JPH0583588B2 - - Google Patents

Info

Publication number: JPH0583588B2
Authority: JP; Japan
Prior art keywords: group; carbon atoms; less carbon; substituted; formula
Prior art date: 1985-10-09
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 - Fee Related

Application number

JP60225175A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6284158A (ja

Inventor

Toshinao Ukai

Hisashi Okada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujifilm Holdings Corp

Original Assignee

Fuji Photo Film Co Ltd

Priority date (The priority date 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 date listed.)

1985-10-09

Filing date

1985-10-09

Publication date

1993-11-26

1985-10-09 Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd

1985-10-09 Priority to JP60225175A priority Critical patent/JPS6284158A/ja

1987-04-17 Publication of JPS6284158A publication Critical patent/JPS6284158A/ja

1993-11-26 Publication of JPH0583588B2 publication Critical patent/JPH0583588B2/ja

Status Granted legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 claims description 4
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
PYWQACMPJZLKOQ-UHFFFAOYSA-N 1,3-tellurazole Chemical compound [Te]1C=CN=C1 PYWQACMPJZLKOQ-UHFFFAOYSA-N 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 claims description 4
WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000013078 crystal Substances 0.000 description 26
-1 vinylmethyl group Chemical group 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000975 dye Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
150000001875 compounds Chemical class 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
239000012046 mixed solvent Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RZGQBLWMLLDDKL-UHFFFAOYSA-N 2,6-dimethylpyran-4-thione Chemical compound CC1=CC(=S)C=C(C)O1 RZGQBLWMLLDDKL-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012456 homogeneous solution Substances 0.000 description 3
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 3
229910001488 sodium perchlorate Inorganic materials 0.000 description 3
ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical group C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
QMHIMXFNBOYPND-UHFFFAOYSA-N 4-methylthiazole Chemical compound CC1=CSC=N1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 description 2
ZLLOWHFKKIOINR-UHFFFAOYSA-N 5-phenyl-1,3-thiazole Chemical compound S1C=NC=C1C1=CC=CC=C1 ZLLOWHFKKIOINR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical group C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
239000000203 mixture Substances 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
125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BREUOIWLJRZAFF-UHFFFAOYSA-N 1,3-benzothiazol-5-ol Chemical compound OC1=CC=C2SC=NC2=C1 BREUOIWLJRZAFF-UHFFFAOYSA-N 0.000 description 1
ORIIXCOYEOIFSN-UHFFFAOYSA-N 1,3-benzothiazol-6-ol Chemical compound OC1=CC=C2N=CSC2=C1 ORIIXCOYEOIFSN-UHFFFAOYSA-N 0.000 description 1
KZWJUNXNZGVOOS-UHFFFAOYSA-N 1,3-benzothiazole-5-carbonitrile Chemical compound N#CC1=CC=C2SC=NC2=C1 KZWJUNXNZGVOOS-UHFFFAOYSA-N 0.000 description 1
RBIZQDIIVYJNRS-UHFFFAOYSA-N 1,3-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=NC2=C1 RBIZQDIIVYJNRS-UHFFFAOYSA-N 0.000 description 1
UPPYOQWUJKAFSG-UHFFFAOYSA-N 1,3-benzoxazol-5-ol Chemical compound OC1=CC=C2OC=NC2=C1 UPPYOQWUJKAFSG-UHFFFAOYSA-N 0.000 description 1
SAHAKBXWZLDNAA-UHFFFAOYSA-N 1,3-benzoxazol-6-ol Chemical compound OC1=CC=C2N=COC2=C1 SAHAKBXWZLDNAA-UHFFFAOYSA-N 0.000 description 1
ALUQMCBDQKDRAK-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1,3-benzothiazole Chemical compound C1C=CC=C2SCNC21 ALUQMCBDQKDRAK-UHFFFAOYSA-N 0.000 description 1
GBBJPBIYHSMRHL-UHFFFAOYSA-M 2,3-dimethyl-1,3-benzoxazol-3-ium;4-methylbenzenesulfonate Chemical compound C1=CC=C2[N+](C)=C(C)OC2=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 GBBJPBIYHSMRHL-UHFFFAOYSA-M 0.000 description 1
JKTQHJKAIBONLQ-UHFFFAOYSA-N 2-amino-4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(N)=C1 JKTQHJKAIBONLQ-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 1
UWSONZCNXUSTKW-UHFFFAOYSA-N 4,5-Dimethylthiazole Chemical compound CC=1N=CSC=1C UWSONZCNXUSTKW-UHFFFAOYSA-N 0.000 description 1
ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical compound O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 description 1
QBQQTGIZSOGZBT-UHFFFAOYSA-N 4,5-diphenyl-1,3-selenazole Chemical compound [se]1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QBQQTGIZSOGZBT-UHFFFAOYSA-N 0.000 description 1
BGTVICKPWACXLR-UHFFFAOYSA-N 4,5-diphenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BGTVICKPWACXLR-UHFFFAOYSA-N 0.000 description 1
NDUHYERSZLRFNL-UHFFFAOYSA-N 4,6-dimethyl-1,3-benzoxazole Chemical compound CC1=CC(C)=C2N=COC2=C1 NDUHYERSZLRFNL-UHFFFAOYSA-N 0.000 description 1
IFEPGHPDQJOYGG-UHFFFAOYSA-N 4-chloro-1,3-benzothiazole Chemical compound ClC1=CC=CC2=C1N=CS2 IFEPGHPDQJOYGG-UHFFFAOYSA-N 0.000 description 1
GQPBBURQQRLAKF-UHFFFAOYSA-N 4-ethyl-1,3-oxazole Chemical compound CCC1=COC=N1 GQPBBURQQRLAKF-UHFFFAOYSA-N 0.000 description 1
XQPAPBLJJLIQGV-UHFFFAOYSA-N 4-methoxy-1,3-benzothiazole Chemical compound COC1=CC=CC2=C1N=CS2 XQPAPBLJJLIQGV-UHFFFAOYSA-N 0.000 description 1
PIUXNZAIHQAHBY-UHFFFAOYSA-N 4-methyl-1,3-benzothiazole Chemical compound CC1=CC=CC2=C1N=CS2 PIUXNZAIHQAHBY-UHFFFAOYSA-N 0.000 description 1
PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 1
BJATXNRFAXUVCU-UHFFFAOYSA-N 4-methyl-1,3-selenazole Chemical compound CC1=C[se]C=N1 BJATXNRFAXUVCU-UHFFFAOYSA-N 0.000 description 1
NTFMLYSGIKHECT-UHFFFAOYSA-N 4-phenyl-1,3-oxazole Chemical compound O1C=NC(C=2C=CC=CC=2)=C1 NTFMLYSGIKHECT-UHFFFAOYSA-N 0.000 description 1
MLBGDGWUZBTFHT-UHFFFAOYSA-N 4-phenyl-1,3-selenazole Chemical compound [se]1C=NC(C=2C=CC=CC=2)=C1 MLBGDGWUZBTFHT-UHFFFAOYSA-N 0.000 description 1
KXCQDIWJQBSUJF-UHFFFAOYSA-N 4-phenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1 KXCQDIWJQBSUJF-UHFFFAOYSA-N 0.000 description 1
HYXKRZZFKJHDRT-UHFFFAOYSA-N 5,6-dimethoxy-1,3-benzothiazole Chemical compound C1=C(OC)C(OC)=CC2=C1SC=N2 HYXKRZZFKJHDRT-UHFFFAOYSA-N 0.000 description 1
QMUXKZBRYRPIPQ-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzothiazole Chemical compound C1=C(C)C(C)=CC2=C1SC=N2 QMUXKZBRYRPIPQ-UHFFFAOYSA-N 0.000 description 1
RWNMLYACWNIEIG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzoxazole Chemical compound C1=C(C)C(C)=CC2=C1OC=N2 RWNMLYACWNIEIG-UHFFFAOYSA-N 0.000 description 1
ODSGKKPRKQLYDA-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2SC=NC2=C1 ODSGKKPRKQLYDA-UHFFFAOYSA-N 0.000 description 1
KFDDRUWQFQJGNL-UHFFFAOYSA-N 5-bromo-1,3-benzothiazole Chemical compound BrC1=CC=C2SC=NC2=C1 KFDDRUWQFQJGNL-UHFFFAOYSA-N 0.000 description 1
DUMYZVKQCMCQHJ-UHFFFAOYSA-N 5-chloro-1,3-benzoselenazole Chemical compound ClC1=CC=C2[se]C=NC2=C1 DUMYZVKQCMCQHJ-UHFFFAOYSA-N 0.000 description 1
YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 description 1
VWMQXAYLHOSRKA-UHFFFAOYSA-N 5-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC=NC2=C1 VWMQXAYLHOSRKA-UHFFFAOYSA-N 0.000 description 1
GYXTWUJZURSNCF-UHFFFAOYSA-M 5-chloro-3-ethyl-2-methyl-1,3-benzothiazol-3-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=C(Cl)C=C2[N+](CC)=C(C)SC2=C1 GYXTWUJZURSNCF-UHFFFAOYSA-M 0.000 description 1
GWKNDCJHRNOQAR-UHFFFAOYSA-N 5-ethoxy-1,3-benzothiazole Chemical compound CCOC1=CC=C2SC=NC2=C1 GWKNDCJHRNOQAR-UHFFFAOYSA-N 0.000 description 1
MHWNEQOZIDVGJS-UHFFFAOYSA-N 5-ethoxy-1,3-benzoxazole Chemical compound CCOC1=CC=C2OC=NC2=C1 MHWNEQOZIDVGJS-UHFFFAOYSA-N 0.000 description 1
CEPRZYJDQRSAOJ-UHFFFAOYSA-N 5-ethoxybenzo[g][1,3]benzothiazole Chemical compound C12=CC=CC=C2C(OCC)=CC2=C1SC=N2 CEPRZYJDQRSAOJ-UHFFFAOYSA-N 0.000 description 1
ZRMPAEOUOPNNPZ-UHFFFAOYSA-N 5-fluoro-1,3-benzoxazole Chemical compound FC1=CC=C2OC=NC2=C1 ZRMPAEOUOPNNPZ-UHFFFAOYSA-N 0.000 description 1
AHIHYPVDBXEDMN-UHFFFAOYSA-N 5-methoxy-1,3-benzoselenazole Chemical compound COC1=CC=C2[se]C=NC2=C1 AHIHYPVDBXEDMN-UHFFFAOYSA-N 0.000 description 1
PNJKZDLZKILFNF-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2SC=NC2=C1 PNJKZDLZKILFNF-UHFFFAOYSA-N 0.000 description 1
IQQKXTVYGHYXFX-UHFFFAOYSA-N 5-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2OC=NC2=C1 IQQKXTVYGHYXFX-UHFFFAOYSA-N 0.000 description 1
VGUKLAIGOXRABB-UHFFFAOYSA-N 5-methoxybenzo[g][1,3]benzothiazole Chemical compound C12=CC=CC=C2C(OC)=CC2=C1SC=N2 VGUKLAIGOXRABB-UHFFFAOYSA-N 0.000 description 1
LDDVDAMRGURWPF-UHFFFAOYSA-N 5-methyl-1,3-benzoselenazole Chemical compound CC1=CC=C2[se]C=NC2=C1 LDDVDAMRGURWPF-UHFFFAOYSA-N 0.000 description 1
SEBIXVUYSFOUEL-UHFFFAOYSA-N 5-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC=NC2=C1 SEBIXVUYSFOUEL-UHFFFAOYSA-N 0.000 description 1
UBIAVBGIRDRQLD-UHFFFAOYSA-N 5-methyl-1,3-benzoxazole Chemical compound CC1=CC=C2OC=NC2=C1 UBIAVBGIRDRQLD-UHFFFAOYSA-N 0.000 description 1
ZYMHCFYHVYGFMS-UHFFFAOYSA-N 5-methyl-1,3-oxazole Chemical compound CC1=CN=CO1 ZYMHCFYHVYGFMS-UHFFFAOYSA-N 0.000 description 1
RLYUNPNLXMSXAX-UHFFFAOYSA-N 5-methylthiazole Chemical compound CC1=CN=CS1 RLYUNPNLXMSXAX-UHFFFAOYSA-N 0.000 description 1
LUDNKXQULYIPDQ-UHFFFAOYSA-N 5-phenyl-1,3-benzoselenazole Chemical compound C=1C=C2[se]C=NC2=CC=1C1=CC=CC=C1 LUDNKXQULYIPDQ-UHFFFAOYSA-N 0.000 description 1
AAKPXIJKSNGOCO-UHFFFAOYSA-N 5-phenyl-1,3-benzothiazole Chemical compound C=1C=C2SC=NC2=CC=1C1=CC=CC=C1 AAKPXIJKSNGOCO-UHFFFAOYSA-N 0.000 description 1
NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 description 1
YPYPBEGIASEWKA-UHFFFAOYSA-N 5-phenyl-1,3-oxazole Chemical compound O1C=NC=C1C1=CC=CC=C1 YPYPBEGIASEWKA-UHFFFAOYSA-N 0.000 description 1
YJOUISWKEOXIMC-UHFFFAOYSA-N 6-bromo-1,3-benzothiazole Chemical compound BrC1=CC=C2N=CSC2=C1 YJOUISWKEOXIMC-UHFFFAOYSA-N 0.000 description 1
AIBQGOMAISTKSR-UHFFFAOYSA-N 6-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2N=CSC2=C1 AIBQGOMAISTKSR-UHFFFAOYSA-N 0.000 description 1
GKJSZXGYFJBYRQ-UHFFFAOYSA-N 6-chloroquinoline Chemical compound N1=CC=CC2=CC(Cl)=CC=C21 GKJSZXGYFJBYRQ-UHFFFAOYSA-N 0.000 description 1
AJAKVPMSAABZRX-UHFFFAOYSA-N 6-ethoxyquinoline Chemical compound N1=CC=CC2=CC(OCC)=CC=C21 AJAKVPMSAABZRX-UHFFFAOYSA-N 0.000 description 1
VDOYSQQOKJDYDR-UHFFFAOYSA-N 6-ethylquinoline Chemical compound N1=CC=CC2=CC(CC)=CC=C21 VDOYSQQOKJDYDR-UHFFFAOYSA-N 0.000 description 1
AHOIGFLSEXUWNV-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2N=CSC2=C1 AHOIGFLSEXUWNV-UHFFFAOYSA-N 0.000 description 1
FKYKJYSYSGEDCG-UHFFFAOYSA-N 6-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2N=COC2=C1 FKYKJYSYSGEDCG-UHFFFAOYSA-N 0.000 description 1
IVKILQAPNDCUNJ-UHFFFAOYSA-N 6-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2N=CSC2=C1 IVKILQAPNDCUNJ-UHFFFAOYSA-N 0.000 description 1
SZWNDAUMBWLYOQ-UHFFFAOYSA-N 6-methylbenzoxazole Chemical compound CC1=CC=C2N=COC2=C1 SZWNDAUMBWLYOQ-UHFFFAOYSA-N 0.000 description 1
RXEDQOMFMWCKFW-UHFFFAOYSA-N 7-chloro-1,3-benzothiazole Chemical compound ClC1=CC=CC2=C1SC=N2 RXEDQOMFMWCKFW-UHFFFAOYSA-N 0.000 description 1
NCPZTZXDHOIMDV-UHFFFAOYSA-N 7-methoxybenzo[e][1,3]benzothiazole Chemical compound C1=CC2=CC(OC)=CC=C2C2=C1SC=N2 NCPZTZXDHOIMDV-UHFFFAOYSA-N 0.000 description 1
RNAAXKYOTPSFGV-UHFFFAOYSA-N 8-fluoroquinoline Chemical compound C1=CN=C2C(F)=CC=CC2=C1 RNAAXKYOTPSFGV-UHFFFAOYSA-N 0.000 description 1
NGQVHYQMKZKLAM-UHFFFAOYSA-N 8-methoxybenzo[e][1,3]benzothiazole Chemical compound C12=CC(OC)=CC=C2C=CC2=C1N=CS2 NGQVHYQMKZKLAM-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
241001061127 Thione Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
MWGUHVCAWGDKNU-UHFFFAOYSA-N benzo[f][1,3]benzoselenazole Chemical compound C1=CC=C2C=C([se]C=N3)C3=CC2=C1 MWGUHVCAWGDKNU-UHFFFAOYSA-N 0.000 description 1
HJLDPBXWNCCXGM-UHFFFAOYSA-N benzo[f][1,3]benzothiazole Chemical compound C1=CC=C2C=C(SC=N3)C3=CC2=C1 HJLDPBXWNCCXGM-UHFFFAOYSA-N 0.000 description 1
GYTPOXPRHJKGHD-UHFFFAOYSA-N benzo[f][1,3]benzoxazole Chemical compound C1=CC=C2C=C(OC=N3)C3=CC2=C1 GYTPOXPRHJKGHD-UHFFFAOYSA-N 0.000 description 1
IEICFDLIJMHYQB-UHFFFAOYSA-N benzo[g][1,3]benzoselenazole Chemical compound C1=CC=CC2=C([se]C=N3)C3=CC=C21 IEICFDLIJMHYQB-UHFFFAOYSA-N 0.000 description 1
IIUUNAJWKSTFPF-UHFFFAOYSA-N benzo[g][1,3]benzothiazole Chemical compound C1=CC=CC2=C(SC=N3)C3=CC=C21 IIUUNAJWKSTFPF-UHFFFAOYSA-N 0.000 description 1
BVVBQOJNXLFIIG-UHFFFAOYSA-N benzo[g][1,3]benzoxazole Chemical compound C1=CC=CC2=C(OC=N3)C3=CC=C21 BVVBQOJNXLFIIG-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
230000005284 excitation Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
239000000990 laser dye Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
WWANKXYUVUCOMI-UHFFFAOYSA-N pyran-4-thione Chemical compound S=C1C=COC=C1 WWANKXYUVUCOMI-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
239000010865 sewage Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

JP60225175A 1985-10-09 1985-10-09 新規メチン染料 Granted JPS6284158A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60225175A JPS6284158A (ja)	1985-10-09	1985-10-09	新規メチン染料

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60225175A JPS6284158A (ja)	1985-10-09	1985-10-09	新規メチン染料

Publications (2)

Publication Number	Publication Date
JPS6284158A JPS6284158A (ja)	1987-04-17
JPH0583588B2 true JPH0583588B2 (fr)	1993-11-26

Family

ID=16825127

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60225175A Granted JPS6284158A (ja)	1985-10-09	1985-10-09	新規メチン染料

Country Status (1)

Country	Link
JP (1)	JPS6284158A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2105298A1 (fr)	2008-03-28	2009-09-30	Fujifilm Corporation	Précurseur de plaque d'impression lithographique à action négative et son procédé d'impression lithographique

1985
- 1985-10-09 JP JP60225175A patent/JPS6284158A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2105298A1 (fr)	2008-03-28	2009-09-30	Fujifilm Corporation	Précurseur de plaque d'impression lithographique à action négative et son procédé d'impression lithographique

Also Published As

Publication number	Publication date
JPS6284158A (ja)	1987-04-17

Legal Events

Date	Code	Title	Description
2003-11-26	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
US2977229A (en)	1961-03-28	Supersensitized emulsions comprising simple cyanine dyes
US3671648A (en)	1972-06-20	Carbocyanine filter dyes and sensitizers for silver halide emulsions
US3639127A (en)	1972-02-01	Silver halide emulsions containing a dye derived from 4,6-diaryl substituted picolinium salts as desensitizer
US5397690A (en)	1995-03-14	Near-infrared absorbing dyes prepared from stenhouse salts
US2955939A (en)	1960-10-11	Holopolar cyanine dyes and photographic emulsions containing them
US4025349A (en)	1977-05-24	Silver halide photographic elements spectrally sensitized with an acetylenic analog of cyanine or merocyanine dyes
US5440042A (en)	1995-08-08	Thioheterocyclic near-infrared dyes
US3326688A (en)	1967-06-20	Photographic sensitizing dyes
US2882159A (en)	1959-04-14	Merocyanine sensitizing dyes and photographic emulsions containing them
US3469985A (en)	1969-09-30	Light-absorbing dyes derived from barbituric and 2 - thiobarbituric acid compounds useful for photography and their preparation
US3715351A (en)	1973-02-06	Cyanine dyes containing a cyclopentanone nucleus
US3440052A (en)	1969-04-22	Sensitized silver halide emulsions with holopolar dyes containing a dilactone ring
US4030932A (en)	1977-06-21	Silver halide sensitized with dyes containing an isoindole nucleus
US4026884A (en)	1977-05-31	Methyne dyes and photographic elements
JPH0583588B2 (fr)	1993-11-26
US5424442A (en)	1995-06-13	Water-soluble methine compounds useful in photographic silver halide emulsion containing the same
US4283488A (en)	1981-08-11	Photographic compositions and elements spectrally sensitized with new methine dyes
US3483196A (en)	1969-12-09	Imidazo(4,5-b) quinolinium salts and cyanine,merocyanine and styryl photographic sensitizing dyes derived therefrom
US4080496A (en)	1978-03-21	Methyne dyes and photographic elements
US3557101A (en)	1971-01-19	Trinuclear dyes having an acid nucleus substituted with a secondary amino substituted alkyl group useful as spectral sensitizers for photographic silver halide emulsions
US2980671A (en)	1961-04-18	Monomethine cyanine dyes and method for preparing them
US3772278A (en)	1973-11-13	Novel hexahydroindolizine and hexahydroquinolizine cyanine dyes
US5514809A (en)	1996-05-07	Silver halide photographic material
US3936308A (en)	1976-02-03	Photographic emulsions containing methine dyes having a 1H-imidazo[4,5-b]pyrazine nucleus
JPH06895B2 (ja)	1994-01-05	新規メチン染料

JPH0583588B2 - - Google Patents

Info

Links

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=16825127

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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