不饱和糖功能单体接枝聚氨酯膜的制备及其血液相容性

doi:10.11944/j.issn.1000-0518.2016.04.150259

摘要/Abstract

摘要：

通过葡萄糖、丙烯酸羟乙酯和丁二胺反应,制备了含不饱和双键的糖基功能单体。采用傅里叶红外光谱和核磁共振氢谱对合成的产物进行结构表征确定。采用紫外光引发接枝聚合技术,将制备的不饱和糖单体接枝聚合到聚氨酯膜的表面,以衰减全反射模式下傅里叶红外光谱对表面接枝反应进行了确认。通过静态水接触角实验和血小板黏附实验,分别对改性聚氨酯膜表面的亲水性和血液相容性进行了研究,结果表明,改性聚氨酯膜表面的接触角从86°降低到45°,血小板的粘附量由14.36×10³ cells/mm²减少到2.57×10³ cells/mm²,亲水性明显增强,血液相容性显著改善。

关键词: 糖功能单体, 聚氨酯, 紫外光引发接枝聚合, 血小板粘附

Abstract:

A sugar-based functional monomer containing double bond was synthesized by the reaction of D-glucose, hydroxylethyl acrylate and 1,4-butanediamine. The as-prepared compound was confirmed by Fourier transform infrared spectroscopy(FTIR) and proton nuclear magnetic resonance spectroscopy(¹H NMR). The unsaturated sugar monomer was grafted onto the surface of polyurethane(PU) films by UV-induced grafting polymerization. The surface grafting polymerization was confirmed by FTIR in the attenuated total reflection mode(ATR-FTIR). Water contact angle measurement and platelet adhesion were used to study the hydrophilicity and hemocompatibility of the modified PU films, respectively. It is found that the contact angle of modified PU films decreases from 86° to 45°, and the amount of platelet adhesion is reduced from 14.36×10³ cells/mm² to 2.57×10³ cells/mm². The hydrophilicity of the modified PU films is obviously enhanced and a more hemocompatible interface can be obtained between the film and the biomolecules.

Key words: sugar functional monomer, polyurethane, UV-induced graft polymerization, platelet adhesion

杜山山, 赵春雨, 陈昊, 罗时文, 高萌萌, 辛志荣. 不饱和糖功能单体接枝聚氨酯膜的制备及其血液相容性[J]. 应用化学, 2016, 33(4): 412-418.

DU Shanshan, ZHAO Chunyu, CHEN Hao, LUO Shiwen, GAO Mengmeng, XIN Zhirong. Preparation and Hemocompatibility of Polyurethane Films Grafted with an Unsaturated Sugar-Based Functional Monomer[J]. Chinese Journal of Applied Chemistry, 2016, 33(4): 412-418.

参考文献

[1]	Schreader K J,Bayer I S,Milner D J,et al.A Polyurethane-Based Nanocomposite Biocompatible Bone Adhesive[J]. J Appl Polym Sci,2013,127(6):4974-4982.
[2]	Alves P,Cardoso R,Correia T R,et al.Surface Modification of Polyurethane Films by Plasma and Ultraviolet Light to Improve Haemocompatibility for Artificial Heart Valves[J]. Colloid Surf B,2014,113:25-32.
[3]	Williams D F. On the Mechanisms of Biocompatibility[J]. Biomaterials,2008,29(20):2941-2953.
[4]	Tan D S,Li Z,Yao X L,et al.The Influence of Fluorocarbon Chain and Phosphorylcholine on the Improvement of Hemocompatibility:A Comparative Study in Polyurethanes[J]. J Mater Chem B,2014,2(10):1344-1353.
[5]	Muppalla R,Rana H H,Devi S,et al.Adsorption of Ph-Responsive Amphiphilic Copolymer Micelles and Gel on Membrane Surface as an Approach for Antifouling Coating[J]. Appl Surf Sci,2013,268:355-367.
[6]	SHI Qiang,LUAN Shifang,JIN Jing,et al.Hemocompatibility of Commodity Polymers Modified with Chemical and Biological Method[J]. Mater China,2014,33(4):212-223(in Chinese). 石强,栾世方,金晶,等. 通用高分子材料的化学和生物改性及其血液相容性研究[J]. 中国材料进展,2014,33(4):212-223.
[7]	Zanini S,Riccardi C,Grimoldi E,et al.Plasma-Induced Graft-Polymerization of Polyethylene Glycol Acrylate on Polypropylene Films:Chemical Characterization and Evaluation of the Protein Adsorption[J]. J Colloid Interf Sci,2010,341(1):53-58.
[8]	Xiu K M,Cai Q,Li J S,et al.Anti-Fouling Surfaces by Combined Molecular Self-Assembly and Surface-Initiated Atrp for Micropatterning Active Proteins[J]. Colloid Surf B,2012,90:177-183.
[9]	Deng J P,Wang L F,Liu L Y,et al.Developments and New Applications of Uv-Induced Surface Graft Polymerizations[J]. Prog Polym Sci,2009,34(2):156-193.
[10]	Zhao H Y,Feng Y K,Guo J T. Grafting of Poly(Ethylene Glycol) Monoacrylate onto Polycarbonateurethane Surfaces by Ultraviolet Radiation Grafting Polymerization to Control Hydrophilicity[J]. J Appl Polym Sci,2011,119(6):3717-3727.
[11]	Shan B,Yan H,Shen J,et al.Ozone-Induced Grafting of a Sulfoammonium Zwitterionic Polymer onto Low-Density Polyethylene Film for Improving Hemocompatibility[J]. J Appl Polym Sci,2006,101(6):3697-3703.
[12]	Li W H,Liu P B,Zou H W,et al.Ph Sensitive Microporous Polypropylene Membrane Prepared through Ozone Induced Surface Grafting[J]. Polym Adv Technol,2009,20(3):251-257.
[13]	Zhao J,Shi Q A,Yin L G,et al.Polypropylene Modified with 2-Hydroxyethyl Acrylate-G-2-Methacryloyloxyethyl Phosphorycholine and Its Hemocompatibility[J]. Appl Surf Sci,2010,256(23):7071-7076.
[14]	Deng J P,Yang T W,Ranby B. Surface Photografting Polymerization of Vinyl Acetate(Vac), Maleic Anhydride, and Their Chargee Transfer Complex. Vac(2)[J]. J Appl Polym Sci,2000,77(7):1522-1531.
[15]	Sugiura S,Edahiro J I,Sumaru K,et al.Surface Modification of Polydimethylsiloxane with Photo-Grafted Poly(Ethylene Glycol) for Micropatterned Protein Adsorption and Cell Adhesion[J]. Colloid Surf B,2008,63(2):301-305.
[16]	Li X M,Luan S F,Yang H W,et al.Surface Modification of Poly(Styrene-B-(Ethylene-Co-Butylene)-B-Styrene) Elastomer via Photo-Initiated Graft Polymerization of Poly(Ethylene Glycol)[J]. Appl Surf Sci,2012,258(7):2344-2349.
[17]	Luan S F,Zhao J,Yang H W,et al.Surface Modification of Poly(Styrene-B-(Ethylene-Co-Butylene)-B-Styrene) Elastomer via Uv-Induced Graft Polymerization of N-Vinyl Pyrrolidone[J]. Colloid Surf B,2012,93:127-134.
[18]	Xin Z R,Du B B,Yan S J,et al.Surface Modification of Polyurethane via Covalent Immobilization of Sugar-Based Trisiloxane Surfactants[J]. Des Monomers Polym,2015,18(3):284-294.
[19]	Xin Z R,Yan S J,Du B B,et al.On Properties of Graft Copolymers of Lldpe and Novel Fluorine Surfactants Obtained via Reactive Extrusion[J]. Des Monomers Polym,2014,17(8):746-752.
[20]	Cen L,Neoh K G,Kang E T. Surface Functionalization of Electrically Conductive Polypyrrole Film with Hyaluronic Acid[J]. Langmuir,2002,18(22):8633-8640.
[21]	Li X M,Luan S F,Shi H C,et al.Improved Biocompatibility of Poly(Styrene-B-(Ethylene-Co-Butylene)-B-Styrene) Elastomer by a Surface Graft Polymerization of Hyaluronic Acid[J]. Colloid Surf B,2013,102:210-217.
[22]	Zhao J,Shi Q A,Luan S F,et al.Improved Biocompatibility and Antifouling Property of Polypropylene Non-Woven Fabric Membrane by Surface Grafting Zwitterionic Polymer[J]. J Membr Sci,2011,369(1/2):5-12.
[23]	Song L J,Zhao J,Luan S F,et al.Fabrication of a Detection Platform with Boronic-Acid-Containing Zwitterionic Polymer Brush[J]. ACS Appl Mater Interfaces,2013,5(24):13207-13215.
[24]	Yang Q,Xu ZK,Dai ZW,et al.Surface Modification of Polypropylene Microporous Membranes with a Novel Glycopolymer[J]. Chem Mater,2005,17(11):3050-3058.
[25]	Bordegé V,Muñoz-Bonilla A,León O,et al.Glycopolymers with Glucosamine Pendant Groups Copolymeri Ation,Physico-Chemical and Interaction Properties[J]. React Funct Polym,2011,71:1-10.
[26]	Cerrada M L,Bordege V,Munoz-Bonilla A,et al.Amphiphilic Polymers Bearing Gluconolactone Moieties:Synthesis and Long Side-Chain Crystalline Behavior[J]. Carbohydr Polym,2013,94(2):755-764.
[27]	Choi H S,Kim Y S,Zhang Y,et al.Plasma-Induced Graft Co-Polymerization of Acrylic Acid onto the Polyurethane Surface[J]. Surf Coat Technol,2004,182(1):55-64.
[28]	Brass L F. Thrombin and Platelet Activation[J]. Chest,2003,124(3):18s-25s.
[29]	Skoglund C,Wettero J,Skogh T,et al.C-Reactive Protein and C1q Regulate Platelet Adhesion and Activation on Adsorbed Immunoglobulin G and Albumin[J]. Immunol Cell Biol,2008,86(5):466-474.