DE3438083C2 - - Google Patents
Info
- Publication number
- DE3438083C2 DE3438083C2 DE3438083A DE3438083A DE3438083C2 DE 3438083 C2 DE3438083 C2 DE 3438083C2 DE 3438083 A DE3438083 A DE 3438083A DE 3438083 A DE3438083 A DE 3438083A DE 3438083 C2 DE3438083 C2 DE 3438083C2
- Authority
- DE
- Germany
- Prior art keywords
- azaphthalide
- diethylamino
- ethyl
- methylindol
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 4-dimethylamino-2-n-pentyloxyphenyl Chemical group 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- RFADXDHLVFZIJX-UHFFFAOYSA-N 7-[2-cyclohexyloxy-4-(diethylamino)phenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=NC=CC=C3C(=O)O2)C=2C3=CC=CC=C3N(CC)C=2C)C=1OC1CCCCC1 RFADXDHLVFZIJX-UHFFFAOYSA-N 0.000 claims description 6
- OOVLTPREOVATAH-UHFFFAOYSA-N 7-[4-(diethylamino)-2-pentoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 OOVLTPREOVATAH-UHFFFAOYSA-N 0.000 claims description 5
- UAZOKXDYTOJNCS-UHFFFAOYSA-N 7-[2-cyclopentyloxy-4-(diethylamino)phenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=NC=CC=C3C(=O)O2)C=2C3=CC=CC=C3N(CC)C=2C)C=1OC1CCCC1 UAZOKXDYTOJNCS-UHFFFAOYSA-N 0.000 claims description 4
- YDYKGVWORCQOTN-UHFFFAOYSA-N 7-[4-(diethylamino)-2-hexoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 YDYKGVWORCQOTN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- RMYGXFVWJOHGAA-UHFFFAOYSA-N 5-[4-(diethylamino)-2-(3-methylbutoxy)phenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CC(C)CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=CC=CN=C2C(=O)O1 RMYGXFVWJOHGAA-UHFFFAOYSA-N 0.000 claims description 3
- VIHJMAPRLIOYER-UHFFFAOYSA-N 5h-furo[3,4-b]pyridin-7-one Chemical class C1=CN=C2C(=O)OCC2=C1 VIHJMAPRLIOYER-UHFFFAOYSA-N 0.000 claims description 3
- UMDYFCPRQVKGMJ-UHFFFAOYSA-N 7-[2-cyclohexyloxy-4-(diethylamino)phenyl]-7-(1,2-dimethylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=NC=CC=C3C(=O)O2)C=2C3=CC=CC=C3N(C)C=2C)C=1OC1CCCCC1 UMDYFCPRQVKGMJ-UHFFFAOYSA-N 0.000 claims description 3
- NOAXDBHRNFKDNS-UHFFFAOYSA-N 7-[4-(diethylamino)-2-pentoxyphenyl]-7-(1,2-dimethylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(C)C=2C)C2=NC=CC=C2C(=O)O1 NOAXDBHRNFKDNS-UHFFFAOYSA-N 0.000 claims description 3
- VJWGCSOSYXFOGN-UHFFFAOYSA-N 5-[2-cyclohexyloxy-4-(diethylamino)phenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CN=C3C(=O)O2)C=2C3=CC=CC=C3N(CC)C=2C)C=1OC1CCCCC1 VJWGCSOSYXFOGN-UHFFFAOYSA-N 0.000 claims description 2
- DTCHVSGFFWVRCQ-UHFFFAOYSA-N 5-[4-(diethylamino)-2-pentoxyphenyl]-5-(1,2-dimethylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CCCCCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(C)C=2C)C2=CC=CN=C2C(=O)O1 DTCHVSGFFWVRCQ-UHFFFAOYSA-N 0.000 claims description 2
- NMHNWIYMMBQGHG-UHFFFAOYSA-N 7-[4-(diethylamino)-2-(3-methylbutoxy)phenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CC(C)CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 NMHNWIYMMBQGHG-UHFFFAOYSA-N 0.000 claims description 2
- JPAQVRNKWHVPAT-UHFFFAOYSA-N 7-[4-(dimethylamino)-2-hexoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCCOC1=CC(N(C)C)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 JPAQVRNKWHVPAT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- 238000004519 manufacturing process Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000008018 melting Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- 241000894007 species Species 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YYNRCYXUNHOLEF-UHFFFAOYSA-N 2-(3-carboxypyridine-2-carbonyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C(=O)C1=NC=CC=C1C(O)=O YYNRCYXUNHOLEF-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- QTKIQLNGOKOPOE-UHFFFAOYSA-N 1,1'-biphenyl;propane Chemical group CCC.C1=CC=CC=C1C1=CC=CC=C1 QTKIQLNGOKOPOE-UHFFFAOYSA-N 0.000 description 2
- ZVCFSCXUODRMKI-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)pyridine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=CC=CN=C1C(O)=O ZVCFSCXUODRMKI-UHFFFAOYSA-N 0.000 description 2
- PWTHCWXOBIJAJB-UHFFFAOYSA-N 3-cyclohexyloxy-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(OC2CCCCC2)=C1 PWTHCWXOBIJAJB-UHFFFAOYSA-N 0.000 description 2
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 244000172533 Viola sororia Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- YLZSIUVOIFJGQZ-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1 YLZSIUVOIFJGQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- SKNGWALGKBQFEE-UHFFFAOYSA-N n,n-diethyl-3-pentoxyaniline Chemical compound CCCCCOC1=CC=CC(N(CC)CC)=C1 SKNGWALGKBQFEE-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000004961 triphenylmethanes Chemical class 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VTNYYSAUAVLYST-UHFFFAOYSA-N 2-(1,2-dimethylindole-3-carbonyl)pyridine-3-carboxylic acid Chemical compound C12=CC=CC=C2N(C)C(C)=C1C(=O)C1=NC=CC=C1C(O)=O VTNYYSAUAVLYST-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- FXSFKECPPGDGBN-UHFFFAOYSA-N 3,3-bis(1h-indol-2-yl)-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(C=1NC2=CC=CC=C2C=1)C1=CC2=CC=CC=C2N1 FXSFKECPPGDGBN-UHFFFAOYSA-N 0.000 description 1
- GBHOCQOMJNPVPW-UHFFFAOYSA-N 3,3-bis(2-aminophenyl)-2-benzofuran-1-one Chemical compound NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C(=O)O1 GBHOCQOMJNPVPW-UHFFFAOYSA-N 0.000 description 1
- NLUIMKRQKMUZRW-UHFFFAOYSA-N 3-cyclopentyloxy-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(OC2CCCC2)=C1 NLUIMKRQKMUZRW-UHFFFAOYSA-N 0.000 description 1
- CCTDUNZVTODJPS-UHFFFAOYSA-N 3-hexoxy-n,n-dimethylaniline Chemical compound CCCCCCOC1=CC=CC(N(C)C)=C1 CCTDUNZVTODJPS-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OIIAWEYLHHHZJC-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=CC=CN=C2C(=O)O1 OIIAWEYLHHHZJC-UHFFFAOYSA-N 0.000 description 1
- UWNCCTHTVWXHGM-UHFFFAOYSA-N 7-[2-cyclohexyloxy-4-(diethylamino)phenyl]-7-(2-methyl-1-propylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C(C)N(C1=CC(=C(C=C1)C1(OC(=O)C2=CC=CN=C12)C1=C(N(C2=CC=CC=C12)CCC)C)OC1CCCCC1)CC UWNCCTHTVWXHGM-UHFFFAOYSA-N 0.000 description 1
- RCVMSMLWRJESQC-UHFFFAOYSA-N 7-[4-(diethylamino)-2-ethoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 RCVMSMLWRJESQC-UHFFFAOYSA-N 0.000 description 1
- IRJUFWKFESQGEM-UHFFFAOYSA-N 7-[4-(dimethylamino)-2-pentoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCOC1=CC(N(C)C)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 IRJUFWKFESQGEM-UHFFFAOYSA-N 0.000 description 1
- YSJHADWSLVFGGT-UHFFFAOYSA-N 7h-furo[3,4-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)OCC2=N1 YSJHADWSLVFGGT-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940054021 anxiolytics diphenylmethane derivative Drugs 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
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XVSPLFSNFXZIDP-UHFFFAOYSA-N n,n-diethyl-3-(3-methylbutoxy)aniline Chemical compound CCN(CC)C1=CC=CC(OCCC(C)C)=C1 XVSPLFSNFXZIDP-UHFFFAOYSA-N 0.000 description 1
- SIKHCVBXOVKOTL-UHFFFAOYSA-N n,n-diethyl-3-hexoxyaniline Chemical compound CCCCCCOC1=CC=CC(N(CC)CC)=C1 SIKHCVBXOVKOTL-UHFFFAOYSA-N 0.000 description 1
- JWWFJMHMIWMGDL-UHFFFAOYSA-N n,n-dimethyl-3-pentoxyaniline Chemical compound CCCCCOC1=CC=CC(N(C)C)=C1 JWWFJMHMIWMGDL-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N salicylic acid benzyl ester Natural products OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—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)
- Indole Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58195448A JPS6085986A (ja) | 1983-10-18 | 1983-10-18 | 発色性記録材料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3438083A1 DE3438083A1 (de) | 1985-05-02 |
| DE3438083C2 true DE3438083C2 (en, 2012) | 1990-01-18 |
Family
ID=16341232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843438083 Granted DE3438083A1 (de) | 1983-10-18 | 1984-10-17 | Chromogene azaphthalidverbindung und sie enthaltende farbbildende aufzeichnungszusammensetzung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4747875A (en, 2012) |
| JP (1) | JPS6085986A (en, 2012) |
| DE (1) | DE3438083A1 (en, 2012) |
| FR (1) | FR2553425B1 (en, 2012) |
| GB (1) | GB2148923B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4660060A (en) * | 1985-06-17 | 1987-04-21 | The Hilton-Davis Chemical Co. | Imaging systems containing 3-(indol-3-yl)-3-(4-substituted aminophenyl)phthalides |
| JPS6313778A (ja) * | 1986-07-04 | 1988-01-21 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6317078A (ja) * | 1986-07-09 | 1988-01-25 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6331788A (ja) * | 1986-07-28 | 1988-02-10 | Fuji Photo Film Co Ltd | 感圧記録シ−ト |
| JPS6317077A (ja) * | 1986-07-09 | 1988-01-25 | Fuji Photo Film Co Ltd | 記録材料 |
| GB2193981B (en) * | 1986-07-09 | 1990-05-23 | Fuji Photo Film Co Ltd | Sheet recording material containing dye forming components |
| JPS6331789A (ja) * | 1986-07-28 | 1988-02-10 | Fuji Photo Film Co Ltd | 感圧記録シ−ト |
| JPH0692192B2 (ja) * | 1986-07-25 | 1994-11-16 | 富士写真フイルム株式会社 | 感圧記録シ−ト |
| JPS6362778A (ja) * | 1986-09-03 | 1988-03-19 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6367179A (ja) * | 1986-09-08 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| JPS6367180A (ja) * | 1986-09-09 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| DE3752344D1 (de) * | 1986-10-28 | 2002-01-17 | Ciba Sc Holding Ag | Chromogene Phthalide |
| JPS63158287A (ja) * | 1986-12-22 | 1988-07-01 | Fuji Photo Film Co Ltd | 記録材料 |
| JPH0641227B2 (ja) * | 1987-07-15 | 1994-06-01 | 富士写真フイルム株式会社 | 記録材料 |
| JP5595449B2 (ja) * | 2011-10-25 | 2014-09-24 | 三菱鉛筆株式会社 | 色素、それを用いたマイクロカプセル顔料及び筆記具用インク組成物 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3594369A (en) * | 1969-01-21 | 1971-07-20 | Ncr Co | 3,5(6)-disubstituted-3-(para-diloweralkyl-aminophenyl) phthalides |
| JPS4916726B1 (en, 2012) * | 1970-12-28 | 1974-04-24 | ||
| US3736337A (en) * | 1971-04-27 | 1973-05-29 | Ncr Co | Tetrahalogenated chromogenic compounds and their use |
| BE791898A (fr) * | 1971-11-26 | 1973-05-24 | Ciba Geigy Ag | Procede de preparation de substances chromogenes a partir d'indoles et d'anhydrides d'acides dicarboxyliques vicinaux, aromatiques ou heteroaromatiques, nouveaux chromogenes de cette categorie et leur emploi |
| BE791793A (fr) * | 1971-12-06 | 1973-03-16 | Ncr Co | Composes chromogenes |
| JPS505116A (en, 2012) * | 1973-05-16 | 1975-01-20 | ||
| GB1460751A (en) * | 1973-05-21 | 1977-01-06 | Ciba Geigy Ag | 3-indolyl-3-phenyl-phthalide compounds their manufacture and their use |
| GB1460151A (en) * | 1973-05-21 | 1976-12-31 | Ciba Geigy | Nitrophthalides their mahufacture and their use in recording systems- |
| JPS5138245B2 (en, 2012) * | 1973-05-22 | 1976-10-20 | ||
| GB1467898A (en) * | 1974-04-09 | 1977-03-23 | Ciba Geigy Ag | Heterocyclic substituted lactone compounds their manufacture and use |
| JPS5138243A (ja) * | 1974-09-30 | 1976-03-30 | Toshiba Tungaloy Co Ltd | Chokogokinbotainitankachitan oyobi chitsukachitankaranarufukugotaiohifukusuruhoho |
| GB1564559A (en) * | 1976-12-29 | 1980-04-10 | Sterling Drug Inc | 3(diphenylamino) phthalides |
| US4189171A (en) * | 1977-03-01 | 1980-02-19 | Sterling Drug Inc. | Marking systems containing 3-aryl-3-heterylphthalides and 3,3-bis(heteryl)phthalides |
| CA1110244A (en) * | 1977-09-29 | 1981-10-06 | Troy E. Hoover | Synthesis of chromogenic indolylphenyldihydrofuropyridin-one compounds |
| US4349679A (en) * | 1978-05-18 | 1982-09-14 | Giba-Geigy Corporation | Pyrrolidino and piperidino benz ring substituted phthalides |
| US4275905A (en) * | 1978-12-29 | 1981-06-30 | Appleton Papers Inc. | Pressure-sensitive record material |
| GR73674B (en, 2012) * | 1978-12-29 | 1984-03-29 | Appleton Paper Inc | |
| US4242513A (en) * | 1979-03-05 | 1980-12-30 | Appleton Papers Inc. | Lactone compounds containing a heterocyclic radical |
| US4275206A (en) * | 1979-03-05 | 1981-06-23 | Appleton Papers Inc. | Lactone compounds containing an indolizine radical |
| DE2937525A1 (de) * | 1979-09-17 | 1981-03-19 | Yamada Chemical Co. Ltd., Kyoto | Neue chromogene verbindungen und ihre verwendung als farbbildner in kopier- oder aufzeichnungsmaterialien |
| JPS56151597A (en) * | 1980-04-28 | 1981-11-24 | Yamamoto Kagaku Gosei Kk | Recording material |
| JPS57212092A (en) * | 1981-06-23 | 1982-12-27 | Yamada Kagaku Kogyo Kk | Color-forming recording material |
| US4668790A (en) * | 1981-12-23 | 1987-05-26 | Ciba-Geigy Corporation | Chromogenic dihydrofuropyridinones |
| DE3469531D1 (en) * | 1983-09-15 | 1988-04-07 | Ciba Geigy Ag | 5- and 6-azaphthalides, their mixture of isomers, process for their production and their use in recording materials which are sensitive to pressure and heat |
-
1983
- 1983-10-18 JP JP58195448A patent/JPS6085986A/ja active Pending
-
1984
- 1984-10-17 FR FR8415903A patent/FR2553425B1/fr not_active Expired
- 1984-10-17 GB GB08426293A patent/GB2148923B/en not_active Expired
- 1984-10-17 DE DE19843438083 patent/DE3438083A1/de active Granted
-
1987
- 1987-06-26 US US07/067,395 patent/US4747875A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4747875A (en) | 1988-05-31 |
| FR2553425B1 (fr) | 1987-07-17 |
| GB2148923A (en) | 1985-06-05 |
| JPS6085986A (ja) | 1985-05-15 |
| GB2148923B (en) | 1987-03-11 |
| DE3438083A1 (de) | 1985-05-02 |
| GB8426293D0 (en) | 1984-11-21 |
| FR2553425A1 (fr) | 1985-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8128 | New person/name/address of the agent |
Representative=s name: KADOR, U., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8125 | Change of the main classification |
Ipc: C07D491/048 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |