CA1337780C - Composition antistatique et conductrice - Google Patents

Composition antistatique et conductrice

Info

Publication number: CA1337780C
Authority: CA; Canada
Prior art keywords: polymer; substituted; groups; copolymers; radical
Prior art date: 1988-09-30
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 - Fee Related

Application number

CA000616788A

Other languages

English (en)

Inventor

Jurgen Finter

Bruno Hilti

Carl W. Mayer

Ernst Minder

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1988-09-30

Filing date

1993-12-31

Publication date

1995-12-19

1989-09-25 Priority claimed from CA000612781A external-priority patent/CA1334238C/fr

1993-12-31 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1993-12-31 Priority to CA000616788A priority Critical patent/CA1337780C/fr

1995-12-19 Application granted granted Critical

1995-12-19 Publication of CA1337780C publication Critical patent/CA1337780C/fr

2009-09-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 48
229910052801 chlorine Inorganic materials 0.000 claims abstract description 52
229910052794 bromium Inorganic materials 0.000 claims abstract description 29
229920001169 thermoplastic Polymers 0.000 claims abstract description 25
229910052740 iodine Inorganic materials 0.000 claims abstract description 17
125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
-1 glycidyl compound Chemical class 0.000 claims description 68
229920001577 copolymer Polymers 0.000 claims description 58
150000003254 radicals Chemical class 0.000 claims description 29
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 22
239000005977 Ethylene Substances 0.000 claims description 22
229920001519 homopolymer Polymers 0.000 claims description 17
150000002009 diols Chemical class 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
239000004416 thermosoftening plastic Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 10
125000003700 epoxy group Chemical group 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000004427 diamine group Chemical group 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 90
238000000576 coating method Methods 0.000 abstract description 7
239000002131 composite material Substances 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 4
238000000465 moulding Methods 0.000 abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 2
239000011630 iodine Substances 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 73
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
150000001875 compounds Chemical class 0.000 description 24
229910052739 hydrogen Inorganic materials 0.000 description 21
229910052731 fluorine Inorganic materials 0.000 description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 17
238000000034 method Methods 0.000 description 15
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
239000004642 Polyimide Substances 0.000 description 12
239000005062 Polybutadiene Substances 0.000 description 11
150000001993 dienes Chemical class 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
229920001721 polyimide Polymers 0.000 description 11
229920002857 polybutadiene Polymers 0.000 description 10
239000002904 solvent Substances 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 9
MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229920006324 polyoxymethylene Polymers 0.000 description 8
239000004743 Polypropylene Substances 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
229920000915 polyvinyl chloride Polymers 0.000 description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
150000004985 diamines Chemical group 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
229920001684 low density polyethylene Polymers 0.000 description 6
239000004702 low-density polyethylene Substances 0.000 description 6
239000004417 polycarbonate Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
239000000243 solution Substances 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
125000006839 xylylene group Chemical group 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
125000004956 cyclohexylene group Chemical group 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
150000003335 secondary amines Chemical class 0.000 description 5
229910052711 selenium Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
229920002396 Polyurea Polymers 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
150000001991 dicarboxylic acids Chemical class 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
125000004185 ester group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229920001903 high density polyethylene Polymers 0.000 description 4
239000004700 high-density polyethylene Substances 0.000 description 4
125000002346 iodo group Chemical group I* 0.000 description 4
150000005673 monoalkenes Chemical class 0.000 description 4
239000000178 monomer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
229920000058 polyacrylate Polymers 0.000 description 4
229920000515 polycarbonate Polymers 0.000 description 4
229920000728 polyester Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
229920001897 terpolymer Polymers 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000005250 alkyl acrylate group Chemical group 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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 3
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
238000005266 casting Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000004979 cyclopentylene group Chemical group 0.000 description 3
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000001125 extrusion Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
229920002492 poly(sulfone) Polymers 0.000 description 3
229920006393 polyether sulfone Polymers 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
229920000193 polymethacrylate Polymers 0.000 description 3
229920006380 polyphenylene oxide Polymers 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000007493 shaping process Methods 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
GKFWNPPZHDYVLI-UHFFFAOYSA-N 2,3-dichloropropanoic acid Chemical compound OC(=O)C(Cl)CCl GKFWNPPZHDYVLI-UHFFFAOYSA-N 0.000 description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
NYYNAVMKBFRKHB-UHFFFAOYSA-N 2-methyltetracene Chemical class C1=CC=CC2=CC3=CC4=CC(C)=CC=C4C=C3C=C21 NYYNAVMKBFRKHB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
229910019213 POCl3 Inorganic materials 0.000 description 2
239000002033 PVDF binder Substances 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
239000004734 Polyphenylene sulfide Substances 0.000 description 2
229920001328 Polyvinylidene chloride Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
229920000800 acrylic rubber Polymers 0.000 description 2
229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000003490 calendering Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229920002678 cellulose Chemical class 0.000 description 2
239000001913 cellulose Chemical class 0.000 description 2
229940106681 chloroacetic acid Drugs 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000002322 conducting polymer Substances 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
229920000578 graft copolymer Polymers 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229920000092 linear low density polyethylene Polymers 0.000 description 2
239000004707 linear low-density polyethylene Substances 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
239000000206 moulding compound Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
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235000019256 formaldehyde Nutrition 0.000 description 1
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238000005227 gel permeation chromatography Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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 1
238000010438 heat treatment Methods 0.000 description 1
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238000001746 injection moulding Methods 0.000 description 1
230000001788 irregular Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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150000003951 lactams Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
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238000013508 migration Methods 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
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MDKQJOKKKZNQDG-UHFFFAOYSA-N n,n'-dimethylhexane-1,6-diamine Chemical compound CNCCCCCCNC MDKQJOKKKZNQDG-UHFFFAOYSA-N 0.000 description 1
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AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000002245 particle Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000012994 photoredox catalyst Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920006149 polyester-amide block copolymer 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
229920001470 polyketone Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002620 polyvinyl fluoride Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000003198 secondary alcohol group Chemical group 0.000 description 1
239000011265 semifinished product Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
VPQBLCVGUWPDHV-UHFFFAOYSA-N sodium selenide Chemical compound [Na+].[Na+].[Se-2] VPQBLCVGUWPDHV-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
150000003518 tetracenes Chemical class 0.000 description 1
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
238000010105 thermoset forming Methods 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
FCFMKFHUNDYKEG-UHFFFAOYSA-N thietane 1,1-dioxide Chemical compound O=S1(=O)CCC1 FCFMKFHUNDYKEG-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

CA000616788A 1988-09-30 1993-12-31 Composition antistatique et conductrice Expired - Fee Related CA1337780C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616788A CA1337780C (fr)	1988-09-30	1993-12-31	Composition antistatique et conductrice

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH3639/88-6		1988-09-30
CH363988		1988-09-30
CA000612781A CA1334238C (fr)	1988-09-30	1989-09-25	Composition antistatique et conductrice
CA000616788A CA1337780C (fr)	1988-09-30	1993-12-31	Composition antistatique et conductrice

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000612781A Division CA1334238C (fr)	1988-09-30	1989-09-25	Composition antistatique et conductrice

Publications (1)

Publication Number	Publication Date
CA1337780C true CA1337780C (fr)	1995-12-19

Family

ID=25673081

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000616789A Expired - Fee Related CA1339945C (fr)	1988-09-30	1993-12-31	Composition conductrice antistatique
CA000616788A Expired - Fee Related CA1337780C (fr)	1988-09-30	1993-12-31	Composition antistatique et conductrice

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA000616789A Expired - Fee Related CA1339945C (fr)	1988-09-30	1993-12-31	Composition conductrice antistatique

Country Status (1)

Country	Link
CA (2)	CA1339945C (fr)

1993
- 1993-12-31 CA CA000616789A patent/CA1339945C/fr not_active Expired - Fee Related
- 1993-12-31 CA CA000616788A patent/CA1337780C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA1339945C (fr)	1998-07-07

Legal Events

Date	Code	Title	Description
2004-12-20	MKLA	Lapsed

Publication	Publication Date	Title
US5009812A (en)	1991-04-23	Antistatic and electrically conducting polymers and moulding materials
US4992559A (en)	1991-02-12	Polymerizable thiophene monomers
US5648453A (en)	1997-07-15	Electroconductive polymer and process for producing the polymer
US5795953A (en)	1998-08-18	Soluble, electroconductive polypyrrole and method for preparing the same
EP0575291A2 (fr)	1993-12-22	Compositions de polymère èlectriquement conductrices et leur utilisation
CA1334238C (fr)	1995-01-31	Composition antistatique et conductrice
CN88100800A (zh)	1988-09-21	自由基聚合反应组合物
JPH05255576A (ja)	1993-10-05	面状発熱体及びその製造法
US3346444A (en)	1967-10-10	Electrically conductive polymers and process of producing the same
US5206297A (en)	1993-04-27	Electrically conductive moulding compositions and fillers from polyheteroaromatic compounds and polymeric sulfates
US4769177A (en)	1988-09-06	Electrically conductive and antistatic moulding compositions
JPH11279279A (ja)	1999-10-12	透明電気伝導性ポリマー
US5688873A (en)	1997-11-18	Electroconductive polymer and process for producing the polymer
US5328961A (en)	1994-07-12	Electrically conductive polythiophenecarbonyl polymer networks
US5427715A (en)	1995-06-27	Electrically conductive plastics compositions and the use thereof
CA1337780C (fr)	1995-12-19	Composition antistatique et conductrice
US5153321A (en)	1992-10-06	Antistatic and electrically conducting polymers and moulding materials
US5492652A (en)	1996-02-20	Dithiopentacene derivatives, their preparation and the use thereof as electron acceptors in charge transfer complexes
US5258140A (en)	1993-11-02	Charge transfer complexes with ferrocenes, their preparation and the use thereof
US5482984A (en)	1996-01-09	Synthetic polymer compositions containing charge transfer complexes, their preparation and the use thereof
US5276102A (en)	1994-01-04	Electrically conductive polythiopheneamine polymer networks
CA1338966C (fr)	1997-03-04	Images en relief antistatiques et conductrices d'electricite, methodes de production de ces images, agents d'enrobage et polymeres sensibles aux radiations
KR100445287B1 (ko)	2004-08-21	폴리아닐린의 새로운 제조 방법
EP0782750A1 (fr)	1997-07-09	Nouvelle composition electroconductrice
JPH04306230A (ja)	1992-10-29	アニリン共重合体およびその組成物