CN109503884A - 一种色胺类阻燃剂及其合成和应用 - Google Patents
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Abstract
本发明公开的一种色胺类阻燃剂及其合成与应用，包括一种化合物A，其化学结构式为：，将化合物A作为阻燃剂运用于增加环氧树脂的阻燃属性中，阻燃效果好，固化效果好，合成过程副反应少，产率高。
Description
技术领域
本发明涉及环氧树脂材料领域，具体涉及一种色胺类阻燃剂及其合成与应用。
背景技术
环氧树脂(EP)又称作人工树脂、人造树脂、树胶等。是一类重要的热固性塑料，因其具有良好的粘结性、电绝缘性、化学稳定性，广泛应用于涂料、粘胶剂、电子电器材料、工程塑料和复合材料、土建材料等领域。但环氧树脂极限氧指数非常低，极易燃烧，失火后持续燃烧且发烟量大。其易燃性限制了它在许多领域的应用。 因此，赋予EP良好的阻燃性是至关重要的。
为了提高环氧树脂的阻燃性能，常见的方法是添加阻燃剂。传统的含卤阻燃材料燃烧时存在多烟、有毒气体放出等二次伤害，对人身安全构成严重威胁，因此设计新型无卤阻燃剂显得尤为重要。
因此，急需合成一种，阻燃效率高、副反应少的无卤阻燃剂。
发明内容
为解决上述问题，本发明提供一种色胺类阻燃剂及其合成与应用，该阻燃剂阻燃效果好，合成过程副反应少，固化效果好，产率高。
本发明解决的技术方案是，提供一种色胺类阻燃剂，所述色胺类阻燃剂包括化合物A，化学结构式如下：
同时，还提供一种色胺类阻燃剂的合成方法，其特征在于，包括以下步骤：
（1）以醇为溶剂，在氮气的保护下，色胺与水杨醛发生缩合反应，合成中间产物；
（2）以醇为溶剂，所述中间产物与DOPO进行加成反应，得到化合物A。
优选地，所述反应物色胺、水杨醛、DOPO的摩尔比为1:1:1。
优选地，所述步骤（1）、步骤（2）的反应温度为50-65℃。
优选地，所述步骤（1）的反应时间为3-5h。
优选地，所述步骤（2）的反应时间为2-4h。
优选地，所述步骤（1）的醇溶剂为乙醇。
还提供一种色胺类阻燃剂的应用方法，其特征在于，将环氧树脂、所述色胺类阻燃剂、固化剂在90~100℃下混匀，抽真空后加入固化剂并倒入模具，冷却成模，并在100~150℃下固化2~4h，即得环氧树脂固化物。
优选地，所述色胺类阻燃剂为化合物A。
优选地，所述环氧树脂与所述色胺类阻燃剂的物料比为100:10~15.7。
值得注意的是，本发明所述的色胺类阻燃剂具体合成步骤如下：在氮气的保护下，将色胺和水杨醛以比为1：1的比例溶解于乙醇，在50~65℃磁力搅拌3-5h，并冷凝回流；将所得到的溶液冷却并进行抽滤，将抽滤锁得产物用乙醇洗涤，并置于真空干燥箱干燥10-12h，得到黄色固体，即为中间产物；将中间产物溶解于乙醇中，缓慢滴加与色胺摩尔比为1：1的DOPO，50-65℃下磁力搅拌2-4h，将所得沉淀进行抽滤，并用乙醇水溶液洗涤，置于真空干燥箱干燥10-12h，得到白色固体，即所述化合物A，以下以DHABP阻燃剂代替。
值得注意的是，DOPO类阻燃剂因具有无卤低毒、适合生产加工、对机械性能影响小、不腐蚀模具、阻燃性能良好等特性，而色胺中含有伯胺及仲胺，与DOPO反应形成的衍生物具有氮磷的协同作用，可以促进DOPO的阻燃效果，此外色胺还有促进固化的作用。原因是分子中的P在燃烧时会产生含磷自由基，具有气相阻燃性能，而氮元素的引入可在高温燃烧时释放一些含氮不可燃气体稀释了可燃气体有延缓燃烧的作用。此外色胺残基上的活泼氢，可以与环氧树脂的环氧基团作用，使之交联固化，从而起到促进固化的作用。
与现有技术相比，本发明所制备的色胺类阻燃剂，可做为添加剂加入到环氧树脂中，提高其阻燃性，且阻燃效率高，合成过程副反应少，固化效果好，产率高。
附图说明
图1为本发明色胺类阻燃剂的反应式；
图2为实施例1色胺类阻燃剂的核磁氢谱谱图；
图3为实施例1色胺类阻燃剂的核磁磷谱谱图。
具体实施方式
以下是本发明的具体实施例并结合附图，对本发明的技术方案作进一步的描述，但本发明并不限于这些实施例。
实施例1
色胺类阻燃剂的制备方法：
1）准确称取16 g（0.1mol）色胺加入到装有40 ml乙醇于250 ml三口圆底烧瓶中，用恒压漏斗向其中缓慢滴加含有12.2g (0.1mol ) 水杨醛的10 ml乙醇溶液，在室温下磁力搅拌反应，1 h后出现灰白色沉淀，4 h后终止反应；
2）将所得到的溶液冷却进行过滤，并用乙醇进行洗涤（理论产量0.1mol），然后将其溶解于80.0 ml 乙醇中，再加入9，10-二氢-9-氧杂-10-磷杂菲-10-氧化物（0.1mol，21.6 g），搅拌溶液3 h，得到白色沉淀；
3）将上步反应所得沉淀进行过滤，用乙醇和水的混合物进行洗涤，在65℃下真空干燥12 h，称量，产率为95.34%，将产品放置在干燥器中保存。
由图2可知，化学位移在6.8-8.3ppm的峰可归属于芳环上的氢原子，包括苯环上的氢及色胺残基上的氢。3.1ppm 及3.9ppm分别是色胺残基上两个亚甲基的化学位移。2.0ppm可归属于仲胺的氢的化学位移，且其峰面积与对应氢原子个数大致吻合，说明合成成功。
由图3可知，磷谱图中只出现了两个化学位移相隔较近的两个峰， 分别位于32.7ppm 和 29.6 ppm，这可归属于一种磷原子，这种现象是由于手性碳的原因而产生的，这在其它的含DOPO的阻燃材料中也有报道，说明合成成功。
实施例2
色胺类阻燃剂的效果测试
称取100.00 g环氧树脂和10g 色胺化合物,在90℃下磁力搅拌均匀，抽真空10 min，然后加入15.00 g DDM固化剂，5 min内将混合物倒入模具中，冷却，制样，阻燃剂添加量8%，含磷量为0.52%，氧指数测试结果为30.0，垂直燃烧实验结果为V1 级别。
值得说明的是，实施例中分别用JF-3型氧指数测定仪进行氧指数（LOI）测试，FZ-5401型垂直燃烧仪进行UL94垂直燃烧性能测试。
实施例3
色胺类阻燃剂的效果测试
称取100.00 g环氧树脂和12.80 g 色胺化合物,在90℃下磁力搅拌均匀，抽真空10min，然后加入15.00 g DDM固化剂，5 min内将混合物倒入模具中，冷却，制样，阻燃剂添加量10%，含磷量为0.64%，氧指数测试结果为34.0，垂直燃烧实验结果为V0 级别。
值得说明的是，实施例中分别用JF-3型氧指数测定仪进行氧指数（LOI）测试，FZ-5401型垂直燃烧仪进行UL94垂直燃烧性能测试。
实施例4
称取100.00 g环氧树脂和15.7 g DHABP化合物,在90℃下磁力搅拌均匀，抽真空10min，然后加入15.00 g DDM固化剂，5 min内将混合物倒入模具中，冷却，制样，阻燃剂添加量12%，含磷量为0.77%，最后氧指数测试结果为34.5，垂直燃烧实验结果为V0 级别。
值得说明的是，实施例中分别用JF-3型氧指数测定仪进行氧指数（LOI）测试，FZ-5401型垂直燃烧仪进行UL94垂直燃烧性能测试。
实施例5
称取100.00 g环氧树脂，在90℃下磁力搅拌均匀，抽真空10 min，然后加入15.00 gDDM固化剂，5 min内将混合物倒入模具中，冷却，制样，阻燃剂添加量0%，含磷量为0%，最后氧指数测试结果为25.5。垂直燃烧实验结果为NR级别。
以上未涉及之处，均适用于现有技术。
本文中所描述的具体实施例仅仅是对本发明精神作举例说明。本发明所属技术领域的技术人员可以对所描述的具体实施例做各种各样的修改或补充或采用类似的方式替代，但并不会偏离本发明的精神或者超越所附权利要求书所定义的范围。
Claims (10)
1.一种色胺类阻燃剂，其特征在于，所述色胺类阻燃剂包括化合物A，化学结构式如下：
。
2.一种色胺类阻燃剂的合成方法，其特征在于，包括以下步骤：
以醇为溶剂，在氮气的保护下，色胺与水杨醛发生缩合反应，合成中间产物；
以醇为溶剂，所述中间产物与DOPO进行加成反应，得到化合物A。
3.根据权利要求2所述的一种色胺类阻燃剂的合成方法，其特征在于，所述反应物色胺、水杨醛、DOPO的摩尔比为1:1:1。
4.根据权利要求2所述的一种色胺类阻燃剂的合成方法，其特征在于，所述步骤（1）、步骤（2）的反应温度为50-65℃。
5.根据权利要求2所述的一种色胺类阻燃剂的合成方法，其特征在于，所述步骤（1）的反应时间为3-5h。
6.根据权利要求2所述的一种色胺类阻燃剂的合成方法，其特征在于，所述步骤（2）的反应时间为2-4h。
7.根据权利要求2所述的一种色胺类阻燃剂的合成方法，其特征在于，所述步骤（1）的醇溶剂为乙醇。
8.一种色胺类阻燃剂的应用方法，其特征在于，将环氧树脂、所述色胺类阻燃剂、固化剂在90~100℃下混匀，抽真空后加入固化剂并倒入模具，冷却成模，并在100~150℃下固化2~4h，即得环氧树脂固化物。
9.根据权利要求8所述的一种色胺类阻燃剂的应用方法，其特征在于所述色胺类阻燃剂为化合物A。
10.根据权利要求8所述的一种色胺类阻燃剂的应用方法，其特征在于所述环氧树脂与所述色胺类阻燃剂的物料比为100:10~15.7。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912650A (zh) * | 2019-04-16 | 2019-06-21 | 中国科学院宁波材料技术与工程研究所 | 一种磷-氮系生物基阻燃剂及其合成方法和应用 |
| CN110734462A (zh) * | 2019-09-14 | 2020-01-31 | 武汉工程大学 | 一种含苯并咪唑结构的氮-磷系高效阻燃剂的合成及应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH402860A (de) * | 1960-02-24 | 1965-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer basischer Indol-Derivate |
| CN101538283A (zh) * | 2008-01-21 | 2009-09-23 | 长春人造树脂厂股份有限公司 | 磷系苯并恶嗪化合物及其制备方法 |
| CN102391545A (zh) * | 2011-08-05 | 2012-03-28 | 清华大学深圳研究生院 | 含氮磷的阻燃剂及其制备方法与应用 |
| CN103059339A (zh) * | 2012-12-21 | 2013-04-24 | 清华大学深圳研究生院 | 一种dopo基磷氮阻燃剂及其制备方法与应用 |
| CN103751943A (zh) * | 2014-01-13 | 2014-04-30 | 西安坚瑞安全应急设备有限责任公司 | 一种含有含氮类有机化合物的灭火组合物 |
| US20140296452A1 (en) * | 2013-03-28 | 2014-10-02 | Nan Ya Plastics Corporation | Halogen-free, nonflammable and high glass transition temperature phenolic resin-based curing agent and process for producing the same |
-
2018
- 2018-11-20 CN CN201811382474.1A patent/CN109503884B/zh active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH402860A (de) * | 1960-02-24 | 1965-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer basischer Indol-Derivate |
| CN101538283A (zh) * | 2008-01-21 | 2009-09-23 | 长春人造树脂厂股份有限公司 | 磷系苯并恶嗪化合物及其制备方法 |
| CN102391545A (zh) * | 2011-08-05 | 2012-03-28 | 清华大学深圳研究生院 | 含氮磷的阻燃剂及其制备方法与应用 |
| CN103059339A (zh) * | 2012-12-21 | 2013-04-24 | 清华大学深圳研究生院 | 一种dopo基磷氮阻燃剂及其制备方法与应用 |
| US20140296452A1 (en) * | 2013-03-28 | 2014-10-02 | Nan Ya Plastics Corporation | Halogen-free, nonflammable and high glass transition temperature phenolic resin-based curing agent and process for producing the same |
| CN103751943A (zh) * | 2014-01-13 | 2014-04-30 | 西安坚瑞安全应急设备有限责任公司 | 一种含有含氮类有机化合物的灭火组合物 |
Non-Patent Citations (2)
| Title |
|---|
| NEMA HAFEZI: "Adaptation of dynamic covalent systems of imine constituents to medium change by component redistribution under reversible phase separation", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| RONGKUN JIAN: "Effect of a novel P/N/S-containing reactive flame retardant on curing behavior, thermal and flame-retardant properties of epoxy resin", 《 JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912650A (zh) * | 2019-04-16 | 2019-06-21 | 中国科学院宁波材料技术与工程研究所 | 一种磷-氮系生物基阻燃剂及其合成方法和应用 |
| CN109912650B (zh) * | 2019-04-16 | 2022-12-13 | 中国科学院宁波材料技术与工程研究所 | 一种磷-氮系生物基阻燃剂及其合成方法和应用 |
| CN110734462A (zh) * | 2019-09-14 | 2020-01-31 | 武汉工程大学 | 一种含苯并咪唑结构的氮-磷系高效阻燃剂的合成及应用 |
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