA-N 2-(naphthalen-2-ylmethylidene)propanedinitrile Chemical compound C1=CC=CC2=CC(C=C(C#N)C#N)=CC=C21 UETSUBDMYFNYDL-UHFFFAOYSA-N 0.000 claims description 7
- CRUJHLHRJSNZIU-UHFFFAOYSA-N 2-(furan-2-ylmethylidene)propanedinitrile Chemical compound N#CC(C#N)=CC1=CC=CO1 CRUJHLHRJSNZIU-UHFFFAOYSA-N 0.000 claims description 6
- BDTIGNGBIBFXSE-UHFFFAOYSA-N 2-[(4-nitrophenyl)methylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C(C=C(C#N)C#N)C=C1 BDTIGNGBIBFXSE-UHFFFAOYSA-N 0.000 claims description 6
- WAVNYPVYNSIHNC-UHFFFAOYSA-N 2-benzylidenepropanedinitrile Chemical group N#CC(C#N)=CC1=CC=CC=C1 WAVNYPVYNSIHNC-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- BQOCYDLOAKZPQE-QPJJXVBHSA-N 2-[(e)-3-phenylprop-2-enylidene]propanedinitrile Chemical compound N#CC(C#N)=C\C=C\C1=CC=CC=C1 BQOCYDLOAKZPQE-QPJJXVBHSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- FBOCHORMPUIPSN-UHFFFAOYSA-N methyl 4-(2,2-dicyanoethenyl)benzoate Chemical compound COC(=O)C1=CC=C(C=C(C#N)C#N)C=C1 FBOCHORMPUIPSN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- XNGKCOFXDHYSGR-UHFFFAOYSA-N perillene Chemical compound CC(C)=CCCC=1C=COC=1 XNGKCOFXDHYSGR-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- RDMANBWYQHJIFZ-UHFFFAOYSA-N 2-(anthracen-9-ylmethylidene)propanedinitrile Chemical compound C1=CC=C2C(C=C(C#N)C#N)=C(C=CC=C3)C3=CC2=C1 RDMANBWYQHJIFZ-UHFFFAOYSA-N 0.000 claims description 3
- RRVZSQGJZJMCAE-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methylidene]propanedinitrile Chemical compound ClC1=CC=C(C=C(C#N)C#N)C(Cl)=C1 RRVZSQGJZJMCAE-UHFFFAOYSA-N 0.000 claims description 3
- UQMJZLGIKHAOQZ-UHFFFAOYSA-N 2-[(3-nitrophenyl)methylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=CC(C=C(C#N)C#N)=C1 UQMJZLGIKHAOQZ-UHFFFAOYSA-N 0.000 claims description 3
- FQSXBLOWLYPURG-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]propanedinitrile Chemical compound ClC1=CC=C(C=C(C#N)C#N)C=C1 FQSXBLOWLYPURG-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- QPMLLJYCAKQATA-UHFFFAOYSA-N 2,3-bis(4-nitrophenyl)prop-2-enenitrile Chemical group C1=CC([N+](=O)[O-])=CC=C1C=C(C#N)C1=CC=C([N+]([O-])=O)C=C1 QPMLLJYCAKQATA-UHFFFAOYSA-N 0.000 claims description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
- GTMWKXFXKLPJPU-UHFFFAOYSA-N 2-(1,2-dihydroacenaphthylen-5-ylmethylidene)propanedinitrile Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C=C(C#N)C#N GTMWKXFXKLPJPU-UHFFFAOYSA-N 0.000 claims description 2
- VABTYALPMVDJSR-UHFFFAOYSA-N 2-(thiophen-2-ylmethylidene)propanedinitrile Chemical compound N#CC(C#N)=CC1=CC=CS1 VABTYALPMVDJSR-UHFFFAOYSA-N 0.000 claims description 2
- KLJAZYOWHGTDAA-UHFFFAOYSA-N 2-[(3-cyanophenyl)methylidene]propanedinitrile Chemical compound N#CC(C#N)=CC1=CC=CC(C#N)=C1 KLJAZYOWHGTDAA-UHFFFAOYSA-N 0.000 claims description 2
- MYMFYWGVTXOLRG-UHFFFAOYSA-N 2-[(4-bromophenyl)methylidene]propanedinitrile Chemical compound BrC1=CC=C(C=C(C#N)C#N)C=C1 MYMFYWGVTXOLRG-UHFFFAOYSA-N 0.000 claims description 2
- JIFVPBALUHDGEP-UHFFFAOYSA-N 2-[(4-methylphenyl)methylidene]propanedinitrile Chemical compound CC1=CC=C(C=C(C#N)C#N)C=C1 JIFVPBALUHDGEP-UHFFFAOYSA-N 0.000 claims description 2
- WXXTURWZZJSFKU-UHFFFAOYSA-N 2-[(5-nitrothiophen-2-yl)methylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C(C=C(C#N)C#N)S1 WXXTURWZZJSFKU-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- UOHFCPXBKJPCAD-UHFFFAOYSA-N tyrphostin 1 Chemical compound COC1=CC=C(C=C(C#N)C#N)C=C1 UOHFCPXBKJPCAD-UHFFFAOYSA-N 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- CDUQMGQIHYISOP-RMKNXTFCSA-N (e)-2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=CC=C1 CDUQMGQIHYISOP-RMKNXTFCSA-N 0.000 claims 1
- HNVAUTUJXUMGPH-UHFFFAOYSA-N 2-(naphthalen-1-ylmethylidene)propanedinitrile Chemical compound C1=CC=C2C(C=C(C#N)C#N)=CC=CC2=C1 HNVAUTUJXUMGPH-UHFFFAOYSA-N 0.000 claims 1
- JVBPKACNQGCPNB-UHFFFAOYSA-N 2-[(5-nitrofuran-2-yl)methylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C(C=C(C#N)C#N)O1 JVBPKACNQGCPNB-UHFFFAOYSA-N 0.000 claims 1
- FIQHDYSKLBVYKP-UHFFFAOYSA-N 4-[2-cyano-2-(4-cyanophenyl)ethenyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(C#N)=CC1=CC=C(C#N)C=C1 FIQHDYSKLBVYKP-UHFFFAOYSA-N 0.000 claims 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims 1
- 231100000489 sensitizer Toxicity 0.000 description 28
- 230000035945 sensitivity Effects 0.000 description 20
- 239000000243 solution Substances 0.000 description 15
- 238000012546 transfer Methods 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 10
- 238000002265 electronic spectrum Methods 0.000 description 8
- 230000003993 interaction Effects 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 206010013710 Drug interaction Diseases 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 230000001235 sensitizing effect Effects 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- NMTPJXUPURJHLB-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)prop-2-enylidene]propanedinitrile Chemical compound N#CC(C#N)=CC=CC1=CC=C(C#N)C=C1 NMTPJXUPURJHLB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005488 sandblasting Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PXNJGLAVKOXITN-UHFFFAOYSA-N 2-(4-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(CC#N)C=C1 PXNJGLAVKOXITN-UHFFFAOYSA-N 0.000 description 1
- SUUDBEARADVQJK-UHFFFAOYSA-N 2-[3-(3-nitrophenyl)prop-2-enylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=CC(C=CC=C(C#N)C#N)=C1 SUUDBEARADVQJK-UHFFFAOYSA-N 0.000 description 1
- UBSQTZVPBHBOBW-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)prop-2-enylidene]propanedinitrile Chemical compound ClC1=CC=C(C=CC=C(C#N)C#N)C=C1 UBSQTZVPBHBOBW-UHFFFAOYSA-N 0.000 description 1
- UKQFDVVUFPXOGV-UHFFFAOYSA-N 2-[3-(4-nitrophenyl)prop-2-enylidene]propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C(C=CC=C(C#N)C#N)C=C1 UKQFDVVUFPXOGV-UHFFFAOYSA-N 0.000 description 1
- WSCWPJNYTYPDJY-UHFFFAOYSA-N 2-fluoropropanedinitrile Chemical compound N#CC(F)C#N WSCWPJNYTYPDJY-UHFFFAOYSA-N 0.000 description 1
- HFSLXALJYBANFV-UHFFFAOYSA-N 2-hydroxy-3-[(4-methoxyphenyl)methylidene]butanedinitrile Chemical compound COC1=CC=C(C=C(C(C#N)O)C#N)C=C1 HFSLXALJYBANFV-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- VAJIZAPXBKMPRO-UHFFFAOYSA-N 9-(oxiran-2-ylmethyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC1CO1 VAJIZAPXBKMPRO-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YFUZLOBPZJYAHQ-UHFFFAOYSA-N [4-(2,2-dicyanoethenyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C=C(C#N)C#N)C=C1 YFUZLOBPZJYAHQ-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- WVCXSPJPERKPJS-UHFFFAOYSA-L azane;dichloropalladium;hydrate Chemical compound N.N.N.N.O.Cl[Pd]Cl WVCXSPJPERKPJS-UHFFFAOYSA-L 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- G03G5/06—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
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
-
- 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
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4369574A JPS5342418B2 (en, 2012) | 1974-04-18 | 1974-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1046265A true CA1046265A (en) | 1979-01-16 |
Family
ID=12670954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,836A Expired CA1046265A (en) | 1974-04-18 | 1975-04-17 | Electrophotography photosensitive composition |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5342418B2 (en, 2012) |
| CA (1) | CA1046265A (en, 2012) |
| DE (1) | DE2517150C2 (en, 2012) |
| FR (1) | FR2268288B1 (en, 2012) |
| GB (1) | GB1490765A (en, 2012) |
| NL (1) | NL179687C (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS587643A (ja) * | 1981-07-07 | 1983-01-17 | Mitsubishi Chem Ind Ltd | 電子写真感光体 |
| JPS597956A (ja) * | 1982-07-06 | 1984-01-17 | Canon Inc | 電子写真感光体 |
| JPH05148214A (ja) * | 1991-08-30 | 1993-06-15 | Ricoh Co Ltd | α−シアノスチルベン化合物、及びそれを含有する電子写真感光体 |
| US5350653A (en) * | 1992-03-02 | 1994-09-27 | Ricoh Company, Ltd. | Electrophotographic photoconductor |
| JP6753280B2 (ja) | 2016-11-24 | 2020-09-09 | コニカミノルタ株式会社 | 電子写真感光体 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE149748C (en, 2012) * | ||||
| NL267571A (en, 2012) * | 1959-05-29 |
-
1974
- 1974-04-18 JP JP4369574A patent/JPS5342418B2/ja not_active Expired
-
1975
- 1975-04-03 NL NL7503944A patent/NL179687C/xx not_active IP Right Cessation
- 1975-04-14 FR FR7511519A patent/FR2268288B1/fr not_active Expired
- 1975-04-17 CA CA224,836A patent/CA1046265A/en not_active Expired
- 1975-04-18 DE DE19752517150 patent/DE2517150C2/de not_active Expired
- 1975-04-18 GB GB1614275A patent/GB1490765A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2517150C2 (de) | 1984-12-06 |
| AU8030675A (en) | 1976-10-21 |
| FR2268288A1 (en, 2012) | 1975-11-14 |
| NL7503944A (nl) | 1975-10-21 |
| JPS50137543A (en, 2012) | 1975-10-31 |
| GB1490765A (en) | 1977-11-02 |
| NL179687C (nl) | 1986-10-16 |
| FR2268288B1 (en, 2012) | 1981-08-21 |
| JPS5342418B2 (en, 2012) | 1978-11-11 |
| NL179687B (nl) | 1986-05-16 |
| DE2517150A1 (de) | 1975-10-30 |
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