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(12) United States Patent (10) Patent No.: US 8,524,796 B2 Kim Et Al

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(12) United States Patent (10) Patent No.: US 8,524,796 B2 Kim Et Al US008524796B2 (12) United States Patent (10) Patent No.: US 8,524,796 B2 Kim et al. (45) Date of Patent: *Sep. 3, 2013 (54) ACTIVE POLYMER COMPOSITIONS WO 20060967.91 9, 2006 WO 2007024.125 3, 2007 (75) Inventors: Young-Sam Kim, Midland, MI (US); WO 20070785682007030791 3,7/2007 2007 Leonardo C. Lopez, Midland, MI (US); WO 2007099397 9, 2007 Scott T. Matteucci, Midland, MI (US); WO 2007121458 10/2007 Steven R. Lakso, Sanford, MI (US) WO 2008101051 8, 2008 WO 2008112833 9, 2008 (73) Assignee: Dow Global Technologies LLC WO 2008.150970 12/2008 WO 2009 134824 11, 2009 (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 U.S.C. 154(b) by 457 days. Ciferri, Alberto, “Supramolecular Polymers'. Second Edition, 2005, pp. 157-158, CRC Press. This patent is Subject to a terminal dis Corbin et al., “Chapter 6 Hydrogen-Bonded Supramolecular Poly claimer. mers: Linear and Network Polymers and Self-Assembling Discotic Polymers'. Supramolecular Polymers, 2nd edition, CRC Press, (21) Appl. No.: 12/539,793 2005, pp. 153-185. Duan et al., “Preparation of Antimicrobial Poly (e-caprolactone) (22) Filed: Aug. 12, 2009 Electrospun Nanofibers Containing Silver-Loaded Zirconium Phos phate Nanoparticles”, Journal of Applied Polymer Sciences, 2007. (65) Prior Publication Data vol. 106, pp. 1208-1214, Wiley Periodicals, Inc. US 201O/OO41292 A1 Feb. 18, 2010 Hagewood, "Potential of Polymeric Nanofibers for Nonwovens and Medical Applications'. Fiberjournal.com, Feb. 26, 2008, 4 Pages, Related U.S. Application Data J.Hagewood, LLC and Ben Shuler, Hills, Inc. Khil et al., “Electrospun Nanofibrous Polyurethane Membrane as (60) Provisional application No. 61/088,537, filed on Aug. Wound Dressing”, Wiley Periodicals, Inc., 2003, pp. 675-679. 13, 2008. Koevoets et al., “Molecular Recognition in a Thermoplastic Elastomer'. Journal of the American Chemical Society, 2005, pp. (51) Int. Cl. 2999-3003, vol. 127. A6IL 9/04 (2006.01) Krook et al., “Barrier and mechanical properties of injection molded COSL 77/00 (2006.01) montmorillonite/polyesteramide nanocomposites'. Polymer Engi C08G 69/00 (2006.01) neering and Science, 2005, pp. 135-141, vol. 45 No. 1. (52) U.S. Cl. Lips et al., “Incorporation of different crystallizable amide blocks in USPC ........... 523/102:523/105:523/122:524/602; segmented poly(ester amide)s'. Polymer, 2005, pp. 7834-7842, vol. 46, Elsevier Ltd. 528/291; 106/15.05 Lips et al., “Synthesis and characterization of poly(ester amide)S (58) Field of Classification Search containing crystallizable amide segments'. Polymer, 2005, pp. 7823 USPC ......... 523/102,105, 122; 524/602; 528/291; 7833, vol. 46, Elsevier Ltd. 106/15.05 Liu et al., “The preparation and properties of biodegradable See application file for complete search history. polyesteramide composites reinforced with nano-CaCO3 and nano SiO2, Materials Letters, 2007, pp. 4216-4221, vol. 61, Elsevier Ltd. (56) References Cited Zou et al., "Stabilization and mechanical properties of biodegradable aliphatic polyesteramide and its filled composites'. Polymer Degra U.S. PATENT DOCUMENTS dation and Stability, 2004, pp. 87-92, vol. 83, Elsevier Ltd. 6,034,163 A 3, 2000 Barbee et al. 6,172,167 B1 1/2001 Stapert et al. * cited by examiner 6,821.479 B1 1 1/2004 Smith et al. 6,833,104 B2 12/2004 Berger 6,852,410 B2 2/2005 Veedu et al. Primary Examiner — Tae HYoon 6,897,349 B2 5, 2005 Gibbins et al. 6,967.261 B1 1 1/2005 Soerens et al. (57) ABSTRACT 7,235,295 B2 6/2007 Laurencin et al. 8,268,042 B2* 9/2012 Lopez et al. ...................... 95/52 The instant invention generally provides an activated polymer 8,343,257 B2 * 1/2013 Matteucci et al. ................ 95/45 composition containing an active agent (i.e., a chemically- or 2004/0180201 A1 9, 2004 Veedu et al. biologically-active agent), an activated fiber comprising the 2005, 0100501 A1 5, 2005 Veedu et al. activated polymer composition, an activated-fiber composite 2005/01701.92 A1 8, 2005 Kambe et al. comprising the activated fiber and a fiberweb support, pro 2006.0034907 A1 2/2006 Nagaike et al. 2008.OOO8739 A1* 1/2008 Hossainy et al. ............. 424/426 cesses of fabricating the activated fiber and activated-fiber 2008.009 1233 A1 4/2008 Ellis-Behnke et al. composition, and an article comprising the activated polymer 2008, 0214743 A1 9, 2008 Broos et al. composition. The instant invention also generally provides a 2010.0041857 A1 2/2010 Harris et al. highly filled polymer filler composite comprising a molecu 2010/0179284 A1* 7, 2010 Ward et al. ................... 525,542 larly self-assembling (MSA) material and a mineral filler or 2010/0200494 A1* 8, 2010 Storer et al. ............... 210,510.1 conductive filler dispersed in the MSA material, and a process FOREIGN PATENT DOCUMENTS of making and article comprising the highly filled polymer EP O376323 7, 1990 filler composite. WO 0042105 T 2000 WO O3O28O39 4/2003 8 Claims, 8 Drawing Sheets U.S. Patent Sep. 3, 2013 Sheet 1 of 8 US 8,524,796 B2 & 3. 500 x 58 in 80 kV s: SSE 45 is U.S. Patent Sep. 3, 2013 Sheet 2 of 8 US 8,524,796 B2 Fig. 2 U.S. Patent Sep. 3, 2013 Sheet 3 of 8 US 8,524,796 B2 23 18 x 4.8 in 1000 kW 2.0 3.1 E.S. A+E S. Fig. 3 U.S. Patent Sep. 3, 2013 Sheet 4 of 8 US 8,524,796 B2 20 ------------------------------------------------------------------------------------ SS a riggr 60 C2C-50 S. - - C2C-505wt% Jetfil 625C ----':....... 40 C2C-50+ Owt% Jetfil 625C. ----------------------------------- C2C-50 + 20wt% Jetfit 625C 20 oC2C-50 + 3Owt. Jetfil 625C V - C2C-50 + 40wt.% Jetfi 625C Yes aga 0 C2C-50+50wt% Jetfil 625C. ...............................................corror O OO 2OO 300 400 500 600 Temperature, C Fig. 4 U.S. Patent Sep. 3, 2013 Sheet 7 of 8 US 8,524,796 B2 sessessee infied PEA-C2C6.9% 1E--05 PA - 66 W / Min-Si c 1.E--04 is 1.E+03 - O S. E-02 - dis 1.E.01 . “r-a-roooooo-o-o-o-o-o-o: 1.E+00 k--- O. 1 10 100 Frequency, Radfs Fig. 7 U.S. Patent Sep. 3, 2013 Sheet 8 of 8 US 8,524,796 B2 Fig. 8 US 8,524,796 B2 1. 2 ACTIVE POLYMER COMPOSITIONS the process comprising the steps of elongating under fiber forming conditions either a melt comprising the MSA mate CROSS-REFERENCE TO RELATED rial or a solution comprising a solvent and the MSA material; APPLICATION(S) and contacting one or more active agents to the MSA material to produce one or more activated fibers of the second embodi This application claims benefit of priority from U.S. Pro ment. visional Patent Application No. 61/088,537, filed Aug. 13, In a fifth embodiment, the instant invention is a process of 2008, which application is incorporated by reference herein making the activated-fiber composite of the third embodi in its entirety. ment, the process comprising the steps of elongating under The present invention is in the field of polymer composi 10 fiber-forming conditions either a melt comprising the MSA tions and fibers comprising the polymer compositions. material or a solution comprising a solvent and the MSA material; contacting one or more active agents to the MSA BACKGROUND OF THE INVENTION material to produce one or more activated fibers of the second embodiment; and operatively contacting the one or more U.S. Pat. No. 6,852,410 B2 and its divisional USPAPN US 15 activated fibers to a fiberweb support to make the activated 2005/0100501 A1 mention single-wall carbon nanotube fiber composite of the third embodiment. (SWNT)-PAN composites and SWNT-PAN composite fibers In a sixth embodiment, the instant invention is an article fabricated therefrom. comprising the activated polymer composition of the first There is a need in the polymer art for polymer composi embodiment. Preferably, the activated polymer composition tions containing chemically- and biologically-active agents, comprises the activated fiber or activated-fiber composite of fibers comprising the polymer compositions, processes of the second or third embodiments, respectively. Preferably, the fabricating Such fibers, and articles comprising Such polymer article comprises abandage, medical gown, medical scaffold, compositions and fibers. cosmetic, Sound insulation, barrier material, diaper cover stock, adult incontinence pants, training pants, underpad, SUMMARY OF THE INVENTION 25 feminine hygiene pad, wiping cloth, porous filter medium (e.g., for filtering air, gasses, or liquids), durable paper, fabric The instant invention generally provides an activated poly softener, home furnishing, floor covering backing, geotextile, mer composition comprising a molecularly self-assembling apparel, apparel interfacing, apparel lining, shoe, industrial material and an active agent (i.e., a chemically- or biologi garment, protective garments and fabrics, agricultural fabric, cally-active agent), an activated fiber comprising the acti 30 automotive fabric, coating Substrate, laminating Substrate, vated polymer composition, an activated-fiber composition leather, or electronic component. comprising the activated fiber and a fiberweb support, pro In a seventh embodiment, the article of the sixth embodi cesses of fabricating the activated fiber and activated-fiber ment comprises an activated woven or co-woven fabric. composition, and an article comprising the activated polymer Accordingly, the instant invention also comprises a woven composition. 35 fabric comprising one or more activated fibers (e.g., activated In a first embodiment, the instant invention is an activated filament(s)) of the second embodiment. The woven fabric is polymer composition comprising a molecularly self-assem prepared by a process comprising a step of weaving an MSA bling (MSA) material and one or more active agents, wherein fiber (e.g., MSA filament) useful in the second embodiment each active agent independently comprises odor control or the activated fiber of the second embodiment to provide the material, polyelectrolyte, chelating agent, microspheres, 40 woven fabric.
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