CN104069748B - 源自于包含酸酐和磺酰卤官能团的芳族单体的复合聚酰胺膜 - Google Patents
源自于包含酸酐和磺酰卤官能团的芳族单体的复合聚酰胺膜 Download PDFInfo
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- CN104069748B CN104069748B CN201410112607.9A CN201410112607A CN104069748B CN 104069748 B CN104069748 B CN 104069748B CN 201410112607 A CN201410112607 A CN 201410112607A CN 104069748 B CN104069748 B CN 104069748B
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- monomer
- aromatic anhydride
- carboxylic acid
- thin film
- acid halides
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- 239000000178 monomer Substances 0.000 title claims abstract description 65
- 239000004952 Polyamide Substances 0.000 title claims abstract description 32
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- 239000002131 composite material Substances 0.000 title claims abstract description 19
- 150000008064 anhydrides Chemical class 0.000 title claims description 6
- 125000002128 sulfonyl halide group Chemical group 0.000 title abstract description 4
- 125000003118 aryl group Chemical group 0.000 title description 8
- -1 aromatic anhydride Chemical class 0.000 claims abstract description 68
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 15
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- 238000012695 Interfacial polymerization Methods 0.000 claims abstract description 10
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- 239000011574 phosphorus Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
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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
- B01D71/56—Polyamides, e.g. polyester-amides
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- 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
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/34—Applying different liquids or other fluent materials simultaneously
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
- B05D3/107—Post-treatment of applied coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
Abstract
复合聚酰胺膜的制造方法，所述方法包括向多孔载体的表面施加多官能胺单体和多官能酰卤单体并且界面聚合所述单体以形成薄膜聚酰胺层的步骤，并且其中所述方法特征在于：i）在包含至少一个磺酰卤官能团的芳族酸酐单体存在下进行界面聚合，或ii）向所述薄膜聚酰胺层施加所述芳族酸酐单体。
Description
技术领域
本发明涉及复合聚酰胺膜。
背景技术
薄膜复合（TFC）膜用于各种流体分离。所述薄膜层可以通过将多官能胺（例如间苯二胺）和多官能酰卤（例如均苯三甲酰氯）单体用不混溶溶液顺序涂布在载体上而在二者之间发生界面缩聚反应而形成，参见US4277344。为了改善膜性能，可以向涂层溶液之一或二者中添加各种成分。例如，US4606943和US6406626描述了利用多官能胺和多官能酰卤与多官能酸酐卤化物（偏苯三酸酐酰氯）一起形成薄膜聚酰胺。类似地，WO2012/102942和WO2012/102943描述了添加包含羧酸官能团的芳族酸酐单体；WO2013/032586描述了添加包含膦酸部分的芳族酸酐单体。US6878278描述了向酰卤涂层溶液添加范围广泛的络合剂，包括各种含磷物质。US2011/0049055描述了添加来源于磺酰（sulfonyl）、亚磺酰、烃硫基(sulfenyl)、硫酰（sulfuryl）、磷酰、膦酰、氧膦基（phosphinyl）、硫代磷酰、硫代膦酰和碳酰卤化物的部分。US6024873描述了添加选定的醇、醚、酮、酯、卤代烃、含氮化合物和含硫化合物。
US6783711和US8092918描述了通过多官能胺单体与芳族磺酰卤单体界面聚合形成的复合聚合物磺酰胺膜的制备。也参见Hurndall等，“Poly(2-vinylimidazolin)Composite Reverse Osmosis Membranes,"Desalination,90（1993）41-54页。
一直在寻找进一步改善膜性能的新添加剂。
发明内容
本发明包括制造复合聚酰胺膜的方法，所述方法包括以下步骤：向多孔载体表面施加多官能胺和酰卤单体，和界面聚合所述单体以形成薄膜聚酰胺层。所述方法还包括以下步骤中的至少一个：i）在包含至少一个磺酰卤官能团的芳族酸酐单体存在下进行界面聚合；和/或ii)向所述薄膜聚酰胺层施加所述芳族酸酐单体。本发明包括许多其他实施方式。
具体实施方式
本发明不具体限于特定类型、构造或形状的复合膜或应用。例如，本发明适用于可在各种应用包括正向渗透（FO）、逆渗透（RO）、纳滤（NF）、超滤（UF）和微滤（MF）流体分离中使用的平板、管状和中空纤维聚酰胺膜。然而，本发明对设计用于RO和NF分离的膜特别有用。RO复合膜对几乎所有的溶解盐是相对不可渗透的，并通常阻隔超过约95%的单价离子盐，例如氯化钠。RO复合膜还通常阻隔超过约95%的无机分子以及分子量大于约100道尔顿的有机分子。NF复合膜比RO复合膜更可渗透，并通常阻隔小于约95%的单价离子盐，同时取决于二价离子的种类，阻隔超过约50%（并经常超过90%）的二价离子盐。NF复合膜还通常阻隔纳米范围的粒子以及分子量大于约200至500道尔顿的有机分子。
复合聚酰胺膜的实例包括FilmTec Corporation FT-30TM型膜，即平板复合膜，其包括无纺背衬网（例如PET网格布）的底层（背面）、通常厚度约25-125μm的多孔载体中间层、和包含厚度通常小于约1微米例如从0.01微米至1微米但更通常从大约0.01至0.1μm的薄膜聚酰胺层的顶层(正面)。所述多孔载体通常是聚合材料，其孔径大小足以允许渗透物基本不受限制地通过，然而并非大得足以妨碍其上形成的薄膜聚酰胺层的桥接。例如，所述载体的孔径优选从约0.001至0.5μm。多孔载体的非限制性实例包括由下列材料制成的多孔载体：聚砜，聚醚砜，聚酰亚胺，聚酰胺，聚醚酰亚胺，聚丙烯腈，聚(甲基丙烯酸甲酯)，聚 乙烯，聚丙烯，和各种卤代聚合物例如聚偏氟乙烯。对于RO和NF应用而言，所述多孔载体提供了强度，但由于它比较高的孔隙率，提供的抗流体流动性很小。
由于它比较薄，所述聚酰胺层根据它在多孔载体上的涂层覆盖量或负载量经常被描述为例如约2至5000mg聚酰胺/平方米多孔载体表面积，并更优选约50至500mg/m2。如US4277344和US6878278所述，优选通过多官能胺单体和多官能酰卤单体之间在多孔载体表面上的界面缩聚反应，来制备聚酰胺层。更具体地，可以通过多官能胺单体与多官能酰卤单体(其中每个术语意图是指利用单种物质或多种物质两者)在多孔载体的至少一个表面上进行界面聚合，来制备所述聚酰胺膜层。在本文中使用时，术语“聚酰胺”是指沿着分子链存在酰胺键（—C(O)NH—）的聚合物。所述多官能胺和多官能酰卤单体最通常通过溶液涂布步骤的方式施加于多孔载体，其中所述多官能胺单体通常从水基或极性溶液涂布，而多官能酰卤从有机基或非极性溶液涂布。虽然涂布步骤不需要按照特定的顺序，但优选多官能胺单体首先被涂布在多孔载体上，然后是多官能酰卤。可以通过喷涂、薄膜涂布、辊涂或通过使用浸渍槽以及其他涂布技术完成涂布。多余的溶液可以通过气刀、干燥器、烘箱等等从所述载体上除去。
所述多官能胺单体包含至少两个伯或仲氨基，并且可以是芳族的（例如间苯二胺、对苯二胺、1,3,5-三氨基苯、1,3,4-三氨基苯、3,5-二氨基苯甲酸、2,4-二氨基甲苯、2,4-二氨基茴香醚、和苯二甲胺）或脂族的（例如乙二胺、丙二胺和三(2-二氨基乙基)胺）。优选的多官能胺单体的实例包括具有两个或三个氨基的伯胺，例如间苯二胺，和具有两个氨基的脂族仲胺，例如哌嗪。一种优选的多官能胺是间苯二胺（mPD）。多官能胺单体可以以极性溶液施加于多孔载体。所述极性溶液可以含有约0.1至约20重量%并更优选约0.5至约6重量%的多官能胺单体。一旦涂布在多孔载体上，可以任选除去多余的溶液。
所述多官能酰卤单体包含至少两个酰卤基团并优选从有机基或非极性溶剂涂布，但是所述多官能酰卤可以从气相递送（例如，对于具有 足够的蒸气压的多官能酰卤）。所述多官能酰卤没有特别的限制，可以使用芳族或脂环族的多官能酰卤及其组合。芳族多官能酰卤的非限制性实例包括：均苯三甲酰氯、对苯二甲酰氯、间苯二甲酰氯、联苯二羧酰氯和萘二羧酰氯。脂环族多官能酰卤的非限制性实例包括：环丙烷三羧酰氯，环丁烷四羧酰氯，环戊烷三羧酰氯，环戊烷四羧酰氯，环己烷三羧酰氯，四氢呋喃四羧酰氯，环戊烷二羧酰氯，环丁烷二羧酰氯，环己烷二羧酰氯，和四氢呋喃二羧酰氯。一种优选的多官能酰卤是均苯三甲酰氯（TMC）。多官能酰卤在非极性溶剂中溶解的范围可以为约0.01至10重量%、优选0.05至3重量%，并可以作为连续涂层操作的一部分进行递送。适合的溶剂是能够溶解多官能酰卤并与水不混溶的溶剂，例如己烷、环己烷、庚烷和卤代烃，例如FREON系列。优选的溶剂包括对臭氧层很少形成威胁并在经历常规加工时在闪点和可燃性方面足够安全从而不需要采取特殊防范的溶剂。优选的溶剂是可得自Exxon Chemical Company的ISOPARTM。
涂层溶液之一或二者，但是更优选所述非极性溶液可以包含附加的材料包括助溶剂、相转移剂、增溶剂和络合剂，其中单种添加剂可以起到多种功能。代表性的助溶剂包括：苯，甲苯，二甲苯，均三甲苯，乙苯–二乙二醇二甲醚，环己酮，乙酸乙酯，丁基卡必醇TM乙酸酯，月桂酸甲酯和丙酮。US6878278描述了添加范围广泛的代表性络合剂，所述络合剂可以在进行界面聚合之前与所述非极性溶液组合。一类这样的络合剂由式（I）表示。
式(I):
α(Lxβ)y
其中α是不含硫的结合芯（binding core），选自落入如下范围之内的元素：(a)IIIA-VIB族（即，IIIA、IVA、VA、VIA、VIIA、VIIIA、IB、IIB、IIIB、IVB、VB、VIB族）和(b)常规IUPAC周期表的3-6周期（即，以Na、K、Rb和Cs开始的周期）。常规IUPAC形式周期表的IIIA至VIB族对应于：“新符号”IUPAC周期表的3-16族和CAS版本周期表的IIIB-VIA族。为了避免任何混淆，在此的进一步参考将利用常 规IUPAC周期表，即IIIA族对应于以Sc、Y、La等开始的列，VIB族对应于以O、S、Se、Te、Po开始的列。具体的实例包括：(1)下列金属：铝，钪，钛，钒，铬，锰，铁，钴，镍，铜，锌，镓，锗，砷，钇，锆，铌，钼，锝，钌，铑，钯，银，镉，铟，锡，锑，碲，镧，铈，镨，钕，钷，钐，铕，钆，铽，镝，钬，铒，铥，镱，镥，铪，钽，钨，铼，锇，铱，铂，金，汞，铊，铅，铋（铋通常不优选）和钋；(2)下列半导体：硅，硒和锗；以及(3)磷。特别优选的结合芯包括：Al、Si、P、As、Sb、Se和Te，以及金属例如：Fe、Cr、Co、Ni、Cu和Zn。L是任选的相同或不同的化学连接基团，选自例如下面的连接基团：含碳部分，例如芳基、烷烃、烯烃、--O--、--S--、--N--、--H--、--P--、--O--P--、和--O--P--O--（各自可以是取代或未取代的）。β是相同或不同的增溶基团，并包含1至12个碳原子，它可以是取代或未取代的并且可以包含如L定义的内部连接基团。实例包括具有1至6个碳原子的脂族和芳烃基团、芳基、杂环基和烷基。"x"是0至1的整数，“y”是1至5、优选2至4的整数。虽然取决于所使用的具体溶剂和酰卤，但是下面的络合剂通常可用于本发明：磷（例如膦、磷酸酯）、铋、砷和锑的三苯基衍生物；磷的烷氧酯，包括亚磷酸三丁酯和二丁酯；有机金属络合物，例如二茂铁和四乙铅以及铁(II)、铁(III)、钴(III)和Cr(III)的乙酰丙酮络合物。这样的络合剂的优选类别由式(II)表示。
式(II):
其中“P”是磷，“O”是氧，R1、R2和R3独立地选自含碳部分。术语“含碳部分”用来指有支链和无支链的无环基团和环状基团，所述无环基团例如甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、2-戊基、3-戊基、叔丁基等，它们可以是未取代的或取代的（例如用酰胺基、醚基、酯基、砜基、羰基、酸酐、氰化物、腈、异氰酸酯、氨基甲酸酯、β-羟基酯、双和三键等取代）；所述环状基团例如环戊基、环己基、芳烃例如苯基、杂环（例如吡啶）等，它们可以是未取代的或取代的（例 如用甲基、乙基、丙基、羟基、酰胺、醚、砜、羰基、酯等取代)。环部分可以通过脂族连接基团例如甲基、乙基等与磷原子连接。优选的含碳部分包括未取代的、有支链或无支链的C1-C12基团，并且更优选C1-C8脂族基团，例如：甲基，乙基，丙基，异丙基，丁基，2-甲基丁基，3-甲基丁基，2-乙基丁基，戊基，己基等等。另外，所述部分包括苯基。当使用时，前述的络合剂优选添加到包含所述多官能酰卤的有机基或非极性涂层溶液中，所述络合剂与多官能酰卤单体的比率为约1:5至5:1，优选1:1至3:1。在另一种优选实施方式中，涂层溶液内络合剂的浓度是约0.001至2重量%。
一旦彼此发生接触，所述多官能酰卤和多官能胺单体在它们的表面界面处反应，形成聚酰胺层或膜。这种层，经常被称为聚酰胺“识别层”或“薄膜层”，提供了主要功能是从溶剂（例如水性进料）中分离溶质（例如盐）的复合膜。
多官能酰卤与多官能胺单体的反应时间可以小于一秒，但是接触时间通常在约1至60秒，之后可以任选地通过气刀、水浴、干燥器等等除去多余的液体。除去多余的溶剂可以通过在升高的温度下、例如约40℃至约120℃下干燥来完成，但是也可以利用在环境温度下风干。
在一种实施方式中，所述方法包括向所述薄膜聚酰胺层（一旦形成）施加芳族酸酐单体的步骤。当在聚酰胺形成之后施加时，所述主题单体被认为与薄膜聚酰胺中存在的残留胺基团反应。在可替代实施方式中，在所述多官能酰卤和胺单体的界面聚合期间存在所述主题芳族酸酐单体。当在界面聚合期间存在时，所述主题单体被认为被引入所生成的聚酰胺结构内（即主题单体和多官能胺和酰卤单体形成反应产物）。
所述主题芳族酸酐单体包含优选含18个或更少碳原子的芳族部分，例如苯、萘、蒽、菲、苯并菲、芘、蒽醌、联苯等等。其他代表性的芳环结构包括杂芳烃例如吡啶、吡嗪、呋喃和噻二唑。优选苯环结构。所述主题芳族酸酐单体还包含酸酐和至少一个磺酰氯官能团。所述芳族部分可以任选用非胺反应性官能团（例如在薄膜聚酰胺层形成期间存在的时间段和条件期间“无反应性”）取代，所述官能团例如：卤素，酮， 腈，硝基，砜，磺酰胺，酯包括磷酯，以及具有1至12个碳原子并且可以是未取代的或用例如卤素、酮、腈和醚基团的部分取代的烷基和烯基基团。优选的单体类别由式(III)表示。
式（III）:
其中所述磺酰卤基团可以位于芳环上的任何开放位置（例如2、3、4和5位），并且X是卤素。正如所提到的，所述单体可以包含多个磺酰卤基团（例如1至4个，优选1或2个）。优选的卤素包括氯和溴。优选的物质是1,3-二氧代-1,3-二氢异苯并呋喃-5-磺酰氯。
如之前所述，向多孔载体的表面施加多官能单体的步骤优选包括施加包含所述多官能胺单体的极性溶液和包含所述多官能酰卤单体的非极性溶液。施加溶液的步骤优选包括通过喷涂、膜式涂布、辊涂、或通过使用浸渍槽进行涂布。在一种实施方式中，所述主题芳族酸酐单体在施加步骤之前，例如在多孔载体上涂布非极性溶液之前，添加到所述非极性溶液中。在这样的实施方式中，所述非极性溶液优选包含至少0.001重量/体积的主题单体。在另一种实施方式中，所述非极性溶液包含约0.001至0.1重量/体积的主题单体。在又一种实施方式中，所述非极性溶液包含的所述多官能酰卤和主题芳族酸酐单体的摩尔比为约0.001:1至0.1:1，并更优选0.001:1至0.2:1。所述非极性溶液可以包括其他成分，包括如上所述的络合剂以及少量水（例如50至500ppm，在一些实施方式中至少100ppm）。
在另一种实施方式中，所述主题芳族酸酐单体在界面聚合基本完成之前、期间或之后，单独施加于多孔载体的表面（例如从单独的溶液施加）。在这种实施方式中，所述涂层溶液优选是如前所述的非极 性溶液，并优选包含浓度约0.5至5%重量/体积、或更优选约1至3%重量/体积的主题芳族酸酐单体。所述溶液可以包含其他成分，包括如上所述的络合剂以及少量水（例如50至500ppm，在一些实施方式中至少100ppm）。
虽然不局限于具体类型的聚酰胺膜，但本发明特别适合应用于复合膜，例如通常用于RO和NF应用的复合膜，更尤其是用在RO和NF应用中的平板复合聚酰胺膜。所述薄膜聚酰胺层可以任选地在它的表面的至少一部分上包含吸湿性聚合物。这样的聚合物包括聚合物表面活性剂、聚丙烯酸、聚乙酸乙烯酯、聚氧化烯化合物、聚(噁唑啉)化合物、聚丙烯酰胺和相关的反应产物，如US6280853、US7815987、US7882963、US7905361、US7918349和US2011/0284454中的总体描述。在一些实施方式中，这样的聚合物可以掺合和/或反应，并且可以从共同的溶液涂布或以其他方式施加于聚酰胺膜，或相继施加。
已经描述了本发明的许多实施方式，并且在有些情况下，某些实施方式、选择、范围、成分或其他特征已经被表征为“优选的”。“优选”特征的表征决不能被解释为认为这样的特征是本发明要求的、必需的或关键的。前述美国专利文献每一个的全部主题通过引用并入本文。
实施例：
样品膜利用中试规模的膜生产线生产。聚砜载体从在二甲基甲酰胺（DMF）中的16.5wt%溶液浇铸，随后浸泡在3.5wt%间苯二胺（mPD）水溶液中。然后将所生成的载体恒速牵拉通过反应台，同时施加非极性溶液的均匀薄层。所述非极性溶液包含异链烷烃（ISOPAR L）、均苯三甲酰氯（TMC）、和在样品2-4中各种量的1,3-二氧代-1,3-二氢异苯并呋喃-5-磺酰氯。用来制备每个样品的非极性溶液的总酰氯含量保持在0.24%w/v不变。所述非极性溶液还含有与TMC的化学计量摩尔比为大约1.3:1的磷酸三丁酯。除去多余的非极性溶液，所生成的复合膜通过水洗槽和干燥箱。然后利用盐水溶液（2000ppm NaCl），在150psi、pH8和室温下对所述样品膜的试件进行标准压力测试。如下面提供的表1中 概括的结果证明，当与类似的对照和比较膜相比较时，用所述主题磺酰氯单体制备的膜表现出较低的盐透过率。
表1：
Claims (6)
1.用于制造包含多孔载体和薄膜聚酰胺层的复合聚酰胺膜的方法，其中所述方法包括向所述多孔载体的表面施加多官能胺单体和多官能酰卤单体并且界面聚合所述单体以形成薄膜聚酰胺层的步骤，并且其中所述方法特征在于包括以下步骤中的至少一个：
i)在包含至少一个磺酰卤官能团的芳族酸酐单体存在下进行界面聚合，或
ii)向所述薄膜聚酰胺层施加所述芳族酸酐单体；
其中所述芳族酸酐单体由式(III)表示，
式(III):
其中X是卤素。
2.权利要求1的方法，其中向所述多孔载体的表面施加多官能单体的步骤包括施加包含所述多官能胺单体的极性溶液和包含所述多官能酰卤单体的非极性溶液；并且其中所述非极性溶液还包含所述芳族酸酐单体。
3.权利要求1的方法，其中所述芳族酸酐单体包含至少一个磺酰氯官能团。
4.权利要求1的方法，其中所述芳族酸酐单体包含苯环部分。
5.权利要求1的方法，其中所述芳族酸酐单体包含1,3-二氧代-1,3-二氢异苯并呋喃-5-磺酰氯。
6.权利要求1的方法，其中所述界面聚合在式(II)表示的化合物存在下进行：
式(II):
其中“P”是磷，“O”是氧，并且R1、R2和R3独立地选自含碳部分。
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| US9610542B2 (en) | 2012-07-19 | 2017-04-04 | Dow Global Technologies Llc | Composite polyamide membrane with increased carboxylic acid functionality |
| US9895666B2 (en) | 2013-01-14 | 2018-02-20 | Dow Global Technologies Llc | Composite polyamide membrane made using substituted benzamide monomer |
| CN104918687A (zh) | 2013-01-14 | 2015-09-16 | 陶氏环球技术有限责任公司 | 使用非极性溶剂的掺合物经由界面聚合制造复合聚酰胺膜 |
| US9289729B2 (en) | 2013-03-16 | 2016-03-22 | Dow Global Technologies Llc | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
| CN105163837B (zh) | 2013-05-03 | 2017-05-10 | 陶氏环球技术有限责任公司 | 衍生自脂肪族非环状叔胺化合物的复合聚酰胺膜 |
| EP3077089B1 (en) | 2013-12-02 | 2018-02-28 | Dow Global Technologies LLC | Method of forming a composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid |
| EP3077088B1 (en) | 2013-12-02 | 2017-12-27 | Dow Global Technologies LLC | Method for forming a composite polyamide membrane post treated with nitrious acid |
| KR102289354B1 (ko) | 2014-01-09 | 2021-08-12 | 다우 글로벌 테크놀로지스 엘엘씨 | 높은 산 함량 및 낮은 아조 함량을 갖는 복합 폴리아미드 막 |
| CN105848765B (zh) | 2014-01-09 | 2020-02-14 | 陶氏环球技术有限责任公司 | 具有优选偶氮含量的复合聚酰胺膜 |
| CN105899283A (zh) | 2014-01-09 | 2016-08-24 | 陶氏环球技术有限责任公司 | 具有偶氮含量和高酸含量的复合聚酰胺膜 |
| JP2017513703A (ja) | 2014-04-28 | 2017-06-01 | ダウ グローバル テクノロジーズ エルエルシー | 亜硝酸で後処理される複合ポリアミド膜 |
| US9943810B2 (en) | 2014-05-14 | 2018-04-17 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
| CN110605035A (zh) * | 2018-06-14 | 2019-12-24 | 中国科学院大连化学物理研究所 | 一种高通量聚酰胺纳滤或反渗透复合膜及其制备 |
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