DE2242005C2 - Verfahren zur Herstellung von Fluoranderivaten - Google Patents
Verfahren zur Herstellung von FluoranderivatenInfo
- Publication number
- DE2242005C2 DE2242005C2 DE2242005A DE2242005A DE2242005C2 DE 2242005 C2 DE2242005 C2 DE 2242005C2 DE 2242005 A DE2242005 A DE 2242005A DE 2242005 A DE2242005 A DE 2242005A DE 2242005 C2 DE2242005 C2 DE 2242005C2
- Authority
- DE
- Germany
- Prior art keywords
- hours
- reaction
- benzophenone
- sulfuric acid
- phenol
- 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
- 238000000034 method Methods 0.000 title description 7
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 title description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 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 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- -1 phenolic amine Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
-
- 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
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17629671A | 1971-08-30 | 1971-08-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2242005A1 DE2242005A1 (de) | 1973-03-15 |
| DE2242005C2 true DE2242005C2 (de) | 1984-05-10 |
Family
ID=22643782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2242005A Expired DE2242005C2 (de) | 1971-08-30 | 1972-08-26 | Verfahren zur Herstellung von Fluoranderivaten |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5638619B2 (enExample) |
| AT (1) | AT315825B (enExample) |
| AU (1) | AU454455B2 (enExample) |
| BE (1) | BE788073A (enExample) |
| CA (1) | CA968361A (enExample) |
| CH (1) | CH596214A5 (enExample) |
| DE (1) | DE2242005C2 (enExample) |
| DK (1) | DK143654C (enExample) |
| ES (1) | ES406170A1 (enExample) |
| FR (1) | FR2150854B1 (enExample) |
| GB (1) | GB1338851A (enExample) |
| IT (1) | IT964084B (enExample) |
| NL (1) | NL175190C (enExample) |
| SE (1) | SE386678B (enExample) |
| ZA (1) | ZA725407B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5119411B1 (enExample) * | 1971-03-25 | 1976-06-17 | ||
| JPS5120330B2 (enExample) * | 1972-07-15 | 1976-06-24 | ||
| JPS6025275B2 (ja) * | 1977-06-13 | 1985-06-17 | 山田化学工業株式会社 | 感熱記録材料 |
| JPS55123651A (en) * | 1979-03-19 | 1980-09-24 | Mitsubishi Paper Mills Ltd | Preparation of fluoran compound |
| US4414399A (en) | 1979-05-14 | 1983-11-08 | Sterling Drug Inc. | 5/6 Carboxyphthalides |
| US4515971A (en) * | 1980-03-31 | 1985-05-07 | Hilton-Davis Chemical Co. | 5'/6'-Carboxyfluorans and derivatives thereof |
| JPS6053069B2 (ja) * | 1980-09-17 | 1985-11-22 | 保土谷化学工業株式会社 | フルオラン化合物 |
| EP0176161A1 (en) * | 1984-08-24 | 1986-04-02 | Taoka Chemical Co., Ltd | Novel fluoran compounds and production and use thereof |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE34290B1 (en) * | 1969-05-22 | 1975-04-02 | Fuji Photo Film Co Ltd | Process for preparation of fluoran compounds |
-
1972
- 1972-06-16 CA CA144,963A patent/CA968361A/en not_active Expired
- 1972-08-07 ZA ZA725407A patent/ZA725407B/xx unknown
- 1972-08-10 AU AU45455/72A patent/AU454455B2/en not_active Expired
- 1972-08-16 GB GB3813372A patent/GB1338851A/en not_active Expired
- 1972-08-18 IT IT28301/72A patent/IT964084B/it active
- 1972-08-18 JP JP8266872A patent/JPS5638619B2/ja not_active Expired
- 1972-08-22 ES ES406170A patent/ES406170A1/es not_active Expired
- 1972-08-25 FR FR727230272A patent/FR2150854B1/fr not_active Expired
- 1972-08-25 NL NLAANVRAGE7211650,A patent/NL175190C/xx not_active IP Right Cessation
- 1972-08-26 DE DE2242005A patent/DE2242005C2/de not_active Expired
- 1972-08-28 SE SE7211109A patent/SE386678B/xx unknown
- 1972-08-28 BE BE788073A patent/BE788073A/xx not_active IP Right Cessation
- 1972-08-29 DK DK426272A patent/DK143654C/da not_active IP Right Cessation
- 1972-08-30 CH CH1277672A patent/CH596214A5/xx not_active IP Right Cessation
- 1972-08-30 AT AT745172A patent/AT315825B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2150854A1 (enExample) | 1973-04-13 |
| IT964084B (it) | 1974-01-21 |
| AU4545572A (en) | 1974-02-14 |
| NL7211650A (enExample) | 1973-03-02 |
| JPS4834932A (enExample) | 1973-05-23 |
| AT315825B (de) | 1974-06-10 |
| CH596214A5 (enExample) | 1978-03-15 |
| GB1338851A (en) | 1973-11-28 |
| NL175190C (nl) | 1984-10-01 |
| FR2150854B1 (enExample) | 1979-02-09 |
| ZA725407B (en) | 1973-04-25 |
| CA968361A (en) | 1975-05-27 |
| ES406170A1 (es) | 1975-09-16 |
| DK143654B (da) | 1981-09-21 |
| DE2242005A1 (de) | 1973-03-15 |
| SE386678B (sv) | 1976-08-16 |
| DK143654C (da) | 1982-03-08 |
| BE788073A (fr) | 1972-12-18 |
| AU454455B2 (en) | 1974-10-31 |
| NL175190B (nl) | 1984-05-01 |
| JPS5638619B2 (enExample) | 1981-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OB | Request for examination as to novelty | ||
| OC | Search report available | ||
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: APPLETON PAPERS INC., APPLETON, WIS., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: WEICKMANN, H., DIPL.-ING. FINCKE, K., DIPL.-PHYS. DR. WEICKMANN, F., DIPL.-ING. HUBER, B., DIPL.-CHEM. LISKA, H., DIPL.-ING. DR.-ING. PRECHTEL, J., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |