JPH0477741B2 - - Google Patents
Info
- Publication number
- JPH0477741B2 JPH0477741B2 JP11355485A JP11355485A JPH0477741B2 JP H0477741 B2 JPH0477741 B2 JP H0477741B2 JP 11355485 A JP11355485 A JP 11355485A JP 11355485 A JP11355485 A JP 11355485A JP H0477741 B2 JPH0477741 B2 JP H0477741B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- compounds
- complex
- guest
- acid
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- IUQPYUUSZJYMFG-UHFFFAOYSA-N 5-carbamoylbenzene-1,2,4-tricarboxylic acid Chemical compound NC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O IUQPYUUSZJYMFG-UHFFFAOYSA-N 0.000 claims 1
- QHVJZYJNUUACLR-UHFFFAOYSA-N 5-carbamoylbenzene-1,3-dicarboxylic acid Chemical compound NC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QHVJZYJNUUACLR-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000000862 absorption spectrum Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- -1 diacetylene diols Chemical class 0.000 description 5
- MTINMIXBAVGBNY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n,5-n,5-n-hexacyclohexylbenzene-1,3,5-tricarboxamide Chemical compound C=1C(C(=O)N(C2CCCCC2)C2CCCCC2)=CC(C(=O)N(C2CCCCC2)C2CCCCC2)=CC=1C(=O)N(C1CCCCC1)C1CCCCC1 MTINMIXBAVGBNY-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- FNGBYWBFWZVPPV-UHFFFAOYSA-N benzene-1,2,4,5-tetracarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=C(C(Cl)=O)C=C1C(Cl)=O FNGBYWBFWZVPPV-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WXTPRAZNOXQAFY-UHFFFAOYSA-N 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C#CC#CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 WXTPRAZNOXQAFY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FTGCTVWKHSDTEQ-UHFFFAOYSA-N 2,5-bis(2,4-dimethylphenyl)benzene-1,4-diol Chemical compound CC1=CC(C)=CC=C1C1=CC(O)=C(C=2C(=CC(C)=CC=2)C)C=C1O FTGCTVWKHSDTEQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RYFIDGIWTNANMO-UHFFFAOYSA-N 9,10-diphenylanthracene-9,10-diol Chemical compound C12=CC=CC=C2C(O)(C=2C=CC=CC=2)C2=CC=CC=C2C1(O)C1=CC=CC=C1 RYFIDGIWTNANMO-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical group CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11355485A JPS61271267A (ja) | 1985-05-27 | 1985-05-27 | 新規ベンゼンポリカルボン酸ポリアミド |
| EP86103018A EP0198202B1 (en) | 1985-03-09 | 1986-03-07 | Novel n-cyclohexyl-polycarboxamide compound and derivatives thereof, processes for preparing them, and use of them in preparation of host-guest complexes |
| AT86103018T ATE65243T1 (de) | 1985-03-09 | 1986-03-07 | N-cyklohexyl-polycarboxamide verbindung und ihre derivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von acceptor-donor- komplexen. |
| DE8686103018T DE3680227D1 (de) | 1985-03-09 | 1986-03-07 | N-cyklohexyl-polycarboxamide verbindung und ihre derivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von acceptor-donor-komplexen. |
| US06/837,199 US4785111A (en) | 1985-03-09 | 1986-03-10 | N-cyclohexyl-polycarboxamide compound and derivatives thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11355485A JPS61271267A (ja) | 1985-05-27 | 1985-05-27 | 新規ベンゼンポリカルボン酸ポリアミド |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61271267A JPS61271267A (ja) | 1986-12-01 |
| JPH0477741B2 true JPH0477741B2 (enrdf_load_stackoverflow) | 1992-12-09 |
Family
ID=14615233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11355485A Granted JPS61271267A (ja) | 1985-03-09 | 1985-05-27 | 新規ベンゼンポリカルボン酸ポリアミド |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61271267A (enrdf_load_stackoverflow) |
-
1985
- 1985-05-27 JP JP11355485A patent/JPS61271267A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61271267A (ja) | 1986-12-01 |
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