Citation: CAI Yi, GUO Hongchen, CAO Han, GAO Fengxiang, ZHOU Qinghai, WANG Xianhong. Synthesis and Properties of Ultraviolet-Irradiation Resistant Carbon Dioxide Copolymer[J]. Chinese Journal of Applied Chemistry, ;2019, 36(11): 1248-1256. doi: 10.11944/j.issn.1000-0518.2019.11.190210 shu

Synthesis and Properties of Ultraviolet-Irradiation Resistant Carbon Dioxide Copolymer

  • Corresponding author: WANG Xianhong, xhwang@ciac.ac.cn
  • Received Date: 15 July 2019
    Revised Date: 20 August 2019
    Accepted Date: 10 September 2019

    Fund Project: the Science and Technology Service Network Initiative of Chinese Academy of Sciences(STS) KFJ-STS-QYZD-047Supported by the Science and Technology Service Network Initiative of Chinese Academy of Sciences(STS)(No.KFJ-STS-QYZD-047)

Figures(7)

  • CO2 based plastics (PPC) is a high molecular mass copolymer of carbon dioxide and propylene oxide. PPC is quite sensitive to ultraviolet (UV) irradiation and its molecular mass decreases quickly with UV-irradiation accompanied by significant loss of mechanical strength. To improve the UV irradiation resistance of PPC is of key importance for its application as agricultural mulching film, which is always under UV irradiation during the whole coverage. In this work, an epoxide with UV absorber function, i.e., 2-hydroxy-4(2, 3-epoxypropoxy)benzophenone (HEB), was designed and prepared. By means of terpolymerization of CO2, propylene oxide and HEB, terpolymer PPCH with UV absorber side chain was successfully synthesized, where the chemical structure as well as the HEB content was determined by 1H NMR spectroscopy. Under the premise of ensuring PPCH molecular mass not less than 5.0×104, the maximum molar fraction of HEB incorporated into the PPCH terpolymer was 0.32%, and such PPCH showed a tensile strength of 30.97 MPa, a glass transition temperature (Tg) of 26.7℃, and the temperature at 5% mass loss of thermal decomposition (Td-5%) of 216.9℃. When PPC was exposed under UV irradiation for 240 h, its number-average molecular mass decreased by 67.8%, accompanied by 10.1% loss of tensile strength and 40.1% loss of elongation at break. As a comparison, the number-average molecular mass of PPCH with 0.06% molar fraction HEB showed only 6.2% decrease correspondingly. It showed 1.7% loss of tensile strength and 13.3% decrease of elongation at break, indicating that PPCH had improved UV-irradiation resistance performance due to the existence of UV absorbable functional group like HEB. PPCH and PPC blended with similar 2, 4-dihydroxyl benzophenone (BP) content were compared for hot water (50℃) extraction test. No BP was extracted in PPCH providing stable UV absorption performance, while the PPC/BP blend showed sharp drop in UV absorption upon hot water extraction. Therefore, terpolymerization of CO2, propylene oxide with UV absorbable monomer is an effective way to improve the UV irradiation resistance performance of CO2 copolymer.
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    1. [1]

      Inoue S, Koinuma H, Tsuruta T. Copolymerization of Carbon Dioxide and Epoxide[J]. J Polym Sci, Part B:Polym Lett, 1969,7:287-292. doi: 10.1002/pol.1969.110070408

    2. [2]

      Coates G W, Moore D R. Discrete Metal-Based Catalysts for the Copolymerization of CO2 and Epoxides:Discovery, Reactivity, Optimization, and Mechanism[J]. Angew Chem Int Ed, 2004,43:6618-6639. doi: 10.1002/anie.200460442

    3. [3]

      Klaus S, Lehenmeier M W, Anderson C E. Recent Advances in CO2/Epoxide Copolymerization-New Strategies and Cooperative Mechanisms[J]. Coord Chem Rev, 2011,255:1460-1479. doi: 10.1016/j.ccr.2010.12.002

    4. [4]

      Qin Y S, Sheng X F, Liu S J. Recent Advances in Carbon Dioxide Based Copolymers[J]. J CO2 Util, 2015,11:3-9. doi: 10.1016/j.jcou.2014.10.003

    5. [5]

      Grignard B, Gennen S, Jerome C. Advances in the Use of CO2 as a Renewable Feedstock for the Synthesis of Polymers[J]. Chem Soc Rev, 2019,48:4466-4514. doi: 10.1039/C9CS00047J

    6. [6]

      Kamphuis A J, Picchioni F, Pescarmona P P. CO2-Fixation into Cyclic and Polymeric Carbonates:Principles and Applications[J]. Green Chem, 2019,21:406-448. doi: 10.1039/C8GC03086C

    7. [7]

      Nakano K, Kamada T, Nozaki K. Selective Formation of Polycarbonate over Cyclic Carbonate:Copolymerization of Epoxides with Carbon Dioxide Catalyzed by a Cobalt(Ⅲ) Complex with a Piperidinium End-Capping Arm[J]. Angew Chem Int Ed, 2006,45:7274-7277. doi: 10.1002/anie.200603132

    8. [8]

      Sujith S, Min J K, Seong J E. Highly Active and Recyclable Catalytic System for CO2/Propylene Oxide Copolymerization[J]. Angew Chem Int Ed, 2008,47:7306-7309. doi: 10.1002/anie.200801852

    9. [9]

      Wang Y, Qin Y S, Wang X H. Trivalent Titanium Salen Complex:Thermally Robust and Highly Active Catalyst for Copolymerization of CO2 and Cyclohexene Oxide[J]. ACS Catal, 2014,5:393-396.

    10. [10]

      Zhuo C W, Qin Y S, Wang X H. Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO2 and Propylene Oxide[J]. Chinese J Polym Sci, 2017,36:252-260.  

    11. [11]

      Zhuo C W, Qin Y S, Wang X H. Temperature-Responsive Catalyst for the Coupling Reaction of Carbon Dioxide and Propylene Oxide[J]. Chinese J Chem, 2018,36:299-305. doi: 10.1002/cjoc.201800019

    12. [12]

      Liu S J, Miao Y Y, Qiao L J. Controllable Synthesis of a Narrow Polydispersity CO2-Based Oligo(Carbonate-Ether) Tetraol[J]. Polym Chem, 2015,6:7580-7585. doi: 10.1039/C5PY00556F

    13. [13]

      Liu S J, Qin Y S, Qiao L J. Cheap and Fast:Oxalic Acid Initiated CO2-Based Polyols Synthesized by a Novel Preactivation Approach[J]. Polym Chem, 2016,7:146-152. doi: 10.1039/C5PY01338K

    14. [14]

      Huang Z, Wang Y, Zhang N. One-Pot Synthesis of Ion-Containing CO2-Based Polycarbonates Using Protic Ionic Liquids as Chain Transfer Agents[J]. Macromolecules, 2018,51:9122-9130. doi: 10.1021/acs.macromol.8b01834

    15. [15]

      Yang G W, Zhang Y Y, Wang Y Y. Construction of Autonomic Self-healing CO2-Based Polycarbonates via One-Pot Tandem Synthetic Strategy[J]. Macromolecules, 2018,51:1308-1313. doi: 10.1021/acs.macromol.7b02715

    16. [16]

      Ren G J, Miao Y Y, Qiao L J. Toughening of Amorphous Poly(Propylene Carbonate) by Rubbery CO2-Based Polyurethane:Transition from Brittle to Ductile[J]. RSC Adv, 2015,5:49979-49986. doi: 10.1039/C5RA07142A

    17. [17]

      Qin Y S, Wang X H. Carbon Dioxide-Based Copolymers:Environmental Benefits of PPC, an Industrially Viable Catalyst[J]. Biotechnol J, 2010,5:1164-1180. doi: 10.1002/biot.201000134

    18. [18]

      GAO Fengxiang, ZHOU Qinghai, QIN Yusheng, et al. Preparation of Carbon Dioxide-Propylene Oxide Copolymer Foam: CN, 103304977.A[P]. 2013-09-18(in Chinese).

    19. [19]

      Liu Z R, Hu J J, Gao F X. Biodegradable and Resilient Poly(propylene carbonate) Based Foam from High Pressure CO2 Foaming[J]. Polym Degrad Stabil, 2019,165:12-19. doi: 10.1016/j.polymdegradstab.2019.04.019

    20. [20]

      ZHOU Qinghai, WANG Xianhong, GAO Fengxiang, et al. Fabrication of Full Biodegradable Films Based on Polypropylene Carbonate: CN, 101402789.2009-04-08(in Chinese).

    21. [21]

      Muthuraj R, Mekonnen T. Recent Progress in Carbon Dioxide (CO2) as Feedstock for Sustainable Materials Development:Co-polymers and Polymer Blends[J]. Polymer, 2018,145:348-373. doi: 10.1016/j.polymer.2018.04.078

    22. [22]

      Liu S J, Wang X H. Polymers from Carbon Dioxide:Polycarbonates, Polyurethanes[J]. Curr Opin Green Sustainable Chem, 2017,3:61-66. doi: 10.1016/j.cogsc.2016.08.003

    23. [23]

      Jackson R A, Oldland S R, Pajaczkowski A. Diffusion of Additives in Polyolefins[J]. J Appl Polym Sci, 1968,12:1297-1309. doi: 10.1002/app.1968.070120603

    24. [24]

      Uhde W J, Woggon H. New Results on Migration Behavior of Benzophenone-Based UV Absorbents from Polyolefins in Foods[J]. Die Nahrung, 1976,20(2):185-194. doi: 10.1002/food.19760200212

    25. [25]

      Li C F, Li Y, Chen Z L. Simultaneous Determination of Migration Amounts of Antioxidants and Ultraviolet Absorbents Byhighperformance Liquid Chromatographyin Food Contact Materials[J]. Chinese J Chromatogr, 2014,6:616-622.

    26. [26]

      Lin Q B, Liang X Z, Su Q Z. Effect of Graphene on the Migration of Two Ultraviolet Absorbents from Graphene-LDPE Composite Films into a Fatty Food Simulant[J]. Food Packaging Shelf, 2017,12:9-15. doi: 10.1016/j.fpsl.2017.01.008

    27. [27]

      Bailey D, Tirrell D, Pinazzi C. Polymers of 2, 4-Dihydroxy-4'-vinylbenzophenone, New Polymeric Ultraviolet Absorbers[J]. Macromolecules, 1978,11(2):312-320. doi: 10.1021/ma60062a006

    28. [28]

      Parmar R J, Saxena S, Parmar J S. Copolymerization of UV-Absorbers, II[J]. Angew Makromol Chem, 1998,259:1-5. doi: 10.1002/(SICI)1522-9505(19981001)259:1<1::AID-APMC1>3.0.CO;2-6

    29. [29]

      LI Hua, ZHEN Yubin, WANG Lin. Study on Synthesis of Polymeric Ultraviolet Absorber I. Emulsion Polymerization of Acrylate Containing 2-Hydroxy-4-Acryloyloxbenzonphenone[J]. China Synth Resin Plast, 2004,2:56-58, 70. doi: 10.3969/j.issn.1002-1396.2004.02.014

    30. [30]

      Liu N, Pan J Q, Lau W W Y. Preparations and Properties of New Monomeric Light Stabilizers[J]. Polym Degrad Stabil, 1999,63(1):71-77.

    31. [31]

      ZHANG Yaming, CAI Yi, ZHOU Qinghai, et al. Preparation of a Zinc-Dicarboxylate Catalyst, Modified Zinc-Dicarboxylate Catalyst and Carbon Dioxide-Epoxy Copolymer:CN, 105418907A[P]. 2016-03-23(in Chinese).

    32. [32]

      ZHANG Mingzheng, LI Ran, HUANG Dan. Microwave Syntheses and Characterization of 1, 2-Epoxy Propyl Ether Aromatic Ketone UV Absorbents[J]. Chemistry, 2014,77(12)1201.  

    33. [33]

      ZHAO Yi, DAN Yi. Synthesis of a Reactive UV-Stabilizer and Its Application in Styrenic Polymers[J]. Polym Mater Sci Eng, 2006,5:74-77. doi: 10.3321/j.issn:1000-7555.2006.05.018

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