IL89970A - Composite membranes containing a coated layer of crosslinked polyaromatic polymers and/or sulfonated poly (haloalkylenes) - Google Patents
Composite membranes containing a coated layer of crosslinked polyaromatic polymers and/or sulfonated poly (haloalkylenes)Info
- Publication number
- IL89970A IL89970A IL8997089A IL8997089A IL89970A IL 89970 A IL89970 A IL 89970A IL 8997089 A IL8997089 A IL 8997089A IL 8997089 A IL8997089 A IL 8997089A IL 89970 A IL89970 A IL 89970A
- Authority
- IL
- Israel
- Prior art keywords
- group
- membrane
- membrane according
- crosslinked
- composite membrane
- Prior art date
Links
- 239000012528 membrane Substances 0.000 title claims abstract description 266
- 239000002131 composite material Substances 0.000 title claims abstract description 33
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 title claims description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 58
- 238000000576 coating method Methods 0.000 claims abstract description 58
- 229920000642 polymer Chemical group 0.000 claims abstract description 57
- 239000000758 substrate Substances 0.000 claims abstract description 15
- 238000011065 in-situ storage Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 51
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 43
- 239000002033 PVDF binder Substances 0.000 claims description 41
- -1 alkali metal alkoxide Chemical class 0.000 claims description 39
- 238000004132 cross linking Methods 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 18
- 229920002492 poly(sulfone) Polymers 0.000 claims description 17
- 125000004970 halomethyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 238000000108 ultra-filtration Methods 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229920006393 polyether sulfone Polymers 0.000 claims description 14
- 239000011148 porous material Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 238000001471 micro-filtration Methods 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 13
- 238000001223 reverse osmosis Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 7
- 150000008360 acrylonitriles Chemical class 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 229910002804 graphite Inorganic materials 0.000 claims description 6
- 239000010439 graphite Substances 0.000 claims description 6
- 230000003204 osmotic effect Effects 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- 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 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 4
- 239000012510 hollow fiber Substances 0.000 claims description 4
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 3
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 5
- 229910017053 inorganic salt Inorganic materials 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
- 230000009471 action Effects 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 230000004907 flux Effects 0.000 description 25
- 238000007654 immersion Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 17
- 229920001688 coating polymer Polymers 0.000 description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 9
- 229930006000 Sucrose Natural products 0.000 description 9
- 238000005266 casting Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 239000005720 sucrose Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229940073584 methylene chloride Drugs 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 7
- 239000004695 Polyether sulfone Substances 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 150000004703 alkoxides Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920006380 polyphenylene oxide Polymers 0.000 description 6
- 238000005956 quaternization reaction Methods 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 239000000919 ceramic Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229940086542 triethylamine Drugs 0.000 description 5
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920002307 Dextran Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000004775 Tyvek Substances 0.000 description 3
- 229920000690 Tyvek Polymers 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- ICMZFZGUTLNLAJ-UHFFFAOYSA-N 2,6-dimethyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound CC1=CC=CC2(C)OC12 ICMZFZGUTLNLAJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000005056 compaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012633 leachable Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 239000012982 microporous membrane Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- JEKLNUVCTRHZFZ-UHFFFAOYSA-N 2-methylideneoctanenitrile Chemical compound CCCCCCC(=C)C#N JEKLNUVCTRHZFZ-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-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
- JHUFGBSGINLPOW-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)benzoyl cyanide Chemical compound FC(F)(F)OC1=CC=C(C(=O)C#N)C=C1Cl JHUFGBSGINLPOW-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 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
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GZORJAFFPJJJQU-UHFFFAOYSA-N n,n-dimethylacetamide;1-methylpyrrolidin-2-one Chemical compound CN(C)C(C)=O.CN1CCCC1=O GZORJAFFPJJJQU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical class [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- ZSBJCQGJFPHZRC-UHFFFAOYSA-N prop-2-enyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC=C)C=C1 ZSBJCQGJFPHZRC-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
- B01D67/00931—Chemical modification by introduction of specific groups after membrane formation, e.g. by grafting
-
- 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
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- 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
- B01D71/40—Polymers of unsaturated acids or derivatives thereof, e.g. salts, amides, imides, nitriles, anhydrides, esters
- B01D71/42—Polymers of nitriles, e.g. polyacrylonitrile
- B01D71/421—Polyacrylonitrile
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Transplantation (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Materials For Medical Uses (AREA)
- Organic Insulating Materials (AREA)
- Formation Of Insulating Films (AREA)
- Non-Alcoholic Beverages (AREA)
- Artificial Filaments (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL8997089A IL89970A (en) | 1989-04-14 | 1989-04-14 | Composite membranes containing a coated layer of crosslinked polyaromatic polymers and/or sulfonated poly (haloalkylenes) |
| IL93886A IL93886A0 (en) | 1989-04-14 | 1990-03-26 | Composite membrane and its use |
| EP93111792A EP0574957B1 (de) | 1989-04-14 | 1990-04-10 | Aus Acrylnitril und Polyvinylidenfluorid abgeleitete Membranen |
| DE69014967T DE69014967T2 (de) | 1989-04-14 | 1990-04-10 | Lösungsmittelbeständige Membranen. |
| DE69033886T DE69033886T2 (de) | 1989-04-14 | 1990-04-10 | Aus Acrylnitril und Polyvinylidenfluorid abgeleitete Membranen |
| EP90810287A EP0392982B1 (de) | 1989-04-14 | 1990-04-10 | Lösungsmittelbeständige Membranen |
| DE69024088T DE69024088T2 (de) | 1989-04-14 | 1990-04-10 | Beschichtete Membranen |
| AT93111792T ATE211408T1 (de) | 1989-04-14 | 1990-04-10 | Aus acrylnitril und polyvinylidenfluorid abgeleitete membranen |
| EP90810288A EP0394193B1 (de) | 1989-04-14 | 1990-04-10 | Beschichtete Membranen |
| DK93111792T DK0574957T3 (da) | 1989-04-14 | 1990-04-10 | Acrylonitril- og polyvinylidenfluoridafledte membraner |
| AT90810287T ATE115437T1 (de) | 1989-04-14 | 1990-04-10 | Lösungsmittelbeständige membranen. |
| AT90810288T ATE131411T1 (de) | 1989-04-14 | 1990-04-10 | Beschichtete membranen |
| EP19900810286 EP0421916A3 (en) | 1989-04-14 | 1990-04-10 | Composite membranes and processes using them |
| US07/507,567 US5032282A (en) | 1989-04-14 | 1990-04-11 | Solvent-stable semipermeable composite membranes |
| US07/507,565 US5028337A (en) | 1989-04-14 | 1990-04-11 | Coated membranes |
| JP2099185A JP3020545B2 (ja) | 1989-04-14 | 1990-04-13 | 被覆複合膜 |
| JP09918490A JP3145093B2 (ja) | 1989-04-14 | 1990-04-13 | 溶剤安定複合膜 |
| JP2099183A JPH03118823A (ja) | 1989-04-14 | 1990-04-13 | 複合膜およびその使用法 |
| IL106186A IL106186A0 (en) | 1989-04-14 | 1993-06-30 | Separation processes using crosslinked polyacrylonitrile and related polymers |
| HK98105348A HK1006156A1 (en) | 1989-04-14 | 1998-06-16 | Solvent stable membranes |
| HK98105349A HK1006157A1 (en) | 1989-04-14 | 1998-06-16 | Coated membranes |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL8997089A IL89970A (en) | 1989-04-14 | 1989-04-14 | Composite membranes containing a coated layer of crosslinked polyaromatic polymers and/or sulfonated poly (haloalkylenes) |
| US07/416,224 US5024765A (en) | 1989-10-02 | 1989-10-02 | Composite membranes and processes using them |
| GB8924412A GB2247419B (en) | 1989-10-30 | 1989-10-30 | Semipermeable composite membranes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL89970A0 IL89970A0 (de) | 1989-12-15 |
| IL89970A true IL89970A (en) | 1994-10-21 |
Family
ID=39967322
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8997089A IL89970A (en) | 1989-04-14 | 1989-04-14 | Composite membranes containing a coated layer of crosslinked polyaromatic polymers and/or sulfonated poly (haloalkylenes) |
| IL93886A IL93886A0 (en) | 1989-04-14 | 1990-03-26 | Composite membrane and its use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL93886A IL93886A0 (en) | 1989-04-14 | 1990-03-26 | Composite membrane and its use |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5028337A (de) |
| EP (2) | EP0421916A3 (de) |
| JP (2) | JPH03118823A (de) |
| AT (2) | ATE131411T1 (de) |
| DE (2) | DE69033886T2 (de) |
| DK (1) | DK0574957T3 (de) |
| HK (1) | HK1006157A1 (de) |
| IL (2) | IL89970A (de) |
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| CA2100643A1 (en) * | 1992-08-14 | 1994-02-15 | Guido Sartori | Fluorinated polyolefin membranes for aromatics/saturates separation |
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| US5288304A (en) * | 1993-03-30 | 1994-02-22 | The University Of Texas System | Composite carbon fluid separation membranes |
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| FR2715590B1 (fr) * | 1994-02-01 | 1996-04-12 | Rhone Poulenc Chimie | Procédé d'épuration d'un milieu contenant des déchets organiques. |
| US5700559A (en) * | 1994-12-16 | 1997-12-23 | Advanced Surface Technology | Durable hydrophilic surface coatings |
| US5645766A (en) * | 1995-03-30 | 1997-07-08 | Teijin Limited | Film of aromatic polyethersulfone process for the production thereof and solution composition for the production thereof |
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| US6719147B2 (en) * | 2001-04-27 | 2004-04-13 | The University Of Delaware | Supported mesoporous carbon ultrafiltration membrane and process for making the same |
| US20030224132A1 (en) * | 2001-11-02 | 2003-12-04 | Chien-Chung Han | Assembled structures of carbon tubes and method for making the same |
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| DE102004025443A1 (de) | 2004-05-19 | 2005-12-08 | Basf Ag | Verfahren zur Herstellung einer Flüssigformulierung von Salzen sulfonsaurer Azofarbstoffe |
| AU2006223564A1 (en) * | 2005-03-09 | 2006-09-21 | The Regents Of The University Of California | Nanocomposite membranes and methods of making and using same |
| KR100660182B1 (ko) * | 2005-03-25 | 2006-12-21 | 한국화학연구원 | 아믹산 또는 이미드 측쇄기로 가교된 방향족 폴리에테르계수지 |
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| CA2667579A1 (en) * | 2006-10-27 | 2008-05-15 | The Regents Of The University Of California | Micro-and nanocomposite support structures for reverse osmosis thin film membranes |
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| WO2009039467A1 (en) * | 2007-09-21 | 2009-03-26 | The Regents Of The University Of California | Nanocomposite membranes and methods of making and using same |
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| US8710109B2 (en) | 2009-02-19 | 2014-04-29 | Ben Gurion University Of The Negev Research And Development Authority | Chemically resistant membranes, coatings and films and methods for their preparation |
| WO2011008549A2 (en) * | 2009-06-29 | 2011-01-20 | NanoH2O Inc. | Improved hybrid tfc ro membranes with nitrogen additives |
| DE202009016240U1 (de) | 2009-11-27 | 2010-04-29 | Weihmann, Andreas, Dipl.-Designer | Wassergewinnungssystemtechnologie |
| KR101317640B1 (ko) * | 2010-12-16 | 2013-10-15 | 웅진케미칼 주식회사 | 해수담수용 정삼투막 및 그 제조방법 |
| JP5596784B2 (ja) | 2010-04-30 | 2014-09-24 | ウンジン ケミカル カンパニー，リミテッド | 海水淡水用正浸透膜及びその製造方法 |
| US9839879B2 (en) | 2010-04-30 | 2017-12-12 | Woongjin Chemical Co., Ltd. | Forward osmosis membrane for seawater desalination and method for preparing the same |
| EP2637773B1 (de) | 2010-11-10 | 2019-10-30 | NanoH2O Inc. | Verbesserte hybrid-tfc-ro-membranen mit nichtmetallischen additiven |
| WO2012081026A2 (en) | 2010-12-12 | 2012-06-21 | Ben-Gurion University Of The Negev Research And Development Authority | Anion exchange membranes, methods of preparation and uses |
| US9172076B2 (en) | 2011-01-11 | 2015-10-27 | Etv Energy Ltd. | Membranes suitable for use as separators and electrochemical cells including such separators |
| US10934198B1 (en) * | 2014-02-08 | 2021-03-02 | Mansour S. Bader | Relative non-wettability of a purification membrane |
| CN103998492B (zh) * | 2011-12-22 | 2016-06-22 | 小西化学工业株式会社 | 用于制备磺化芳香族聚合物的方法 |
| CN104548945A (zh) * | 2013-10-23 | 2015-04-29 | 中国石油化工股份有限公司 | 一种提高超滤膜通量的后处理方法 |
| US10384167B2 (en) | 2013-11-21 | 2019-08-20 | Oasys Water LLC | Systems and methods for improving performance of osmotically driven membrane systems |
| CN105873665B (zh) * | 2013-12-02 | 2019-01-01 | 陶氏环球技术有限责任公司 | 用亚硝酸后处理的复合聚酰胺膜 |
| CN104307387B (zh) * | 2014-10-11 | 2017-08-08 | 南京九思高科技有限公司 | 一种聚偏氟乙烯‑六氟丙烯超疏水复合膜及其制备方法 |
| US9861940B2 (en) | 2015-08-31 | 2018-01-09 | Lg Baboh2O, Inc. | Additives for salt rejection enhancement of a membrane |
| US9737859B2 (en) | 2016-01-11 | 2017-08-22 | Lg Nanoh2O, Inc. | Process for improved water flux through a TFC membrane |
| US10155203B2 (en) | 2016-03-03 | 2018-12-18 | Lg Nanoh2O, Inc. | Methods of enhancing water flux of a TFC membrane using oxidizing and reducing agents |
| KR101893461B1 (ko) * | 2016-11-21 | 2018-08-31 | 한국화학연구원 | 음이온 교환막용 용액, 이를 코팅하여 가교하는 제조방법 및 이로 제조된 음이온 교환막 |
| CN110523304A (zh) * | 2019-09-04 | 2019-12-03 | 德蓝水技术股份有限公司 | 一种高通量抗污染特种管式超滤膜的制备方法 |
| US20230099030A1 (en) * | 2020-03-19 | 2023-03-30 | University Of Virginia Patent Foundation | Ion selective membranes for organic electrochemical processes |
| CN112717717B (zh) * | 2020-12-11 | 2022-08-12 | 中化(宁波)润沃膜科技有限公司 | 一种聚砜基膜、含该聚砜基膜的反渗透复合膜及制备方法 |
| CN112844074A (zh) * | 2021-01-15 | 2021-05-28 | 任国峰 | 一种石墨烯复合聚丙烯腈中空纤维膜及其制备方法 |
| CN114272772A (zh) * | 2021-12-31 | 2022-04-05 | 杭州科百特过滤器材有限公司 | 一种除病毒用不对称的pes多孔膜及其制备方法 |
| CN114749035B (zh) * | 2022-04-14 | 2022-12-13 | 浙江美易膜科技有限公司 | 低压大通量中空纤维纳滤膜、其制备方法及其应用 |
| CN114832644B (zh) * | 2022-05-12 | 2023-05-12 | 浙江美易膜科技有限公司 | 含双电层的高通量复合纳滤膜、其制备方法及其应用 |
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| JPS5535910A (en) * | 1978-09-06 | 1980-03-13 | Teijin Ltd | Permselectivity composite membrane and preparation thereof |
| US4277344A (en) * | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
| IL64967A0 (en) * | 1981-03-17 | 1982-04-30 | Aligena Ag | Semipermeable membranes containing modified polysulfones,their manufacture and their use |
| CH660852A5 (de) * | 1982-11-23 | 1987-05-29 | Aligena Ag | Dynamische membranen, die sich als duenne polymerschichten auf poroesen, polymeren traegermaterialien befinden. |
| GB2189168B (en) * | 1986-04-21 | 1989-11-29 | Aligena Ag | Composite membranes useful in the separation of low molecular weight organic compounds from aqueous solutions containing inorganic salts |
| US4812238A (en) * | 1987-01-15 | 1989-03-14 | The Dow Chemical Company | Membranes prepared via reaction of diazonium compounds or precursors |
-
1989
- 1989-04-14 IL IL8997089A patent/IL89970A/en not_active IP Right Cessation
-
1990
- 1990-03-26 IL IL93886A patent/IL93886A0/xx unknown
- 1990-04-10 EP EP19900810286 patent/EP0421916A3/en not_active Withdrawn
- 1990-04-10 AT AT90810288T patent/ATE131411T1/de not_active IP Right Cessation
- 1990-04-10 DE DE69033886T patent/DE69033886T2/de not_active Expired - Lifetime
- 1990-04-10 EP EP90810288A patent/EP0394193B1/de not_active Expired - Lifetime
- 1990-04-10 DE DE69024088T patent/DE69024088T2/de not_active Expired - Fee Related
- 1990-04-10 DK DK93111792T patent/DK0574957T3/da active
- 1990-04-10 AT AT93111792T patent/ATE211408T1/de not_active IP Right Cessation
- 1990-04-11 US US07/507,565 patent/US5028337A/en not_active Expired - Lifetime
- 1990-04-13 JP JP2099183A patent/JPH03118823A/ja active Pending
- 1990-04-13 JP JP2099185A patent/JP3020545B2/ja not_active Expired - Lifetime
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1998
- 1998-06-16 HK HK98105349A patent/HK1006157A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0394193A3 (de) | 1991-01-09 |
| IL89970A0 (de) | 1989-12-15 |
| DK0574957T3 (da) | 2002-04-22 |
| US5028337A (en) | 1991-07-02 |
| EP0394193B1 (de) | 1995-12-13 |
| HK1006157A1 (en) | 1999-02-12 |
| ATE131411T1 (de) | 1995-12-15 |
| JP3020545B2 (ja) | 2000-03-15 |
| EP0421916A2 (de) | 1991-04-10 |
| DE69033886T2 (de) | 2002-08-29 |
| IL93886A0 (en) | 1990-12-23 |
| DE69024088D1 (de) | 1996-01-25 |
| DE69033886D1 (de) | 2002-02-07 |
| EP0394193A2 (de) | 1990-10-24 |
| JPH038423A (ja) | 1991-01-16 |
| DE69024088T2 (de) | 1996-06-13 |
| EP0421916A3 (en) | 1992-10-21 |
| JPH03118823A (ja) | 1991-05-21 |
| ATE211408T1 (de) | 2002-01-15 |
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