EP0224174A2 - Polymères organiques ayant des propriétés électriques - Google Patents
Polymères organiques ayant des propriétés électriques Download PDFInfo
- Publication number
- EP0224174A2 EP0224174A2 EP86115947A EP86115947A EP0224174A2 EP 0224174 A2 EP0224174 A2 EP 0224174A2 EP 86115947 A EP86115947 A EP 86115947A EP 86115947 A EP86115947 A EP 86115947A EP 0224174 A2 EP0224174 A2 EP 0224174A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- sulfur
- pyropolymer
- organic polymers
- weight
- conductivity
- 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.)
- Withdrawn
Links
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 34
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 71
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000011593 sulfur Substances 0.000 claims abstract description 63
- 239000007859 condensation product Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 238000000197 pyrolysis Methods 0.000 claims abstract description 7
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 6
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 6
- 229920001971 elastomer Polymers 0.000 claims abstract description 5
- 239000000806 elastomer Substances 0.000 claims abstract description 5
- 239000000945 filler Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 229920001940 conductive polymer Polymers 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 abstract description 6
- 229920002125 Sokalan® Polymers 0.000 description 24
- 239000004584 polyacrylic acid Substances 0.000 description 24
- 239000002245 particle Substances 0.000 description 17
- -1 radical anion salts Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- 229920001197 polyacetylene Polymers 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 235000019241 carbon black Nutrition 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011231 conductive filler Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004962 Polyamide-imide Substances 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920002312 polyamide-imide Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910017049 AsF5 Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 239000004425 Makrolon Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 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 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003055 poly(ester-imide) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920006289 polycarbonate film Polymers 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 102100021102 Hyaluronidase PH-20 Human genes 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920013632 Ryton Polymers 0.000 description 1
- 239000004736 Ryton® Substances 0.000 description 1
- 101150055528 SPAM1 gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical compound C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
Definitions
- the invention relates to organic polymers, such as plastics and paints, with increased electrical conductivity.
- This increased electrical conductivity is achieved by adding a sulfur-containing pyropolymer, which was obtained by pyrolysis of a sulfur-containing condensation product from aromatic compounds, which may contain heterocyclic rings with O, S or N as heteroatoms, and sulfur or sulfur-donating compounds.
- inorganic conductive fillers For example, metals, alloys, metal oxides, metal sulfides, metallized fillers or carbon, preferably in the form of carbon black or graphite, are used as inorganic conductive fillers.
- the conductivity-increasing fillers are used in the form of powders, beads, fibers or flakes. These conductive fillers ha ben, however, the disadvantage that they must be used in order to achieve the desired electrical conductivity in amounts that lead to an impairment of the mechanical properties of the organic polymers.
- this special polyacetylene modification With this special polyacetylene modification, a useful increase in the conductivity of the organic polymer is achieved even with additions of 0.1% by weight.
- this special polyacetylene modification has the disadvantage that it is not stable and that the conductivity decreases considerably when exposed to air and often when the polyacetylene is incorporated into the molten plastics.
- DE-OS 3 324 768 discloses condensation products of aromatic compounds with sulfur or sulfur-releasing compounds which have an electrical conductivity.
- the conductivity of these condensation products is not sufficient for use as conductive fillers in organic polymers.
- these condensation products have the disadvantage that the addition can lead to a sharp increase in the viscosity of the polymer melts, so that these melts can no longer be processed.
- organic polymers with increased electrical conductivity which remains unchanged even over long periods of time, are obtained, which also conduct under the influence of air, heat and shear forces Ability to remain unchanged if a sulfur-containing pyropolymer is added to these organic polymers, which was obtained by pyrolysis of a sulfur-containing condensation product from aromatic compounds, which may contain heterocyclic rings with O, S or N as heteroatoms, and sulfur or sulfur-donating compounds.
- the invention therefore relates to organic polymers with increased electrical conductivity, which are characterized in that they contain a sulfur-containing pyropolymer, which is obtained by pyrolysis of a sulfur-containing condensation product from aromatic compounds which optionally contain heterocyclic rings with O, S or N as heteroatoms, and sulfur or sulfur-donating compounds was obtained.
- the sulfur-containing pyropolymers to be used according to the invention are preferably obtained by condensing an aromatic compound with, sulfur or sulfur-releasing compounds such as polysulfides in a known manner, optionally in the presence of a solvent, at temperatures of 80-500 ° in a first reaction step and the sulfur-containing condensation product obtained is pyrolyzed in a second reaction stage at temperatures of 500-2000 ° C.
- This thermal treatment increases the electrical conductivity of the sulfur-containing condensation products by several powers of ten.
- the obtained sulfur-containing pyropolymers usually have an electrical conductivity of> 10 ⁇ 2S / cm without doping (i.e. without being oxidized or reduced). They are also extremely stable chemically and thermally.
- the sulfur-containing condensation products to be used as starting compounds for the preparation of the sulfur-containing pyropolymers and their preparation are known, e.g. from EP-A2-0131189 or EP-A1-0037829 and US Pat. No. 4,375,427. Because of their easy accessibility, the sulfur-containing condensation products described in EP-A2-0131189 are preferred.
- Aromatic compounds which contain 2 -9 carbocyclic rings and optionally 1 -3 heterocyclic rings with O, S or N as hetero atom are particularly suitable as starting compounds for the preparation of the sulfur-containing condensation products; preferred are the condensation products from the easily accessible, polycondensed aromatics, such as anthracene, chrysene, pyrene and the easily accessible heteroaromatics, such as carbazole.
- Mixtures of aromatic compounds, such as those present in the distillation residues of technical products, for example from the production of anthracene, antrachinone or bisphenol, and in the distillation residues from cracking processes or from petroleum processing, can also be used as starting compounds.
- the sulfur-containing pyropolymers are obtained in the form of shiny black masses. These are crushed to the desired grain size using conventional means; this is usually less than 600 ⁇ ; the grain size of the pyropolymers is preferably in the range from 0.1 to 100 ⁇ m.
- Suitable organic polymers whose conductivity can be increased by the addition of the sulfur-containing pyropolymers according to the invention are thermoplastics, thermosets, elastomers and paints.
- thermoplastics polymers and copolymers of monoolefinically unsaturated monomers, for example high-pressure or low-pressure polyethylene, polypropylene, polyisobutylene, polyvinyl chloride, and also as a copolymer with vinyl acetate, polyvinyl alcohol, polyvinyl acetate, polyvinylidene chloride, polyvinylidene fluoride, polytetrafluoroethylene, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic acid, polyacrylic
- thermosets e.g. Reaction products of formaldehyde with phenol, cresols, urea, melamine or their mixtures or casting resins made from unsaturated polyesters, epoxies, polyurethanes or silicones.
- Suitable elastomers are, for example, natural rubber, optionally chlorinated or brominated polybutadiene, polyisoprene, isobutylene polymers, ethylene, propylene copolymers, sulfochlorinated polyethylene, elastomeric polyurethanes or silicone rubbers.
- Suitable varnishes whose conductivity can be increased by the addition of sulfur-containing pyropolymer according to the invention are both varnish systems which are drying or crosslinking at room temperature and stoving varnishes.
- the varnish systems to be used at room temperature include alkyd resins, unsaturated polyester resins, polyurethane resins, epoxy resins, modified fats and Oils, polymers or copolymers based on vinyl chloride, vinyl ether, vinyl ester, styrene, acrylic acid, acrylonitrile or acrylic ester, cellulose derivatives.
- the stoving lacquers are the lacquer systems which crosslink at higher temperatures, such as, for example, polyurethanes made of hydroxyl-containing polyethers, polyesters or Polyacrylates and masked polyisocyanates, melamine resins made of etherified melamine-formaldehyde resins and hydroxyl group-containing polyethers, polyesters or polyacrylates, epoxy resins made of polyepoxides and polycarboxylic acids, carboxyl group-containing polyacrylates and carboxyl group-containing polyesters, stoving lacquers made of polyester, polyester imides, polyester amide amides and polyamide imides, polyamideimides suitable. These stoving lacquers can usually be applied both as powder and from solution.
- the organic polymers to be finished according to the invention can also be in the form of copolymers, polymer blends or polymer alloys.
- the sulfur-containing pyropolymers can also be added to polymers that already show intrinsic electrical conductivity, e.g. Polyacetylene, polyparaphenylene, polythiophene, polypyrrole, polyphenylene vinylene, polyphthalocyanines or polyanilines.
- the intrinsically conductive polymers can be present in undoped or doped form. Suitable dopants are preferably oxidizing agents such as AsF5, SbCl5, FeCl3 or halogens, or reducing agents such as alkali metals, optionally as alkali naphthalide.
- the conductivity of the pyropolymers to be used according to the invention can be increased even further by treating the pyropolymers with chemical or physical methods.
- partial oxidation or reduction of the sulfur-containing pyropolymers can lead to high levels conductive intercalation connections are made.
- Suitable oxidizing agents are halogens such as fluorine, chlorine, bromine or iodine, metal chlorides such as FeCl3, AsF5, SbCl5, SbF5 or oxidizing acids such as HNO3 or H2SO4.
- the alkali and alkaline earth metals serve as reducing agents. Oxidation and reduction can also be carried out electrochemically in the presence of a suitable conductive salt.
- the pyropolymers to be used according to the invention can be incorporated into the organic polymers by methods customary for the incorporation of fillers into organic polymers.
- they can be mixed with thermoplastics by dry mixing and subsequent extrusion in a commercially available screw or directly in a screw by metering them in together.
- Pellets are preferably produced from the thermoplastic and the sulfur-containing pyropolymer in a first stage, which are then processed in a second stage to give the desired shaped articles.
- the pyropolymer can be stirred directly into the polymer solution and then homogenized, for example with a dissolver or a ball mill.
- the pyropolymer can also be dispersed in a suitable solvent and, if appropriate, additionally ground, and then the organic polymer, if appropriate dissolved in a suitable solvent, added and, if appropriate, homogenized again with suitable equipment.
- air that has been stirred in must be removed by suitable measures, for example applying a vacuum.
- Can be used to manufacture thermosets the pyropolymer is stirred directly into the liquid or melted mass and then comminuted and homogenized, for example with a dissolver or a ball mill. It is also possible to homogenize the pyropolymer and the thermosetting resin as a solution or suspension, the solvent having to be removed again, for example under reduced pressure, in a second operation.
- the organic polymers can contain conventional additives, such as fillers, pigments, antioxidants, UV stabilizers, hydrolysis stabilizers, plasticizers and / or other conductivity-increasing additives.
- the pyropolymers to be used according to the invention are usually used in amounts of 5-80% by weight, preferably 10-70% by weight, particularly preferably in amounts of 20-60% by weight, based on the total weight of the conductive polymer.
- a significant advantage of the pyropolymers to be used according to the invention over carbon black is the possibility of being able to incorporate even amounts above 30% by weight without any problems. Even the incorporation of 50% by weight of pyropolymer into thermoplastic materials does not pose any difficulties. Rather, the sulfur-containing pyropolymers to be used according to the invention have the surprising property that they not only improve the conductivity but - in contrast to carbon black, for example - also improve the mechanical properties of the organic polymers, for example of polyamides.
- the pyropolymer to be used according to the invention can also be used as a black pigment; if the temperature falls below a certain minimum amount, which may vary depending on the polymer system and processing conditions, the conductivity will no longer increase.
- the polymer compounds according to the invention show specific conductivities between 10 ⁇ 12 and 100 Siemens / cm. They can be used to manufacture antistatic, semiconducting or conductive plastic parts, foils or coatings. They are used as electrodes, for example in electrolysis cells or in batteries, as heat conductors, as non-rechargeable housings and for shielding electromagnetic waves.
- This condensation product is heated to 1000 ° C. in the face grinding cup described in Example 1 within 12 hours and kept at this temperature for 10 hours. 1461 g of pyropolymer containing sulfur are obtained in the form of a shiny metallic mass (specific conductivity: 14.3 S / cm; sulfur content: 7.4% by weight).
- This condensation product is heated for 7 hours at 350 ° C. in the flat ground cup made of quartz glass described for the heart position of the pyropolymer A. The mixture is then heated to 1000 ° C. in the course of 6 hours and kept at this temperature for 10 hours. 1364 g of pyropolymer containing sulfur are obtained in the form of a shiny metallic mass (conductivity: 12.8 S / cm; sulfur content: 7.8% by weight.)
- the table below shows the amounts of pyropolymer A used and the surface resistance of the polycarbonate films finished with the stated amounts of pyropolymer A.
- Elastomer's vinyl polybutadiene (made from butadiene1.2) is cooled to -80 ° C and comminuted in a granulating machine. 55 parts by weight of this granulate are mixed with 45 parts by weight of pyropolymer E (particle size: 5 - 25 ⁇ ). The mixture is pressed into a plate under a pressure of 450 kg / cm2. The elastomeric plate has a specific conductivity of 2.4 ⁇ 10 ⁇ 1 S / cm.
- 250 parts by weight of polypropylene are mixed with 750 parts by weight of pyropolymer A (particle size: ⁇ 65 ⁇ ) and processed into a strand in an extruder at 220 ° C.
- a plate made from this strand at 200 ° C and a pressure of 500 Kp / cm2 has a specific conductivity of 6.9 ⁇ 10 ⁇ 4 S / cm.
- 300 parts by weight of polymerized methyl methacrylate are mixed with 250 parts by weight of pyropolymer C (particle size: ⁇ 500 ⁇ ) mixed with 100 mg of bis (4-chlorobenzoyl) peroxide and then at 160 ° C. and a pressure of 570 Kp / cm2 pressed.
- the plate thus obtained has a specific conductivity of 8.7 ⁇ 10 ⁇ 1 S / cm.
- the table below shows the amounts of copolymer and pyropolymer used in the individual experiments and the specific conductivities of the polymer plates obtained from these components.
- the table below shows the amounts of pyropolymer A added and the surface resistance of the coatings obtained with these amounts.
- a plate made of 100 parts by weight of polyparaphenylene sulfide and 100 parts by weight of pyropolymer A (particle size: ⁇ 63 ⁇ ) (dimensions: 25 ⁇ 25 ⁇ 2 mm) was provided with 2 electrical contacts, coated with a polyhydantoin varnish and in a vessel covered with 50 g of water. After applying a DC voltage of 24 V / 30 V / 36 V, the water warms up to 47 ° C / 53 ° C / 56 ° C. I.e. the plate acted as a heating plate.
- 100 g of a liquid epoxy resin made from technical bisglycidyl hexahydrophthalate (epoxy value: 0.58) and 100 g of melted hexahydrophthalic anhydride are mixed with 100 g of pyropolymer C (particle size: ⁇ 63 ⁇ ) and mixed with 2 g of dimethylbenzylamine as a catalyst. After degassing, the mass is poured into a mold and heated to 80 ° C for 4 hours and then to 160 ° C for 16 hours.
- the cast resin molded body obtained in this way has a specific conductivity of 1.8 ⁇ 10 ⁇ 5 S / cm.
- 50 parts by weight of powdered pyropolymer A (particle size: ⁇ 63 ⁇ ) and 50 parts by weight of polyphenylene sulfide (Ryton P 4 from Phillips Petroleum Comp.) are first mixed mechanically with one another. This mixture is dried in vacuo at 130 ° C. and then melt-compounded at 330 ° C. using a twin-screw extruder (ZSK 32 from Werner & Pfleiderer). The melt strand emerging from the extruder is granulated after cooling. After predrying at 130 ° C. at a melt temperature of 340 ° C.
- round plates (diameter: 800 mm, thickness: 2 mm) are injected from the granules obtained in this way.
- the electrical resistance values of the round plates obtained in this way are: volume resistivity: 110 ⁇ ⁇ cm specific surface resistance: 560 ⁇
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19853542231 DE3542231A1 (de) | 1985-11-29 | 1985-11-29 | Organische polymere mit elektrischen eigenschaften |
DE3542231 | 1985-11-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0224174A2 true EP0224174A2 (fr) | 1987-06-03 |
EP0224174A3 EP0224174A3 (fr) | 1988-11-02 |
Family
ID=6287178
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86115947A Withdrawn EP0224174A3 (fr) | 1985-11-29 | 1986-11-18 | Polymères organiques ayant des propriétés électriques |
Country Status (4)
Country | Link |
---|---|
US (1) | US4798686A (fr) |
EP (1) | EP0224174A3 (fr) |
JP (1) | JPS62131068A (fr) |
DE (1) | DE3542231A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101384168B (zh) * | 2006-02-17 | 2011-08-17 | 德拉瓦尔控股股份有限公司 | 有传送奶的管状部件的装置 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5714566A (en) | 1981-11-13 | 1998-02-03 | The Boeing Company | Method for making multiple chemically functional oligomers |
US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
US5516876A (en) | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
US5780583A (en) * | 1991-01-09 | 1998-07-14 | The Boeing Company | Reactive polyarylene sulfide oligomers |
US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
US5431998A (en) * | 1993-05-14 | 1995-07-11 | Lockheed Corporation | Dimensionally graded conductive foam |
US5464570A (en) * | 1993-10-25 | 1995-11-07 | Delco Electronics Corporation | THFA/PDP thermoset thick films for printed circuits |
US7163746B2 (en) * | 2002-06-12 | 2007-01-16 | Eastman Kodak Company | Conductive polymers on acicular substrates |
DE102005053646A1 (de) * | 2005-11-10 | 2007-05-16 | Starck H C Gmbh Co Kg | Polymerbeschichtungen mit verbesserter Lösungsmittelbeständigkeit |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2834390A1 (de) * | 1978-08-05 | 1980-02-14 | Preh Elektro Feinmechanik | Elektrisch leitfaehige kunststoff- formmasse und verfahren zu deren herstellung |
EP0131189A2 (fr) * | 1983-07-08 | 1985-01-16 | Bayer Ag | Procédé de préparation de polymères conducteurs de l'électricité |
EP0214506A1 (fr) * | 1985-08-29 | 1987-03-18 | Bayer Ag | Polymères électriquement conducteurs et procédé pour leur préparation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4375427A (en) * | 1979-12-13 | 1983-03-01 | Allied Corporation | Thermoplastic conductive polymers |
DE3005849A1 (de) * | 1980-02-16 | 1981-09-03 | Bayer Ag, 5090 Leverkusen | Elektrisch leitende und antistatische formmassen |
DE3018459A1 (de) * | 1980-05-14 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung elektrisch leitfaehiger loeslicher heteropolyphenylene und deren verwendung in der elektrotechnik und zur antistatischen ausruestung von kunststoffen |
DE3113331A1 (de) * | 1981-04-02 | 1982-10-28 | Bayer Ag, 5090 Leverkusen | Kletten- bzw. faserfoermige, dotierte polyacetylenteilchen enthaltende thermoplastische kunststoffe und verfahren zu ihrer herstellung |
-
1985
- 1985-11-29 DE DE19853542231 patent/DE3542231A1/de not_active Withdrawn
-
1986
- 1986-11-18 EP EP86115947A patent/EP0224174A3/fr not_active Withdrawn
- 1986-11-18 US US06/932,077 patent/US4798686A/en not_active Expired - Fee Related
- 1986-11-25 JP JP61278896A patent/JPS62131068A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2834390A1 (de) * | 1978-08-05 | 1980-02-14 | Preh Elektro Feinmechanik | Elektrisch leitfaehige kunststoff- formmasse und verfahren zu deren herstellung |
EP0131189A2 (fr) * | 1983-07-08 | 1985-01-16 | Bayer Ag | Procédé de préparation de polymères conducteurs de l'électricité |
EP0214506A1 (fr) * | 1985-08-29 | 1987-03-18 | Bayer Ag | Polymères électriquement conducteurs et procédé pour leur préparation |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101384168B (zh) * | 2006-02-17 | 2011-08-17 | 德拉瓦尔控股股份有限公司 | 有传送奶的管状部件的装置 |
Also Published As
Publication number | Publication date |
---|---|
DE3542231A1 (de) | 1987-06-04 |
US4798686A (en) | 1989-01-17 |
EP0224174A3 (fr) | 1988-11-02 |
JPS62131068A (ja) | 1987-06-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3855678T2 (de) | Intrinsisch leitfähiges polymer in form eines dispergierbaren körpers, seine herstellung und seine anwendung | |
US5595689A (en) | Highly conductive polymer blends with intrinsically conductive polymers | |
EP0224174A2 (fr) | Polymères organiques ayant des propriétés électriques | |
EP0168620B1 (fr) | Procédé de fabrication des mélanges polymériques moulables à partir de polymères électriquement conducteurs et utilisation de ces mélanges | |
EP1706431B1 (fr) | Dispersions de polymeres intrinsequement conducteurs et leur procede de production | |
EP0181587B1 (fr) | Mélanges polymères thermoplastiques antistatiques ou électriquement semi-conducteurs, procédé pour leur fabrication et leur mise en oeuvre | |
DE69030317T2 (de) | Harzzusammensetzung | |
Yang et al. | Preparation of low density polyethylene-based polyaniline conducting polymer composites with low percolation threshold via extrusion | |
DE69321673T3 (de) | Leitendes Kunststoffmaterial und Methode zu seiner Herstellung | |
DE3543301A1 (de) | Elektrisch leitende feste kunststoffe | |
DE2625674A1 (de) | Mittel zum flammfestausruesten von kunststoffen | |
DE2625692C3 (de) | Flammfestausrüsten von Kunststoffen | |
DE2059329A1 (de) | Lagerbestaendige Epoxyharzmasse | |
DE4234688A1 (de) | Verfahren zur herstellung eines elektrisch leitenden verbundmaterials | |
EP0446172A2 (fr) | Masses de pressage électriquement conductrices et matières de remplissage à base de polyhéteroaromates et de sulfates polymères | |
EP0566536A1 (fr) | Compositions de polymères conductrices d'électricité et leur usage | |
EP0241927A1 (fr) | Matière de revêtement à haute conductivité électrique et son application à la fabrication de revêtements | |
DE1208490C2 (de) | Verwendung von bestimmten oxymethylenpolymeren zum herstellen von verbundmaterialien | |
DE19742865C1 (de) | Duroplastische Formmassen für Formteile zur direkten elektrophoretischen Beschichtung, Verfahren zu ihrer Herstellung und ihre Verwendung | |
EP0335184A1 (fr) | Matières plastiques organiques ayant une conductibilité électrique élevée | |
EP0566533A1 (fr) | Polymères vinylphénoliques sulfatés, compositions contenant des polymères vinylphénoliques sulfatés et leur application | |
DE3609137A1 (de) | Filme aus elektrisch leitfaehigen polymeren sowie mit diesen filmen beschichtete elektrodenmaterialien | |
EP0071862A1 (fr) | Polystyrène à conductibilité électrique élevée | |
DE2166805A1 (de) | Leitlack | |
DE2136838C3 (de) | Thermoplastische Massen aus Gemischen von Polyphenylenoxid und einem Styrol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 19861118 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): CH DE FR GB IT LI |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): CH DE FR GB IT LI |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Withdrawal date: 19900119 |
|
R18W | Application withdrawn (corrected) |
Effective date: 19900119 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: HOCKER, JUERGEN, DR. Inventor name: FUELLMANN, HEINZ-JOSEF, DR. Inventor name: ROTTMAIER, LUDWIG, ING.-GRAD. Inventor name: KIRSCH, JUERGEN, DR. Inventor name: REINKING, KLAUS, DR. |