JPS60202155A - 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 - Google Patents
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Info
- Publication number
- JPS60202155A JPS60202155A JP59056139A JP5613984A JPS60202155A JP S60202155 A JPS60202155 A JP S60202155A JP 59056139 A JP59056139 A JP 59056139A JP 5613984 A JP5613984 A JP 5613984A JP S60202155 A JPS60202155 A JP S60202155A
- Authority
- JP
- Japan
- Prior art keywords
- dibutylamino
- methyl
- modification
- anilinofluoran
- parts
- 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.)
- Granted
Links
- 238000012986 modification Methods 0.000 title claims abstract description 18
- 230000004048 modification Effects 0.000 title claims abstract description 18
- 239000013078 crystal Substances 0.000 title claims abstract description 14
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 title abstract 3
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 11
- 238000004383 yellowing Methods 0.000 abstract description 6
- 150000001555 benzenes Chemical class 0.000 abstract description 4
- 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 abstract description 2
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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
- 238000012360 testing method Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 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
- 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
- 238000000034 method Methods 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000000047 product Substances 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
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 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
- 241000282320 Panthera leo Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali 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
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 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 true JPS60202155A (ja) | 1985-10-12 |
| JPH0421675B2 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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03195775A (ja) * | 1989-12-25 | 1991-08-27 | Yamamoto Chem Inc | 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 |
| US5220038A (en) * | 1989-07-19 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Fluoran compounds, crystalline toluene adducts thereof, recording material comprising same and process for their preparation |
| US5283222A (en) * | 1990-06-19 | 1994-02-01 | Mitsui Toatsu Chemicals, Inc. | Recording material comprising novel crystalline fluoran and process for prepartion of the said crystalline fluoran |
| 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
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5220038A (en) * | 1989-07-19 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Fluoran compounds, crystalline toluene adducts thereof, recording material comprising same and process for their preparation |
| US5324704A (en) * | 1989-07-19 | 1994-06-28 | Mitsui Toatsu Chemicals, Inc. | Fluoran compounds, crystalline toluene adducts thereof, recording material comprising same and process for their preparation |
| JPH03195775A (ja) * | 1989-12-25 | 1991-08-27 | Yamamoto Chem Inc | 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 |
| US5283222A (en) * | 1990-06-19 | 1994-02-01 | Mitsui Toatsu Chemicals, Inc. | Recording material comprising novel crystalline fluoran and process for prepartion of the said crystalline fluoran |
| US5955398A (en) * | 1997-04-25 | 1999-09-21 | Appleton Papers Inc. | Thermally-responsive record material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0421675B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |