JP5882236B2 - 膜のための1つ以上のポリシロキサンブロックを含むポリウレタンブロックコポリマー - Google Patents
膜のための1つ以上のポリシロキサンブロックを含むポリウレタンブロックコポリマー Download PDFInfo
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- JP5882236B2 JP5882236B2 JP2012556439A JP2012556439A JP5882236B2 JP 5882236 B2 JP5882236 B2 JP 5882236B2 JP 2012556439 A JP2012556439 A JP 2012556439A JP 2012556439 A JP2012556439 A JP 2012556439A JP 5882236 B2 JP5882236 B2 JP 5882236B2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
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- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
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Classifications
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
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- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/54—Polyureas; Polyurethanes
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01D71/68—Polysulfones; Polyethersulfones
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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
- B01D71/70—Polymers having silicon in the main chain, with or without sulfur, nitrogen, oxygen or carbon only
- B01D71/701—Polydimethylsiloxane
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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
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/80—Block polymers
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4081—Mixtures of compounds of group C08G18/64 with other macromolecular compounds
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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Description
mは、1〜50の範囲であり、
(X)は、式
(Y)は、式
(A)は、脂肪族又は芳香族ジイソシアネート結合の残基であり、
(B)は、アルカノール末端基を含み、及び場合によりさらに1つ以上の脂肪族エーテル部を含む、直鎖のオリゴシロキサン又はポリシロキサンの残基であり、かつ
(C)は、芳香族オリゴスルホン又はポリスルホンブロックである]の成分(A)、(B)及び(C)を含むオリゴウレタン及びポリウレタン分子に関する。
Arは、−Ph−Ph−及び−Ph−Sp−Ph−から選択され;
Phは、フェニル又はC1〜C4アルキルによって置換されたフェニルであり;
スペーサーSpは、独立して、−O−又はC1〜C3アルキレンである。
(A)及び(B)であるが(C)ではない前記成分、又は式−(X)n−
[式中、nは、2〜100、特に2〜50の範囲であり、
(X)は、式
(B)は、特に3以上のSi原子を含み、かつアルカノール末端基を含み、かつ場合によりさらに1つ以上の脂肪族エーテル部を含む直鎖のオリゴシロキサン又はポリシロキサンの残基である]のブロックである]の、あらゆる他のスルホン部を含むオリゴウレタン及びポリウレタンを含む水濾過膜に関する。
(A)は、有利には、C2〜C12アルキレン及びArから選択される二価の残基であり、
(B)は、有利には、式
Arは、−Ph−Sp−Ph−であり、
Phは、フェニル又はC1〜C4アルキルによって置換されたフェニルであり、かつ
Spは、独立して、直接結合、−O−、C1〜C3アルキレンから選択される]のオリゴシロキサン又はポリシロキサンの二価の残基である。
1H−NMR分光法:(SiMe2O)/(C2H4O):0.71
元素分析[%]:C:44.7;H:8.7;Si:15.7
によって特徴付けられる、リンカーとしてIM22及びHDIを含むポリウレタン、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエチレンオキシド)ウレタン。
1H−NMR分光法:(SiMe2O)/(C2H4O):0.27〜1.07
元素分析[%]:C:40.06〜47.2;H:8.1〜8.5;Si:10.5〜22.0
によって特徴付けられる、リンカーとして、IM15−PEG2000(1:1)及びHDIを含むポリウレタン、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエーテル)ウレタン。
1H−NMR分光法:(SiMe2O)/(CMe2):0.58
元素分析[%]:C:56.8;H:6.3;Si:10.0
によって特徴付けられる、リンカーとして、PSU1−IM15(2:1)及びHDIを含むポリウレタン、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエーテルスルホニル)ウレタン。
1H−NMR分光法:(SiMe2O)/(CMe2):1.45
元素分析[%]:C:62.6;H:6.2;Si:10.6
によって特徴付けられる、リンカーとして、PSU1−IM22(2:1)及びHDIを含む、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエチレンオキシド−ブロック−コ−ポリエーテルスルホニル)ウレタン。
1H−NMR分光法:(SiMe2O)/(C2H4O):0.91
元素分析[%]:C:40.2;H:8.5;Si:24.6
によって特徴付けられる、リンカーとして、IM15−IM22(1:1)及びHDIを含む、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエチレンオキシド−ブロック−ポリジメチルシロキサン)ウレタン。
によって特徴付けられる、リンカーとして、IM11−IM22(2:1)を含む、ポリ(ポリジメチルシロキサン−ブロック−コ−ポリエチレンオキシド−ブロック−ポリジメチルシロキサン)ウレタン。
本発明のコポリマーは、有利には、ポリマー組成物、例えば膜、特に水処理又はゲル分離膜のための組成物において、耐付着添加剤としてとして使用される。
1. 適した溶液、例えばNMP、DMA、DMSO又はそれらの混合物中での膜のドープのためのマトリックスポリマーを溶解する工程。
2. 孔形成添加剤、例えばPVP、PEG、スルホン化PES又はそれらの混合物を添加する工程。
3. 種々の溶液が得られるまで混合物を加熱する工程。典型的に、5〜250℃、好ましくは25〜150℃、最も好ましくは60〜90℃での温度。
4. 5〜250℃、好ましくは25〜150℃、最も好ましくは60〜90℃での温度で、耐付着ケイ素−ポリウレタン添加剤をドープに添加する工程。場合により、他の添加剤、例えば銀含有化合物を同様の工程において添加してよい。
5. 混合物が1〜15時間以内で形成されるまで、典型的に均一化が2時間以内で終了するまで、溶液/懸濁液を撹拌する工程。
6. 凝固浴槽中で膜ドープをキャスティングして、膜構造を得る工程。場合により、キャスティングを、ポリマー支持体(織物でない)を、膜構造を機械的に安定するために使用して得られてよい。適用のための生物活性を試験するために、平坦な膜製造における標準の手法を使用する。
7. 活性剤含有率に関して膜を分析する工程。
L リットル
NMP N−メチルピロリドン
PD 多分散性
PEG ポリエチレングリコール
PES ポリエーテルスルホン
PVP ポリビニルピロリドン
thf テトラヒドロフラン
w%、wt% 質量パーセント。
A)ジイソシアネート
HDI:1,6−ヘキサメチレンジイソシアネート(Bayer社(ドイツ)から市販されているDesmodur H(登録商標))
TDI:2,4−トルエンジイソシアネート(Aldrich社(ドイツ)から市販されている)
MDI:ジフェニルメタン−4,4’−ジイソシアネート(Bayer社(ドイツ)から市販されているDesmodur44MC(登録商標))
テトラヒドロフラン:Aldrich社(ドイツ)から市販されている。
N−メチルピロリドン(NMP):Aldrich社(ドイツ)から市販されている。
ポリビニルピロリドン(PVP):BASF社(ドイツ)から市販されているLuvitec(登録商標)PVP40K。
装置:250mlエルレンマイヤーガラス管、磁気攪拌機、熱板、コンデンサー、内部温度計
ジオール成分を、テトラヒドロフラン(thf)120ml中で25℃で撹拌する。ジオール成分のOH数の合計に従って、ジイソシアネート成分を一投与量で添加する。固体のジイソシアネート成分を、溶液として、thf30ml中で添加する。5分間混合物を撹拌した後、触媒(1,8−ジアザビシクロ[5.4.0]−ウンデカ−7−エン(DBU):0.1g及びジブチルスズジラウレート:0.1g)を添加する。2325cm−1で良好な観察可能なNCO吸収変数を、反応の経過を監視するために使用する。その反応混合物を15時間25℃で撹拌し、続いて、全ての揮発成分を、回転蒸発器及び高真空ポンプを使用して蒸発する。粗ポリマー化合物は、元素分析、1H−NMR及びゲル浸透クロマトグラフィーによって特徴付けられる。次の表1は、使用した反応物の量、及び得られたポリマーの特徴を示す。
テトラヒドロフラン及び比較としてポリスチレン中でのゲル浸透クロマトグラフィー(GPC);溶剤としてd6−ジメチルスルホキシド中での元素分析(EA)及び1H−NMR分光法。結果を表2において示す。
遅疑の手法を、膜の製造において実施する。
膜を、XPS(X線光電子分光法)によって特徴化する。表面の2〜10nmの深さでケイ素原子の得られた濃度は、ポリエーテルスルホンを装填する5質量%の最初の添加剤で、バルク材料中での理論的ケイ素に基づく、高い富化を示す(富化係数EF=表面での質量%(Si)/計算値の質量%(Si))。
水分流動を、圧力源として窒素シリンダーを備えた供給槽に連結した全量濾過セル(110ml容量、膜面積1.59×10-3m2)中で実施する。濾過セルは、膜状に置かれた多孔質支持体で満たされたシリンダー容器からなる。撹拌を、セル中で開始し、400rpmの速度を、試験中維持する。実験を、一定の圧力(100kPa)で操作し、そして透過水を、電子天秤上に置かれたビーカーに採取する。圧力変換器を、膜の上流側に連結して、セル中の圧力を測定する。天秤及び圧力変換器の双方を、データを記録するためにコンピュータに連結する。膜を、流量測定する前にエタノールで湿らせる。膜M6〜M11及びM12(比較)に関する結果は、5測定[WAC]又は3測定[水分流動]から得られる平均値である。本発明の膜は、68°よりも高い水接触角及び良好な水分流動を示す。
2つの試験を、膜の表面の耐付着特性を評価するために適用する。
a)タンパク質付着;本発明の膜の流量の回収を、添加剤を有さない膜に関して測定する:表面を、標準タンパク質としてBSA(ウシ血清アルブミン)と接触させる。BSA付着は、水分流動で低減する;流量を、水で洗浄すること(Jw)によって、又は水酸化ナトリウムでのさらなる化学処理(Jc)によって、回収させる。流量回収(最初の水分流動に対する標準化)は、自己洗浄及び汚損の低減に対する膜の性能を示す。
水分流動及びBSA濾過を、高さ3mm、幅25mm及び長さ110mmのチャネル寸法の市販されていない実験用原型Perspex十字流モジュールを使用して実施する。100kPaの供給圧力を、蠕動供給ポンプ(Cole Parmer社製のMaster flux Model 7529−00)を使用して得て、そしてモジュールの出口に位置しているボール弁によって調整する。与えられたチャネル寸法で、0.2m/sの十字流速度を、全ての実験で維持する。膜の供給及び透過水側の双方に連結した圧力変換器(Labom Diff. Pressure transmitter CP1310)を使用して、TMP(膜を横切る膜圧)を測定する。バランスを、透過水流を監視するために使用する。
シロキサンブロック−ウレタンコポリマーを実施例1に従って製造する。種々のジオール及び使用したイソシアネートのタイプの割合を、以下の表において繰り返す:
Claims (17)
- ポリマー組成物であって、以下、
a)式I
mは1〜100の範囲であり、
(X)は、式
(Y)は、式
(A)は、脂肪族又は芳香族ジイソシアネートリンカーの残基であり、
(B)は、アルカノール末端基を含み、及び場合によりさらに1つ以上の脂肪族エーテル部を含む、直鎖のオリゴシロキサン又はポリシロキサンの残基であり、かつ
(C)は、芳香族オリゴスルホン又はポリスルホンブロックである]のオリゴウレタンもしくはポリウレタン、又はかかるオリゴウレタンもしくはポリウレタンの混合物、並びに
b)ポリビニルピロリドン、ポリ酢酸ビニル、酢酸セルロース、ポリアクリロニトリル、ポリアミド、ポリオレフィン、ポリエステル、ポリスルホン、ポリエーテルスルホン、ポリカーボネート、ポリエーテルケトン、スルホン化ポリエーテルケトン、ポリアミドスルホン、ポリフッ化ビニリデン、ポリ塩化ビニル、ポリスチレン及びポリテトラフルオロエチレン、それらのコポリマー、並びにそれらの混合物からなる群から選択される1つ以上の他の有機ポリマー
を含む、ポリマー組成物。 - 式Iの化合物の分子量(Mn)が、1500〜100000の範囲であり、その際n及びmは、それぞれ、1〜50の範囲であり、かつkは1〜20の範囲である、請求項1に記載のポリマー組成物。
- 式Iのオリゴウレタン又はポリウレタンにおいて、
(A)が、C2〜C12アルキレン及びArから選択される二価の残基であり、
(B)が、式
(C)が、ジフェニルスルホンモノマー、又は1〜50個のフェニル−SO2−フェニル部、及び場合によりさらに1〜50個のAr部を含む直鎖のオリゴマーもしくはポリマーブロックであり、その際前記フェニル−SO2−フェニル部およびAr部は、オリゴマー又はポリマーの場合に、スペーサーSpによって共に結合され;
Arは、−Ph−Sp−Ph−であり;
Phは、フェニル又はC1〜C4アルキルによって置換されたフェニルであり;かつ
Spは、独立して、直接結合、−O−、C1〜C3アルキレンから選択される、請求項1又は2に記載のポリマー組成物。 - 式Iのオリゴウレタン又はポリウレタンを、合計ポリマー組成物の0.1〜25質量%の量で、均一相中で、又は表面で富化して、含む、請求項1から3までのいずれか1項に記載のポリマー組成物。
- 1つ以上の抗微生物剤又は静細菌剤をさらに含む、請求項1から4までのいずれか1項に記載のポリマー組成物。
- 請求項1から5までのいずれか1項に記載のポリマー組成物を含む、膜。
- 膜の平均ケイ素含有率を超えた、膜表面から2〜10nmの区間において、ケイ素の少なくとも8倍富化を示す、請求項6に記載の膜。
- 水処理又はガス分離目的のための半透性膜の製造のための方法であって、請求項1から5までのいずれか1項に記載のポリマー組成物を膜材料中に組み込むことを含む、方法。
- 抗微生物膜の製造のための、水分離又はガス分離目的のための、請求項1から5までのいずれか1項に記載のポリマー組成物の使用。
- 式Iの化合物の分子量(Mn)が、1500〜100000の範囲であり、その際n及びmは、1〜50の範囲であり、かつkは1〜20の範囲である、請求項10に記載の化合物。
- ポリマー組成物に耐生物付着又は静細菌特性を付与する添加剤としての、請求項1から5まで、又は10から11までのいずれか1項に記載の式Iのオリゴウレタン又はポリウレタンの使用。
- ポリビニルピロリドン、ポリ酢酸ビニル、酢酸セルロース、ポリアクリロニトリル、ポリアミド、ポリオレフィン、ポリエステル、ポリスルホン、ポリエーテルスルホン、ポリカーボネート、ポリエーテルケトン、スルホン化ポリエーテルケトン、ポリアミドスルホン、ポリフッ化ビニリデン、ポリ塩化ビニル、ポリスチレン及びポリテトラフルオロエチレン、それらのコポリマー、並びにそれらの混合物からなる群から選択される1つ以上の有機ポリマーをさらに含有する、請求項13に記載の水濾過膜。
- 水濾過膜に、耐生物付着又は静細菌特性を付与する添加剤としての、請求項13から15までのいずれか1項に記載の式−(X)n−のオリゴウレタン又はポリウレタンの使用。
- a)
b)式
c)式
d)式
e)式
から選択される化合物。
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AU2011226240B2 (en) | 2016-09-15 |
KR20130039723A (ko) | 2013-04-22 |
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