FR2470766A1 - Produits d'addition dieniques de l'hexachlorocyclopentadiene sur des imides n-substitues d'acides dicarboxyliques insatures et leur procede de preparation - Google Patents
Produits d'addition dieniques de l'hexachlorocyclopentadiene sur des imides n-substitues d'acides dicarboxyliques insatures et leur procede de preparation Download PDFInfo
- Publication number
- FR2470766A1 FR2470766A1 FR7929881A FR7929881A FR2470766A1 FR 2470766 A1 FR2470766 A1 FR 2470766A1 FR 7929881 A FR7929881 A FR 7929881A FR 7929881 A FR7929881 A FR 7929881A FR 2470766 A1 FR2470766 A1 FR 2470766A1
- Authority
- FR
- France
- Prior art keywords
- hexachlorocyclopentadiene
- mole
- adducts
- dicarboxylic
- temperature
- 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
- 150000003949 imides Chemical class 0.000 title claims description 10
- 239000000178 monomer Substances 0.000 title abstract description 3
- 239000003063 flame retardant Substances 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 title 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001993 dienes Chemical class 0.000 claims abstract description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920000098 polyolefin Polymers 0.000 abstract description 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- -1 heterocyclic radical Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CNDOSNMFHUSKGN-UHFFFAOYSA-N 1-(2-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC=C1N1C(=O)C=CC1=O CNDOSNMFHUSKGN-UHFFFAOYSA-N 0.000 description 1
- YWODHBPFOGXUFX-UHFFFAOYSA-N 1-(3-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC(N2C(C=CC2=O)=O)=C1 YWODHBPFOGXUFX-UHFFFAOYSA-N 0.000 description 1
- WZLHPCMSXVTARD-UHFFFAOYSA-N 2-hex-4-enylpropanedioic acid Chemical compound C(CCCC=CC)(C(=O)O)C(=O)O WZLHPCMSXVTARD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7908453,A NL183137C (nl) | 1979-11-20 | 1979-11-20 | Werkwijze voor het bereiden van dieen-additieprodukten, alsmede op deze wijze bereide dieen-additieprodukten. |
| FR7929881A FR2470766A1 (fr) | 1979-11-20 | 1979-12-05 | Produits d'addition dieniques de l'hexachlorocyclopentadiene sur des imides n-substitues d'acides dicarboxyliques insatures et leur procede de preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7908453,A NL183137C (nl) | 1979-11-20 | 1979-11-20 | Werkwijze voor het bereiden van dieen-additieprodukten, alsmede op deze wijze bereide dieen-additieprodukten. |
| FR7929881A FR2470766A1 (fr) | 1979-11-20 | 1979-12-05 | Produits d'addition dieniques de l'hexachlorocyclopentadiene sur des imides n-substitues d'acides dicarboxyliques insatures et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2470766A1 true FR2470766A1 (fr) | 1981-06-12 |
| FR2470766B1 FR2470766B1 (enExample) | 1983-07-01 |
Family
ID=26221468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7929881A Granted FR2470766A1 (fr) | 1979-11-20 | 1979-12-05 | Produits d'addition dieniques de l'hexachlorocyclopentadiene sur des imides n-substitues d'acides dicarboxyliques insatures et leur procede de preparation |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2470766A1 (enExample) |
| NL (1) | NL183137C (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132547A1 (en) * | 1983-06-20 | 1985-02-13 | General Electric Company | Bisimides and method for their use in polyimide synthesis |
| EP0355435A3 (en) * | 1988-08-15 | 1991-05-29 | General Electric Company | Polycarbonate composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1418511A (fr) * | 1963-12-12 | 1965-11-19 | Universal Oil Prod Co | Procédé de préparation d'imides d'acides polyhalopolyhydroalcanonaphtalènedicarboxyliques, produits en résultant et leurs applications |
| US3455950A (en) * | 1967-07-28 | 1969-07-15 | Universal Oil Prod Co | N,n'-bis-imides of polyhalosubstituted polyhydropolycyclicdicarboxylic acids |
| US3549648A (en) * | 1968-07-01 | 1970-12-22 | Dow Chemical Co | Certain 1,2,3,4,9,9 - hexachloro - 1,4,4a,5,6,7,8,8a - octahydro - 1,4 - methanonaphthalene-6,7-dicarboximides |
| US3673149A (en) * | 1968-09-05 | 1972-06-27 | Universal Oil Prod Co | Flame retardant compositions of matter |
-
1979
- 1979-11-20 NL NLAANVRAGE7908453,A patent/NL183137C/xx not_active IP Right Cessation
- 1979-12-05 FR FR7929881A patent/FR2470766A1/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1418511A (fr) * | 1963-12-12 | 1965-11-19 | Universal Oil Prod Co | Procédé de préparation d'imides d'acides polyhalopolyhydroalcanonaphtalènedicarboxyliques, produits en résultant et leurs applications |
| US3455950A (en) * | 1967-07-28 | 1969-07-15 | Universal Oil Prod Co | N,n'-bis-imides of polyhalosubstituted polyhydropolycyclicdicarboxylic acids |
| US3549648A (en) * | 1968-07-01 | 1970-12-22 | Dow Chemical Co | Certain 1,2,3,4,9,9 - hexachloro - 1,4,4a,5,6,7,8,8a - octahydro - 1,4 - methanonaphthalene-6,7-dicarboximides |
| US3673149A (en) * | 1968-09-05 | 1972-06-27 | Universal Oil Prod Co | Flame retardant compositions of matter |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132547A1 (en) * | 1983-06-20 | 1985-02-13 | General Electric Company | Bisimides and method for their use in polyimide synthesis |
| EP0355435A3 (en) * | 1988-08-15 | 1991-05-29 | General Electric Company | Polycarbonate composition |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7908453A (nl) | 1981-06-16 |
| NL183137C (nl) | 1988-08-01 |
| NL183137B (nl) | 1988-03-01 |
| FR2470766B1 (enExample) | 1983-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |