JP5464143B2 - 分枝状ポリアリールエーテルと、親水性ポリマーとから成るブレンド - Google Patents
分枝状ポリアリールエーテルと、親水性ポリマーとから成るブレンド Download PDFInfo
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- JP5464143B2 JP5464143B2 JP2010523480A JP2010523480A JP5464143B2 JP 5464143 B2 JP5464143 B2 JP 5464143B2 JP 2010523480 A JP2010523480 A JP 2010523480A JP 2010523480 A JP2010523480 A JP 2010523480A JP 5464143 B2 JP5464143 B2 JP 5464143B2
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- 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
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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- B01D67/0002—Organic membrane manufacture
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- B01D69/087—Details relating to the spinning process
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
- B01D71/44—Polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of groups B01D71/26-B01D71/42
- B01D71/441—Polyvinylpyrrolidone
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- 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
- B01D71/52—Polyethers
- B01D71/521—Aliphatic polyethers
- B01D71/5211—Polyethylene glycol or polyethyleneoxide
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- 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
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
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- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
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Description
成分(a)
(a1)一般式I
t、qは、相互に独立して0、1、2、又は3であり、
Q、T、Yは、相互に独立してその都度、−O−、−S−、−SO2−、S=O、C=O、−N=N−、−RaC=CRb、及び−CRcRd−から選択される化学結合又は基(この際、RaとRbは相互に独立してその都度、水素原子又はC1〜C12アルキル基を表し、かつRcとRdは相互に独立してその都度、水素原子又はC1〜C12アルキル基、C1〜C12アルコキシ基、若しくはC6〜C18アリール基を表し、この際、Q、T、及びYのうちの少なくとも1つが、−O−とは異なり、かつQ、T、及びYのうち少なくとも1つが−SO2−であり、かつ
Ar、Ar1は、相互に独立してC6〜C18アリーレン基である)]
の構成要素50〜99.9質量%と、
1つ又は1つより多い熱可塑性ポリマーセグメントから選択される、さらなる構成要素II 0〜40質量%、及び
(a2)ヒドロキシ官能価が少なくとも3である少なくとも1つの架橋剤V 0.1〜10質量%(この際、この少なくとも1つの架橋剤Vは、成分(a)中で反応された形で存在し、かつ(a1)及び(a2)から成る質量%の合計は100質量%である)
から構成される、少なくとも1つのポリアリールエーテルコポリマーを40〜95質量%、
並びに成分(b)
ポリビニルピロリドン、ポリビニルピロリドン−コポリマー、ポリエチレングリコール、ポリプロピレングリコール、エチレングリコールとプロピレングリコールとから成るコポリマー、水溶性セルロース誘導体、ポリアミド、ポリ酢酸ビニル、及びポリビニルアルコールから選択される少なくとも1つの親水性ポリマーを5〜60質量%、
(この際、成分(a)及び(b)から成る質量%の合計は、100質量%である)
含む、ポリマー混合物に関する。
本発明によれば、ポリマー混合物は、成分(a)として
(a1)一般式I
t、qは、相互に独立して0、1、2、又は3であり、
Q、T、Yは、相互に独立してその都度、−O−、−S−、−SO2−、S=O、C=O、−N=N−、−RaC=CRb、及び−CRcRd−から選択される化学結合又は基であり(この際、RaとRbは相互に独立してその都度、水素原子又はC1〜C12アルキル基を表し、かつRcとRdは相互に独立してその都度、水素原子又はC1〜C12アルキル基、C1〜C12アルコキシ基、若しくはC6〜C18アリール基を表し、ここでQ、T、及びYのうちの少なくとも1つが、−O−とは異なり、かつQ、T、及びYのうち少なくとも1つが−SO2−である)、かつ
Ar、Ar1は、相互に独立してC6〜C18アリーレン基である)]
の構成要素50〜99.9質量%と、
1つ又は1つより多い熱可塑性ポリマーセグメントから選択される、さらなる構成要素II 0〜40質量%、及び
(a2)ヒドロキシ官能価が少なくとも3である少なくとも1つの架橋剤V 0.1〜10質量%(この際、この少なくとも1つの架橋剤Vは、成分(a)中で反応された形で存在し、かつ(a1)及び(a2)から成る質量%の合計は100質量%である)
から構成される、少なくとも1つのポリアリールエーテルコポリマーを40〜95質量%
を含む。このためQ、T、及びYは相互に独立して化学結合であるか、又は上記の原子若しくは基のうちの1つであってよく、この際に化学結合とは、この場合に左側に隣接する基と、右側に隣接する基とが、化学結合を介して相互に直接結びついて存在していることである。本発明によれば、Q、T、及びYから成る群の少なくとも1つの要素は、−O−とは異なり、かつQ、T、及びYから成る群の少なくとも1つの要素は、−SO2−に相応する。好ましい実施態様においては、Q、T、及びYは、相互に独立して−O−、又は−SO2−である。
フロログルシン、4,6−ジメチル−2,4,6−トリ−(4−ヒドロキシフェニル)−ヘプテン−2(=三量体のイソプロペニルフェノール)、4,6−ジメチル−2,4,6−トリ−(4−ヒドロキシフェニル)−ヘプタン(=水素化された第一級イソプロペルフェノール)、1,3,5−トリ−(4−ヒドロキシフェニル)−ベンゾール、1,1,1−トリ−(4−ヒドロキシ−フェニル)−エタン及び1,1,1−トリ−(4−ヒドロキシ−フェニル)−プロパン、テトラ−(4−ヒドロキシフェニル)−メタン、1,4−ビス−[(4’,4’’−ジヒドロキシトリフェニル)−メチル]ベンゾール、及び2,2−ビス−[4,4’−ビス−(4−ヒドロキシフェニル)−シクロヘキシル]−プロパンである。
のハロゲン含有トリヒドロキシアリールエーテルである。このような化合物の例は:
1,3,5−トリス(4−ヒドロキシ−フェノキシ)−2,4,6−トリクロロベンゾール、
1,3,5−トリス−[4−(4−ヒドロキシ−フェニル−イソプロピル)−フェノキシ]−2,4,6−トリクロロベンゾール、
1,3,5−トリス−[4−(4−ヒドロキシ)−ビフェノキシ]−2,4,6−トリクロロベンゾール、
1,3,5−トリス−[4−(4−ヒドロキシ−フェニルスルホニル)−フェノキシ]−2,4,6−トリクロロベンゾール、及び
1,3,5−トリス−[4−(4−ヒドロキシ−フェニル−イソプロピル)−フェノキシ]−2,4,6−トリブロモベンゾールである。
本発明によれば成分(b)は、ポリビニルピロリドン、ポリビニルピロリドン−コポリマー、ポリエチレングリコール、ポリプロピレングリコール、エチレングリコールとプロピレングリコールとから成るコポリマー、水溶性セルロース誘導体、ポリアミド、ポリ酢酸ビニル、及びポリビニルアルコールから選択される親水性ポリマーを5〜60質量%含む。好適には成分(b)の親水性ポリマーは、水溶性であるか、又は水膨潤性である。
VP:VAcの質量比が20:80〜80:20、とりわけ30:70〜70:30、好適には40:60〜60:40で酢酸ビニルを有し、かつK価が10〜100、好適には20〜50である、N−ビニルピロリドン(VP)から成るコポリマー;
VPとVIとから成るコポリマー、とりわけVP:VIの質量比が40:60〜60:40のもの;とりわけ、質量比が40:60〜60:40であり、かつK値が10〜100、好適には20〜60である、VPとVCapとからなるコポリマー;
VP/QVIとの質量比が好ましくは20:80〜99:1である、VPと1−ビニル−3−メチルイミダゾリウムクロリド(好適には1−ビニルイミダゾールを塩化メチルにより四級化することにより得られるもの)から成るコポリマー(この際、VPと1−ビニル−3−メチルイミダゾリウムクロリドとから成るコポリマーが40,000〜1,000,000ドルトンより大きい分子量を有していてよい)、
から選択されるコポリマーである。
本発明はまた、溶液中にあるポリアリールエーテル−コポリマーを、同様に溶液中にある1つの、又はさらなる複数のコポリマーと混合することによる、本発明によるポリマーブレンドの製造に関する。このために、ポリアリールエーテルコポリマー、及び相応するポリマーを共通の媒体(この際にとりわけ、双極性の非プロトン性溶媒、例えばDMF、DMAC、NMP、DMSO、スルホラン、N−メチルカプロラクタム、尿素、又はこれらの混合物が適している)に溶かすことによって、混合する。溶媒の除去により、完全に混合されたポリマーブレンドが得られる。
本発明によるポリマー混合物を用いた膜の製造は、それ自体当業者に公知の工程又は方法を適用することにより、行うことができる。
(i)成分(a)及び(b)を含む本発明によるポリマー混合物の溶液を、溶媒(C)中で調製する工程、及び
(ii)ポリマー膜を形成させながら、溶媒(C)からポリマー混合物を分離する工程。
(ii−a)工程(i)から得られる溶液を、気体状雰囲気、とりわけ空気、選択的には芯液の存在下でノズルから押し出す工程、及び
(ii−b)工程(ii−a)で押し出された繊維を、それぞれ容器と凝固液(Koagulationsfluessigkeit)とを含む少なくとも1つの凝固浴に導入する工程。
ポリアリールエーテルの粘度数は、ISO1628に従って、25℃でN−メチルピロリドンの1%溶液中で測定した。
[式中、Cf若しくはCpは、出発溶液(フィード)中の、若しくは透過液中のポリエチレングリコール濃度である]。
成分(a−1)としては、分枝状のポリアリールエーテルを使用し、これは、N−メチルピロリドン(NMP)1000ml中の炭酸カリウム290.24gの作用下、ジクロロジフェニルスルホン576.16g、ジヒドロキシジフェニルスルホン485.33g、及び1,1,1−トリス−(4−ヒドロキシフェニル)エタン12.25gを芳香族求核重縮合することにより得られるものである。この混合物を3.5時間、195℃に維持した。120℃に冷却後、1時間にわたって塩化メチルを溶液に導入した。この後、NMP1000mlの添加によりバッチを希釈し、固体成分を濾過により分離し、そして質量比で1:9のNMP/水中での凝結によりこのポリマーを単離した。水で入念に洗浄した後、この生成物を真空中で120℃で12時間乾燥させた。生成物の粘度数は81.9ml/g、であり、ガラス転移温度は226℃であった。
中空糸膜を製造するための溶液を、以下のように調製した:まず、ポリアリールエーテルa−1若しくはa−V2を、成分(a)としてNMP中に溶解させた。引き続きPVPを成分(b)としてこの溶液に添加して、その組成を16/10/74質量%(a−1/b−1/NMP)にした。この溶液を引き続き48時間、室温で撹拌した。紡糸の前にこれらの溶液を、1日間脱気した。
Claims (20)
- 成分(a)及び(b)を含むポリマー混合物であって、
前記成分(a)
(a1)一般式I
t、qは、相互に独立して0、1、2、又は3であり、
Q、T、Yは、相互に独立してその都度、−O−、−S−、−SO2−、S=O、C=O、−N=N−、−RaC=CRb−、及び−CRcRd−から選択される化学結合又は基であり(この際、RaとRbは相互に独立してその都度、水素原子又はC1〜C12アルキル基を表し、かつRcとRdは相互に独立してその都度、水素原子又はC1〜C12アルキル基、C1〜C12アルコキシ基、若しくはC6〜C18アリール基を表し、この際、Q、T、及びYのうちの少なくとも1つが、−O−とは異なり、かつQ、T、及びYのうち少なくとも1つが−SO2−である)、かつ
Ar、Ar1は、相互に独立してC6〜C18アリーレン基である)]
の構成要素90〜99.9質量%、
及び
(a2)ヒドロキシ官能価が少なくとも3である少なくとも1つの架橋剤V 0.1〜10質量%
(この際、この少なくとも1つの架橋剤Vは、成分(a)中で反応された形で存在し、かつ(a1)及び(a2)から成る質量%の合計は100質量%である)
から構成される、少なくとも1つのポリアリールエーテルコポリマーを40〜95質量%、
並びに前記成分(b)
ポリビニルピロリドン、ポリビニルピロリドン−コポリマー、ポリエチレングリコール、ポリプロピレングリコール、エチレングリコールとプロピレングリコールとから成るコポリマー、水溶性セルロース誘導体、ポリアミド、ポリ酢酸ビニル、及びポリビニルアルコールから選択される少なくとも1つの親水性ポリマーを5〜60質量%、
(この際、成分(a)及び(b)から成る質量%の合計は、100質量%である)
含む、ポリマー混合物。 - 前記ポリマー混合物が成分(b)として、ポリビニルピロリドン及びポリビニルピロリドン−コポリマーの少なくとも1つを10〜60質量%含む、請求項1に記載のポリマー混合物。
- 成分(b)の質量平均分子量が、100,000g/mol〜1,000,000g/molである、請求項1から3までのいずれか1項に記載のポリマー混合物。
- 架橋剤Vとして、少なくとも3つのフェノール性ヒドロキシ基を有する少なくとも1つの有機化合物が反応された形で含まれている、請求項1から4までのいずれか1項に記載のポリマー混合物。
- 架橋剤Vとして、1,1,1−トリス−(4−ヒドロキシフェニル)エタンが反応された形で含まれている、請求項1から5までのいずれか1項に記載のポリマー混合物。
- 成分(a)中のQ、T、及びYが、相互に独立して−O−、又はSO2である、請求項1から6までのいずれか1項に記載のポリマー混合物。
- 成分(a)中のArが、1,4−フェニレン、1,3−フェニレン、ナフチレン、及び4,4’−ビスフェニレンから成る群から選択されている、請求項1から7までのいずれか1項に記載のポリマー混合物。
- 成分(a)中のAr1が、フェニレン、又はナフチレンである、請求項1から8までのいずれか1項に記載のポリマー混合物。
- 請求項1から9までのいずれか1項に記載のポリマー混合物を含む、ポリマー膜。
- 前記ポリマー膜が中空糸膜である、請求項10に記載のポリマー膜。
- (i)請求項1から9までのいずれか1項に記載のポリマー混合物の溶液を、溶媒(C)中で調製する工程、及び
(ii)ポリマー膜を形成させながら、溶媒(C)からポリマー膜を分離する工程
を含む、ポリマー膜の製造方法。 - 前記ポリマー膜が中空糸膜である、請求項12に記載のポリマー膜の製造方法。
- 工程(ii)における前記ポリマー混合物の分離、及び溶媒(C)の分離を、工程(i)で得られる溶液の紡糸により行う、請求項12又は13に記載のポリマー膜の製造方法。
- 工程(ii)において、工程(i)で得られる溶液の紡糸を、ドライジェット湿式紡糸法により行う、請求項14に記載のポリマー膜の製造方法。
- 工程(ii)で使用される溶液が、溶媒(C)を含む溶液の全質量に対してポリマー混合物を5〜40質量%含む、請求項15に記載のポリマー膜の製造方法。
- 請求項13に記載の方法によって得られる中空糸膜。
- ポリマー膜を製造するための、請求項1から9までのいずれか1項に記載のポリマー混合物の使用。
- 透析フィルターを製造するための、請求項1から9までのいずれか1項に記載のポリマー混合物の使用。
- 請求項17に記載の中空糸膜を含む、透析フィルター。
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