JPH0435505B2 - - Google Patents
Info
- Publication number
- JPH0435505B2 JPH0435505B2 JP58008095A JP809583A JPH0435505B2 JP H0435505 B2 JPH0435505 B2 JP H0435505B2 JP 58008095 A JP58008095 A JP 58008095A JP 809583 A JP809583 A JP 809583A JP H0435505 B2 JPH0435505 B2 JP H0435505B2
- Authority
- JP
- Japan
- Prior art keywords
- fluoran
- toluene
- general formula
- color
- fluorane
- 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 - Lifetime
Links
- -1 hyperidino group Chemical group 0.000 claims description 28
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 141
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 35
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 32
- 239000000047 product Substances 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 239000000126 substance Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012965 benzophenone Substances 0.000 description 11
- 238000011161 development Methods 0.000 description 10
- FQNKTJPBXAZUGC-UHFFFAOYSA-N 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FQNKTJPBXAZUGC-UHFFFAOYSA-N 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical class FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- DUDXQHGWYWTEGF-UHFFFAOYSA-N N-phenyl-6-sulfonylcyclohexa-2,4-dien-1-amine Chemical compound S(=O)(=O)=C1C(NC2=CC=CC=C2)C=CC=C1 DUDXQHGWYWTEGF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011268 mixed slurry Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OHLGNIVLMQBOLM-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-methylpiperidine Chemical compound C1C(C)CCCN1S(=O)(=O)C1=CC=C(Br)C=C1 OHLGNIVLMQBOLM-UHFFFAOYSA-N 0.000 description 1
- CBNDEXDYZUNXBF-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-methylpiperazine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(Br)C=C1 CBNDEXDYZUNXBF-UHFFFAOYSA-N 0.000 description 1
- GTXWMYDMGGSQOD-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-methylpiperidine Chemical compound C1CC(C)CCN1S(=O)(=O)C1=CC=C(Br)C=C1 GTXWMYDMGGSQOD-UHFFFAOYSA-N 0.000 description 1
- CRHZHJNOPUDTDM-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonylazepane Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCCCCC1 CRHZHJNOPUDTDM-UHFFFAOYSA-N 0.000 description 1
- AVWJTUSLSQWCFK-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonylpiperidine Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCCCC1 AVWJTUSLSQWCFK-UHFFFAOYSA-N 0.000 description 1
- JMOJWOSNSJXQMT-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonylpyrrolidine Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCCC1 JMOJWOSNSJXQMT-UHFFFAOYSA-N 0.000 description 1
- FXKRATLJGPAUHB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CCCC1 FXKRATLJGPAUHB-UHFFFAOYSA-N 0.000 description 1
- WQFYAGVHZYFXDO-UHFFFAOYSA-N 2'-anilino-6'-(diethylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 WQFYAGVHZYFXDO-UHFFFAOYSA-N 0.000 description 1
- BWFYTAYBGCKKBE-UHFFFAOYSA-N 2-(2-hydroxy-4-piperidin-1-ylbenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N2CCCCC2)C=C1O BWFYTAYBGCKKBE-UHFFFAOYSA-N 0.000 description 1
- XUYADCDXDRMDEV-UHFFFAOYSA-N 2-(2-hydroxy-4-pyrrolidin-1-ylbenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N2CCCC2)C=C1O XUYADCDXDRMDEV-UHFFFAOYSA-N 0.000 description 1
- QPNFUBAIQZJEPO-UHFFFAOYSA-N 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPNFUBAIQZJEPO-UHFFFAOYSA-N 0.000 description 1
- GLELQLHCSRTFFD-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1C(O)=O GLELQLHCSRTFFD-UHFFFAOYSA-N 0.000 description 1
- QXGZXDUYFNMZPE-UHFFFAOYSA-N 2-[4-(dipropylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCC)CCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QXGZXDUYFNMZPE-UHFFFAOYSA-N 0.000 description 1
- JWJRLABLXQZFAR-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonylmorpholine Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCOCC1 JWJRLABLXQZFAR-UHFFFAOYSA-N 0.000 description 1
- CQRAZPMQHFWMKD-UHFFFAOYSA-N 5-bromo-6-sulfonylcyclohexa-1,3-diene Chemical compound BrC1C=CC=CC1=S(=O)=O CQRAZPMQHFWMKD-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZUHAMUOTLKEYAA-UHFFFAOYSA-N n-fluoro-n-methylcyclohexanamine Chemical compound CN(F)C1CCCCC1 ZUHAMUOTLKEYAA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58008095A JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58008095A JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59135255A JPS59135255A (ja) | 1984-08-03 |
| JPH0435505B2 true JPH0435505B2 (fr) | 1992-06-11 |
Family
ID=11683749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58008095A Granted JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59135255A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2139852A1 (fr) | 2006-12-19 | 2010-01-06 | Pharmos Corporation | Dérivés sulfonamides avec indications thérapeutiques |
-
1983
- 1983-01-22 JP JP58008095A patent/JPS59135255A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59135255A (ja) | 1984-08-03 |
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