CA1079286A - Process for preparing bisimides and bisimides prepared thereby - Google Patents
Process for preparing bisimides and bisimides prepared therebyInfo
- Publication number
- CA1079286A CA1079286A CA272,333A CA272333A CA1079286A CA 1079286 A CA1079286 A CA 1079286A CA 272333 A CA272333 A CA 272333A CA 1079286 A CA1079286 A CA 1079286A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- boiling point
- acid
- solvent mixture
- mixture
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 21
- 238000009835 boiling Methods 0.000 claims abstract description 18
- 239000011877 solvent mixture Substances 0.000 claims abstract description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000008096 xylene Substances 0.000 claims abstract description 9
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 6
- 150000005826 halohydrocarbons Chemical class 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 5
- 230000005593 dissociations Effects 0.000 claims abstract description 5
- 150000003738 xylenes Chemical class 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical group NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical group NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical group CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101150009724 CYBA gene Proteins 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical class BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 mèsitylene Chemical compound 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical class CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69302776A | 1976-06-04 | 1976-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079286A true CA1079286A (en) | 1980-06-10 |
Family
ID=24783016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,333A Expired CA1079286A (en) | 1976-06-04 | 1977-02-22 | Process for preparing bisimides and bisimides prepared thereby |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4125535A (en:Method) |
| JP (1) | JPS52148068A (en:Method) |
| AU (1) | AU503557B2 (en:Method) |
| BE (1) | BE852708A (en:Method) |
| CA (1) | CA1079286A (en:Method) |
| DE (1) | DE2708469C3 (en:Method) |
| FR (1) | FR2353532A1 (en:Method) |
| GB (1) | GB1519133A (en:Method) |
| IT (1) | IT1072663B (en:Method) |
| NL (1) | NL7702890A (en:Method) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2400014A1 (fr) * | 1977-08-09 | 1979-03-09 | Rhone Poulenc Ind | Preparation d'oligoimides |
| FR2444667A2 (fr) * | 1978-12-19 | 1980-07-18 | Rhone Poulenc Ind | Preparation d'oligoimides |
| US4515964A (en) * | 1982-01-07 | 1985-05-07 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates |
| US4414396A (en) * | 1982-01-07 | 1983-11-08 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates and haloformates |
| US4666958A (en) * | 1982-01-07 | 1987-05-19 | Ppg Industries, Inc. | Polymeric compositions containing polyhalophthalimidoalkyl-functional carbonates |
| US5049601A (en) * | 1988-02-01 | 1991-09-17 | Ethyl Corporation | Halogenated bis-imide flame retardants |
| US4871863A (en) * | 1988-02-01 | 1989-10-03 | Ethyl Corporation | Halogenated bis-imide flame retardants |
| JPH01199944A (ja) * | 1988-02-03 | 1989-08-11 | Dai Ichi Kogyo Seiyaku Co Ltd | 含ハロゲン化合物の製造方法、及びその化合物からなる難燃剤 |
| US4999391A (en) * | 1988-03-25 | 1991-03-12 | Atochem North America, Inc. | Halogen substituted phthalimide flame retardants |
| US4914212A (en) * | 1988-06-23 | 1990-04-03 | Ethyl Corporation | Process for preparing flame retardant bisimide product |
| US5136047A (en) * | 1988-06-23 | 1992-08-04 | Ethyl Corporation | Process for preparing flame retardant bisimide product |
| US4873341A (en) * | 1988-09-19 | 1989-10-10 | Ethyl Corporation | White bis-imide flame retardants |
| US4990626A (en) * | 1989-04-04 | 1991-02-05 | Ethyl Corporation | Process for preparing bisimides products |
| US4992557A (en) * | 1989-04-04 | 1991-02-12 | Ethyl Corporation | Process for preparing bisimide products |
| US5290945A (en) * | 1990-03-23 | 1994-03-01 | Ethyl Corporation | Process for preparing bisimide products |
| US5317048A (en) * | 1992-09-30 | 1994-05-31 | Great Lakes Chemical Corporation | Ultra white N,N'-ethylene-bis(tetrabromophthalimide) and its production in acetic acid |
| WO1994013638A1 (en) * | 1992-12-04 | 1994-06-23 | Albemarle Corporation | Process for preparing bisimide products |
| US5302723A (en) * | 1993-10-04 | 1994-04-12 | Monsanto Company | Process for preparing flame retardant bisimide compositions |
| US5393887A (en) * | 1993-10-04 | 1995-02-28 | Monsanto Company | Bisimide compositions |
| US6277905B1 (en) | 1999-09-23 | 2001-08-21 | Eastman Chemical Company | Process for improving the toughness of PCT formulations by adding rubber impact modifiers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051724A (en) * | 1961-02-03 | 1962-08-28 | Standard Oil Co | Novel bis(trimellit-imide) alkanes and bis(trimellit-amide) alkanes |
| US3873567A (en) * | 1968-09-05 | 1975-03-25 | Universal Oil Prod Co | N-substituted polybromoaromatic ortho-dicarboximides |
| US3868388A (en) * | 1972-10-20 | 1975-02-25 | Cities Service Co | Flame-retardant composition |
-
1977
- 1977-02-07 US US05/766,098 patent/US4125535A/en not_active Expired - Lifetime
- 1977-02-22 CA CA272,333A patent/CA1079286A/en not_active Expired
- 1977-02-23 AU AU22565/77A patent/AU503557B2/en not_active Expired
- 1977-02-26 DE DE2708469A patent/DE2708469C3/de not_active Expired
- 1977-03-03 JP JP2225377A patent/JPS52148068A/ja active Pending
- 1977-03-17 NL NL7702890A patent/NL7702890A/xx not_active Application Discontinuation
- 1977-03-21 BE BE175979A patent/BE852708A/xx not_active IP Right Cessation
- 1977-04-04 GB GB14162/77A patent/GB1519133A/en not_active Expired
- 1977-04-21 IT IT67901/77A patent/IT1072663B/it active
- 1977-05-03 FR FR7713431A patent/FR2353532A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2353532B1 (en:Method) | 1982-05-07 |
| DE2708469B2 (de) | 1980-01-24 |
| AU503557B2 (en) | 1979-09-06 |
| US4125535A (en) | 1978-11-14 |
| AU2256577A (en) | 1978-08-31 |
| DE2708469A1 (de) | 1977-12-08 |
| GB1519133A (en) | 1978-07-26 |
| NL7702890A (nl) | 1977-12-06 |
| IT1072663B (it) | 1985-04-10 |
| DE2708469C3 (de) | 1980-10-23 |
| JPS52148068A (en) | 1977-12-08 |
| BE852708A (fr) | 1977-07-18 |
| FR2353532A1 (fr) | 1977-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |