journal article·2015-06Open access

Development of cardanol-bonded cellulose thermoplastics: high productivity achieved in two-step heterogeneous process

Kiyohiko Toyama, Makoto Soyama, Shukichi Tanaka, Masatoshi Iji

Cellulose· Volume 22· Issue 3

Abstract

We developed a heterogeneous process with low energy consumption to synthesize novel high-strength and heat-resistant cellulose-based bioplastics: cellulose esters bonded with a short chain component (acetic acid) and a long one (3-pentadecylphenoxy acetic acid; PAA), which is a derivative of cardanol, extracted from cashew nut shells. Although we recently showed that PAA-bonded cellulose acetates (cardanol-bonded cellulose resins) exhibit highly practical properties for durable products, they were synthesized in a homogeneous process, which requires large quantities of poor solvents to isolate the resins. In the developed two-step heterogeneous process, the cardanol-bonded cellulose resins are produced without poor solvents. In the first step, cellulose is esterified with limited amounts of the long and short chain components using a selected reaction solvent and catalyst. The resultant intermediate products are adequately swollen in the solvent then efficiently recovered by filtration. In the second step, the short chain component is additionally bonded to attain good thermoplasticity of the final products, which are readily recovered only by distilling a solvent and the remaining short chain component. The solvent usage was reduced by approximately 90 % compared with a homogeneous process, which leads to a large reduction in energy. The produced cardanol-bonded cellulose resins exhibited higher thermoplasticity, elastic modulus, water resistivity, and close heat resistivity compared to that of a homogeneous process. Furthermore, the mechanical and thermal characteristics of the resins were greatly improved by adding a specific polyester, polybutylene succinate adipate, and glass fiber, reaching high-level target properties for durable products.
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Research context

OpenAlex topics: Advanced Cellulose Research Studies · Ginkgo biloba and Cashew Applications · Catalysis for Biomass Conversion

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References (27)

Show source-provided references
1. Bogan RT, Brewer RJ (1985) Cellulose Esters, Organic. In: Mark HF, Bikales N, Overberger CG, Menges G, Kroschwitz JI (eds), Encyclopedia of polymer science and engineering vol 3, Wiley, New York, pp 158–181
2. Edgar KJ, Pecorini TJ, Glasser WG (1998) Preparation, properties, and perspective, cellulose derivatives, chapter 3: 38–60, ACS symposium series, vol 688. American Chemical Society, Washington
3. Edgar KJ, Buchanan CM, Debenham JS, Rundquist PA, Seiler BD, Shelton MC, Tindall D (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–168810.1016/S0079-6700(01)00027-2 ↗
4. Enomoto-Rogers Y, Kamitakahara H, Takano T, Nakatsubo F (2009) Cellulosic graft copolymer: poly(methacrylate) with cellulose side chain. Biomacromolecules 10:2110–211710.1021/bm900229g ↗
5. Freire CSR, Gandini A (2006) Recent advances in the controlled heterogeneous modification of cellulose for the development of novel materials. Cellulose Chem Technol 40:691–698
6. Hwan-Man P, Manjusri M, Lawrence TD, Mohanty AK (2004) Green nanocomposites from cellulose acetate Bioplastic and clay: effect of eco-friendly triethyl citrate plasticizer. Biomacromolecules 5:2281–228810.1021/bm049690f ↗
7. Iji M, Moon S, Tanaka S (2011) Hydrophobic, mechanical, and thermal characteristics of thermoplastic cellulose diacetate bonded with cardanol from cashew nut shell. Polym J 43:738–74110.1038/pj.2011.57 ↗
8. Iji M, Toyama K, Tanaka S (2013) Mechanical and other characteristics of cellulose ester bonded with cardanol from cashew nut shells and additional aliphatic and aromatic components. Cellulose 20:559–56910.1007/s10570-012-9832-z ↗
9. Kumar PP, Parmashivappa R, Vithayathil PJ, Rao PVS, Rao AS (2002) Process for isolation of cardanol from technical cashew (Anacardium occidentale L.) nut shell liquid. J Agric Food Chem 50:4705–470810.1021/jf020224w ↗
10. Li S, Ernst W, Martin P (2010) Present and future development in plastics from biomass. Biofuels Bioprod Biorefining 4(1):25–4010.1002/bbb.189 ↗
11. Lubi MC, Thachil ET (2000) Cashew nut shell liquid (CNSL)—a versatile monomer for polymer synthesis. Des Monomers Polym 3(2):123–15310.1163/156855500300142834 ↗
12. Matsumura H, Sugiyama J, Glasser WG (2000) Cellulosic Nanocomposites. I. Thermally deformable cellulose hexanoates from heterogeneous reaction. J Appl Polym Sci 78:2242–225310.1002/1097-4628(20001220)78:13<2242::AID-APP20>3.0.CO;2-5 ↗
13. Nie L, Narayan R (1994) Grafting cellulose acetate with styrene maleic anhydride random copolymers for improving dimensional stability. J Appl Polym Sci 54:601–61710.1002/app.1994.070540511 ↗
14. Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: review. Chem Soc Rev 38:2046–206410.1039/b808639g ↗
15. Sealey JE, Samaranayake G, Todd JG, Glasser WG (1996) Novel cellulose derivatives. IV. Preparation and thermal analysis of waxy esters of cellulose. J Polym Sci B Poly Phys 34:1613–162010.1002/(SICI)1099-0488(19960715)34:9<1613::AID-POLB10>3.0.CO;2-A ↗
16. Serizawa S, Inoue K, Iji M (2006) Kenaf-fiber-reinforced poly(lactic acid) used for electronic products. J Appl Polym Sci 100(1):618–62410.1002/app.23377 ↗
17. Soyama M, Iji M, Tanaka S, Toyama K (2014) Development of cardanol-bonded cellulose resin using non-food plant resources (2): improvement in practical characteristics including impact strength. Polym Prepr Jpn 63:3683–3684
18. Tanaka S, Honzawa H, Iji M (2013) Development of cardanol-bonded cellulose thermoplastics: high productivity achieved by using isocyanate-modified cardanol. J Appl Polym Sci 130:1578–158710.1002/app.39313 ↗
19. Tanaka S, Toyama K, Soyama M, Iji M (2014) Development of cardanol-bonded cellulose thermoplastics: two step heterogeneous synthesis process with low energy. Preprints of the 21th annual meeting of the Cellulose Society of Japan: K18
20. Teramoto Y, Nishio Y (2003) Cellulose diacetate-graft-poly(lactic acid)s: synthesis of wide-ranging compositions and their thermal and mechanical properties. Polymer 44:2701–270910.1016/S0032-3861(03)00190-3 ↗
21. Teramoto Y, Nishio Y (2004) Biodegrable cellulose diacetate-graft-poly(L-lactide): enzymatic hydrolysis behavior and surface morphological characterization. Biomacromolecules 5:407–41410.1021/bm034453i ↗
22. Tezuka Y, Tsuchiya Y (1995) Determination of substituent distribution in cellulose acetate by means of a 13C NMR study on its propanoated derivative. Carbohydr Res 273:83–9110.1016/0008-6215(95)00107-5 ↗
23. Toyama K, Soyama M, Tanaka S, Iji M (2014a) Development of cardanol-bonded cellulose resin using non-food plant resources: low energy heterogeneous synthesis process. Preprints of the 248th ACS national meeting: POLY 68310.1021/bk-2015-1192.ch020 ↗
24. Toyama K, Tanaka S, Iji M (2014b) Development of cardanol-bonded cellulose resin using non-food plant resources (1): low energy heterogeneous synthesis process. Polym Prepr Jpn 63:3681–3682
25. Yan C, Zhang J, Lv Y, Yu J, Wu J, Zhang J, He J (2009) Thermoplastic cellulose-graft-poly(L-lactide)copolymers homogeneously synthesized in an ionic liquid with 4-dimethylaminopyridine catalyst. Biomacromolecules 10(8):2013–201810.1021/bm900447u ↗
26. Yoshioka M, Hasegawa N, Shiraishi N (1999) Themoplastization of cellulose acetates by grafting of cyclic esters. Cellulose 6:193–21210.1023/A:1009221730934 ↗
27. Zepnik S, Kesselring A, Kopitzky R, Michels C (2010) Basics of cellulosics. Bioplastic Mag 5:44–47