DE3524370A1 - Verfahren zur herstellung eines formkoerpers aus vernetztem, fluorhaltigem pfropfcopolymerem unter anwendung von strahlung - Google Patents
Verfahren zur herstellung eines formkoerpers aus vernetztem, fluorhaltigem pfropfcopolymerem unter anwendung von strahlungInfo
- Publication number
- DE3524370A1 DE3524370A1 DE19853524370 DE3524370A DE3524370A1 DE 3524370 A1 DE3524370 A1 DE 3524370A1 DE 19853524370 DE19853524370 DE 19853524370 DE 3524370 A DE3524370 A DE 3524370A DE 3524370 A1 DE3524370 A1 DE 3524370A1
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- copolymers
- copolymer
- dipl
- tetrafluoroethylene
- 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
- 230000005855 radiation Effects 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 Polypropylene Polymers 0.000 title description 6
- 239000004743 Polypropylene Substances 0.000 title 1
- 229920001155 polypropylene Polymers 0.000 title 1
- 229920000578 graft copolymer Polymers 0.000 claims description 40
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- 239000011737 fluorine Substances 0.000 claims description 31
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 238000007334 copolymerization reaction Methods 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 13
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 13
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 10
- 230000005865 ionizing radiation Effects 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 229920001198 elastomeric copolymer Polymers 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 claims description 4
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- NACXPGJRIJFGLA-BQYQJAHWSA-N bis[(2-methylpropan-2-yl)oxy] (e)-but-2-enediperoxoate Chemical compound CC(C)(C)OOOC(=O)\C=C\C(=O)OOOC(C)(C)C NACXPGJRIJFGLA-BQYQJAHWSA-N 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 229930004008 p-menthane Natural products 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- ZUHAKVLHBJLXGV-UHFFFAOYSA-N tert-butyl 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOC(C)(C)C ZUHAKVLHBJLXGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- CXOHVCKJGLFRKZ-AATRIKPKSA-N tert-butyl (e)-but-2-eneperoxoate Chemical compound C\C=C\C(=O)OOC(C)(C)C CXOHVCKJGLFRKZ-AATRIKPKSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 9
- 229920001973 fluoroelastomer Polymers 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 229920006027 ternary co-polymer Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- TVFDJXOCXUVLDH-RNFDNDRNSA-N cesium-137 Chemical compound [137Cs] TVFDJXOCXUVLDH-RNFDNDRNSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- DNNSSWSSYDEUBZ-OUBTZVSYSA-N krypton-85 Chemical compound [85Kr] DNNSSWSSYDEUBZ-OUBTZVSYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 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
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IGDRZPVGFXXWAU-UHFFFAOYSA-N tert-butyl hydroperoxy carbonate Chemical compound C(OC(C)(C)C)(OOO)=O IGDRZPVGFXXWAU-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000009736 wetting 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
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14219684A JPS6123638A (ja) | 1984-07-11 | 1984-07-11 | 含ふつ素樹脂架橋体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3524370A1 true DE3524370A1 (de) | 1986-01-16 |
| DE3524370C2 DE3524370C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-20 |
Family
ID=15309621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853524370 Granted DE3524370A1 (de) | 1984-07-11 | 1985-07-08 | Verfahren zur herstellung eines formkoerpers aus vernetztem, fluorhaltigem pfropfcopolymerem unter anwendung von strahlung |
Country Status (6)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434362A1 (en) * | 1989-12-19 | 1991-06-26 | Tomei Sangyo Kabushiki Kaisha | Graft copolymer, solution containing the graft copolymer, and method of treating contact lens with the solution |
| WO1994017114A1 (de) * | 1993-01-29 | 1994-08-04 | Wacker-Chemie Gmbh | Pfropf- und core-shell-copolymerisate mit verbesserter phasenanbindung zwischen pfropfgrundlage und aufgepfropfter polymerphase |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0788414B2 (ja) * | 1987-08-10 | 1995-09-27 | セントラル硝子株式会社 | 軟質ふっ素樹脂の製造方法 |
| JPH01255522A (ja) * | 1988-04-06 | 1989-10-12 | Sumitomo Electric Ind Ltd | 耐熱耐油熱収縮チューブおよび絶縁電線 |
| DE3816327A1 (de) * | 1988-05-13 | 1989-11-23 | Hoechst Ag | Formkoerper aus einem vinylidenfluorid-copolymeren und verfahren zu seiner herstellung |
| US5282854A (en) * | 1989-10-11 | 1994-02-01 | Daikin Industries Ltd. | Fluorine-containing block copolymer and artificial lens comprising the same |
| US5441782A (en) * | 1991-07-16 | 1995-08-15 | Central Glass Company, Limited | Plastic laminate having polyamide resin surface layer and fluororesin surface layer |
| DE4224768A1 (de) * | 1992-07-27 | 1994-02-03 | Bayer Ag | Durch Pfropfcopolymerisation hergestellte thermoplastische Fluorelastomere |
| DE4440201A1 (de) * | 1994-11-10 | 1996-05-15 | Bayer Ag | Reaktive und verarbeitbare Fluorpolymere, ein Verfahren zu deren Herstellung, ein Verfahren zur Herstellung von vernetzten, bepfropften oder modifizierten Fluorpolymeren unter Einsatz der reaktiven und verarbeitbaren Fluorpolymere und deren Verwendung |
| DE19611311A1 (de) * | 1996-03-22 | 1997-09-25 | Dyneon Gmbh | Schichtstoff |
| IT1292391B1 (it) * | 1997-06-20 | 1999-02-08 | Ausimont Spa | Elastomeri termoplastici |
| CN1245183A (zh) * | 1997-11-17 | 2000-02-23 | 三星电子株式会社 | 光学聚合物组合物 |
| EP1127084A1 (en) * | 1998-09-15 | 2001-08-29 | National Power Plc | Water based grafting |
| GB2371262B (en) | 2001-01-17 | 2005-02-16 | Megaprint Group Ltd | Folding card |
| DE10351812B4 (de) * | 2003-10-30 | 2006-04-20 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Modifizierte Perfluor-Kunststoffe und Verfahren zu ihrer Herstellung |
| DE10351814A1 (de) * | 2003-10-30 | 2005-06-16 | Institut Für Polymerforschung Dresden E.V. | Radikalisch gekoppelte PTFE-Polymer-Compounds und Verfahren zu ihrer Herstellung |
| DE10351813B4 (de) * | 2003-10-30 | 2006-04-13 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Radikalisch gekoppelte PTFE-Polymer-Pulver und Verfahren zu ihrer Herstellung |
| EP2241581B1 (en) * | 2008-02-01 | 2014-04-30 | Asahi Glass Company, Limited | Thermoplastic fluororesin and method for producing the same |
| US9234062B2 (en) | 2011-12-14 | 2016-01-12 | Honeywell International Inc. | Process, properties, and applications of graft copolymers |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539488A (en) * | 1968-03-07 | 1970-11-10 | Ethyl Corp | Radiation curable polyvinyl chloride composition containing triallyl isocyanurate |
| US3947525A (en) * | 1973-01-30 | 1976-03-30 | Allied Chemical Corporation | Melt-processable, radiation cross-linkable E-CTFE copolymer compositions |
| US4155823A (en) * | 1976-10-12 | 1979-05-22 | Raychem Corporation | Shaped article from crosslinked fluorocarbon polymer and process therefor |
| US4472557A (en) * | 1983-05-19 | 1984-09-18 | Central Glass Company, Limited | Elastic fluorohydrocarbon resin and method of producing same |
-
1984
- 1984-07-11 JP JP14219684A patent/JPS6123638A/ja active Granted
-
1985
- 1985-06-28 IT IT8521351A patent/IT1206737B/it active
- 1985-07-05 GB GB08517035A patent/GB2161816B/en not_active Expired
- 1985-07-08 DE DE19853524370 patent/DE3524370A1/de active Granted
- 1985-07-10 FR FR858510586A patent/FR2567528B1/fr not_active Expired
- 1985-07-11 US US06/753,983 patent/US4652592A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434362A1 (en) * | 1989-12-19 | 1991-06-26 | Tomei Sangyo Kabushiki Kaisha | Graft copolymer, solution containing the graft copolymer, and method of treating contact lens with the solution |
| US5206298A (en) * | 1989-12-19 | 1993-04-27 | Tomei Sangyo Kabushiki Kaisha | Graft copolymer, solution containing the graft copolymer for treating contact lens, and method of treating contact lens with the solution and making hydrophilic lens surface |
| WO1994017114A1 (de) * | 1993-01-29 | 1994-08-04 | Wacker-Chemie Gmbh | Pfropf- und core-shell-copolymerisate mit verbesserter phasenanbindung zwischen pfropfgrundlage und aufgepfropfter polymerphase |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6123638A (ja) | 1986-02-01 |
| IT8521351A0 (it) | 1985-06-28 |
| FR2567528B1 (fr) | 1989-05-26 |
| US4652592A (en) | 1987-03-24 |
| FR2567528A1 (fr) | 1986-01-17 |
| GB2161816B (en) | 1987-10-21 |
| IT1206737B (it) | 1989-05-03 |
| JPS6352044B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-17 |
| GB8517035D0 (en) | 1985-08-14 |
| DE3524370C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-20 |
| GB2161816A (en) | 1986-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |