CN1212384C - 可杀灭假单胞菌属微生物的含烷基多聚葡糖苷的消毒剂组合物 - Google Patents
可杀灭假单胞菌属微生物的含烷基多聚葡糖苷的消毒剂组合物 Download PDFInfo
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Abstract
一种消毒清洁组合物,它含杀菌剂、有效量的烷基多糖表面活性剂、至少一种烷基醇和至少一种芳基醇。合适的表面活性剂烷基多糖可含一种或多种糖单元,所述糖单元选自麦芽糖、阿拉伯糖、木糖、甘露糖、半乳糖、葡萄糖、艾杜糖、塔罗糖、阿洛糖、阿卓糖、蔗糖、果糖、山梨糖、左旋糖、乳糖、阿罗糖、塔格糖、阿洛庚酮糖、景天庚酮糖、葡庚酮糖、甘露庚酮糖、古洛庚酮糖、艾杜庚酮糖、半乳庚酮糖、塔罗庚酮糖及它们的衍生物。合适的杀菌剂包括氯己定及其盐、氯酚衍生物、奥替尼啶(CH3-(CH2)7-NHON-(CH2)10-NO-NH(CH2)7-CH2)二盐酸盐或其任何其它盐和季铵化合物。
Description
技术领域
本发明涉及具有消毒作用的清洁剂组合物。
背景技术
已知传染是通过皮肤接触由病原性微生物传播而蔓延的。以往,为抑制这些微生物的存在,已经知道用含表面活性剂的溶液擦洗皮肤然后使用消毒剂。
近年来,已有人提出,在单个操作中使用含杀菌剂和表面活性剂两者的组合物以将清洗作用和消毒作用结合起来将是理想的。然而,业已发现,许多杀菌剂(如氯己定〔N,N-二(4-氯苯基)-3,12-二亚氨基-2,4,11,13-四氮杂十四烷二酰亚胺酰胺〕二葡糖酸盐和其它氯己定盐)与阴离子型表面活性剂不相容,其杀菌活性被非离子型表面活性剂减弱,从而需要添加更多杀菌剂以在使用令人满意的起泡所需的表面活性剂的量的情况下保持足够的杀生物活性。
具体地说,转让给Imperial Chemical Industries公司的美国专利No.3,855,140描述了一种含氯己定的可溶性盐与聚氧乙烯聚氧丙烯嵌段共聚物的洁肤组合物。为使聚合物形成足够的泡沫,必须使用高比例的在20-25%级的量的表面活性剂。从而需要大量的氯己定以保持所需的杀菌活性。这样的大量是不适宜的,因为已知表面活性剂可能对皮肤有不良影响,会使皮肤脱脂,在与杀生物剂(如氯己定)合用时,会对皮肤产生刺激。此外,组合物的成分可能是昂贵的。
因此,提供这样一种组合物将是有益的:在该组合物中,杀菌剂和表面活性剂的量被减少,但仍保持足够的杀菌活性和起泡能力。
在这点上,为提供这样的组合物,国际专利申请WO95/09650提出将酚类消毒剂与烷基多聚葡糖苷表面活性剂组合。然而,如该专利申请所指出的,这样的组合物虽然对大多数微生物显示良好的杀生物活性,但不能对被绿脓杆菌(Pusedomonas aeruginosa,又称绿脓假单胞菌)污染的表面进行消毒,因为这样的组合物对绿脓杆菌无效。
本发明的目的是,基本上克服现有技术的这些缺点。
发明的描述
根据本发明的第一个方面,提供一种含杀菌剂、有效量的烷基多聚葡糖苷表面活性剂、至少一种烷基醇和至少一种芳基醇的消毒清洁组合物。
根据本发明的第二个方面,提供一种对被包括假单胞菌属微生物在内的细菌污染的表面进行去污的方法,该方法包括将该表面与第一个方面所述的消毒清洁组合物接触。
通常,清洁组合物含惰性载体,并可视需要含其它添加剂。
作为烷基多聚葡糖苷的烷基多糖表面活性剂在本领域也是已知的,然而,为便于下面的讨论,下面称该表面活性剂为烷基多糖。
较好的是,组合物中的该表面活性剂的量不超过6%(w/v)。
较好的是,烷基多糖是下式所示烷基多糖:
式中,n是5至19之间的整数,
m是1至3之间的整数。
在上式中,所示的表面活性剂烷基多糖含葡萄糖单元,然而,本发明不限于葡萄糖单元,可用其它糖单元取代葡萄糖单元中的一个或多个。可包含在烷基多糖中的其它糖单元包括麦芽糖、阿拉伯糖、木糖、甘露糖、半乳糖、葡萄糖、艾杜糖.、塔罗糖、阿洛糖、阿卓糖、蔗糖、果糖、山梨糖、左旋糖、乳糖、阿罗糖、塔格糖、阿洛庚酮糖、景天庚酮糖、葡庚酮糖、甘露庚酮糖、古洛庚酮糖、艾杜庚酮糖、半乳庚酮糖、塔罗庚酮糖及它们的衍生物。
合适的杀菌剂包括氯己定及其盐;二邻苄基-对氯苯酚、其它氯酚类衍生物,如对氯-间二甲苯酚、邻苄基-对氯苯酚和邻苯基苯酚、2,4,4-三氯-2-羟基-二苯基醚(三氯生);奥替尼啶(CH3-(CH2)7-NHON-(CH2)10-NO-NH(CH2)7-CH2)二盐酸盐或其任何其它盐和季铵化合物。
氯己定的合适盐包括葡糖酸盐、羟乙磺酸盐、甲酸盐、乙酸盐、谷氨酸盐、琥珀酰胺酸盐、单二甘醇酸盐、二甲磺酸盐、乳酸盐、二异丁酸盐或葡庚糖酸盐。
较好的是,杀菌剂在环境温度下的水溶性至少为0.001%(w/v)。
当杀菌剂为二葡糖酸氯己定时,其使用量最好不超过4.5%(w/v)。当杀菌剂为2,4,4-三氯-2-羟基二苯基醚(三氯生)时,其使用量最好不超过3%(w/v)。
烷基醇最好是低级烷基醇(在本文中,其定义为含少于6个碳原子的醇),如乙醇、异丙醇或正丙醇,最优选异丙醇或正丙醇。醇的含量最好不超过70%(w/v)。当组合物是水性载体(例如用于洗手液)时,醇宜是异丙醇或正丙醇或是它们的组合,其使用量以3-10%(w/v)为佳,最好是4-8%(w/v)。当组合物是醇溶液(例如,用于快速清洁自干溶液),烷基醇最好是55-75%(w/v)。
芳基醇最好是苄醇、苯乙醇、苯氧基乙醇、苯氧基丙醇或它们的氯代衍生物。在应用于皮肤时,优选苯氧基乙醇和苯氧基丙醇。芳基醇的量最好不超过3%(w/v)。
所用的惰性载体可以是例如水或低级醇,如乙醇。
组合物还可含一种或多种下述成分:
(a)增溶剂,如丙二醇、水溶助长剂或它们的混合物。合适的水溶助长剂包括尿素、枯烯磺酸盐、甲苯磺酸盐、二甲苯磺酸盐及乙醇胺柠檬酸盐或其它羟基羧酸盐。
(b)起泡剂,如烷氨基氧化物、烷基单或二乙醇酰胺。起泡剂的例子有月桂基缩合物、或椰子基二乙醇酰胺或单乙醇酰胺缩合物或月桂基或鲸蜡基二甲胺氧化物。
(c)粘度调节剂,如纤维素衍生物、瓜尔树脂和聚羧乙烯。
(d)防腐剂,如咪唑烷基衍生物、脲衍生物(Germabenes)、羟苯甲酸甲酯或羟苯甲酸丙酯(对羟基苯甲酸酯)。
(e)其它常用添加剂,如着色剂、芳香剂、抗氧化剂、润肤剂、增湿剂、稳定剂和增稠剂(如羧甲基纤维素)。
(f)任选的另外的表面活性剂,包括两性表面活性剂、阴离子型表面活性剂和非离子型表面活性剂。合适的另外的表面活性剂包括季铵化合物或小量的高起泡性阴离子型表面活性剂,如月桂基乙氧基磺酸盐、肌氨酸盐、月桂基醚硫酸钠。对另外的成分进行选择以避免与组合物的其它任何成分(尤其是杀菌剂)可能不相容。
组合物的pH通常调节至5-7,最好是5.5,但不限于该pH。当使用氯己定作为杀菌剂时,应避免pH大于8以防止氯己定游离碱沉淀。与组合物相容的大多数有机酸(如乳酸、乙酸和葡糖酸,最好是葡糖酸)可用来调节pH。
在本文中,“包含”一词是含括性的,表示“包括”或“含”,而不是除外性的(“由……组成”或“由……构成”)。
本发明的最佳实施方式
下面的实施例举例说明本发明的实例。它们不应被认为是限定性的。
本领域的技术人员还明白,虽然在此处结合浓度对本发明作了描述,但这样的浓度可在销售或临用之前进行稀释(例如稀释至55%)。
实施例
实施例1-根据WO95/09605的用于比较的组合物
月桂基硫酸钠(100%) 4.67%(w/v)
烷基多糖(100%) 3.92%(w/v)
椰子基三甲铵乙内酯 0.90%(w/v)
三氯生 0.49%(w/v)
丙二醇 0.254%(w/v)
丙三醇 0.254%(w/v)
氯化钠 0.49%(w/v)
柠檬酸 达到10%(w/v)
水 加至100体积%
实施例2-用于比较的市售的含2.0%(三氯生)的杀菌洁肤剂(全部成分未知)
实施例3-用于比较的市售的消毒用外科擦洗组合物
葡糖酸氯己定(CHG) 4.0%(w/v)
非离子型表面活性剂*(100%) 25.00%(w/v)
月桂基二甲胺氧化物(100%) 2.60%(w/v)
水 加至100体积%
(根据Manuf.C/hemist 1973年10月第25至27页和美国专利3,855,140所公开的数据配制)
*聚氧乙烯/聚氧丙烯嵌段共聚物PLURONIC F87(德国BASF公司产品)。
实施例4-本发明的含三氯生的组合物
除加入了5.0%(w/v)的正丙醇和1%(w/v)的苯氧基乙醇之外,其余组分与实施例1的相同。
实施例5-本发明的含三氯生的组合物
除加入了5.0%(w/v)的正丙醇和1%(w/v)的苯氧基乙醇并将三氯生增加至1%(w/v)之外,其余组分与实施例1的相同。
实施例6-本发明的含葡糖酸氯己定的组合物
葡糖酸氯己定(CHG) 2.0%(w/v)
烷基多糖*(100%) 4.00%(w/v)
椰子二乙醇酰胺(100%) 2.00%(w/v)
丙二醇 2.0%(w/v)
异丙醇 8.0%(w/v)
苯氧基乙醇 2.0%(w/v)
水 加至100体积%
*OramixTMNS10 55%(w/v)(法国Sepic SA公司产品)。
实施例7-本发明的含葡糖酸氯己定的组合物
葡糖酸氯己定(CHG) 1.0%(w/v)
烷基多糖*(100%) 4.00%(w/v)
椰子二乙醇酰胺(100%) 0.80%(w/v)
丙二醇 2.0%(w/v)
正丙醇 6.0%(w/v)
苯氧基乙醇 1.0%(w/v)
水 加至100体积%
*可使用任何市售的烷基多糖,如PlantarenTM2000(Henkel公司产品)或AtlasTMG73500(ICI公司产品)。
实施例8-本发明的含三氯生的组合物
三氯生 1.0%(w/v)
烷基多糖*(100%) 4.00%(w/v)
二月桂基醚硫酸钠(100%) 0.20%(w/v)
椰子二乙醇酰胺(100%) 2.00%(w/v)
异丙醇 8.0%(w/v)
丙二醇 10.0%(w/v)
防腐剂** 1.0%(w/v)
苯氧基乙醇 2.0%(w/v)
水 加至100体积%
*OramixTMNS12(法国Sepic SA公司产品)。
**GermabeneTMII 0.2%(w/v)。
实施例9-本发明的含三氯生的组合物
三氯生 1.0%(w/v)
烷基多糖*(100%) 4.00%(w/v)
二月桂基醚硫酸钠(100%) 0.25%(w/v)
枯烯硫酸钠(100%) 4.00%(w/v)
乙醇 4.0%(w/v)
正丙醇 4.0%(w/v)
苯氧基乙醇 1.5%(w/v)
水 加至100体积%
*可使用任何市售的烷基多糖,如PlantarenTM2000(Henkel公司产品)或AtlasTMG73500(ICI公司产品)。
实施例10-本发明的含三氯生的组合物
三氯生 1.00%(w/v)
烷基多糖*(100%) 2.75%(w/v)
椰子二乙醇酰胺(100%) 0.80%(w/v)
二甲苯磺酸钠(100%) 4.00%(w/v)
异丙醇 8.0%(w/v)
丙二醇 2.0%(w/v)
苯氧基乙醇 1.0%(w/v)
羧甲基纤维素 0.6%(w/v)
苯氧基丙醇 1.0%(w/v)
水 加至100体积%
实施例11-本发明的含二邻苄基-对氯苯酚的组合物
二邻苄基-对氯苯酚 1.5%(w/v)
烷基多糖(100%) 4.00%(w/v)
二月桂基醚硫酸钠(100%) 0.20%(w/v)
椰子二乙醇酰胺(100%) 2.00%(w/v)
异丙醇 5.0%(w/v)
苯氧基乙醇 1.0%(w/v)
水 加至100体积%
实施例12-本发明的含二邻苄基-对氯苯酚的组合物
二邻苄基-对氯苯酚 1.5%(w/v)
烷基多糖(100%) 4.00%(w/v)
二月桂基醚硫酸钠(100%) 0.50%(w/v)
椰子二乙醇酰胺(100%) 1.00%(w/v)
乙醇 5.0%(w/v)
苯氧基乙醇 1.0%(w/v)
水 加至100体积%
用三乙醇胺调节pH至7.0-7.2。
在许多微生物的存在下进行悬浮试验(根据欧洲标准CEN/TC216/WG IN)。结果见下表:
表1-悬浮试验
结果表示为:对数减小
试验温度:23℃;接触时间:60秒钟
中和介质:吐温80 100g/L,卵磷脂50g/L,组氨酸1g/L
试验微生物 | E.coliNCTC8196 | S.aureusNCTC4163 | P.aeruginosaNCTC6749 | S.faccalisNCTC775 |
浓度 | 纯净的 | 纯净的 | 纯净的 | 纯净的 |
接触时间(秒) | 60 | 60 | 60 | 60 |
配方 | ||||
用于比较的实施例10..49%(w/v)三氯生 | 不生长 | 不生长 | >2 | >2 |
本发明的实施例40.49%(w/v)三氮生 | 不生长 | 不生长 | 不生长 | 不生长 |
用于比较的实施例22%(w/v)三氯生 | >2 | >2 | >2 | >2 |
本发明的实施例51.0%(w/v)三氯生 | 不生长 | 不生长 | 不生长 | 不生长 |
用于比较的实施例32%(w/v)CHG | 不生长 | 3.8 | 不生长 | 3.9 |
本发明的实施例62.0%(w/v)CHG | 不生长 | 不生长 | 不生长 | 不生长 |
接种浓度 | 2.5×108 | 2.8×108 | 1.3×108 | 1.8×108 |
对实施例10的组合物(1.0%(w/v)三氯生)也进行了悬浮试验。结果如下:
杀菌结果
悬浮试验-30秒钟接触/浓度75%
表示为微生物的对数减少。
微生物
接种物浓度
减少
S.aureus ATTC6538 Log 6.8 >5.8
E.coli ATTC11229 Log 6.9 >5.9
PS.aeruginosa ATTC15442 Log 7.0 >6.0
P.mirabilia ATTC14153 Log 6.8 >6.0
本发明的组合物在比现有普通组合物含量低得多的杀菌剂浓度的情况下具有与现有技术的组合物同等的或更大的杀生物活性且毒性更小。
在较佳实例中,使用6%(w/v)以下的烷基多糖表面活性剂,可使三氯生的量从1.0%成功地减小至0.5%(w/v)而杀生物活性基本上不损失。令人惊奇的是,氯己定的量可从4%减小至2%(w/v)而仍保持良好的杀生物活性和起泡性能。
而且,使用低至2%的烷基多糖,可得到其它常用的表面活性剂所无法得到的足够的起泡洁肤性能。此外,已知的表面活性剂对杀生物剂杀菌性能的干扰被显著降低。
还有,通过包含烷基醇与芳基醇的组合,本发明的组合物可有效地杀灭假单胞菌属微生物。
本发明在美国专利No.3,855,140所述及的领域是一个显著和重要的改进,这可用以下事实进行说明:美国专利No.3,855,140的组合物不能杀灭假单胞菌,而本发明的组合物在含低至0.49%三氯生的情况下可有效地杀灭假单胞菌。
本发明的组合物尤其适合皮肤和手的消毒,表面消毒,海绵、机织和无纺织物的浸渍。
本发明的组合物适合洗涤任何物体。本发明的组合物尤其适合在临床情况下和在手术之前对手进行洗涤,但也可用于洗涤无生命的物体,如外科器具。
Claims (33)
1.可杀灭假单胞菌的消毒清洁组合物,它包含:
杀菌剂,所述杀菌剂选自氯己定及其盐、以及氯苯酚衍生物,所述氯己定或其盐在组合物中的含量为1-4.5%w/v,所述氯苯酚衍生物在组合物中的含量为0.49-3%w/v;
烷基多糖表面活性剂,它在组合物中的含量大于0,但是不超过6%w/v;
至少一种C1-C6烷基醇,它在组合物中的含量为3-10%w/v;
至少一种芳基醇,所述芳基醇选自苄醇、苯乙醇、苯氧基乙醇、苯氧基丙醇或它们的氯代衍生物,它在组合物中的含量大于0,但是不超过3%w/v;
惰性载体,所述惰性载体是水。
2.可杀灭假单胞菌的消毒清洁组合物,它包含:
杀菌剂,所述杀菌剂选自氯己定及其盐、以及氯苯酚衍生物,所述氯己定或其盐在组合物中的含量为1-4.5%w/v,所述氯苯酚衍生物在组合物中的含量为0.49-3%w/v;
烷基多糖表面活性剂,它在组合物中的含量大于0,但是不超过6%w/v;
至少一种C1-C6烷基醇,它在组合物中的含量为55-75%w/v;
至少一种芳基醇,所述芳基醇选自苄醇、苯乙醇、苯氧基乙醇、苯氧基丙醇或它们的氯代衍生物,它在组合物中的含量大于0,但是不超过3%w/v;
惰性载体,所述惰性载体是C1-C6烷基醇。
4.如权利要求1或2所述的组合物,其中,表面活性剂烷基多糖含一种或多种糖单元,所述糖单元选自麦芽糖、阿拉伯糖、木糖、甘露糖、半乳糖、葡萄糖、艾杜糖、塔罗糖、阿洛糖、阿卓糖、蔗糖、果糖、山梨糖、左旋糖、乳糖、阿罗糖、塔格糖、阿洛庚酮糖、景天庚酮糖、葡庚酮糖、甘露庚酮糖、古洛庚酮糖、艾杜庚酮糖、半乳庚酮糖和塔罗庚酮糖。
5.如权利要求1或2所述的组合物,其中,所述氯己定的盐选自葡糖酸盐、羟乙磺酸盐、甲酸盐、乙酸盐、谷氨酸盐、琥珀酰胺酸盐、单二甘醇酸盐、二甲磺酸盐、乳酸盐、二异丁酸盐或葡庚糖酸盐。
6.如权利要求1或2所述的组合物,其中,奥替尼啶盐是奥替尼啶二盐酸盐。
7.如权利要求1或2所述的组合物,其中,所述杀菌剂是二葡糖酸氯己定。
8.如权利要求1或2所述的组合物,其中,所述氯苯酚衍生物选自二邻苄基-对氯苯酚、对氯-间二甲苯酚、邻苄基-对氯苯酚、邻苯基苯酚和2,4,4-三氯-2-羟基-二苯基醚。
9.如权利要求1或2所述的组合物,其中所述杀菌剂是2,4,4-三氯-2-羟基-二苯基醚。
10.如权利要求9所述的组合物,其中,2,4,4-三氯-2-羟基-二苯基醚不超过3%w/v。
11.如权利要求1或2所述的组合物,其中,杀菌剂在环境温度下的水溶性至少为0.001%w/v。
12.如权利要求1或2所述的组合物,其中,所述C1-C6烷基醇是乙醇、异丙醇或正丙醇。
13.如权利要求1或2所述的组合物,其中,所述C1-C6烷基醇是乙醇。
14.如权利要求12所述的组合物,其中,所述C1-C6烷基醇是异丙醇或正丙醇或它们的组合。
15.如权利要求1或2所述的组合物,其中,所述芳基醇选自苯氧基乙醇和苯氧基丙醇。
16.如权利要求1或2所述的组合物,它还包括一种或多种选自以下物质的成分:
(a)增溶剂,
(b)起泡剂,
(c)一种或多种粘度调节剂,
(d)防腐剂,
(e)其它常用添加剂,所述常用添加剂选自着色剂、芳香剂、抗氧化剂、润肤剂、稳定剂和增稠剂,
(f)另外的表面活性剂。
17.如权利要求16所述的组合物,其中,所述增溶剂是丙二醇、水溶助长剂或它们的混合物。
18.如权利要求17所述的组合物,其中,所述水溶助长剂选自尿素、枯烯磺酸盐、甲苯磺酸盐、二甲苯磺酸盐及乙醇胺柠檬酸盐。
19.如权利要求16所述的组合物,其中,所述起泡剂是烷基胺氧化物、烷基单或二乙醇酰胺。
20.如权利要求19所述的组合物,其中,所述起泡剂选自月桂基缩合物、椰子基二乙醇酰胺缩合物、单乙醇酰胺缩合物、月桂基二甲胺氧化物和鲸蜡基二甲胺氧化物。
21.如权利要求16所述的组合物,其中,所述粘度调节剂选自纤维素衍生物、瓜尔树脂和聚羧乙烯树脂。
22.如权利要求16所述的组合物,其中,所述防腐剂选自咪唑烷基衍生物、脲衍生物、羟苯甲酸甲酯或羟苯甲酸丙酯。
23.如权利要求16所述的组合物,其中,所述增稠剂是羧甲基纤维素。
24.如权利要求16所述的组合物,其中,所述另外的表面活性剂选自两性表面活性剂、阴离子型表面活性剂和非离子型表面活性剂。
25.如权利要求24所述的组合物,其中,所述另外的表面活性剂包括季铵化合物或高起泡性阴离子型表面活性剂。
26.如权利要求25所述的组合物,其中,高起泡性阴离子型表面活性剂选自月桂基乙氧基磺酸盐、肌氨酸盐和二月桂基醚硫酸钠。
27.如权利要求1或2所述的组合物,其中,所述pH是8或更小。
28.如权利要求27所述的组合物,其中,所述pH在5至7之间。
29.如权利要求28所述的组合物,其中,所述pH是5.5。
30.如权利要求1或2所述的组合物,其中,用有机酸对pH进行调节。
31.如权利要求30所述的组合物,其中,所述有机酸选自乳酸、乙酸、柠檬酸和葡糖酸。
32.如权利要求31所述的组合物,其中,所述有机酸是葡糖酸。
33.对被包括假单胞菌属微生物在内的细菌污染的表面去污的方法,该方法包括将该表面与权利要求1或2所述的消毒清洁组合物接触。
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-
1997
- 1997-05-20 AU AUPO6909A patent/AUPO690997A0/en not_active Abandoned
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1998
- 1998-05-07 NZ NZ501185A patent/NZ501185A/en not_active IP Right Cessation
- 1998-05-07 DK DK98918984T patent/DK0983335T3/da active
- 1998-05-07 TR TR1999/02850T patent/TR199902850T2/xx unknown
- 1998-05-07 IL IL13295698A patent/IL132956A0/xx not_active IP Right Cessation
- 1998-05-07 WO PCT/AU1998/000329 patent/WO1998053036A1/en active IP Right Grant
- 1998-05-07 ID IDW991402A patent/ID24921A/id unknown
- 1998-05-07 AT AT98918984T patent/ATE311433T1/de not_active IP Right Cessation
- 1998-05-07 ES ES98918984T patent/ES2253814T3/es not_active Expired - Lifetime
- 1998-05-07 CN CNB988052210A patent/CN1212384C/zh not_active Expired - Lifetime
- 1998-05-07 JP JP54969398A patent/JP4172659B2/ja not_active Expired - Lifetime
- 1998-05-07 EP EP98918984A patent/EP0983335B1/en not_active Expired - Lifetime
- 1998-05-07 DE DE69832601T patent/DE69832601T2/de not_active Expired - Fee Related
- 1998-05-07 BR BRPI9809881-0A patent/BR9809881B1/pt not_active IP Right Cessation
- 1998-05-07 CA CA002290487A patent/CA2290487A1/en not_active Abandoned
- 1998-05-07 KR KR10-1999-7010746A patent/KR100531502B1/ko not_active IP Right Cessation
- 1998-05-07 US US09/424,158 patent/US6531434B1/en not_active Expired - Lifetime
- 1998-05-14 MY MYPI98002153A patent/MY117402A/en unknown
- 1998-05-14 ZA ZA984066A patent/ZA984066B/xx unknown
- 1998-05-18 IN IN1315DE1998 patent/IN191603B/en unknown
- 1998-05-20 TW TW087108027A patent/TWI224012B/zh not_active IP Right Cessation
-
2000
- 2000-08-28 HK HK00105373A patent/HK1026712A1/xx not_active IP Right Cessation
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2003
- 2003-02-25 US US10/372,663 patent/US7163914B2/en not_active Expired - Lifetime
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MY117402A (en) | 2004-06-30 |
US7163914B2 (en) | 2007-01-16 |
ID24921A (id) | 2000-08-31 |
NZ501185A (en) | 2001-04-27 |
ATE311433T1 (de) | 2005-12-15 |
AUPO690997A0 (en) | 1997-06-12 |
JP2001525877A (ja) | 2001-12-11 |
EP0983335B1 (en) | 2005-11-30 |
WO1998053036A1 (en) | 1998-11-26 |
DE69832601T2 (de) | 2006-08-10 |
US20050215461A1 (en) | 2005-09-29 |
HK1026712A1 (en) | 2000-12-22 |
EP0983335A4 (en) | 2001-02-28 |
CA2290487A1 (en) | 1998-11-26 |
IN191603B (zh) | 2003-12-06 |
JP4172659B2 (ja) | 2008-10-29 |
TWI224012B (en) | 2004-11-21 |
CN1256709A (zh) | 2000-06-14 |
DE69832601D1 (de) | 2006-01-05 |
BR9809881B1 (pt) | 2009-05-05 |
IL132956A0 (en) | 2001-03-19 |
KR20010012784A (ko) | 2001-02-26 |
TR199902850T2 (xx) | 2000-06-21 |
DK0983335T3 (da) | 2006-03-27 |
KR100531502B1 (ko) | 2005-11-28 |
US6531434B1 (en) | 2003-03-11 |
ES2253814T3 (es) | 2006-06-01 |
ZA984066B (en) | 1998-11-25 |
BR9809881A (pt) | 2000-07-04 |
EP0983335A1 (en) | 2000-03-08 |
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