JPH0371170B2 - - Google Patents

Info

Publication number: JPH0371170B2
Authority: JP; Japan
Prior art keywords: compound; group; vinyl compound; membrane; compounds
Prior art date: 1985-02-15
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

Application number

JP2617185A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61187904A (ja

Inventor

Juji Konagaya

Koji Fukuda

Shinsuke Takegami

Masao Murano

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.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

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.)

1985-02-15

Filing date

1985-02-15

Publication date

1991-11-12

1985-02-15 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1985-02-15 Priority to JP2617185A priority Critical patent/JPS61187904A/ja

1986-08-21 Publication of JPS61187904A publication Critical patent/JPS61187904A/ja

1991-11-12 Publication of JPH0371170B2 publication Critical patent/JPH0371170B2/ja

Status Granted legal-status Critical Current

Links

-1 vinyl compound Chemical class 0.000 claims description 47
239000012528 membrane Substances 0.000 claims description 34
229920002554 vinyl polymer Polymers 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 23
238000000926 separation method Methods 0.000 claims description 22
229920001577 copolymer Polymers 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
238000004132 cross linking Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000012530 fluid Substances 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000007789 gas Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
230000035699 permeability Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004205 dimethyl polysiloxane Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000010408 film Substances 0.000 description 3
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012466 permeate Substances 0.000 description 3
238000005373 pervaporation Methods 0.000 description 3
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000011243 crosslinked material Substances 0.000 description 2
YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
125000005372 silanol group Chemical group 0.000 description 2
239000000126 substance Substances 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
BOJZPUPAXYETRK-UHFFFAOYSA-N 1,1-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(CN)C1=CC=CC=C1 BOJZPUPAXYETRK-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-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
LBCIPTDSGNETSS-UHFFFAOYSA-N 4-tris(trimethylsilyloxy)silylbutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C LBCIPTDSGNETSS-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
239000002028 Biomass Substances 0.000 description 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-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
239000002202 Polyethylene glycol Substances 0.000 description 1
229910020175 SiOH Inorganic materials 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
IKCXCKOYYOEWOH-UHFFFAOYSA-N [[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C IKCXCKOYYOEWOH-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
PEHLCCGXTLWMRW-UHFFFAOYSA-N bis-lactone Chemical class C1CC2OC(=O)C3C1OC(=O)C32 PEHLCCGXTLWMRW-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
238000002485 combustion reaction Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical class C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
238000004134 energy conservation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
MOSXLDGILGBOSZ-UHFFFAOYSA-N ethenyl-methyl-phenylsilicon Chemical compound C=C[Si](C)C1=CC=CC=C1 MOSXLDGILGBOSZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000446 fuel Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-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
239000012456 homogeneous solution Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ketene group Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000003345 natural gas Substances 0.000 description 1
229940110728 nitrogen / oxygen Drugs 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
SVPYVBAHWDJDAX-UHFFFAOYSA-N silylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[SiH3] SVPYVBAHWDJDAX-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000944 sulfenic acid group Chemical group 0.000 description 1
125000000626 sulfinic acid group Chemical group 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 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
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Separation Using Semi-Permeable Membranes (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Artificial Filaments (AREA)

JP2617185A 1985-02-15 1985-02-15 流体分離用選択透過性架橋膜 Granted JPS61187904A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP2617185A JPS61187904A (ja)	1985-02-15	1985-02-15	流体分離用選択透過性架橋膜

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2617185A JPS61187904A (ja)	1985-02-15	1985-02-15	流体分離用選択透過性架橋膜

Publications (2)

Publication Number	Publication Date
JPS61187904A JPS61187904A (ja)	1986-08-21
JPH0371170B2 true JPH0371170B2 (2)	1991-11-12

Family

ID=12186088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2617185A Granted JPS61187904A (ja)	1985-02-15	1985-02-15	流体分離用選択透過性架橋膜

Country Status (1)

Country	Link
JP (1)	JPS61187904A (2)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4948400A (en) *	1988-06-30	1990-08-14	Nippon Steel Chemical Co., Ltd.	Separation membranes and process for preparing the same
KR101580702B1 (ko) *	2008-03-11	2015-12-28	도레이 카부시키가이샤	복합 분리막
CN102149451B (zh)	2008-09-12	2013-10-16	东丽株式会社	复合半透膜及其制造方法
JP5776274B2 (ja) *	2011-03-31	2015-09-09	東レ株式会社	複合半透膜およびその製造方法
JP6728334B2 (ja) *	2016-03-22	2020-07-22	積水化成品工業株式会社	中空粒子及びその用途
KR102496048B1 (ko) *	2018-03-14	2023-02-06	세키스이가세이힝코교가부시키가이샤	중공 입자 분산체
CN115003712A (zh) *	2020-01-22	2022-09-02	美国陶氏有机硅公司	可固化有机硅-丙烯酸酯组合物、由其制备的导电材料和相关方法

1985
- 1985-02-15 JP JP2617185A patent/JPS61187904A/ja active Granted

Also Published As

Publication number	Publication date
JPS61187904A (ja)	1986-08-21

Legal Events

Date	Code	Title	Description
2005-02-15	EXPY	Cancellation because of completion of term

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