CN108559072A - One kind polyarylether of structure containing anthrone and preparation method thereof - Google Patents
One kind polyarylether of structure containing anthrone and preparation method thereof Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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Abstract
一种含蒽酮结构聚芳醚及其制备方法，涉及一种化工材料及其制备方法，本发明以具有大体积刚性扭曲结构的蒽酮结构双酚单体与双卤单体X‑Ar‑X为原料，碱、碱金属或碱土金属的盐类为催化剂，在非质子极性溶剂中，通过溶液缩聚制备。新型含蒽酮结构聚芳醚树脂机械强度高，可溶解，耐高温。在聚芳醚主链中引入大体积刚性扭曲蒽酮结构，不但提高聚合物玻璃化转变温度，提升其耐热性能，而且蒽酮结构的共轭结构可提高聚合物的耐热耐氧化稳定性，提高其在极端环境下稳定性，在高性能分离膜、耐高温高性能结构材料、复合材料、油漆、涂料、涂层等方面具有很好的应用前景。An anthrone-containing polyaryl ether and a preparation method thereof, relating to a chemical material and a preparation method thereof, the invention uses an anthrone-structure bisphenol monomer and a dihalogen monomer X-Ar- X is the raw material, the salts of alkali, alkali metal or alkaline earth metal are catalysts, and it is prepared by solution polycondensation in an aprotic polar solvent. The new polyarylether resin containing anthrone structure has high mechanical strength, is soluble, and can withstand high temperature. Introducing a large-volume rigid twisted anthrone structure into the main chain of polyarylether can not only increase the glass transition temperature of the polymer, but also improve its heat resistance, and the conjugated structure of the anthrone structure can improve the heat resistance and oxidation resistance of the polymer. , improve its stability in extreme environments, and have good application prospects in high-performance separation membranes, high-temperature-resistant high-performance structural materials, composite materials, paints, coatings, coatings, etc.
Description
技术领域technical field
本发明涉及一种化工材料及其制备方法，特别是涉及一种含蒽酮结构聚芳醚及其制备方法。The invention relates to a chemical material and a preparation method thereof, in particular to a polyarylether containing anthrone structure and a preparation method thereof.
背景技术Background technique
聚芳醚类聚合物具有优异的机械性能、耐热性能、耐化学性能和加工性能，可作为特种工程塑料，可在承受机械应力和较为苛刻的化学物理环境中长期使用。典型聚芳醚聚合物如聚醚醚酮，具有优异耐热和机械性能，但溶解性差，在耐高温涂料、分离膜方面应用受到极大限制。随着科学技术的发展，现有的聚芳醚材料已经不能满足高技术领域对特种工程塑料的性能需求，因此迫切需要开发聚芳醚新材料。在聚芳醚主链中引入大体积刚性扭曲蒽酮结构，获得的新型含蒽酮结构聚芳醚机械强度高，可溶解，耐高温。在聚芳醚主链中引入大体积刚性蒽酮结构，不但提高聚合物玻璃化转变温度，提升其耐热性能，而且蒽酮结构的共轭结构可提高聚合物的耐热和耐氧化稳定性，提高其在极端环境下稳定性，在高性能分离膜、耐高温高性能结构材料、复合材料、油漆、涂料、涂层等需要耐化学性能耐高温高性能材料的领域具有十分广阔的应用前景。Polyarylene ether polymers have excellent mechanical properties, heat resistance, chemical resistance and processability. They can be used as special engineering plastics and can be used for a long time in mechanical stress and harsh chemical and physical environments. Typical polyarylether polymers, such as polyether ether ketone, have excellent heat resistance and mechanical properties, but their solubility is poor, and their applications in high-temperature resistant coatings and separation membranes are greatly limited. With the development of science and technology, the existing polyarylether materials can no longer meet the performance requirements of special engineering plastics in the high-tech field, so it is urgent to develop new polyarylether materials. A large-volume rigid twisted anthrone structure is introduced into the main chain of the polyarylether, and the obtained new polyarylether containing anthrone structure has high mechanical strength, is soluble, and is resistant to high temperature. Introducing a large-volume rigid anthrone structure into the polyarylether main chain not only increases the glass transition temperature of the polymer and improves its heat resistance, but also the conjugated structure of the anthrone structure can improve the heat resistance and oxidation resistance of the polymer. , improve its stability in extreme environments, and have very broad application prospects in the fields of high-performance separation membranes, high-temperature-resistant high-performance structural materials, composite materials, paints, coatings, coatings, etc. that require chemical-resistant high-temperature resistant high-performance materials .
发明内容Contents of the invention
本发明的目的在于提供一种含蒽酮结构聚芳醚及其制备方法，本发明以具有大体积刚性扭曲结构的蒽酮结构双酚单体与双卤单体X-Ar-X为原料，碱、碱金属或碱土金属的盐类为催化剂，在非质子极性溶剂中，通过溶液缩聚制备。制备含蒽酮结构聚芳醚树脂机械强度高，可溶解，耐高温，在极端环境下稳定性，在高性能分离膜、耐高温高性能结构材料、复合材料、油漆、涂料、涂层等方面具有很好的应用前景。The object of the present invention is to provide a polyarylether containing anthrone structure and its preparation method. The present invention uses anthrone structure bisphenol monomer and dihalogen monomer X-Ar-X with large-volume rigid twisted structure as raw materials, Salts of alkali, alkali metal or alkaline earth metal are used as catalysts, and are prepared by solution polycondensation in an aprotic polar solvent. The preparation of polyarylether resins containing anthrone structures has high mechanical strength, solubility, high temperature resistance, and stability in extreme environments. It has a good application prospect.
本发明的目的是通过以下技术方案实现的：The purpose of the present invention is achieved through the following technical solutions:
一种含蒽酮结构聚芳醚，构成该聚芳醚的重复结构单元为：A polyarylether containing anthrone structure, the repeating structural unit constituting the polyarylether is:
其中，x=0.01-1.0，R1，R2为氢原子或烷氧基或烷基或苯基或卤原子。Wherein, x=0.01-1.0, R 1 and R 2 are hydrogen atom or alkoxyl group or alkyl group or phenyl group or halogen atom.
一种含蒽酮结构聚芳醚制备方法，所述方法包括一种含蒽酮结构聚芳醚及以非质子极性溶剂或者含有非质子极性溶剂的混合溶剂为反应溶剂，以碱，碱金属或碱土金属的盐类为催化剂的制备含蒽酮结构聚芳醚的方法；该方法以蒽酮结构双酚单体和芳香双卤单体为原料，在高温下进行聚合反应，反应中进行共沸脱水，反应结束后体系中加入溶剂稀释，将聚合物溶液倒入沉淀剂，搅拌下将聚合物沉淀出来，过滤分离，得到聚合物。A method for preparing a polyarylether containing anthrone structure, the method comprising a polyarylether containing anthrone structure and using an aprotic polar solvent or a mixed solvent containing an aprotic polar solvent as a reaction solvent, using alkali, alkali A method for preparing polyarylethers containing anthrone structures using salts of metals or alkaline earth metals as catalysts; the method uses bisphenol monomers with anthrone structures and aromatic dihalogen monomers as raw materials to perform polymerization at high temperature, and proceed during the reaction. Azeotropic dehydration, after the reaction is completed, solvent is added to the system to dilute, the polymer solution is poured into a precipitating agent, the polymer is precipitated under stirring, and the polymer is obtained by filtration and separation.
所述的一种含蒽酮结构聚芳醚制备方法，所述非质子极性溶剂包括N-甲基吡咯烷酮、N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、环丁砜、二甲基亚砜、二苯砜中的一种或两种以上的混合物。In the preparation method of a polyarylether containing anthrone structure, the aprotic polar solvent includes N -methylpyrrolidone, N,N -dimethylformamide, N, N-dimethylacetamide, sulfolane , dimethyl sulfoxide, diphenyl sulfone or a mixture of two or more.
所述的一种含蒽酮结构聚芳醚制备方法，所述以碱为催化剂，碱包括氢氧化锂、氢氧化钠、氢氧化钾、氢氧化镁、氢氧化钙、氢氧化锶、氢氧化钡中的一种或两种以上的混合物。In the preparation method of polyarylether containing anthrone structure, the base is used as the catalyst, and the base includes lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, hydroxide One or a mixture of two or more of barium.
所述的一种含蒽酮结构聚芳醚制备方法，所述碱金属或碱土金属的盐类为催化剂，碱金属或碱土金属的盐类包括碳酸锂、碳酸钠、碳酸钾、碳酸铯、碳酸镁、碳酸钙、碳酸锶、碳酸钡、碳酸氢钠、碳酸氢钾、碳酸氢镁或碳酸氢钙中的一种或两种以上的混合物。In the preparation method of polyarylether containing anthrone structure, the salts of alkali metal or alkaline earth metal are catalysts, and the salts of alkali metal or alkaline earth metal include lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, carbonic acid One or a mixture of two or more of magnesium, calcium carbonate, strontium carbonate, barium carbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate or calcium bicarbonate.
所述的一种含蒽酮结构聚芳醚制备方法，所述聚合反应温度为50-300℃，反应时间为2-48小时。In the preparation method of polyarylether containing anthrone structure, the polymerization reaction temperature is 50-300°C, and the reaction time is 2-48 hours.
所述的一种含蒽酮结构聚芳醚制备方法，所述共沸脱水剂包括苯、甲苯、二甲苯和氯苯。In the preparation method of polyarylether containing anthrone structure, the azeotropic dehydrating agent includes benzene, toluene, xylene and chlorobenzene.
所述的一种含蒽酮结构聚芳醚制备方法，所述沉淀剂包括水、甲醇和乙醇。In the preparation method of polyarylether containing anthrone structure, the precipitation agent includes water, methanol and ethanol.
本发明的优点与效果是：Advantage and effect of the present invention are:
本发明以具有大体积刚性扭曲结构的蒽酮结构双酚单体与双卤单体X-Ar-X为原料，碱、碱金属或碱土金属的盐类为催化剂，在非质子极性溶剂中，通过溶液缩聚制备。新型含蒽酮结构聚芳醚树脂机械强度高，可溶解，耐高温。在聚芳醚主链中引入大体积刚性扭曲蒽酮结构，不但提高聚合物玻璃化转变温度，提升其耐热性能，而且蒽酮结构的共轭结构可提高聚合物的耐热耐氧化稳定性，提高其在极端环境下稳定性，在高性能分离膜、耐高温高性能结构材料、复合材料、油漆、涂料、涂层等方面具有很好的应用前景。The present invention uses anthrone structure bisphenol monomers and dihalogen monomers X-Ar-X with a large rigid twisted structure as raw materials, and salts of alkalis, alkali metals or alkaline earth metals as catalysts, in an aprotic polar solvent , prepared by solution polycondensation. The new polyarylether resin containing anthrone structure has high mechanical strength, is soluble, and can withstand high temperature. Introducing a large-volume rigid twisted anthrone structure into the main chain of polyarylether can not only increase the glass transition temperature of the polymer, but also improve its heat resistance, and the conjugated structure of the anthrone structure can improve the heat resistance and oxidation resistance of the polymer. , improve its stability in extreme environments, and have good application prospects in high-performance separation membranes, high-temperature-resistant high-performance structural materials, composite materials, paints, coatings, coatings, etc.
附图说明Description of drawings
图1为实施例1的聚合物薄膜的红外吸收光谱；Fig. 1 is the infrared absorption spectrum of the polymer thin film of embodiment 1;
图2为实施例2的聚合物薄膜的红外吸收光谱。Fig. 2 is the infrared absorption spectrum of the polymer film of Example 2.
具体实施方式Detailed ways
下面结合实施例对本发明进行详细说明。The present invention will be described in detail below in conjunction with examples.
本发明的内容是以蒽酮结构双酚单体与芳香族双卤单体为原料，合成含蒽酮结构聚芳醚，其特征在于构成该聚合物的重复结构单元为：The content of the present invention is to use anthrone structure bisphenol monomer and aromatic dihalogen monomer as raw materials to synthesize polyarylether containing anthrone structure, which is characterized in that the repeating structural unit constituting the polymer is:
其中，x=0.01-1.0，R1，R2为氢原子或烷氧基或烷基或苯基或卤原子。Wherein, x=0.01-1.0, R 1 and R 2 are hydrogen atom or alkoxyl group or alkyl group or phenyl group or halogen atom.
本发明的具体合成方法是以蒽酮结构双酚单体和双卤单体为原料，在极性溶剂中，以碱、碱金属或碱土金属的盐类为催化剂，在高温下进行聚合，反应中进行共沸脱水，反应结束后，用溶剂稀释，然后用水或乙醇为沉淀剂，搅拌下将聚合物沉淀出来，得到聚合物。The specific synthesis method of the present invention is to use anthrone structure bisphenol monomer and dihalogen monomer as raw materials, in a polar solvent, with alkali, alkali metal or alkaline earth metal salts as catalyst, polymerize at high temperature, react Azeotropic dehydration in a medium, after the reaction, dilute with a solvent, then use water or ethanol as a precipitating agent, and precipitate the polymer under stirring to obtain a polymer.
本发明采用的含蒽酮结构双酚单体的结构通式是：The general structural formula of the bisphenol monomer containing anthrone structure that the present invention adopts is:
，R1，R2为氢原子或烷氧基或烷基或苯基或卤原子。本发明采用的双卤单体是如下结构： , R 1 , R 2 are a hydrogen atom or an alkoxy group or an alkyl group or a phenyl group or a halogen atom. The dihalogen monomer that the present invention adopts is following structure:
其中，卤原子(X)为氟或氯。 Among them, the halogen atom (X) is fluorine or chlorine.
本发明聚合反应温度控制在50-300℃，聚合反应时间为2-48小时。可以表示为：The polymerization reaction temperature of the present invention is controlled at 50-300 DEG C, and the polymerization reaction time is 2-48 hours. It can be expressed as:
其中，x=0.01-1.0；Among them, x=0.01-1.0;
聚合反应经脱水预聚阶段，采用共沸脱水剂共沸脱水，然后将共沸脱水剂蒸出，升温，反应溶液粘度逐步增大。待溶液粘度显著增大，达到要求之后，停止加热，逐步冷却降温，终止反应。反应结束后，用水、乙醇或甲醇为沉淀剂，搅拌下降聚合物沉淀出来，过滤得到聚合物。The polymerization reaction goes through the dehydration prepolymerization stage, using azeotropic dehydrating agent for azeotropic dehydration, and then steaming out the azeotropic dehydrating agent, raising the temperature, and the viscosity of the reaction solution gradually increases. After the viscosity of the solution increases significantly and meets the requirements, stop heating, gradually cool down, and terminate the reaction. After the reaction is finished, use water, ethanol or methanol as a precipitating agent, stir and drop the polymer to precipitate out, and filter to obtain the polymer.
本发明采用的非质子极性溶剂包括N-甲基吡咯烷酮、N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、环丁砜、二甲基亚砜、二苯砜中的一种或两种以上的混合物。The aprotic polar solvent used in the present invention comprises one of N -methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, sulfolane, dimethylsulfoxide, diphenylsulfone a mixture of two or more.
本发明采用的碱为催化剂，碱包括氢氧化锂、氢氧化钠、氢氧化钾、氢氧化镁、氢氧化钙、氢氧化锶、氢氧化钡中的一种或两种以上的混合物。The alkali used in the present invention is a catalyst, and the alkali includes one or a mixture of two or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide and barium hydroxide.
本发明采用的碱金属的盐类为催化剂，碱金属的盐类包括碳酸锂、碳酸钠、碳酸钾、碳酸铯、碳酸镁、碳酸钙、碳酸锶、碳酸钡、碳酸氢钠、碳酸氢钾、碳酸氢镁或碳酸氢钙中的一种或两种以上的混合物。The salts of alkali metals used in the present invention are catalysts, and the salts of alkali metals include lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, sodium bicarbonate, potassium bicarbonate, One or more mixtures of magnesium bicarbonate or calcium bicarbonate.
本发明采用的聚合反应温度为50-300℃，反应时间为2-48小时。The polymerization reaction temperature adopted in the present invention is 50-300 DEG C, and the reaction time is 2-48 hours.
本发明采用的共沸脱水剂包括苯、甲苯、二甲苯和氯苯。The azeotropic dehydrating agent used in the present invention includes benzene, toluene, xylene and chlorobenzene.
本发明采用的沉淀剂包括水、甲醇和乙醇。Precipitants used in the present invention include water, methanol and ethanol.
以下结合技术方案详细叙述本发明的具体实施例。实施例列出了新型含蒽酮结构聚芳醚制备工艺，这些实例仅仅是为了对本发明进行说明，并不是限定本发明保护范围。Specific embodiments of the present invention will be described in detail below in conjunction with technical solutions. The examples list the preparation process of the novel polyarylether containing anthrone structure, and these examples are only for illustrating the present invention, and are not intended to limit the protection scope of the present invention.
实施例1Example 1
在氮气保护下，将37.8427 g (0.1mol) 蒽酮结构双酚单体，21.8203 g (0.1mol) 4,4’-二氟二苯甲酮，16.5744 g（0.14 mol）K2CO3，42 mL N-甲基吡咯烷酮和30 mL甲苯加入到装有机械搅拌器、温度计、分水器、氮气入口的三口烧瓶中，搅拌，加热升温反应，在140℃下，共沸脱水3h，体系水分被共沸脱水去除。然后蒸出甲苯，温度升温至160-200℃，继续反应18小时，反应体系粘度显著增大。反应结束后，加入N-甲基吡咯烷酮稀释反应溶液，将溶液倒入大量水中，聚合物沉淀析出，用去离子水煮洗5次，得到灰白色的含蒽酮结构聚芳醚酮。Under nitrogen protection, 37.8427 g (0.1 mol) bisphenol monomer with anthrone structure, 21.8203 g (0.1 mol) 4,4'-difluorobenzophenone, 16.5744 g (0.14 mol) K 2 CO 3 , 42 Add mL of N -methylpyrrolidone and 30 mL of toluene into a three-necked flask equipped with a mechanical stirrer, a thermometer, a water separator, and a nitrogen inlet, stir, and heat up to react. At 140°C, azeotropic dehydration is carried out for 3 hours, and the water in the system is eliminated. Azeotropic dehydration removed. Then the toluene was distilled off, the temperature was raised to 160-200° C., and the reaction was continued for 18 hours, and the viscosity of the reaction system increased significantly. After the reaction, add N -methylpyrrolidone to dilute the reaction solution, pour the solution into a large amount of water, the polymer precipitates out, wash with deionized water for 5 times, and obtain off-white polyaryletherketone containing anthrone structure.
实施例2Example 2
在氮气保护下，将37.8427g （0.1mol）蒽酮结构双酚单体， 28.7154g (0.1mol) 4,4’-二氯二苯砜，16.5744 g（0.14 mol）K2CO3，40 mL N-甲基吡咯烷酮和30 mL甲苯加入到装有机械搅拌器、温度计、分水器、氮气入口的三口烧瓶中，搅拌，加热升温反应，在140℃下，共沸脱水3h，体系水分被共沸脱水去除。然后蒸出甲苯，温度升温至160-200℃，继续反应24小时。反应体系为棕褐色，体系粘度显著增大。反应结束后，加入N-甲基吡咯烷酮稀释反应溶液，将溶液倒入大量水中，聚合物沉淀析出，用去离子水煮洗5次，得到含蒽酮结构聚芳醚砜。Under nitrogen protection, 37.8427g (0.1mol) anthrone structure bisphenol monomer, 28.7154g (0.1mol) 4,4'-dichlorodiphenylsulfone, 16.5744g (0.14mol) K 2 CO 3 , 40 mL Add N -methylpyrrolidone and 30 mL of toluene into a three-necked flask equipped with a mechanical stirrer, a thermometer, a water separator, and a nitrogen inlet, stir, and heat up to react. At 140 ° C, azeotropic dehydration is carried out for 3 hours. Boiling dehydration removed. Then the toluene was evaporated, the temperature was raised to 160-200° C., and the reaction was continued for 24 hours. The reaction system was brown, and the viscosity of the system increased significantly. After the reaction, add N -methylpyrrolidone to dilute the reaction solution, pour the solution into a large amount of water, the polymer precipitates out, wash with deionized water for 5 times, and obtain polyarylethersulfone containing anthrone structure.
以上对本发明的具体实施方式作了说明，但这些不能被理解为限制了本发明的保护的范围，本发明的保护范围由随附的权利要求书限定，任何在本发明权利要求基础上的改动都是本发明的保护范围。The specific embodiments of the present invention have been described above, but these can not be interpreted as limiting the scope of protection of the present invention, the scope of protection of the present invention is defined by the appended claims, any modification on the basis of the claims of the present invention All are protection scope of the present invention.
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