JPS6248220B2

JPS6248220B2 -

Info

Publication number: JPS6248220B2
Authority: JP; Japan
Prior art keywords: bis; dimethylaminophenyl; phenyl; divinylylene; carbonium
Prior art date: 1978-12-27
Legal status : Expired

Application number

JP16309478A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5588066A (en

Inventor

Kazuhiro Enomoto

Kyoshi Futaki

Current Assignee

Mitsubishi Paper Mills Ltd

Original Assignee

Mitsubishi Paper Mills Ltd

Priority date

1978-12-27

Filing date

1978-12-27

Publication date

1987-10-13

1978-12-27 Application filed by Mitsubishi Paper Mills Ltd filed Critical Mitsubishi Paper Mills Ltd

1978-12-27 Priority to JP16309478A priority Critical patent/JPS5588066A/ja

1980-07-03 Publication of JPS5588066A publication Critical patent/JPS5588066A/ja

1982-03-04 Priority to US06/354,609 priority patent/US4387149A/en

1987-10-13 Publication of JPS6248220B2 publication Critical patent/JPS6248220B2/ja

Status Granted legal-status Critical Current

Links

-1 -OR 5 Inorganic materials 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000005504 styryl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000001450 anions Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000000975 dye Substances 0.000 description 34
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 22
150000001875 compounds Chemical class 0.000 description 15
230000001235 sensitizing effect Effects 0.000 description 15
238000000034 method Methods 0.000 description 12
206010070834 Sensitisation Diseases 0.000 description 10
108091008695 photoreceptors Proteins 0.000 description 10
230000008313 sensitization Effects 0.000 description 10
230000035945 sensitivity Effects 0.000 description 9
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000001294 propane Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
206010034972 Photosensitivity reaction Diseases 0.000 description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000001273 butane Substances 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
230000036211 photosensitivity Effects 0.000 description 3
239000004431 polycarbonate resin Substances 0.000 description 3
229920005668 polycarbonate resin Polymers 0.000 description 3
238000011282 treatment Methods 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
229920002799 BoPET Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000004420 Iupilon Substances 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000008199 coating composition Substances 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IDAQSADEMXDTKN-UHFFFAOYSA-L ethyl green Chemical compound [Cl-].[Br-].C1=CC([N+](C)(C)CC)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C1C=CC(=[N+](C)C)C=C1 IDAQSADEMXDTKN-UHFFFAOYSA-L 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229940018564 m-phenylenediamine Drugs 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
IIQGJRFXBVRJIU-UHFFFAOYSA-M (4-chromen-2-ylidenecyclohexa-2,5-dien-1-ylidene)-dimethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(=[N+](C)C)C=CC1=C1C=CC2=CC=CC=C2O1 IIQGJRFXBVRJIU-UHFFFAOYSA-M 0.000 description 1
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OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
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QAHMKHHCOXNIHO-UHFFFAOYSA-N 2,4-diphenylquinazoline Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QAHMKHHCOXNIHO-UHFFFAOYSA-N 0.000 description 1
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OMXSHNIXAVHELO-UHFFFAOYSA-N 2-phenyl-4-(2-phenylethenyl)quinazoline Chemical compound C=1C=CC=CC=1C=CC(C1=CC=CC=C1N=1)=NC=1C1=CC=CC=C1 OMXSHNIXAVHELO-UHFFFAOYSA-N 0.000 description 1
PLXDMYDTNAAJKU-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-oxo-n-phenylpropanamide Chemical compound ClC1=CC=CC(C(=O)CC(=O)NC=2C=CC=CC=2)=C1 PLXDMYDTNAAJKU-UHFFFAOYSA-N 0.000 description 1
ZTXMSSUWNYFDCH-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-phenyl-1-benzofuran-6-ol Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C=2C=CC=CC=2)OC2=CC(O)=CC=C12 ZTXMSSUWNYFDCH-UHFFFAOYSA-N 0.000 description 1
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JHKQSICMMKJIAA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;lead Chemical compound [Pb].C1=CC=C2SC(=S)NC2=C1 JHKQSICMMKJIAA-UHFFFAOYSA-N 0.000 description 1
OFQGIIIVIXXLRO-UHFFFAOYSA-N 3h-1,3-benzoxazole-2-thione;lead Chemical compound [Pb].C1=CC=C2OC(=S)NC2=C1 OFQGIIIVIXXLRO-UHFFFAOYSA-N 0.000 description 1
UECMVEOOXQNVNB-UHFFFAOYSA-N 4-(2,5-diphenyl-1,3-dihydropyrazol-3-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1N(C=2C=CC=CC=2)NC(C=2C=CC=CC=2)=C1 UECMVEOOXQNVNB-UHFFFAOYSA-N 0.000 description 1
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