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(12) United States Patent (10) Patent No.: US 9,724,649 B2 Stasiak Et Al

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(12) United States Patent (10) Patent No.: US 9,724,649 B2 Stasiak Et Al USOO9724649B2 (12) United States Patent (10) Patent No.: US 9,724,649 B2 Stasiak et al. (45) Date of Patent: Aug. 8, 2017 (54) SELF-WETTING POROUS MEMBRANES (I) (56) References Cited (71) Applicant: PALL CORPORATION, Port U.S. PATENT DOCUMENTS Washington, NY (US) 3,318,959 A 5, 1967 Borman 3,847,867 A 11/1974 Heath et al. (72) Inventors: Marcin Stasiak, Port Washington, NY (Continued) (US); Hassan Ait-Haddou, Melville, NY (US) FOREIGN PATENT DOCUMENTS EP O318787 A2 6, 1989 (73) Assignee: Pall Corporation, Port Washington, EP 296274.6 A1 1, 2016 NY (US) (Continued) (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U.S.C. 154(b) by 168 days. European Patent Office, Extended European Search Report issued in European Patent Application No. 16167135.9 (Oct. 27, 2016) 5 pp. (21) Appl. No.: 14/750,382 (Continued) Primary Examiner — Taiwo Oladapo (22) Filed: Jun. 25, 2015 (74) Attorney, Agent, or Firm — Leydig, Voit & Mayer, Ltd. Prior Publication Data (65) (57) ABSTRACT US 2016/0375409 A1 Dec. 29, 2016 Disclosed is a self-wetting porous membrane comprising an aromatic hydrophobic polymer Such as polysulfone and a (51) Int. C. wetting agent comprising a copolymer of formula A-B or A-B-A, wherein A is a hydrophilic segment comprising a BOLD 7L/06 (2006.01) polymerized monomer of the formula (I): CH=C(R')(R), BOLD 69/06 (2006.01) wherein R' and R are as described herein, and B is an (Continued) aromatic hydrophobic polymeric segment, wherein seg (52) U.S. C. ments B and A are linked through an amidoalkylthio group. CPC ........... B01D 69/06 (2013.01); B01D 61/246 Also disclosed is a method of preparing a self-wetting (2013.01); B0ID 6770013 (2013.01); membrane comprising casting a solution containing an aro (Continued) matic hydrophobic polymer and the wetting agent, followed (58) Field of Classification Search by Subjecting the cast solution to phase inversion. The CPC ... B01D 69/06; B01D 67/0013; B01D 71/62; self-wetting porous membrane finds use in hemodialysis, B01D 61/246; B01D 71/06; B01D 71/60; microfiltration, and ultrafiltration. (Continued) 20 Claims, 1 Drawing Sheet US 9,724,649 B2 Page 2 (51) Int. Cl. Asif, et al., “Hydroxyl Terminated Poly(ether ether ketone) with Pendant Methyl Group-Toughened Epoxy Clay Ternary BOLD 67/00 (2006.01) Nanocomposites: Preparation, Morphology, and Thermomechanical BOLD 7L/68 (2006.01) Properties,” Journal of Applied Polymer Science, vol. 106, pp. BOLD 7L/80 (2006.01) 2936-2946 (2007). BOID 6/24 (2006.01) Dizman, Cemil, et al., “Synthesis of polysulfone-b-polystyrene BOLD 7L/60 (2006.01) block copolymers by mechanistic transformation from condensation polymerization, to free radical polymerization.” Polymer Bulletin, BOLD 7L/62 (2006.01) vol. 70, pp. 2097-2109 (2013). B29C 39/00 (2006.01) Francis, Bejoy, et al., “Synthesis of Hydroxyl-Terminated B29K 81/OO (2006.01) Poly(ether ether ketone) with Pendent tert-Butyl Groups and Its Use B29L 3 I/OO (2006.01) as a Toughener for Epoxy Resins,” Journal of Polymer Science. Part B. Polymer Physics, vol. 44, pp. 541-556 (2006). (52) U.S. Cl. Rifle, J.S., et al., “Synthesis of Hydroxyl-Terminated Polycarbon CPC ......... BOID 6770016 (2013.01); B0ID 71/06 ates of Controlled Number-Average Molecular Weight.” Journal of (2013.01); B0ID 71/60 (2013.01); B0ID Polymer Science. Polymer Chemistry Edition, vol. 20, pp. 2289 2301 (1982). 71/62 (2013.01); B0ID 71/68 (2013.01); Wang, Jianyu, et al., “Amphiphilic ABA copolymers used for BOID 71/80 (2013.01); B29C 39/006 surface modification of polysulfone membranes, Part 1: Molecular (2013.01); B01D 2325/36 (2013.01); B01D design, synthesis, and characterization, Polymer, vol. 49, pp. 2325/38 (2013.01); B29K 2081/06 (2013.01); 3256-3264 (2008). B29L 2031/755 (2013.01) Yang, Jung-Eun, et al., “Synthesis and Morphology Studies of a (58) Field of Classification Search Polystyrene-Poly(arylene ether sulfone)-Polystyrene Coil-Semirod CPC ... B01D 67/0016; B01D 71/68; B01D 71/80; Coil Triblock Copolymer.” Macromolecules, vol.39, pp. 3038-3042 (2006). B01D 2325/38; B01D 2325/36; B29C Yi. Zhuan, et al., “An extending of candidate for the hydrophilic 39/006; B29K 2081/06; B29L 2031/755 modification of polysuifone membranes from the compatibility See application file for complete search history. consideration: The polyetherSulfone-based amphiphilic copolymer as an example,” Journal of Membrane Science, vol. 390-391, pp. (56) References Cited 48-57 (2012). Yi. Zhuan, et al., “Effects of coagulant pH and ion strength on the U.S. PATENT DOCUMENTS dehydration and self-assembly of poly(N,N-dirnethylamino-2-ethyl methacrylate) chains in the preparation of Stimuli-responsive 4,611,048 A 9, 1986 Peters 5,911,880 A * 6/1999 Klein ................. BO1D 67 OO11 polyethersulfone blend membranes,” Journal of Membrane Science, 210,493.1 vol. 463, pp. 49-57 (2014). 6,113,785 A 9, 2000 Miura et al. Zhang, Ying, et al., “Structure and Properties of Poly(butyl acrylate 7,230,066 B2 6, 2007 Khouri et al. block-sulfone-block-butyl acrylate) Triblock Copolymers Prepared 7,695,628 B2 * 4/2010 Steiger ................... BO1D 71,68 by ATRP, " Macromolecular Chemistry and Physics, vol. 206, pp. 210,500.28 33-42 (2005). 2011 O240550 A1 10/2011 Moore et al. Zhao, Yi-Fan, et al., “Versatile antifouling polyetherSuifone filtra 2015,015.1256 A1 6, 2015 Abetz et al. tion membranes modified via Surface grafting of Zwitterionic poly mers from a reactive amphiphilic copolymer additive,” Journal of FOREIGN PATENT DOCUMENTS Colloid and Interface Science, vol. 448, pp. 380-388 (2015). Zhao, Yi-Fan, et al., “Improving the hydrophilicity and fouling JP S62-201603. A 9, 1987 resistance of polysulfone ultrafiltration membranes via Surface JP HO2-160026. A 6, 1990 Zwitterionicalization mediated by poly Suifone-based triblock copo JP HT-19653 A 8, 1995 lymer additive,” Journal of Membrane Science, vol. 440, pp. 40-47 WO WO 2011/123033 A1 6, 2011 (2013). WO WO 2012/047961 A1 4/2012 Zhao, Yi-Fan, et al "Zwitterionic hydrogel thin films as antifouling WO WO 2014, 181931 A1 11, 2014 Surface layers of polyetherSulfone ultrafiltration membranes WO WO 2015, O75178 A1 5/2015 anchored via reactive copolymer additive,” Journal of Membrane Science, vol. 470, pp. 148-158 (2014). OTHER PUBLICATIONS Korean Intellectual Property Office, Notice of Non-Final Rejection issued in Korean Patent Application No. 10-2016-0051975 (dated Intellectual Property Office of Singapore, Search Report issued in Apr. 18, 2017) 11 pp. Singapore Application No. 10201603247R (Jul. 25, 2016). Japanese Patent Office, Notice of Reasons for Rejection issued in Barton et al., “The effect of phenols and aromatic thiols on the Japanese Patent Application No. 2016-088420 (dated May 23, polymerization of methyl methacrylate'. Canadian Journal of 2017) 6 pp. Chemistry, vol. 41, No. 11, pp. 2737-2742 (1963). Pending U.S. Appl. No. 14/750,443, filed Jun. 25, 2015. * cited by examiner U.S. Patent Aug. 8, 2017 US 9,724,649 B2 US 9,724,649 B2 1. 2 SELF-WETTING POROUS MEMBRANES (I) BRIEF DESCRIPTION OF THE DRAWING BACKGROUND OF THE INVENTION The FIGURE depicts the SEM micrograph of a self wetting porous membrane in accordance with an embodi Aromatic hydrophobic polymers such as polysulfone and ment of the invention illustrated in Example 10. polyetherSulfone are attractive as membrane polymers for one or more of the following reasons: a high glass transition DETAILED DESCRIPTION OF THE temperatures, amorphous glassy state, thermal and oxidative INVENTION stability, excellent strength and flexibility, resistance to extreme pHs, and low creep even at elevated temperatures. 10 In an embodiment, the invention provides a self-wetting However, these polymers are inherently hydrophobic and porous membrane comprising an aromatic hydrophobic therefore porous membranes made from these polymers are polymer and a wetting agent comprising a copolymer of not wettable by water. formula A-B or A-B-A, wherein A is a hydrophilic segment Attempts have been made to improve the surface wetta 15 comprising a polymerized monomer or mixture of mono bility of porous membranes made from Such polymers by mers, wherein the monomer is of the formula (I): numerous methods including coating and crosslinking a hydrophilic polymer, grafting of hydrophilic monomers by e-beam, gamma radiation, or UV or other radiation, Surface wherein R' is hydrogen or alkyl, and R is selected from oxidation, Surface-initiated free radical grafting, blending substituted or unsubstituted heterocyclyl, substituted or with hydrophilic additives such as polyvinylpyrrolidone unsubstituted heteroaryl, formylamino, formylaminoalkyl, (PVP), copolymers of PVP polyvinylalcohol (PVA), copo aminocarbonyl, alkylcarbonyloxy, and aminocarbonylalkyl lymers of PVA, polyethylene oxide (PEO), copolymers of Substituted with a Zwitterionic group, and B is an aromatic PEO and polypropylene oxide, and in situ polymerization of hydrophobic polymeric segment, wherein segments B and A hydrophilic monomers. 25 are linked through an amidoalkylthio group. “A” further Drawbacks are associated with one or more of the above comprises an end group. attempted methods. For example, with the methods involv The term "heterocyclyl as used herein refers to a mono ing blending of hydrophilic additives, the additives tend to cyclic heterocyclic group or a bicyclic heterocyclic group. leach out of the porous membrane on prolonged use in The monocyclic heterocycle is a three-, four-, five-, six- or aqueous environments. Approaches involving coating and 30 seven-membered ring containing at least one heteroatom crosslinking a hydrophilic polymer tend to shrink or modify independently selected from the group consisting of O, N, the membrane pores, thereby limiting the usefulness of the N(H) and S. The three- or four-membered ring contains Zero membranes.
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