CN110746595B - 一种聚丙二酸基胍盐酸盐的制备方法 - Google Patents
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Abstract
本发明涉及一种聚丙二酸基胍盐酸盐的制备方法。制备方法：将丙二酸、盐酸胍混合均匀,加热熔融，加热温度120‑135℃；加入催化剂，加入分子量调节剂；整个反应过程都进行分水步骤,反应结束后,立即加入无水乙醇中,冷却室温,重结晶,过滤得到聚丙二酸基胍盐酸盐。本发明聚丙二酸基胍盐酸盐，对胍类消毒剂在结构上进行改进,引入吸电子基团酰基使得胍基的正电性更大,所以其杀菌能力就更强。
Description
技术领域
本发明涉及含胍聚合物的制备方法,具体地说是一种聚丙二酸基胍盐酸盐的制备方法。
背景技术
随着生活水平的日益提高，人们更加注重生活品质，追求健康的生活，市场上琳琅满目的杀菌剂应运而生。虽然市场上的杀菌剂种类繁多，但他们的杀菌机理、杀菌范围、杀菌效果、毒副作用也不尽相同。例如：季铵盐、有机硫/磷/砷类杀菌剂，虽杀菌效果较好，但是毒副作用较大，有些产品已经被禁用；取代苯类杀菌剂杀菌范围小；乙醇类、咪唑类杀菌剂的抗菌时效短，使用不方便；所以需要一种高效持久、无毒无副作用、无色无味的杀菌剂。胍类高分子杀菌剂其化学结构式中有胍基，胍基化合物具有杀菌性、高稳定性、较好的生物活性等优良特性，含胍基的聚合物呈正电性，故极易被通常呈电负性的各种细菌和病毒所吸附，从而抑制细菌***，使其丧失生殖能力。另外，聚合物形成的薄膜堵塞了微生物的呼吸孔道，使其迅速窒息死亡，故而有很高的杀菌性。
发明内容
本发明的目的是提供一种杀菌能力强的含胍聚合物的制备方法，即聚丙二酸基胍盐酸盐的制备方法。
本发明的技术方案：
一种聚丙二酸基胍盐酸盐的制备方法，将丙二酸、盐酸胍混合均匀,加热熔融，加热温度120-135℃；催化剂，加入分子量调节剂；整个反应过程都进行分水步骤,反应结束后,立即加入无水乙醇中,冷却室温,重结晶,过滤得到聚丙二酸基胍盐酸盐。
丙二酸、盐酸胍、催化剂和分子量调节剂的摩尔1:1:0.01-0.05:0.02-0.06。
所用催化剂为对甲苯磺酸、浓硫酸、磷酸。
所用分子量调节剂为疏基丙酸、3-巯基丙酸异辛酯。
本发明的有益效果：
1、本发明聚丙二酸基胍盐酸盐，对胍类消毒剂在结构上进行改进,引入吸电子基团酰基使得胍基的正电性更大,所以其杀菌能力就更强。
2、本发明聚丙二酸基胍盐酸盐，对聚胍类消毒剂在结构上进行改进，将吸电子酰基引入高分子长链中，在聚合物长链胍基两侧增加了吸电子的酰基，因此消毒基团胍基电子被酰基吸引使得胍基正电荷更加正，这样使得消毒能力更强。同时采用聚丙二酸与本课题组的专利一种聚己二酸基胍盐酸盐制备方法(申请公布号CN105315459A)进行对比，由图1和图2可知：聚丙二酸基胍盐酸盐单体的分子量比聚己二酸基胍盐酸盐小，质量相同的条件下聚丙二酸基胍盐酸盐中含有的胍基基团比聚己二酸基胍盐酸盐的多，所以杀菌效果比聚己二酸基胍盐酸盐好。
附图说明
图1为聚己二酸基胍盐酸盐结构式。
图2为聚丙二酸基胍盐酸盐结构式。
图3为聚丙二酸基胍盐酸盐与聚己二酸基胍盐酸盐杀大肠杆菌对照图。
具体实施方式
聚丙二酸基胍盐酸盐的制备方法是在装有温度计、分水器和冷凝器的容器中将丙二酸、盐酸胍混合均匀,加热熔融.加热温度120-135℃,最佳反应温度是125℃:加入催化剂,所用催化剂为对甲苯磺酸或浓硫酸或磷酸；分水；加入分子量调节剂,所用分子量调节剂为巯基丙酸或3-巯基丙酸异辛酯；反应结束后,趁热立即加入无水乙醇中,冷却室温.重结晶，过滤得到聚丙二酸基胍盐酸盐。丙二酸、盐酸胍.催化剂和分子量调节剂的摩尔比为1:1:0.01-0.05:0.02-0.06.
实施例1:在装有温度计,分水器和冷凝器的-三颈瓶(500mL)中,加入丙二酸(104.03g)、盐酸胍(95.53g),加热125℃,熔融后,搅拌,加入1.63g对甲苯磺酸,搅拌3.0小时,加入1.92g巯基丙酸。分水结束后.趁热将混合液加入到装有450ml医用去离子水的烧杯中，搅拌，完全溶解后,冷却室温，过夜,过滤，得聚丙二酸基胍盐酸盐。
实施例2:在装有温度计,分水器和冷凝器的-三颈瓶(500mL)中,加入丙二酸(104.03g)、盐酸胍(95.53g),加热123℃,熔融后,搅拌,加入1.3g浓硫酸,搅拌2.8小时,加入2.02g3-巯基丙酸异辛酯。分水结束后.趁热将混合液加入到装有500mL无水乙醇的烧杯中,搅拌,完全溶解后,冷却室温，过夜,过滤,得聚丙二酸基胍盐酸盐。
实施例3:在装有温度计,分水器和冷凝器的-三颈瓶(500mL)中,加入丙二酸(104.03g)、盐酸胍(95.53g),加热124℃,熔融后,搅拌,加入1.72g浓磷酸,搅拌2.8小时,加入2.02g 3-巯基丙酸异辛酯。分水结束后.趁热将混合液加入到装有550mL无水乙醇的烧杯中,搅拌,完全溶解后,冷却室温，过夜,过滤,得聚丙二酸基胍盐酸盐。
实施例4:在装有温度计,分水器和冷凝器的-三颈瓶(500mL)中,加入丙二酸(104.03g)、盐酸胍(95.53g),加热130℃,熔融后,搅拌,加入2.93g对甲苯磺酸,搅拌2.8小时,加入2.89g 3-巯基丙酸异辛酯。分水结束后.趁热将混合液加入到装有500mL无水乙醇的烧杯中,搅拌,完全溶解后,冷却室温，过夜,过滤,得聚丙二酸基胍盐酸盐。
实施例5:在装有温度计,分水器和冷凝器的三颈瓶(500mL)中,加入丙二酸(104.03g)、盐酸胍(95.53g),加热132℃,熔融后,搅拌,加入2.03g浓磷酸,搅拌3.0小时,加入2.26g巯基丙酸。分水结束后.趁热将混合液加入到装有500mL无水乙醇的烧杯中,搅拌,完全溶解后,冷却室温，过夜,过滤,得聚丙二酸基胍盐酸盐。
图3聚己二酸基胍盐酸盐与聚丙二酸基胍盐酸杀大肠杆菌对照图
由上图可知，左侧●代表聚己二酸基胍盐酸盐杀菌曲线，当药液稀释10倍时杀菌能力变差；右侧Х带便聚丙二酸基胍盐酸盐，当药液稀释15倍时杀菌能力变弱，由此推断聚丙二酸基胍盐酸盐杀菌能力比聚己二酸基胍盐酸盐强1/3。
Claims (4)
1.一种聚丙二酸基胍盐酸盐的制备方法，其特征在于：将丙二酸、盐酸胍混合均匀,加热熔融，加热温度120-135℃；加入催化剂，加热、搅拌3小时，加入分子量调节剂；整个反应过程都进行分水步骤,反应结束后,立即加入无水乙醇中,冷却室温,重结晶,过滤得到聚丙二酸基胍盐酸盐。
2.根据权利要求1所述一种聚丙二酸基胍盐酸盐的制备方法，其特征在于：丙二酸、盐酸胍、催化剂和分子量调节剂的摩尔比为1:1:0.01-0.05:0.02-0.06。
3.根据权利要求1所述一种聚丙二酸基胍盐酸盐的制备方法，其特征在于：所用催化剂为对甲苯磺酸、浓硫酸、磷酸。
4.根据权利要求1所述一种聚丙二酸基胍盐酸盐的制备方法，其特征在于：所用分子量调节剂为疏基丙酸、3-巯基丙酸异辛酯。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| CN101857540A (zh) * | 2009-04-09 | 2010-10-13 | 宁波大学 | 用尼龙-66解聚生产己二酸、己二胺盐酸盐和聚六亚甲基单(双)胍盐酸盐的方法 |
| CN105315459A (zh) * | 2014-10-29 | 2016-02-10 | 吉林云飞医药有限公司 | 一种聚己二酸基胍盐酸盐的制备方法 |
| CN106380598A (zh) * | 2016-10-15 | 2017-02-08 | 石家庄学院 | 一种高分子离子液体的合成方法及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BR0111163A (pt) * | 2000-05-11 | 2003-04-08 | P O C Oil Industry Technology | Polìmeros biocidas à base de sais de guanidina |
| FR2929281B1 (fr) * | 2008-03-28 | 2011-03-11 | Polyrise | Modification de la chimie de surface d'especes macromoleculaires en presence d'une guanidine conjuguee |
-
2019
- 2019-11-01 CN CN201911059343.4A patent/CN110746595B/zh active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| CN101857540A (zh) * | 2009-04-09 | 2010-10-13 | 宁波大学 | 用尼龙-66解聚生产己二酸、己二胺盐酸盐和聚六亚甲基单(双)胍盐酸盐的方法 |
| CN105315459A (zh) * | 2014-10-29 | 2016-02-10 | 吉林云飞医药有限公司 | 一种聚己二酸基胍盐酸盐的制备方法 |
| CN106380598A (zh) * | 2016-10-15 | 2017-02-08 | 石家庄学院 | 一种高分子离子液体的合成方法及其应用 |
Non-Patent Citations (4)
| Title |
|---|
| Structural characterization and antibacterial activity of oligoguanidine;Dafu Wei et al;Materials Science and Engineering C;第29卷;第1776-1780页 * |
| 含胍基抗菌聚合物的合成及应用;张浩 等;化学进展;第31卷(第5期);第681-689页 * |
| 聚六亚甲基胍盐酸盐的合成研究;曾平;谢维跃;蒋健;魏盼中;许筠;;日用化学工业(第11期);第629-632页 * |
| 黄奇然 等.聚六亚甲基盐酸胍在造纸工业中的应用.中国造纸.2011,第30卷(第6期),第32-36页. * |
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