Melt Functionalization of Polyethylene Initiated by N-Hydroxyphthalimide

doi:10.11944/j.issn.1000-0518.2020.05.190361

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (5): 518-523.DOI: 10.11944/j.issn.1000-0518.2020.05.190361

• Full Papers • Previous Articles Next Articles

Melt Functionalization of Polyethylene Initiated by N-Hydroxyphthalimide

WEN Liang^a,YANG Huawei^b^*(),SHI Hengchong^b,LUAN Shifang^b,YIN Jinghua^b,SHI Dean^a^*()

^aHubei Provincial Key Laboratory of Polymer,Materials School of Materials Science and Engineering,Hubei University,Wuhan 430062,China
^bState Key Laboratory of Polymer Physics and Chemistry,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China

Received:2019-12-30 Accepted:2020-03-24 Published:2020-05-01 Online:2020-04-29
Contact: YANG Huawei,SHI Dean
Supported by:
Supported by the National Natural Science Foundation of China(No.51803213, No.51973052)

Abstract

Abstract:

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.

Key words: N-hydroxyphthalimide, melt free radical grafting, polyethylene

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.

References

[1]	JI Fance,LIU Xiangdong,YANG Yuming, et al. Photothermal-Induced Shape Memory Polymers Prepared by Reactive Blending[J]. Chinese J Appl Chem,2019,36(8):904-908(in Chinese). 纪凡策,刘向东,杨宇明,等. 反应共混制备光触发形状记忆聚合物材料[J]. 应用化学,2019,36(8):904-908.
[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(in Chinese). 李沛,张嘉琪,陈全,等. 4种低密度聚乙烯树脂的链结构及其性能[J]. 应用化学,2019,36(11):1237-1247.
[3]	Al-Malaika S. Reactive Modifiers for Polymers[M]. Springer Netherlands,1997:84-132.
[4]	Moad G. The Synthesis of Polyolefin Graft Copolymers by Reactive Extrusion[J]. Prog Polym Sci,1999,24(1):81-142.
[5]	Russell K E. Free Radical Graft Polymerization and Copolymerization at Higher Temperatures[J]. Prog Polym Sci,2002,27(6):1007-1038.
[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(in Chinese). 施德安,殷敬华,柯卓. 聚丙烯熔融接枝马来酸酐反应机理的研究[J]. 应用化学,2001,18(11):865-868.
[7]	Shi D,Yang J H,Yao Z H, et al. Functionalization of Iisotactic Polypropylene with Maleic Anhydride by Reactive Extrusion:Mechanism of Melt Grafting[J]. Polymer,2001,42(13):5549-5557.
[8]	Denis B, Philippe C, Jean-Jacques F, et al. 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.
[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(in Chinese). 蔡传伦,辛志荣,姚占海,等. 预辐射聚丙烯反应挤出接枝丙烯酸的研究[J]. 高等学校化学学报,2006,27(10):1969-1973.
[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.
[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.
[12]	Zhang C,Huang Z,Lu J, et al. Generation and Confinement of Long-lived N-Oxyl Radical and Its Photocatalysis[J]. J Am Chem Soc,2018,140(6):2032-2035.
[13]	Hara T,Iwahama T,Sakaguchi S, et al. 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.
[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]	Opeida I A,Kompanets M A,Kushch O V, et al. N-Hydroxyphthalimide-Initiated Radical Polymerization of Vinyl Monomers[J]. Russ J Appl Chem,2007,80(10):1717-1720.
[16]	Chen K,Xie H,Mao J, et al. Structure-Performance Landscape of N-Alkoxyphthalimides as Organocatalysts in Aerobic Oxidation[J]. J Catal,2016,344:229-235.
[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.
[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]	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.
[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.
[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.

Melt Functionalization of Polyethylene Initiated by N-Hydroxyphthalimide

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	He-Chang SHI, Yan-Cun YU, Chang-Yu HAN. Morphology， Rheological and Mechanical Properties of Polyethylene/Aluminium Oxide Composites [J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1593-1599.
[2]	LI Yi, CHENG Hong-Da, YU Yan-Cun, HAN Chang-Yu, CHEN Guang-Jian, ZHU Ying-Nan. Performance of Thermal Conductive High Density Polyethylene Composite [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 954-960.
[3]	LU Ling-Pan, WU Jia-Jun, WANG Kai-Ti. Preparation of Long-Chain Branched Polyethylene Catalyzed by Tandem Catalytic System [J]. Chinese Journal of Applied Chemistry, 2021, 38(1): 69-76.
[4]	DUAN Jinchi, QI Yunxia, SHI Chengying, ZHAO Qi, LIU Baijun, SUN Zhaoyan, XU Yiquan, HU Wei, ZHANG Niaona. Electron Beam Radiation Modification of Polyethylene Thermal Conductive Composites [J]. Chinese Journal of Applied Chemistry, 2020, 37(8): 896-903.
[5]	HE Yufang, YAN Pinping, HUANG Baoquan, LUO Fubin, LI Hongzhou, QIAN Qingrong, CHEN Qinghua. Thermal Conductivity and Crystallization Behavior of Polyethylene Glycol/Boron Nitride Phase Change Composites [J]. Chinese Journal of Applied Chemistry, 2020, 37(6): 650-657.
[6]	QI Yanxin, HUANG Yubin, JIN Ningyi. Preparation and Release Behavior of Progesterone Nano Micelles in Vitro [J]. Chinese Journal of Applied Chemistry, 2020, 37(11): 1340-1342.
[7]	AN Pinping, LUO Fubin, HUANG Baoquan, XIAO Liren, QIAN Qingrong, LI Hongzhou, CHEN Qinghua. Properties of Thermal Conductivity Enhanced Polyethylene Glycol-Based Phase Change Composites [J]. Chinese Journal of Applied Chemistry, 2020, 37(1): 46-53.
[8]	LI Pei,ZHANG Jiaqi,LIU Wei,CHEN Quan,TANG Yujing,JI Xiangling,XUE Yanhu,SUN Guangping. Chain Structure and Properties of Four Commercial Low Density Polyethylene Resins [J]. Chinese Journal of Applied Chemistry, 2019, 36(11): 1237-1247.
[9]	LÜ Wenqiang,GENG Chao,XU Jingwei. Synthesis of Polyethylene Glycol Aldehyde Derivatives by Ozonation [J]. Chinese Journal of Applied Chemistry, 2019, 36(1): 120-122.
[10]	LI Fei,MAO Shengxue,SUN Yue,LÜ Chengwei,AN Yue. Dipotassium Hydrogenphosphate Assisted Multi-component One-Pot Synthesis of 1,4-Hihydropyrano[2,3-c]pyrazole Derivatives [J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1201-1207.
[11]	HUANG Dengfa,LIU Yanhua,WANG Feng. Partial Factorial Analysis for the Stability of Water-in-Oil Type Polyethyleneimine Solution-in-Paraffin Emulsion [J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1234-1242.
[12]	SHI Yanlong, WANG Zhidan, FANG Yun, LYU Tao, FENG Xiaojuan, FENG Lei, YANG Wu. Fabrication of Superhydrophobic-Superoleophilic Copper Mesh and Its Application in Oil-Water Separation [J]. Chinese Journal of Applied Chemistry, 2017, 34(4): 472-480.
[13]	BI Bo, KAI Wang, REN Liping, QIAN Hua. Thermoregulated Biphasic Acidic Polymeric Ionic Liquid Catalyzed Amine Aldehyde Condensation Reaction [J]. Chinese Journal of Applied Chemistry, 2017, 34(4): 394-401.
[14]	BI Bo, KAI Wang, REN Liping, QIAN Hua. Thermoregulated Biphasic Acidic Polymeric Ionic Liquid Catalyzed Amine Aldehyde Condensation Reaction [J]. Chinese Journal of Applied Chemistry, 2017, 34(4): 0-0.
[15]	ZHANG Guangchun, QIU Jian, XING Haiping, TANG Tao. Influence of Polyethylene-g-polystyrene on the Mechanical Properties and Foaming Behavior of Linear Low Density Polyethylene/Polystyrene Blends [J]. Chinese Journal of Applied Chemistry, 2016, 33(7): 756-765.