CA1173598A - Process for the synthesis of polymers and copolymers based on vinyl chloroformate - Google Patents
Process for the synthesis of polymers and copolymers based on vinyl chloroformateInfo
- Publication number
- CA1173598A CA1173598A CA000370223A CA370223A CA1173598A CA 1173598 A CA1173598 A CA 1173598A CA 000370223 A CA000370223 A CA 000370223A CA 370223 A CA370223 A CA 370223A CA 1173598 A CA1173598 A CA 1173598A
- Authority
- CA
- Canada
- Prior art keywords
- vinyl
- chloroformate
- process according
- percarbonate
- molecular weight
- 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
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 229920001577 copolymer Polymers 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 5
- 229920000642 polymer Polymers 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims description 34
- 239000003999 initiator Substances 0.000 claims description 22
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 11
- 125000002348 vinylic group Chemical group 0.000 claims description 10
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000012780 transparent material Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 229940073584 methylene chloride Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229960005419 nitrogen Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- -1 vinyl chloroformate Vinyl chloroformate Chemical compound 0.000 description 3
- MTVWFVDWRVYDOR-UHFFFAOYSA-N 3,4-Dihydroxyphenylglycol Chemical compound OCC(O)C1=CC=C(O)C(O)=C1 MTVWFVDWRVYDOR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HOOWCUZPEFNHDT-UHFFFAOYSA-N DHPG Natural products OC(=O)C(N)C1=CC(O)=CC(O)=C1 HOOWCUZPEFNHDT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ULFHSQLFQYTZLS-UHFFFAOYSA-N difluoroamine Chemical compound FNF ULFHSQLFQYTZLS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017051 nitrogen difluoride Inorganic materials 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/24—Esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002651A FR2475558A1 (fr) | 1980-02-07 | 1980-02-07 | Procede de synthese de polymeres et de copolymeres a base de chloroformiate de vinyle |
| FR80.02651 | 1980-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173598A true CA1173598A (en) | 1984-08-28 |
Family
ID=9238306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000370223A Expired CA1173598A (en) | 1980-02-07 | 1981-02-05 | Process for the synthesis of polymers and copolymers based on vinyl chloroformate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4381385A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0034086B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56127606A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1173598A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3160617D1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2475558A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2682609B1 (fr) * | 1991-10-18 | 1994-01-07 | Centre Nal Recherc Scientifique | Support pour la preparation de colonnes chromatographiques et procede pour sa preparation. |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370588A (en) * | 1942-10-22 | 1945-02-27 | Pittsburgh Plate Glass Co | Organic percarbonates |
| US2377085A (en) * | 1943-09-29 | 1945-05-29 | Pittsburgh Plate Glass Co | Unsaturated chlorocarbonates and method of preparation |
| US2377035A (en) * | 1944-04-10 | 1945-05-29 | William I Pixley | Bearing mounting |
| US2476637A (en) * | 1947-02-28 | 1949-07-19 | Pittsburgh Plate Glass Co | Method of preparing chloroformates |
| US3022281A (en) * | 1958-11-24 | 1962-02-20 | Goodyear Tire & Rubber | Polymerization process with a peroxydicarbonate initiator formed in situ |
| US3022231A (en) * | 1959-07-27 | 1962-02-20 | Frank W Broderick | Method of producing matching embossing rolls |
| US3051686A (en) * | 1960-03-30 | 1962-08-28 | Pittsburgh Plate Glass Co | Polychloroformates |
| US3118862A (en) * | 1960-07-05 | 1964-01-21 | Du Pont | Copolymers of vinyl chloroformate, with acrylonitrile or vinyl acetate |
| US3254033A (en) * | 1961-09-27 | 1966-05-31 | Union Carbide Corp | Low temperature polymerization catalysts |
| DE1235591B (de) * | 1964-04-15 | 1967-03-02 | Hoechst Ag | Verfahren zur Polymerisation von Vinylestern |
| GB1107956A (en) * | 1966-02-28 | 1968-03-27 | Noury & Van Der Lande | Improvements in or relating to organic peroxydicarbonates |
| US3821273A (en) * | 1970-07-30 | 1974-06-28 | Pennwalt Corp | Novel dialkyl peroxydicarbonates |
| FR2381739A1 (fr) * | 1977-02-25 | 1978-09-22 | Poudres & Explosifs Ste Nale | Procede de synthese industrielle du chloroformiate de vinyle |
-
1980
- 1980-02-07 FR FR8002651A patent/FR2475558A1/fr active Granted
-
1981
- 1981-01-22 US US06/227,483 patent/US4381385A/en not_active Expired - Fee Related
- 1981-01-29 DE DE8181400131T patent/DE3160617D1/de not_active Expired
- 1981-01-29 EP EP81400131A patent/EP0034086B1/fr not_active Expired
- 1981-02-05 CA CA000370223A patent/CA1173598A/en not_active Expired
- 1981-02-06 JP JP1679781A patent/JPS56127606A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4381385A (en) | 1983-04-26 |
| JPS56127606A (en) | 1981-10-06 |
| DE3160617D1 (en) | 1983-08-25 |
| FR2475558B1 (cg-RX-API-DMAC7.html) | 1985-03-08 |
| FR2475558A1 (fr) | 1981-08-14 |
| EP0034086A1 (fr) | 1981-08-19 |
| EP0034086B1 (fr) | 1983-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4327201A (en) | Cationically polymerizable macromolecular monomers and graft copolymers therefrom | |
| Doi et al. | Radical copolymerization of N‐alkylmaleimides with isobutene and the properties of the resulting alternating copolymers | |
| JPH02281013A (ja) | ジケトン化合物系共重合体 | |
| EP0095086B1 (en) | Polymerizable, optically active polymer and process for preparing polymerizable polymer | |
| Asami et al. | Polymerization of macromers: 2. Group transfer polymerization of methacrylate-terminated polystyrene macromer | |
| Wang et al. | Anionic polymerization of acrylic monomers. 15. Living anionic copolymerization of mixtures of methyl methacrylate and tert-butyl acrylate as promoted by dibenzo-18-crown-6 | |
| CA1173598A (en) | Process for the synthesis of polymers and copolymers based on vinyl chloroformate | |
| Ishizone et al. | Anionic polymerization of monomers containing functional groups, 11. Anionic polymerizations of alkynyl methacrylates | |
| Komiyama et al. | Polymerization of coordinated monomers. X. Kinetic study of alternating copolymerization of methyl methacrylate and styrene with stannic chloride in dichloroethane | |
| US5399641A (en) | Method of controlling the polymerization of acrylates | |
| Van Kerckhoven et al. | Dithiocarbamate telechelic polymers: Synthesis and block copolymerization | |
| US5082910A (en) | Polymerization process using tertiary-amylperoxy pivalate as the free radical initiator | |
| Yamada et al. | Preparation and polymerization behavior of 2‐[2, 2, 2‐tris‐(alkoxycarbonyl) ethyl] acrylic ester as a sterically congested monomer | |
| Matsumoto et al. | Synthesis of substituted polymethylenes by radical polymerization of N, N, N′, N′‐tetraalkylfumaramides and their characterization | |
| Otsu et al. | Monomer‐isomerization radical polymerization of di‐tert‐butyl maleate and preparation of poly (fumaric acid) via pyrolysis | |
| US6258905B1 (en) | Stabilized, unimolecular initiators for hydrocarbon polymerization | |
| US5302680A (en) | Copolymers of epoxybutadiene and maleimides | |
| Tanabe et al. | Maximization of the molecular weight of poly [alkyl (meth) acrylate] using SmMe (C5Me5) 2 (THF) as an initiator | |
| Iwatsuki et al. | Radical polymerization behavior of 7, 8-bis (ethylthio)-and 7, 8-bis (phenylthio)-7, 8-dicyanoquinodimethanes | |
| Meunier et al. | Polymerization and copolymerization of vinyl carbamates and vinyl carbonates | |
| JPH04134090A (ja) | ホスファゼン誘導体及びその重合体 | |
| Tharanikkarasu et al. | ‘Living’Radical Polymerization of Styrene Using Tetraphenylethane‐based Polyurethane Iniferter | |
| Davis et al. | Synthesis of high refractive index acrylic copolymers | |
| Meunier et al. | Poly (vinyl chloroformate) and derivatives: 2. Copolymerization of vinyl chloroformate and of phenyl vinyl carbonate with vinyl monomers | |
| US3524838A (en) | Novel polymerization method of vinyl compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |