DE2229607A1 - Verfahren zur herstellung von thermoplastisch verarbeitbaren fluorolefin-polymerisaten - Google Patents
Verfahren zur herstellung von thermoplastisch verarbeitbaren fluorolefin-polymerisatenInfo
- Publication number
- DE2229607A1 DE2229607A1 DE2229607A DE2229607A DE2229607A1 DE 2229607 A1 DE2229607 A1 DE 2229607A1 DE 2229607 A DE2229607 A DE 2229607A DE 2229607 A DE2229607 A DE 2229607A DE 2229607 A1 DE2229607 A1 DE 2229607A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- regulator
- regulators
- weight
- fluorine
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229920001169 thermoplastic Polymers 0.000 title description 5
- 239000004416 thermosoftening plastic Substances 0.000 title description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 20
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- -1 vinyl olefins Chemical class 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229920001291 polyvinyl halide Polymers 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 15
- 239000003999 initiator Substances 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- QRKKTXWUDLJYCV-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)(Cl)C(=O)C(F)(F)Cl QRKKTXWUDLJYCV-UHFFFAOYSA-N 0.000 description 1
- QHSDHTYAVHZAHF-UHFFFAOYSA-N 1-(2-hydroxy-3,3-dimethylbutyl)peroxy-3,3-dimethylbutan-2-ol Chemical compound CC(C)(C)C(O)COOCC(O)C(C)(C)C QHSDHTYAVHZAHF-UHFFFAOYSA-N 0.000 description 1
- 108700030378 4-(3-(biotinylaminohexamethylenaminocarbonyl)propanoylaminomethyl)-2-methyl-1,3-dithiolane-2-yl-(Ala(7))phalloidin Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XZRULFCZVOUHQJ-UHFFFAOYSA-N bhpp Chemical compound N1C(=O)C(NC(=O)C(C)NC(=O)C2CC(O)CN2C2=O)CC(C3=CC=CC=C3N3)=C3SCC2NC(=O)C(C(O)C)NC(=O)C(C)NC(=O)C1CC1(C)SC(CNC(=O)CCC(=O)NCCCCCCNC(=O)CCCCC2C3NC(=O)NC3CS2)CS1 XZRULFCZVOUHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F14/00—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 a halogen
- C08F14/18—Monomers containing fluorine
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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)
- Polymerisation Methods In General (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2229607A DE2229607A1 (de) | 1972-06-19 | 1972-06-19 | Verfahren zur herstellung von thermoplastisch verarbeitbaren fluorolefin-polymerisaten |
| US05/367,902 US3937690A (en) | 1972-06-19 | 1973-06-07 | Process for the preparation of thermoplastically workable fluoro-olefin polymers |
| CH861773A CH587292A5 (enExample) | 1972-06-19 | 1973-06-14 | |
| BE132325A BE800982A (fr) | 1972-06-19 | 1973-06-15 | Procede de fabrication de polymeres fluoroolefiniques aptes au formage thermoplastique |
| IT50823/73A IT985700B (it) | 1972-06-19 | 1973-06-15 | Procedimento per la produzione di polimeri fluoroolefinici lavorabi li termoplasticamente |
| GB2891173A GB1416402A (en) | 1972-06-19 | 1973-06-18 | Preparation of fluorine-containing polymers |
| JP48068618A JPS4962579A (enExample) | 1972-06-19 | 1973-06-18 | |
| FR7322153A FR2189432B1 (enExample) | 1972-06-19 | 1973-06-18 | |
| NL7308509A NL7308509A (enExample) | 1972-06-19 | 1973-06-19 | |
| US05/588,081 US4000356A (en) | 1972-06-19 | 1975-06-18 | Process for the preparation of thermoplastically workable fluoro-olefin polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2229607A DE2229607A1 (de) | 1972-06-19 | 1972-06-19 | Verfahren zur herstellung von thermoplastisch verarbeitbaren fluorolefin-polymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2229607A1 true DE2229607A1 (de) | 1974-01-17 |
Family
ID=5848006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2229607A Ceased DE2229607A1 (de) | 1972-06-19 | 1972-06-19 | Verfahren zur herstellung von thermoplastisch verarbeitbaren fluorolefin-polymerisaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3937690A (enExample) |
| JP (1) | JPS4962579A (enExample) |
| BE (1) | BE800982A (enExample) |
| CH (1) | CH587292A5 (enExample) |
| DE (1) | DE2229607A1 (enExample) |
| FR (1) | FR2189432B1 (enExample) |
| GB (1) | GB1416402A (enExample) |
| IT (1) | IT985700B (enExample) |
| NL (1) | NL7308509A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815187A1 (de) * | 1977-04-08 | 1978-10-19 | Daikin Ind Ltd | Fluor enthaltendes polymer und verfahren zu seiner herstellung |
| DE3710818A1 (de) * | 1986-04-01 | 1987-10-08 | Nippon Mektron Kk | Verfahren zur herstellung von mittels peroxid vulkanisierbaren, fluor enthaltenden elastomeren |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5550051A (en) * | 1978-10-07 | 1980-04-11 | Daikin Ind Ltd | Blend composition for cocrosslinking of new fluoroelastomer |
| JPS5920310A (ja) * | 1982-07-27 | 1984-02-02 | Daikin Ind Ltd | 含フッ素ポリマー硬化用組成物 |
| JPS6052173B2 (ja) * | 1984-06-25 | 1985-11-18 | ダイキン工業株式会社 | 硬化容易な含フツ素ポリマ−の硬化用組成物 |
| US4581418A (en) * | 1984-08-23 | 1986-04-08 | The Dow Chemical Company | Process for preparing copolymer polyols |
| JPS63308008A (ja) * | 1986-04-01 | 1988-12-15 | Nippon Mektron Ltd | パ−オキサイド加硫可能な含フツ素エラストマ−の製造方法 |
| US4973633A (en) * | 1989-05-15 | 1990-11-27 | E. I. Du Pont De Nemours And Company | Peroxide-curable fluoroelastomers having bromine an iodine curesites and the preparation thereof |
| IT1265223B1 (it) * | 1993-11-25 | 1996-10-31 | Ausimont Spa | Processo per la preparazione di polimeri del vinilidenfluoruro |
| US5898054A (en) * | 1996-11-29 | 1999-04-27 | Nippon Mektron, Limited | Process for producing fluorine-containing elastomer |
| US6803435B2 (en) | 2002-07-18 | 2004-10-12 | 3M Innovative Properties Company | Curable fluoropolymers containing bromine groups having improved compression set |
| US6734254B1 (en) | 2003-01-13 | 2004-05-11 | 3M Innovative Properties Company | Co-curable blends featuring bromine-and iodine-containing fluoroplastic polymers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3019215A (en) * | 1955-05-14 | 1962-01-30 | Basf Ag | Production of telomers from ethylenically unsaturated compounds |
| GB883850A (en) * | 1960-09-23 | 1961-12-06 | Dow Chemical Co | Process for controlling the molecular weight of vinylidene chloride polymers |
-
1972
- 1972-06-19 DE DE2229607A patent/DE2229607A1/de not_active Ceased
-
1973
- 1973-06-07 US US05/367,902 patent/US3937690A/en not_active Expired - Lifetime
- 1973-06-14 CH CH861773A patent/CH587292A5/xx not_active IP Right Cessation
- 1973-06-15 IT IT50823/73A patent/IT985700B/it active
- 1973-06-15 BE BE132325A patent/BE800982A/xx unknown
- 1973-06-18 JP JP48068618A patent/JPS4962579A/ja active Pending
- 1973-06-18 GB GB2891173A patent/GB1416402A/en not_active Expired
- 1973-06-18 FR FR7322153A patent/FR2189432B1/fr not_active Expired
- 1973-06-19 NL NL7308509A patent/NL7308509A/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815187A1 (de) * | 1977-04-08 | 1978-10-19 | Daikin Ind Ltd | Fluor enthaltendes polymer und verfahren zu seiner herstellung |
| DE3710818A1 (de) * | 1986-04-01 | 1987-10-08 | Nippon Mektron Kk | Verfahren zur herstellung von mittels peroxid vulkanisierbaren, fluor enthaltenden elastomeren |
| DE3710818C2 (de) * | 1986-04-01 | 1993-10-21 | Nippon Mektron Kk | Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren |
Also Published As
| Publication number | Publication date |
|---|---|
| IT985700B (it) | 1974-12-10 |
| NL7308509A (enExample) | 1973-12-21 |
| FR2189432A1 (enExample) | 1974-01-25 |
| BE800982A (fr) | 1973-10-01 |
| FR2189432B1 (enExample) | 1976-07-23 |
| GB1416402A (en) | 1975-12-03 |
| CH587292A5 (enExample) | 1977-04-29 |
| US3937690A (en) | 1976-02-10 |
| JPS4962579A (enExample) | 1974-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |