FI70035C - Kromogent laktonmaterial - Google Patents
Kromogent laktonmaterial Download PDFInfo
- Publication number
- FI70035C FI70035C FI800652A FI800652A FI70035C FI 70035 C FI70035 C FI 70035C FI 800652 A FI800652 A FI 800652A FI 800652 A FI800652 A FI 800652A FI 70035 C FI70035 C FI 70035C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- ethyl
- dihydrofuro
- phenyl
- formula
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 51
- 239000000126 substance Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 150000004715 keto acids Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 103
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 96
- -1 4-morpholinophenyl Chemical group 0.000 description 78
- 239000000243 solution Substances 0.000 description 63
- 239000000047 product Substances 0.000 description 43
- 239000000203 mixture Substances 0.000 description 39
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000004927 clay Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 239000000908 ammonium hydroxide Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 10
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 10
- 239000012485 toluene extract Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- ADEKJVNFIQUGRR-UHFFFAOYSA-N 4h-pyridin-3-one Chemical compound O=C1CC=CN=C1 ADEKJVNFIQUGRR-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 229920001568 phenolic resin Polymers 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000003094 microcapsule Substances 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- UFZCVNIUMATMLR-UHFFFAOYSA-N ethyl 2-phenylindolizine-1-carboxylate Chemical compound C=1N2C=CC=CC2=C(C(=O)OCC)C=1C1=CC=CC=C1 UFZCVNIUMATMLR-UHFFFAOYSA-N 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 5
- ZWVBUDPQGPFIRX-UHFFFAOYSA-N 2-(1-ethyl-2-methylindole-3-carbonyl)benzoic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=CC=CC=C1C(O)=O ZWVBUDPQGPFIRX-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- JLSCJJNNDGOVRK-UHFFFAOYSA-N 1,2-diphenylindolizine Chemical compound C=12C=CC=CN2C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 JLSCJJNNDGOVRK-UHFFFAOYSA-N 0.000 description 4
- QRBYEBPQYCYKFF-UHFFFAOYSA-N 2-[4-(diethylamino)-2-ethoxybenzoyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CC=C1C(O)=O QRBYEBPQYCYKFF-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SBVPYBFMIGDIDX-SRVKXCTJSA-N Pro-Pro-Pro Chemical compound OC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)[C@H]2NCCC2)CCC1 SBVPYBFMIGDIDX-SRVKXCTJSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 125000000457 gamma-lactone group Chemical group 0.000 description 4
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HGLISOFZJUBYPD-UHFFFAOYSA-N 2-(1-ethyl-2-methylindole-3-carbonyl)pyridine-3-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC=CC=C1C(O)=O HGLISOFZJUBYPD-UHFFFAOYSA-N 0.000 description 3
- MOAJARXSAJETQE-UHFFFAOYSA-N 6-ethyl-3-methyl-2-phenylindolizine Chemical compound CC=1N2C=C(CC)C=CC2=CC=1C1=CC=CC=C1 MOAJARXSAJETQE-UHFFFAOYSA-N 0.000 description 3
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 description 2
- GMPFIYIVJWVDEA-UHFFFAOYSA-N 2,3-dimethylindolizine Chemical compound C1=CC=CN2C(C)=C(C)C=C21 GMPFIYIVJWVDEA-UHFFFAOYSA-N 0.000 description 2
- JMCYJDYOEWQZDE-UHFFFAOYSA-N 2-phenylindolizine Chemical compound C=1N2C=CC=CC2=CC=1C1=CC=CC=C1 JMCYJDYOEWQZDE-UHFFFAOYSA-N 0.000 description 2
- MJTDPRXHSURKFB-UHFFFAOYSA-N 3-(1,2-diphenylindolizin-3-yl)-3-(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C1(C2=CC=CC=C2C(=O)O1)C(N1C=CC=CC1=1)=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 MJTDPRXHSURKFB-UHFFFAOYSA-N 0.000 description 2
- WWGPNVKONOEGCX-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(6-ethyl-3-methyl-2-phenylindolizin-1-yl)-2-benzofuran-1-one Chemical compound CC=1N2C=C(CC)C=CC2=C(C2(C3=CC=CC=C3C(=O)O2)C=2C3=CC=CC=C3N(CC)C=2C)C=1C1=CC=CC=C1 WWGPNVKONOEGCX-UHFFFAOYSA-N 0.000 description 2
- SBIKQLHNIATNDF-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(6-ethyl-3-methyl-2-phenylindolizin-1-yl)-4-nitro-2-benzofuran-1-one Chemical compound CC=1N2C=C(CC)C=CC2=C(C2(C3=C(C=CC=C3C(=O)O2)[N+]([O-])=O)C=2C3=CC=CC=C3N(CC)C=2C)C=1C1=CC=CC=C1 SBIKQLHNIATNDF-UHFFFAOYSA-N 0.000 description 2
- BALHXGOKLWUZGE-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-[1-(1-methylnaphthalen-2-yl)indolizin-3-yl]-2-benzofuran-1-one Chemical compound C1=CC=CN2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(C)N(C4=CC=CC=C43)CC)=CC(C=3C(=C4C=CC=CC4=CC=3)C)=C21 BALHXGOKLWUZGE-UHFFFAOYSA-N 0.000 description 2
- LDKYOLLFGDAFKH-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methoxyphenyl]-3-(2,3-dimethylindolizin-1-yl)-2-benzofuran-1-one Chemical compound COC1=CC(N(CC)CC)=CC=C1C1(C2=C3C=CC=CN3C(C)=C2C)C2=CC=CC=C2C(=O)O1 LDKYOLLFGDAFKH-UHFFFAOYSA-N 0.000 description 2
- PEJRAMOKDWVBQF-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-(2,3-dimethylindolizin-1-yl)-3-(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound CC1=C(C)N2C=CC=CC2=C1C1(C2=C(C(=C(Cl)C(Cl)=C2Cl)Cl)C(=O)O1)C1=C(C)N(CC)C2=CC=CC=C21 PEJRAMOKDWVBQF-UHFFFAOYSA-N 0.000 description 2
- SFQPYJQUGCNJOR-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(6-ethyl-3-methyl-2-phenylindolizin-1-yl)furo[3,4-b]pyridin-7-one Chemical compound C(C)N(C1=CC(=C(C=C1)C1(OC(C2=NC=CC=C21)=O)C=1C(=C(N2C=C(C=CC=12)CC)C)C1=CC=CC=C1)OCC)CC SFQPYJQUGCNJOR-UHFFFAOYSA-N 0.000 description 2
- SFLQYQFXMOTVML-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(3-methyl-2-phenylindolizin-1-yl)-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C=1C(=C(N2C=CC=CC12)C)C1=CC=CC=C1)C SFLQYQFXMOTVML-UHFFFAOYSA-N 0.000 description 2
- RQMZVEPGPQUNNO-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(6-ethyl-3-methyl-2-phenylindolizin-1-yl)-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C=1C(=C(N2C=C(C=CC=12)CC)C)C1=CC=CC=C1)C RQMZVEPGPQUNNO-UHFFFAOYSA-N 0.000 description 2
- WYKCFJUQHCPMOJ-UHFFFAOYSA-N 7-(1,2-diphenylindolizin-3-yl)-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C1(C2=NC=CC=C2C(=O)O1)C(N1C=CC=CC1=1)=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 WYKCFJUQHCPMOJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003593 chromogenic compound Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- DZHZYUHWJJYONT-UHFFFAOYSA-N ethyl 3-[1-(1-ethyl-2-methylindol-3-yl)-3-oxo-2-benzofuran-1-yl]-2-phenylindolizine-1-carboxylate Chemical compound O1C(=O)C2=CC=CC=C2C1(C=1C2=CC=CC=C2N(CC)C=1C)C=1N2C=CC=CC2=C(C(=O)OCC)C=1C1=CC=CC=C1 DZHZYUHWJJYONT-UHFFFAOYSA-N 0.000 description 2
- VKSWZVKIEKLDEC-UHFFFAOYSA-N ethyl 3-[1-[4-(diethylamino)-2-ethoxyphenyl]-3-oxo-2-benzofuran-1-yl]-2-phenylindolizine-1-carboxylate Chemical compound N12C=CC=CC2=C(C(=O)OCC)C(C=2C=CC=CC=2)=C1C1(C2=CC=CC=C2C(=O)O1)C1=CC=C(N(CC)CC)C=C1OCC VKSWZVKIEKLDEC-UHFFFAOYSA-N 0.000 description 2
- GECYSGXTXUDZJA-UHFFFAOYSA-N ethyl 3-[7-[4-(diethylamino)-2-ethoxyphenyl]-5-oxofuro[3,4-b]pyridin-7-yl]-2-phenylindolizine-1-carboxylate Chemical compound N12C=CC=CC2=C(C(=O)OCC)C(C=2C=CC=CC=2)=C1C1(C2=NC=CC=C2C(=O)O1)C1=CC=C(N(CC)CC)C=C1OCC GECYSGXTXUDZJA-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004538 indolizin-3-yl group Chemical group C=1C=C(N2C=CC=CC12)* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical compound C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- ZLFDMWVCAPSKJN-UHFFFAOYSA-N (1-propylcyclohexa-2,4-dien-1-yl)benzene Chemical group C(CC)C1(CC=CC=C1)C1=CC=CC=C1 ZLFDMWVCAPSKJN-UHFFFAOYSA-N 0.000 description 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 description 1
- ZVRPQDBYKXNEAH-UHFFFAOYSA-N 1-methyl-2-phenylindolizine Chemical compound C=1N2C=CC=CC2=C(C)C=1C1=CC=CC=C1 ZVRPQDBYKXNEAH-UHFFFAOYSA-N 0.000 description 1
- XETHUYLPOULFPF-UHFFFAOYSA-N 1-methylindolizine Chemical compound C1=CC=CC2=C(C)C=CN21 XETHUYLPOULFPF-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- WELCYWIRXVLUGM-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-(1-ethyl-2-methylindole-3-carbonyl)benzoic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WELCYWIRXVLUGM-UHFFFAOYSA-N 0.000 description 1
- YYXUAUNEFIARAF-UHFFFAOYSA-N 2,3-diphenylindolizine Chemical compound N12C=CC=CC2=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YYXUAUNEFIARAF-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003265 Resimene® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- IUDKTVXSXWAKJO-UHFFFAOYSA-N ethyl 2-pyridin-2-ylacetate Chemical compound CCOC(=O)CC1=CC=CC=N1 IUDKTVXSXWAKJO-UHFFFAOYSA-N 0.000 description 1
- IGVZZQRGTPQMDA-UHFFFAOYSA-N ethyl 3-[7-(1-ethyl-2-methylindol-3-yl)-5-oxofuro[3,4-b]pyridin-7-yl]-2-phenylindolizine-1-carboxylate Chemical compound O1C(=O)C2=CC=CN=C2C1(C=1C2=CC=CC=C2N(CC)C=1C)C=1N2C=CC=CC2=C(C(=O)OCC)C=1C1=CC=CC=C1 IGVZZQRGTPQMDA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108010077112 prolyl-proline Proteins 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/017,764 US4232887A (en) | 1979-03-05 | 1979-03-05 | Lactone compounds containing an indolizine radical |
| US1776479 | 1979-03-05 | ||
| US06/112,500 US4275206A (en) | 1979-03-05 | 1980-01-16 | Lactone compounds containing an indolizine radical |
| US11250080 | 1980-01-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI800652A7 FI800652A7 (fi) | 1980-09-06 |
| FI70035B FI70035B (fi) | 1986-01-31 |
| FI70035C true FI70035C (fi) | 1986-09-12 |
Family
ID=26690284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI800652A FI70035C (fi) | 1979-03-05 | 1980-03-03 | Kromogent laktonmaterial |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4275206A (enExample) |
| AT (1) | AT377761B (enExample) |
| AU (1) | AU540061B2 (enExample) |
| BR (1) | BR8001263A (enExample) |
| CA (1) | CA1147728A (enExample) |
| CH (1) | CH656138A5 (enExample) |
| DE (1) | DE3008475A1 (enExample) |
| DK (1) | DK91380A (enExample) |
| ES (1) | ES8104364A1 (enExample) |
| FI (1) | FI70035C (enExample) |
| FR (1) | FR2450858A1 (enExample) |
| GB (1) | GB2044284B (enExample) |
| GR (1) | GR67690B (enExample) |
| HK (1) | HK74184A (enExample) |
| IE (1) | IE49537B1 (enExample) |
| IT (1) | IT1209313B (enExample) |
| LU (1) | LU82216A1 (enExample) |
| NL (1) | NL174146C (enExample) |
| NO (1) | NO800611L (enExample) |
| NZ (1) | NZ192980A (enExample) |
| PT (1) | PT70871A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508384B1 (fr) * | 1981-06-24 | 1986-06-20 | Aussedat Rey | Nouveaux developpeurs de couleur, compositions d'enregistrement thermographique les contenant et supports correspondants |
| CH653353A5 (de) * | 1983-05-09 | 1985-12-31 | Ciba Geigy Ag | Chromogene 3,3-bisindolyl-4-azaphthalide. |
| JPS6085986A (ja) * | 1983-10-18 | 1985-05-15 | Yamada Kagaku Kogyo Kk | 発色性記録材料 |
| JPH0764987B2 (ja) * | 1987-02-13 | 1995-07-12 | 富士写真フイルム株式会社 | 近赤外ロイコ染料及び該染料を含む記録材料 |
| US5200519A (en) * | 1992-01-03 | 1993-04-06 | Appleton Papers Inc. | Mono(indolylethylenyl)phthalides |
| FR2805460A1 (fr) | 2000-02-25 | 2001-08-31 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives d'indolizine cationiques et procede de teinture |
| CN1701069A (zh) * | 2002-09-27 | 2005-11-23 | 詹森药业有限公司 | 3,4－二取代吡咯及其在治疗炎性疾病中的应用 |
| US20050165131A1 (en) * | 2003-10-06 | 2005-07-28 | Terry Stovold | Invisible ink |
| US8053494B2 (en) * | 2003-10-06 | 2011-11-08 | Nocopi Technologies, Inc. | Invisible ink and scratch pad |
| US20050075420A1 (en) * | 2003-10-06 | 2005-04-07 | Terry Stovold | Invisible ink |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491116A (en) | 1967-01-30 | 1970-01-20 | Ncr Co | 3-(phenyl)-3-(indol-3-yl)-phthalides |
| US3509174A (en) * | 1967-01-30 | 1970-04-28 | Ncr Co | 3-(indol-3-yl)-phthalides |
| US3736337A (en) * | 1971-04-27 | 1973-05-29 | Ncr Co | Tetrahalogenated chromogenic compounds and their use |
| BE791793A (fr) * | 1971-12-06 | 1973-03-16 | Ncr Co | Composes chromogenes |
| GB1465669A (en) * | 1972-12-28 | 1977-02-23 | Agfa Gevaert | Pressure sensitive recording materials and pressure-recording procews |
| GB1460751A (en) * | 1973-05-21 | 1977-01-06 | Ciba Geigy Ag | 3-indolyl-3-phenyl-phthalide compounds their manufacture and their use |
| JPS5031917A (enExample) * | 1973-07-24 | 1975-03-28 | ||
| US4020068A (en) * | 1974-05-08 | 1977-04-26 | Ncr Corporation | Chromogenic furoquinoxalines |
| US4016174A (en) * | 1975-04-10 | 1977-04-05 | Ncr Corporation | Benzoindole phthalides |
| JPS525746A (en) * | 1975-07-03 | 1977-01-17 | Kanzaki Paper Mfg Co Ltd | Novel process for preparation of triarymethane derivatives |
| US4032545A (en) * | 1975-09-29 | 1977-06-28 | Polaroid Corporation | Phthalides and naphthalides |
| CH594511A5 (enExample) * | 1976-01-16 | 1978-01-13 | Ciba Geigy Ag | |
| ES462577A1 (es) * | 1976-09-24 | 1978-07-16 | Sterling Drug Inc | Un procedimiento para preparar acidos 2-(alfa,alfa-aril-yno heteril disustituido)-metilbenzoicos. |
-
1980
- 1980-01-16 US US06/112,500 patent/US4275206A/en not_active Expired - Lifetime
- 1980-02-12 CA CA000345510A patent/CA1147728A/en not_active Expired
- 1980-02-26 PT PT70871A patent/PT70871A/pt unknown
- 1980-02-26 NZ NZ192980A patent/NZ192980A/xx unknown
- 1980-03-03 FI FI800652A patent/FI70035C/fi not_active IP Right Cessation
- 1980-03-03 BR BR8001263A patent/BR8001263A/pt unknown
- 1980-03-03 LU LU82216A patent/LU82216A1/fr unknown
- 1980-03-04 CH CH1714/80A patent/CH656138A5/de not_active IP Right Cessation
- 1980-03-04 IE IE433/80A patent/IE49537B1/en unknown
- 1980-03-04 AT AT0119380A patent/AT377761B/de not_active IP Right Cessation
- 1980-03-04 ES ES489160A patent/ES8104364A1/es not_active Expired
- 1980-03-04 DK DK91380A patent/DK91380A/da not_active Application Discontinuation
- 1980-03-04 NO NO800611A patent/NO800611L/no unknown
- 1980-03-05 NL NLAANVRAGE8001316,A patent/NL174146C/xx not_active IP Right Cessation
- 1980-03-05 FR FR8004999A patent/FR2450858A1/fr active Granted
- 1980-03-05 GB GB8007564A patent/GB2044284B/en not_active Expired
- 1980-03-05 IT IT8020374A patent/IT1209313B/it active
- 1980-03-05 AU AU56161/80A patent/AU540061B2/en not_active Ceased
- 1980-03-05 DE DE19803008475 patent/DE3008475A1/de active Granted
- 1980-03-05 GR GR61359A patent/GR67690B/el unknown
-
1984
- 1984-09-27 HK HK741/84A patent/HK74184A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR8001263A (pt) | 1980-11-04 |
| PT70871A (en) | 1980-03-01 |
| NZ192980A (en) | 1982-11-23 |
| CA1147728A (en) | 1983-06-07 |
| DE3008475C2 (enExample) | 1988-05-26 |
| FI800652A7 (fi) | 1980-09-06 |
| AU5616180A (en) | 1980-09-11 |
| ATA119380A (de) | 1984-09-15 |
| NL174146C (nl) | 1984-05-01 |
| GB2044284A (en) | 1980-10-15 |
| NL174146B (nl) | 1983-12-01 |
| IE800433L (en) | 1980-09-05 |
| AT377761B (de) | 1985-04-25 |
| US4275206A (en) | 1981-06-23 |
| ES489160A0 (es) | 1981-04-01 |
| HK74184A (en) | 1984-10-05 |
| ES8104364A1 (es) | 1981-04-01 |
| DE3008475A1 (de) | 1980-09-18 |
| IT8020374A0 (it) | 1980-03-05 |
| AU540061B2 (en) | 1984-11-01 |
| LU82216A1 (fr) | 1980-09-24 |
| IE49537B1 (en) | 1985-10-30 |
| CH656138A5 (de) | 1986-06-13 |
| NO800611L (no) | 1980-09-08 |
| GR67690B (enExample) | 1981-09-07 |
| DK91380A (da) | 1980-09-06 |
| NL8001316A (nl) | 1980-09-09 |
| FI70035B (fi) | 1986-01-31 |
| FR2450858B1 (enExample) | 1981-10-16 |
| FR2450858A1 (fr) | 1980-10-03 |
| IT1209313B (it) | 1989-07-16 |
| GB2044284B (en) | 1983-04-20 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
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