CN116332840A - 双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂及其制备方法 - Google Patents
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 9
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Abstract
本发明公开了一种双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂及其制备方法。所述的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂的制备方法是：以3‑氨基吡啶为起始原料，与草酰氯反应得到N，N'‑二(3‑吡啶基)乙二酰胺，再与溴代烷烃反应制得双酰胺类吡啶季铵盐。本发明提供的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，原料易得，制备简单，而且易降解，绿色环保。将其用于水性涂料，有比较优异的闪锈抑制性和缓蚀性能，且热储存稳定性好，配方适应性良好。
Description
技术领域
本发明属于缓蚀剂技术领域，具体涉及一种双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂及其制备方法和应用。
背景技术
涂料缓蚀剂是一种能够明显提高涂层防腐能力的化合物。最早使用的缓蚀剂是铬酸盐、亚硝酸盐、磷酸盐等无机盐，由于无机缓蚀剂用量较大，导致投入成本高、对环境破坏严重，逐步被有机缓蚀剂替代。有机缓蚀剂包括植物提取绿色缓蚀剂、氨基酸缓蚀剂、含氮杂环缓蚀剂等，具有用量少、缓蚀性能好、适应范围广等优点，备受行业青睐。现有涂料缓蚀剂存在种类单一、持续效果短、对涂层选择性强、缓蚀机理不明确等问题，严重限制了涂料缓蚀剂的推广应用。随着环保政策的出台和水性涂料的发展，对涂料缓蚀剂提出了更高的要求，因此，开发绿色环保、能在水性涂料中应用的有机缓蚀剂一直是该领域的研究热点。
发明内容
本发明的目的在于提供一种双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂及其制备方法和应用，所述防腐缓蚀剂的制备方法简单、绿色环保。
本发明提供的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，结构中含有酰胺、吡啶和季铵盐不同类型有机缓蚀剂的特征，使用时可达到“1+1≥2”的协同效果。
本发明提供的一种双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，它是乙二酰胺桥联的吡啶季铵盐，具有如下结构式：
其中R代表碳数为8、10、12、14的长链烷烃。
本发明提供了上述双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂的制备方法，是以3-氨基吡啶为起始原料，与草酰氯反应得到N，N'-二(3-吡啶基)乙二酰胺，再与溴代烷烃反应制得乙二酰胺桥联的吡啶季铵盐，其制备过程的反应式如下：
本发明的制备方法，步骤如下：
(1)制备N，N'-二(3-吡啶基)乙二酰胺：将3-氨基吡啶和等摩尔量的三乙胺加入反应瓶中，再加入体积为三乙胺10～15倍量的溶剂二氯甲烷，然后滴加摩尔量为3-氨基吡啶0.4～0.5倍量的草酰氯，加完后室温搅拌反应7～10小时，抽滤，用水洗涤得N，N'-二(3-吡啶基)乙二酰胺；
(2)将N，N'-二(3-吡啶基)乙二酰胺和25～35倍摩尔量的溴代烷烃加入反应瓶中，加热到130～150℃反应25～35小时，冷却，抽滤，用乙酸乙酯洗涤得乙二酰胺桥联的吡啶季铵盐。
本发明提供了双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂用于水性涂料的闪锈抑制性和缓蚀效果评价：在水性醇酸防锈漆中添加0.5％的双酰胺类吡啶季铵盐防腐缓蚀剂，与空白对照组比较，有比较优异的闪锈抑制性和缓蚀性能，而且在热储存稳定性和空白对照组无差异，配方适应性良好。
与现有技术相比本发明的有益效果：
(1)本发明提供的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，原料易得，制备简单，而且易降解，绿色环保。
(2)本发明提供的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，结构中含有酰胺、吡啶和季铵盐不同类型有机缓蚀剂的特征，使用时可达到“1+1≥2”的协同效果。
(3)本发明提供的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂用于水性涂料时，具有用量少、闪锈抑制性和缓蚀性能好的特点。
附图说明
图1为溴化N，N'-二(1-正十二烷基-3-吡啶基)乙二酰胺双季铵盐的核磁氢谱图。
图2为溴化N，N'-二(1-正十二烷基-3-吡啶基)乙二酰胺双季铵盐的核磁碳谱图。
具体实施方式
下面通过实施例来进一步说明本发明，但不局限于以下实施例。
实施例1：溴化N，N'-二(1-正辛烷基-3-吡啶基)乙二酰胺双季铵盐(BPOB-8)的制备
(1)制备N，N'-二(3-吡啶基)乙二酰胺：在反应瓶中，加入3-氨基吡啶(5.94g，63mmol)、三乙胺(8.8mL，63mmol)和100mL二氯甲烷，开动搅拌，然后滴加草酰氯(2.6mL，30mmol)，加完后室温搅拌反应7小时，抽滤，用水洗涤，干燥得5.25g N，N'-二(3-吡啶基)乙二酰胺，产率72％，熔点：183.2-184.7℃。1H NMR(600MHz,DMSO-d6,ppm)δ:11.17(s,2H),9.05(s,2H),8.38(s,2H),8.24(s,2H),7.44(s,2H).13C NMR(150MHz,DMSO-d6,ppm):159.15,145.93,142.73,134.82,128.05,124.11.
(2)在反应瓶中，加入N，N'-二(3-吡啶基)乙二酰胺(1.45g，6mmol)和溴代正辛烷(34.77g，180mmol)，加热到140℃反应30小时，冷却，抽滤，用乙酸乙酯洗涤，干燥得3.12g溴化N，N'-二(1-正辛烷基-3-吡啶基)乙二酰胺双季铵盐，产率83％，熔点：205.5-206.3℃。1HNMR(600MHz,DMSO-d6,ppm)δ:11.95(s,2H),9.44(s,2H),8.96(d,J＝5.9Hz,2H),8.90(d,J＝8.7Hz,2H),8.25-8.18(m,2H),4.68(s,4H),1.92(s,4H),1.27(m,20H),0.85(t,J＝6.9Hz,6H).13C NMR(150MHz,DMSO-d6,ppm)δ:158.82,141.18,138.13,136.99,136.25,128.82,61.95,31.59,30.99,28.85,28.81,25.77,22.48,14.38.
实施例2：溴化N，N'-二(1-正癸烷基-3-吡啶基)乙二酰胺双季铵盐(BPOB-10)的制备
(1)制备N，N'-二(3-吡啶基)乙二酰胺同实施例1；
(2)在反应瓶中，加入N，N'-二(3-吡啶基)乙二酰胺(1.45g，6mmol)和溴代正癸烷(33.17g，150mmol)，加热到135℃反应35小时，冷却，抽滤，用乙酸乙酯洗涤，干燥得3.52g溴化N，N'-二(1-正癸烷基-3-吡啶基)乙二酰胺双季铵盐，产率85％，熔点：208.4-209.6℃。1HNMR(600MHz,DMSO-d6,ppm)δ:11.95(s,2H),9.44(s,2H),8.96(d,J＝5.4Hz,2H),8.90(d,J＝8.5Hz,2H),8.22(s,2H),4.69(s,4H),1.93(s,4H),1.27(m,28H),0.86(s,6H).13C NMR(150MHz,DMSO-d6,ppm)δ:158.81,141.19,138.10,136.96,136.20,128.83,61.90,31.74,30.87,29.34,29.22,29.12,28.87,25.76,22.56,14.43.
实施例3：溴化N，N'-二(1-正十二烷基-3-吡啶基)乙二酰胺双季铵盐(BPOB-12)的制备
(1)制备N，N'-二(3-吡啶基)乙二酰胺同实施例1；
(2)在反应瓶中，加入N，N'-二(3-吡啶基)乙二酰胺(1.45g，6mmol)和溴代正十二烷(44.86g，180mmol)，加热到140℃反应32小时，冷却，抽滤，用乙酸乙酯洗涤，干燥得3.81g溴化N，N'-二(1-正十二烷基-3-吡啶基)乙二酰胺双季铵盐，产率86％，熔点：210.7-211.3℃。1H NMR(600MHz,DMSO-d6,ppm)δ:11.96(s,2H),9.44(s,2H),8.96(d,J＝5.9Hz,2H),8.91(d,J＝8.7Hz,2H),8.23(s,2H),4.68(s,4H),1.94(s,4H),1.27(m,36H),0.85(s,6H).13CNMR(150MHz,DMSO-d6,ppm)δ:158.83,141.19,138.15,136.96,136.03,128.76,61.90,31.76,31.01,29.48,29.39,29.22,29.18,28.87,25.75,22.56,14.42.
实施例4：溴化N，N'-二(1-正十四烷基-3-吡啶基)乙二酰胺双季铵盐(BPOB-14)的制备
(1)制备N，N'-二(3-吡啶基)乙二酰胺同实施例1；
(2)在反应瓶中，加入N，N'-二(3-吡啶基)乙二酰胺(1.45g，6mmol)和溴代正十四烷(58.23g，210mmol)，加热到145℃反应25小时，冷却，抽滤，用乙酸乙酯洗涤，干燥得3.78g溴化N，N'-二(1-正十四烷基-3-吡啶基)乙二酰胺双季铵盐，产率79％，熔点：213.5-215.3℃。1H NMR(600MHz,DMSO-d6,ppm)δ:11.95(s,2H),9.45(s,2H),8.96(d,J＝5.9Hz,2H),8.89(d,J＝8.7Hz,2H),8.22(s,2H),4.68(s,4H),1.92(s,4H),1.26(m,44H),0.84(s,6H).13CNMR(150MHz,DMSO-d6,ppm)δ:158.93,141.10,138.29,137.01,136.19,128.82,61.84,31.75,31.01,29.53,29.51,29.48,29.39,29.22,29.17,28.87,25.85,22.56,14.42.
实施例5：本发明的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂用于水性涂料的闪锈抑制性和缓蚀效果评价实例
本发明的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂用于水性涂料，在水性醇酸防锈漆中添加0.5％ BPOB-12(表1)，与空白对照组比较，有比较优异的闪锈抑制性和缓蚀性能，而且热储存稳定性和空白对照组无差异，配方适应性良好，见表2。
表1水性醇酸防锈漆的原材料配比
表2关键性能对比
本发明的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂BPOB-8、BPOB-10、BPOB-14用于水性涂料，同样具有比较优异的闪锈抑制性和缓蚀性能。
Claims (5)
1.一种双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂，其特征在于，它是乙二酰胺桥联的吡啶季铵盐，具有如下结构式：
其中R代表碳数为8、10、12、14的长链烷烃。
2.如权利要求1所述的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂的制备方法，其特征在于，是以3-氨基吡啶为起始原料，与草酰氯反应得到N，N'-二(3-吡啶基)乙二酰胺，再与溴代烷烃反应制得乙二酰胺桥联的吡啶季铵盐。
3.如权利要求2所述的双酰胺类吡啶季铵盐水性涂料防腐缓蚀剂的制备方法，其特征在于，步骤如下：
(1)将3-氨基吡啶和等摩尔量的三乙胺加入反应瓶中，再加入体积为三乙胺10～15倍量的溶剂二氯甲烷，然后滴加摩尔量为3-氨基吡啶0.4～0.5倍量的草酰氯，加完后室温搅拌反应7～10小时，抽滤，用水洗涤得N，N'-二(3-吡啶基)乙二酰胺；
(2)将N，N'-二(3-吡啶基)乙二酰胺和25～35倍摩尔量的溴代烷烃加入反应瓶中，加热到130～150℃反应7～10小时，冷却，抽滤，用乙酸乙酯洗涤得乙二酰胺桥联的吡啶季铵盐。
4.如权利要求1所述的防腐缓蚀剂在水性涂料中的应用。
5.一种水性涂料，其特征在于含有如权利要求1所述的防腐缓蚀剂。
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