CA2124647C - Poly(sels de pyridinium) - Google Patents

Poly(sels de pyridinium) Download PDF

Info

Publication number: CA2124647C
Authority: CA; Canada
Prior art keywords: group; formula; radical; meta; para
Prior art date: 1994-05-30
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 - Lifetime

Application number

CA002124647A

Other languages

English (en)

Other versions

CA2124647A1 (fr

Inventor

Frank W. Harris

Chun Hua K. Chuang

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.)

University of Akron

Original Assignee

University of Akron

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.)

1994-05-30

Filing date

1994-05-30

Publication date

2007-05-01

1994-05-30 Application filed by University of Akron filed Critical University of Akron

1994-05-30 Priority to CA002124647A priority Critical patent/CA2124647C/fr

1995-12-01 Publication of CA2124647A1 publication Critical patent/CA2124647A1/fr

2007-05-01 Application granted granted Critical

2007-05-01 Publication of CA2124647C publication Critical patent/CA2124647C/fr

2014-05-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 Poly (pyridinium salts Chemical class 0.000 title claims description 73
229920000642 polymer Polymers 0.000 claims abstract description 63
229920002348 Polypyridinium salt Polymers 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 5
125000003277 amino group Chemical group 0.000 claims description 70
125000004432 carbon atom Chemical group C* 0.000 claims description 46
150000004985 diamines Chemical class 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
150000003254 radicals Chemical class 0.000 claims description 18
150000002500 ions Chemical class 0.000 claims description 14
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
125000004430 oxygen atom Chemical group O* 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
150000005840 aryl radicals Chemical class 0.000 claims description 8
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
239000004305 biphenyl Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
235000010290 biphenyl Nutrition 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
LLYCMZGLHLKPPU-UHFFFAOYSA-M perbromate Chemical compound [O-]Br(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-M 0.000 claims description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 4
239000003880 polar aprotic solvent Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
229920006254 polymer film Polymers 0.000 claims 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
239000011593 sulfur Substances 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 abstract description 10
150000001450 anions Chemical class 0.000 abstract description 8
229910052751 metal Inorganic materials 0.000 abstract description 7
239000002184 metal Substances 0.000 abstract description 7
239000002019 doping agent Substances 0.000 abstract description 6
239000012528 membrane Substances 0.000 abstract description 5
238000000926 separation method Methods 0.000 abstract description 4
238000000576 coating method Methods 0.000 abstract description 3
229920001940 conductive polymer Polymers 0.000 abstract description 3
239000004020 conductor Substances 0.000 abstract description 3
238000005260 corrosion Methods 0.000 abstract description 3
239000011248 coating agent Substances 0.000 abstract description 2
239000002322 conducting polymer Substances 0.000 abstract description 2
239000003054 catalyst Substances 0.000 abstract 1
238000006068 polycondensation reaction Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
150000001875 compounds Chemical class 0.000 description 25
239000000203 mixture Substances 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
238000006116 polymerization reaction Methods 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000000835 fiber Substances 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
238000003756 stirring Methods 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 9
239000000178 monomer Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000010408 film Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 5
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 4
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000004984 aromatic diamines Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000005611 electricity Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 3
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical class CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 3
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 3
QNRXYILTAFQFSQ-UHFFFAOYSA-N 2,6-diphenylpyrylium Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=[O+]1 QNRXYILTAFQFSQ-UHFFFAOYSA-N 0.000 description 2
QBSMHWVGUPQNJJ-UHFFFAOYSA-N 4-[4-(4-aminophenyl)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(C=2C=CC(N)=CC=2)C=C1 QBSMHWVGUPQNJJ-UHFFFAOYSA-N 0.000 description 2
NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000005002 aryl methyl group Chemical group 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000003517 fume Substances 0.000 description 2
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
BDELMXZTWBWGON-UHFFFAOYSA-M pyrylium trifluoromethanesulfonate Chemical compound S(=O)(=O)(C(F)(F)F)[O-].[O+]1=CC=CC=C1 BDELMXZTWBWGON-UHFFFAOYSA-M 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
230000011514 reflex Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
HOMLSEIOAJYHEK-UHFFFAOYSA-N 1,4,4-tris(4-aminophenyl)cyclohexa-2,5-dien-1-amine Chemical compound C1=CC(N)=CC=C1C1(N)C=CC(C=2C=CC(N)=CC=2)(C=2C=CC(N)=CC=2)C=C1 HOMLSEIOAJYHEK-UHFFFAOYSA-N 0.000 description 1
YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
ANEVGZIVRUDOKI-UHFFFAOYSA-N 3-[2-(1,5-dioxo-1,5-diphenylpentan-3-yl)phenyl]-1,5-diphenylpentane-1,5-dione Chemical compound C=1C=CC=CC=1C(=O)CC(C=1C(=CC=CC=1)C(CC(=O)C=1C=CC=CC=1)CC(=O)C=1C=CC=CC=1)CC(=O)C1=CC=CC=C1 ANEVGZIVRUDOKI-UHFFFAOYSA-N 0.000 description 1
ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
CPBGOWIFSRZWIZ-UHFFFAOYSA-N 4-(4-amino-2-bromophenyl)-3-bromoaniline Chemical compound BrC1=CC(N)=CC=C1C1=CC=C(N)C=C1Br CPBGOWIFSRZWIZ-UHFFFAOYSA-N 0.000 description 1
XKXPBJBODVHDAW-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl XKXPBJBODVHDAW-UHFFFAOYSA-N 0.000 description 1
QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000010669 acid-base reaction Methods 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
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
238000000149 argon plasma sintering Methods 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000012691 depolymerization reaction Methods 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
229920005570 flexible polymer Polymers 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000006384 methylpyridyl group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
LLYCMZGLHLKPPU-UHFFFAOYSA-N perbromic acid Chemical compound OBr(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-N 0.000 description 1
JLKXXDAJGKKSNK-UHFFFAOYSA-N perchloric acid;pyridine Chemical compound OCl(=O)(=O)=O.C1=CC=NC=C1 JLKXXDAJGKKSNK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000005518 polymer electrolyte Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000004360 trifluorophenyl group Chemical group 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

CA002124647A 1994-05-30 1994-05-30 Poly(sels de pyridinium) Expired - Lifetime CA2124647C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002124647A CA2124647C (fr)	1994-05-30	1994-05-30	Poly(sels de pyridinium)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002124647A CA2124647C (fr)	1994-05-30	1994-05-30	Poly(sels de pyridinium)

Publications (2)

Publication Number	Publication Date
CA2124647A1 CA2124647A1 (fr)	1995-12-01
CA2124647C true CA2124647C (fr)	2007-05-01

Family

ID=4153700

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002124647A Expired - Lifetime CA2124647C (fr)	1994-05-30	1994-05-30	Poly(sels de pyridinium)

Country Status (1)

Country	Link
CA (1)	CA2124647C (fr)

1994
- 1994-05-30 CA CA002124647A patent/CA2124647C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2124647A1 (fr)	1995-12-01

Legal Events

Date	Code	Title	Description
2001-03-06	EEER	Examination request
2014-08-03	MKEX	Expiry	Effective date: 20140530

Publication	Publication Date	Title
US4108835A (en)	1978-08-22	Phenylated aromatic heterocyclic polymers
US6132641A (en)	2000-10-17	Composition and support material comprising poly(9,9'-spiro-bisfluorenes)
Hsiao et al.	2006	Novel aromatic polyamides and polyimides functionalized with 4‐tert‐butyltriphenylamine groups
US4841021A (en)	1989-06-20	Polypyridinium
Aly et al.	2000	New polymer syntheses. IX. Synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties
JPH03504872A (ja)	1991-10-24	高い使用温度における導電性ポリマーとその製造方法
US4898923A (en)	1990-02-06	Polypyridinium copolymer
US6518394B2 (en)	2003-02-11	End-functionalized aniline-based oligomers, corrosion-resistant copolymers and methods of making the same
Mikroyannidis	2000	Synthesis and characterization of soluble, photoluminescent polyamides, polyesters and polyethers containing 9, 10-di (4-biphenylyl) anthracene segments in the main chain
US5578699A (en)	1996-11-26	Process for making amino functional poly(para-phenylene vinylene)s
JP4269113B2 (ja)	2009-05-27	芳香族アミン誘導体及び可溶性導電性化合物
WO1997014729A9 (fr)	1997-08-07	Derives polyaniline et revetements realises avec ces derives
Tundidor‐Camba et al.	2011	Polyamides obtained by direct polycondesation of 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl] fluoren‐9‐YL]‐2‐methyl‐phenoxy] aniline with dicarboxylic acids based on a diphenyl‐silane moiety
Liou et al.	2006	Synthesis, photoluminescence, and electrochromic properties of wholly aromatic polyamides bearing naphthylamine chromophores
US5763563A (en)	1998-06-09	Poly-pyridinium salts
Lozano et al.	1995	Synthesis and properties of aromatic polyamides with oligobenzamide pendent groups. I. Poly‐5‐(4‐benzoylamino‐1‐benzoylamino) isophthalamides
CA2124647C (fr)	2007-05-01	Poly(sels de pyridinium)
US5863651A (en)	1999-01-26	Poly-pyridinium salts
US4046779A (en)	1977-09-06	Dibenzofuran-2,3,6,7-tetracarboxylic acid dianhydride
JP3272284B2 (ja)	2002-04-08	ポリ（置換ビフェニレンビニレン）類及びその製造法
Choi et al.	2004	Synthesis and Characterization of New Aromatic Polyamides with N, N′‐Di (4‐n‐alkylphenyl) benzodiimide Unit on the Main Chain
KR20000002144A (ko)	2000-01-15	3,6-비스[4-(알킬옥시)페닐옥시]파이로멜리트산 이무수물 및 그제조방법
Pourjavadi et al.	2000	Partially aromatic polyamides based on tetraphenylthiophene diamine: synthesis and characterization
JPS61159423A (ja)	1986-07-19	細工しやすい電気的活性ポリマ−
Abdolmaleki et al.	2009	Synthesis of some new polyhydrazides by direct polycondensation in ionic liquid and their metallization through transition metal complexation