CN1297499A - 用作改进纺织品抗菌剂的酯化triclosan衍生物 - Google Patents
用作改进纺织品抗菌剂的酯化triclosan衍生物 Download PDFInfo
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Abstract
本发明涉及由单根纤维组成的织物,酯化的triclosan已扩散到单根纤维内。该方法赋予纺织品长期持久的抗菌、杀菌和杀真菌性能,这是迄今为止单独用triclosan无法得到的。
Description
技术领域
本发明涉及由单根纤维组成的织物,其中酯化triclosan已扩散到纤维内。该方法赋予纺织品长期持久的抗菌、杀菌和杀真菌性能,这是迄今为止单独用triclosan所不能达到的。
技术背景
近年来,人们一直对每天暴露所产生的潜在抗菌污染的危害给予了很大的关注。这种担忧的值得注意的实例包括,在快餐厅中未烹调牛肉中发现的由某些Eschericia coli菌株产生的食物中毒的致命后果;由未烹调和未清洗的家禽食物产品的沙门氏菌污染引起的疾病;以及由葡萄球菌属耳(aureus),酵母和其它单细胞生物体引起的疾病和皮肤感染。随着消费者对这方面兴趣的增加,制造商们已经开始将诸如triclosan(由Ciba-Geigy市售,商标为Irgasan)的抗菌剂加入到家用产品中。例如,一些品牌的聚丙烯切菜板、液体肥皂等都含有这种非常有效的抗菌化合物。一般来说,在液体或聚合物介质中加入triclosan是比较容易的。然而,长期来人们觉得有必要在纺织品中,尤其是服装织物中提供有效的,持久的和长期的抗菌性能,所述服装织物极难用triclosan达到上述性能。有一些市售的纺织产品,包括用triclosan复合(co-extruded)的丙烯酸和/或乙酸酯纤维(例如HoechstCelanese出售的商标为MicrosafeTM的这种乙酸酯织物和Courtaulds出售的商标为AmicorTM的这种丙烯酸聚合物织物)。但是,这些应用局限于上述那些类型的纤维,triclosan对聚酯、聚酰胺、棉、合成弹力纤维等织物,并且在这些织物内不起作用。此外,所述的复合方法非常昂贵,尤其在与本发明方法相比时。
Triclosan及其衍生物,以及这些化合物所具有的抗菌性能已经在Model等的美国专利3,506,720及美国专利3,904,696中,Noguchi等的美国专利3,929,903和Bindler等的瑞士专利459,656中说明,这些专利均被引入本发明作为参考。这些专利还说明了加入triclosan及triclosan衍生物的纺织品表面处理,以赋予服装布暂时的抗菌性能。因Triclosan及其衍生物以及它们的分散体对皮肤的低毒性和高水平的抗菌活性,杀菌活性等,其是最值得注意的优良的纺织品处理剂。然而,由于其在高温的挥发性,以及在高pH值水性介质中的高溶解性,很少的几次洗衣后,triclosan有容易从织物基材上洗掉的倾向。还有,如上所述,氯漂白剂容易与triclosan反应,因而降低了triclosan的抗菌能力。加入包括一些酯化产品的triclosan及其衍生物的纺织品处理已在Berth等的美国专利3,753,917和Bindler的瑞士专利450,347中公开,这两个专利均被引入本发明作为参考。这些专利都没有明确提出triclosan酯在织物的单根纤维内的特殊扩散,从而,给织物基材提供长期的抗菌,杀真菌和杀菌等作用的过程。瑞士专利讨论了浸渍织物,但这种处理只是填充纱线之间间隙的表面应用(如纤维和纺织品技术词典所定义的)。本发明方法与现有技术之间的不同是非常明显的,因为为了在每根单根纤维内充分引入triclosan,扩散需要在很高的温度下进行。此外,对标准清洗操作的持久性来说,在该文献中讲述的施加于织物的triclosan及triclosan衍生物的量太少。这样,仍没有关于给纺织品织物提供长期抗菌处理的说明和明确建议。因此,在纺织品工业中仍有必要给织物提供一种抗菌triclosan衍生物的应用,这种应用是持久的,通过标准清洗技术是难以消除的,在与氯漂白剂接触时不易与其反应而影响其抗菌程度,并且使triclosan基化合物在织物的整个使用期间都基本上保持其全部的抗菌性能。
发明公开
因此,本发明的目的是给纺织品基材提供一种改进的,长效抗菌整理剂。本发明的另一个目的是提供一种相对便宜的方法,在织物的制造和/或染色过程中,在单个根的纺织纤维内渗入tri2closan酯以赋予织物持久的和长期的杀菌,杀真菌和抗菌性能。本发明的还一个目的是为服装工业提供一种织物,这种织物能使其中的抗菌化合物保持在至少25次的洗衣周期内(相当于隔周洗一次一年的时间)。本发明的再一个目的是提供一种用于食品服务业的抗菌织物,例如亚麻台布,餐桌用布等,这种抗菌织物在服装内不必要。
所以,本发明涉及一种赋予织物长期抗菌性能的方法,该方法顺序包括下述步骤:
(a)提供至少一种triclosan酯衍生物;和
(b)在一定的温度下,将所述triclosan酯衍生物与纺织品接触足够长的时间以实现所述triclosan酯衍生物在所述纺织品的单根纤维内的扩散。
此外,本发明还涉及一种赋予织物长期抗菌性能的更具体的方法,该方法顺序包括下述步骤:
(a)提供一种triclosan酯衍生物;
(b)将所述triclosan酯衍生物加入到染色浴中,其中所述的染色浴含有至少一种纺织品染料;
(c)将所述纺织品加入到所述染色浴中;
(d)在标准染色浴压力下,搅拌所述染色浴并将所述染色浴的温度升至一定的温度,保温足够长的时间,以实现所述triclosan酯衍生物和所述染料在所述纺织品的单根纤维内的扩散;和
(e)从所述染色浴中取出已处理的纺织品。
现有技术中没有公开或实施这种使用triclosan酯衍生物的特殊的方法。优选地,在把triclosan酯加入染色浴之前,通过加入表面活性剂,如Union Carbide制造的TritonTMX-301,使triclosan酯在水性介质中扩散。优选的染色浴是由喷射染色机,如Hisaka喷射染色机构成。
本发明计划使用任何triclosan酯衍生物。考虑到它们的容易制备性以及它们赋予织物的抗菌性能的有效性,优选的triclosan酯衍生物为triclosan乙酸酯、triclosan丙酸酯、triclosan苯甲酸酯、triclosan-4-硝基苯甲酸酯和triclosan己酸酯。上述列示仅表示本发明的一组优选化合物,并不限制其范围。本发明也计划使用纺织喷射染色法中使用的任何标准的染料、颜料或着色剂。为了加入triclosan酯衍生物处理,可能需要将染料或着色剂的量从常用量调节到补偿量。在某些情况下,相信triclosan酯衍生物在染料浴中起到了一种类型增塑剂的作用,帮助染料在纺织纤维中扩散。
纺织品基材本身可以由机织织物、非机织织物或针织织物制成,并且可以由天然或人造纤维制成。纤维的实例包括但不限于:棉、聚酯、聚酰胺、苎麻、乙酸酯、聚烯烃、丙烯酸、合成弹力纤维或其混合物。其中聚酯、聚酰胺(特别是尼龙(-6或-6,6))、和弹力纤维,尤其是尼龙和弹力纤维的混合物为优选。另外,特别优选的纺织品是那些针织品。持久的,长期的抗菌性能在这些优选的纺织品基材中最为明显。
如上所述,该方法本身需要足够高的温度和持久的暴露,以完成上染率和随后的triclosan酯在纺织品基材的单根纤维内的扩散。该方法的优选温度范围大约为80-130℃,更具体的温度取决于要消耗的特定酯衍生物和要处理的特定纺织品。例如,在大约120℃时triclosan乙酸酯在针织品聚酯纤维以及针织品尼龙和弹力纤维的混合物内扩散较好。如果温度太低,扩散不能进行。需要的时间周期一般范围为大约10-120分钟,具体取决于要扩散的酯衍生物和要处理的织物。此外,仅作为一个例子,在120℃时需要20分钟triclosan乙酸酯才足以在聚酯针织品和尼龙/弹力纤维混合物针织品内扩散。
织物完全实现所希望的长期抗菌性能的所必需的triclosan酯衍生物的量取决于实际要处理的织物的数量。因此,染料浴内的织物重量和triclosan酯衍生物重量之间的重量百分比的比值应为大约100∶0.01-100∶1。该范围优选为大约100∶0.03-100∶0.6,最优为大约为100∶0.1-100∶0.25。
在织物内加入酯的具体步骤进一步包括加热设定、上浆(slashing)以及其它任何方法,这些方法可以包括充分加热并有足够的时间使酯在要处理的织物单根纤维内扩散。
实际上,triclosan酯的使用仅是在织物基材内施加和扩散triclosan的有效方式。相信用triclosan酯处理的纺织品的抗菌性能可以从triclosan化合物本身获得,该triclosan化合物是在含水或含湿环境中通过酯的水解非常缓慢地产生的。因此,本方法在提供抗菌性能以及提供持久的抗菌扩散纤维整理剂方面极为有效。Triclosan由下式(Ⅰ)表示:这种具有自由羟基的化合物容易在高pH值下溶解于水中。Triclosan在高温下还具有挥发倾向。
下式(Ⅱ)表示了具有triclosan酯化的羟基基团的优选的酯衍生物:其中R选自C1-C10烷基或环烷基、芳基和取代的芳基。具体地,优选的化合物是triclosan乙酸酯、triclosan丙酸酯、triclosan苯甲酸酯、triclosan 4-硝基苯甲酸和triclosan己酸酯。特别优选的是triclosan乙酸酯。在另一个实施方案中,R是磷酸酯基团以便形成triclosan磷酸酯。由式(Ⅱ)定义的化合物不溶于水,并且其挥发性一般较triclosan本身低得多。例如,triclosan及triclosan乙酸酯的热重分析表明了这种挥发性的本质不同,如下表所示。
表
热重分析
用Perkin-Elmer TGA 7获得试样的重量百分数损失的测量值,其中Perkin-Elmer TGA 7以20℃/分钟的速度从40-250℃扫描温度。在对每个样品的温度扫描完成时得到下列结果:
试样 重量损失百分数%
Triclosan 62
Triclosan乙酸酯 12
这种特定酯衍生物的亲油性促进了其在疏水纤维表面的尽染作用(exhaustion)并且进一步促进了其在每根单根纤维中的扩散。相反,具有自由羟基部分的triclosan本身在含水染料浴中不容易上染到纤维表面,且不能明显地扩散到单根纤维中。因此,这种在单根纤维内扩散的能力提供了这样一种方式,即在织物上和织物内形成少量但是抗菌有效量的triclosan。清洗和漂白,特别是用粗氯化试剂的清洗和漂白不会影响所述酯的耐久性和抗菌性。总之,储如在织物的细隙内单一涂布或浸渍triclosan酯或triclosan本身的表面处理应用,在洗衣周期中容易被高pH值的洗涤剂溶液除去,因此这种表面处理应用不能给纺织品提供持久的,长期的抗菌处理。而在织物的纤维内扩散的triclosan酯不与清洗液接触,因此不容易被除去。然而,纤维内的triclosan酯具有以很低的速度迁移到纤维表面的能力以在基材上提供抗菌作用。Triclosan与其酯衍生物之间不同之处的另一个重要方面是这样一个已知事实,即吸入triclosan会对神经***隔膜产生刺激。以本特定含量并以本发明方式使用Triclosan酯衍生物没有表现出有毒的和潜在有害的问题。由于是在织物基材上存在的triclosan酯水解形成少量的但是抗菌的效的triclosan,所以这个问题不成其大的担忧。然而,如果真要为了使织物能实现长期抗菌性能而单独使用triclosan,所需要的大量的化合物很可能对人体造成严重的健康伤害。
任何其它的纺织添加剂,如染料、浆纱化合物、紫外线吸收剂和柔软剂也可以导入要处理的织物基材内或加到要处理的织物基材的表面。加入到本发明织物中的特别希望作为可选择的整理剂是污垢隔离剂,该污垢隔离剂可以改善织物的润湿性和可洗性。优选的污垢隔离剂包括那些能给聚酯表面提供亲水性的物质。织物具有这种改性的表面,还能通过毛细润湿作用赋予穿着者更舒适的感觉。本发明计划使用的优选污垢隔离剂可以在下列文献中找到:美国专利US3377249、US3535151、US3540835、US3563795、US3574620、US3598641、US3620826、US3632420、US3694165、US3650801、US3652212、US3660010、US3676052、US3690942、US3879206、US3918807、US3625754、US4014857、US4073993、US4090844、US4131550、US4164392、US4168954、US4207071、US4290765、US4068035、US4427557和US4937277。这些专利已被引入本发明作为参考。
已处理的织物可以制作衣服、亚麻台布、浴室用帘布、家用亚麻布、条纹毛巾或任何其它类型的希望有抗菌性能的织物。
本发明的triclosan酯可以通过上述的美国专利3,904,696公开的方法制备,本发明已全部引入作为参考。
本发明的最佳实施方式
下面的实施例是表示使用和应用本发明方法的优选实施方案:
实施例1
通过扩散应用triclosan酯
将等量triclosan乙酸酯(2,4,4’-三氯基-2’-乙酸基-二苯基酯)和TritonTMX-301在搅拌下加入一个烧瓶中。将50%(重量百分比)的水加入到混合物中,获得含量为50%(重量百分比)的稳定的triclosan乙酸酯分散体。然后将该分散体注入到Hisaka喷射染色机中。再将尼龙/合成弹力纤维为50/50的混合针织织物加入到染色机中,其中织物与酯的比值(重量百分比)为100∶0.1。关闭染色机,搅拌,加热至大约120℃的温度约20分钟,再使其冷却至室温。从染色机中取出织物,干燥并分析其抗菌性能。使用AATCC测试法147-1993对葡萄球菌属aureus测试时,该织物表现出100%的接触抑制和3mm的区域抑制。然后使该织物经受相当于25次标准家用清洗,随后测试相同的接触抑制和区域抑制。25次清洗后,织物保持相同水平的对葡萄球菌属aureus的接触抑制并表现出对葡萄球菌属aureus的1mm的区域抑制。
实施例2
通过扩散应用triclosan酯
除要处理的织物是重量为6oz/td2的每根长丝纱线0.7旦的100%聚酯针织物且织物与酯的比值(重量百分比)为100∶0.25外,使用的步骤与实施例1的相同。另外,对葡萄球菌属aureus测试时,0次清洗和25次清洗后获得的接触抑制和区域抑制的结果相同。
实施例3(对比试验)
通过浸渍应用triclosan
根据只在瑞士专利459656中描述的方法,用triclosan浸渍纺织品并分析其长期的抗菌性能。
UltrafreshNM,一种从加拿大多伦多汤普森研究所(ThomsonResearch Associates,Toronto,Canada)得到的3%活性triclosan分散体,用水将其稀释至含0.15%活性triclosan。用该溶液将上述实施例2使用的相同织物浸透并压成大约100%的溶液吸收。然后在对流炉中立即将织物在320°F的温度下干燥3分钟。使用AATCC测试法147-1993对葡萄球菌属aureus测试时,该处理的织物表现出7mm的区域抑制和100%的接触抑制。然而,5次常规清洗和干洗周期后,该织物表现出无区域抑制和0%的接触抑制。
实施例4
通过浸渍应用triclosan乙酸酯
根据只在瑞士专利459656中描述的方法,用triclosan酯,乙酸酯浸渍纺织品并分析其长期的抗菌性能。
将实施例1使用的相同triclosan乙酸酯分散体稀释到含0.15%活性酯。然后用稀释的溶液浸透实施例2中使用的相同聚酯(聚乙烯对苯二酸酯)织物,并压至大约100%的溶液吸收。再立即在对流炉中将织物在320°F的温度下干燥3分钟。使用AATCC测试法147-1993对葡萄球菌属aureus测试时,该处理的织物表现出4mm的区域抑制和100%的接触抑制。5次常规清洗和干洗周期后,该织物表现出无区域抑制和0%的接触抑制。
当然,有许多可选择的实施方案和改进都包括在本发明下述的权利要求的精神和范围内。
Claims (20)
1.一种赋予织物长期抗菌性能的方法,依次包括下列步骤:
(a)提供至少一种triclosan酯衍生物;且
(b)在一定的温度下,将所述triclosan酯衍生物与纺织品接触足够长的时间以实现所述triclosan酯衍生物在所述纺织品的单根纤维内的扩散。
2.权利要求1所述的方法,其中所述triclosan酯衍生物选自triclosan乙酸酯、triclosan丙酸酯、triclosan苯甲酸酯、triclosan 4-硝基苯甲酸酯和triclosan己酸酯。
3.权利要求2所述的方法,其中所述triclosan酯衍生物是triclosan乙酸酯。
4.权利要求1所述的方法,其中所述纺织品选自机织织物、非机织织物或针织织物。
5.权利要求4所述的方法,其中所述织物包括天然或人造纤维或两者的混合物。
6.权利要求5所述的方法,其中所述纺织品包括选自棉纱、聚酯、聚酰胺、乙酸酯、苎麻、尼龙、聚烯烃、丙烯酸、合成弹力纤维及其混合物的纤维。
7.权利要求5所述的方法,其中所述纺织品包括选自聚酯、尼龙、合成弹力纤维及其混合物。
8.权利要求1所述的方法,其中所述纺织品与triclosan酯衍生物的重量比大约为100∶0.03-100∶1。
9.权利要求8所述的方法,其中所述纺织品与triclosan酯衍生物的重量比大约为100∶0.1-100∶0.25。
10.权利要求1所述的方法,其中步骤(b)的温度在大约80-130℃,并且步骤(b)持续的时间范围大约为10-120分钟。
11.权利要求1所述的方法,其中在步骤(a)之前,所述triclosan酯衍生物与表面活性剂扩散于水中。
12.一种赋予织物长期抗菌性能的方法,依次包括下列步骤:
(a)提供一种triclosan酯衍生物;
(b)将所述triclosan酯衍生物加入到染色浴中,其中所述的染色浴含有至少一种纺织品染料;
(c)将一种纺织品加入所述染色浴中;
(d)在标准染色浴压力下,搅拌所述染色浴并将所述染色浴的温度升至一定的温度,保持足够长的时间,以实现所述triclosan酯衍生物和所述染料在所述纺织品的单根纤维内的扩散;和
(e)从所述染色浴中取出所述纺织品。
13.权利要求12所述的方法,其中所述triclosan酯衍生物选自triclosan乙酸酯、triclosan丙酸酯、triclosan苯甲酸酯、triclosan 4-硝基苯甲酸酯和triclosan己酸酯。
14.权利要求13所述的方法,其中所述triclosan酯衍生物是triclosan乙酸酯。
15.权利要求12所述的方法,其中所述纺织品选自机织织物、非机织织物或针织织物。
16.权利要求15所述的方法,其中所述纺织品包括选自棉纱、聚酯、聚酰胺、乙酸酯、苎麻、尼龙、合成弹力纤维及其混合物。
17.权利要求16所述的方法,其中所述纺织品包括选自聚酯、尼龙、合成弹力纤维及其混合物。
18.权利要求12所述的方法,其中所述纺织品与triclosan酯衍生物的重量比大约为100∶0.03-100∶1。
19.权利要求18所述的方法,其中所述纺织品与triclosan酯衍生物的重量比大约为100∶0.1-100∶0.25。
20.权利要求12所述的方法,其中步骤(b)的温度在大约80-130℃,并且步骤(d)持续的时间范围大约为10-120分钟。
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US09/027,045 | 1998-02-20 | ||
US09/027,045 US5968207A (en) | 1998-02-20 | 1998-02-20 | Esterified triclosan derivatives as improved textile antimicrobial agents |
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CN100336968C CN100336968C (zh) | 2007-09-12 |
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US (3) | US5968207A (zh) |
EP (1) | EP1056901B1 (zh) |
JP (1) | JP3495330B2 (zh) |
CN (1) | CN100336968C (zh) |
AU (1) | AU746470B2 (zh) |
BR (1) | BR9909645A (zh) |
DE (1) | DE69908910T2 (zh) |
WO (1) | WO1999042650A1 (zh) |
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CN105461814A (zh) * | 2015-12-14 | 2016-04-06 | 上海交通大学医学院附属仁济医院 | 一种醋酸纤维素衍生物及其制备方法和用途 |
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- 1999-01-12 JP JP2000532582A patent/JP3495330B2/ja not_active Expired - Fee Related
- 1999-01-12 BR BR9909645-5A patent/BR9909645A/pt not_active IP Right Cessation
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- 1999-01-12 EP EP99902205A patent/EP1056901B1/en not_active Expired - Lifetime
- 1999-10-18 US US09/420,435 patent/US6197072B1/en not_active Expired - Fee Related
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103498272A (zh) * | 2013-09-17 | 2014-01-08 | 上海婉静纺织科技有限公司 | 牛奶蛋白纤维和棉纤维混纺的面料 |
CN103498272B (zh) * | 2013-09-17 | 2015-07-01 | 上海婉静纺织科技有限公司 | 牛奶蛋白纤维和棉纤维混纺的面料 |
CN105461814A (zh) * | 2015-12-14 | 2016-04-06 | 上海交通大学医学院附属仁济医院 | 一种醋酸纤维素衍生物及其制备方法和用途 |
CN105461814B (zh) * | 2015-12-14 | 2018-03-27 | 上海交通大学医学院附属仁济医院 | 一种醋酸纤维素衍生物及其制备方法和用途 |
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EP1056901A4 (en) | 2001-04-11 |
AU746470B2 (en) | 2002-05-02 |
JP3495330B2 (ja) | 2004-02-09 |
JP2002504630A (ja) | 2002-02-12 |
US5968207A (en) | 1999-10-19 |
DE69908910D1 (de) | 2003-07-24 |
AU2224299A (en) | 1999-09-06 |
US6197072B1 (en) | 2001-03-06 |
BR9909645A (pt) | 2002-01-15 |
CN100336968C (zh) | 2007-09-12 |
EP1056901A1 (en) | 2000-12-06 |
DE69908910T2 (de) | 2004-05-19 |
US6299651B1 (en) | 2001-10-09 |
WO1999042650A1 (en) | 1999-08-26 |
EP1056901B1 (en) | 2003-06-18 |
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