CN115286621A - 一种全生物基苯并噁嗪树脂及其制备方法 - Google Patents
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Abstract
本发明属于材料技术领域，具体涉及一种全生物基苯并噁嗪树脂及其制备方法；包含以下步骤：将辣椒素作为酚源，将糠胺作为胺源与醛类化合物在有机溶剂中混合，于40~90℃反应4~8h，经纯化处理得到全生物基苯并噁嗪单体；将所述苯并噁嗪单体在130~220℃固化反应4~12h得到聚苯并噁嗪。辣椒素作为一种生物基原料有抗氧化、抗菌的作用。本发明制备的树脂首次将生物基辣椒素引入到苯并噁嗪树脂中。本发明树脂的原料易得、成本较低、操作过程简单、对环境友好，有望应用到抗菌涂层中，实现工业化生产。
Description
技术领域
本发明属于材料技术领域，具体涉及一种全生物基苯并噁嗪树脂及其制备方法。
背景技术
当前石油资源逐渐枯竭，原油的价格也不断上涨，环境问题非常突出。苯并噁嗪树脂是由胺类化合物、酚类化合物以及醛类化合物经Mannich反应合成的一类六元杂环化合物，随后经高温固化得到苯并噁嗪聚合物。由于苯并噁嗪具有一系列的优点，例如灵活的分子设计性、固化过程中无小分子放出、固化物热稳定性好以及阻燃性能优异等，已经在航天航空、涂料、电子电器等领域得到大量应用。最关键的就在于其灵活的分子设计性，可以在其原料胺类化合物、酚类化合物、醛类化合物上做出改变，使用一些天然来源的原料，以达到生物环保的目的。
辣椒物种（茄科植物）是辛辣类辣椒素的来源，辣椒素由香草醛和支链脂肪酸融合而成。辣椒物种传统上用作香料并缓解疼痛状况，因此大多应用于医药领域。此外，辣椒提取物除了抗氧化、抑制血小板聚集和抗肥胖作用外，据报道，辣椒提取物对各种细菌活性有抑制作用，例如芽孢杆菌、梭状芽孢杆菌、大肠杆菌、沙门氏菌等。因此，将辣椒素作为酚源引入到苯并噁嗪中，再将生物质原料糠胺作为胺源，有望制备一种抗氧化并且具有抗菌性的苯并噁嗪。
发明内容
本发明克服现有技术的不足，提供一种全生物基苯并噁嗪树脂及其制备方法，从分子角度入手增加苯并噁嗪的抗氧化性，同时增加一定的抗菌性。
为解决上述技术问题，本发明所采用的技术方案为：
一种全生物基苯并噁嗪单体，其结构式为：
一种聚苯并噁嗪，其特征在于，其结构式为：
上述的一种全生物基苯并噁嗪单体的制备方法为，将辣椒素作为酚源，糠胺作为胺源，与醛类化合物在有机溶剂中混合，于40~90℃反应4~8h，经纯化处理得到全生物基苯并噁嗪单体；反应方程式如下：
进一步的，所述多聚甲醛、辣椒素、糠胺摩尔比为2:1:1。
进一步的，所述的有机溶剂的量为每0.1mol的醛类化合物加入15ml有机溶剂；所述的有机溶剂为丙酮、氯仿和二氧六环中的一种。
进一步的，全生物基苯并噁嗪单体优化的制备方法，具体步骤为：醛类化合物和糠胺在有机溶剂中混合，于40~90℃反应反应1~4h；将辣椒素与有机溶剂混合充分溶解；再将溶解完全的辣椒素溶液加入反应液中，于40~90℃反应2~5h；将反应液倒入氢氧化钠溶液中沉淀，得到乳白色悬浊液，静置后除去上层清液得到白色沉淀，随后倒入去离子水中再次静置分层，最后将白色沉淀物干燥后研磨得到全生物基苯并噁嗪单体。
进一步的，所述醛类化合物为甲醛或多聚甲醛。
上述的全生物基聚苯并噁嗪的制备方法为，将所述全生物基苯并噁嗪单体放置于干燥箱中，设置温度梯度进行固化，冷却后即得全生物基聚苯并噁嗪热固性树脂。
进一步的，所述的温度梯度固化条件为：130℃保持1~2h，150℃保持1~2h，170℃保持1~2h，190℃保持1~2h，210℃保持1~2h。
本发明还提供上述的一种全生物基聚苯并噁嗪在抗菌涂层中的应用。
与现有技术相比本发明具有以下有益效果：
本发明制备的树脂将生物质原料辣椒素引入到苯并噁嗪中，增加了苯并噁嗪树脂的抗氧化性，同时增加了抗菌性。
本发明制备工艺简单，原料天然易得且成本低，最关键的是对环境友好。溶剂可以多种选择、优化了制备工艺，易于实现工业化生产。
附图说明
图1为本发明实施例1的全生物基苯并噁嗪单体的核磁共振氢谱图。
图2为本发明实施例1的全生物基苯并噁嗪单体的红外光谱图。
图3为本发明实施例2的全生物基聚苯并噁嗪的TGA曲线图。
具体实施方式
以下结合具体实施例对本发明作进一步说明。
实施例1
全生物基苯并噁嗪单体的制备：将多聚甲醛1.3g(0.04mol)和1.94g糠胺(0.02mol)溶于15ml有机溶剂中，随后将充分溶解于15ml有机溶剂的5.86g辣椒素(0.02mol)逐滴加入到多聚甲醛与糠胺的混合液中，在80℃通入氮气搅拌2~5h，分离有机溶剂和水，干燥有机相得到产物全生物基苯并噁嗪单体。核磁共振氢谱图见图1。
图1中在4.96ppm和3.98ppm的单峰分别对应苯并噁嗪的噁嗪环结构中Ar-CH2-N和O-CH2-N中的H原子，说明产物中存在苯并噁嗪环状结构。3.93ppm是靠近呋喃环上N-CH2-C上的H原子，5.69~6.69ppm上的5个峰对应呋喃环上的H以及靠近噁嗪环边苯环上的H，0~2ppm上的峰是全生物基苯并噁嗪左侧甲基与亚甲基上的H原子，该全生物基苯并噁嗪被成功合成。
所制得的化合物红外光谱图见图2。
图2中1640cm-1为苯环骨架振动吸收峰，1220cm-1处为噁嗪环上C-N-C的吸收峰，1020cm-1处为噁嗪环上C-O的对称伸缩振动峰，935cm-1处为噁嗪环的特征吸收峰。由红外谱图可以基本确定由辣椒素作为酚源的全生物基苯并噁嗪单体的结构特征。
实施例2
聚苯并噁嗪的制备：取一定量的苯并噁嗪单体平铺于培养皿中，后放置于鼓风干燥箱中，设置温度梯度为130℃/1~2h、150℃/1~2h、170℃/1~2h、190℃/1~2h、210℃/1~2h进行固化，冷却后即得聚苯并噁嗪热固性树脂。所制得的树脂的TGA曲线见图3。由图3可以看出，全生物基辣椒素苯并噁嗪失重5%的温度T5%为304.1℃，失重10%的温度T10%为321.3℃，800℃时的残碳率为43.4%。
Claims (10)
1.一种全生物基苯并噁嗪单体，其特征在于，其结构式为：
2.一种全生物基聚苯并噁嗪，其特征在于，其结构式为：
3.根据权利要求1所述的一种全生物基苯并噁嗪单体的制备方法，其特征在于，将辣椒素作为酚源，糠胺作为胺源，与醛类化合物在有机溶剂中混合，于40~90℃反应4~8h，经纯化处理得到全生物基苯并噁嗪单体；反应方程式如下：
4.根据权利要求3所述的一种全生物基苯并噁嗪单体的制备方法，其特征在于，所述多聚甲醛、辣椒素、糠胺摩尔比为2:1:1。
5.根据权利要求3所述的一种全生物基苯并噁嗪单体的制备方法，其特征在于，所述的有机溶剂的量为每0.1mol的醛类化合物加入15ml有机溶剂；所述的有机溶剂为丙酮、氯仿和二氧六环中的一种。
6.根据权利要求3所述的一种全生物基苯并噁嗪单体的制备方法，其特征在于，具体步骤为：醛类化合物和糠胺在有机溶剂中混合，于40~90℃反应反应1~4h；将辣椒素与有机溶剂混合充分溶解；再将溶解完全的辣椒素溶液加入反应液中，于40~90℃反应2~5h；将反应液倒入氢氧化钠溶液中沉淀，得到乳白色悬浊液，静置后除去上层清液得到白色沉淀，随后倒入去离子水中再次静置分层，最后将白色沉淀物干燥后研磨得到全生物基苯并噁嗪单体。
7.根据权利要求3所述的一种全生物基苯并噁嗪单体的制备方法，其特征在于，所述醛类化合物为甲醛或多聚甲醛。
8.根据权利要求2所述的一种全生物基聚苯并噁嗪的制备方法，其特征在于，将所述全生物基苯并噁嗪单体放置于干燥箱中，设置温度梯度进行固化，冷却后即得全生物基聚苯并噁嗪热固性树脂。
9.根据权利要求8所述的一种全生物基聚苯并噁嗪的制备方法，其特征在于，所述的温度梯度固化条件为：130℃保持1~2h，150℃保持1~2h，170℃保持1~2h，190℃保持1~2h，210℃保持1~2h。
10.如权利要求2所述的一种全生物基聚苯并噁嗪在抗菌涂层中的应用。
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| US8026235B1 (en) * | 2010-10-13 | 2011-09-27 | Daewoong Pharmaceutical Co., Ltd. | Pyridyl benzoxazine derivatives, pharmaceutical composition comprising the same, and use thereof |
| CN111205420A (zh) * | 2020-03-16 | 2020-05-29 | 淮北绿洲新材料有限责任公司 | 一种全生物基苯并噁嗪树脂及其制备方法 |
| CN113801283A (zh) * | 2021-07-23 | 2021-12-17 | 中北大学 | 高耐热高残碳苯并噁嗪树脂及其制备方法 |
| CN114031616A (zh) * | 2021-12-14 | 2022-02-11 | 中北大学 | 一种高残碳含乙酸乙酯及***环结构的苯并噁嗪及其制备方法 |
| CN114805717A (zh) * | 2022-03-22 | 2022-07-29 | 华南理工大学 | 一种辣椒素酚醛树脂及其制备与应用 |
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| US8026235B1 (en) * | 2010-10-13 | 2011-09-27 | Daewoong Pharmaceutical Co., Ltd. | Pyridyl benzoxazine derivatives, pharmaceutical composition comprising the same, and use thereof |
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| CN113801283A (zh) * | 2021-07-23 | 2021-12-17 | 中北大学 | 高耐热高残碳苯并噁嗪树脂及其制备方法 |
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