光降解聚合物研究进展
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摘要
介绍了共聚型光降解聚合物和添加型光降解聚合物两大类光降解聚合物以Norrish反应为主的光降解反应机理,以及综述了光降解聚合物的国内外发展状况,并对各类光降解聚合物的优缺点进行了分析总结。其次,提出了光降解聚合物在生产发展过程中存在的问题以及如何解决这些问题的途径。最后,展望了光降解聚合物的未来发展前景。
This paper introduced the photodegradation mechanisms of copolymerization-type and additive-type photodegradable polymers based on Norrish reaction, overviewed the development of photodegradable polymers in China and overseas, and also analyzed the advantages and disadvantages of various photodegradable polymers. Furthermore, the problems in the development of photodegradable polymers and the relevant resolution were proposed. Finally, the future development prospects of photodegradable polymers were discussed.
This paper introduced the photodegradation mechanisms of copolymerization-type and additive-type photodegradable polymers based on Norrish reaction, overviewed the development of photodegradable polymers in China and overseas, and also analyzed the advantages and disadvantages of various photodegradable polymers. Furthermore, the problems in the development of photodegradable polymers and the relevant resolution were proposed. Finally, the future development prospects of photodegradable polymers were discussed.
引文
[1] 陈光.新材料概论[M].北京:国防工业出版社,2013:219-226.
[2] SHARABI D,PAZ Y.Preferential Photodegradation of Contaminants by Molecular Imprinting on Titanium Dio-xide[J].Applied Catalysis B:Environmental,2010,95(1):169-178.
[3] YOUSIF E,HADDAD R .Photodegradation and Photostabilization of Polymers,Especially Polystyrene:Review[J].Springerplus,2013,2(1):398.
[4] 陈昌乾.紫外辐照引发的反应挤出过程制备长链支化聚乳酸及其性能研究[D].广州:华南理工大学,2016.
[5] SHEMES H,DORI T,LAN Z,et al.Dynamics of Triplet-State Photochemistry of Pentanal:Mechanisms of Norrish I,Norrish II,and H Abstraction Reactions[J].Journal of Physical Chemistry A,2013,117(46):11-24.
[6] S?LLING T I,DIAU E W,K?TTING C,et al.Femtochemistry of Norrish Type-I Reactions:IV.Highly Excited Ketones—Experimental[J].Chemphyschem,2010,3(1):79-97.
[7] MAI Y W,COTTERELL B.Oxidative and Nonoxidative Photodegradation of Nylon 6[J].Journal of Applied Polymer Science,2010,27(12):4 885-4 887.
[8] YANO S,MURAYAMA M.Effect of Photodegradation on Dynamic Mechanical Properties of Nylon 6[J].Journal of Applied Polymer Science,2010,25(3):433-447.
[9] CHRISTENSEN P A,EGERTON T A,MARTINS-FRANCHETTI S M,et al.Photodegradation of Polycaprolactone/Poly(vinyl chloride) Blend[J].Polymer Degradation & Stability,2008,93(1):305-309.
[10] NAKAMURA H,NAKAMURA T,NOGUCHI T,et al.Photodegradation of PEEK Sheets Under Tensile Stress[J].Polymer Degradation & Stability,2006,91(4):740-746.
[11] NAKAMURA T,OGUMA H,SASAKI N,et al.J191021 Strength Degradation Mechanisms of UV-irradiated PEEK Films[C]//Mechanical Engineering Congress,Japan:The Japan Society of Mechanical Engineers,2011.
[12] 高炜斌,韩世民,杨明娇,等.光氧老化对聚碳酸酯结构和性能的影响[J].高分子材料科学与工程,2008,24(10):67-70.GAO W B,HAN S M,YANG M J,et al.Effect of Photooxidative Aging on the Structure and Properties of Polycarbonate[J].Polymer Materials Science and Engineering,2008,24(10):67-70.
[13] 龚跃法,郑炎松,陈东红,等.有机化学[M].武汉:华中科技大学出版社,2012:188-209.
[14] PICKETT,JAMES E.Influence of Photo-Fries Reaction Products on the Photodegradation of Bisphenol-A Polycarbonate[J].Polymer Degradation & Stability,2011,96(12):2 253-2 265.
[15] MEHR M Y,DRIEL W D V,JANSEN K M B,et al.Photodegradation of Bisphenol A Polycarbonate Under Blue Light Radiation and Its Effect on Optical Properties[J].Optical Materials,2013,35(3):504-508.
[16] 周从恒,黄彦红,李丹,等.食品级聚碳酸酯的光氧老化性能[J].合成树脂及塑料,2017,34(4):6-8.ZHOU C H,HUANG Y H,LI D,et al.Photooxidative Aging Properties of Food Grade Polycarbonates[J].Synthetic Resins and Plastics,2017,34(4):6-8.
[17] OSAWA Z,KOBAYASHI S,SAITO T,et al.Comparative Study on the Degradation Behavior of Ethylene-carbon Monoxide Copolymers under Natural Environment in Japan and China[J].Journal of Materials Life Society,2011(6):134-145.
[18] ABANTO-BUENO J,LAMBROS J.Mechanical and Fracture Behavior of an Artificially Ultraviolet-irradiated Poly(ethylene-carbon monoxide) Copolymer[J].Journal of Applied Polymer Science,2010,92(1):139-148.
[19] SANGEN O,YAMAMOTO Y,IMAMURA R.Photodegradation of Polyether-Polyester Block Copolymers[J].Sen-ito Kogyo,2008,29(11):472-481.
[20] CHEN T,ZHANG J,YOU H.Photodegradation Behavior and Mechanism of Poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate) (PETG) Random Copolymers:Correlation with Copolymer Composition[J].Rsc Advances,2016,6(104):102 778-102 790.
[21] Manfred Schwab.Photosensitizer[M]//Encyclopedia of Cancer,Berlin Heidelberg:Springer Berlin Heidelberg,2011:2 881-2 882.
[22] 李晓龙,刘斌.光敏剂研究进展[J].中国激光医学杂志,2015(6):327-333.LI X L,LIU B.Progress in Photosensitizers[J].Chinese Journal of Laser Medicine,2015(6):327-333.
[23] 宁培森,王克昌,丁著明.二苯甲酮类紫外线吸收剂的发展趋势[J].塑料助剂,2008(2):7-12.NING P S,WANG K C,DING Z M.Development Trend of Benzophenone UV Absorbers[J].Plastics Additives,2008(2):7-12.
[24] RIYAJAN S A,SAKDAPIPANICH J T,TANAKA Y.Controlled Degradation of Cured Natural Rubber by Encapsulated Benzophenone as a Photosensitizer[J].Journal of Applied Polymer Science,2010,90(1):297-305.
[25] HOSONO K,KANAZAWA A,MORI H,et al.Photodegradation of Cellulose Acetate Film in the Presence of Benzophenone as a Photosensitizer[J].Journal of Applied Polymer Science,2010,105(6):3 235-3 239.
[26] EZEANI O E,IGWE I O,ONYEAGORO G N.The Effect of Benzophenone Photo-Initiator on Some Mechanical Properties of Photo-Oxidized Polypropylene/Thermoplastic Starch Blends[J].The International Journal of Engineering and Science,2017,6(1):43-51.
[27] 舒伟.光降解塑料的降解原理及其应用[J].印刷质量与标准化,2011(5):8-11.SHU W.Degradation Principle and Application of Photodegradable Plastics[J].Printing Quality and Standardization,2011(5):8-11
[28] 贾芳.低密度聚乙烯的光降解特性的研究[D].广州:广东工业大学,2008.
[29] SUáREZ-QUEZADA M,ROMERO-ORTIZ G,SUáREZ V,et al.Photodegradation of phenol using reconstructed Ce doped Zn/Al layered double hydroxides as photocatalysts[J].Catalysis Today,2016(271):213-219.
[30] 王怀庚.多组份聚乙烯降解薄膜的制备及其结构、性能的研究[D].苏州:苏州大学,2013.
[31] 李海龙,管明章,程凤梅.光敏剂对mLLDPE薄膜光氧化降解性能的影响[J].塑料科技,2011,39(5):88-91.LI H L,GUAN M Z,CHENG F M.Effects of Photosensitizers on Photooxidative Degradation of mLLDPE Films[J].Plastics Science,2011,39(5):88-91.
[32] LI H,LI H,CHENG F.Radiation Crosslinking of m-LLDPE Film with Different Photosensitizer[J].Polymer Materials Science & Engineering,2012,28(5):89-91,95.
[33] TAY T,DAS S,STEWART P.Magnesium Stearate Increases Salbutamol Sulphate Dispersion:What Is the Mechanism?[J].International Journal of Pharmaceutics,2009,383(1):62-69.
[34] OSAWA Z,KURISU N,NAGASHIMA K,et al.The Effect of Transition Metal Stearates on the Photodegradation of Polyethylene[J].Journal of Applied Polymer Science,2010,23(12):3 583-3 590.
[35] 杨根玲.稀土有机化合物催化LDPE光降解研究[J].广东化工,2013,40(13):41-42.YANG G L.Study on Photodegradation of LDPE Catalyzed by Rare Earth Organic Compounds[J].Guangdong Chemical Industry,2013,40(13):41-42.
[36] 谢孝勋,彭汉.可控光降解聚乙烯薄膜的研究[J].合成材料老化与应用,2009,6(1):1-4.XIE X X,PENG H.Study on Controllable Photodegradation of Polyethylene Films[J].Aging and Application of Synthetic Materials,2009,6(1):1-4.
[37] 梁力丽,罗学刚.光敏剂对聚乙烯地膜力学性能的影响[J].中国塑料,2008,22(7):88-91.LIANG L L,LUO X G.Effect of Photosensitizer on Mechanical Properties of Polyethylene Film[J].China Plastics,2008,22(7):88-91.
[38] 黄旭方,肖荔人,刘欣萍,等.几种光敏剂对聚乙烯光敏化效果的对比研究[J].福建师范大学学报(自然科学版),2011,27(2):70-75.HUANG X F,XIAO L R,LIU X P,et al.Comparative Study on Photosensitization Effect of Several Photosensitizers on Polyethylene[J].Journal of Fujian Normal University (Natural Science Edition),2011,27(2):70-75.
[39] LIN Y.Study of Ultraviolet Photooxidative Degradation of LDPE Film Containing Cerium Carboxylate Photosensitizer[J].Journal of Applied Polymer Science,2015,63(6):811-818.
[40] 孙琼.二氧化钛光催化、光敏化影响因素及机理研究[D].杭州:浙江大学,2011.
[41] DEVEAU P A,ARSAC F,THIVEL P X,et al.Different Methods in TiO2,Photodegradation Mechanism Studies:Gaseous and TiO2 -Adsorbed Phases[J].Journal of Hazardous Materials,2007,144(3):692-697.
[42] SHAWAPHUN S,MANANGAN T,WACHARAWICHA-NANT S.Thermo-and Photo-Degradation of LDPE and PP Films Using Metal Oxides as Catalysts[J].Advanced Materials Research,2010(93/94):505-508.
[43] YANG R,CHRISTENSEN P A,EGERTON T A,et al.Degradation Products Formed During UV Exposure of Polyethylene-ZnO Nano-composites[J].Polymer Degradation & Stability,2010,95(9):1 533-1 541.
[44] ELTAYEB E,BARIKANI M,MAHDAVIAN A,et al.An Investigation into the UV-Photo-Oxidative Degradation of LDPE by Using Cobalt Naphthenate as Photosensitizer[J].Journal of Macromolecular Science:Part D—Reviews in Polymer Processing,2010,49(7):718-724.
[45] YANG C,YE L,TIAN L,et al.Photodegradation Activity of Polyvinyl Chloride (PVC)-Perchlorinated Iron (II) Phthalocyanine (FePcCl16) Composite Film[J].Journal of Colloid & Interface Science,2011,353(2):537-541.
[46] 颜百愉,张安,彭伟鑫,等.回收塑料的光降解改性研究进展[J].广州化工,2017,45(13):14-15.YAN B Y,ZHANG A,PENG W X,et al.Research Progress on Photodegradation Modification of Recycled Plastics[J].Guangzhou Chemical,2017,45(13):14-15.
[2] SHARABI D,PAZ Y.Preferential Photodegradation of Contaminants by Molecular Imprinting on Titanium Dio-xide[J].Applied Catalysis B:Environmental,2010,95(1):169-178.
[3] YOUSIF E,HADDAD R .Photodegradation and Photostabilization of Polymers,Especially Polystyrene:Review[J].Springerplus,2013,2(1):398.
[4] 陈昌乾.紫外辐照引发的反应挤出过程制备长链支化聚乳酸及其性能研究[D].广州:华南理工大学,2016.
[5] SHEMES H,DORI T,LAN Z,et al.Dynamics of Triplet-State Photochemistry of Pentanal:Mechanisms of Norrish I,Norrish II,and H Abstraction Reactions[J].Journal of Physical Chemistry A,2013,117(46):11-24.
[6] S?LLING T I,DIAU E W,K?TTING C,et al.Femtochemistry of Norrish Type-I Reactions:IV.Highly Excited Ketones—Experimental[J].Chemphyschem,2010,3(1):79-97.
[7] MAI Y W,COTTERELL B.Oxidative and Nonoxidative Photodegradation of Nylon 6[J].Journal of Applied Polymer Science,2010,27(12):4 885-4 887.
[8] YANO S,MURAYAMA M.Effect of Photodegradation on Dynamic Mechanical Properties of Nylon 6[J].Journal of Applied Polymer Science,2010,25(3):433-447.
[9] CHRISTENSEN P A,EGERTON T A,MARTINS-FRANCHETTI S M,et al.Photodegradation of Polycaprolactone/Poly(vinyl chloride) Blend[J].Polymer Degradation & Stability,2008,93(1):305-309.
[10] NAKAMURA H,NAKAMURA T,NOGUCHI T,et al.Photodegradation of PEEK Sheets Under Tensile Stress[J].Polymer Degradation & Stability,2006,91(4):740-746.
[11] NAKAMURA T,OGUMA H,SASAKI N,et al.J191021 Strength Degradation Mechanisms of UV-irradiated PEEK Films[C]//Mechanical Engineering Congress,Japan:The Japan Society of Mechanical Engineers,2011.
[12] 高炜斌,韩世民,杨明娇,等.光氧老化对聚碳酸酯结构和性能的影响[J].高分子材料科学与工程,2008,24(10):67-70.GAO W B,HAN S M,YANG M J,et al.Effect of Photooxidative Aging on the Structure and Properties of Polycarbonate[J].Polymer Materials Science and Engineering,2008,24(10):67-70.
[13] 龚跃法,郑炎松,陈东红,等.有机化学[M].武汉:华中科技大学出版社,2012:188-209.
[14] PICKETT,JAMES E.Influence of Photo-Fries Reaction Products on the Photodegradation of Bisphenol-A Polycarbonate[J].Polymer Degradation & Stability,2011,96(12):2 253-2 265.
[15] MEHR M Y,DRIEL W D V,JANSEN K M B,et al.Photodegradation of Bisphenol A Polycarbonate Under Blue Light Radiation and Its Effect on Optical Properties[J].Optical Materials,2013,35(3):504-508.
[16] 周从恒,黄彦红,李丹,等.食品级聚碳酸酯的光氧老化性能[J].合成树脂及塑料,2017,34(4):6-8.ZHOU C H,HUANG Y H,LI D,et al.Photooxidative Aging Properties of Food Grade Polycarbonates[J].Synthetic Resins and Plastics,2017,34(4):6-8.
[17] OSAWA Z,KOBAYASHI S,SAITO T,et al.Comparative Study on the Degradation Behavior of Ethylene-carbon Monoxide Copolymers under Natural Environment in Japan and China[J].Journal of Materials Life Society,2011(6):134-145.
[18] ABANTO-BUENO J,LAMBROS J.Mechanical and Fracture Behavior of an Artificially Ultraviolet-irradiated Poly(ethylene-carbon monoxide) Copolymer[J].Journal of Applied Polymer Science,2010,92(1):139-148.
[19] SANGEN O,YAMAMOTO Y,IMAMURA R.Photodegradation of Polyether-Polyester Block Copolymers[J].Sen-ito Kogyo,2008,29(11):472-481.
[20] CHEN T,ZHANG J,YOU H.Photodegradation Behavior and Mechanism of Poly(ethylene glycol-co-1,4-cyclohexanedimethanol terephthalate) (PETG) Random Copolymers:Correlation with Copolymer Composition[J].Rsc Advances,2016,6(104):102 778-102 790.
[21] Manfred Schwab.Photosensitizer[M]//Encyclopedia of Cancer,Berlin Heidelberg:Springer Berlin Heidelberg,2011:2 881-2 882.
[22] 李晓龙,刘斌.光敏剂研究进展[J].中国激光医学杂志,2015(6):327-333.LI X L,LIU B.Progress in Photosensitizers[J].Chinese Journal of Laser Medicine,2015(6):327-333.
[23] 宁培森,王克昌,丁著明.二苯甲酮类紫外线吸收剂的发展趋势[J].塑料助剂,2008(2):7-12.NING P S,WANG K C,DING Z M.Development Trend of Benzophenone UV Absorbers[J].Plastics Additives,2008(2):7-12.
[24] RIYAJAN S A,SAKDAPIPANICH J T,TANAKA Y.Controlled Degradation of Cured Natural Rubber by Encapsulated Benzophenone as a Photosensitizer[J].Journal of Applied Polymer Science,2010,90(1):297-305.
[25] HOSONO K,KANAZAWA A,MORI H,et al.Photodegradation of Cellulose Acetate Film in the Presence of Benzophenone as a Photosensitizer[J].Journal of Applied Polymer Science,2010,105(6):3 235-3 239.
[26] EZEANI O E,IGWE I O,ONYEAGORO G N.The Effect of Benzophenone Photo-Initiator on Some Mechanical Properties of Photo-Oxidized Polypropylene/Thermoplastic Starch Blends[J].The International Journal of Engineering and Science,2017,6(1):43-51.
[27] 舒伟.光降解塑料的降解原理及其应用[J].印刷质量与标准化,2011(5):8-11.SHU W.Degradation Principle and Application of Photodegradable Plastics[J].Printing Quality and Standardization,2011(5):8-11
[28] 贾芳.低密度聚乙烯的光降解特性的研究[D].广州:广东工业大学,2008.
[29] SUáREZ-QUEZADA M,ROMERO-ORTIZ G,SUáREZ V,et al.Photodegradation of phenol using reconstructed Ce doped Zn/Al layered double hydroxides as photocatalysts[J].Catalysis Today,2016(271):213-219.
[30] 王怀庚.多组份聚乙烯降解薄膜的制备及其结构、性能的研究[D].苏州:苏州大学,2013.
[31] 李海龙,管明章,程凤梅.光敏剂对mLLDPE薄膜光氧化降解性能的影响[J].塑料科技,2011,39(5):88-91.LI H L,GUAN M Z,CHENG F M.Effects of Photosensitizers on Photooxidative Degradation of mLLDPE Films[J].Plastics Science,2011,39(5):88-91.
[32] LI H,LI H,CHENG F.Radiation Crosslinking of m-LLDPE Film with Different Photosensitizer[J].Polymer Materials Science & Engineering,2012,28(5):89-91,95.
[33] TAY T,DAS S,STEWART P.Magnesium Stearate Increases Salbutamol Sulphate Dispersion:What Is the Mechanism?[J].International Journal of Pharmaceutics,2009,383(1):62-69.
[34] OSAWA Z,KURISU N,NAGASHIMA K,et al.The Effect of Transition Metal Stearates on the Photodegradation of Polyethylene[J].Journal of Applied Polymer Science,2010,23(12):3 583-3 590.
[35] 杨根玲.稀土有机化合物催化LDPE光降解研究[J].广东化工,2013,40(13):41-42.YANG G L.Study on Photodegradation of LDPE Catalyzed by Rare Earth Organic Compounds[J].Guangdong Chemical Industry,2013,40(13):41-42.
[36] 谢孝勋,彭汉.可控光降解聚乙烯薄膜的研究[J].合成材料老化与应用,2009,6(1):1-4.XIE X X,PENG H.Study on Controllable Photodegradation of Polyethylene Films[J].Aging and Application of Synthetic Materials,2009,6(1):1-4.
[37] 梁力丽,罗学刚.光敏剂对聚乙烯地膜力学性能的影响[J].中国塑料,2008,22(7):88-91.LIANG L L,LUO X G.Effect of Photosensitizer on Mechanical Properties of Polyethylene Film[J].China Plastics,2008,22(7):88-91.
[38] 黄旭方,肖荔人,刘欣萍,等.几种光敏剂对聚乙烯光敏化效果的对比研究[J].福建师范大学学报(自然科学版),2011,27(2):70-75.HUANG X F,XIAO L R,LIU X P,et al.Comparative Study on Photosensitization Effect of Several Photosensitizers on Polyethylene[J].Journal of Fujian Normal University (Natural Science Edition),2011,27(2):70-75.
[39] LIN Y.Study of Ultraviolet Photooxidative Degradation of LDPE Film Containing Cerium Carboxylate Photosensitizer[J].Journal of Applied Polymer Science,2015,63(6):811-818.
[40] 孙琼.二氧化钛光催化、光敏化影响因素及机理研究[D].杭州:浙江大学,2011.
[41] DEVEAU P A,ARSAC F,THIVEL P X,et al.Different Methods in TiO2,Photodegradation Mechanism Studies:Gaseous and TiO2 -Adsorbed Phases[J].Journal of Hazardous Materials,2007,144(3):692-697.
[42] SHAWAPHUN S,MANANGAN T,WACHARAWICHA-NANT S.Thermo-and Photo-Degradation of LDPE and PP Films Using Metal Oxides as Catalysts[J].Advanced Materials Research,2010(93/94):505-508.
[43] YANG R,CHRISTENSEN P A,EGERTON T A,et al.Degradation Products Formed During UV Exposure of Polyethylene-ZnO Nano-composites[J].Polymer Degradation & Stability,2010,95(9):1 533-1 541.
[44] ELTAYEB E,BARIKANI M,MAHDAVIAN A,et al.An Investigation into the UV-Photo-Oxidative Degradation of LDPE by Using Cobalt Naphthenate as Photosensitizer[J].Journal of Macromolecular Science:Part D—Reviews in Polymer Processing,2010,49(7):718-724.
[45] YANG C,YE L,TIAN L,et al.Photodegradation Activity of Polyvinyl Chloride (PVC)-Perchlorinated Iron (II) Phthalocyanine (FePcCl16) Composite Film[J].Journal of Colloid & Interface Science,2011,353(2):537-541.
[46] 颜百愉,张安,彭伟鑫,等.回收塑料的光降解改性研究进展[J].广州化工,2017,45(13):14-15.YAN B Y,ZHANG A,PENG W X,et al.Research Progress on Photodegradation Modification of Recycled Plastics[J].Guangzhou Chemical,2017,45(13):14-15.