JPH0421675B2 - - Google Patents
Info
- Publication number
- JPH0421675B2 JPH0421675B2 JP59056139A JP5613984A JPH0421675B2 JP H0421675 B2 JPH0421675 B2 JP H0421675B2 JP 59056139 A JP59056139 A JP 59056139A JP 5613984 A JP5613984 A JP 5613984A JP H0421675 B2 JPH0421675 B2 JP H0421675B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- type
- dibutylamino
- methyl
- anilinofluorane
- 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
- 230000004048 modification Effects 0.000 claims description 20
- 238000012986 modification Methods 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 11
- 238000002441 X-ray diffraction Methods 0.000 claims description 7
- 238000010586 diagram Methods 0.000 claims description 4
- MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000009466 transformation Effects 0.000 description 11
- 238000004040 coloring Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000029052 metamorphosis Effects 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- 230000015572 biosynthetic process Effects 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
- 238000010438 heat treatment Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- -1 2-(4'-dibutylamino-2'-hydroxybenzoyl)benzoin Chemical compound 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
- JRYQVCAISWBJMB-UHFFFAOYSA-N 3-(5-anilino-2-methoxyphenyl)-3-[4-(dibutylamino)-2-hydroxyphenyl]-2-benzofuran-1-one Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C1(C=2C(=CC=C(NC=3C=CC=CC=3)C=2)OC)C2=CC=CC=C2C(=O)O1 JRYQVCAISWBJMB-UHFFFAOYSA-N 0.000 description 1
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59056139A JPS60202155A (ja) | 1984-03-26 | 1984-03-26 | ３−ジブチルアミノ−６−メチル−７−アニリノフルオランの結晶変態 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59056139A JPS60202155A (ja) | 1984-03-26 | 1984-03-26 | ３−ジブチルアミノ−６−メチル−７−アニリノフルオランの結晶変態 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60202155A JPS60202155A (ja) | 1985-10-12 |
| JPH0421675B2 true JPH0421675B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-13 |
Family
ID=13018740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59056139A Granted JPS60202155A (ja) | 1984-03-26 | 1984-03-26 | ３−ジブチルアミノ−６−メチル−７−アニリノフルオランの結晶変態 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60202155A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69012910T2 (de) * | 1989-07-19 | 1995-05-18 | Mitsui Toatsu Chemicals | Fluoran-Verbindungen, kristalline Toluol-Addukte davon, Aufzeichnungsmaterial damit und Verfahren zu deren Herstellung. |
| JPH0662864B2 (ja) * | 1989-12-25 | 1994-08-17 | 山本化成株式会社 | ３―ジブチルアミノ―６ーメチル―７―アニリノフルオランの製造方法 |
| EP0462480B1 (en) * | 1990-06-19 | 1999-03-24 | Mitsui Chemicals, Inc. | Heat sensitive recording material and preparation process of said material |
| US5955398A (en) * | 1997-04-25 | 1999-09-21 | Appleton Papers Inc. | Thermally-responsive record material |
-
1984
- 1984-03-26 JP JP59056139A patent/JPS60202155A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60202155A (ja) | 1985-10-12 |
Similar Documents
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |