DE2161861C3 - Kontinuierliches Verfahren zur Herstellung eines Vinylidenfluorid-Copolymeren - Google Patents
Kontinuierliches Verfahren zur Herstellung eines Vinylidenfluorid-CopolymerenInfo
- Publication number
- DE2161861C3 DE2161861C3 DE2161861A DE2161861A DE2161861C3 DE 2161861 C3 DE2161861 C3 DE 2161861C3 DE 2161861 A DE2161861 A DE 2161861A DE 2161861 A DE2161861 A DE 2161861A DE 2161861 C3 DE2161861 C3 DE 2161861C3
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- period
- time
- reaction zone
- residence time
- 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
- 229920001577 copolymer Polymers 0.000 title claims description 93
- 238000010924 continuous production Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 9
- 238000000034 method Methods 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000004816 latex Substances 0.000 claims description 31
- 229920000126 latex Polymers 0.000 claims description 31
- 239000012986 chain transfer agent Substances 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- 238000012546 transfer Methods 0.000 claims description 13
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000009826 distribution Methods 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 7
- 238000011068 loading method Methods 0.000 claims description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 3
- 239000011872 intimate mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 18
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 chlorotrifluoroethylene, dichlorodifluoroethylene, chlorofluoroethylene, Trifluoropropene Chemical class 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- SXKNYNUXUHCUHX-UHFFFAOYSA-N 1,1,2,3,3,4-hexafluorobut-1-ene Chemical compound FCC(F)(F)C(F)=C(F)F SXKNYNUXUHCUHX-UHFFFAOYSA-N 0.000 description 1
- DVMSVWIURPPRBC-UHFFFAOYSA-N 2,3,3-trifluoroprop-2-enoic acid Chemical class OC(=O)C(F)=C(F)F DVMSVWIURPPRBC-UHFFFAOYSA-N 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 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 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SPEMQUPJTGQFIM-UHFFFAOYSA-N triazanium;hydrogen sulfite;sulfite Chemical compound [NH4+].[NH4+].[NH4+].OS([O-])=O.[O-]S([O-])=O SPEMQUPJTGQFIM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
- C08F214/00—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
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9804470A | 1970-12-14 | 1970-12-14 | |
| US00197512A US3839305A (en) | 1970-12-14 | 1971-11-10 | Method of making vinylidene fluoride copolymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2161861A1 DE2161861A1 (de) | 1972-06-29 |
| DE2161861B2 DE2161861B2 (de) | 1980-04-10 |
| DE2161861C3 true DE2161861C3 (de) | 1980-12-18 |
Family
ID=26793987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2161861A Expired DE2161861C3 (de) | 1970-12-14 | 1971-12-13 | Kontinuierliches Verfahren zur Herstellung eines Vinylidenfluorid-Copolymeren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3839305A (enExample) |
| JP (1) | JPS5124554B1 (enExample) |
| CA (1) | CA932100A (enExample) |
| DE (1) | DE2161861C3 (enExample) |
| FR (1) | FR2118547A5 (enExample) |
| GB (1) | GB1357767A (enExample) |
| IT (1) | IT946136B (enExample) |
| NL (1) | NL148909B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845024A (en) * | 1972-11-22 | 1974-10-29 | Du Pont | Continuous process for production of fluoroelastomers |
| US4484894A (en) * | 1980-09-03 | 1984-11-27 | Eiichi Masuhara | Sheet for lining denture base |
| US4360652A (en) * | 1981-08-31 | 1982-11-23 | Pennwalt Corporation | Method of preparing high quality vinylidene fluoride polymer in aqueous emulsion |
| US4524197A (en) * | 1984-08-28 | 1985-06-18 | E. I. Du Pont De Nemours And Company | Process for making vinylidene fluoride containing fluoroelastomers |
| CA1244196A (en) * | 1984-12-26 | 1988-11-01 | Yoshinori Masuda | High molecular weight fluoroelastomer |
| US4985520A (en) * | 1988-07-29 | 1991-01-15 | Asahi Kasei Kogyo Kabushiki Kaisha | Fluoroelastomer having excellent processability |
| DE69207105T2 (de) * | 1991-08-01 | 1996-05-15 | Kureha Chemical Industry Co., Ltd., Tokio/Tokyo | Verfahren zur Herstellung von Vinylidene-Fluoride-Polymer |
| AT397353B (de) * | 1991-08-28 | 1994-03-25 | Tyrolia Freizeitgeraete | Vorderbacken |
| EP0911347B1 (en) | 1997-10-15 | 2006-08-23 | E.I. Du Pont De Nemours And Company | Copolymers of maleic anhydride or acid and fluorinated olefins |
| US6489420B1 (en) * | 2000-06-27 | 2002-12-03 | Dyneon Llc | Fluoropolymers with improved characteristics |
| CA2446016A1 (en) | 2001-05-02 | 2002-11-07 | 3M Innovative Properties Company | Emulsifier free aqueous emulsion polymerization process for making fluoropolymers |
| US6646077B1 (en) * | 2002-07-11 | 2003-11-11 | Dupont Dow Elastomers Llc | Peroxide curable fluoroelastomers |
| FR2842203A1 (fr) * | 2002-07-12 | 2004-01-16 | Atofina | Procede de fabrication du polymere du fluorure de vinylidene |
| US20050124773A1 (en) * | 2003-12-09 | 2005-06-09 | Tang Phan L. | Extrudable fluoroelastomer composition |
| FR2944285B1 (fr) | 2009-04-09 | 2011-11-25 | Francois Bauer | Procede de fabrication de terpolymeres a base de vdf, trfe et cfe ou ctfe |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA676648A (en) * | 1963-12-24 | E.I. Du Pont De Nemours And Company | Copolymers of hexafluoropropylene vinylidene fluoride and aliphatic chain transfer agents | |
| CA621540A (en) * | 1961-06-06 | S. Rugg John | Elastomers | |
| CA767754A (en) * | 1967-09-19 | Sianesi Dario | Thermoplastic and elastomeric copolymers containing fluorine | |
| US3069401A (en) * | 1960-02-23 | 1962-12-18 | Du Pont | Copolymers of hexafluoropropylene vinylidene fluoride and aliphatic, chain transfer agents |
| US3467636A (en) * | 1967-02-24 | 1969-09-16 | Du Pont | Redox catalyst system for preparing vinylidene fluoride interpolymers |
| US3547857A (en) * | 1967-10-16 | 1970-12-15 | Uniroyal Inc | Continuous emulsion polymerization of styrene and acrylonitrile by addition of monomers in plural stages with all of emulsifier added in first stage |
| US3560454A (en) * | 1967-12-20 | 1971-02-02 | Dynamit Nobel Ag | Process for the continuous polymerization and copolymerization of ethylenically unsaturated compounds |
| US3472829A (en) * | 1968-06-10 | 1969-10-14 | Exxon Research Engineering Co | Process for broadening the molecular weight distribution in polymers |
| US3634369A (en) * | 1970-04-09 | 1972-01-11 | Dow Chemical Co | Vinylidene chloride polymers of broadened molecular weight distribution |
-
1971
- 1971-11-10 US US00197512A patent/US3839305A/en not_active Expired - Lifetime
- 1971-12-09 CA CA129801A patent/CA932100A/en not_active Expired
- 1971-12-11 IT IT32281/71A patent/IT946136B/it active
- 1971-12-13 JP JP46100268A patent/JPS5124554B1/ja active Pending
- 1971-12-13 FR FR7144675A patent/FR2118547A5/fr not_active Expired
- 1971-12-13 DE DE2161861A patent/DE2161861C3/de not_active Expired
- 1971-12-14 GB GB5804571A patent/GB1357767A/en not_active Expired
- 1971-12-14 NL NL717117135A patent/NL148909B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2161861A1 (de) | 1972-06-29 |
| JPS5124554B1 (enExample) | 1976-07-24 |
| CA932100A (en) | 1973-08-14 |
| DE2161861B2 (de) | 1980-04-10 |
| FR2118547A5 (enExample) | 1972-07-28 |
| IT946136B (it) | 1973-05-21 |
| US3839305A (en) | 1974-10-01 |
| NL148909B (nl) | 1976-03-15 |
| NL7117135A (enExample) | 1972-06-16 |
| GB1357767A (en) | 1974-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |