Citation: WEN Liang, YANG Huawei, SHI Hengchong, LUAN Shifang, YIN Jinghua, SHI Dean. Melt Functionalization of Polyethylene Initiated by N-Hydroxyphthalimide[J]. Chinese Journal of Applied Chemistry, ;2020, 37(5): 518-523. doi: 10.11944/j.issn.1000-0518.2020.05.190361 shu

Melt Functionalization of Polyethylene Initiated by N-Hydroxyphthalimide

  • Corresponding author: YANG Huawei, yanghw@ciac.ac.cn SHI Dean, deanshi2012@yahoo.com
  • Received Date: 30 December 2019
    Revised Date: 3 February 2020
    Accepted Date: 24 March 2020

    Fund Project: the National Natural Science Foundation of China 51803213Supported by the National Natural Science Foundation of China(No.51803213, No.51973052)the National Natural Science Foundation of China 51973052

Figures(2)

  • N-Hydroxyphthalimide (NOP) was used as the radical initiator in the melt graft polymerization of linear low density polyethylene (LLDPE) with four N-halamine precursors, methacrylamide (MA), N-tert-butyl acrylamide (N-t-BuA), maleimide (MI) and 2, 4-diamino-6-diallylamino-1, 3, 5-triazine (NDAM). Meanwhile, the traditional peroxide method was conducted for comparison by using dicumyl peroxide (DCP) as the free radical initiator for melt grafting. The grafting efficiency of the NOP initiator is controlled by the molecular structure and the loading level of the monomer based on the quantitative Fourier transform infrared spectrometer (FT-IR) results. N-t-BuA shows the highest grafting efficiency, which is 2.5%~16.0% lower than that in the DCP system, while MI has the least grafting efficiency, about 55% of the DCP method. However, the crosslink side reaction in the NOP system is more controllable than that in the DCP system, as revealed by the real-time torque, the gel content and the melt index data.
  • 加载中
    1. [1]

      JI Fance, LIU Xiangdong, YANG Yuming. Photothermal-Induced Shape Memory Polymers Prepared by Reactive Blending[J]. Chinese J Appl Chem, 2019,36(8):904-908.  

    2. [2]

      LI Pei, ZHANG Jiaqi, CHEN Quan. Chain Structure and Properties of Four Commercial Low Density Polyethylene Resins[J]. Chinese J Appl Chem, 2019,36(11):1237-1247.  

    3. [3]

      Al-Malaika S. Reactive Modifiers for Polymers[M]. Springer Netherlands, 1997:84-132.

    4. [4]

      Moad G. The Synthesis of Polyolefin Graft Copolymers by Reactive Extrusion[J]. Prog Polym Sci, 1999,24(1):81-142. doi: 10.1016/S0079-6700(98)00017-3

    5. [5]

      Russell K E. Free Radical Graft Polymerization and Copolymerization at Higher Temperatures[J]. Prog Polym Sci, 2002,27(6):1007-1038. doi: 10.1016/S0079-6700(02)00007-2

    6. [6]

      SHI Dean, YIN Jinghua, KE Zhuo. On the Mechanism of Melt Grafting of Isotactic Polypropylene with Maleic Anhydride[J]. Chinese J Appl Chem, 2001,18(11):865-868. doi: 10.3969/j.issn.1000-0518.2001.11.004 

    7. [7]

      Shi D, Yang J H, Yao Z H. Functionalization of Iisotactic Polypropylene with Maleic Anhydride by Reactive Extrusion:Mechanism of Melt Grafting[J]. Polymer, 2001,42(13):5549-5557. doi: 10.1016/S0032-3861(01)00069-6

    8. [8]

      Denis B, Philippe C, Jean-Jacques F. N-Acetoxy-Phthalimide(NAPI) as a New H-Abstracting Agent at High Temperature:Application to the Melt Functionalization of Polyethylene[J]. Polym Chem, 2013,4(9):2676-2679. doi: 10.1039/c3py00246b

    9. [9]

      CAI Chuanlun, XIN Zhirong, YAO Zhanhai. Grafting Acrylic Acid onto Pre-irradiated Polypropylene by Reactive Extrusion[J]. Chem J Chinese Univ, 2006,27(10):1969-1973. doi: 10.3321/j.issn:0251-0790.2006.10.034

    10. [10]

      Zhang Y, Chen J, Li H. HDPE Functionalization via High Shear Stress-Induced Initiation and Its Effects on HDPE/GF Composite[J]. Polym Eng Sci, 2008,48(11):2277-2286. doi: 10.1002/pen.21183

    11. [11]

      Badrossamay M R, Sun G. Graft Polymerization of N-tert-Butylacrylamide onto Polypropylene During Melt Extrusion and Biocidal Properties of Its Products[J]. Polym Eng Sci, 2009,49(2):359-368. doi: 10.1002/pen.21289

    12. [12]

      Zhang C, Huang Z, Lu J. Generation and Confinement of Long-lived N-Oxyl Radical and Its Photocatalysis[J]. J Am Chem Soc, 2018,140(6):2032-2035. doi: 10.1021/jacs.7b12928

    13. [13]

      Hara T, Iwahama T, Sakaguchi S. Catalytic Oxyalkylation of Alkenes with Alkanes and Molecular Oxygen via a Radical Process Using N-Hydroxyphthalimide[J]. J Org Chem, 2001,66(19):6425-6431. doi: 10.1021/jo0157977

    14. [14]

      Sato T, Otsu T. Application of Spin Trapping Technique to Radical Polymerization, 14.Initiation Reaction of Vinyl Monomers with the tert-Butoxyl Radical and Evaluation of Monomer Reactivities[J]. Macromol Chem Phys, 1977,180(5):1165-1174.  

    15. [15]

      Opeida I A, Kompanets M A, Kushch O V. N-Hydroxyphthalimide-Initiated Radical Polymerization of Vinyl Monomers[J]. Russ J Appl Chem, 2007,80(10):1717-1720. doi: 10.1134/S1070427207100230

    16. [16]

      Chen K, Xie H, Mao J. Structure-Performance Landscape of N-Alkoxyphthalimides as Organocatalysts in Aerobic Oxidation[J]. J Catal, 2016,344:229-235. doi: 10.1016/j.jcat.2016.09.015

    17. [17]

      Shanmugam K V S, Parent J S, Whitney R A. Design, Synthesis and Characterization of Bismaleimide Co-curing Elastomers[J]. Ind Eng Chem Res, 2012,51(26):8957-8965. doi: 10.1021/ie300795b

    18. [18]

      Badrossamay M R, Sun G. Durable and Rechargeable Biocidal Polypropylene Polymers and Fibers Prepared by Using Reactive Extrusion[J]. J Biomed Mater Res Part B:Appl Biomater, 2009,98B(1):93-101.  

    19. [19]

      Badrossamay M R, Sun G. Preparation of Rechargeable Biocidal Polypropylene by Reactive Extrusion with Diallylamino Triazine[J]. Eur Polym J, 2008,44(3):733-742. doi: 10.1016/j.eurpolymj.2007.12.005

    20. [20]

      Cartier H, Hu G H. Styrene-assisted Melt Free Radical Grafting of Glycidyl Methacrylate onto Polypropylene[J]. Polym Sci, Part A:Polym Chem, 1998,36:1053-1063. doi: 10.1002/(SICI)1099-0518(199805)36:7<1053::AID-POLA3>3.0.CO;2-3

    21. [21]

      Badrossamay M R, Sun G. A Study on Melt Grafting of N-Halamine Moieties onto Polyethylene and Their Antibacterial Activities[J]. Macromolecules, 2009,42(6):1948-1954. doi: 10.1021/ma802270b

  • 加载中
    1. [1]

      Zhaoxuan ZHULixin WANGXiaoning TANGLong LIYan SHIJiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368

    2. [2]

      Min LIUHuapeng RUANZhongtao FENGXue DONGHaiyan CUIXinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

    3. [3]

      Lirui Shen Kun Liu Ying Yang Dongwan Li Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035

    4. [4]

      Yuan GAOYiming LIUChunhui WANGZhe HANChaoyue FANJie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271

    5. [5]

      Chengqian Mao Yanghan Chen Haotong Bai Junru Huang Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

    6. [6]

      Caixia Lin Ting Liu Zhaojiang Shi Hong Yan Keyin Ye Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107

    7. [7]

      Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018

    8. [8]

      Yanglin Jiang Mingqing Chen Min Liang Yige Yao Yan Zhang Peng Wang Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027

    9. [9]

      Jiajia Li Xiangyu Zhang Zhihan Yuan Zhengyang Qian Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073

    10. [10]

      Zijian Zhao Yanxin Shi Shicheng Li Wenhong Ruan Fang Zhu Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094

    11. [11]

      CCS Chemistry | 超分子活化底物自由基促进高效选择性光催化氧化

      . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.

    12. [12]

      Yikai Wang Xiaolin Jiang Haoming Song Nan Wei Yifan Wang Xinjun Xu Cuihong Li Hao Lu Yahui Liu Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007

    13. [13]

      Zhongyan Cao Shengnan Jin Yuxia Wang Yiyi Chen Xianqiang Kong Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186

    14. [14]

      Danqing Wu Jiajun Liu Tianyu Li Dazhen Xu Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

    15. [15]

      Baitong Wei Jinxin Guo Xigong Liu Rongxiu Zhu Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003

    16. [16]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    17. [17]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

    18. [18]

      Lina Feng Guoyu Jiang Xiaoxia Jian Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171

    19. [19]

      Tao Cao Fang Fang Nianguang Li Yinan Zhang Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098

    20. [20]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

Metrics
  • PDF Downloads(0)
  • Abstract views(503)
  • HTML views(92)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return