新型含磷共聚单体的合成及其阻燃不饱和树脂燃烧性能与机理的研究
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摘要
聚合物材料已被广泛应用于当今社会的各个领域。然而这些聚合物材料大都容易引燃并因此会引起严重的火灾问题。为了充分发挥这些聚合物材料在工业应用领域上的潜力,提高其阻燃性能已成为必要之举。总体而言,提高聚合物材料阻燃性能的方法可分为二类：“添加型”方式和“反应型”方式。前者通过将添加型阻燃剂以物理搅拌的方式加入到基体中。这种方法已取得了较为优异的阻燃效果。然而,添加型方式会遇到其它方面的问题：例如会遇到基体和阻燃剂之间界面结合力差的现象,这在一定程度上会破坏材料的其它性能,对力学性能的影响尤其严重。与“添加型”方式相比,“反应型”方式是通过将含有阻燃元素的基团引入到聚合物的分子链中取得永久性的阻燃性能。这种方法的特点在于可以通过分子设计改变聚合物材料的化学结构从而提高它们的整体性能。从可持续发展的角度来看,开发无卤环保型阻燃剂是当前学术界以及工业界的发展趋势。在众多卤素阻燃剂的替代品中,含磷型阻燃剂由于具备了“环境友好型”以及高效阻燃等优点,最近若干年成为了研究热点之一。在这之中,反应型含磷阻燃剂尤为引人关注-除了上述优点外,该类阻燃剂不会遇到添加型阻燃剂中经常出现的降低基体固有性能的问题。而且,通过合理的分子设计,该类反应型阻燃剂还能改善基体的其它性能。
基于前期的实验,文中主要内容包括合成若干各具特色的反应型阻燃单体,并将其与不饱和树脂反应,制备出不同的本质阻燃型不饱和树脂。本论文的研究工作如下所示：
1.以二氯化磷酸苯酯(PDCP)、双酚S、烯丙醇、丙烯酸-2-羟乙酯(HEA)作为反应原料,基于分子设计,调控阻燃元素P、S的比例关系,合成了两种双官能度的含磷、硫阻燃单体(DASPP和BADPS)。利用傅里叶红外光谱、‘H、31P-核磁共振谱成功表征其分子结构。将这两种阻燃单体分别通过自由基本体聚合与树脂反应后,制备出本质阻燃型不饱和树脂。利用热重分析、极限氧指数测试、锥形量热测试、差示扫描量热等手段研究了该材料的燃烧性能和热性能。结果表明在不饱和树脂分子中引入含磷、硫的阻燃单体能够显著提高材料的阻燃性能和高温热稳定性。差示扫描量热研究显示树脂材料的玻璃化转变温度随着阻燃单体含量的增加呈线性上升趋势。通过扫描电子显微镜和拉曼光谱研究发现这些单体能够有效地改善树脂燃烧后炭渣的微观结构以及石墨化程度,从而提高了树脂基体的热氧化稳定性以及在高温环境下的成炭效果。此外,利用实时红外光谱分析了不同不饱和树脂样品的热氧化降解过程,从而详细阐明了其降解机理。针对树脂材料的拉伸测试结果表明在树脂中引入上述含磷、硫的阻燃单体能够提高基体的力学性能。
2.基于前面的报道,利用更为简易的方法合成了一种环状结构的反应型含磷单体(EACGP),并通过自由基本体聚合与树脂反应后制备出高含磷量的本质阻燃型不饱和树脂。通过热重分析法、氧指数测试、微型燃烧量热测试等方法对该材料的燃烧性能和热性能进行了研究。由于该单体具有较高的含磷量,制备的本质阻燃型不饱和树脂的热释放速率峰值、总热释放量显著下降。同时,试样的极限氧指数(LOI)值、燃烧后的成炭量得到了有效的提高。在此基础上,采用实时红外光谱研究了该材料的热氧化降解行为,详细分析了阻燃单体的成炭效果以及不同树脂试样燃烧后炭层的形貌、结构。基于这些研究结果,进一步阐明了该本质阻燃型不饱和树脂的阻燃机理。
3.利用三氯氧磷、季戊四醇、烯丙醇等作为反应原料,合成了一种高含磷量的反应型阻燃单体(PDAP),并其与树脂通过自由基本体聚合反应后制备出本质阻燃型不饱和树脂。随后对该树脂的燃烧性能和热性能进行了相关研究。通过对热重分析测试的结果分析,发现该单体能够明显地改变不饱和树脂的降解过程：基体中阻燃单体与树脂的分子链在主要降解阶段相互反应,导致最大质量损失率(MMLR)显著下降,提高了成炭效果。利用极限氧指数测试、微型燃烧量热测试等对该材料的燃烧性能进行表征。测试结果的分析发现在含有阻燃单体的树脂中,其优异的阻燃性能归因于试样总热释放量、热释放容量的显著下降以及成炭量的提高。此外,通过热重-红外联用、实时红外光谱深入研究了该材料的热降解、热氧化降解行为。基于上述测试结果,对材料燃烧降解反应进行了详尽的分析,从而阐明了其降解机理。
4.调节反应条件,利用甲基膦酰二氯、乙二醇等原料分别合成了两种元素含量相同的含磷化合物(MCGP、PDMP),并将其分别加入不饱和树脂中固化反应。利用热重分析法、微型燃烧量热测试等手段对制备的阻燃型不饱和树脂样品进行了研究。结果表明尽管上述两种含磷化合物具有相同的元素含量,同时分子结构中相应原子的化学环境也完全一样,但是它们的阻燃机理并不相同。其中MCGP是基于气相阻燃机理作用,而PDMP中为凝聚相阻燃机理。因此这二者在燃烧测试等方面的表现也不尽一样。在此基础上,利用热重-红外连用光谱深入研究了它们的降解行为,从而阐明了其阻燃机理。
Modern polymer materials have been extensively applied in society. However, they are easily ignited and frequently suffer from fire risk issues. As a consequence, these drawbacks limit the application of the polymer materials to a great extent and must be overcome to reach their full potential. Generally, enhancing the flame retardancy of a polymer material can be achieved by an additive or reactive approach. The former, blending flame-retardant additives into the polymer, has demonstrated desirable efficacy in fire resistance. However, it usually encounters with unfavorable reactions between matrices and additives, which give rise to the deterioration of the polymer's properties (e.g., mechanical properties) to some extent. In contrast, the latter, incorporation of flame-retardant moieties into the polymer chains, demonstrates desirable characteristics of tailoring the properties of the material and optimizing its overall performance. From a sustainably developmental perspective, developing halogen-free FRs is a promising trend in both academic and industrial fields. Among numerous candidates, phosphorus-containing compounds have been the subject of intense research in recent years, owing to the environmental friendliness and efficacy in flame retardancy. Particularly, reactive phosphorus-containing FRs exhibit little or no compromise of the matrices'intrinsic properties in addition to a low required composition to achieve prominent nonflammability.
Inspired by previous findings, in this dissertation, we synthesized different reactive flame-retardant monomers and then introduced them into unsaturated polyester to prepare flame-retardant unsaturated polyester resins (FR-UPRs). The research work of this dissertation is presented as follows:
1. Two reactive phosphorus-and sulfur-containing monomer,[di(allyloxybisphenol sulfone) phenoxy phosphate (DASPP)] and [bis(acryloxyethyl diphenyl phosphate) sulfone, BADPS], were successfully synthesized and well characterized. Corresponding FR-UPRs with various amounts of monomer were prepared by radical bulk polymerization. The thermal properties and flammability of the FR-UPR samples were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), limiting oxygen index (LOI) measurements, and cone calorimetry. The results showed that the introduction of the phosphorus-and sulfur-containing monomer into unsaturated polyester resin (UPR) can substantially improve its fire resistance and high-temperature stability. Interestingly, a linear increase in the glass transition temperature (Tg) with increasing incorporated monomer content was observed by DSC. Scanning electron microscopy (SEM) and Raman spectroscopy studies revealed that these monomers can effectively improve the microstructure of UPR char residue and increase its graphitization degree, which can enhance the UPR's thermo-oxidative stability and char yield in high-temperature regions. Furthermore, real-time Fourier transform infrared (RTIR) spectroscopy was employed to study the thermo-oxidative degradation reactions of different UPR samples, providing insight into the degradation mechanism. In addition, results from tensile testing demonstrated the improved mechanical properties for the samples incorporated with these monomers.
2. A reactive cyclic phosphorus-containing monomer [ethyl acrylate cyclic glycol phosphate, EACGP] was synthesized in a facile way, and various amounts of EACGP were combined with unsaturated polyester by radical bulk polymerization. The resulting FR-UPR samples were investigated by TGA, LOI, and microscale combustion calorimetry (MCC) tests. Due to the high phosphorus content of EACGP, incorporation of this monomer led to a marked decrease in the peak heat release rate (pHRR), the total heat release (THR), an increase in the LOI, and the combustion char formation. Furthermore, RTIR spectroscopy was employed to investigate the thermo-oxidative degradation behavior of UPRs, and the charring effect of EACGP as well as the UPR char morphology was studied, illustrating the flame retardancy mechanism in UPR.
3. A novel reactive phosphorus-containing monomer [1-oxo-2,6,7-trioxa-1-phosphabicyclo-[2.2.2]octane-methyl diallyl phosphate, PDAP] was synthesized, and various amounts of PDAP were combined with unsaturated polyester by radical bulk polymerization. The thermal properties and flammability of the resulting UPR samples were studied. By means of TGA experiments it showed that incorporation of PDAP significantly altered the thermal decomposition pathway of the UPR. This phosphate-based flame retardant reduced the decomposition temperature of the resin and reacted with the polymer chains during the main decomposition step, contributing to a lowered maximum mass loss rate (MMLR) and enhanced char formation. The flammability of the UPRs was investigated with MCC and LOI tests. For the samples containing PDAP, marked nonflammability is attributed to the reduced HRC and THR as well as an enhanced char formation in the condensed phase. Furthermore, thermogravimetry-Fourier transform infrared (TG-FTIR) and RTIR spectroscopy were employed to gain insight into the degradation mechanism of UPRs. These results explicitly described the different chemical decomposition reactions in UPR after incorporation of PDAP.
4. In this part, two phosphorus-containing compounds with equal element content,[methyl cyclic glycol phosphonate,(MCGP) and poly1,2-dihydroxyethane phosphonate,(PDMP)] were synthesize and then added into unsaturated polyester for curing. The resulting FR-UPR samples were investigated by TGA and MCC tests. Interestingly, while both compounds are identical in element content and chemical bond, their flame retardancy mechanisms are different. Results showed that the flame retardancy mechanism for MCGP was active in gas phase, and PDMP exerted condensed phase flame retardant action, thus they demonstrated different performance in flammability tests. Furthermore, TG-FTIR spectroscopy was used to analyze their decomposition behaviors, elaborating the degradation mechanism of the samples.
基于前期的实验,文中主要内容包括合成若干各具特色的反应型阻燃单体,并将其与不饱和树脂反应,制备出不同的本质阻燃型不饱和树脂。本论文的研究工作如下所示：
1.以二氯化磷酸苯酯(PDCP)、双酚S、烯丙醇、丙烯酸-2-羟乙酯(HEA)作为反应原料,基于分子设计,调控阻燃元素P、S的比例关系,合成了两种双官能度的含磷、硫阻燃单体(DASPP和BADPS)。利用傅里叶红外光谱、‘H、31P-核磁共振谱成功表征其分子结构。将这两种阻燃单体分别通过自由基本体聚合与树脂反应后,制备出本质阻燃型不饱和树脂。利用热重分析、极限氧指数测试、锥形量热测试、差示扫描量热等手段研究了该材料的燃烧性能和热性能。结果表明在不饱和树脂分子中引入含磷、硫的阻燃单体能够显著提高材料的阻燃性能和高温热稳定性。差示扫描量热研究显示树脂材料的玻璃化转变温度随着阻燃单体含量的增加呈线性上升趋势。通过扫描电子显微镜和拉曼光谱研究发现这些单体能够有效地改善树脂燃烧后炭渣的微观结构以及石墨化程度,从而提高了树脂基体的热氧化稳定性以及在高温环境下的成炭效果。此外,利用实时红外光谱分析了不同不饱和树脂样品的热氧化降解过程,从而详细阐明了其降解机理。针对树脂材料的拉伸测试结果表明在树脂中引入上述含磷、硫的阻燃单体能够提高基体的力学性能。
2.基于前面的报道,利用更为简易的方法合成了一种环状结构的反应型含磷单体(EACGP),并通过自由基本体聚合与树脂反应后制备出高含磷量的本质阻燃型不饱和树脂。通过热重分析法、氧指数测试、微型燃烧量热测试等方法对该材料的燃烧性能和热性能进行了研究。由于该单体具有较高的含磷量,制备的本质阻燃型不饱和树脂的热释放速率峰值、总热释放量显著下降。同时,试样的极限氧指数(LOI)值、燃烧后的成炭量得到了有效的提高。在此基础上,采用实时红外光谱研究了该材料的热氧化降解行为,详细分析了阻燃单体的成炭效果以及不同树脂试样燃烧后炭层的形貌、结构。基于这些研究结果,进一步阐明了该本质阻燃型不饱和树脂的阻燃机理。
3.利用三氯氧磷、季戊四醇、烯丙醇等作为反应原料,合成了一种高含磷量的反应型阻燃单体(PDAP),并其与树脂通过自由基本体聚合反应后制备出本质阻燃型不饱和树脂。随后对该树脂的燃烧性能和热性能进行了相关研究。通过对热重分析测试的结果分析,发现该单体能够明显地改变不饱和树脂的降解过程：基体中阻燃单体与树脂的分子链在主要降解阶段相互反应,导致最大质量损失率(MMLR)显著下降,提高了成炭效果。利用极限氧指数测试、微型燃烧量热测试等对该材料的燃烧性能进行表征。测试结果的分析发现在含有阻燃单体的树脂中,其优异的阻燃性能归因于试样总热释放量、热释放容量的显著下降以及成炭量的提高。此外,通过热重-红外联用、实时红外光谱深入研究了该材料的热降解、热氧化降解行为。基于上述测试结果,对材料燃烧降解反应进行了详尽的分析,从而阐明了其降解机理。
4.调节反应条件,利用甲基膦酰二氯、乙二醇等原料分别合成了两种元素含量相同的含磷化合物(MCGP、PDMP),并将其分别加入不饱和树脂中固化反应。利用热重分析法、微型燃烧量热测试等手段对制备的阻燃型不饱和树脂样品进行了研究。结果表明尽管上述两种含磷化合物具有相同的元素含量,同时分子结构中相应原子的化学环境也完全一样,但是它们的阻燃机理并不相同。其中MCGP是基于气相阻燃机理作用,而PDMP中为凝聚相阻燃机理。因此这二者在燃烧测试等方面的表现也不尽一样。在此基础上,利用热重-红外连用光谱深入研究了它们的降解行为,从而阐明了其阻燃机理。
Modern polymer materials have been extensively applied in society. However, they are easily ignited and frequently suffer from fire risk issues. As a consequence, these drawbacks limit the application of the polymer materials to a great extent and must be overcome to reach their full potential. Generally, enhancing the flame retardancy of a polymer material can be achieved by an additive or reactive approach. The former, blending flame-retardant additives into the polymer, has demonstrated desirable efficacy in fire resistance. However, it usually encounters with unfavorable reactions between matrices and additives, which give rise to the deterioration of the polymer's properties (e.g., mechanical properties) to some extent. In contrast, the latter, incorporation of flame-retardant moieties into the polymer chains, demonstrates desirable characteristics of tailoring the properties of the material and optimizing its overall performance. From a sustainably developmental perspective, developing halogen-free FRs is a promising trend in both academic and industrial fields. Among numerous candidates, phosphorus-containing compounds have been the subject of intense research in recent years, owing to the environmental friendliness and efficacy in flame retardancy. Particularly, reactive phosphorus-containing FRs exhibit little or no compromise of the matrices'intrinsic properties in addition to a low required composition to achieve prominent nonflammability.
Inspired by previous findings, in this dissertation, we synthesized different reactive flame-retardant monomers and then introduced them into unsaturated polyester to prepare flame-retardant unsaturated polyester resins (FR-UPRs). The research work of this dissertation is presented as follows:
1. Two reactive phosphorus-and sulfur-containing monomer,[di(allyloxybisphenol sulfone) phenoxy phosphate (DASPP)] and [bis(acryloxyethyl diphenyl phosphate) sulfone, BADPS], were successfully synthesized and well characterized. Corresponding FR-UPRs with various amounts of monomer were prepared by radical bulk polymerization. The thermal properties and flammability of the FR-UPR samples were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), limiting oxygen index (LOI) measurements, and cone calorimetry. The results showed that the introduction of the phosphorus-and sulfur-containing monomer into unsaturated polyester resin (UPR) can substantially improve its fire resistance and high-temperature stability. Interestingly, a linear increase in the glass transition temperature (Tg) with increasing incorporated monomer content was observed by DSC. Scanning electron microscopy (SEM) and Raman spectroscopy studies revealed that these monomers can effectively improve the microstructure of UPR char residue and increase its graphitization degree, which can enhance the UPR's thermo-oxidative stability and char yield in high-temperature regions. Furthermore, real-time Fourier transform infrared (RTIR) spectroscopy was employed to study the thermo-oxidative degradation reactions of different UPR samples, providing insight into the degradation mechanism. In addition, results from tensile testing demonstrated the improved mechanical properties for the samples incorporated with these monomers.
2. A reactive cyclic phosphorus-containing monomer [ethyl acrylate cyclic glycol phosphate, EACGP] was synthesized in a facile way, and various amounts of EACGP were combined with unsaturated polyester by radical bulk polymerization. The resulting FR-UPR samples were investigated by TGA, LOI, and microscale combustion calorimetry (MCC) tests. Due to the high phosphorus content of EACGP, incorporation of this monomer led to a marked decrease in the peak heat release rate (pHRR), the total heat release (THR), an increase in the LOI, and the combustion char formation. Furthermore, RTIR spectroscopy was employed to investigate the thermo-oxidative degradation behavior of UPRs, and the charring effect of EACGP as well as the UPR char morphology was studied, illustrating the flame retardancy mechanism in UPR.
3. A novel reactive phosphorus-containing monomer [1-oxo-2,6,7-trioxa-1-phosphabicyclo-[2.2.2]octane-methyl diallyl phosphate, PDAP] was synthesized, and various amounts of PDAP were combined with unsaturated polyester by radical bulk polymerization. The thermal properties and flammability of the resulting UPR samples were studied. By means of TGA experiments it showed that incorporation of PDAP significantly altered the thermal decomposition pathway of the UPR. This phosphate-based flame retardant reduced the decomposition temperature of the resin and reacted with the polymer chains during the main decomposition step, contributing to a lowered maximum mass loss rate (MMLR) and enhanced char formation. The flammability of the UPRs was investigated with MCC and LOI tests. For the samples containing PDAP, marked nonflammability is attributed to the reduced HRC and THR as well as an enhanced char formation in the condensed phase. Furthermore, thermogravimetry-Fourier transform infrared (TG-FTIR) and RTIR spectroscopy were employed to gain insight into the degradation mechanism of UPRs. These results explicitly described the different chemical decomposition reactions in UPR after incorporation of PDAP.
4. In this part, two phosphorus-containing compounds with equal element content,[methyl cyclic glycol phosphonate,(MCGP) and poly1,2-dihydroxyethane phosphonate,(PDMP)] were synthesize and then added into unsaturated polyester for curing. The resulting FR-UPR samples were investigated by TGA and MCC tests. Interestingly, while both compounds are identical in element content and chemical bond, their flame retardancy mechanisms are different. Results showed that the flame retardancy mechanism for MCGP was active in gas phase, and PDMP exerted condensed phase flame retardant action, thus they demonstrated different performance in flammability tests. Furthermore, TG-FTIR spectroscopy was used to analyze their decomposition behaviors, elaborating the degradation mechanism of the samples.
引文
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1. Ruan, T.; Wang, Y.; Wang, C.; Wang, P.; Fu, J.; Yin, Y.; Qu, G.; Wang, T.; Jiang, G., Identification and Evaluation of a Novel Heterocyclic Brominated Flame Retardant Tris(2,3-dibromopropyl) Isocyanurate in Environmental Matrices near a Manufacturing Plant in Southern China. Environmental Science & Technology 2009, 43 (9),3080-3086.
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11. Chen, H.; Zhang, K.; Xu, J., Synthesis and characterizations of novel phosphorous-nitrogen containing poly(ether sulfone)s. Polym Degrad Stabil 2011,96 (2),197-203.
12. Lin, C. H.; Chang, S. L.; Wei, T. P., High-T-g Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols. Macromol Chem Physic 2011,212 (5),455-464.
13. Wang, Y. Z.; Yi, B.; Wu, B.; Yang, B.; Liu, Y, Thermal behaviors of flame-retardant polycarbonates containing diphenyl sulfonate and poly(sulfonyl phenylene phosphonate). J Appl Polym Sci 2003,89 (4),882-889.
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15. Wang, B. B.; Tang, Q. B.; Hong, N. N.; Song, L; Wang, L.; Shi, Y Q.; Hu, Y, Effect of Cellulose Acetate Butyrate Microencapsulated Ammonium Polyphosphate on the Flame Retardancy, Mechanical, Electrical, and Thermal Properties of Intumescent Flame-Retardant Ethylene-Vinyl Acetate Copolymer/Microencapsulated Ammonium Polyphosphate/Polyamide-6 Blends. Acs Appl Mater Inter 2011,3 (9),3754-3761.
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17. Wang, D. Y.; Liu, X. Q.; Wang, J. S.; Wang, Y. Z.; Stec, A. A.; Hull, T. R., Preparation and characterisation of a novel fire retardant PET/alpha-zirconium phosphate nanocomposite. Polym Degrad Stabil 2009,94 (4),544-549.
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1. Ruan, T.; Wang, Y.; Wang, C.; Wang, P.; Fu, J.; Yin, Y.; Qu, G.; Wang, T.; Jiang, G., Identification and Evaluation of a Novel Heterocyclic Brominated Flame Retardant Tris(2,3-dibromopropyl) Isocyanurate in Environmental Matrices near a Manufacturing Plant in Southern China. Environmental Science & Technology 2009, 43 (9),3080-3086.
2. Galip, H.; Hasipoglu, H.; Gunduz, G., Flame-retardant polyester. J Appl Polym Sci 1999,74 (12),2906-2910.
3. Kicko-Walczak, E., New generation of fire retardant polyester resins. Macromol Symp 2003,199,343-350.
4. Shih, Y.F.; Wang, Y. T.; Jeng, R. J.; Wei, K. M., Expandable graphite systems for phosphorus-containing unsaturated polyesters. I. Enhanced thermal properties and flame retardancy. Polym Degrad Stabil 2004,86 (2),339-348.
5. Song, P. A.; Shen, Y.; Du, B. X.; Peng, M.; Shen, L.; Fang, Z. P., Effects of Reactive Compatibilization on the Morphological, Thermal, Mechanical, and Rheological Properties of Intumescent Flame-Retardant Polypropylene. Acs Appl Mater Inter 2009, 1 (2),452-459.
6. Yuan, H.; Xing, W.; Zhang, P.; Song, L.; Hu, Y, Functionalization of Cotton with UV-Cured Flame Retardant Coatings. Industrial & Engineering Chemistry Research 2012,51 (15),5394-5401.
7. Qian, X.; Song, L.; Hu, Y.; Yuen, R. K. K.; Chen, L.; Guo, Y.; Hong, N.; Jiang, S., Combustion and Thermal Degradation Mechanism of a Novel Intumescent Flame Retardant for Epoxy Acrylate Containing Phosphorus and Nitrogen. Industrial & Engineering Chemistry Research 2011,50 (4),1881-1892.
8. Kandare, E.; Kandola, B. K.; Price, D.; Nazare, S.; Horrocks, R. A., Study of the thermal decomposition of flame-retarded unsaturated polyester resins by thermogravimetric analysis and Py-GC/MS. Polym Degrad Stabil 2008,93 (11), 1996-2006.
9. Tai, Q. L.; Chen, L. J.; Song, L.; Nie, S. B.; Hu, Y.; Yuen, R. K. K., Preparation and thermal properties of a novel flame retardant copolymer. Polym Degrad Stabil 2010,95 (5),830-836.
10. Tai, Q. L.; Song, L.; Hu, Y.; Yuen, R. K. K.; Feng, H.; Tao, Y. J., Novel styrene polymers functionalized with phosphorus-nitrogen containing molecules:Synthesis and properties. Mater. Chem. Phys.2012,134 (1),163-169.
11. Price, D.; Cunliffe, L. K.; Bullett, K. J.; Hull, T. R.; Milnes, G. J.; Ebdon, J. R.; Hunt, B. J.; Joseph, P., Thermal behaviour of covalently bonded phosphate and phosphonate flame retardant polystyrene systems. Polym Degrad Stabil 2007,92 (6),1101-1114.
12. Ebdon, J. R.; Price, D.; Hunt, B. J.; Joseph, P.; Gao, F. G.; Milnes, G. J.; Cunliffe, L. K., Flame retardance in some polystyrenes and poly(methyl methacrylate)s with covalently bound phosphorus-containing groups:initial screening experiments and some laser pyrolysis mechanistic studies. Polym Degrad Stabil 2000,69 (3),267-277.
13. Vahabi, H.; Ferry, L.; Longuet, C.; Sonnier, R.; Negrell-Guirao, C; David, G.; Lopez-Cuesta, J. M., Theoretical and empirical approaches to understanding the effect of phosphonate groups on the thermal degradation for two chemically modified PMMA. Eur. Polym. J.2012,48 (3),604-612.
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16. Zhang, C.; Liu, S. M.; Huang, J. Y.; Zhao, J. Q., The Synthesis and Flame Retardance of a High Phosphorus-containing Unsaturated Polyester Resin. Chemistry Letters 2010,39 (12),1270-1272.
17. Zhang, C.; Huang, J. Y.; Liu, S. M.; Zhao, J. Q., The synthesis and properties of a reactive flame-retardant unsaturated polyester resin from a phosphorus-containing diacid. Polym Advan Technol 2011,22 (12),1768-1777.
18. Kuan, J. F.; Lin, K. F., Synthesis of hexa-allylamino-cyclotriphosphazene as a reactive fire retardant for unsaturated polyesters. J Appl Polym Sci 2004,91 (2), 697-702.
19. Braun, U.; Knoll, U.; Schartel, B.; Hoffmann, T.; Pospiech, D.; Artner, J.; Ciesielski, M.; Doring, M.; Perez-Gratero, R.; Sandler, J. K. W.; Altstadt, V., Novel phosphorus-containing poly(ether sulfone)s and their blends with an epoxy resin: Thermal decomposition and fire retardancy. Macromol Chem Physic 2006,207 (16), 1501-1514.
20. Chen, H.; Zhang, K.; Xu, J., Synthesis and characterizations of novel phosphorous-nitrogen containing poly(ether sulfone)s. Polym Degrad Stabil 2011,96 (2),197-203.
21. Lin, J.-F.; Ho, C.-F.; Huang, S. K., Thermal characterization of the phosphorus-containing sulfone-modified epoxy resins by thermogravimetric analysis and direct pyrolysis-GC/MS measurement on the thermally degradative volatiles. Polym Degrad Stabil 2000,67 (1),137-147.
22. Lin, C. H.; Chang, S. L.; Wei, T. P., High-T-g Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols. Macromol Chem Physic 2011,212 (5),455-464.
23. Wang, Y. Z.; Yi, B.; Wu, B.; Yang, B.; Liu, Y., Thermal behaviors of flame-retardant polycarbonates containing diphenyl sulfonate and poly(sulfonyl phenylene phosphonate). J Appl Polym Sci 2003,89 (4),882-889.
24. Liaw, D. J., Synthesis of sulfone-containing polyphosphates:Low temperature solution polycondensation of bisphenol S analogues and aryl phosphorodichlorides. Polym Degrad Stabil 1997,55 (3),301-308.
25. Wang, B. B.; Tang, Q. B.; Hong, N. N.; Song, L.; Wang, L.; Shi, Y. Q.; Hu, Y., Effect of Cellulose Acetate Butyrate Microencapsulated Ammonium Polyphosphate on the Flame Retardancy, Mechanical, Electrical, and Thermal Properties of Intumescent Flame-Retardant Ethylene-Vinyl Acetate Copolymer/Microencapsulated Ammonium Polyphosphate/Polyamide-6 Blends. Acs Appl Mater Inter 2011,3 (9),3754-3761.
26. Ma, H. Y.; Tong, L. R.; Xu, Z. B.; Fang, Z. P.; Jin, Y. M.; Lu, F. Z., A novel intumescent flame retardant:Synthesis and application in ABS copolymer. Polym Degrad Stabil 2007,92 (4),720-726p
27. Wang, D. Y.; Liu, X. Q.; Wang, J. S.; Wang, Y. Z.; Stec, A. A.; Hull, T. R., Preparation and characterisation of a novel fire retardant PET/alpha-zirconium phosphate nanocomposite. Polym Degrad Stabil 2009,94 (4),544-549.
28. Ma, H. Y.; Tong, L. F.; Xu, Z. B.; Fang, Z. P., Functionalizing carbon nanotubes by grafting on intumescent flame retardant:Nanocomposite synthesis, morphology, rheology, and flammability. Adv Funct Mater 2008,18 (3),414-421.
29. Bourbigot, S.; LeBras, M.; Delobel, R.; Tremillon, J. M., Synergistic effect of zeolite in an intumescence process-Study of the interactions between the polymer and the additives. Journal of the Chemical Society-Faraday Transactions 1996,92 (18), 3435-3444.
30. Braun, U.; Balabanovich, A. I.; Schartel, B.; Knoll, U.; Artner, J.; Ciesielski, M.; Doring, M.; Perez, R.; Sandler, J. K. W.; Altstadt, V.; Hoffmann, T.; Pospiech, D., Influence of the oxidation state of phosphorus on the decomposition and fire behaviour of flame-retarded epoxy resin composites. Polymer 2006,47 (26),8495-8508.
31. Tai, Q. L.; Hu, Y.; Yuen, R. K. K.; Song, L.; Lu, H. D., Synthesis, structure-property relationships of polyphosphoramides with high char residues. Journal of Materials Chemistry 2011,21 (18),6621-6627.
32. Lakshmi, R. T. S. M.; Kumari, R.; Varma, I. K., Structure and thermal characterisation of poly(arylene ether sulphone)s. J Therm Anal Calorim 2004,78 (3), 809-819.
33. Sadezky, A.; Muckenhuber, H.; Grothe, H.; Niessner, R.; Poschl, U., Raman micro spectroscopy of soot and related carbonaceous materials:Spectral analysis and structural information. Carbon 2005,43 (8),1731-1742.
34. Tenbrinke, G.; Karasz, F. E.; Ellis, T. S., Depression of Glass-Transition Temperatures of Polymer Networks by Diluents. Macromolecules 1983,16 (2), 244-249.
35. Carlier, V.; Devaux, J.; Legras, R.; Mcgrail, P. T., Percentage of Rigid Chain-Length, a New Concept for Predicting Glass-Transition Temperatures and Melting-Points of Poly(Aryl Ether Ketone)S and Poly(Aryl Ether Sulfone)S. Macromolecules 1992,25 (24),6646-6650.
36. Zhang, H. Q.; Farris, R. J.; Westmoreland, P. R., Low flammability and thermal decomposition behavior of poly(3,3'-dihydroxybiphenylisophthalamide) and its derivatives. Macromolecules 2003,36 (11),3944-3954.
37. Benin, V.; Durganala, S.; Morgan, A. B., Synthesis and flame retardant testing of new boronated and phosphonated aromatic compounds. Journal of Materials Chemistry 2012,22(3),1180-1190.
38. Levchik, S. V.; Weil, E. D., A review of recent progress in phosphorus-based flame retardants. Journal of Fire Sciences 2006,24 (5),345-364.
39. Kandola, B. K.; Horrocks, A. R.; Myler, P.; Blair, D., New developments in flame retardancy of glass-reinforced epoxy composites. J Appl Polym Sci 2003,88 (10), 2511-2521.
40. Shah, D.; Maiti, P.; Gunn, E.; Schmidt, D.F.; Jiang, D. D.; Batt, C. A.; Giannelis, E. R., Dramatic enhancements in toughness of polyvinylidene fluoride nanocomposites via nanoclay-directed crystal structure and morphology. Advanced Materials 2004,16 (14),1173-+.
41. Zulfiqar, S.; Ahmad, Z.; Sarwar, M. I., Soluble aromatic polyamide bearing ether linkages:synthesis and characterization. Colloid Polym Sci 2007,285 (15),1749-1754.
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12. Tibiletti, L.; Longuet, C.; Ferry, L.; Coutelen, P.; Mas, A.; Robin, J. J.; Lopez-Cuesta, J. M., Thermal degradation and fire behaviour of unsaturated polyesters filled with metallic oxides. Polym. Degrad. Stab.2011,96 (1),67-75.
13. Price, D.; Cunliffe, L. K.; Bullett, K. J.; Hull, T. R.; Milnes, G. J.; Ebdon, J. R.; Hunt, B. J.; Joseph, P., Thermal behaviour of covalently bonded phosphate and phosphonate flame retardant polystyrene systems. Polym. Degrad. Stab.2007,92 (6),1101-1114.
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17. Braun, U.; Balabanovich, A. I.; Schartel, B.; Knoll, U.; Artner, J.; Ciesielski, M.; Doring, M.; Perez, R.; Sandler, J. K. W.; Altstadt, V.; Hoffmann, T.; Pospiech, D., Influence of the oxidation state of phosphorus on the decomposition and fire behaviour of flame-retarded epoxy resin composites. Polymer 2006,47 (26),8495-8508.
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