Citation: Wei Zhao, Chuan-Yang Li, Chun-Ji Wu, Xin-Li Liu, Ze-Huai Mou, Chang-Guang Yao, Dong-Mei Cui. Synthesis of Ultraviolet Absorption Polylactide via Immortal Polymerization of rac-Lactide Initiated by a Salan-yttrium Catalyst[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 202-206. doi: 10.1007/s10118-018-2050-x shu

Synthesis of Ultraviolet Absorption Polylactide via Immortal Polymerization of rac-Lactide Initiated by a Salan-yttrium Catalyst

Wei Zhao ^a,c,† ,
Chuan-Yang Li ^a,b,† ,
Chun-Ji Wu ^a ,
Xin-Li Liu ^a ,
Ze-Huai Mou ^a,b ,
Chang-Guang Yao ^a,b ,
Dong-Mei Cui ^a,,

a.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
University of Chinese Academy of Sciences, Changchun Branch, Changchun 130022, China
c.
College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China

Corresponding author: Dong-Mei Cui, dmcui@ciac.ac.cn

^†

Received Date: 6 September 2017
Accepted Date: 22 September 2017
Available Online: 27 November 2017

A highly efficient strategy for the synthesis of polylactide with the UV absorption ability was established by employing a Salan-yttrium complex (acting as a fast runing catalyst) combined with large excess hydroxyl functionalized benzophenone, BP'-OH. During polymerization, BP'-OH, acting as the chain transfer agent, attached to the active rare-earth metal catalyst via a rapid-reversible exchange reaction to initiate the polymerization. Thus, more polyester chains appeared to grow from one active metal species, and the UV absorption fragments were incorporated into the polymer chains at specific sites, in situ. A high productivity up to 1000 mol_LA/mol_(Salan-Y) was successfully achieved and 100 BP'-labeled PLA chains grew from each active metal center.
- Yttrium catalyst,
- Ring-opening polymerization,
- Polylactide,
- Ultraviolet absorption
1. [1]
  Drumright R. E., Gruber P. R., Henton D. E.. Polylactic acid technology[J]. Adv. Mater., 2000,12:1841-1846. doi: 10.1002/(ISSN)1521-4095
2. [2]
  Mecking S.. Nature or Petrochemistry? Biologically degradable materials[J]. Angew. Chem. Int. Ed., 2004,43:1078-1085. doi: 10.1002/(ISSN)1521-3773
3. [3]
  Dattaa R., Tsaia S. P., Bonsignorea P., Moona S. H., Frank J. R.. Technological and economic potential of poly(lactic acid) and lactic acid derivatives[J]. FEMS Microbiol. Rev., 1995,16:221-231. doi: 10.1111/fmr.1995.16.issue-2-3
4. [4]
  Auras R., Harte B., Selke S.. An overview of polylactides as packaging materials[J]. Macromol. Biosci., 2004,4:835-864. doi: 10.1002/(ISSN)1616-5195
5. [5]
  Nelson K. H., Cathcart W. M.. Transmission of light through pigmented polyethylene milk bottles[J]. J. Food Prot., 1984,47:346-348. doi: 10.4315/0362-028X-47.5.346
6. [6]
  Erickson M. C.. Chemical and microbial stability of fluid milk in response to packaging and dispensing[J]. Int. J. Dairy Technol., 1997,50:107-111. doi: 10.1111/idt.1997.50.issue-3
7. [7]
  Bradley R. L.. Effect of light on alteration of nutritional value and flavor of milk:a review[J]. J. Food Prot., 1980,43:314-320. doi: 10.4315/0362-028X-43.4.314
8. [8]
  Xiao P., Shi S. Q., Nie J.. Synthesis and characterization of copolymerizable one-component type Ⅱ photoinitiator[J]. Polym. Adv. Technol.,, 2008,19:1305-1310. doi: 10.1002/pat.v19:9
9. [9]
  Wu Q. H., Qu B. J.. Photoinitiating characteristics of benzophenone derivatives as new initiators in the photocrosslinking of polyethylene[J]. Polym. Eng. Sci., 2001,41:1220-1226. doi: 10.1002/(ISSN)1548-2634
10. [10]
  Xiao P., Wang Y., Dai M., Shi S., Wu G., Nie J.. Synthesis and photopolymerization kinetics of polymeric one-component type Ⅱ photoinitiator containing benzophenone moiety and tertiary amine[J]. Polym. Eng. Sci., 2008,48:884-888. doi: 10.1002/(ISSN)1548-2634
11. [11]
  Han J. Y., Jiang S. L., Gao Y. J., Sun F.. Intramolecularinitiating photopolymerization behavior of nanogels with the capability of reducing shrinkage[J]. J. Mater. Chem. C, 2016,4:10675-10683. doi: 10.1039/C6TC03839E
12. [12]
  Gritsenko K. P., Krasovsky A. M.. Thin-film deposition of polymers by vacuum degradation[J]. Chem. Rev., 2003,103:3607-3650. doi: 10.1021/cr010449q
13. [13]
  Zhao W., Li C. Y., Liu B., Wang X., Li P., Wang Y., Wu C. J., Yao C. G., Liu X. L., Cui D. M.. A new strategy to access polymers with aggregation-induced emission characteristics[J]. Macromolecules, 2014,47:5586-5594. doi: 10.1021/ma500985j
14. [14]
  Liu X. L., Shang X. M., Tang T., Hu N. H., Pei F. K., Cui D. M., Chen X. S., Jing X. B.. Achiral lanthanide alkyl complexes bearing N, O multidentate ligands. synthesis and catalysis of highly heteroselective ring-opening polymerization of rac-lactide[J]. Organometallics, 2007,26:2747-2757. doi: 10.1021/om0700359
15. [15]
  Wang Y., Zhao W., Liu X. L., Cui D. M., Chen E. Y. X.. Ligand-free magnesium catalyst system:immortal polymerization of L-lactide with high catalyst efficiency and structure of active intermediates[J]. Macromolecules, 2012,45:6957-6965. doi: 10.1021/ma3007625
16. [16]
  Zhao W., Cui D. M., Liu X. L., Chen X. S.. Facile Synthesis of Hydroxyl-ended, highly stereoregular, star-shaped poly(lactide) from immortal ROP of rac-Lactide and kinetics study[J]. Macromolecules, 2010,43:6678-6684. doi: 10.1021/ma101202g
17. [17]
  Zhao W., Liu B., Liu X. L., Wang X., Wang Y., Yao C. G., Wu C. J., Cui D. M.. Neutral lutetium complex/polyamine mediated immortal ring-opening polymerization of rac-lactide:facile synthesis of well-defined hydroxyl-end and amide-core stereoregular star polylactide[J]. Polym. Chem,, 2015,6:7711-7716. doi: 10.1039/C5PY01164G
18. [18]
  Li C. Y., Liu X. L., He S. S., Huang Y. B., Cui D. M.. Synthesis and AIE properties of PEG-PLA-PMPC based triblock amphiphilic biodegradable polymers[J]. Polym. Chem,, 2016,7:1121-1128. doi: 10.1039/C5PY01849H
19. [19]
  Amgoune A., Thomas C. M., Roisnel T., Carpentier J. F.. Ring-opening polymerization of lactide with group 3 metal complexes supported by dianionic alkoxy-amino-bisphenolate ligands:combining high activity, productivity, and selectivity[J]. Chem. Eur. J., 2006,12:169-179. doi: 10.1002/(ISSN)1521-3765
20. [20]
  Ma H., Okuda J.. Kinetics and mechanism of L-lactide polymerization by rare earth metal silylamido complexes:effect of alcohol addition[J]. Macromolecules, 2005,38:2665-2673. doi: 10.1021/ma048284l
21. [21]
  Ajellal N., Lyubov D. M., Sinenkov M. A., Fukin G. K., Cherkasov A. V., Thomas C. M., Carpentier J. F., Trifonov A. A.. Bis(guanidinate) alkoxide complexes of lanthanides:synthesis, structures and use in immortal and stereoselective ring-opening polymerization of cyclic esters[J]. Chem. Eur. J., 2008,14:5440-5448. doi: 10.1002/(ISSN)1521-3765
22. [22]
  Cowman C. D., Padgett E., Tan K. W., Hovden R., Gu Y., Andrejevic N., Muller D., Coates G. W., Wiesner U.. Multicomponent nanomaterials with complex networked architectures from orthogonal degradation and binary metal backfilling in ABC triblock terpolymers[J]. J. Am. Chem. Soc., 2015,137:6026-6033. doi: 10.1021/jacs.5b01915
23. [23]
  Thevenon A., Romain C., Bennington M. S., White A. J. P., Davidson H. J., Brooker S., Williams C. K.. Dizinc lactide polymerization catalysts:hyperactivity by control of ligand conformation and metallic cooperativity[J]. Angew. Chem. Int. Ed., 2016,55:8680-8685. doi: 10.1002/anie.201602930
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