CN112624935A - 一种含功能基的可降解型Gemini季铵盐及其制备方法 - Google Patents

一种含功能基的可降解型Gemini季铵盐及其制备方法 Download PDF

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CN112624935A
CN112624935A CN202011577686.2A CN202011577686A CN112624935A CN 112624935 A CN112624935 A CN 112624935A CN 202011577686 A CN202011577686 A CN 202011577686A CN 112624935 A CN112624935 A CN 112624935A
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quaternary ammonium
ammonium salt
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tertiary amine
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孔洪涛
马秀侠
刘路
朱俊
刘哲
刘玲玲
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Anhui Kiwi Biotech Co ltd
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Abstract

本发明提供一种含功能基的可降解型Gemini季铵盐，结构式为以下两种：
Figure DDA0002864848890000011
其中R为C8‑C16的长链烷基；X为Cl或Br；Y为

Description

一种含功能基的可降解型Gemini季铵盐及其制备方法
技术领域
本发明属于阳离子型季铵盐表面活性剂领域，具体涉及一种含功能基的可降解型Gemini季铵盐及其制备方法。
背景技术
Gemini型双子活性剂又被称为双阳离子洗涤剂、双季铵盐表面活性剂和二聚表面活性剂，其分子中的联接基通过化学键将两个正电性的亲水基联接起来，削弱了亲水基间及其水化层间的斥力，促进了双子表面活性剂分子在水溶液表面的吸附和在水溶液中的自聚，从而导致其具有很高的表面吸附能力和聚集体形成能力。阳离子型双子表面活性剂由于其特殊的结构使其表现出许多比传统表面活性剂更优良的性质，如：乳化性能好、毒性小、较低的临界胶束浓度、较强的杀菌性能、能够更有效的降低水的表面张力、比普通表面活性剂更低的Krafft点、良好的皂化分散能力以及与其它表面活性剂混合时表现出来的良好协同效应等，因而被称为新一代表面活性剂，广泛应用于制备新材料、杀菌剂、抑制金属腐蚀、织物染整、石油开采等领域。
相较于传统的单链及双链季铵盐，由于1个分子中有2个季铵正离子，电荷密度更高，增强了其对细菌细胞表面的有效吸附，从而改变细胞壁的渗透性，比典型的单双链季铵盐有更强的抗细菌和抗霉菌活性，传统烷基双子季铵盐由于生物降解性差，使用受限。
伴随着环保意识的不断增强，能够生物降解的杀菌剂得到了越来越多的重视。因此本发明中所述双子型季铵盐中引入了酯键或酰胺键，大大提高了其水解性能，且在连接基团中引入吸电子基团，对N+电荷影响，N+电正性加强，使其对于带负电的细菌吸引性增强，大大提升了其杀菌性能。
发明内容
本发明的目的在于提供一种高效环保，简单易制备可实现工业化的一种带功能基团可降解的Gemini季铵盐及其制备方法。
具体的技术方案为：
一种含功能基的可降解型Gemini季铵盐，结构式为以下两种：
Figure BDA0002864848880000011
Figure BDA0002864848880000021
其中R为C8-C16的长链烷基；
X为Cl或Br；
Y为
Figure BDA0002864848880000022
其中，式1的制备方法，包括以下步骤：
(1.1)脂肪酰氧亚甲基二甲基叔胺的合成
在单口烧瓶中依次加入DCM、脂肪醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为脂肪酰氧亚甲基二甲基叔胺产物。
(1.2)Gemini季铵盐的合成
在带有搅拌回流的反应器中依次加入乙腈、脂肪酰氧亚甲基二甲基叔胺(2eq)、桥接基团(1eq)、碱性催化剂(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子。
合成路线如下：
Figure BDA0002864848880000023
其中，式2的制备方法，包括以下步骤：
(2.1)脂肪酰胺丙基二甲基叔胺的合成
在带有搅拌器和分流装置的反应器中加入DCM、脂肪酸(1eq)和EDCI(1.2eq)、HOBT(1.2eq)，搅拌状态1h后加入N,-二甲基-1,3-丙二胺(1eq)继续反应12h，反应结束加水萃取2-3次，取有机相减压蒸发浓缩，冷却至室温可获得脂肪酰胺丙基二甲基叔胺。
(2.2)Gemini季铵盐的合成
在带有搅拌回流的反应器中依次加入乙腈、脂肪酰胺丙基二甲基叔胺(2eq)、桥接基团(1eq)、碱性催化剂(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子。
Figure BDA0002864848880000031
本发明相比于现有技术的优势如下：
1.本制备方法中所述合成的季铵盐，在酯化或酰胺缩合过程中反应条件温和，且无需通过将一个底物过量以提高产率，在纯化过程中只需洗涤浓缩即可制备高纯度产物。
2.本发明所述的季铵盐由于引入了易降解的酯键或酰胺键，使用之后排入自然水体容易降解，降解之后的物质不具有抗菌性能，不利于耐药菌的产生，是一种环保的新型季铵盐。
3.本发明所述的季铵盐由于引入了带吸电子的功能基团，能够使该季铵盐分子正电性增强，对于在环境中带负电的细菌等微生物吸引性更强，使其具有更低的最小抑菌浓度。可大大降低杀菌时季铵盐的使用量。
具体实施方式
结合实施例说明本发明的具体技术方案。
实施例1：其结构如下：
Figure BDA0002864848880000032
N,N-二甲基甘氨酸十二烷基酯的合成：在单口烧瓶中依次加入DCM、十二醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为油状N,N-二甲基甘氨酸十二烷基酯产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、N,N-二甲基甘氨酸十二烷基酯(2eq)、1,3-二氯丙酮(1eq)、Na2CO3(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.8％。
实施例2：其结构如下：
Figure BDA0002864848880000041
N,N-二甲基甘氨酸十二烷基酯的合成：在单口烧瓶中依次加入DCM、十二醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为油状N,N-二甲基甘氨酸十二烷基酯产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、N,N-二甲基甘氨酸十二烷基酯(2eq)、1,3-二溴丙酮(1eq)、Na2CO3(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.9％。
实施例3：其结构如下：
Figure BDA0002864848880000042
N,N-二甲基甘氨酸癸基酯的合成：在单口烧瓶中依次加入DCM、1-癸醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为油状N,N-二甲基甘氨酸癸基酯产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、N,N-二甲基甘氨酸癸基酯(2eq)、1,3-二氯丙酮(1eq)、Na2CO3(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.9％。
实施例4：其结构如下：
Figure BDA0002864848880000051
辛基酰胺丙基二甲胺的合成：在带有搅拌器和分流装置的反应器中加入DCM、辛酸(1eq)和EDCI(1.2eq)、HOBT(1.2eq)，搅拌状态1h后加入N,-二甲基-1,3-丙二胺(1eq)继续反应12h，反应结束加水萃取2-3次，取有机相减压蒸发浓缩，冷却至室温可获得淡黄色透明液态辛基酰胺丙基二甲胺产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、辛基酰胺丙基二甲胺(2eq)、1,4-二氯-2,5-二硝基苯(1eq)、K2CO3(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.3％。
实施例5：其结构如下：
Figure BDA0002864848880000052
N,N-二甲基甘氨酸十二烷基酯的合成：在单口烧瓶中依次加入DCM、十二醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为油状N,N-二甲基甘氨酸十二烷基酯产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、N,N-二甲基甘氨酸十二烷基酯(2eq)、1,4-二氯-2,5-二硝基苯(1eq)、K2CO3(0.1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.7％。
实施例6：其结构如下：
Figure BDA0002864848880000061
辛基酰胺丙基二甲胺的合成：在带有搅拌器和分流装置的反应器中加入DCM、辛酸(1eq)和EDCI(1.2eq)、HOBT(1.2eq)搅拌1h后加入N,-二甲基-1,3-丙二胺(1eq)继续反应12h，反应结束加水萃取2-3次，取有机相减压蒸发浓缩，冷却至室温可获得淡黄色透明液态辛基酰胺丙基二甲胺产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、辛基酰胺丙基二甲胺(2eq)、丙二酰氯(1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.6％。
实施例7：其结构如下：
Figure BDA0002864848880000062
N,N-二甲基甘氨酸癸基酯的合成：在单口烧瓶中依次加入DCM、1-癸醇(1eq)、N,N-二甲基甘氨酸(1eq)、EDCI(1.2eq)、DMAP(0.15eq)，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为油状N,N-二甲基甘氨酸癸基酯产物。
Gemini季铵盐的合成：在带有搅拌回流的反应器中依次加入乙腈、N,N-二甲基甘氨酸癸基酯(2eq)、丙二酰氯(1eq)，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子，根据国家标准GB/T15818-2006对该结构进行生物降解性能测定，检测结果显示第七天的生物降解度为99.8％。

Claims (3)

1.一种含功能基的可降解型Gemini季铵盐，其特征在于，结构式为以下两种：
Figure FDA0002864848870000011
其中R为C8-C16的长链烷基；
X为Cl或Br；
Y为
Figure FDA0002864848870000012
2.一种含功能基的可降解型Gemini季铵盐的制备方法，其特征在于，权利要求1所述的式1的制备方法，包括以下步骤：
(1.1)脂肪酰氧亚甲基二甲基叔胺的合成
在单口烧瓶中依次加入DCM、脂肪醇、N,N-二甲基甘氨酸、EDCI、DMAP，室温搅拌12h，反应结束后加水萃取2-3遍，取有机相旋干即为脂肪酰氧亚甲基二甲基叔胺产物；
(1.2)Gemini季铵盐的合成
在带有搅拌回流的反应器中依次加入乙腈、脂肪酰氧亚甲基二甲基叔胺、桥接基团、碱性催化剂，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子。
3.一种含功能基的可降解型Gemini季铵盐的制备方法，其特征在于，权利要求1所述的式2的制备方法，包括以下步骤：
(2.1)脂肪酰胺丙基二甲基叔胺的合成
在带有搅拌器和分流装置的反应器中加入DCM、脂肪酸和EDCI、HOBT，搅拌状态1h后加入N,-二甲基-1,3-丙二胺继续反应12h，反应结束加水萃取2-3次，取有机相减压蒸发浓缩，冷却至室温可获得脂肪酰胺丙基二甲基叔胺；
(2.2)Gemini季铵盐的合成
在带有搅拌回流的反应器中依次加入乙腈、脂肪酰胺丙基二甲基叔胺、桥接基团、碱性催化剂，60℃搅拌回流12h，反应结束后旋干，用二氯甲烷洗涤2-3遍即得白色粉末所述季铵盐分子。
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