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(12) Patent Application Publication (10) Pub. No.: US 2012/0115729 A1 Qin Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2012/0115729 A1 Qin Et Al US 201201.15729A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0115729 A1 Qin et al. (43) Pub. Date: May 10, 2012 (54) PROCESS FOR FORMING FILMS, FIBERS, Publication Classification AND BEADS FROM CHITNOUS BOMASS (51) Int. Cl (75) Inventors: Ying Qin, Tuscaloosa, AL (US); AOIN 25/00 (2006.01) Robin D. Rogers, Tuscaloosa, AL A6II 47/36 (2006.01) AL(US); (US) Daniel T. Daly, Tuscaloosa, tish 9.8 (2006.01)C (52) U.S. Cl. ............ 504/358:536/20: 514/777; 426/658 (73) Assignee: THE BOARD OF TRUSTEES OF THE UNIVERSITY OF 57 ABSTRACT ALABAMA, Tuscaloosa, AL (US) (57) Disclosed is a process for forming films, fibers, and beads (21) Appl. No.: 13/375,245 comprising a chitinous mass, for example, chitin, chitosan obtained from one or more biomasses. The disclosed process (22) PCT Filed: Jun. 1, 2010 can be used to prepare films, fibers, and beads comprising only polymers, i.e., chitin, obtained from a suitable biomass, (86). PCT No.: PCT/US 10/36904 or the films, fibers, and beads can comprise a mixture of polymers obtained from a suitable biomass and a naturally S3712). (4) (c)(1), Date: Jan. 26, 2012 occurring and/or synthetic polymer. Disclosed herein are the (2), (4) Date: an. AO. films, fibers, and beads obtained from the disclosed process. O O This Abstract is presented solely to aid in searching the sub Related U.S. Application Data ject matter disclosed herein and is not intended to define, (60)60) Provisional applicationpp No. 61/182,833,sy- - - s filed on Jun. limit, or otherwise provide the full scope of the disclosed 1, 2009. Subject matter. Patent Application Publication May 10, 2012 Sheet 1 of 10 US 2012/0115729 A1 A B - g \\? C N X e ma-rama -- y w - ? \ /NA A / - 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650 co FG. Patent Application Publication May 10, 2012 Sheet 2 of 10 US 2012/0115729 A1 620. 865 125s bes % --------" "- r - lessess-WVVV,1259,2696 A A? N. 1620.7865 W 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650 cro FG.2 Patent Application Publication May 10, 2012 Sheet 3 of 10 US 2012/0115729 A1 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650 Cir FG.3 Patent Application Publication May 10, 2012 Sheet 4 of 10 US 2012/0115729 A1 8 8 2 OO 8 8 i O ppm Patent Application Publication May 10, 2012 Sheet 5 of 10 US 2012/0115729 A1 O 200 400 600 800 1000 1200 1400 line, in FG.5 Patent Application Publication May 10, 2012 Sheet 6 of 10 US 2012/0115729 A1 5 10 5 2 25 TT 5 40 2 Theta, degrees FIG.6 Patent Application Publication May 10, 2012 Sheet 7 of 10 US 2012/0115729 A1 O OO 40 6. 80 emperature, oc FG.7 Patent Application Publication May 10, 2012 Sheet 8 of 10 US 2012/0115729 A1 88: Patent Application Publication May 10, 2012 Sheet 9 of 10 US 2012/0115729 A1 O O) CD 1 s S S. S.S s SSS.Š S SSŠ S S S S S S Š S. SSS 5. Patent Application Publication May 10, 2012 Sheet 10 of 10 US 2012/0115729 A1 Acc. V Spot Mag Det WD 20.0 kV 5.0 58X Acc. W xxxxxxSpot Magn 285 US 2012/01 15729 A1 May 10, 2012 PROCESS FOR FORMING FILMS, FIBERS, lobster, and krill), oyster, and squids. Annual synthesis of AND BEADS FROM CHTINOUS BOMASS chitin in freshwater and marine ecosystem is about 600 and 1600 million tons, respectively. Producing chitin in industry CROSS REFERENCE TO RELATED is primarily from the exoskeletons of marine crustacean shell APPLICATIONS waste by a chemical method that involves acid demineraliza tion, alkali deproteinization, and followed by decolorization. 0001. This application claims the benefit of priority to Even though the current industrialized chemical process iso U.S. Provisional Application No. 61/182,833, filed Jun. 1, lates chitin from crustacean shells efficiently, disadvantages 2009, which is incorporated by reference herein in its entirety. exist in these procedures, including, inter alia, the use of corrosive acids, bases, and strong oxidants which are not FIELD OF THE DISCLOSURE environmentally friendly. In addition, these processes can 0002 Disclosed herein is a process for forming films, modify or nullify the desired physiochemical properties of fibers, and beads comprising a chitinous mass, for example, chitin, for example, by acid demineralization, shorting the chitin and chitosan obtained from one or more biomasses. chitin chain length, as well as, degrading the chitin during The disclosed process can be used to prepare films, fibers, and deproteinization in hot alkali solutions. These undesired beads comprising only polymers, e.g., chitin, obtained from a changes in the properties of chitin can have a profound affect Suitable biomass, or the films, fibers, and beads can comprise when the chitin obtained therefrom must have specific a mixture of polymers obtained from a Suitable biomass and molecular weight distributions and degrees of acetylation a naturally occurring and/or synthetic polymer. Also, dis (DA). closed herein are the films, fibers, and beads obtained from 0007 As such, there is along felt need for films, fibers, and the disclosed process. beads formed from chitin wherein the chitin has both consis tent, as well as, desirable properties. There is also a need for BACKGROUND chitin compositions that can be efficiently and reproducibly 0003. Each year humans place an increasingly greater manufactured under environmentally friendly and mild con demand on the biosphere. The world's increasing level of ditions. Disclosed herein are processes and compositions that industrialization has come to produce a Surge in the consump address these and other needs. tion of natural resources, while at the same time producing an equally large amount of waste material that is either non SUMMARY OF THE DISCLOSURE recyclable or simply not recycled. The replacement of metals 0008. The present disclosure relates to processes for form by plastics in the last century somewhatabated the growth in ing films, fibers, and beads from a chitinous biomass. In one the demand for this resource commodity. But with the rise in aspect, chitin can be directly extracted from a chitinous bio synthetic polymer technology, came an explosion in the use mass, for example, from shrimp or crab shells and directly of synthetic polymers with the result that today plastics and used to form fibers, films, and beads which comprise chitin other synthetic polymers are the most utilized category of having a higher molecular weight than chitin derived from non-naturally occurring materials. practical grade or pure grade sources. In another aspect, an 0004 Polymers, however, are ubiquitous in nature. These ionic liquid can be used to dissolve a source of chitin in the natural building blocks have been used by mankind since first step of the process. In a further aspect, a combination of antiquity, for example, fibers made of hemp, cotton, wool, an ionic liquid and a co-solvent, for example, DMSO, can be and silk are all a part of human development. Processes used to dissolve a source of chitin in the first step of the directed to the manufacture of articles comprising recyclable process. In a yet further aspect, an organic solvent, for plant polymers such as cellulose, are well known and have example, DMSO, can be used to dissolve a source of chitin in been under development for many centuries. Less well stud the first step of the process. In a still further aspect, the ied are processes that utilize natural polymers derived from purified chitinous biomass can be combined with a naturally non-plant sources, i.e., the hard outer shells of marine ani occurring or synthetic polymer, interalia, cellulose, poly(2- mals. hydroxyethyl methacrylate (PHEMA), to form composite 0005 Chitin is the most abundant polymer in the marine films, fibers, and beads. environment. Chitin is the main component of the exoskel 0009. Additional advantages of the disclosed process will etons of arthropods, such as crustaceans and in the cell walls be set forth in part in the description which follows, and in of fungi. It has been a major source of Surface pollution in part will be obvious from the description, or can be learned by coastal areas. Both chitin and its major derivative chitosan practice of the disclosed process. The advantages of the dis (obtained by deacetylation of chitin) have numerous applica closed process will be realized and attained by means of the tions. The bioactivity, biocompatibility, and low toxicity of elements and combinations particularly pointed out in the native or chemically-modified chitin and chitosan make them appended claims. It is to be understood that both the forego Suitable for controlled drug release, cosmetics, food preser ing general description and the following detailed description Vation, fertilizer, or biodegradable packaging materials, or are exemplary and explanatory only and are not restrictive of waste water processing and other industrial applications. the disclosed process, as claimed. Chitin, however, is highly hydrophobic and is insoluble in water and most organic solvents due to the high density of BRIEF DESCRIPTION OF THE FIGURES hydrogen bonds of the adjacent chains in Solid State. The difficulty in the dissolution restricts the use of chitin as a 0010 FIG. 1 is the IR spectra of polymer films prepared by replacement for synthetic polymers. the disclosed process. Spectrum 1 A depicts the IR spectrum 0006 Crustacean shells are currently the major source of of a polymer film comprising chitin derived from shrimp chitin available for industrial processing.
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