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(12) Patent Application Publication (10) Pub. No.: US 2014/0113826A1 Fallon Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0113826A1 Fallon Et Al US 201401 13826A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0113826A1 Fallon et al. (43) Pub. Date: Apr. 24, 2014 (54) POLYSACCHARIDE ESTERMICROSPHERES A24D3/14 (2006.01) AND METHODS AND ARTICLES RELATING A618/02 (2006.01) THERETO (52) U.S. Cl. (71) Applicant: Celanese Acetate LLC, Irving, TX (US) CPC ............. A2.3L I/22016 (2013.01); A61K 8/025 (2013.01); A0IN 25/34 (2013.01); A24D 3/14 (72) Inventors: Denis G. Fallon, Blacksburg, VA (US); (2013.01) Thomas S. Garrett, Narrows, VA (US); USPC 504/358; 424/401; 424/405; 424/64; 424/69; Lawton E. Kizer, Blacksburg, VA (US); 424/63; 424/70.7; 13 1/332: 426/650: 426/648 Karen L. Zazzara, Blacksburg, VA (US); Michael T. Combs, Shady Spring, WV (US); Richard K. Johnson, Blacksburg, VA (US); Gary Dehart, (57) ABSTRACT Peterstown, WV (US) (73) Assignee: Celanese Acetate LLC, Irving, TX (US) A method for producing a polysaccharide ester microsphere may include forming a polysaccharide ester product from a (21) Appl. No.: 14/060,782 polysaccharide synthesis, wherein the polysaccharide ester (22) Filed: Oct. 23, 2013 product comprises a polysaccharide ester and a solvent, dilut e a? a 9 ing the polysaccharide ester product, thereby yielding a Related U.S. Application Data polysaccharide ester dope; and forming a plurality of polysaccharide ester microspheres from the polysaccharide (60) Provisional application No. 61/717,726, filed on Oct. ester dope. Suitable polysaccharides may include, but are not 24, 2012. limited to, starch, cellulose, hemicellulose, algenates, chito Publication Classification san, and any combination thereof. Esters thereof may be organic esters (e.g., acetate and the like), inorganic esters (51) Int. Cl. (e.g., Sulfonates and the like), or combinations thereof. Fur A2.3L. I./22 (2006.01) ther, the solids conent of the polysaccharide ester dope, in AOIN 25/34 (2006.01) Some instances, may be greater than about 16 wt %. (1.1) POLYSACCHARDEESTER SYNTHESIS --- (1.5) (12) : FILTRATION FINISHING PROCESS e- - - - - - - - - - - - - (OPTIONAL) (PRECIPITATION, WASHING, AND DRYING (1.4) DLUTION FINISHED POLYSACCHARIDE ESTER (1.3) (1.5) DOPE ; FILTRATION FORMATION (OPTIONAL) POYSACCHARIDE ESTER DOPE (1.6) FORM POLYSACCHARIDE ESTER MIRCOSPHERES Patent Application Publication Apr. 24, 2014 Sheet 1 of 15 US 2014/011382.6 A1 Patent Application Publication SWTA TWNOOW Patent Application Publication Apr. 24, 2014 Sheet 3 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 4 of 15 US 2014/011382.6 A1 s Patent Application Publication Apr. 24, 2014 Sheet 5 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 6 of 15 US 2014/011382.6 A1 8 Patent Application Publication Apr. 24, 2014 Sheet 7 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 8 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 9 of 15 US 2014/011382.6 A1 s Patent Application Publication Apr. 24, 2014 Sheet 10 of 15 US 2014/011382.6 A1 8 Patent Application Publication Apr. 24, 2014 Sheet 11 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 12 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 13 of 15 US 2014/011382.6 A1 s Patent Application Publication Apr. 24, 2014 Sheet 14 of 15 US 2014/011382.6 A1 Patent Application Publication Apr. 24, 2014 Sheet 15 of 15 US 2014/011382.6 A1 US 2014/0113826 A1 Apr. 24, 2014 POLYSACCHARDE ESTERMICROSPHERES tions, alterations, combinations, and equivalents in form and AND METHODS AND ARTICLES RELATING function, as will occur to those skilled in the art and having the THERETO benefit of this disclosure. 0007 FIG. 1 provides nonlimiting examples of methods CROSS-REFERENCE TO RELATED for forming microspheres according to at least some embodi APPLICATIONS ments described herein. 0008 FIG. 2 provides an uptake profile for a cellulose 0001. This application claims priority to U.S. Provisional ester microsphere according to at least Some embodiments Patent Application No. 61/717,726 filed on Oct. 24, 2012. described herein. 0009 FIG. 3 provides SEM micrograph of several micro BACKGROUND spheres produced according to at least some embodiments 0002 The exemplary embodiments described herein described herein. relate to polysaccharide ester microspheres and methods and 0010 FIG. 4 provides SEM micrograph of several micro articles relating thereto. spheres produced according to at least some embodiments 0003. The most common polysaccharide ester to be used described herein. in microspheres is cellulose ester. Cellulose ester micro 0011 FIG. 5 provides SEM micrograph of several micro spheres are often Substantially rigid beads that consist essen spheres produced according to at least some embodiments tially of cellulose ester and have some degree of porosity described herein. based on the method with which they are produced. Cellulose 0012 FIG. 6 provides SEM micrograph of several micro ester microspheres have proven useful for immobilizing spheres produced according to at least some embodiments enzymes and release of chemicals, especially in conjunction described herein. with filter and chromatograph packing materials. Further, (0013 FIG. 7 provides SEM micrograph of several micro cellulose ester microspheres have found some industrial Suc spheres produced according to at least some embodiments cess in pharmaceutical and cosmetic applications. However, described herein. these applications, in addition to food, personal care, agricul 0014 FIG. 8 provides SEM micrograph of several micro tural applications, and others, would benefit from and/or be spheres produced according to at least some embodiments further enabled with the ability to produce cellulose ester described herein. microspheres at lower cost and with tailored properties (e.g., (0015 FIG. 9 provides SEM micrograph of several micro release rate of additives, solubility, polarity, and strength). spheres produced according to at least some embodiments 0004 Methods for forming cellulose ester microspheres described herein. include solvent evaporation methods, precipitation methods, 0016 FIG. 10 provides SEM micrograph of several micro and emulsion methods that utilize cellulose ester flake as the spheres produced according to at least some embodiments precursor. The production of cellulose ester flake can be described herein. energy intensive, especially in the finishing process that yield 0017 FIG. 11 provides SEM micrograph of several micro the dry flake after the reactions are completed. Further, these spheres produced according to at least some embodiments production methods generally provide for batch production described herein. of cellulose ester microspheres, which increases production 0018 FIG. 12 provides SEM micrograph of several micro cost, time, and waste. For industrial uses to be a reality, a spheres produced according to at least some embodiments continuous production process is desirable to reduce cost and described herein. increase product uniformity. (0019 FIG. 13 provides SEM micrograph of several micro 0005 Additionally, tailoring the properties of the cellu spheres produced according to at least some embodiments lose ester microspheres may enable a wider breadth of appli described herein. cations than have been previously realized. For example, 0020 FIG. 14 provides SEM micrograph of several micro cosmetics are increasingly using controlled release to deliver spheres produced according to at least some embodiments Vitamins and minerals and/or release fragrances over moder described herein. ate time periods, like a day. Similarly, additives for agricul 0021 FIG. 15 provides SEM micrograph of several micro tural applications (e.g., fertilizers and pesticides) are increas spheres produced according to at least some embodiments ingly being investigated for controlled and/or long-term described herein. efficacy with single or minimal treatments. Cellulose ester microspheres have been limited in the ability to adapt the DETAILED DESCRIPTION properties to a specific additive in combination with an appli 0022. The exemplary embodiments described herein cation. For example, a desired release rate may be similar relate to polysaccharide ester microspheres and methods and between a vitamin in a cosmetic application and a pesticide in articles relating thereto. an agricultural application, but the hardness and size for the 0023. As used herein, the term “microsphere' encom respective applications may be very different. Therefore, passes shapes that are spherical, Substantially spherical, multi-dimensional tailoring of properties and production on oblong, Substantially oblong, teardrop, Substantially tear an industrial-scale may be of value in expanding the practical drop, prolate spherical, Substantially prolate spherical, and applications of cellulose ester microspheres. the like, and any hybrid thereof. 0024. The polysaccharide ester microspheres described BRIEF DESCRIPTION OF THE DRAWINGS herein comprise at least one polysaccharide ester. The com 0006. The following figures are included to illustrate cer positional versatility of polysaccharide esters and ability to tain aspects of the exemplary embodiments described herein, mix various polysaccharide esters may allow for tailoring the and should not be viewed as exclusive embodiments. The properties (e.g., size, strength, morphology, solubility, and subject matter disclosed is capable of considerable modifica polarity) of the polysaccharide ester microspheres, which US 2014/0113826
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