DE2457328A1 - Verfahren zur herstellung von polyelektrolyten - Google Patents

Verfahren zur herstellung von polyelektrolyten

Info

Publication number: DE2457328A1
Authority: DE; Germany
Prior art keywords: polymer; groups; polymers; solution; formula
Prior art date: 1973-12-04
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.): Pending

Application number

DE19742457328

Other languages

German (de)

English (en)

Inventor

Xavier Marze

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.)

Rhone Poulenc SA

Original Assignee

Rhone Poulenc SA

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.)

1973-12-04

Filing date

1974-12-04

Publication date

1975-06-05

1974-12-04 Application filed by Rhone Poulenc SA filed Critical Rhone Poulenc SA

1975-06-05 Publication of DE2457328A1 publication Critical patent/DE2457328A1/de

Status Pending legal-status Critical Current

Links

229920000867 polyelectrolyte Polymers 0.000 title claims description 40
238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title claims description 9
229920000642 polymer Polymers 0.000 claims description 100
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000000843 powder Substances 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
239000000178 monomer Substances 0.000 claims description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 13
229920013730 reactive polymer Polymers 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 8
125000000542 sulfonic acid group Chemical group 0.000 claims description 8
150000003512 tertiary amines Chemical group 0.000 claims description 7
238000006116 polymerization reaction Methods 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
230000003042 antagnostic effect Effects 0.000 claims description 2
239000012456 homogeneous solution Substances 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
239000007791 liquid phase Substances 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
-1 oxyl groups Chemical group 0.000 description 52
239000000243 solution Substances 0.000 description 40
239000002253 acid Substances 0.000 description 22
239000012528 membrane Substances 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 18
125000004433 nitrogen atom Chemical group N* 0.000 description 17
150000003254 radicals Chemical class 0.000 description 17
229920001577 copolymer Polymers 0.000 description 13
239000000047 product Substances 0.000 description 13
150000002009 diols Chemical class 0.000 description 10
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
150000004985 diamines Chemical class 0.000 description 8
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
229920000447 polyanionic polymer Polymers 0.000 description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000001991 dicarboxylic acids Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000000129 anionic group Chemical group 0.000 description 4
125000002091 cationic group Chemical group 0.000 description 4
239000003792 electrolyte Substances 0.000 description 4
239000004744 fabric Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
238000000108 ultra-filtration Methods 0.000 description 4
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
230000015271 coagulation Effects 0.000 description 3
238000005345 coagulation Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000003010 ionic group Chemical group 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002156 mixing Methods 0.000 description 3
150000002763 monocarboxylic acids Chemical class 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000006277 sulfonation reaction Methods 0.000 description 3
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
229920001567 vinyl ester resin Polymers 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
HAZOZRAPGZDOEM-UHFFFAOYSA-N 2-aminoacetohydrazide Chemical compound NCC(=O)NN HAZOZRAPGZDOEM-UHFFFAOYSA-N 0.000 description 2
XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
102000016943 Muramidase Human genes 0.000 description 2
108010014251 Muramidase Proteins 0.000 description 2
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
159000000032 aromatic acids Chemical class 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
150000007860 aryl ester derivatives Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
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 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000011872 intimate mixture Substances 0.000 description 2
229960000274 lysozyme Drugs 0.000 description 2
235000010335 lysozyme Nutrition 0.000 description 2
239000004325 lysozyme Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000005956 quaternization reaction Methods 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
TXGIGOWYWCOULW-UHFFFAOYSA-N 1,1,1-trihydroxy-2-phenylbut-3-ene-2-sulfonic acid Chemical class C(=C)C(C(O)(O)O)(S(=O)(=O)O)C1=CC=CC=C1 TXGIGOWYWCOULW-UHFFFAOYSA-N 0.000 description 1
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
MMBPSOJWYRIRMS-UHFFFAOYSA-N 1-chloro-1-phenylbut-3-ene-1-sulfonic acid Chemical class C=CCC(Cl)(S(=O)(=O)O)C1=CC=CC=C1 MMBPSOJWYRIRMS-UHFFFAOYSA-N 0.000 description 1
OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
WOYXYKGNQSTRGZ-UHFFFAOYSA-N 1-hydroxy-1-phenylprop-2-ene-1-sulfonic acid Chemical class C=CC(O)(S(O)(=O)=O)C1=CC=CC=C1 WOYXYKGNQSTRGZ-UHFFFAOYSA-N 0.000 description 1
LYDHLGJJJAWBDY-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatocyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(N=C=O)CCC1C(C)(C)C1CCC(N=C=O)CC1 LYDHLGJJJAWBDY-UHFFFAOYSA-N 0.000 description 1
ZCHMCDBADMAKNR-UHFFFAOYSA-N 1-methyl-2h-pyrimidine-2,4-dicarboxylic acid Chemical compound CN1C=CC(C(O)=O)=NC1C(O)=O ZCHMCDBADMAKNR-UHFFFAOYSA-N 0.000 description 1
NFBWGYJLXCERPW-UHFFFAOYSA-N 1-methylimidazole-2,4-dicarboxylic acid Chemical compound CN1C(=NC(=C1)C(=O)O)C(=O)O NFBWGYJLXCERPW-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
UBPFKSSDARNMNX-UHFFFAOYSA-N 2,3-dichloro-4-ethenylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=C(Cl)C(Cl)=C(C=C)C2=C1 UBPFKSSDARNMNX-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
ZLSCHGRWXSMZBB-UHFFFAOYSA-N 2-(1,2,2-trihydroxyethenyl)benzenesulfonic acid Chemical class OC(O)=C(O)C1=CC=CC=C1S(O)(=O)=O ZLSCHGRWXSMZBB-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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 1
LAPBGYCFKYEWQX-UHFFFAOYSA-N 2-(dimethylamino)terephthalic acid Chemical compound CN(C)C1=CC(C(O)=O)=CC=C1C(O)=O LAPBGYCFKYEWQX-UHFFFAOYSA-N 0.000 description 1
WFAJUCNUFIIUDH-UHFFFAOYSA-N 2-(methylamino)hexanedioic acid Chemical compound CNC(C(O)=O)CCCC(O)=O WFAJUCNUFIIUDH-UHFFFAOYSA-N 0.000 description 1
XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
BBJJJPPTYKZIJP-UHFFFAOYSA-N 2-ethenoxybenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1OC=C BBJJJPPTYKZIJP-UHFFFAOYSA-N 0.000 description 1
YRPYTFXEHXXYQW-UHFFFAOYSA-N 2-ethenyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C=C)=NC2=C1 YRPYTFXEHXXYQW-UHFFFAOYSA-N 0.000 description 1
XHCCPUQVFMEKIZ-UHFFFAOYSA-N 2-ethenyl-4,6-dimethylpyridine Chemical compound CC1=CC(C)=NC(C=C)=C1 XHCCPUQVFMEKIZ-UHFFFAOYSA-N 0.000 description 1
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LCFYCLRCIJDYQD-UHFFFAOYSA-N 2-ethenyl-5-methylpyridine Chemical compound CC1=CC=C(C=C)N=C1 LCFYCLRCIJDYQD-UHFFFAOYSA-N 0.000 description 1
VMWGBWNAHAUQIO-UHFFFAOYSA-N 2-ethenyl-6-methylpyridine Chemical compound CC1=CC=CC(C=C)=N1 VMWGBWNAHAUQIO-UHFFFAOYSA-N 0.000 description 1
FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
OBNZQBVPDZWAEB-UHFFFAOYSA-N 2-phenylprop-1-ene-1-sulfonic acid Chemical class OS(=O)(=O)C=C(C)C1=CC=CC=C1 OBNZQBVPDZWAEB-UHFFFAOYSA-N 0.000 description 1
SMFDSFRYWRBNSQ-UHFFFAOYSA-N 2-prop-1-en-2-ylbenzenesulfonic acid Chemical class CC(=C)C1=CC=CC=C1S(O)(=O)=O SMFDSFRYWRBNSQ-UHFFFAOYSA-N 0.000 description 1
BHDBDYGQQIHGSV-UHFFFAOYSA-N 2-propan-2-yl-6-prop-1-en-2-ylbenzenesulfonic acid Chemical class CC(C)C1=CC=CC(C(C)=C)=C1S(O)(=O)=O BHDBDYGQQIHGSV-UHFFFAOYSA-N 0.000 description 1
DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
AZEJERVTHQBAJI-UHFFFAOYSA-N 3-morpholin-4-ylhexane-1,6-diamine Chemical compound NCCCC(CCN)N1CCOCC1 AZEJERVTHQBAJI-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
OZUBMBIDHPBIDL-UHFFFAOYSA-N 4-Propylcyclohexylamine Chemical compound CCCC1CCC(N)CC1 OZUBMBIDHPBIDL-UHFFFAOYSA-N 0.000 description 1
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
UMKWZZPKADNTRP-UHFFFAOYSA-N 4-ethenylpyrimidine Chemical compound C=CC1=CC=NC=N1 UMKWZZPKADNTRP-UHFFFAOYSA-N 0.000 description 1
VFRRWVCMOFUSPN-UHFFFAOYSA-N 4-methylhexane-3,3-diol Chemical compound CCC(C)C(O)(O)CC VFRRWVCMOFUSPN-UHFFFAOYSA-N 0.000 description 1
CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 description 1
VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-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 compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
230000002965 anti-thrombogenic effect Effects 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000007265 chloromethylation reaction Methods 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
LBVWYGNGGJURHQ-UHFFFAOYSA-N dicarbon Chemical compound [C-]#[C+] LBVWYGNGGJURHQ-UHFFFAOYSA-N 0.000 description 1
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
VFIJKQJHCCRWHE-UHFFFAOYSA-N hex-1-ene-1-sulfonic acid Chemical class CCCCC=CS(O)(=O)=O VFIJKQJHCCRWHE-UHFFFAOYSA-N 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000002649 leather substitute Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
238000005259 measurement Methods 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
DOSWHECVUKBMCG-UHFFFAOYSA-N n'-phenylpropane-1,3-diamine Chemical compound NCCCNC1=CC=CC=C1 DOSWHECVUKBMCG-UHFFFAOYSA-N 0.000 description 1
GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
DPLUMPJQXVYXBH-UHFFFAOYSA-N n,n-diethyl-2-phenylethenamine Chemical compound CCN(CC)C=CC1=CC=CC=C1 DPLUMPJQXVYXBH-UHFFFAOYSA-N 0.000 description 1
JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
AZKITALDHMWFLI-UHFFFAOYSA-N n,n-dimethyl-4-methylideneheptan-3-amine Chemical compound CCCC(=C)C(CC)N(C)C AZKITALDHMWFLI-UHFFFAOYSA-N 0.000 description 1
NINOYJQVULROET-UHFFFAOYSA-N n,n-dimethylethenamine Chemical compound CN(C)C=C NINOYJQVULROET-UHFFFAOYSA-N 0.000 description 1
GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
IQFXJRXOTKFGPN-UHFFFAOYSA-N n-ethenyl-n-ethylethanamine Chemical compound CCN(CC)C=C IQFXJRXOTKFGPN-UHFFFAOYSA-N 0.000 description 1
WRLBVBBEFRWHHT-UHFFFAOYSA-N n-propan-2-yl-n-prop-2-enylpropan-2-amine Chemical compound CC(C)N(C(C)C)CC=C WRLBVBBEFRWHHT-UHFFFAOYSA-N 0.000 description 1
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
MSIBHARACSILSI-UHFFFAOYSA-N oct-5-en-1-amine Chemical compound CCC=CCCCCN MSIBHARACSILSI-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
BIYCHPUIIDCAPR-UHFFFAOYSA-N pent-2-ene-2-sulfonic acid Chemical class CCC=C(C)S(O)(=O)=O BIYCHPUIIDCAPR-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000012466 permeate Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000110 poly(aryl ether sulfone) Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical group S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/80—Block polymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
- C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2340/00—Filter material

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Separation Using Semi-Permeable Membranes (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Compositions Of Macromolecular Compounds (AREA)
Secondary Cells (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Paints Or Removers (AREA)

DE19742457328 1973-12-04 1974-12-04 Verfahren zur herstellung von polyelektrolyten Pending DE2457328A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7343242A FR2252862B1 (ru)	1973-12-04	1973-12-04
FR7426738A FR2280684A1 (fr)	1973-12-04	1974-08-01	Procede de preparation de polyelectrolytes

Publications (1)

Publication Number	Publication Date
DE2457328A1 true DE2457328A1 (de)	1975-06-05

Family

ID=26218065

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE2457355A Expired DE2457355C3 (de)	1973-12-04	1974-12-04	Semipermeable Membranen
DE19742457328 Pending DE2457328A1 (de)	1973-12-04	1974-12-04	Verfahren zur herstellung von polyelektrolyten

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
DE2457355A Expired DE2457355C3 (de)	1973-12-04	1974-12-04	Semipermeable Membranen

Country Status (14)

Country	Link
JP (1)	JPS50105735A (ru)
BE (2)	BE822901A (ru)
BR (1)	BR7410097A (ru)
CH (1)	CH589678A5 (ru)
DE (2)	DE2457355C3 (ru)
DK (1)	DK627974A (ru)
ES (1)	ES432558A1 (ru)
FR (2)	FR2252862B1 (ru)
GB (2)	GB1473857A (ru)
IL (1)	IL46177A (ru)
IT (1)	IT1026766B (ru)
LU (2)	LU71412A1 (ru)
NL (2)	NL7415424A (ru)
SU (1)	SU575034A3 (ru)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996005235A1 (de) *	1994-08-12	1996-02-22	Basf Aktiengesellschaft	Mesomorphe komplexe aus polyelektrolyten und tensiden, verfahren zu ihrer herstellung sowie filme, folien, fasern, formkörper und beschichtungen hieraus
WO2000015674A1 (de) *	1998-09-10	2000-03-23	Basf Coatings Ag	Feststoffe auf der basis mesomorpher polyelektrolytkomplexe, verfahren zu ihrer herstellung und ihre verwendung

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2286851A1 (fr) *	1974-10-02	1976-04-30	Inst Nat Rech Chimique	Membranes en polyacrylamide reticule ou en polyacrylamide substitue reticule, leur fabrication et leur application
US4005012A (en) *	1975-09-22	1977-01-25	The United States Of America As Represented By The Secretary Of The Interior	Semipermeable membranes and the method for the preparation thereof
LU76955A1 (ru) *	1977-03-15	1978-10-18
US4125462A (en) *	1977-08-30	1978-11-14	Rohm And Haas Company	Coated membranes
JPS5554004A (en) *	1978-10-18	1980-04-21	Teijin Ltd	Selective permeable membrane and its manufacturing
EP0056175B1 (en) *	1981-01-13	1985-05-02	Teijin Limited	Ion-permeable composite membrane and its use in selective separation
LU83350A1 (fr) *	1981-05-08	1983-03-24	Oreal	Composition destinee au traitement des fibres keratiniques a base de polymere cationique et de polymere anionique a groupements vinylsulfoniques et procede de traitement la mettant en oeuvre
US4415608A (en) *	1982-01-15	1983-11-15	Uop Inc.	Continuous production of polymethylpentene membranes
CH656626A5 (fr) *	1982-02-05	1986-07-15	Pall Corp	Membrane en polyamide, presentant des proprietes de surface controlees, son utilisation et son procede de preparation.
US4707266A (en) *	1982-02-05	1987-11-17	Pall Corporation	Polyamide membrane with controlled surface properties
US4427419A (en) *	1982-03-12	1984-01-24	The Standard Oil Company	Semipermeable membranes prepared from polymers containing pendent sulfone groups
US4539373A (en) *	1982-07-12	1985-09-03	The Dow Chemical Company	Thermoplastic polyelectrolyte complexes
US4806189A (en) *	1984-08-13	1989-02-21	Monsanto Company	Composite fluid separation membranes
US4717395A (en) *	1986-08-07	1988-01-05	The Dow Chemical Company	Gas separations using membranes comprising sulphonated polyether sulphone
JP2694341B2 (ja) *	1987-02-04	1997-12-24	ハイドロノーティクス	改良された耐酸化性膜およびその製造方法
US4990252A (en) *	1987-02-04	1991-02-05	Hydanautics	Stable membranes from sulfonated polyarylethers
US4840819A (en) *	1987-04-08	1989-06-20	Union Carbide Corporation	Method for preparing composite membranes for enhanced gas separation
US4826599A (en) *	1987-07-10	1989-05-02	Union Carbide Corporation	Composite membranes and their manufacture and use
JPH01215348A (ja) *	1988-02-25	1989-08-29	Asahi Glass Co Ltd	陽イオン交換体
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FR1493044A (fr) *	1966-07-13	1967-08-25		Nouveaux copolymères non caoutchouteux
BE785741A (fr) *	1971-07-02	1973-01-02	Rhone Poulenc Sa	Polyelectrolytes

1973
- 1973-12-04 FR FR7343242A patent/FR2252862B1/fr not_active Expired
1974
- 1974-08-01 FR FR7426738A patent/FR2280684A1/fr active Granted
- 1974-11-26 NL NL7415424A patent/NL7415424A/xx not_active Application Discontinuation
- 1974-11-26 NL NL7415419A patent/NL7415419A/xx not_active Application Discontinuation
- 1974-12-03 GB GB5227074A patent/GB1473857A/en not_active Expired
- 1974-12-03 GB GB5226574A patent/GB1463175A/en not_active Expired
- 1974-12-03 BR BR10097/74A patent/BR7410097A/pt unknown
- 1974-12-03 IL IL46177A patent/IL46177A/en unknown
- 1974-12-03 BE BE151114A patent/BE822901A/xx unknown
- 1974-12-03 BE BE151115A patent/BE822902A/xx unknown
- 1974-12-03 SU SU7402082929A patent/SU575034A3/ru active
- 1974-12-03 LU LU71412A patent/LU71412A1/xx unknown
- 1974-12-03 DK DK627974A patent/DK627974A/da unknown
- 1974-12-03 JP JP49139351A patent/JPS50105735A/ja active Pending
- 1974-12-03 CH CH1604474A patent/CH589678A5/xx not_active IP Right Cessation
- 1974-12-03 LU LU71413A patent/LU71413A1/xx unknown
- 1974-12-03 IT IT30150/74A patent/IT1026766B/it active
- 1974-12-04 DE DE2457355A patent/DE2457355C3/de not_active Expired
- 1974-12-04 DE DE19742457328 patent/DE2457328A1/de active Pending
- 1974-12-04 ES ES432558A patent/ES432558A1/es not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996005235A1 (de) *	1994-08-12	1996-02-22	Basf Aktiengesellschaft	Mesomorphe komplexe aus polyelektrolyten und tensiden, verfahren zu ihrer herstellung sowie filme, folien, fasern, formkörper und beschichtungen hieraus
WO2000015674A1 (de) *	1998-09-10	2000-03-23	Basf Coatings Ag	Feststoffe auf der basis mesomorpher polyelektrolytkomplexe, verfahren zu ihrer herstellung und ihre verwendung

Also Published As

Publication number	Publication date
BR7410097A (pt)	1976-06-08
IL46177A (en)	1977-05-31
IL46177A0 (en)	1975-03-13
ES432558A1 (es)	1977-03-01
LU71412A1 (ru)	1975-08-20
NL7415424A (nl)	1975-06-06
CH589678A5 (ru)	1977-07-15
DE2457355B2 (de)	1979-08-02
FR2280684A1 (fr)	1976-02-27
FR2280684B1 (ru)	1977-03-18
DE2457355A1 (de)	1975-06-05
DE2457355C3 (de)	1980-04-03
FR2252862B1 (ru)	1978-10-27
GB1473857A (en)	1977-05-18
JPS50105735A (ru)	1975-08-20
IT1026766B (it)	1978-10-20
DK627974A (ru)	1975-07-28
LU71413A1 (ru)	1975-08-20
FR2252862A1 (ru)	1975-06-27
BE822902A (fr)	1975-06-03
GB1463175A (en)	1977-02-02
SU575034A3 (ru)	1977-09-30
BE822901A (fr)	1975-06-03
NL7415419A (nl)	1975-06-06

Legal Events

Date	Code	Title	Description
1980-09-11	OD	Request for examination

Publication	Publication Date	Title
DE2457328A1 (de)	1975-06-05	Verfahren zur herstellung von polyelektrolyten
DE3750444T2 (de)	1994-12-22	Bipolare Membrane und Verfahren zur Herstellung derselben.
DE102009020232B4 (de)	2015-11-19	Sulfonierte Polyperfluorcyclobutan-Polyphenylen-Polymere für PEM-Brennstoffzellenanwendungen
DE68928832T2 (de)	1999-03-04	Anionenaustauscher
DE60214684T2 (de)	2007-09-06	Anionenaustauscher und Verfahren zur Herstellung einer Anionenaustauschmembran
DE2307730A1 (de)	1973-08-23	Ionische mikrokapseln
WO2000009588A1 (de)	2000-02-24	Modifikation von engineeringpolymeren mit n-basischen gruppen und mit ionenaustauschergruppen in der seitenkette
DE102014009170A1 (de)	2015-12-17	Kombinatorisches Materialsystem für Ionenaustauschermembranen und dessen Verwendung in elektrochemischen Prozessen
DE2437395A1 (de)	1975-04-17	N-monosubstituierte sulfonamidogruppen enthaltende fluorhaltige ionenaustauschende polymere
EP1373364B1 (de)	2006-08-23	Sulfoniertes polyetherketonketon
DE112012005418B4 (de)	2018-06-21	Verfahren zur Herstellung eines sulfonierten aromatischen Polymers
DE60121929T2 (de)	2007-09-06	Verfahren und apparatur zur herstellung von polyanilin
DE4328226A1 (de)	1995-03-02	Stark basische Anionenaustauschermembran und Verfahren zu deren Herstellung
EP0257225B1 (de)	1990-12-27	Wärmesensible Polyurethan-dispersionen
DE2825247A1 (de)	1978-12-14	Permselektive zusammengesetzte membran und verfahren zu deren herstellung
DE60014713T2 (de)	2005-10-13	Membranen aus Pfropfpolymeren und Ionenaustauschmenbranen daraus
DE2323189C2 (de)	1981-12-10	Verfahren zum Herstellen von löslichen Polyionkomplexen
DE3537739A1 (de)	1986-04-30	Elektrodialyse-membran, verfahren zu ihrer herstellung und ihre verwendung
DE69330933T2 (de)	2002-04-04	Verfahren zur Herstellung geladener Mosaikmembranen
DE2232204A1 (de)	1973-01-11	Polyelektrolyte
DE2646655A1 (de)	1977-06-02	Schwefelhaltige, fuer membranen geeignete, polymere
DE2149202A1 (de)	1972-04-06	Acrylnitrilcopolymere
DE4211266C2 (de)	1996-12-19	Nicht-poröse, flächige oder faserförmige Polymergebilde mit hydrophiler Oberfläche und deren Verwendung als Membranen für die Dialyse oder Elektrodialyse
WO2009083509A1 (de)	2009-07-09	Polymere auf der basis von polydiallylammoniumverbindungen, anionenaustauschermembranen enthaltend die polymere und deren verwendung in brennstoffzellen
DE2003704A1 (de)	1970-08-13	Neue Anionenaustauscher und ihre Herstellung

DE2457328A1 - Verfahren zur herstellung von polyelektrolyten - Google Patents

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