DOPO及其衍生物在聚合物阻燃改性中的应用研究进展
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摘要
由于卤素阻燃剂的毒性和环境问题,磷系阻燃剂作为一种环境友好型阻燃剂已引起人们的广泛关注.9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)及其衍生物作为一种无卤含磷阻燃剂,在聚合物中主要以气相阻燃机理表现出优异的阻燃性能.相比于卤系阻燃剂,DOPO及其衍生物在燃烧过程中所释放出的腐蚀性和毒性气体很少.近年来,通过各种化学反应和合成方法,开发了众多含DOPO结构的有机及无机阻燃剂,许多含DOPO结构的阻燃剂得到了学术界和工业界的青睐.此外,以DOPO为原料合成有机磷化合物阻燃改性高分子材料的研究报道越来越多.因此,本文综述了有机-DOPO类阻燃剂以及无机-DOPO类阻燃剂的制备、阻燃机理及其在聚合物阻燃改性中的应用,并对其在阻燃应用方向作了进一步的展望.
Due to the toxicity and environmental problems of halogen flame retardants, phosphorous flame retardants as environmentally friendly flame retardants have attracted extensive attention.As a halogen-free phosphorus-containing flame retardant, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide(DOPO) and its derivatives show excellent flame retardant properties.Gas-phase inhibition is considered as the main mechanism of DOPO flame‐retardant effect for polymers.Compared withhalogen-free flame retardants, DOPO and its derivatives emit less corrosive and toxic gases during combustion. In recent years, many organic and inorganic flame retardants containing DOPO structure have been developed through various chemical reactions and synthetic methods. In addition, more and more researches have been reported on the synthesis of organophosphorus compound flame retardant modified polymer materials with DOPO as raw materials. So, in this paper, the synthesis, mechanism and application of organic-DOPO flame retardants and inorganic-DOPO flame retardants were reviewed, and the direction of application and development were expected.
Due to the toxicity and environmental problems of halogen flame retardants, phosphorous flame retardants as environmentally friendly flame retardants have attracted extensive attention.As a halogen-free phosphorus-containing flame retardant, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide(DOPO) and its derivatives show excellent flame retardant properties.Gas-phase inhibition is considered as the main mechanism of DOPO flame‐retardant effect for polymers.Compared withhalogen-free flame retardants, DOPO and its derivatives emit less corrosive and toxic gases during combustion. In recent years, many organic and inorganic flame retardants containing DOPO structure have been developed through various chemical reactions and synthetic methods. In addition, more and more researches have been reported on the synthesis of organophosphorus compound flame retardant modified polymer materials with DOPO as raw materials. So, in this paper, the synthesis, mechanism and application of organic-DOPO flame retardants and inorganic-DOPO flame retardants were reviewed, and the direction of application and development were expected.
引文
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[6] LONG L,YIN J,HE W,et al.Synergistic effect of different nanoparticles on flame retardant poly(lactic acid) with bridged DOPO derivative[J].Polymer Composites,2019,40(3):1043-1052.
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[9] YASIN S,BEHARY N,GIRAUD S,et al.In situ degradation of organophosphorus flame retardant on cellulosic fabric using advanced oxidation process:A study on degradation and characterization[J].Polymer Degradation and Stability,2016,126(1):1-8.
[10] 郭军红,郭永亮,慕波,等.DOPOHM/丙烯酸树脂复合材料的制备及其阻燃性能[J].精细化工,2017,34(2):138-144.GUO J H,GUO Y L,MU B,et al.Preparation and flame retardancy of DOPOHM/acrylic resin composites[J].Fine Chemicals,2017,34(2):138-144.
[11] HIRSCH C,STRIEGL B,MATHES S,et al.Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants[J].Archives of Toxicology,2017,91(1):407-425.
[12] XIU L,SALMERIA K A,RENTSCH D,et al.Thermal decomposition and flammability of rigid PU foams containing some DOPO derivatives and other phosphorus compounds[J].Journal of Analytical & Applied Pyrolysis,2017,124:219-229.
[13] FANG Y,QIAN L,HUANG Z,et al.Synergistic charring effect of triazinetrione-alkyl-phosphinate and phosphaphenanthrene derivatives in epoxy thermosets[J].RSC Advances,2017,7(73):46505-46513.
[14] JIA L,ZHANG W C,TONG B,et al.Crystallization,mechanical and flame-retardant properties of poly(lactic acid) composites with DOPO and DOPO-POSS[J].Chinese Journal of Polymer Science,2018,36(7):1-9.
[15] SALMERIA K A,GAAN S.An overview of some recent advances in DOPO-derivatives:Chemistry and flame retardant applications[J].Polymer Degradation and Stability,2015,113:119-134.
[16] 蒋俊奎,杨朝明,张旭东,等.DOPO衍生物的合成及其在阻燃聚碳酸酯中的应用[J].塑料工业,2018,46(4):134-137.JIANG J K,YANG C M,ZHANG X D,et al.Synthesis of DOPO derivative and its application in flame retardant polycarbonate [J].Plastics Industry,2018,46(4):134-137.
[17] PENG W,CAI Z.Highly efficient flame-retardant epoxy resin with a novel DOPO-based triazole compound:Thermal stability,flame retardancy and mechanism[J].Polymer Degradation & Stability,2017,137:138-150.
[18] XIE M,ZHANG S,DING Y,et al.Synthesis of a heat-resistant DOPO derivative and its application as flame‐retardant in engineering plastics[J].Journal of Applied Polymer Science,2017,134(22):44892.
[19] 鲁哲宏,康兴隆,冯伟丽,等.生物质阻燃剂的研究进展[J].河南大学学报(自然科学版),2018,48(6):710-716.LU Z H,KANG X L,FENG W L,et al.Research progress of bio-based flame retardants[J].Journal of Henan University(Natural Science),2018,48(6):710-716.
[20] ZHAN D,LI Y,YANG C,et al.Assessment of organophosphate flame retardants in surface water and sediment from a freshwater environment [J].Environmental Monitoring and Assessment,2018,190(4):222-253.
[21] HUANG C C,ZENG Y H,LUO X J,et al.Level changes and human dietary exposure assessment of halogenated flame retardant levels in free-range chicken eggs:A case study of a former e-waste recycling site [J].Science of the Total Environment,2018,634:509-515.
[22] 鲁哲宏,冯伟丽,康兴隆,等.苯并χ嗪协效二乙基次磷酸铝阻燃PA66的研究[J].精细化工,2019,36(2):322-327.LU Z H,FENG W L,KANG X L,et al.Research of flame retardant PA66 composites with benzoxazine and diethyl-phosphate aluminum[J].Fine Chemicals,2019,36(2):322-327.
[23] LORS C,PONGE J F,DAMIDOT D.Microscopy in addition to chemical analyses and ecotoxicological assays for the environmental hazard assessment of coal tar-polluted soils [J].Environmental Science and Pollution Research,2018,25(3):1-9.
[24] PEREIRA J L,PEREIRA P,PADEIRO A,et al.Environmental hazard assessment of contaminated soils in Antarctica:Using a structured tier 1 approach to inform decision-making[J].Science of the Total Environment,2017,574:443-454.
[25] PORFIRYEY B N,TULUPOY A S.Environmental hazard assessment and forecast of economic damage from industrial accidents[J].Studies on Russian Economic Development,2017,28(6):600-607.
[26] CHEN X Y,HUANG Z H,XI X Q,et al.Synergistic effect of carbon and phosphorus flame retardants in rigid polyurethane foams[J].Fire & Materials,2018,42(3):447-453.
[27] RABE S,CHUENBAN Y,SCHARTEL B.Exploring the modes of action of phosphorus-based flame retardants in polymeric systems[J].Materials,2017,10(5):455.
[28] HOANG D Q,PHAM T L,NGUYEN T H,et al.Organo-phosphorus flame retardants for poly(vinyl chloride)/wood flour composite[J].Polymer Composites,2016,39(3):961-970.
[29] 鲁哲宏,班大赛,李豪,等.阻燃改性尼龙研究进展[J].化学研究,2018,29(3):310-316.LU Z H,BAN D S,LI H,et al.Research progress of flame retardant modified nylon[J].Chemical Research,2018,29(3):310-316.
[30] CAI J,WIRASAPUTRA A,ZHU Y,et al.The flame retardancy and rheological properties of PA6/MCA modifiedby DOPO-based chainextender[J].RSC Advances,2017,7(32):19593-19603.
[31] PAN W,LONG X,JIAN R,et al.Flame-retarding epoxy resin with an efficient P/N/S-containing flame retardant:Preparation,thermal stability,and flame retardance[J].Polymer Degradation & Stability,2018,149:69-77.
[33] TANG S,QIANL ,LIU X ,et al.Gas-phase flame-retardant effects of a bi-group compound based on phosphaphenanthrene and triazine-trione groups in epoxy resin[J].Polymer Degradation and Stability,2016,133(1):350-357.
[34] YAN W,ZHANG M Q,YU J,et al.Synergistic flame-retardant effect of epoxy resin combined with phenethyl-bridged DOPO derivative and graphene nanosheets[J].Chinese Journal of Polymer Science,2019(1):79-88.
[35] 严伟,李乾波,王番,等.纳米OMMT与DOPO衍生物协同阻燃环氧树脂[J].工程塑料应用,2018,345(7):110-114.YAN W,LI Q B,WANG F,et al.Synergistic flame retardant epoxy resin with nano OMMT and DOPO derivative [J].Application of engineering plastics,2018,345(7):110-114.
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