JPH0153279B2 - - Google Patents
Info
- Publication number
- JPH0153279B2 JPH0153279B2 JP56061259A JP6125981A JPH0153279B2 JP H0153279 B2 JPH0153279 B2 JP H0153279B2 JP 56061259 A JP56061259 A JP 56061259A JP 6125981 A JP6125981 A JP 6125981A JP H0153279 B2 JPH0153279 B2 JP H0153279B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- fluoran compound
- cyclohexyl
- fluoran
- methylbenzoyl
- 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
Links
- -1 fluoran compound Chemical class 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 30
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000011161 development Methods 0.000 description 12
- 239000005711 Benzoic acid Substances 0.000 description 11
- 235000010233 benzoic acid Nutrition 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 7
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FYMCXGILCMIOKD-UHFFFAOYSA-N (4-bromophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Br)C=C1 FYMCXGILCMIOKD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012965 benzophenone Substances 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
- 238000001035 drying Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 1
- YXMYPHLWXBXNFF-UHFFFAOYSA-N (2-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1Cl YXMYPHLWXBXNFF-UHFFFAOYSA-N 0.000 description 1
- XFTXWDDQIXYAGY-UHFFFAOYSA-N (3-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC(Cl)=C1 XFTXWDDQIXYAGY-UHFFFAOYSA-N 0.000 description 1
- YXCBKESUCSTXNW-UHFFFAOYSA-N (4-bromophenyl)-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=C(Br)C=C1 YXCBKESUCSTXNW-UHFFFAOYSA-N 0.000 description 1
- POHRRVPQMJGTKX-UHFFFAOYSA-N (4-bromophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(Br)C=C1 POHRRVPQMJGTKX-UHFFFAOYSA-N 0.000 description 1
- RFKLPMBHTYGGHV-UHFFFAOYSA-N (4-bromophenyl)-(3-chlorophenyl)methanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC(Br)=CC=2)=C1 RFKLPMBHTYGGHV-UHFFFAOYSA-N 0.000 description 1
- CKOJVDGMHBXDGZ-UHFFFAOYSA-N (4-bromophenyl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(Br)=CC=2)=C1 CKOJVDGMHBXDGZ-UHFFFAOYSA-N 0.000 description 1
- HYLHMBIFGKMXHZ-UHFFFAOYSA-N (4-bromophenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(Br)C=C1 HYLHMBIFGKMXHZ-UHFFFAOYSA-N 0.000 description 1
- OUQFWKJOKONNMD-UHFFFAOYSA-N (4-chlorophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 OUQFWKJOKONNMD-UHFFFAOYSA-N 0.000 description 1
- QNLZAQKYBMIIPN-UHFFFAOYSA-N (4-chlorophenyl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1 QNLZAQKYBMIIPN-UHFFFAOYSA-N 0.000 description 1
- MRIBPIAKCVDXLY-UHFFFAOYSA-N (4-chlorophenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 MRIBPIAKCVDXLY-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
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XVAIDCNLVLTVFM-UHFFFAOYSA-N methacetin Chemical compound COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56061259A JPS57177058A (en) | 1981-04-24 | 1981-04-24 | Novel fluoran compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56061259A JPS57177058A (en) | 1981-04-24 | 1981-04-24 | Novel fluoran compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57177058A JPS57177058A (en) | 1982-10-30 |
| JPH0153279B2 true JPH0153279B2 (enrdf_load_stackoverflow) | 1989-11-13 |
Family
ID=13166051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56061259A Granted JPS57177058A (en) | 1981-04-24 | 1981-04-24 | Novel fluoran compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57177058A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59120655A (ja) * | 1982-12-27 | 1984-07-12 | Kanzaki Paper Mfg Co Ltd | フルオラン誘導体、その製造方法およびその誘導体を用いた記録体 |
| ES2287040T3 (es) | 1999-12-06 | 2007-12-16 | Leo Pharma A/S | Aminobenzopenonas como inhibidores de il-beta y tnf-alfa. |
| JP2003534327A (ja) | 2000-05-22 | 2003-11-18 | レオ・ファーマ・アクティーゼルスカブ | ＩＬ−１βおよびＴＮＦ−αの抑制剤としてのベンゾフェノン |
| WO2003018535A2 (en) | 2001-08-28 | 2003-03-06 | Leo Pharma A/S | Novel aminobenzoephenones |
-
1981
- 1981-04-24 JP JP56061259A patent/JPS57177058A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57177058A (en) | 1982-10-30 |
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