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1 738 生物工程学报 Chinese Journal of Biotechnology DOI: /j.cjb 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 June 25, 2016, 32(6): Chin J Biotech, All rights reserved 综述 (PHA) 周迎鑫, 杨楠, 王希媛, 翁云宣, 刁晓倩, 张敏, 靳玉娟 ,. (PHA)., 2016, 32(6): Zhou YX, Yang N, Wang XY, et al. Biomanufactured polyhydroxyalkanoates (PHA) modification: a review. Chin J Biotech, 2016, 32(6): 摘要 : 本文简述了生物制造聚羟基烷酸酯 (PHA), 包括聚 3- 羟基丁酸酯 (PHB) 聚 (3- 羟基丁酸酯 -3- 羟基戊酸酯 ) (PHBV) 聚 (3- 羟基丁酸酯 -4- 羟基丁酸酯 ) (P3/4HB) 聚 (3- 羟基丁酸酯 -3- 羟基己酸酯 ) (PHBH) 的产业化现状, 综述了针对 PHA 材料热稳定性差加工窗口较窄等缺点而进行的一些改性研究选用适当方法对 PHA 进行改性, 可使其性能得到优化, 应用领域得到拓展 : 聚羟基烷酸酯, 生物改性, 化学改性, 物理改性 Biomanufactured polyhydroxyalkanoates (PHA) modification: a review Yingxin Zhou, Nan Yang, Xiyuan Wang, Yunxuan Weng, Xiaoqian Diao, Min Zhang, and Yujuan Jin Materials Science and Engineering Department, Beijing Technology and Business University, Beijing , China Abstract: In this review, we presented the industrial status of biomanufactured polyhydroxyalkanoates (PHA), including poly (3-hydroxybutyrate) (PHB), poly (3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), poly (3-hydroxybutyrate-co- 4-hydroxybutyrate) (P3/4HB)), and poly (3-hydroxybutyrate-3-hydroxycaproate) (PHBH). A lot of modification studies, aimed at solving problems of poor thermal stability, narrow processing window and other drawbacks of PHA, are discussed. The properties of PHA can be optimized by using proper modification method, in order to expand its applications. Keywords: polyhydroxyalkanoates, biological modification, chemical modification, physical modification Received: January 13, 2016; Accepted: April 25, 2016 Supported by: National Natural Science Foundation of China (Nos , , , ). Corresponding author: Yunxuan Weng. Tel/Fax: ; wyxuan@th.btbu.edu.cn (Nos , , , )

2 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 739 (PHA) [1] [2] [3] PHA [4] [5] [6] [7] PHA PHA PHA 1 PHA 的种类 100 PHA [8] PHA PHA (scl-pha short chain length PHA) 3 5 C PHA (mcl-pha: medium chain length PHA) 6 16C PHA (scl-mcl-pha) PHA PHA (Homopolymer) PHA (Random copolymer) PHA (Block copolymer) PHA 3- (PHB) [9] ( ) (PHBV) [10] ( ) (PHBHP) ( ) (P3/4HB) [11] ( ) (PHBH) [12] PHB PHA PHBV PHBH PHBH PHB PHB PHBH PHB, PHBH 2 PHA 产业化发展过程 PHA [13] PHA ( ) [14] [15] 1925 PHB Lemoigne 3- (3HB) PHB [16] ICI PHA PHA PHA PHB PHBV P3/4HB cjb@im.ac.cn

3 740 ISSN CN /Q Chin J Biotech June 25, 2016 Vol.32 No.6 表 1 国内外 PHA 生产企业及产能一览 Table 1 PHA manufacturers and capacity thereof in China and abroad [17-18] Manufacturers Types of PHA Productivity (t/a) Proposed projects (t/a) Biocycle, Brazil PHB 100 Biomers, Germany PHB / Ningbo Tianan Biologic PHBV Material Co. Ltd Procter & Gamble Co. PHBH / Kaneka Corporation, Japan PHBH Metabolix Inc. P3/4HB Archer Daniels Midland Company P3/4HB / Tianjin GreenBio Materials Co., Ltd P3/4HB Shenzhen Ecomann Biotechnology Co. Ltd P3/4HB / 1 PHA Biocycle 100 t/ Biomers t/ Metabolix 350 t/ ( ICI (Zeneca) Metilabox ) t/ P&G Kaneka PHBH t/ [17] Kaneka t/ PHBV t/ t/ ADM Metabolix [18] t/ 2 P3/4HB t/ t/ PHA PHA PHA PHA [19] 2.1 生物改性 PHA PHA PHA PHA [20] PHA PHA [21] PHB PHB PHB PHB PHB ICI PHBV [22] Biopol PHB PHBV PHBV (HV)

4 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 741 HV (HB) HV Tanadchangsaeng [23] [P(3HB-co-3HV-co-4HV)] Ishida [24] 4HBA 4HB P3/4HB 3HB 4HB 4HB 4HB 4HB [25] 4HB P3/4HB 4HB [26] PHBH PHBH 3HH (Aeromonas hydrophila 4AK4) PHBH PHBH 3HH PHBH 3H 3H [27] A. hydrophila 4AK4 PHBH A. hydrophila 4AK4 PHBH 3H 15% 3% 12% PHBH PHA PHA 2.2 化学改性 PHA PHA [28] 60Coγ (MA) PHB MA PHB 42.2 [29] (DCP) (GMA) PHBV GMA PHBV PHBV PHA [30] PHB (PCL) PHB-co-PCL PHB-co-PCL PCL 2.3 物理改性 PHA cjb@im.ac.cn

5 742 ISSN CN /Q Chin J Biotech June 25, 2016 Vol.32 No.6 PHA (PEO) (PEO) Na [31] P (3HB) P[(3HB)-co-(3HP)] PEO (Mn= ) PEO [32] PHB PEO PEO PHB PHB (PBS) (PBS) [33] Ma [34] PHB PHBV PBS PBS PHBV PBS 20% PHB/PBS 400% (PPC) (PPC) (PO) [35] [36] (GMA) PHBV PHBV-GMA (MA-PPC) PHBV/PPC MA-PPC PHBV (PBAT) - (PBAT) [37] [38] PHBV/PBAT PBAT PHBV PHBV PBAT 50% PHBV (PLA) (PLA) [39] PLA PHA PLA (1) PHB/PLA [40] PHB (PLLA) [41] PLLA PEO PHB PHB PHB/PLLA/PEO (2) PHBV/PLA [42] PHBV/PLA PLA PHBV PHBV Zhao [43] PHBV PLA PHBV/PLA

6 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 743 PHBV 15% 30% [44] PLA PPC PHBV PLA/PPC/PHBV PPC PLA PPC 60% 170% PLA/PPC/PHBV (40/40/20) (3) PHBH/PLA Zhao [45] PHBH/PLA [46] PLA/PHBH PHBH PLA/PHBH PLA/PHBH (W/W)=20/80 Lim [47] PLA/PHBH PHBH PLA PHBH PLA/PHBH PLA/PHBH (80/20) PLA 3.2 MPa 68.7 MPa [48] PLLA/PHBH PLLA PHBH PLLA PLLA PLLA/PHBH (W/W)=70/30 PHBH PLLA PHBH ( ) PLA PHBH PLA PHBH [49-50] TGA PHBH/PLA PHBH/PLA (80/20 wt%) PHBH 38% 15.7% PHA Grillo [51] PHB PEG200 PHB PHB PHB PHB Bibers [52] PEG LaPorl503 Laprol5003 PHB 5% 20% PHB Janigová [53] PHB PHB PHB Wang [54] PHB PHBH ATBC ATBC PHB cjb@im.ac.cn

7 744 ISSN CN /Q Chin J Biotech June 25, 2016 Vol.32 No.6 3 结论 PHA REFERENCES [1] Huang JB, Shang LA. Advance in biosynthesis of polyhydroxyalkanoate. Chem Ind Eng Prog, 2011, 30(9): (in Chinese).,.., 2011, 30(9): [2] McChalicher CWJ, Srienc F. Investigating the structure-property relationship of bacterial PHA block copolymers. J Biotech, 2007, 132(3): [3] Ciesielski S, Możejko J, Pisutpaisal N. Plant oils as promising substrates for polyhydroxyalkanoates production. J Clean Prod, 2015, 106: [4] Antipov EM, Dubinsky VA, Rebrov AV, et al. Strain-induced mesophase and hard-elastic behaviour of biodegradable polyhydroxyalkanoates fibers. Polymer, 2006, 47(15): [5] Khosravi-Darani K, Bucci DZ. Application of polyhydroxyalkanoate in food packaging: improvements by nanotechnology. Chem Biochem Eng Quart, 2015, 29(2): [6] Xu XY, Li XT, Peng SW, et al. The behaviour of neural stem cells on polyhydroxyalkanoate nanofiber scaffolds. Biomaterials, 2010, 31(14): [7] Lv HX, Yang ZQ, Lv XY, et al. Biocompatibility of surface modified PHBHHx with rat embryonic neural stem cells. Chin J Biotech, 2012, 28(10): (in Chinese).,,,. PHBHHx., 2012, 28(10): [8] Chuah JA, Tomizawa S, Yamada M, et al. Characterization of site-specific mutations in a short-chain-length/ medium-chain-length polyhydroxyalkanoate synthase: in vivo and in vitro studies of enzymatic activity and substrate specificity. Appl Environ Microbiol, 2013, 79(12): [9] Chen Q, Zhang LH. Study on synthesis of PHB by moderate halophile and aqueous extraction of PHB. Appl Mech Mater, 2014, : [10] Nanda MR, Misra M, Mohanty AK. The effects of process engineering on the performance of PLA and PHBV blends. Macromol Mater Eng, 2011, 296(8): [11] Chen ZF, Cheng ST, Xu KT. Block poly(ester-urethane)s based on poly (3-hydroxybutyrate-co-4-hydroxybutyrate) and poly (3-hydroxyhexanoate-co-3-hydroxyoctanoate). Biomaterials, 2009, 30(12): [12] Ye HM, Wang Z, Wang HH, et al. Different thermal behaviors of microbial polyesters poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3- hydroxyhexanoate) and poly(3-hydroxybutyrateco-3-hydroxyhexanoate). Polymer, 2010, 51(25): [13] Liu HF, Ding XL, Zhou G, et al. Electrospinning of nanofibers for tissue engineering applications. J Nanomater, 2013, 2013: [14] Chen GQ, Zhang JY, Wang Y. White Biotechnology for biopolymers: hydroxyalkanoates and polyhydroxyalkanoates: production and applications//pandey A, Hofer R, Larroche C, et al, Eds. Industrial Biorefineries & White Biotechnology. Amsterdam: Elsevier, 2015: [15] Yan Q, Li Y, Chen J, et al. Progress on the

8 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 745 biosynthesis of medium-chain-length polyhydroxyalkanoates by microorganisms. Chin J Biotech, 2001, 17(5): (in Chinese).,,,.., 2001, 17(5): [16] Sudesh K, Doi Y. Molecular design and biosynthesis of biodegradable polyesters. Polym Adv Technol, 2000, 11(8/12): [17] Weng YX, Zhou YX, Zhang M. The development and commercialization of biobased, biodegradable plastics in China. Ind Biotech, 2014, 10(2): [18] Chen GQ. Current status and industrialization of biopolyesters polyhydroxyalkanoate (PHA). New Chem Mater, 2010, 38(10): 1 7 (in Chinese).. (PHA)., 2010, 38(10): 1 7. [19] Hu FQ, You S, Chen GQ. Synthesis of medium-chain-length polyhydroxyalkanoate (mcl PHA) in type I PHA synthase negative mutant of Aeromonas hydrophila. Chin J Biotech, 2005, 21(4): (in Chinese).,,. (mcl PHA) Ⅰ PHA., 2005, 21(4): [20] Ansari NF, Amirul AA. Preparation and characterization of polyhydroxyalkanoates macroporous scaffold through enzyme-mediated modifications. Appl Biochem Biotech, 2013, 170(3): [21] Lu XY, Wu Q, Zhang WJ, et al. Studies on synthesis of polyhydroxyalkanoate consisting of 3-hydroxyvalerate by Aeromonas hydrophila. Chin J Biotech, 2004, 20(5): (in Chinese).,,,. 3-., 2004, 20(5): [22] Yu ZF, Ding YC, Yang YY, et al. Research progress on biopolyester polyhydroxyalkanoate (PHA) modifications. Polym Bull, 2010, (11): 1 9 (in Chinese).,,,. PHA., 2010, (11): 1 9 (in Chinese). [23] Tanadchangsaeng N, Yu J. Miscibility of natural polyhydroxyalkanoate blend with controllable material properties. J Appl Polym Sci, 2013, 129(4): [24] Ishida K, Wang Y, Inoue Y. Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha. Biomacromolecules, 2001, 2(4): [25] Zhang SY, Cong CB, Xu RW, et al. Research of poly (3-hydroxybutyrate-co-4-hydroxybutyrate) copolymers's physical properties. J Beijing Univ Chem Technol, 2007, 34(S2): (in Chinese).,,,. (3- )-(4- )., 2007, 34(S2): [26] Li H, Ouyang SP, Wu Q, et al. Effect of n-butanol on microbial production of copolyesters consisting of 3-hydroxybutyrate and 3-hydroxyhexanoate by Aeromonas hydrophila 4AK4. Chin Biotechnol, 2003, 23(11): (in Chinese).,,, (PHBHHx)., 2003, 23(11): [27] Ouyang SP, Qiu YZ, Wu Q, et al. Fermentative production of poly(3-hydroxybutyrate-co- 3-hydroxyhexanoate) (PHBHHx) by recombinant Aeromonas hydrophila 4AK4 (ptg01). Chin J Biotech, 2003, 19(6): (in Chinese).,,,. Aeromonas hydrophila 4AK PHBHHx., 2003, 19(6): [28] Ye HR, Yang DZ, Hu P, et al. Grafting of maleic anhydride onto poly(β-hydroxybutyrate) by 60 coγ radiation. Acta Polym Sin, 2005, (4): (in Chinese) cjb@im.ac.cn

746 ISSN 1000-3061 CN 11-1998/Q Chin J Biotech June 25, 2016 Vol.32 No.6,,,. β-., 2005, (4): 678 682. [29] Li J.

9 746 ISSN CN /Q Chin J Biotech June 25, 2016 Vol.32 No.6,,,. β-., 2005, (4): [29] Li J. Thermal properties and morphology of graft copolymers for PHBV-GMA and PHBV-GMA/PPC blend. Polym Bull, 2010, (6): (in Chinese).. PHBV-GMA PHBV-GMA/PPC., 2010, (6): [30] Chen C, Fei B, Peng SW, et al. Study on the transesterification of poly(β-hydroxybutyrate) and poly(ε-caprolactone). Acta Polym Sin, 2002, (2): (in Chinese).,,,. β- ε-., 2002, (2): [31] Na YH, Yong H, Asakawa N, et al. Miscibility and phase structure of blends of poly(ethylene oxide) with poly(3-hydroxybutyrate), poly(3- hydroxypropionate), and their copolymers. Macromolecules, 2002, 35(3): [32] Wang WJ, Song XL, Yu PD, et al. Study on the mechanical properties and pheological behaviors of PEO/PHB blends[c]//chinese Chemical Society 28th Annual Meeting of the 18th Session Abstracts. Beijing: Chinese Chemical Society, 2012 (in Chinese).,,,. PEO/PHB [C]// :, [33] Choudhury N, Sarma BK. Structural analysis of chemically deposited nanocrystalline PbS films. Thin Solid Films, 2011, 519(7): [34] Ma PM, Hristova-Bogaerds DG, Lemstra PJ, et al. Toughening of PHBV/PBS and PHB/PBS blends via in situ compatibilization using dicumyl peroxide as a free-radical grafting initiator. Macromol Mater Eng, 2012, 297(5): [35] Chen WF, Xiao M, Wang SJ, et al. Preparation and properties of biodegradeble blends of poly(propylene carbonate) and poly(lactic acid). Polym Mater Sci Eng, 2010, 26(3): (in Chinese).,,,. /., 2010, 26(3): [36] Li J, Sun CR, Zhang XQ. Thermal properties, dynamic mechanical properties and morphology of PHBV/PPC reactive blends. Polym Mater Sci Eng, 2013, 29(3): (in Chinese).,,. PHBV/PPC., 2013, 29(3): [37] Fukushima K, Rasyida A, Yang MC. Biocompatibility of organically modified nanocomposites based on PBAT. J Polym Res, 2013, 20: 302. [38] Ouyang CF, Jia RP, Wang X, et al. Morphology and properties of PHBV/PBAT blends. China Plast, 2008, 22(6): (in Chinese).,,,. PHBV /PBAT., 2008, 22(6): [39] Pang X, Zhuang XL, Tang ZH, et al. Polylactic acid (PLA): research, development and industrialization. Biotech J, 2010, 5(11): [40] Ge J, Li ZB, Gao QG. The study of crystallinity of biodegradable polymer poly(l-lactide) and polyhydroxybutyrate blend film. Acta Scient Natural Univ Sunyat, 2011, 50(5): (in Chinese).,, 橋. PLLA/PHB. ( ), 2011, 50(5): [41] Du JH, Yang QF, Fan XD. Crystalline structure and tensile properties of PHB/PLLA/PEO blend fiber. China Synth Fiber Ind, 2012, 35(2): (in Chinese).,,. PHB/PLLA/PEO., 2012, 35(2): [42] Zhu FC, Yu B, Han J. Structure and miscibility of

10 周迎鑫等 / 聚羟基烷酸酯 (PHA) 改性研究进展 747 poly(3-hydroxybutyrate-co-hydroxyvalerate) and poly(lactic acid) blends for melt-blown nonwovens. Polym Mater Sci Eng, 2014, 30(8): 81 84, 90 (in Chinese).,,. PHBV/PLA., 2014, 30(8): 81 84, 90. [43] Zhao HB, Cui ZX, Wang XF, et al. Processing and characterization of solid and microcellular poly(lactic acid)/polyhydroxybutyrate-valerate (PLA/PHBV) blends and PLA/PHBV/Clay nanocomposites. Compos Part B: Eng, 2013, 51: [44] Tao J, Hu D, Liu L, et al. Thermal characteristics, mechanical properties and degradability of PLA/PPC/PHBV blends. Ion Exch Adsorpt, 2010, 26(1): (in Chinese).,,,. PLA, PPC PHBV., 2010, 26(1): [45] Zhao Q, Wang SF, Kong MM, et al. Phase morphology, physical properties, and biodegradation behavior of novel PLA/PHBHHx blends. J Biomed Mater Res Part B, 2012, 100B(1): [46] Wang SF, Guo TY, Yang C, et al. Mechanical properties and biodegradability of poly(lactic acid)/poly(3-hydroxybutyrate-co-3-hydroxyhexano ate)(pla/phbhhx) blends. Ion Exch Adsorpt, 2006, 22(1): 1 8 (in Chinese).,,,. β- β- / (PHBHHx/PLA)., 2006, 22(1): 1 8. [47] Lim JS, Park KI, Chung GS, et al. Effect of composition ratio on the thermal and physical properties of semicrystalline PLA/PHB-HHx composites. Mater Sci Eng: C, 2013, 33(4): [48] Zhang S, Jia D, Ding CK, et al. Effect of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) on the crystalline properties of poly(l-lactic acid). China Plast, 2013, 27(1): (in Chinese).,,,.., 2013, 27(1): [49] Zhou YX, Huang ZG, Diao XQ, et al. Characterization of the effect of REC on the compatibility of PHBH and PLA. Polym Test, 2015, 42: [50] Zhou YX, Diao XQ, Weng YX, et al. Compatibility of PHBH/PLA blends. China Plast, 2015, (4): (in Chinese).,,,. PHBH/PLA., 2015, (4): [51] Grillo Fernandes E, Pietrini M, Chiellini E. Thermo-mechanical and morphological characterization of plasticized poly[(r)-3- hydroxybutyric acid]. Macromol Symp, 2004, 218(1): [52] Bibers I, Tupureina V, Dzene A, et al. Improvement of the deformative characteristics of poly-β-hydroxybutyrate by plasticization. Mech Compos Mater, 1999, 35(4): [53] Janigová I, Lacı k I, Chodák I. Thermal degradation of plasticized poly (3-hydroxybutyrate) investigated by DSC. Polym Degrad Stabil, 2002, 77(11): [54] Wang L, Zhu WF, Wang XJ, et al. Processability modifications of poly(3-hydroxybutyrate) by plasticizing, blending, and stabilizing. J Appl Polym Sci, 2008, 107(1): ( 本文责编陈宏宇 ) cjb@im.ac.cn

Microsoft Word gc 刁晓倩

Microsoft Word gc 刁晓倩生物工程学报 Chinese Journal of Biotechnology DOI: 10.13345/j.cjb.160058 刁晓倩等 / 国内生物基材料产业发展现状 June 25, 2016, 32(6): 715 725 2016 Chin J Biotech, All rights reserved 综述 715 刁晓倩 1,2, 翁云宣 1,2, 黄志刚 1,2, 杨楠 1, 王希媛