聚氨酯预聚物接枝L-羟脯氨酸催化剂的制备和高温防腐节能示温涂料的研制
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摘要
本文综述了L-脯氨酸、L-脯氨酸催化不对称反应、聚合物固载化L-脯氨酸的方法等；概述了高温防腐涂料、隔热涂料、耐高温基料树脂和示温涂料,以及项目研究的目的和意义。研究了以L-脯氨酸作为催化剂在二乙基2-(2-氰乙基)丙二酸合成中的应用,探索了以聚氨酯预聚物接枝L-羟脯氨酸催化剂的制备及在Michael加成反应中的应用；制备了高温防腐底层涂料、隔热涂料、封闭反射涂料和超温报警涂料,进行了实际应用试验。
(1)以丙二酸二乙酯与丙烯腈为原料,以L-脯氨酸作为催化剂,通过迈克尔加成反应来制备二乙基2-(2-氰乙基)丙二酸,主要研究了反应时间、反应温度、催化剂的用量、原料配比及溶剂种类对产物的产率和ee值的影响。在吡啶为溶剂,反应温度35℃,反应时间48h的条件下,产物的产率及ee值分别为74.10%和79%。结果表明反应时间、催化剂用量和原料的配比对产物的ee值没有明显的影响,而反应温度对ee值的影响较大;反应溶剂的对产物的ee值影响较大。
(2)以TDI分别与一缩二乙二醇、聚醚-204和三羟甲基丙烷反应来合成聚氨酯预聚物,通过氨基保护的L-羟脯氨酸与聚氨酯预聚物进行反应后再脱保护的方法,制备出聚氨酯接枝的L-羟脯氨酸,其催化性能不如L-羟脯氨酸,需要进一步研究。
(3)研究了不同环氧改性有机硅树脂的性能,以化学改性的方法制备了环氧改性有机硅树脂,综合性能良好,以用腰果壳油改性胺作为固化剂,以ND-42作为促进剂,加入硅酸盐填料后,制备的涂膜性能良好,可以作为高温涂料的基料粘结剂；市售产品H-4的性能也较好,能够应用于高温涂料。
(4)研究了颜基比、颜填料组成及用量、助剂用量等对涂料性能的影响,确定了底层防腐涂料的配方工艺。试验表明,底层涂料的颜基比为1.4：1-1.6：1之间是合适的,颜填料组成为环保型防锈颜料,结合片状填料、惰性填料及硅酸盐类填料,所制备防腐的性能良好,耐高温性能优异。
(5)研究了空心陶瓷微珠、陶瓷漂珠、膨胀蛭石粉和膨胀珍珠岩粉的隔热性能,考察了颜基比、填料用量、助剂等对涂料性能的影响,确定了隔热涂料配方工艺。试验表明,隔热涂料的理想的颜基比为2.2：1～2.5：1之间；利用偶联剂KH550对陶瓷微珠进行处理,可提高隔热涂层的抗开裂性能和耐温性能；涂层的厚度为1.5mm时,涂层的隔热温差达到30℃。
(6)以非浮型铝粉、云母粉、沉淀硫酸钡和滑石粉为颜填料制备的涂层的封闭性能比较理想,对隔热也有一定的提高。反射封闭涂料的颜基比在1.6：1～1.8：1之间是较合适的。
(7)研究了基料树脂、靛蓝的变色性能、肌醇对涂料变色温度的影响、颜基比及颜填料的用量等。结果表明,以1053型有机硅树脂为基料粘结剂,为靛蓝和肌醇变色颜料,钛白粉为对比颜料,滑石粉为填料,有机硅偶联剂KH550为固化促进剂,制备的示温涂料性能满足指标要求。
(8)对所研制的涂料进行了中试生产和应用试验,抽样检测结果表明,涂料的性能能够达到指标要求,当涂层厚度为1.1mm以上时,隔热温差达到20℃以上；使用一年后,涂层完好。
The asymmetric catalytic reaction by L-proline、L-proline and the method of L-proline immobilized on polymer were summarized in the dissertation. The aim for the project of high-temperature anticorrosion coatings, heat insulation paint, high temperature resistant binder resin and temperature indicating coatings was also described. The synthesis of diethyl 2-(2 cyanoethylated) propylene acid catalyzed by L-proline was studied. The synthesis of polyurethane prepolymer grafted L-hyp catalyst and its application on Michael reaction were explored. High temperature corrosion primer, heat insulation paint, closed reflecting coatings and overtemperature alarm coatings were synthesized and its application tests were carried out.
(1) Diethyl 2-(2-cyanoethyl) malonate was prepared by Michael reaction from diethyl malo-nate and acrylonitrile catalized by L-proline. The effect of reaction time, reaction temperature, the amount of catalyst, the ratio of feed and the solvent on the yied and ee value was studied. The yied of 74.10% and the ee value of 79% were abtained at 35℃for 48h using pyridine as solvent. The results illustrated that the effect of reaction time, the amount of catalyst and the ratio of feed did not affect the ee value obviously. The solvent affect the ee value significantly.
(2) Polyurethane grafted L-hyp was synthesized by reaction of polyurethane prepolymer with L-hyp protected by amino which left off after reaction. Polyurethane prepolymer was obtained by reaction of TDI with one suo glycol, polyether-204 and TMP respectively. The reason why the catalytic ability of Polyurethane grafted L-hyp was weaker than L-hyp needs to be studied.
(3) The performance of silicon resin modified by expoxy was studied. The integrated performance of expoxy modified silicon resin synthesized by chemical method was good. Using cashew shell oil modified amine as curing agent, using ND-42 as promoted agent and added with silicates, the film could be used as adhesive of high temperature paint. The performance of the commercial H-4 is also good, which could be applied in high temperature paint.
(4) The effect of P/B, pigments and fillers composition and amount and the additives amount on the paint performance was studied. The technology of bottom anticorrosive coatings was confirmed. The experiments illustrated that the P/B between 1.4:1～1.6:1 is favorable. The anticorrosion properties of the pigment is good, and the anti-high temperature performance is perfect.
(5) The heat insulation of hollow ceramic beads, ceramic drift beads, expanded vermiculite and expanded perlite powder was studied. The effect of P/B, fillers amount and additives on the paint properties was also studied, while determining the technologh of the heat insulation paint. The ideal P/B is between 2.2:1 and 2.5:1. The anti-cracking and anti-high temperature performance improved by treating paint using KH550. The insulation temperature difference reached 30℃when the thickness of the paint was 1.5 mm.
(6) The sealing properties of the paint prepared using The float type aluminum powder, mica powder, precipitation barite ore and talcum powder as pigment is good, and the insulation properties was also improved in some degree. The proper pigment to binder ratio of reflective coatings sealed paint is between 1.6:1～1.8:1.
(7) The color-changing properties of makings resin, indigo, and the effect of inositol on color-changing temperature, P/B, pigments and fillers amount were studied. The results illustrated that the properties of temperature indicating coatings prepared with 1053 type silicon resin as makings resin, with indigo and inositol as color-changing pigment, with titanium dioxide as contrast color, with talcum powder as fillers reached the requirements.
(8) The middle-industry production of the paint and the sampling test were carried out. The results illustrated that the properties of the paint met the requirements. The coating of the paint was not destroyed after one-year use. The insulation properties of the paint was related with the coating thickness. The insulation temperature difference reached more than 20℃when the thickness of the paint was more than 1.1 mm.
(1)以丙二酸二乙酯与丙烯腈为原料,以L-脯氨酸作为催化剂,通过迈克尔加成反应来制备二乙基2-(2-氰乙基)丙二酸,主要研究了反应时间、反应温度、催化剂的用量、原料配比及溶剂种类对产物的产率和ee值的影响。在吡啶为溶剂,反应温度35℃,反应时间48h的条件下,产物的产率及ee值分别为74.10%和79%。结果表明反应时间、催化剂用量和原料的配比对产物的ee值没有明显的影响,而反应温度对ee值的影响较大;反应溶剂的对产物的ee值影响较大。
(2)以TDI分别与一缩二乙二醇、聚醚-204和三羟甲基丙烷反应来合成聚氨酯预聚物,通过氨基保护的L-羟脯氨酸与聚氨酯预聚物进行反应后再脱保护的方法,制备出聚氨酯接枝的L-羟脯氨酸,其催化性能不如L-羟脯氨酸,需要进一步研究。
(3)研究了不同环氧改性有机硅树脂的性能,以化学改性的方法制备了环氧改性有机硅树脂,综合性能良好,以用腰果壳油改性胺作为固化剂,以ND-42作为促进剂,加入硅酸盐填料后,制备的涂膜性能良好,可以作为高温涂料的基料粘结剂；市售产品H-4的性能也较好,能够应用于高温涂料。
(4)研究了颜基比、颜填料组成及用量、助剂用量等对涂料性能的影响,确定了底层防腐涂料的配方工艺。试验表明,底层涂料的颜基比为1.4：1-1.6：1之间是合适的,颜填料组成为环保型防锈颜料,结合片状填料、惰性填料及硅酸盐类填料,所制备防腐的性能良好,耐高温性能优异。
(5)研究了空心陶瓷微珠、陶瓷漂珠、膨胀蛭石粉和膨胀珍珠岩粉的隔热性能,考察了颜基比、填料用量、助剂等对涂料性能的影响,确定了隔热涂料配方工艺。试验表明,隔热涂料的理想的颜基比为2.2：1～2.5：1之间；利用偶联剂KH550对陶瓷微珠进行处理,可提高隔热涂层的抗开裂性能和耐温性能；涂层的厚度为1.5mm时,涂层的隔热温差达到30℃。
(6)以非浮型铝粉、云母粉、沉淀硫酸钡和滑石粉为颜填料制备的涂层的封闭性能比较理想,对隔热也有一定的提高。反射封闭涂料的颜基比在1.6：1～1.8：1之间是较合适的。
(7)研究了基料树脂、靛蓝的变色性能、肌醇对涂料变色温度的影响、颜基比及颜填料的用量等。结果表明,以1053型有机硅树脂为基料粘结剂,为靛蓝和肌醇变色颜料,钛白粉为对比颜料,滑石粉为填料,有机硅偶联剂KH550为固化促进剂,制备的示温涂料性能满足指标要求。
(8)对所研制的涂料进行了中试生产和应用试验,抽样检测结果表明,涂料的性能能够达到指标要求,当涂层厚度为1.1mm以上时,隔热温差达到20℃以上；使用一年后,涂层完好。
The asymmetric catalytic reaction by L-proline、L-proline and the method of L-proline immobilized on polymer were summarized in the dissertation. The aim for the project of high-temperature anticorrosion coatings, heat insulation paint, high temperature resistant binder resin and temperature indicating coatings was also described. The synthesis of diethyl 2-(2 cyanoethylated) propylene acid catalyzed by L-proline was studied. The synthesis of polyurethane prepolymer grafted L-hyp catalyst and its application on Michael reaction were explored. High temperature corrosion primer, heat insulation paint, closed reflecting coatings and overtemperature alarm coatings were synthesized and its application tests were carried out.
(1) Diethyl 2-(2-cyanoethyl) malonate was prepared by Michael reaction from diethyl malo-nate and acrylonitrile catalized by L-proline. The effect of reaction time, reaction temperature, the amount of catalyst, the ratio of feed and the solvent on the yied and ee value was studied. The yied of 74.10% and the ee value of 79% were abtained at 35℃for 48h using pyridine as solvent. The results illustrated that the effect of reaction time, the amount of catalyst and the ratio of feed did not affect the ee value obviously. The solvent affect the ee value significantly.
(2) Polyurethane grafted L-hyp was synthesized by reaction of polyurethane prepolymer with L-hyp protected by amino which left off after reaction. Polyurethane prepolymer was obtained by reaction of TDI with one suo glycol, polyether-204 and TMP respectively. The reason why the catalytic ability of Polyurethane grafted L-hyp was weaker than L-hyp needs to be studied.
(3) The performance of silicon resin modified by expoxy was studied. The integrated performance of expoxy modified silicon resin synthesized by chemical method was good. Using cashew shell oil modified amine as curing agent, using ND-42 as promoted agent and added with silicates, the film could be used as adhesive of high temperature paint. The performance of the commercial H-4 is also good, which could be applied in high temperature paint.
(4) The effect of P/B, pigments and fillers composition and amount and the additives amount on the paint performance was studied. The technology of bottom anticorrosive coatings was confirmed. The experiments illustrated that the P/B between 1.4:1～1.6:1 is favorable. The anticorrosion properties of the pigment is good, and the anti-high temperature performance is perfect.
(5) The heat insulation of hollow ceramic beads, ceramic drift beads, expanded vermiculite and expanded perlite powder was studied. The effect of P/B, fillers amount and additives on the paint properties was also studied, while determining the technologh of the heat insulation paint. The ideal P/B is between 2.2:1 and 2.5:1. The anti-cracking and anti-high temperature performance improved by treating paint using KH550. The insulation temperature difference reached 30℃when the thickness of the paint was 1.5 mm.
(6) The sealing properties of the paint prepared using The float type aluminum powder, mica powder, precipitation barite ore and talcum powder as pigment is good, and the insulation properties was also improved in some degree. The proper pigment to binder ratio of reflective coatings sealed paint is between 1.6:1～1.8:1.
(7) The color-changing properties of makings resin, indigo, and the effect of inositol on color-changing temperature, P/B, pigments and fillers amount were studied. The results illustrated that the properties of temperature indicating coatings prepared with 1053 type silicon resin as makings resin, with indigo and inositol as color-changing pigment, with titanium dioxide as contrast color, with talcum powder as fillers reached the requirements.
(8) The middle-industry production of the paint and the sampling test were carried out. The results illustrated that the properties of the paint met the requirements. The coating of the paint was not destroyed after one-year use. The insulation properties of the paint was related with the coating thickness. The insulation temperature difference reached more than 20℃when the thickness of the paint was more than 1.1 mm.
引文
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