CN111424427A - 一种非溶出型抗菌整理剂及其制备方法 - Google Patents
一种非溶出型抗菌整理剂及其制备方法 Download PDFInfo
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- CN111424427A CN111424427A CN202010347924.4A CN202010347924A CN111424427A CN 111424427 A CN111424427 A CN 111424427A CN 202010347924 A CN202010347924 A CN 202010347924A CN 111424427 A CN111424427 A CN 111424427A
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- quaternary ammonium
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- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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Abstract
本发明公开了一种非溶出型抗菌整理剂及其制备方法,按重量份数计包括:季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、引发剂、交联剂、催化剂、乳化剂和水;本发明基于硅烷的分子偶联作用,充分利用有机硅分子上三甲氧基官能团的既可与玻璃、硅、金属等无机材质反应结合、又可与纤维树脂等有机分子直接结合并能够在一般物体表面“扎根”固定的性质,达到固化长效消毒,尤其对大肠杆菌和金黄色葡萄球菌的抑制率较高,引入丙烯酸六氟丁酯,含氟基团可以降低抗菌整理剂的表面能,相较于传统的双子季铵盐抗菌剂更不易更不易溶出,与纤维结合牢固、持久,抗菌效果明显,多次洗涤后仍具有很好的抑菌效果。
Description
技术领域
本发明涉及一种非溶出型抗菌整理剂及其制备方法。
背景技术
在人类的日常生活中,难免会接触到各种各样的微生物,这些微生物可以直接或间接的对人体产生危害,而微生物在一定的环境条件下可以迅速繁殖,这些微生物以人体分泌的汗液、油脂、皮屑或织物本身的分解物质作为营养品迅速繁殖,形成大量有害的细菌并通过空气进行传播,从而引起疾病,影响人们的日常生活。微生物的存在还会导致织物纤维大分子降解,使织物出现脆损、变色、霉变等现象,影响服装及装饰品的外观、色泽;对于一些军用物品,如降落伞、炮衣、帐篷等,则会危及安全,影响战斗力,后果不堪设想;为了解决上述问题,可行的办法将能杀灭对人体和衣物有害的抗菌药剂来处理织物。
传统的抗菌剂主要采用季铵盐化合物,季铵盐类消毒剂是指用具有消毒作用的季铵类化合物为有效成分制成的消毒剂,其是一种阳离子表面活性剂的代表,因季铵盐化合物能吸附带负电荷的细菌,具有良好的杀菌作用,在国际上使用广泛;单链季铵盐的逐渐显现出一些缺点,如杀生谱较窄,细菌对其产生了耐药性以及对细菌具有较高的MIC值等;目前,在纺织品抗菌中,首先需要考虑普通季铵盐是溶出型的,易洗脱。但是,如果将硅氧烷引入季铵盐结构中制得有机硅季铵盐,可使其性能发生巨大变化;目前已有不少研究关于双子季铵盐抗菌剂的报道,也表现出了较为优异的抗菌性能和以及杀菌范围广等特性,但其仍为小分子季铵盐,存在小分子季铵盐的共性缺点,将其应用在织物上作为抗菌整理剂的效果并不理想。
发明内容
本发明的目的是为了解决以上现有技术的不足,提出了一种非溶出型抗菌
整理剂,按重量份数计包括:
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.02-2.1:1的长链卤代烯烃与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂和阻聚剂,90-110℃下加热回流20-48h,旋去溶剂,用乙醚萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2-3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7-10;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
优选地,所述的长链卤代烯烃为11-溴-1-十一烯、11-氯-1-十一烯和16-溴-1-十六烯中的任意一种。
优选地,所述的溶剂为异丙醇、丙酮和乙醇中的一种或几种。
优选地,所述的阻聚剂为对苯二酚。
优选地,所述的乳化剂由质量百分比为60~80%的非离子型乳化剂和20~40%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯、椰油脂肪酸二乙醇酰胺和失水山梨醇单硬脂酸酯中的一种或几种的混合物;所述的阳离子型乳化剂为十六烷基三甲基溴化铵和十二烷基苯磺酸钠中的一种或两种。
优选地,所述的引发剂为2,2-偶氮二(2-甲基丙基咪)二盐酸盐、偶氮二异丁腈和过硫酸铵中的任意一种。
优选地,所述的交联剂为N,N-亚甲基双丙烯酰胺。
优选地,所述的催化剂为双组分齐格勒纳塔催化剂,用量为双子季铵盐用量的0.15-0.3wt%。
优选地,所述的催化剂为TiCl4-Al(C2H5)3。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
当所述的长链卤代烯烃为16-溴-1-十六烯时,所述的季铵盐抗菌单体结构式为:
本发明的有益效果如下:
(1)本发明基于硅烷的分子偶联作用,充分利用有机硅分子上三甲氧基官能团的既可与玻璃、硅、金属等无机材质反应结合、又可与纤维树脂等有机分子直接结合并能够在一般物体表面“扎根”固定的性质,创新地在双子季铵盐上引入甲氧基烷基硅,将其应用在织物表面形成聚合性分子层达到固化长效消毒,而且具有较好的抗菌活性、较广的杀菌谱、较高的化学稳定性和较低的生物毒性;
(2)本发明将双子季铵盐长链与硅氧烷连接,既充分发挥了聚合双子季铵盐的较强的杀菌效力,使之在较低浓度下即可达到快速杀菌效果,尤其对大肠杆菌和金黄色葡萄球菌的抑制率较高,引入丙烯酸六氟丁酯,含氟基团可以降低抗菌整理剂的表面能,相较于传统的双子季铵盐抗菌剂更不易更不易溶出,与纤维结合牢固、持久,抗菌效果明显,多次洗涤后仍具有很好的抑菌效果,对人体安全可靠,因此可以得到广泛的应用。
具体实施方式
为了加深对本发明的理解,下面将结合实施例对本发明作进一步详述,该实施例仅用于解释本发明,并不构成对本发明保护范围的限定。
下述实施例中所使用的实验方法如无特殊说明,均为常规方法。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
实施例1
一种非溶出型抗菌整理剂,按重量份数计包括:季铵盐抗菌单体65份、丙烯酸六氟丁酯32份、十二烷基羧甲基钠型咪唑啉醋酸盐12份、2,2-偶氮二(2-甲基丙基咪)二盐酸盐0.05份、N,N-亚甲基双丙烯酰胺0.1份、TiCl4-Al(C2H5)30.04份、乳化剂2份、水100份;
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.05:1的11-溴-1-十一烯与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂异丙醇和对苯二酚,95℃下加热回流24h,旋去溶剂,用乙醚萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:8;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
在上述技术方案中,所述的乳化剂由质量百分比为80%的非离子型乳化剂和20%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯;所述的阳离子型乳化剂为十六烷基三甲基溴化铵。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
实施例2
一种非溶出型抗菌整理剂,按重量份数计包括:季铵盐抗菌单体70份、丙烯酸六氟丁酯35份、十二烷基羧甲基钠型咪唑啉醋酸盐8份、偶氮二异丁腈0.06份、N,N-亚甲基双丙烯酰胺0.2份、TiCl4-Al(C2H5)30.08份、乳化剂5份、水120份;
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.1:1的16-溴-1-十六烯与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂异丙醇和对苯二酚,100℃下加热回流30h,旋去溶剂,用乙醚萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
在上述技术方案中,所述的乳化剂由质量百分比为80%的非离子型乳化剂和20%的阳离子型乳化剂组成;所述的非离子型乳化剂为椰油脂肪酸二乙醇酰胺;所述的阳离子型乳化剂为十二烷基苯磺酸钠。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
性能测定
应用本发明的抗菌整理剂及产品浓度定型,参照中华人民共和国卫生部2002年(消毒技术规范),即采用琼脂稀释法,用磷酸盐缓冲液(简称PBS)将该洗液进行系列稀释,即将本发明的抗菌整理剂原液1份体积分别加入9份、49份、199份和499份体积磷酸盐缓冲液(PBS)进行稀释分别得到10倍、50倍、100倍、200倍、500倍稀释液。上述各稀释液分别与MH琼脂培养基混合溶解,进行如下浓度定型实验;
(1)MH琼脂培养基:根据中华人民共和国医药行业标准YY/T0665-2008,即每1000mL水加入酸水解酪蛋白17.5g和可溶性淀粉1.5g,和牛肉浸出粉2.0g,和琼脂15g,加热至沸腾溶解,然后经高压蒸汽灭菌法处理,置于45-50℃水浴中备用;
(2)PBS缓冲液:称取NaCl 8g、KCl 0.2g、Na2HPO41.44 g、KH2PO40.24g,加入990mL水溶解,调节pH为7.4,定容至1000mL,高压灭菌后室温保存;
(3)采用大肠杆菌(ATCC8099),配制菌悬液,浓度为107cfu/ml;
(4)中和剂:采用PBS缓冲液配制0.3%卵磷脂和3%的吐温80;
(5)胰胨大豆酪蛋白培养基(TSA培养基):根据中国药典2010标准及EP/USP标准,分别称取胰胨17g、多价蛋白胨3g、酵母膏6g、氯化钠5g、磷酸氢二钾2.5g、葡萄糖2.5g,加入蒸馏水900mL,将上述各成分加热搅拌溶解,调节pH至7.4,加水定容至1000mL,高压灭菌后备用;
(6)TSA培养基琼脂平板:分别称取胰胨17g、多价蛋白胨3g、酵母膏6g、氯化钠5g、磷酸氢二钾2.5g、葡萄糖2.5g、琼脂15g,加入蒸馏水900mL,将上述各成分加热搅拌溶解,调节pH至7.4,加水定容至1000mL,高压灭菌后备用;
(7)实验用菌:大肠杆菌(菌种编号ATCC8099)悬液,金黄色葡萄球菌(菌种编号ATCC6538)悬液,浓度均为1~5×108cfu/ml;
试验方法:取消毒无菌大试管3管,在超净台,分别加入0.9ml本发明的抗菌整理剂和预先采用10、50、100、200和500倍稀释的本发明的抗菌整理剂稀释液,再分别加到9.1ml经灭菌的中和剂中,混匀作用1.0min;而后,向各管加入0.1ml试验用菌悬液,在20℃±1℃条件下相互作用,第一管、第二管和第三管作用时间分别为2.5min、5.0min和7.5min,各试验管分别吸取5.0ml样液,按活菌培养计数方法测定37℃培养后存活菌数,每管样液接种10个MH培养基琼脂平板;按活菌培养计数方法对培养的菌落进行计数;
阳性对照:用0.1ml试验用菌悬液与9.9mL TSA培养基,作为阳性对照,进行平行试验;
所有试验样本均在37℃温箱中培养,对细菌繁殖体培养48h观察最终结果;灭菌试验重复3次,计算各组的活菌浓度(cfu/ml),并换算为对数值(N),然后按下式计算杀灭对数值;其中杀灭对数值(KL)=对照组平均活菌浓度的对数值(No)-试验组活菌浓度对数值(Nx)。
(8)棉织品的抗菌耐洗试验
应用本发明的固化性季铵盐消毒液整理棉织品的抗菌耐洗试验,操作如下:
1)称重棉花团,置于本发明的消毒液中,消毒液体积为棉花质量的50倍,常温浸泡30min,直接晾干,得到整理后的棉团;
2)抗菌棉织物抑菌测试,按FZ/T73023-2006中振荡法测试抗菌整理后棉团的抑菌率,实验用菌悬液为大肠杆菌悬液,浓度为1~5×108cfu/ml;
3)对整理后的棉团按照FZ/T73023-2006洗涤标准进行多次洗涤处理,在5、10、15、20、25和30次洗涤后进行实验。
实验结果
(1)本发明的可固化季铵盐配制的消毒液对细菌的消毒杀菌效果如表1所示。结果表明,依据卫生部《消毒技术规范》2002.11版技术规范要求,在20℃±1℃条件下本发明的抗菌整理剂,依据技术规范要求作用5.0min对大肠杆菌和金黄色葡萄球菌的杀灭对数值均大于5.0。
表1可固化季铵盐配制的消毒液对细菌的消毒杀菌效果
(2)抗菌整理耐久性分析中,本发明消毒液对整理后的棉团在大肠杆菌的抑制率如下:结果表明,本发明消毒液处理的棉团,在大肠杆菌悬液中18小时震摇,对细菌生长的抑制率达到98%;耐洗试验中,30次洗涤后的抑制率大于97%。
以上所述仅为本发明的较佳实施例而已,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 (10)
1.一种非溶出型抗菌整理剂,其特征在于,按重量份数计包括:
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.02-2.1:1的长链卤代烯烃与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂和阻聚剂,90-110℃下加热回流20-48h,旋去溶剂,用乙醚萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2-3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7-10;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
2.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的长链卤代烯烃为11-溴-1-十一烯、11-氯-1-十一烯和16-溴-1-十六烯中的任意一种。
3.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的溶剂为异丙醇、丙酮和乙醇中的一种或几种。
4.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的阻聚剂为对苯二酚。
5.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的乳化剂由质量百分比为60~80%的非离子型乳化剂和20~40%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯、椰油脂肪酸二乙醇酰胺和失水山梨醇单硬脂酸酯中的一种或几种的混合物;所述的阳离子型乳化剂为十六烷基三甲基溴化铵和十二烷基苯磺酸钠中的一种或两种。
6.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的引发剂为2,2-偶氮二(2-甲基丙基咪)二盐酸盐、偶氮二异丁腈和过硫酸铵中的任意一种。
7.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的交联剂为N,N-亚甲基双丙烯酰胺。
8.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的催化剂为双组分齐格勒纳塔催化剂,用量为双子季铵盐用量的0.15-0.3wt%。
9.根据权利要求8所述的一种非溶出型抗菌整理剂,其特征在于:所述的催化剂为TiCl4-Al(C2H5)3。
10.根据权利要求1~9任一项所述的非溶出型抗菌整理剂的制备方法,其特征在于,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
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