CN114832153A - 多糖类织物增强基抗菌止血多功能水凝胶敷料 - Google Patents
多糖类织物增强基抗菌止血多功能水凝胶敷料 Download PDFInfo
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- CN114832153A CN114832153A CN202210487838.2A CN202210487838A CN114832153A CN 114832153 A CN114832153 A CN 114832153A CN 202210487838 A CN202210487838 A CN 202210487838A CN 114832153 A CN114832153 A CN 114832153A
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- anhydride
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Abstract
本发明提供了一种多糖类织物增强基抗菌止血多功能水凝胶敷料，包括水凝胶前驱体溶液和织物，两者体积比为1：2~10；其中水凝胶前驱体溶液中包括按质量份计的酸酐改性的多糖类水凝胶单体40份和酸酐改性的抗菌胍盐1~10份，去离子水100~200份，还包括凝血酶和单宁酸，凝血酶含量为0.3~0.8g/mL，单宁酸含量为0.05~0.25g/mL。本发明制备得到敷料具有优良的抗菌性、止血性及粘附性能，同时具备优良的生物相容性及具有良好的机械性能及柔软性，能加快伤口愈合。
Description
技术领域
本发明属于医用材料及其制备领域，具体涉及一种多糖类织物增强基抗菌止血多功能水凝胶敷料及制备方法。
背景技术
由水不溶性交联聚合物组成的水凝胶，具有三维网络状结构，对于水性介质具有高亲和性。由于其具有亲水的多孔结构，可以吸收大量的水，通过其水分交换活动促进伤口愈合，从而在伤口和敷料之间形成最佳环境，伤口处有凉爽、舒缓的效果。水凝胶还可以装载药物或活性生物分子，控制它们使用和释放赋予水凝胶相应的功能。其生理特性和机械特性与生物组织相似，已广泛应用于组织工程、药物输送、电子皮肤、柔性传感器等领域。
微生物对人类健康构成极大的威胁，细菌伤口感染会导致正常伤口愈合的延迟甚至停止，并可能导致形成慢性无法愈合的伤口；对于传统敷料而言，除了伤口处的血液、伤口处人体还会分泌汗液及油脂，这会导致敷料表面和伤口处极易粘附，不仅抗菌性能和抗菌持久性下降，在除去敷料的同时还有可能形成新的伤口。传统伤口敷料抗菌性能、止血性能以及防粘附性能仍然存在较大的提升空间。
发明内容
本发明提供了一种多糖类织物增强基抗菌止血多功能水凝胶敷料及制备方法，该敷料具有优良的抗菌性、止血性及粘附性能，同时具备优良的生物相容性及具有良好的机械性能及柔软性，能加快伤口愈合。
本发明的技术方案是，一种多糖类织物增强基抗菌止血多功能水凝胶敷料，包括水凝胶前驱体溶液和织物，两者体积比为1：2～10；其中水凝胶前驱体溶液中包括按质量份计的酸酐改性的多糖类水凝胶单体40份和酸酐改性的抗菌胍盐1～10份，去离子水100～200份，还包括凝血酶和单宁酸，凝血酶含量为0.3～0.8g/mL，单宁酸含量为0.05～0.25g/mL。
进一步地，所述织物为涤棉织物、纯棉织物、无纺布、粘胶织物中的一种或几种。所述多糖为葡聚糖、壳聚糖、魔芋葡甘聚糖、海藻酸钠、瓜尔豆胶中的一种或几种。所述抗菌胍盐为分子量在600-6000的聚六亚甲基胍盐酸盐。酸酐为甲基丙烯酸酐和/或马来酸酐。
进一步地，酸酐改性的多糖类水凝胶单体制备时，将多糖加入溶剂中，在保护气环境下溶解，冷却后加入催化剂、酸酐进行反应，加入冷的异丙醇中进行沉淀，后用异丙醇洗涤，干燥即得。
进一步地，所述溶剂为LiCl/DMF溶剂体系，两者质量比为1～10:20；多糖与酸酐的摩尔比为1:1～3；催化剂为三乙胺，催化剂与酸酐的摩尔比为1～10:100。
进一步地，所述冷却温度为40～80℃；加入催化剂后反应10～30分钟，再加入酸酐反应6～10小时，冷的异丙醇温度为2～8℃。
进一步地，所述酸酐改性的抗菌胍盐制备时，采用1,6-己二胺与盐酸胍在保护气环境及加热条件下进行反应，除去反应中产生的NH3，反应结束后将产物真空干燥得六亚甲基胍盐酸盐；将六亚甲基胍盐酸盐与酸酐在有机溶剂混匀，加入三乙胺催化剂反应，所得产物用二氯甲烷萃取，干燥后得到酸酐改性抗菌胍盐。
进一步地，1,6-己二胺与盐酸胍的摩尔比为1:1～10；六亚甲基胍盐酸盐与酸酐质量比为1～5:1，六亚甲基胍盐酸盐与催化剂的质量比为1:0.5～3。
进一步地，1,6-己二胺与盐酸胍反应温度为100～140℃，反应时间为2～4小时；除去反应中产生的NH3后调整温度为160～190℃，反应时间为6～8小时；六亚甲基胍盐酸盐干燥温度为80～110℃，干燥时间为6～8小时；六亚甲基胍盐酸盐与酸酐反应的有机溶剂为DMSO,反应条件为黑暗避光条件下反应20～30小时，反应温度为0～10℃，产物干燥温度为20～25℃。
本发明还涉及制备所述敷料的方法，其特征在于，具备步骤为：
将酸酐改性的多糖类水凝胶单体、酸酐改性的抗菌胍盐、凝血酶、单宁酸和去离子水按比例混匀制备成混合溶液，然后将织物浸泡在混合溶液中，通过紫外光原位交联方式形成敷料；敷料进行预冻及冻干后，消毒杀菌密封保存，即得多糖类织物增强基抗菌止血多功能水凝胶敷料。
进一步地，浸泡温度为室温，时间为10～60分钟；紫外光照时长为10～30分钟；预冻温度为-20～0℃，时间为6～12小时；冻干温度为-60～-40℃，冻干时间为30～40小时。
本发明具有以下有益效果：
1、本发明采用多糖基水凝胶敷料，多糖在自然界分布广，易获得。多糖基水凝胶，溶胀性能好，可吸收大量伤口渗液，提供伤口愈合所需的湿润环境。此外，绝大部分的多糖基水凝胶具有较好的生物降解性和生物相容性，安全性很高，抗原性小，会减少排异反应和炎症反应，有利于伤口的恢复。
2、本发明对多糖和抗菌胍盐均采用酸酐进行改性，然后通过紫外光原位交联方式成胶，仅仅依赖于聚合物分子链上的碳碳双键，不需要引入多余的引发剂或交联剂，因而避免了该类试剂的毒副作用，最大化降低化学毒性，所得产品安全性高，生物毒性小。且改性多糖和改性抗菌胍盐之间能够通过双键形成互穿网络结构，使得多糖基水凝胶与织物复合程度更加紧密，赋予水凝胶抗菌性和抗菌持久性，水凝胶前驱体溶液中加入单宁酸，使水凝胶敷料具有黏附性能；
3、本发明在制备水凝胶敷料时，将初步形成的水凝胶敷料放在冰箱里预冻，然后冻干，得到具有良好的机械性能和柔软性能且不用添加其他防腐剂的成品。再经紫外消毒杀菌密封保存包装。使用时加入适量去离子水，置于伤口上即可。
4、本发明的改性葡聚糖单体为带双键的葡聚糖，采用织物增强水凝胶敷料，通过紫外光交联技术复合织物与水凝胶，其中水凝胶在织物中形成互穿网络物理作用，能够提升敷料的力学性能。本发明的抗菌胍盐与水凝胶单体在光引发剂条件下照射紫外光，使自由基聚合，水凝胶敷料具有良好的抗菌性和抗菌持久性。单宁酸的添加使得敷料具有黏附性能，同时在敷料中载入凝血酶药物，除了水凝胶本身的良好吸收渗液能力，药物直接作用于血液中的可溶性纤维蛋白原，将其激活为不可溶性能的纤维蛋白，促进血凝块的形成，止血时间更快速，止血效果更明显。
附图说明
图1为实施例1中酸酐改性葡聚糖合成示意图。
图2为实施例1中聚六亚甲基胍盐酸盐合成示意图。
图3为实施例1中酸酐改性抗菌胍盐合成示意图。
图4为实施例1中水凝胶合成示意图。
图5为实施例1中多糖类织物增强基抗菌止血多功能水凝胶敷料形成示意图。
图6为实施例1和实施例2中制备水凝胶敷料的溶胀率对比图。
图7为样品抗菌图，从左到右分别为空白对照样、未添加抗菌胍盐组分样品、添加0.02g抗菌胍盐组分样品和添加0.06g抗菌胍盐组分样品。
图8为小鼠断尾模型止血数据图，A、B、C分别为凝血酶量为2IU/mL、20IU/mL、200IU/mL。
具体实施方式
下面将结合实施例对本发明的实施方案进行详细描述，但是本领域技术人员将会理解，下列实施例仅用于说明本发明，而不应视为限定本发明的范围。
实施例1
步骤1：改性葡聚糖的制备
在90℃高温条件下，将4g葡聚糖(图1中结构式1)单体(Mw＝70000，与酸酐的摩尔比为6：1)溶解于100mL氯化锂和N,N’-二甲基甲酰胺的混合溶液中(氯化锂含量为10wt％)，通氮气溶解。待葡聚糖完全溶解后，溶液冷却至70℃，将三乙胺催化剂(0.36g)加入到葡聚糖溶液中，磁力搅拌10分钟，加入酸酐(图1结构式2)(5.5g)在氮气的保护下反应10小时。反应混合物在2℃的异丙醇中沉淀析出，用异丙醇洗涤三次，沉淀，过滤，干燥，得到产物(图1结构式3)。
步骤2：改性抗菌剂的制备
称取1,6-己二胺(图2结构式4)(29.0g)与盐酸胍(图2结构式5)(24.0g)在氮气的保护下充分搅拌，在120℃条件下反应2h，除去反应产生的氨气。随后将温度调整为180℃反应6h并持续搅拌，反应结束后趁热倒出，在真空干燥箱中100℃真空干燥6h，得到产物聚六亚甲基胍盐酸盐(PHMG)(图2结构式6)。
将聚六亚甲基胍盐酸盐(PHMG)(5.0g)与酸酐(2.0g)溶于20mL DMSO，充分搅拌至混合质均匀。在0℃下，加入三乙胺(2.0g)黑暗避光条件下反应24h。所得产物用二氯甲烷萃取三次，室温下真空干燥，得到改性聚六亚甲基胍盐酸盐(M-PHMG)(图3结构式7)。
步骤3：多糖类织物增强基抗菌止血多功能水凝胶敷料的制备：
将经过改性的葡聚糖单体(0.4g)、抗菌胍盐(0.06g)、凝血酶(20IU/mL)、单宁酸(0.2g)溶于去离子水(2mL)得到混合溶液，将混合溶液浸泡在织物中，通过紫外光原位交联方式形成敷料。将所得到的多糖类水凝胶敷料冻干后，再紫外消毒杀菌密封保存。
实施例2
该实施例主要同实施例1，区别在于：
步骤1为：
在90℃高温条件下，将4g葡聚糖单体溶解于100ml氯化锂和N，N’-二甲基甲酰胺的混合溶液中(氯化锂含量为10wt％)，通氮气溶解。待葡聚糖完全溶解后，溶液冷却至70℃，将三乙胺催化剂(0.36g)加入到葡聚糖溶液中，磁力搅拌10分钟，加入酸酐(11g)在氮气的保护下反应10小时。反应混合物在2℃的异丙醇中沉淀析出，用异丙醇洗涤数次，沉淀，过滤，干燥，得到产物。
实施例3
该实施例主要同实施例1，区别在于：
步骤1为：
在90℃高温条件下，将4g葡聚糖单体溶解于100ml氯化锂和N，N’-二甲基甲酰胺的混合溶液中(氯化锂含量为10wt％)，通氮气溶解。待葡聚糖完全溶解后，溶液冷却至70℃，将三乙胺催化剂(0.36g)加入到葡聚糖溶液中，磁力搅拌10分钟，加入酸酐(16.5g)在氮气的保护下反应10小时。反应混合物在2℃的异丙醇中沉淀析出，用异丙醇洗涤数次，沉淀，过滤，干燥，得到产物。
实施例4
该实施例主要同实施例1，区别在于：
步骤2为：
称取1,6-己二胺(29.0g)与盐酸胍(12.0g)在氮气的保护下充分搅拌，在120℃条件下反应2h，除去反应产生的氨气。随后将温度调整为180℃反应6h并持续搅拌，反应结束后趁热倒出，在真空干燥箱中100℃真空干燥6h，得到产物聚六亚甲基胍盐酸盐(PHMG)。
将聚六亚甲基胍盐酸盐(PHMG)(5.0g)与酸酐(2.0g)溶于20mL DMSO，充分搅拌至混合质均匀。在0℃下，加入三乙胺(2.0g)黑暗避光条件下反应24h。所得产物用二氯甲烷萃取三次，室温下真空干燥，得到抗菌胍盐(M-PHMG)。
实施例5
该实施例主要同实施例1，区别在于：
步骤2为：
称取1,6-己二胺(29.0g)与盐酸胍(24.0g)在氮气的保护下充分搅拌，在120℃条件下反应2h，除去反应产生的氨气。随后将温度调整为180℃反应6h并持续搅拌，反应结束后趁热倒出，在真空干燥箱中100℃真空干燥6h，得到产物聚六亚甲基胍盐酸盐(PHMG)(图2结构式6)。
将聚六亚甲基胍盐酸盐(PHMG)(5.0g)与酸酐(1.0g)溶于20mL DMSO，充分搅拌至混合质均匀。在0℃下，加入三乙胺(2.0g)黑暗避光条件下反应24h。所得产物用二氯甲烷萃取三次，室温下真空干燥，得到改性聚六亚甲基胍盐酸盐(M-PHMG)。
实施例6
该实施例主要同实施例1，区别在于：
步骤3为：
将经过改性的葡聚糖单体(0.4g)、抗菌胍盐(0.02g)、凝血酶(20IU/mL)、单宁酸(0.2g)溶于去离子水(2ml)得到混合溶液，将混合溶液浸泡在织物中，通过紫外光原位交联方式形成敷料。将所得到的多糖类水凝胶敷料冻干后，再紫外消毒杀菌密封保存。
实施例7
该实施例主要同实施例1，区别在于：
步骤3为：
将经过改性的葡聚糖单体(0.4g)、抗菌胍盐(0.06g)、凝血酶(20IU/mL)、单宁酸(0.5g)溶于去离子水(2ml)得到混合溶液，将混合溶液浸泡在织物中，通过紫外光原位交联方式形成敷料。将所得到的多糖类水凝胶敷料冻干后，再紫外消毒杀菌密封保存。
实施例8
该实施例主要同实施例1，区别在于：
步骤3为：
将经过改性的葡聚糖单体(0.4g)、抗菌胍盐(0.06g)、凝血酶(2IU/mL)、单宁酸(0.2g)溶于去离子水(2ml)得到混合溶液，将混合溶液浸泡在织物中，通过紫外光原位交联方式形成敷料。将所得到的多糖类水凝胶敷料冻干后，再紫外消毒杀菌密封保存。
实施例1制备的水凝胶敷料记为gel-1，实施例2制备的水凝胶敷料记为gel-2，两者的溶胀率如图6所示，其中gel-1溶胀率为23.05，gel-2溶胀度为3.85。
结论：酸酐的投入量越大，水凝胶内部交联越致密，溶胀性能越小。
图7为样品抗菌图，从左到右分别为空白对照样、未添加抗菌胍盐组分样品(其他原料投入量与实施例1相同)、添加0.02g抗菌胍盐组分样品(实施例6)和添加0.06g抗菌胍盐组分样品(实施例1)，其中，未添加抗菌胍盐组分样品、添加0.02g抗菌胍盐组分样品和添加0.06g抗菌胍盐组分样品对大肠杆菌抑菌率分别为84.77％、91.74％、99.98％；对金黄色葡萄球菌的抑菌率分别为80.16％、86.51％、99.84％。
具体试验方法：根据根据GB/T 20944.3-2008进行水凝胶的定量抗菌测试。以大肠杆菌和金黄色葡萄球菌为测试菌种，在测试前对实验所需要用到的实验仪器和配制溶液均进行高温高压灭菌处理。首先，用接种环取一定量的细菌于20mL灭过菌的营养肉汤中，37℃下振荡培养18h。然后稀释菌液至1×104CFU/mL。取0.5mL菌液于营养肉汤中，稀释100倍后取0.5mL至4.5mL PBS溶液中，稀释10倍；再取稀释后的5mL菌液于45mL PBS溶液中，稀释10倍；最后取稀释后的0.5mL菌液至含有70mL PBS溶液的锥形瓶中。将水凝胶样品加入上述稀释后的菌液中作为试验样，不加样品作为空白对照样。将试验样和空白对照样一起移入恒温培养空气摇床中37℃下振荡培养18h。再取0.5mL锥形瓶中的菌液于4.5mL PBS溶液中进一步稀释，重复该步骤5～7次。稀释完成后，从每个稀释倍数的菌液中吸取0.5mL与15mL灭菌处理后的营养琼脂培养液在培养皿中混合均匀，冷却凝固。倒置放入生化培养箱中，37℃下培养18～24h。取出进行菌落计数。抑菌率公式如式1-1所示：
结论：抗菌胍盐的投料比越大，水凝胶敷料的抗菌效果越好。当抗菌胍盐组分质量占水凝胶总质量的2.4％时，葡聚糖基抗菌水凝胶对大肠杆菌和金黄色葡萄球菌的抑菌率分别达到99.98％和99.84％以上，具有优异的抗菌性。
图8为体外凝血效果实验数据图，A、B、C分别为凝血酶量为2IU/mL(实施例8)、20IU/mL(实施例1)、200IU/mL(除凝血酶量不同外，其余同实施例1)。A、B、C的止血时间分别为132.8s，6.67s，3.24s。
具体测试方法：将凝血酶活性分别配比为2IU/mL、20IU/mL、200IU/mL，将装有1mL抗凝鼠血的试管放于37℃的震荡水槽中加热3～6min，向试管中加入不同活性的凝血酶溶液，每3～5s将试管倾斜，观察血液的凝固状态，记录止血时间。
结论凝血酶的投料比越大，凝血效果越好。
以上仅为本发明的优选实施例，并非因此限制本发明的专利范围，对于本领域的技术人员来说，本发明可以有各种更改和变化。凡在本发明的精神和原则之内，所做的任何修改、同等替换、改进等，均应包括在本发明的专利保护范围内。
Claims (10)
1.一种多糖类织物增强基抗菌止血多功能水凝胶敷料，其特征在于，包括水凝胶前驱体溶液和织物，两者体积比为1：2~10；其中水凝胶前驱体溶液中包括按质量份计的酸酐改性的多糖类水凝胶单体40份和酸酐改性的抗菌胍盐1~10份，去离子水100~200份，还包括凝血酶和单宁酸，凝血酶含量为0.3~0.8g/mL，单宁酸含量为0.05~0.25g/mL。
2.根据权利要求1所述的敷料，其特征在于：所述织物为涤棉织物、纯棉织物、无纺布、粘胶织物中的一种或几种；所述多糖为葡聚糖、壳聚糖、魔芋葡甘聚糖、海藻酸钠、瓜尔豆胶中的一种或几种；所述抗菌胍盐为分子量在600-6000的聚六亚甲基胍盐酸盐；酸酐为甲基丙烯酸酐和/或马来酸酐。
3.根据权利要求1或2所述的敷料，其特征在于：酸酐改性的多糖类水凝胶单体制备时，将多糖加入溶剂中，在保护气环境下溶解，冷却后加入催化剂、酸酐进行反应，加入冷的异丙醇中进行沉淀，后用异丙醇洗涤，干燥即得。
4.根据权利要求3所述的敷料，其特征在于：所述溶剂为LiCl/DMF溶剂体系，两者质量比为1~10:20；多糖与酸酐的摩尔比为1~10：1；催化剂为三乙胺，催化剂与酸酐的摩尔比为1～10:100。
5.根据权利要求3所述的敷料，其特征在于：所述冷却温度为40～80℃；加入催化剂后反应10～30分钟，再加入酸酐反应6～10小时，冷的异丙醇温度为2～8℃。
6.根据权利要求1或2所述的敷料，其特征在于：所述酸酐改性的抗菌胍盐制备时，采用1,6-己二胺与盐酸胍在保护气环境及加热条件下进行反应，除去反应中产生的NH3，反应结束后将产物真空干燥得六亚甲基胍盐酸盐；将六亚甲基胍盐酸盐与酸酐在有机溶剂混匀，加入三乙胺催化剂反应，所得产物用二氯甲烷萃取，干燥后得到酸酐改性抗菌胍盐。
7.根据权利要求5所述的敷料，其特征在于：1,6-己二胺与盐酸胍的摩尔比为1:1~10；六亚甲基胍盐酸盐与酸酐质量比为1~5:1，六亚甲基胍盐酸盐与催化剂的质量比为1:0.5～3。
8.根据权利要求5所述的敷料，其特征在于：1,6-己二胺与盐酸胍反应温度为100～140℃，反应时间为2～4小时；除去反应中产生的NH3后调整温度为160～190℃，反应时间为6～8小时；六亚甲基胍盐酸盐干燥温度为80～110℃，干燥时间为6～8小时；六亚甲基胍盐酸盐与酸酐反应的有机溶剂为DMSO,反应条件为黑暗避光条件下反应 20～30 小时，反应温度为 0～10 ℃，产物干燥温度为20~25℃。
9.制备权利要求1~8任意一项所述敷料的方法，其特征在于，具备步骤为：
将酸酐改性的多糖类水凝胶单体、酸酐改性的抗菌胍盐、凝血酶、单宁酸和去离子水按比例混匀制备成混合溶液，然后将织物浸泡在混合溶液中，通过紫外光原位交联方式形成敷料；敷料进行预冻及冻干后，消毒杀菌密封保存，即得多糖类织物增强基抗菌止血多功能水凝胶敷料。
10.根据权利要求9所述的方法，其特征在于：浸泡温度为室温，时间为10~60分钟；浸泡完成后进行紫外光照时长为10～30分钟；预冻温度为-20~0 ℃，时间为6~12小时；冻干温度为-60~-40 ℃，冻干时间为30~40小时。
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