CN111303208B - 一种具有抑菌功能的位阻胺光稳定剂及其制备方法 - Google Patents
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Abstract
本发明属于高分子材料助剂领域,尤其涉及一种具有抑菌功能的位阻胺光稳定剂及其制备方法。本发明以反应活性较高的三氯化磷为官能团键合反应起始原料,以简便易行的反应方法,得到具有抗光老化性能的烷氧基位阻胺与抑菌性能的N‑卤代位阻胺的新型多功能稳定剂系列化合物,其分子中利用亚磷酸酯结构键合N‑卤代位阻胺基团和烷氧基位阻胺基团,分子中两种不同官能团体现出正向协同效应,体现出良好光稳定性能的同时,表现出良好的抑菌性能。
Description
技术领域
本发明属于高分子材料助剂领域,尤其涉及一种具有抑菌功能的位阻胺光稳定剂及其制备方法。
背景技术
为了改善分子材料性能,延长使用寿命,在高分子材料中需要添加各种助剂。通常,高分子材料助剂在使用过程中需要复配或分次添加于高分子材料加工过程中,整体过程非常复杂。
其中,光稳定剂是指能够抑制或减缓由于光氧化作用而在高分子材料中添加的助剂。位阻胺光稳定剂是一类性能优良的光稳定剂。由于位阻胺性能优良,已经成为光稳定剂的主流。
有研究表明,在合适条件下不同功能基团有可能表现出比较好的协同效应。受此启发,多功能、高效的高分子材料稳定剂成为研究者追求的目标。在此研究过程中,研究者多关注于复配助剂的开发,对于同一分子中键合不同官能团形成的多功能高效助剂的研究开发则关注较少,成功范例就更为匮乏。
一个成功范例是Tinuvin144,分子结构中的受阻酚基团和位阻胺基团表现出了良好的协同效应,使其成为位阻胺光稳定剂中一个著名品牌。另外,国内研发的具有自主知识产权的GW540,也是一种较为有名的兼具阻燃性、光稳定性的双功能产品。
由于高分子材料特别是应用于生活日常、医疗卫生的高分子材料制品对其安全性能的要求,近年来高分子材料添加剂中抑菌剂也是研究关注点之一,高效低毒的抑菌剂是研究者追求的目标。同时,其与高分子材料以及其它添加剂的相容性也是必须考虑的因素之一。
2005年以来,美国的SunYuyu等曾报道将位阻胺中的哌啶胺基转化为N-氯海因结构,体现出了较为高效的杀菌性能。其研究思路主要是改进传统的普通位阻胺稳定剂,即对3346、944等商业化产品基础上加以N-卤代反应而得到。
中国专利CN102617450B曾报道了含有位阻酚和N-卤代位阻胺基团的化合物,该化合物中位阻酚表现出较好的抗氧化性能,同时N-卤代位阻胺表现出较好的抑菌性能,二者协同效应明显。
发明内容
本发明针对上述现有技术存在的不足,提供一种具有抑菌功能的位阻胺光稳定剂及其制备方法。
本发明解决上述技术问题的技术方案如下:一种具有抑菌功能的位阻胺光稳定剂,其结构式如下:
其中,R1、R2各自独立地为卤素X或烷氧基;卤素X为Cl或Br;且R1、R2不能同时为卤素。
进一步,所述的烷氧基为-OR3;其中,R3为C1-C18直链烷基、支链烷基、环烷基或C3-C8链烯基中的任意一种。
本发明的第二个目的在于提供上述具有抑菌功能的位阻胺光稳定剂的制备方法,步骤如下:
(1)将N-卤代-2,2,6,6-四甲基哌啶醇溶解于溶剂中,加入反应器,同时加入缚酸剂,再缓慢加入三氯化磷溶液,控制反应温度为15-30℃,反应4-36h,得到产物A;其中,N-卤代-2,2,6,6-四甲基哌啶醇与三氯化磷的摩尔比为(1-2):1;
(2)将步骤(1)的产物A溶解于溶剂中,加入反应器,同时加入缚酸剂,再缓慢滴加N-烷氧基-2,2,6,6-四甲基哌啶醇溶液,控制反应温度为15-30℃,反应4-36h,得到目标产物;其中,产物A与N-烷氧基-2,2,6,6-四甲基哌啶醇的摩尔比为1:(1-2)。
进一步,步骤(1)(2)中,所述溶剂为二氯甲烷、三氯甲烷、四氯化碳、甲苯、二甲苯、二硫化碳、丙酮、乙酸乙酯、甲基叔丁基醚或四氢呋喃中的一种或两种以上。
进一步,步骤(1)(2)中,所述缚酸剂为吡啶、N-甲基咪唑或三乙胺中的一种或两种以上。
本发明的特点和有益效果是:
本发明以反应活性较高的三氯化磷为官能团键合反应起始原料,以简便易行的反应方法,得到具有抗光老化性能的烷氧基位阻胺与抑菌性能的N-卤代位阻胺的新型多功能稳定剂系列化合物,其分子中利用亚磷酸酯结构键合N-卤代位阻胺基团和烷氧基位阻胺基团,分子中两种不同官能团体现出正向协同效应,体现出良好光稳定性能的同时,表现出良好的抑菌性能。
具体实施方式
以下对本发明的原理和特征进行描述,所举实例只用于解释本发明,并非用于限定本发明的范围。
实施例1
一种具有抑菌功能的位阻胺光稳定剂的制备方法,合成反应式如下:
制备步骤如下:
(1)将2.75g三氯化磷溶于50mL二氯甲烷溶液,加入250mL四口瓶中,加入三乙胺6.90g,15℃、搅拌条件下向反应瓶中慢慢滴加7.69g 1-氯-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(60mL),4h滴加完毕后,保持15℃反应3h;
(2)向步骤(1)的反应体系中滴加3.75g 1-甲氧基-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(30mL),滴加完毕后升温至30℃反应3h;
(3)以100mL去离子水洗涤反应体系三次,有机相减压蒸除溶剂得到黄色固体,以无水乙醇30mL洗涤后抽滤,滤饼以乙醇与乙酸乙酯重结晶,得到白色产品5.24g,收率43.8%,熔点为165.2-167.1℃。
1HNMR(500MHz,CDCl3),&ppm:1.19(s,12H),1.26(s,12H);1.33(s,12H);1.45~1.53(m,12H),3.71(s,3H);MS(ESI):[M+1]599.6。
实施例2
一种具有抑菌功能的位阻胺光稳定剂,结构式如下:
制备步骤如下:
(1)将2.75g三氯化磷溶于50mL二氯甲烷溶液,加入250mL四口瓶中,再加入吡啶10mL,15℃、搅拌条件下向反应瓶中慢慢滴加7.49g 1-丙氧基-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(50mL),3h滴加完毕后,保持15℃反应3h;
(2)向步骤(1)的反应体系中滴加3.83g 1-氯-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(30mL),滴加完毕后升温至30℃反应4h;
(3)以100mL去离子水洗涤反应体系三次,有机相减压蒸除溶剂得到黄色固体,以无水乙醇30mL洗涤后抽滤,滤饼以乙醇与丙酮重结晶,得到白色产品4.71g,收率36.2%,熔点为131.7-133.8℃。
1HNMR(500MHz,CDCl3),&ppm:0.97(t,6H),1.21(s,24H);1.32(s,12H);1.37~1.42(m,4H),1.47~1.55(m,12H),3.84(s,3H);MS(ESI):[M+1]651.3。
实施例3
一种具有抑菌功能的位阻胺光稳定剂的制备方法,制备反应式如下:
制备步骤如下:
(1)将2.75g三氯化磷溶于50mL二氯甲烷溶液,加入250mL四口瓶中,再加入三乙胺6.9g,15℃、搅拌条件下向反应瓶中慢慢滴加9.44g 1-溴-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(50mL),3h滴加完毕后,保持15℃反应3h;
(2)向步骤(1)的反应体系中滴加5.11g 1-环己氧基-2,2,6,6-四甲基哌啶醇的二氯甲烷溶液(30mL),滴加完毕后升温至30℃反应4h;
(3)以100mL去离子水洗涤反应体系三次,有机相减压蒸除溶剂得到浅黄色固体,以无水乙醇30mL洗涤后抽滤,滤饼以异丙醇与丙酮重结晶,得到浅黄色产品5.41g,收率35.7%,熔点为170.3-172.1℃。
1HNMR(500MHz,CDCl3),&ppm:0.97(t,6H),1.21(s,24H);1.29(s,12H);1.35~1.41(m,4H),1.49~1.57(m,16H),3.62(s,1H),3.87(s,3H);MS(ESI):[M+1]756.4。
对比例1
一种光稳定剂的制备方法,合成反应式如下:
制备步骤如下:
(1)向250mL四口瓶中加入1-氯-2,2,6,6-四甲基哌啶醇11.5g、三乙胺9.1g和氯仿100mL,15℃、搅拌条件下慢慢滴加三氯化磷(2.75g)的氯仿溶液(氯仿用量30mL),滴加完毕后升温至30℃,反应8h后停止反应;
(2)用100mL去离子水洗涤反应体系三次,有机相减压蒸除溶剂得到黄色固体,以无水乙醇30mL洗涤后抽滤,无水乙醇多次洗涤滤饼,干燥,得到白色产品7.81g,收率64.7%,熔点为183.2-184.6℃。
1HNMR(500MHz,CDCl3),&ppm:1.22(s,12H),1.29(s,12H),1.35(s,12H),1.52~1.60(m,12H),3.71(s,3H);MS(ESI):[M+1]604.1。
测试
对实施例1-3和对比例1所得产物进行性能评价。
1、抗光氧老化性能评价
按GB/T 17391—1998《聚乙烯管材与管件热稳定性试验方法》,在PE、PP中分别添加0.2wt%的助剂,在美国Perkin Elmer公司Pyris 1DSC差示扫描量热分析装置上进行氧化诱导期试验,测试结果见表1。
表1
由表1可以看出,实施例1-3的光稳定剂均能使PE、PP的氧化诱导期明显延长;而对比例1所得的产物中没有烷氧基位阻胺基团与N-卤代位阻胺基团形成正向协同效应,因此其对PE、PP的氧化诱导期影响不大。
2、抗菌性能测试
按照GB15979-2002《一次性卫生用品卫生标准》,将实施例1-3和对比例1所得产物、GW540分别以0.3mmol/L浓度溶解于二甲基亚砜和水(体积比=1:2)的混合溶剂中,对大肠杆菌和金黄色葡萄球菌进行抑菌活性测试(实验时间60min),结果见表2。
表2
大肠杆菌抑制率 | 金黄色葡萄球菌抑制率 | |
实施例1 | 78.3% | 71.5% |
实施例2 | 56.1% | 47.6% |
实施例3 | 90.1% | 85.2% |
对比例1 | 84.6% | 88.7% |
GW540 | ─ | ─ |
由表2可以看出,作为对比的GW540没有抑菌作用;实施例1-3和对比例1所得产物均对大肠杆菌和金黄色葡萄球菌体现出较为明显的抑制作用。
综上,虽然对比例1所得产物对大肠杆菌和金黄色葡萄球菌的抑制作用最优,但是其对PE、PP的氧化诱导期的延长不如GW540。因此综合来看,本发明制备的烷氧基位阻胺基团与N-卤代位阻胺基团形成正向协同效应的光稳定剂兼具良好的光稳定性能和良好的抑菌性能,更适合用于高分子材料稳定剂。
以上所述仅为本发明的较佳实施实例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (6)
2.一种权利要求1所述具有抑菌功能的位阻胺光稳定剂的制备方法,其特征在于,步骤如下:
(1)将N-卤代-2,2,6,6-四甲基哌啶醇溶解于溶剂中,加入反应器,同时加入缚酸剂,再缓慢加入三氯化磷溶液,控制反应温度为15-30℃,反应4-36h,得到产物A;其中,N-卤代-2,2,6,6-四甲基哌啶醇与三氯化磷的摩尔比为(1-2):1;
(2)将步骤(1)的产物A溶解于溶剂中,加入反应器,同时加入缚酸剂,再缓慢滴加N-烷氧基-2,2,6,6-四甲基哌啶醇溶液,控制反应温度为15-30℃,反应4-36h,得到目标产物;其中,产物A与N-烷氧基-2,2,6,6-四甲基哌啶醇的摩尔比为1:(1-2)。
3.根据权利要求2所述的制备方法,其特征在于,步骤(1)(2)中,所述溶剂为二氯甲烷、三氯甲烷、四氯化碳、甲苯、二甲苯、二硫化碳、丙酮、乙酸乙酯、甲基叔丁基醚或四氢呋喃中的一种或两种以上。
4.根据权利要求2所述的制备方法,其特征在于,步骤(1)(2)中,所述缚酸剂为吡啶、N-甲基咪唑或三乙胺中的一种或两种以上。
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