CA2092837C - Charge mosaic membrane and production process thereof - Google Patents

Charge mosaic membrane and production process thereof

Info

Publication number: CA2092837C
Authority: CA; Canada
Prior art keywords: polymer; cationic; spheres; anionic; anionic polymers
Prior art date: 1992-09-25
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

CA 2092837

Other languages

English (en)

French (fr)

Other versions

CA2092837A1 (en

Inventor

Takashi Fukutomi

Minoru Takizawa

Michiei Nakamura

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.)

Dainichiseika Color and Chemicals Mfg Co Ltd

Original Assignee

Individual

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.)

1992-09-25

Filing date

1993-03-29

Publication date

1998-06-16

1993-03-29 Application filed by Individual filed Critical Individual

1994-03-26 Publication of CA2092837A1 publication Critical patent/CA2092837A1/en

1998-06-16 Application granted granted Critical

1998-06-16 Publication of CA2092837C publication Critical patent/CA2092837C/en

2013-03-29 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000012528 membrane Substances 0.000 title claims abstract description 58
238000004519 manufacturing process Methods 0.000 title abstract description 13
229920006317 cationic polymer Polymers 0.000 claims abstract description 43
229920006318 anionic polymer Polymers 0.000 claims abstract description 42
125000002091 cationic group Chemical group 0.000 claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 20
230000008569 process Effects 0.000 claims abstract description 20
229920000642 polymer Polymers 0.000 claims description 61
-1 poly(diethylaminoethyl methacrylate) Chemical class 0.000 claims description 29
239000000178 monomer Substances 0.000 claims description 22
239000006185 dispersion Substances 0.000 claims description 18
239000011258 core-shell material Substances 0.000 claims description 10
238000005266 casting Methods 0.000 claims description 8
229920001577 copolymer Chemical class 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 7
239000011369 resultant mixture Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
238000011049 filling Methods 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 2
229920002717 polyvinylpyridine Polymers 0.000 claims description 2
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical class CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims 1
LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical class [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 claims 1
239000003792 electrolyte Substances 0.000 abstract description 31
238000000926 separation method Methods 0.000 abstract description 8
238000010612 desalination reaction Methods 0.000 abstract description 5
210000004379 membrane Anatomy 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 11
238000006116 polymerization reaction Methods 0.000 description 11
238000009740 moulding (composite fabrication) Methods 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000004745 nonwoven fabric Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000000502 dialysis Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
229940117913 acrylamide Drugs 0.000 description 6
125000000129 anionic group Chemical group 0.000 description 6
229920000075 poly(4-vinylpyridine) Polymers 0.000 description 6
239000000047 product Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
229920001400 block copolymer Polymers 0.000 description 5
MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
229940116441 divinylbenzene Drugs 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
229920000831 ionic polymer Polymers 0.000 description 3
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
238000011033 desalting Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
229920003228 poly(4-vinyl pyridine) Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VIJWDMKYWXPRLI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;prop-2-enamide Chemical compound NC(=O)C=C.C=CC1=CC=CC=C1C=C VIJWDMKYWXPRLI-UHFFFAOYSA-N 0.000 description 1
VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
OIQCMCUFGWKBBV-UHFFFAOYSA-N 2,3-diiodobutane Chemical compound CC(I)C(C)I OIQCMCUFGWKBBV-UHFFFAOYSA-N 0.000 description 1
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
AOESAXAWXYJFNC-UHFFFAOYSA-N bis(prop-2-enyl) propanedioate Chemical compound C=CCOC(=O)CC(=O)OCC=C AOESAXAWXYJFNC-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
125000003010 ionic group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000013535 sea water Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000012360 testing method Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1

Landscapes

Processes Of Treating Macromolecular Substances (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Separation Using Semi-Permeable Membranes (AREA)

CA 2092837 1992-09-25 1993-03-29 Charge mosaic membrane and production process thereof Expired - Fee Related CA2092837C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP279248/1992		1992-09-25
JP4279248A JP3016406B2 (ja)	1992-09-25	1992-09-25	コア−シェル型ポリマー及びその製造方法
JP76435/1993		1993-03-11

Publications (2)

Publication Number	Publication Date
CA2092837A1 CA2092837A1 (en)	1994-03-26
CA2092837C true CA2092837C (en)	1998-06-16

Family

ID=17608507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2092837 Expired - Fee Related CA2092837C (en)	1992-09-25	1993-03-29	Charge mosaic membrane and production process thereof

Country Status (2)

Country	Link
JP (1)	JP3016406B2 (ja)
CA (1)	CA2092837C (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7604746B2 (en) *	2004-04-27	2009-10-20	Mcmaster University	Pervaporation composite membranes

1992
- 1992-09-25 JP JP4279248A patent/JP3016406B2/ja not_active Expired - Fee Related
1993
- 1993-03-29 CA CA 2092837 patent/CA2092837C/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH06107798A (ja)	1994-04-19
CA2092837A1 (en)	1994-03-26
JP3016406B2 (ja)	2000-03-06

Legal Events

Date	Code	Title	Description
1993-07-16	EEER	Examination request
2011-03-29	MKLA	Lapsed

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