CH401060A - Procédé de préparation de nouveaux composés stilbéniques - Google Patents
Procédé de préparation de nouveaux composés stilbéniquesInfo
- Publication number
- CH401060A CH401060A CH47665A CH47665A CH401060A CH 401060 A CH401060 A CH 401060A CH 47665 A CH47665 A CH 47665A CH 47665 A CH47665 A CH 47665A CH 401060 A CH401060 A CH 401060A
- Authority
- CH
- Switzerland
- Prior art keywords
- stilbene
- bis
- benzoxazol
- cyano
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 arylalkl Chemical group 0.000 claims description 110
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- VNXSSSWJLVDBIK-UHFFFAOYSA-N COC(C=C1)=CC(O)=C1NC(C1=CC=C(C=CC(C=C2)=CC=C2C(NC(C=CC(OC)=C2)=C2O)=O)C=C1)=O Chemical compound COC(C=C1)=CC(O)=C1NC(C1=CC=C(C=CC(C=C2)=CC=C2C(NC(C=CC(OC)=C2)=C2O)=O)C=C1)=O VNXSSSWJLVDBIK-UHFFFAOYSA-N 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 3
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 3
- KNLOVRYVXXVZMR-UHFFFAOYSA-N 5-(1,3-benzoxazol-2-yl)-2-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]aniline Chemical compound O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC1=C(N2)C=CC=C1)N KNLOVRYVXXVZMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000005282 brightening Methods 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- LFBAJNKRKWIDJG-UHFFFAOYSA-N 2-[4-[2-[4-(1,3-benzoxazol-2-yl)-2-methylphenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(C=3C=C(C(=CC=3)C=CC=3C=CC(=CC=3)C=3OC4=CC=CC=C4N=3)C)=NC2=C1 LFBAJNKRKWIDJG-UHFFFAOYSA-N 0.000 description 2
- QILKKAFYAFEWGU-UHFFFAOYSA-N 4-(cyanomethyl)benzonitrile Chemical compound N#CCC1=CC=C(C#N)C=C1 QILKKAFYAFEWGU-UHFFFAOYSA-N 0.000 description 2
- ZKXGEOSWQSVEBT-UHFFFAOYSA-N 4-[2-(4-carbonochloridoylphenyl)ethenyl]benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C=CC1=CC=C(C(Cl)=O)C=C1 ZKXGEOSWQSVEBT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VNZDFZRMNASODX-UHFFFAOYSA-N O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=C(C=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C)C Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=C(C=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C)C VNZDFZRMNASODX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- XEXHCQJRVMVJMY-UHFFFAOYSA-N (4-bromophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Br)C=C1 XEXHCQJRVMVJMY-UHFFFAOYSA-N 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- YFNDPOKNTFXBJI-UHFFFAOYSA-N 1-[5-(1,3-benzoxazol-2-yl)-2-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]ethanone Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C(C)=O YFNDPOKNTFXBJI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SLGUYROXMMXJLV-UHFFFAOYSA-N 2-[4-[2-[4-(1,3-benzoxazol-2-yl)-2-methylsulfonylphenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)S(=O)(=O)C SLGUYROXMMXJLV-UHFFFAOYSA-N 0.000 description 1
- ORACIQIJMCYPHQ-UHFFFAOYSA-N 2-[4-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(C3=CC=C(C=C3)C=CC=3C=CC(=CC=3)C=3OC4=CC=CC=C4N=3)=NC2=C1 ORACIQIJMCYPHQ-UHFFFAOYSA-N 0.000 description 1
- OZJUZNLAMBMVQC-UHFFFAOYSA-N 2-[4-[2-[4-(5-cyano-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole-5-carbonitrile Chemical compound N#CC1=CC=C2OC(C3=CC=C(C=C3)C=CC3=CC=C(C=C3)C=3OC4=CC=C(C=C4N=3)C#N)=NC2=C1 OZJUZNLAMBMVQC-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- AOWNYDDZDLTCGB-UHFFFAOYSA-N 2-amino-5-methoxyphenol Chemical compound COC1=CC=C(N)C(O)=C1 AOWNYDDZDLTCGB-UHFFFAOYSA-N 0.000 description 1
- IXGURTAEYOZRDF-UHFFFAOYSA-N 2-amino-5-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(N)C(O)=C1 IXGURTAEYOZRDF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OONPLQJHBJXVBP-UHFFFAOYSA-N 3-(2-phenylethenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=CC=CC=2)=C1C(O)=O OONPLQJHBJXVBP-UHFFFAOYSA-N 0.000 description 1
- ZEWCASRNRWXXSO-UHFFFAOYSA-N 3-amino-4-hydroxybenzonitrile Chemical compound NC1=CC(C#N)=CC=C1O ZEWCASRNRWXXSO-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- QXAKVAPWQJMNIJ-UHFFFAOYSA-N 4-[2-(4-carbonochloridoylphenyl)ethenyl]-3-methylbenzoyl chloride Chemical compound CC1=C(C=CC(=C1)C(=O)Cl)C=CC1=CC=C(C=C1)C(=O)Cl QXAKVAPWQJMNIJ-UHFFFAOYSA-N 0.000 description 1
- QWFDIYQYJYTFSP-UHFFFAOYSA-N 4-[2-(4-carbonochloridoylphenyl)ethenyl]-3-nitrobenzoyl chloride Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)C(=O)Cl)C=CC1=CC=C(C=C1)C(=O)Cl QWFDIYQYJYTFSP-UHFFFAOYSA-N 0.000 description 1
- URQFSTJELYULDL-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)ethenyl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C=CC1=CC=C(C(O)=O)C=C1 URQFSTJELYULDL-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C=CC1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-UHFFFAOYSA-N 0.000 description 1
- RCBPVESMGNZMSG-UHFFFAOYSA-N 4-bromo-2-methylbenzaldehyde Chemical compound CC1=CC(Br)=CC=C1C=O RCBPVESMGNZMSG-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- KOFBNBCOGKLUOM-UHFFFAOYSA-N 4-methyl-3-nitrobenzonitrile Chemical compound CC1=CC=C(C#N)C=C1[N+]([O-])=O KOFBNBCOGKLUOM-UHFFFAOYSA-N 0.000 description 1
- YSJBNNQAFOPMHZ-UHFFFAOYSA-N 5-(1,3-benzoxazol-2-yl)-2-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]benzonitrile Chemical compound O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC1=C(N2)C=CC=C1)C#N YSJBNNQAFOPMHZ-UHFFFAOYSA-N 0.000 description 1
- VOPFWLAAAPXENU-UHFFFAOYSA-N 5-(5-methyl-1,3-benzoxazol-2-yl)-2-[2-[4-(5-methyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]benzonitrile Chemical compound CC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C)C#N)C=1 VOPFWLAAAPXENU-UHFFFAOYSA-N 0.000 description 1
- WLYGODSPPVFJDN-UHFFFAOYSA-N 5-[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]-2-[2-[4-[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]phenyl]ethenyl]benzonitrile Chemical compound FC(C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N2)C=C(C=C3)C(F)(F)F)C#N)C1)(F)F WLYGODSPPVFJDN-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- QTVYRXWHMHIALK-UHFFFAOYSA-N 5-methoxy-2-[4-[2-[4-(5-methoxy-1,3-benzoxazol-2-yl)-2-methylphenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound COC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N2)C=C(C=C3)OC)C)C1 QTVYRXWHMHIALK-UHFFFAOYSA-N 0.000 description 1
- DLQCBAGTHATVAR-UHFFFAOYSA-N 6-bromo-2-[4-[2-[4-(6-bromo-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound BrC1=CC2=C(N=C(O2)C2=CC=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=CC(=C3)Br)C=C1 DLQCBAGTHATVAR-UHFFFAOYSA-N 0.000 description 1
- WAKDCWCOXFUFGI-UHFFFAOYSA-N 6-chloro-2-[4-[2-[4-(6-chloro-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound ClC1=CC2=C(N=C(O2)C2=CC=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N2)C=CC(=C3)Cl)C=C1 WAKDCWCOXFUFGI-UHFFFAOYSA-N 0.000 description 1
- UGYRXFNWCOMMFJ-UHFFFAOYSA-N 6-methylsulfonyl-2-[4-[2-[4-(6-methylsulfonyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound C1=C(S(C)(=O)=O)C=C2OC(C3=CC=C(C=C3)C=CC3=CC=C(C=C3)C3=NC4=CC=C(C=C4O3)S(=O)(=O)C)=NC2=C1 UGYRXFNWCOMMFJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- AMWRLBFRHHKPSZ-UHFFFAOYSA-M BrC=1C=CC(=C(C=1)C)CC(=O)[O-].[K+] Chemical compound BrC=1C=CC(=C(C=1)C)CC(=O)[O-].[K+] AMWRLBFRHHKPSZ-UHFFFAOYSA-M 0.000 description 1
- YFMMCUICKPVHTH-UHFFFAOYSA-N C(#N)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C#N)C#N)C=1 Chemical compound C(#N)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C#N)C#N)C=1 YFMMCUICKPVHTH-UHFFFAOYSA-N 0.000 description 1
- OVAWOHPFVDPPLW-UHFFFAOYSA-N C(C)(=O)NC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)NC(C)=O)C#N)C=1 Chemical compound C(C)(=O)NC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)NC(C)=O)C#N)C=1 OVAWOHPFVDPPLW-UHFFFAOYSA-N 0.000 description 1
- LKUKPIHRWNHOBS-UHFFFAOYSA-N CC1=C(C=CC(=C1)C(=O)Cl)C=CC1=C(C=C(C=C1)C(=O)Cl)C Chemical compound CC1=C(C=CC(=C1)C(=O)Cl)C=CC1=C(C=C(C=C1)C(=O)Cl)C LKUKPIHRWNHOBS-UHFFFAOYSA-N 0.000 description 1
- QLLBCKSPRVWDCL-UHFFFAOYSA-N CN(S(=O)(=O)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)S(N(C)C)(=O)=O)C)C=1)C Chemical compound CN(S(=O)(=O)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)S(N(C)C)(=O)=O)C)C=1)C QLLBCKSPRVWDCL-UHFFFAOYSA-N 0.000 description 1
- JLQYMYPNHJKDKG-UHFFFAOYSA-N COC(C(C=C1)=CC2=C1N=C(C1=CC=C(C=C(C(C=C3)=CC=C3C3=NC(C=CC(C(OC)=O)=C4)=C4O3)C#N)C=C1)O2)=O Chemical compound COC(C(C=C1)=CC2=C1N=C(C1=CC=C(C=C(C(C=C3)=CC=C3C3=NC(C=CC(C(OC)=O)=C4)=C4O3)C#N)C=C1)O2)=O JLQYMYPNHJKDKG-UHFFFAOYSA-N 0.000 description 1
- LGCXFCALQSSTAL-UHFFFAOYSA-N COC1=CC=C(C=C1)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C2=CC=C(C=C2)OC)C#N)C=1 Chemical compound COC1=CC=C(C=C1)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C2=CC=C(C=C2)OC)C#N)C=1 LGCXFCALQSSTAL-UHFFFAOYSA-N 0.000 description 1
- NJYYEBNILJWIQQ-UHFFFAOYSA-N COC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)OC)C#N)C=1 Chemical compound COC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)OC)C#N)C=1 NJYYEBNILJWIQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZJFAAEPXAZDWKP-UHFFFAOYSA-N ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)Cl)Cl)C=1 Chemical compound ClC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)Cl)Cl)C=1 ZJFAAEPXAZDWKP-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IYCWJAZYAVLKNN-UHFFFAOYSA-N FC(C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C(F)(F)F)C)C=1)(F)F Chemical compound FC(C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C(F)(F)F)C)C=1)(F)F IYCWJAZYAVLKNN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OPTLNBBNNUWILL-UHFFFAOYSA-N IC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)I)C)C=1 Chemical compound IC=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)I)C)C=1 OPTLNBBNNUWILL-UHFFFAOYSA-N 0.000 description 1
- VEISQEYSKQJFIS-UHFFFAOYSA-N N#CC(C1=C(C(Cl)=O)C(C(Cl)=O)=CC=C1)=CC1=CC=CC=C1 Chemical compound N#CC(C1=C(C(Cl)=O)C(C(Cl)=O)=CC=C1)=CC1=CC=CC=C1 VEISQEYSKQJFIS-UHFFFAOYSA-N 0.000 description 1
- CZLHQTIBOGLIBP-UHFFFAOYSA-N N-(2-hydroxyphenyl)-4-[2-[4-[(2-hydroxyphenyl)carbamoyl]phenyl]ethenyl]benzamide Chemical compound OC1=C(NC(=O)C2=CC=C(C=CC3=CC=C(C=C3)C(=O)NC3=C(O)C=CC=C3)C=C2)C=CC=C1 CZLHQTIBOGLIBP-UHFFFAOYSA-N 0.000 description 1
- JWZQORBMNOGEJI-UHFFFAOYSA-N O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C(=O)OC Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C(=O)OC JWZQORBMNOGEJI-UHFFFAOYSA-N 0.000 description 1
- LWQQWVFZBYONDS-UHFFFAOYSA-N O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C(F)(F)F Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)C(F)(F)F LWQQWVFZBYONDS-UHFFFAOYSA-N 0.000 description 1
- NARCMHSSIFHRLU-UHFFFAOYSA-N O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)S(N(C)C)(=O)=O Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)S(N(C)C)(=O)=O NARCMHSSIFHRLU-UHFFFAOYSA-N 0.000 description 1
- XKAJHGDMWBSTPC-UHFFFAOYSA-N OC1=C(C=CC=C1)NC(=O)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C(NC1=C(C=CC=C1)O)=O)C Chemical compound OC1=C(C=CC=C1)NC(=O)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C(NC1=C(C=CC=C1)O)=O)C XKAJHGDMWBSTPC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- YZOUMXRFJNDIAI-UHFFFAOYSA-N [5-(1,3-benzoxazol-2-yl)-2-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl] thiocyanate Chemical compound O1C(=NC2=C1C=CC=C2)C1=CC(=C(C=C1)C=CC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC=C2)SC#N YZOUMXRFJNDIAI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 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
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XDRZQGLMZSHAMW-UHFFFAOYSA-N methyl 2-[4-[2-[2-cyano-4-(5-methoxycarbonyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole-5-carboxylate Chemical compound C(=O)(OC)C=1C=CC2=C(N=C(O2)C2=CC(=C(C=C2)C=CC2=CC=C(C=C2)C=2OC3=C(N=2)C=C(C=C3)C(=O)OC)C#N)C=1 XDRZQGLMZSHAMW-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940046549 textile allergenic extract Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47527/62A GB1072914A (en) | 1962-12-17 | 1962-12-17 | Bisbenzoxazolyl stilbenes and their use as fluorescent brightening agents |
| US263742A US3322680A (en) | 1962-12-17 | 1963-03-08 | Polymeric compositions containing a fluorescent brightening agent |
| US273283A US3260715A (en) | 1962-12-17 | 1963-04-16 | Fluorescent bis-benzoxazolyl stilbenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH401060A true CH401060A (fr) | 1965-10-31 |
Family
ID=27260007
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH47665A CH401060A (fr) | 1962-12-17 | 1963-12-17 | Procédé de préparation de nouveaux composés stilbéniques |
| CH47765A CH412316A (fr) | 1962-12-17 | 1963-12-17 | Utilisation de composés stilbéniques pour rendre des objets fluorescents |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH47765A CH412316A (fr) | 1962-12-17 | 1963-12-17 | Utilisation de composés stilbéniques pour rendre des objets fluorescents |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE641426A (enrdf_load_stackoverflow) |
| CA (1) | CA967569A (enrdf_load_stackoverflow) |
| CH (2) | CH401060A (enrdf_load_stackoverflow) |
| DE (1) | DE1445694C3 (enrdf_load_stackoverflow) |
| NL (2) | NL142192B (enrdf_load_stackoverflow) |
| SE (1) | SE315896B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1072914A (en) * | 1962-12-17 | 1967-06-21 | Kodak Ltd | Bisbenzoxazolyl stilbenes and their use as fluorescent brightening agents |
| DE2712686C2 (de) * | 1977-03-23 | 1986-09-04 | Bayer Ag, 5090 Leverkusen | 4-Triazinyl-4'-benzoxazolyl- bzw. 4'-phenyl-stilben-derivate |
| US4921964A (en) * | 1989-03-01 | 1990-05-01 | Eastman Kodak Company | Process for the preparation of stilbene derivatives |
| US5783307A (en) * | 1996-11-04 | 1998-07-21 | Eastman Chemical Company | UV stabilized multi-layer structures with detectable UV protective layers and a method of detection |
-
0
- NL NL301930D patent/NL301930A/xx unknown
-
1963
- 1963-12-16 DE DE19631445694 patent/DE1445694C3/de not_active Expired
- 1963-12-16 CA CA891,326A patent/CA967569A/en not_active Expired
- 1963-12-16 SE SE1396163A patent/SE315896B/xx unknown
- 1963-12-17 BE BE641426A patent/BE641426A/xx unknown
- 1963-12-17 CH CH47665A patent/CH401060A/fr unknown
- 1963-12-17 NL NL301930A patent/NL142192B/xx unknown
- 1963-12-17 CH CH47765A patent/CH412316A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL301930A (enrdf_load_stackoverflow) | |
| NL142192B (nl) | 1974-05-15 |
| CH412316A (fr) | 1966-04-30 |
| DE1445694B2 (de) | 1973-05-17 |
| CA967569A (en) | 1975-05-13 |
| DE1445694A1 (de) | 1968-12-19 |
| SE315896B (enrdf_load_stackoverflow) | 1969-10-13 |
| DE1445694C3 (de) | 1973-12-20 |
| BE641426A (enrdf_load_stackoverflow) | 1964-04-16 |
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