JP6201754B2 - 複合半透膜およびその製造方法 - Google Patents
複合半透膜およびその製造方法 Download PDFInfo
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- JP6201754B2 JP6201754B2 JP2013524177A JP2013524177A JP6201754B2 JP 6201754 B2 JP6201754 B2 JP 6201754B2 JP 2013524177 A JP2013524177 A JP 2013524177A JP 2013524177 A JP2013524177 A JP 2013524177A JP 6201754 B2 JP6201754 B2 JP 6201754B2
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- PUYPTSGXFDZQEP-UHFFFAOYSA-N n-[1,2-dihydroxy-2-(2-methylprop-2-enoylamino)ethyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(O)C(O)NC(=O)C(C)=C PUYPTSGXFDZQEP-UHFFFAOYSA-N 0.000 description 1
- ZMLXKXHICXTSDM-UHFFFAOYSA-N n-[1,2-dihydroxy-2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NC(O)C(O)NC(=O)C=C ZMLXKXHICXTSDM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical group CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical group CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- ZYBHSWXEWOPHBJ-UHFFFAOYSA-N potassium;propan-2-ylbenzene Chemical compound [K+].C[C-](C)C1=CC=CC=C1 ZYBHSWXEWOPHBJ-UHFFFAOYSA-N 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UWHMFGKZAYHMDJ-UHFFFAOYSA-N propane-1,2,3-trithiol Chemical compound SCC(S)CS UWHMFGKZAYHMDJ-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- UUVZTKMMRCCGHN-OUKQBFOZSA-N triethoxy-[(e)-2-phenylethenyl]silane Chemical compound CCO[Si](OCC)(OCC)\C=C\C1=CC=CC=C1 UUVZTKMMRCCGHN-OUKQBFOZSA-N 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical group CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- JPPHEZSCZWYTOP-UHFFFAOYSA-N trimethoxysilylmethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C=C JPPHEZSCZWYTOP-UHFFFAOYSA-N 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-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
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01D71/70—Polymers having silicon in the main chain, with or without sulfur, nitrogen, oxygen or carbon only
-
- 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
- B01D2325/00—Details relating to properties of membranes
- B01D2325/30—Chemical resistance
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/025—Reverse osmosis; Hyperfiltration
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
- C02F1/441—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by reverse osmosis
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
Si(R1)m(R2)n(R3)4−m−n ・・・一般式(a)
(R1はエチレン性不飽和基を含む反応性基を示す。R2はアルコキシ基、アルケニルオキシ基、カルボキシ基、ケトオキシム基、アミノヒドロキシ基、ハロゲン原子またはイソシアネート基のいずれかを表す。R3は水素原子またはアルキル基を表す。m、nはm+n≦4を満たす整数であり、m≧1、n≧1を満たすものとする。R1、R2、R3それぞれにおいて2以上の官能基がケイ素原子に結合している場合、同一であっても異なっていてもよい。)
Si(R1)m(R2)n(R3)4−m−n ・・・一般式(a)
(R1はエチレン性不飽和基を含む反応性基を示す。R2はアルコキシ基、アルケニルオキシ基、カルボキシ基、ケトオキシム基、アミノヒドロキシ基、ハロゲン原子またはイソシアネート基のいずれかを表す。R3は水素原子またはアルキル基を表す。m、nはm+n≦4を満たす整数であり、m≧1、n≧1を満たすものとする。R1、R2、R3それぞれにおいて2以上の官能基がケイ素原子に結合している場合、同一であっても異なっていてもよい。)
Si(R1)m(R2)4−m ・・・一般式(b)
(R1はアルコキシ基、アルケニルオキシ基、カルボキシ基、ケトオキシム基、アミノヒドロキシ基、ハロゲン原子またはイソシアネート基のいずれかを表す。R2は水素原子またはアルキル基を表す。mは1≦m≦4を満たす整数とする。R1、R2それぞれにおいて2以上の官能基がケイ素原子に結合している場合、同一であっても異なっていてもよい。)
L(R)n ・・・一般式(c)
(Rはビニル基、アクリル基、メタクリル基のいずれかを表す。Lは任意の原子団を表す。nは2以上の正の整数とする。)
Rは重合を担う不飽和基であり、Lはその間を結ぶリンカーである。Lの例としては、直鎖アルキル基、分岐アルキル基、フルオロアルキル基とその誘導体、オリゴオキシエチレンとその誘導体、多価アルコール誘導体、多価カルボン酸誘導体、糖誘導体、アルキルアミンとその誘導体、リン酸誘導体、ベンゼン誘導体、シクロヘキサン誘導体、イミダゾール誘導体、ピリジン誘導体、トリアジン誘導体、ヘキサヒドロトリアジン誘導体、シアヌル酸誘導体、イソシアヌル酸誘導体、ボロキシン誘導体、トリシラザン誘導体、シクロテトラシロキサン誘導体などを挙げることができる。
化合物(D)の架橋効果は、重合性官能基の数が多い方が高いため、一般的にはn=2の化合物よりもn≧3の化合物の方が好ましい。n≧3の化合物(D)として、シアヌル酸トリス(2−アクリロイルオキシエチル)、イソシアヌル酸トリス(2−アクリロイルオキシエチル)、1,3,5−トリアクリロイルトリアジン、1,3,5−トリアクリロイルヘキサヒドロ−1,3,5−トリアジン、トリメチロールプロパントリアクリラート、没食子酸トリアクリラート、ペンタエリスリトールトリアクリラート、ピロガロールトリアクリラート、シアヌル酸トリス(2−メタクリロイルオキシエチル)、イソシアヌル酸トリス(2−メタクリロイルオキシエチル)、1,3,5−トリメタクリロイルトリアジン、1,3,5−トリメタクリロイルヘキサヒドロ−1,3,5−トリアジン、トリメチロールプロパントリメタクリラート、没食子酸トリメタクリラート、ペンタエリスリトールトリメタクリラート、2,4,6−トリビニルボロキシン、2,4,6−トリメチル−2,4,6−トリビニルシクロトリシラザン、1,2,4−トリビニルシクロヘキサン、ペンタエリスリトールテトラアクリラート、ペンタエリスリトールテトラメタクリラート、ピロガロールトリアクリラート、2,4,6,8−テトラメチル−2,4,6,8−テトラビニルシクロテトラシロキサン、ジペンタエリスリトールヘキサアクリラート、ジペンタエリスリトールヘキサメタクリラート等が挙げられる。
NaCl除去率(%)={(供給液のNaCl濃度−透過液のNaCl濃度)/供給液のNaCl濃度}×100 ・・・式(d)
溶液の膜透過流束(m3/m2/day)=(一日の透過液量)/(膜面積) ・・・式(e)
純水透過係数(m3/m2/sec/Pa) =(溶液の膜透過流束)/(膜両側の圧力差−膜両側の浸透圧差×溶質反射係数) ・・・式(f)
Jv=Lp(ΔP−σ・Δπ) ・・・式(g)
Js=P(Cm−Cp)+(1−σ)C・Jv ・・・式(h)
ここで、Jvは溶液の膜透過流束(m3/m2/s)、Lpは純水透過係数(m3/m2/s/Pa)、ΔPは膜両側の圧力差(Pa)、σは溶質反射係数、Δπは膜両側の浸透圧差(Pa)、Jsは溶質の膜透過流束(mol/m2/s)、Pは溶質の透過係数(m/s)、Cmは溶質の膜面濃度(mol/m3)、Cpは膜透過液濃度(mol/m3)、Cは膜両側の平均濃度(mol/m3)、である。膜両側の平均濃度Cは、逆浸透膜のように両側の濃度差が非常に大きな場合には実質的な意味を持たない。そこで、式(g)を膜厚について積分した次式がよく用いられる。
R=σ(1−F)/(1−σF) ・・・式(i)
ただし、
F=exp{−(1−σ)Jv/P} ・・・式(j)
であり、Rは真の阻止率で、
R=1−Cp/Cm ・・・式(k)
で定義される。ΔPを種々変化させることにより(g)式からLpを算出でき、またJvを種々変化させてRを測定し、Rと1/Jvをプロットしたものに対して(i)、(j)式をカーブフィッティングすることにより、Pとσを同時に求めることができる。
純水透過係数変化率(day−1)=(23時間通水後の純水透過係数−3時間通水後の純水透過係数)/(3時間通水後の純水透過係数×通水時間) ・・・式(n)
溶質透過係数変化率(day−1)=(23時間通水後の溶質透過係数−3時間通水後の溶質透過係数)/(3時間通水後の溶質透過係数×通水時間) ・・・式(p)
ポリエチレンテレフタレート不織布上にポリスルホンの15.7重量%ジメチルホルムアミド溶液を200μmの厚みで、室温(25℃)でキャストし、ただちに純水中に浸漬して5分間放置することによって微多孔性支持膜を作製した。このようにして得られた微多孔性支持膜の表面の細孔径は21nmであり、厚みは150μmであった。
イソプロピルアルコールの65重量%水溶液中に、化合物(A)に該当する3−アクリロキシプロピルトリメトキシシランを94mM(ミリモーラー)、化合物(B)に該当する4−ビニルフェニルスルホン酸ナトリウムを66mM、化合物(C)に該当するカレンズMTBD1(昭和電工株式会社製)を20mM、光重合開始剤2,2−ジメトキシ−2−フェニルアセトフェノンを8.5mMの濃度で溶解させた。この溶液に、前記の微多孔性支持膜を1分間接触させ、エアーノズルから窒素を吹き付け支持膜表面から余分な溶液を取り除き微多孔性支持膜上に前記溶液の層を形成した。次いで365nmの紫外線が照射できるハリソン東芝ライティング社製UV照射装置TOSCURE(登録商標)752を用い、USHIO社製紫外線積算光量計UIT−250を用いた際の照射強度が20mW/cm2となるように設定し、紫外線を15分間照射して、分離機能層を微多孔性支持膜表面に形成した複合半透膜を作製した。
また、上記条件による加圧膜ろ過運転を継続し、運転開始時から23時間後についても同様に性能評価を行った。通水開始3時間後と23時間後の性能を用いて式(n)から計算した純水透過係数変化率と、式(p)から計算した溶質透過係数変化率についても表1に示す。
実施例1で使用した化合物(C)のカレンズMTBD1(昭和電工株式会社製)をカレンズMTNR1(昭和電工株式会社製)に置き換えた以外は、実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例1で使用した化合物(C)のカレンズMTBD1(昭和電工株式会社製)を1,3,5−トリアジン−2,4,6−トリチオールに置き換えた以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例1で使用した化合物(C)のカレンズMTBD1(昭和電工株式会社製)をカレンズMTPE1(昭和電工株式会社製)に置き換えた以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例2で微多孔性支持膜上に塗布した溶液中に、化合物(D)に該当するグリセロールジアクリラートを10mMとなるように添加した以外は実施例2と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例2で微多孔性支持膜上に塗布した溶液中に、化合物(D)に該当するイソシアヌル酸トリス(2−アクリロイルオキシエチル)を10mMとなるように添加した以外は実施例2と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例2で微多孔性支持膜上に塗布した溶液中に、化合物(D)に該当するペンタエリスリトールテトラメタクリラートを10mMとなるように添加した以外は実施例2と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例2で使用した化合物(C)のカレンズMTNR1(昭和電工株式会社製)を添加しない以外は実施例2と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例2で使用した化合物(C)のカレンズMTNR1(昭和電工株式会社製)をヘキサンチオールに置き換えた以外は実施例2と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例5で使用した化合物(C)のカレンズMTNR1(昭和電工株式会社製)を添加しないこと以外は実施例5と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例6で使用した化合物(C)のカレンズMTNR1(昭和電工株式会社製)を添加しないこと以外は実施例6と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例7で使用した化合物(C)のカレンズMTNR1(昭和電工株式会社製)を添加しないこと以外は実施例7と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例1で使用した化合物(A)の3−アクリロキシプロピルトリメトキシシランを4−ヒドロキシブチルアクリレートに置き換えた以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例1で使用した化合物(B)の4−ビニルフェニルスルホン酸ナトリウムをp−メチルスチレンに置き換えた以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
すなわち、化合物(A)、(B)、(C)または化合物(A)、(B)、(C)、(D)を含む物質から作製した本発明の複合半透膜は、高い分離性能と連続通水運転時の安定性を備えていることが分かる。
Claims (6)
- 微多孔性支持膜上に分離機能層を形成してなり、該分離機能層が、エチレン性不飽和基を有する反応性基と加水分解性基とがケイ素原子に結合した化合物(A)、エチレン性不飽和基を有する反応性基と酸性基を有する化合物(B)、およびチオール基を有する反応性基を2個以上有する化合物(C)を含み且つ上記エチレン性不飽和基に対するチオール基のモル当量が0.01〜1当量であって、化合物(A)、(B)、(C)の混合物を原料として、化合物(A)が有する加水分解性基の縮合、ならびに、化合物(A)および(B)が有するエチレン性不飽和基の重合、ならびに化合物(C)が有するチオール基と化合物(A)および(B)が有するエチレン性不飽和基との付加反応により形成されたものである複合半透膜。
- 微多孔性支持膜上に分離機能層を形成してなり、該分離機能層が、エチレン性不飽和基を有する反応性基と加水分解性基とがケイ素原子に結合した化合物(A)、エチレン性不飽和基を有する反応性基と酸性基を有する化合物(B)、チオール基を有する反応性基を2個以上有する化合物(C)、およびエチレン性不飽和基を有する反応性基を2個以上有する化合物(D)を含み且つ上記エチレン性不飽和基に対するチオール基のモル当量が0.01〜1当量であって、化合物(A)、(B)、(C)、(D)の混合物を原料として、化合物(A)が有する加水分解性基の縮合、ならびに、化合物(A)、(B)および(D)が有するエチレン性不飽和基の重合、ならびに、化合物(C)が有するチオール基と化合物(A)、(B)および(D)が有するエチレン性不飽和基との付加反応により形成されたものである複合半透膜。
- 化合物(A)が次の一般式(a)に示される化合物である、請求項1または2に記載の複合半透膜。
Si(R1)m(R2)n(R3)4−m−n ・・・一般式(a)
(R1はエチレン性不飽和基を含む反応性基を示す。R2はアルコキシ基、アルケニルオキシ基、カルボキシ基、ケトオキシム基、アミノヒドロキシ基、ハロゲン原子またはイソシアネート基のいずれかを表す。R3は水素原子またはアルキル基を表す。m、nはm+n≦4を満たす整数であり、m≧1、n≧1を満たすものとする。R1、R2、R3それぞれにおいて2以上の官能基がケイ素原子に結合している場合、同一であっても異なっていてもよい。) - 化合物(C)がチオール基を3個以上有する請求項1、2または3に記載の複合半透膜。
- 微多孔性支持膜上に、エチレン性不飽和基を有する反応性基と加水分解性基とがケイ素原子に結合した化合物(A)、エチレン性不飽和基を有する反応性基と酸性基を有する化合物(B)、およびチオール基を有する反応性基を2個以上有する化合物(C)を含み且つ上記エチレン性不飽和基に対するチオール基のモル当量が0.01〜1当量であって、化合物(A)、(B)、(C)の混合物を塗布し、化合物(A)が有する加水分解性基の縮合、ならびに、化合物(A)および(B)が有するエチレン性不飽和基の重合、ならびに、化合物(C)が有するチオール基と化合物(A)および(B)が有するエチレン性不飽和基との付加反応により複合半透膜を形成することを特徴とする複合半透膜の製造方法。
- 微多孔性支持膜上に、エチレン性不飽和基を有する反応性基と加水分解性基とがケイ素原子に結合した化合物(A)、エチレン性不飽和基を有する反応性基と酸性基を有する化合物(B)、チオール基を有する反応性基を2個以上有する化合物(C)、およびエチレン性不飽和基を有する反応性基を2個以上有する化合物(D)を含み且つ上記エチレン性不飽和基に対するチオール基のモル当量が0.01〜1当量であって、化合物(A)、(B)、(C)、(D)の混合物を塗布し、化合物(A)が有する加水分解性基の縮合、ならびに、化合物(A)、(B)および(D)が有するエチレン性不飽和基の重合、ならびに、化合物(C)が有するチオール基と化合物(A)、(B)および(D)が有するエチレン性不飽和基との付加反応により複合半透膜を形成することを特徴とする複合半透膜の製造方法。
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