Synthesis of reactive DOPO-based flame retardant and its application in rigid polyisocyanurate-polyurethane foam
•A reactive low-molecular flame-retardant polyester diol based on DDP was synthetized.•The flame-retardant RPUF-PIR reached a high LOI value of 28.0 vol% with a 3.5 wt% phosphorus content and the NCO/OH ratio of 3.5.•The density and compressive strength of PIRs were improved with the content of phos...
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| Published in | Polymer degradation and stability Vol. 197; p. 109852 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Elsevier Ltd
01.03.2022
Elsevier BV |
| Subjects | |
| Online Access | Get full text |
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| Abstract | •A reactive low-molecular flame-retardant polyester diol based on DDP was synthetized.•The flame-retardant RPUF-PIR reached a high LOI value of 28.0 vol% with a 3.5 wt% phosphorus content and the NCO/OH ratio of 3.5.•The density and compressive strength of PIRs were improved with the content of phosphorus increased from 0 to 3.75 wt% (NCO/OH = 2.5).
In this study, a reactive flame-retardant diol (BEOPMS) was synthesized by the esterification reaction of 9,10-dihydro-10-[2,3-di(hydroxycarbonyl)propyl]-10- phospha-phenanthrene-10-oxide with diethylene glycol. The flame-retardant effect of it combined with polyaryl polymethylene isocyanate (PMDI) were tested for rigid polyisocyanurate-polyurethane foams (PIRs) fabricated via a one-step process. The higher limiting oxygen index (LOI) and char residue yield value of flame-retardant rigid polyurethane foam (FRPUF) (21.0 vol% and 21.9 wt%, respectively) at 3.5 wt% phosphorus content compared to those of the pure rigid polyurethane foam (RPUF) (17.0 vol% and 16.3 wt%, respectively), illustrating the great effect of BEOPMS on improving the flame retardancy of the foams. At a 3.5 molar ratio of NCO/OH and 3.5 wt% content of phosphorus, an even higher LOI value of PIR (28.0 vol%) with a highest char residue yield (44.7 wt%) was obtained. The flame-retardant mechanism was discussed according to the scanning electron microscope (SEM), energy dispersive spectrometer (EDS), cone calorimeter (CC) and thermal gravimetric analysis-Fourier-transform infrared analyses (TG-IR). It is recognized that the isocyanurate ring groups can improve the thermostability of resultant PIRs, and increase the char residue yield in combination with the higher content of PMDI. Meanwhile, the thermal degradation of BEOPMS produces phosphate in condensed phase and released PO and PO₂ free radicals, which inhibits the free radical chain reactions in the gas phase and thus enables a superior flame retardancy effect for polyurethane foams.
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| AbstractList | In this study, a reactive flame-retardant diol (BEOPMS) was synthesized by the esterification reaction of 9,10-dihydro-10-[2,3-di(hydroxycarbonyl)propyl]-10- phospha-phenanthrene-10-oxide with diethylene glycol. The flame-retardant effect of it combined with polyaryl polymethylene isocyanate (PMDI) were tested for rigid polyisocyanurate-polyurethane foams (PIRs) fabricated via a one-step process. The higher limiting oxygen index (LOI) and char residue yield value of flame-retardant rigid polyurethane foam (FRPUF) (21.0 vol% and 21.9 wt%, respectively) at 3.5 wt% phosphorus content compared to those of the pure rigid polyurethane foam (RPUF) (17.0 vol% and 16.3 wt%, respectively), illustrating the great effect of BEOPMS on improving the flame retardancy of the foams. At a 3.5 molar ratio of NCO/OH and 3.5 wt% content of phosphorus, an even higher LOI value of PIR (28.0 vol%) with a highest char residue yield (44.7 wt%) was obtained. The flame-retardant mechanism was discussed according to the scanning electron microscope (SEM), energy dispersive spectrometer (EDS), cone calorimeter (CC) and thermal gravimetric analysis-Fourier-transform infrared analyses (TG-IR). It is recognized that the isocyanurate ring groups can improve the thermostability of resultant PIRs, and increase the char residue yield in combination with the higher content of PMDI. Meanwhile, the thermal degradation of BEOPMS produces phosphate in condensed phase and released PO and PO₂ free radicals, which inhibits the free radical chain reactions in the gas phase and thus enables a superior flame retardancy effect for polyurethane foams. •A reactive low-molecular flame-retardant polyester diol based on DDP was synthetized.•The flame-retardant RPUF-PIR reached a high LOI value of 28.0 vol% with a 3.5 wt% phosphorus content and the NCO/OH ratio of 3.5.•The density and compressive strength of PIRs were improved with the content of phosphorus increased from 0 to 3.75 wt% (NCO/OH = 2.5). In this study, a reactive flame-retardant diol (BEOPMS) was synthesized by the esterification reaction of 9,10-dihydro-10-[2,3-di(hydroxycarbonyl)propyl]-10- phospha-phenanthrene-10-oxide with diethylene glycol. The flame-retardant effect of it combined with polyaryl polymethylene isocyanate (PMDI) were tested for rigid polyisocyanurate-polyurethane foams (PIRs) fabricated via a one-step process. The higher limiting oxygen index (LOI) and char residue yield value of flame-retardant rigid polyurethane foam (FRPUF) (21.0 vol% and 21.9 wt%, respectively) at 3.5 wt% phosphorus content compared to those of the pure rigid polyurethane foam (RPUF) (17.0 vol% and 16.3 wt%, respectively), illustrating the great effect of BEOPMS on improving the flame retardancy of the foams. At a 3.5 molar ratio of NCO/OH and 3.5 wt% content of phosphorus, an even higher LOI value of PIR (28.0 vol%) with a highest char residue yield (44.7 wt%) was obtained. The flame-retardant mechanism was discussed according to the scanning electron microscope (SEM), energy dispersive spectrometer (EDS), cone calorimeter (CC) and thermal gravimetric analysis-Fourier-transform infrared analyses (TG-IR). It is recognized that the isocyanurate ring groups can improve the thermostability of resultant PIRs, and increase the char residue yield in combination with the higher content of PMDI. Meanwhile, the thermal degradation of BEOPMS produces phosphate in condensed phase and released PO and PO₂ free radicals, which inhibits the free radical chain reactions in the gas phase and thus enables a superior flame retardancy effect for polyurethane foams. [Display omitted] |
| ArticleNumber | 109852 |
| Author | Qian, Xue Li, Hui Zhang, Laibao Liu, Qiang Yan, Shouke Liu, Jiwen |
| Author_xml | – sequence: 1 givenname: Xue surname: Qian fullname: Qian, Xue organization: Key Laboratory of Rubber-Plastics, Ministry of Education/Shandong Provincial Key Laboratory of Rubber-Plastics, Qingdao University of science & technology, Qingdao 266042, China – sequence: 2 givenname: Qiang surname: Liu fullname: Liu, Qiang email: liuqiang@qust.edu.cn organization: Key Laboratory of Rubber-Plastics, Ministry of Education/Shandong Provincial Key Laboratory of Rubber-Plastics, Qingdao University of science & technology, Qingdao 266042, China – sequence: 3 givenname: Laibao surname: Zhang fullname: Zhang, Laibao organization: Independent Researcher, Baton Rouge, LA 70820, USA – sequence: 4 givenname: Hui surname: Li fullname: Li, Hui organization: Key Laboratory of Rubber-Plastics, Ministry of Education/Shandong Provincial Key Laboratory of Rubber-Plastics, Qingdao University of science & technology, Qingdao 266042, China – sequence: 5 givenname: Jiwen surname: Liu fullname: Liu, Jiwen organization: Key Laboratory of Rubber-Plastics, Ministry of Education/Shandong Provincial Key Laboratory of Rubber-Plastics, Qingdao University of science & technology, Qingdao 266042, China – sequence: 6 givenname: Shouke surname: Yan fullname: Yan, Shouke email: skyan@qust.edu.cn organization: Key Laboratory of Rubber-Plastics, Ministry of Education/Shandong Provincial Key Laboratory of Rubber-Plastics, Qingdao University of science & technology, Qingdao 266042, China |
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| Keywords | Flame retardant Rigid polyurethane foam Polyisocyanurate Flame-retardant diol |
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| Snippet | •A reactive low-molecular flame-retardant polyester diol based on DDP was synthetized.•The flame-retardant RPUF-PIR reached a high LOI value of 28.0 vol% with... In this study, a reactive flame-retardant diol (BEOPMS) was synthesized by the esterification reaction of 9,10-dihydro-10-[2,3-di(hydroxycarbonyl)propyl]-10-... |
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| SubjectTerms | Antifreeze solutions calorimeters Chemical synthesis Cone calorimeters diethylene glycol energy-dispersive X-ray analysis Esterification Flame retardant Flame retardants Flame-retardant diol foams Fourier transforms Free radicals Gravimetric analysis Infrared analysis Isocyanates oxygen Phenanthrene phosphates Phosphorus phosphorus content Plastic foam Polyisocyanurate Polyurethane Polyurethane foam polyurethanes Residues Rigid polyurethane foam Thermal degradation Thermal stability Vapor phases |
| Title | Synthesis of reactive DOPO-based flame retardant and its application in rigid polyisocyanurate-polyurethane foam |
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