CN111434721A - 聚氨酯自修复薄膜及制备方法及自修复程度的检测方法 - Google Patents
聚氨酯自修复薄膜及制备方法及自修复程度的检测方法 Download PDFInfo
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- CN111434721A CN111434721A CN201910033124.2A CN201910033124A CN111434721A CN 111434721 A CN111434721 A CN 111434721A CN 201910033124 A CN201910033124 A CN 201910033124A CN 111434721 A CN111434721 A CN 111434721A
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Abstract
本发明公开了聚氨酯自修复薄膜及制备方法及自修复程度的检测方法,其检测方法为:聚氨酯自修复薄膜切成两片,再把切面对接到一起,在40℃‑50条件下,用汞灯加365nm滤光片的光照射30‑40min,得到修复,进行拉伸,用流变仪收集拉伸过程中的断裂应力‑应变数据,用相机拍摄拉伸过程中的发光照片,把断裂应力‑应变数据和发光照片进行比较,检测出聚氨酯自修复薄膜的自修复程度。本发明的聚氨酯自修复薄膜在一定条件下,可实现快速修复,修复过程简单快捷,可以用作室外薄膜。可以通过拉伸过程中的发光强度检测出自修复程度,相对于传统的用断裂应力检测自修复程度,这种方法更加直观,可用肉眼观测。
Description
技术领域
本发明属于功能聚合物复合材料领域,涉及一种利用机械力诱导发光检测聚氨酯薄膜自修复程度的方法。
背景技术
机械力响应聚合物,在机械力的作用下发生共价键的选择性断裂,释放出可视化信号,可以从微观分子水平研究宏观材料性能,把化学与力学领域相衔接,建立了实时灵敏的探测高分子材料损伤的新方法。目前,力诱导化学发光聚合物主要是基于双金刚烷取代的1,2-二氧环丁烷力响应基团合成的。基于双金刚烷取代的1,2-二氧环丁烷的力诱导发光聚合物在机械力作用下,含过氧键的四元环发生断裂产生420nm左右的蓝色化学发光。因此,力诱导化学发光是一种无需外源刺激、高灵敏地检测键断裂的方法。然而,目前的大多数研究是将力诱导发光用于聚合物的损伤探测,进一步的应用亟待探索。
自修复高分子材料,在合适的外部刺激下,断裂面可以发生修复,是一种新兴的智能材料,已成为当前研究的热点。然而,目前关于自修复高分子的研究主要集中在提高材料的修复程度,并通过断裂应力检测修复程度,但该检测方法不直观。
发明内容
本发明的目的是克服现有技术的不足,提供一种聚氨酯自修复薄膜。
本发明的第二个目的是提供一种聚氨酯自修复薄膜的制备方法。
本发明的第三个目的是提供一种聚氨酯自修复薄膜自修复程度的检测方法。
本发明的技术方案概述如下:
聚氨酯自修复薄膜的制备方法,包括如下步骤:
(1)惰性气体保护条件下,将异佛尔酮二异氰酸酯(I)溶于干燥的三氯甲烷中,加入二月桂酸二丁基锡和双金刚烷取代的1,2-二氧环丁烷(II),反应,得到淡黄色透明液体聚氨酯预聚物(III);
(2)惰性气体保护条件下,聚四氢呋喃650(IV)溶于三氯甲烷,加入淡黄色透明液体聚氨酯预聚物(III),65℃条件下反应2h后,加入2-羟乙基二硫化物(V)的三氯甲烷溶液,继续在65℃条件下反应3h,得到淡黄色粘稠溶液,倒入正己烷中沉降,抽滤后得到的白色块状固体为聚氨酯弹性体(VI),真空干燥;
反应方程式如下:
(3)按比例,将9-10mL三氯甲烷加入到500mg聚氨酯弹性体(VI)中,搅拌1-2h,加入5mg苯并噻二唑联二噻吩,搅拌30-40min,得到透明溶液;
(4)将所述透明溶液放入模具中,在30-40℃条件下,放置70-80h,放入真空烘箱,在50-60℃条件下真空干燥12-16h,得到聚氨酯自修复薄膜。
上述方法制备的聚氨酯自修复薄膜。
聚氨酯自修复薄膜自修复程度的检测方法,包括如下步骤:
把聚氨酯自修复薄膜切成两片,再把切面对接到一起,在40℃-50条件下,用汞灯加365nm滤光片的光照射30-40min,得到修复,进行拉伸,用流变仪收集拉伸过程中的断裂应力-应变数据,用相机拍摄拉伸过程中的发光照片,把断裂应力-应变数据和发光照片进行比较,检测出聚氨酯自修复薄膜的自修复程度。
本发明的优点:
本发明的聚氨酯自修复薄膜在40℃条件下,用汞灯的365nm光照时,可以实现快速修复,修复过程简单快捷,这种聚氨酯薄膜可以用作室外薄膜。可以通过拉伸过程中的发光强度检测出自修复程度,相对于传统的用断裂应力检测自修复程度,这种方法更加直观,可用肉眼观测。
附图说明
图1为实施例3步骤(2)得到的聚氨酯弹性体的核磁氢谱。
图2为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂应力-应变曲线。
图3为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂应力-应变修复程度曲线。
图4为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂发光强度的计算结果。
图5为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂发光强度的修复程度曲线。
具体实施方式
下面结合具体实施例对本发明作进一步的说明。
实施例1
双金刚烷取代的1,2-二氧环丁烷(端基双键)(化合物5)的合成
双金刚烷取代的1,2-二氧环丁烷(端基羟基)简称为:双金刚烷取代的1,2-二氧环丁烷。
(1)化合物1的合成:在冰水浴的条件下,30g三溴化磷缓慢滴入17g溴素和75mL正庚烷的混合物中,制备得到五溴化磷,再加入15g 2-金刚烷酮,搅拌回流3-5h至溶液澄清。混合物冷却至室温,倒入100mL冰水中,用乙酸乙酯萃取分离出有机相,用饱和亚硫酸氢钠水溶液和水洗涤,有机相用无水硫酸镁干燥后旋干,乙醇重结晶得到无色针状固体化合物1(18.83g,产率64%)。
(2)化合物2的合成:反应过程严格无水操作,反应瓶、回流管、恒压滴液漏斗在烘箱中干燥。将4g镁条剪碎加入反应瓶中并加入25mL干燥的四氢呋喃和一粒碘晶体。10g化合物1溶解在75mL干燥的四氢呋喃中,在惰氦气条件下缓慢滴入化合物1的四氢呋喃溶液的10%至反应瓶,微热至引发反应,剩余化合物1的溶液再继续滴入反应瓶中,加热回流5h。冷却反应溶液至室温,倒入100mL水中,用乙酸乙酯萃取分离出有机相,饱和食盐水洗,无水硫酸镁干燥有机相,旋干,无水甲醇洗,干燥,得到化合物2(3.16g,产率65%)。
(3)化合物3的合成:化合物2(3.8g)和溴代叔丁烷(1.83mL)放于反应瓶中,在冰水浴的条件下加入三溴化铝(18.13g),搅拌均匀,慢慢滴入溴素(4.35mL)。搅拌室温反应2天后,在混合物中加入20mL冰水,二氯甲烷萃取得到有机相,再用饱和碳酸氢钠水溶液和水洗涤有机相,无水硫酸镁干燥,旋干,得到棕褐色固体,用温乙醇洗,得到棕色固体粗产物3(6.02g,产率99%)。
(4)化合物4的合成:化合物3(2.0g,4.7mmol)溶于1,4-二氧六环(20mL),加入乙二醇(112mL,2mol)。在氦气条件下加入四氟硼酸银(4.0g,20.54mmol),85℃反应8h。冷却反应溶液至室温,加入20mL冷水和二氯甲烷萃取出有机相,水洗,无水硫酸镁干燥,旋干,硅胶层析柱分离得到棕色固体为化合物4(0.76g,产率41%)。
(5)化合物5的合成:在光照反应装置中,加入化合物4(0.3g,0.77mmol),60mL二氯甲烷和30mg亚甲基蓝,将氧气鼓泡至反应溶液中,高压钠灯照射5h,核磁氢谱监测反应完全后,活性炭吸附除去亚甲基蓝,过滤,滤液旋干,得到淡黄色油状化合物5(0.29g,产率89%)。
实施例2
苯并噻二唑联二噻吩(能量转移受体分子)的合成
将A(2g,6.8mmol)、B(3.57g,17mmol)、NaHCO3(5.72g,68mmol)、三(二亚苄基丙酮)二钯(0.31g,0.34mmol)、三(邻甲基苯基)膦(0.41g,1.36mmol)加入到四氢呋喃(80mL)和水(30mL)的混合溶液中,反复脱气,在在N2氛围下升温到90℃反应72h。将反应液冷却到室温,用三氯甲烷和饱和食盐水萃取,收集有机相,加入无水硫酸镁干燥,旋干溶剂。过硅胶柱,粗产物用二氯甲烷和石油醚混合溶剂重结晶,得到橙红色固体苯并噻二唑联二噻吩(1.2g,60%)。
实施例3
聚氨酯自修复薄膜的制备方法,其特征是包括如下步骤:
(1)氦气保护条件下,将异佛尔酮二异氰酸酯(I)(0.793g,3.57mmol)溶于3mL干燥的三氯甲烷中,加入二月桂酸二丁基锡5μL和双金刚烷取代的1,2-二氧环丁烷(II)(30mg,0.077mmol),30℃条件下反应1h,得到淡黄色透明液体聚氨酯预聚物(III);
(2)氦气保护条件下,聚四氢呋喃650(IV)(1.005g,1.55mmol)溶于4mL三氯甲烷,加入淡黄色透明液体聚氨酯预聚物(III),65℃条件下反应2h后,加入2-羟乙基二硫化物(V)(0.286g,1.86mmol)的三氯甲烷溶液3mL,继续在65℃条件下反应3h,得到淡黄色粘稠溶液,倒入正己烷中沉降,抽滤后得到的白色块状固体为聚氨酯弹性体(VI),真空干燥1-2天。图1为聚氨酯弹性体的核磁氢谱,2.89ppm处的峰表示双金刚烷取代的1,2-二氧环丁烷中与环丁烷上两个碳相连氢的峰,证明双金刚烷取代的1,2-二氧环丁烷已经成功接入聚氨酯弹性体。
反应方程式如下:
(3)将10mL(也可以选用9mL)三氯甲烷加入到500mg聚氨酯弹性体(VI)中,搅拌1h(也可以2h),加入5mg苯并噻二唑联二噻吩,搅拌30min(也可以是40min),得到透明溶液;
(4)将所述透明溶液放入模具中,在30℃(也可以是40℃)条件下,放置70h(也可以是80h),放入真空烘箱,在50℃(也可以是60℃)条件下真空干燥12h(也可以是16h),得到聚氨酯自修复薄膜。
实施例4
聚氨酯自修复薄膜自修复程度的检测方法,包括如下步骤:
用刀片把聚氨酯自修复薄膜切成两片,再把切面对接到一起,在40℃(也可以是50℃)条件下,用汞灯加365nm滤光片的光照射30min(也可以是40min),得到修复,进行拉伸,用流变仪收集拉伸过程中的断裂应力-应变数据,用相机拍摄拉伸过程中的发光照片,把断裂应力-应变数据和发光照片进行比较,检测出聚氨酯自修复薄膜的自修复程度。
图2为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂应力-应变曲线。
图3为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂应力-应变修复程度曲线。可以发现,薄膜在修复15min后,断裂应力修复55%。薄膜在修复30min后,断裂应力可以修复100%。
图4为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂发光强度的计算结果。
图5为实施例4得到的聚氨酯自修复薄膜的不同修复时间对应的断裂发光强度的修复程度曲线。可以发现,薄膜在修复修复15min后,发光强度修复29%。薄膜在修复30min后,断裂应力可以修复94%。
把图3和图5的数据进行对比,可以发现,当薄膜的断裂应力修复55%时,发光强度仅能修复29%,当薄膜的断裂应力修复100%时,发光强度可以修复到94%。说明,当薄膜的断裂应力修复程度越高时,发光强度的修复程度越接近应力的修复。这是由于,当薄膜修复程度高时,越多被切断的分子链重新连接到一起,机械力在分子链内的传导越流畅,分子链中的双金刚烷取代的1,2-二氧环丁烷在力的作用下断裂的数目越多,所以薄膜在断裂时发光越强。
Claims (3)
1.聚氨酯自修复薄膜的制备方法,其特征是包括如下步骤:
(1)惰性气体保护条件下,将异佛尔酮二异氰酸酯(I)溶于干燥的三氯甲烷中,加入二月桂酸二丁基锡和双金刚烷取代的1,2-二氧环丁烷(II),反应,得到淡黄色透明液体聚氨酯预聚物(III);
(2)惰性气体保护条件下,聚四氢呋喃650(IV)溶于三氯甲烷,加入淡黄色透明液体聚氨酯预聚物(III),65℃条件下反应2h后,加入2-羟乙基二硫化物(V)的三氯甲烷溶液,继续在65℃条件下反应3h,得到淡黄色粘稠溶液,倒入正己烷中沉降,抽滤后得到的白色块状固体为聚氨酯弹性体(VI),真空干燥;
反应方程式如下:
(3)按比例,将9-10mL三氯甲烷加入到500mg聚氨酯弹性体(VI)中,搅拌1-2h,加入5mg苯并噻二唑联二噻吩,搅拌30-40min,得到透明溶液;
(4)将所述透明溶液放入模具中,在30-40℃条件下,放置70-80h,放入真空烘箱,在50-60℃条件下真空干燥12-16h,得到聚氨酯自修复薄膜。
2.权利要求1的方法制备的聚氨酯自修复薄膜。
3.聚氨酯自修复薄膜自修复程度的检测方法,其特征是包括如下步骤:
把权利要求2的聚氨酯自修复薄膜切成两片,再把切面对接到一起,在40℃-50条件下,用汞灯加365nm滤光片的光照射30-40min,得到修复,进行拉伸,用流变仪收集拉伸过程中的断裂应力-应变数据,用相机拍摄拉伸过程中的发光照片,把断裂应力-应变数据和发光照片进行比较,检测出聚氨酯自修复薄膜的自修复程度。
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