Metal-mediated Activators Generated by Electron Transfer for Atom Transfer Radical Polymerization of Methyl Methacrylate with Basic Ionic Liquids as the Catalyst

doi:10.3724/SP.J.1095.2014.30372

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Metal-mediated Activators Generated by Electron Transfer for Atom Transfer Radical Polymerization of Methyl Methacrylate with Basic Ionic Liquids as the Catalyst

CHEN Min, DENG Zhijun^*, ZHANG Liben, LI Xiaogang

(Jiangsu Dewei Advanced Materials Co.,Led,Taicang 215421,China)

Received:2013-07-22 Revised:2013-09-10 Published:2014-05-10 Online:2014-05-10

Abstract

Abstract: Basic ionic liquids(BILs), including 1-butyl-3-methyl imidazolium hydroxide([Bmim][OH]), coordinated with iron chloride, copper chloride, and ruthenium trichloride, were used as both the ligand and catalyst in activators generated by electron transfer for atom transfer radical polymerization(AGET ATRP) of methyl methacrylate(MMA) in bulk and solution, using ethyl 2-bromoisobutyrate(EBiB) as the initiator, vitamin C(VC) as the reducing agent. Catalytic amount of BILs can enhance the polymerization rate, and produce PMMA with controllable relative molecular mass and narrow relative molecular mass distribution(Mw/Mn=1.20~1.50). The influence of the addition of BILs on the polymerization rate and relative molecular mass distributions were investigated. The catalytic properties of the three catalytic systems were studied by cyclic voltammetry(CV) characterization. The nature of controlled/“living” free radical polymerization in the presence of BILs was confirmed by chain-extension experiments. The ready solubility of BILs enables them to be applied as a new type of catalyst in AGET ATRP.

Key words: activators generated by electron transfer, atom transfer radical polymerization, basic ionic liquid-metal salts, cyclic voltammetry, catalyst,polymethylmethacrylate, chain extension

CLC Number:

O622.1

CHEN Min, DENG Zhijun*, ZHANG Liben, LI Xiaogang . Metal-mediated Activators Generated by Electron Transfer for Atom Transfer Radical Polymerization of Methyl Methacrylate with Basic Ionic Liquids as the Catalyst[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30372.

References

[1] Wang J S,Matyjaszewski K. Controlled/“Living” Radical Polymerization. Atom Transfer Radical Polymerization in the Presence of Transition-metal Complexes[J]. J Am Chem Soc,1995,117:5614-5615.

[2] Kato M,Kamigaito M,Sawamoto M,et al. Polymerization of Methyl Methacrylate with the Carbon Tetrachloride/Dichlorotris-(triphenylphosphine)ruthenium(Ⅱ)/Methylaluminum Bis(2,6-di-tert-butylphenoxide) Initiating System:Possibility of Living Radical Polymerization[J]. Macromolecules,1995,28:1721-1723.

[3] Machado M,Faucher S,Zhu S P. Hybrid Atom Transfer Radical Polymerization System for Balanced Polymerization Rate and Polymer Molecular Weight Control[J]. J Polym Sci Part A,2010,48:2294-2301.

[4] Liu C H,Pan C Y. A Novel Strategy for Enhancing Propagation Rate of Polystyrene Grown from Silica Nanoparticles or Carbon Nanotubes[J]. Polym Chem,2011,2:563-566.

[5] Min K,Gao H F,Matyjaszewski K. Preparation of Homopolymers and Block Copolymers in Miniemulsion by ATRP Using Activators Generated by Electron Transfer(AGET)[J]. J Am Chem Soc,2005,127:3825-3830.

[6] Oh J K,Dong H C,Zhang R,et al. Preparation of Nanoparticles of Double-hydrophilic PEO-PHEMA Block Copolymers by AGET ATRP in Inverse Miniemulsion[J]. J Polym Sci Part A,2007,45:4764-4772.

[7] Kitayama Y,Kagawa Y,Minami H,et al. Preparation of Micrometer-Sized, Onionlike Multilayered Block Copolymer Particles by Two-Step AGET ATRP in Aqueous Dispersed Systems:Effect of the Second-Step Polymerization Temperature[J]. Langmuir,2010,26:7029-7034.

[8] Deng Z,Qiu L,Bai L,et al. Basic Ionic Liquid/FeCl3[DK1]·6H2O as an Efficient Catalyst for AGET ATRP of Methyl Methacrylate[J]. J Polym Sci Part A,2012,50:1605-1610.

[9] Jakubowski W,Matyjaszewski K. Activator Generated by Electron Transfer for Atom Transfer Radical Polymerization[J]. Macromolecules,2005,38:4139-4146.

[10] Xia J,Zhang X,Matyjaszewski K. The Effect of Ligands on Copper-Mediated Atom Transfer Radical Polymerization[J]. ACS Symp Ser,2000,760:207-223.

[11] Ando T,Kamigaito M,Sawamoto M. Iron(Ⅱ)-Chloride Complex for Living Radical Polymerization of Methyl Methacrylate[J]. Macromolecules,1997,30:4507-4510.

[12] Zhu S,Yan D. Atom Transfer Radical Polymerization of Methyl Methacrylate Catalyzed by Iron(Ⅱ) Chloride/Isophthalic Acid System[J]. Macromolecules,2000,33:8233-8288.

[13] Wang G,Zhu X L,Cheng Z P,et al. Reverse Atom Transfer Radical Polymerization of Methyl Methacrylate with FeCl3/Pyromellitic Acid[J]. Eur Polym J,2003,39:2161-2165.

[14] Zhu S M,Yan D Y. New Ligands for Atom-transfer Radical Polymerization[J]. Macromol Rapid Commun,2000,21:1209-1213.

[15] Zhu S,Yan D,Zhang G,et al. Controlled/“Living” Radical Polymerization of Styrene Catalyzed by FeCl2/Succinic Acid[J]. Macromol Chem Phys,2000,201:2666-2669.

[16] Kotani Y,Kamigaito M,Sawamoto M. FeCp(CO)2I:A Phosphine-Free Half-Metallocene-Type Iron(Ⅱ) Catalyst for Living Radical Polymerization of Styrene[J]. Macromolecules,1999,32:6877-6880.

[17] Niibayashi S,Hayakawa H,Jin R H,et al. Reusable and Environmentally Friendly Ionic Trinuclear Iron Complex Catalyst for Atom Transfer Radical Polymerization[J]. Chem Commun,2007:1855-1857.

[18] Matyjaszewski K,Coca S,Gaynor S G,et al. Zerovalent Metals in Controlled/“Living” Radical Polymerization[J]. Macromolecules,1997,30:7348-7350.

[19] Xue Z G,Linh N T B,Noh S K,et al. Phosphorus-Containing Ligands for Iron(Ⅲ)-Catalyzed Atom Transfer Radical Polymerization[J]. Angew Chem Int Ed,2008,47:6426-6429.

[20] Wang Y,Matyjaszewski K. ATRP of MMA in Polar Solvents Catalyzed by FeBr2 without Additional Ligand[J]. Macromolecules,2010,43:4003-4005.

[21] Wang W,Zhang Z,Wu Y,et al. Ligand-free Cu(0)-Mediated Controlled Radical Polymerization of Methyl Methacrylate at Ambient Temperature[J]. J Polym Sci Part A,2012,50:711-719.

[22] Bai L,Zhang L,Zhang Z,et al. Iron-Mediated AGET ATRP of Styrene in the Presence of Catalytic Amounts of Base[J]. Macromolecules,2010,43:9283-9290.

[23] Bai L,Zhang L,Zhang Z,et al. Alumina Additives for Fast Iron-mediated AGET ATRP of MMA Using Onium Salt as Ligand[J]. J Polym Sci Part A,2011,49:3970-3979.

[24] Deng Z,Guo J,Qiu L,et al. Basic ionic Liquids:A New Type of Ligand and Catalyst for the AGET ATRP of Methyl Methacrylate[J]. Polym Chem,2012,3:2436-2443.

[25] Ando T,Kamigaito M,Sawamoto M. Catalytic Activities of Ruthenium(Ⅱ) Complexes in Transition-Metal-Mediated Living Radical Polymerization:Polymerization, Model Reaction, and Cyclic Voltammetry[J]. Macromolecules,2000,33:5825-5829.

[26] Qiu J,Matyjaszewski K,Thouin L,et al. Cyclic Voltammetric Studies of Copper Complexes Catalyzing Atom Transfer Radical Polymerization[J]. Macromol Chem Phys,2000,201:1625-1631.

Metal-mediated Activators Generated by Electron Transfer for Atom Transfer Radical Polymerization of Methyl Methacrylate with Basic Ionic Liquids as the Catalyst

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shi-Peng JIANG, Yu-Xi ZHOU, Pei-Ran MENG, Yan-Xuan XIE, Zhi-Yi SONG, Huan-Ying ZHAO, Yue SUN. Preparation and Properties of Ultramicro Imprinting Sensor for Human Serum Albumin via Metal-free Visible-light-induced Atom Transfer Radical Polymerization [J]. Chinese Journal of Applied Chemistry, 2023, 40(2): 299-308.
[2]	WANG Wei, LI Juan, BAI Ru, HAN Zhen, FENG Xuewei, SUN Yue. Preparation of Au/Polyacrylamide@Graphene Oxide/Nano-palladium Electrode via Metal-Free Visible-Light-Induced Atom Transfer Radical Polymerization and Its Detection of Ethanol [J]. Chinese Journal of Applied Chemistry, 2020, 37(5): 595-603.
[3]	LIU Yutong,ZHAO Mengyuan,LI Siyu,YANG Yifei,SUN Yue. Preparation of Molecularly Imprinted Polymers by Superoxide Dismutase-Catalyzed Electrochemically-Mediated Atom Transfer Radical Polymerization [J]. Chinese Journal of Applied Chemistry, 2019, 36(5): 585-594.
[4]	YANG Muquan, XIAO Lingyu, ZHANG Xuan, YAN Yue. Fabrication of Poly(4-Vinylpyridine-b-Polyethylene Glycol) Diblock Copolymer Brushes from Au Surfaces and Their pH Responsive Behavior [J]. Chinese Journal of Applied Chemistry, 2019, 36(4): 431-439.
[5]	HUANG Xuehong, LIN Juan, ZHENG Ronxue, LIN Yifeng, DING Fuchuan, LING Qidan. Synthesis of Side-chain-sulfonated Poly(ether ether ketone) as Cation Exchange Membranes by Atom Transfer Radical Polymerization [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 878-884.
[6]	ZHU Chang'an, WU Feiyu, WANG Xue, GAO Li′na, WENG Qianfeng, SHI Li, ZHANG Chenglu*. Synthesis, Biological Activity and Electrochemical Properties of Ferrocenyl 1,3,4-Triazoles Derivatives [J]. Chinese Journal of Applied Chemistry, 2014, 31(04): 455-461.
[7]	LIU Wenhan*, YUAN Ronghui, TENG Yuanjie, MA Chunan. Electrochemical Oxidation Mechanism of Thiosalicylic Acid on Activated Glassy Carbon Electrode [J]. Chinese Journal of Applied Chemistry, 2014, 31(03): 342-347.
[8]	WANG Jianhui, GUO Liqin, RUAN Wenjuan*, ZHU Zhiang. Synthesis and Electrochemical Properties of Salen-type Copper(Ⅱ) and Nickel(Ⅱ) Complexes [J]. Chinese Journal of Applied Chemistry, 2014, 31(03): 303-309.
[9]	GAO Wei, LIU Ruiquan*, MI Hongyu. Electrodeposition Behaviors of Copper in Ionic Liquid [J]. Chinese Journal of Applied Chemistry, 2014, 31(02): 212-219.
[10]	DING Wei*, WANG Ling, YU Tao, QU Guangmiao, GAO Xiang, LI Ming. Atom Transfer Radical Copolymerization of Acrylamide Under Microwave Irradiation [J]. Chinese Journal of Applied Chemistry, 2013, 30(04): 398-402.
[11]	HOU Hongying1,2, LIU Xianxi3, Philippe Knauth2. Electrooxidation Behaviors of Sulfonated 4,4'-Biphenyl Diphenol [J]. Chinese Journal of Applied Chemistry, 2013, 30(04): 444-447.
[12]	CHEN Huan, MA Wei, SUN Dengming*. Simultaneous Determination of Hydroquinone and Catechol at the Silver Doped Poly(L-methionine) Modified Glassy Carbon Electrode [J]. Chinese Journal of Applied Chemistry, 2012, 29(05): 576-584.
[13]	LIU Caisheng1, QIAO Haiyan2, GU Ningyu1, TANG Jilin2. Determination of Hydrogen Peroxide Using 4-(2-Pyridylazo)-Resorcinol Polymer Film Modified Glassy Carbon Electrode [J]. Chinese Journal of Applied Chemistry, 2012, 29(02): 216-221.
[14]	YANG Weiwei, GAO Xiang*. Substituent Effect on NMR and Reduction Potentials of 1,2-H(XPhCH2)C60 Derivatives [J]. Chinese Journal of Applied Chemistry, 2011, 28(09): 1041-1045.
[15]	ZHONG Yu, SHEN Jun, WEI Rongqing, LIU Xiaoning*. Removal of Cu-ion in block copolymer of PMMA-PLLA-PMMA prepared via ATRP by washing-extraction method [J]. Chinese Journal of Applied Chemistry, 2011, 28(03): 254-257.