CN1172654C - 驱虫的防晒制品 - Google Patents
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Abstract
本发明公开的是防晒制品。它的配方中还包括防水剂和驱虫剂。一种形式是在水乳剂中含有DEET、防晒剂、阴离子表面活性剂、烷基化的聚乙烯基吡咯烷酮和新戊酸辛基十二烷基酯。并且公开了制备和使用该防晒制品的方法。
Description
本发明涉及提供高SPF的防晒性能和优良的驱虫性能的组合物。它能在皮肤经常浸入水中的环境下使用。
太阳的紫外线会晒黑人们的皮肤。然而,长时间暴露在紫外线下会有不利的影响,诸如皮肤干燥、出现晒斑,极端情况下还会导致皮肤癌。因而,本技术开发了防晒制剂,包括可以涂敷到皮肤上帮助皮肤遮挡太阳紫外线或者减小其有害影响的洗液及其它材料。
人们还常常希望在户外不受蚊子和其它飞虫的侵扰。这可以通过往皮肤上单独涂敷一种驱虫剂来实现。然而,这需要两次单独的涂敷和两种单独的产品,而且防晒制品和驱虫剂中的成分存在着不完全相容的危险。
因此,试图提供同时具有防晒性能和驱虫性能的单一洗液。例如,见PCT专利申请WO 95/19161(1995)和美国专利U.S.5,518,712;5,346,922;3,186,912和1,471,344.这些公开的专利和其它所有在此引用的文献作为参考,就如同在此完整地阐述一样。
使情况变得更复杂的因素是人们希望即使是使用者在水中浸泡过,如在海滨游泳之后,该防护剂仍然有效。因此,防水的化合物被加入到这类产品中。例如,见PCT专利申请WO 95/19161(1995)和美国专利U.S.5,518,712和4,810,489。
然而,在寻求高SPF的保护作用,例如大于或等于SPF 15,以及良好的抗水性能和有效的驱虫作用时,各有效成分之间会发生不利的冲突。对于DEET(一种优选的驱虫有效成分)尤其如此。
此外,人们还希望防晒制剂涂敷到皮肤上时能够形成一层光滑、均匀、不油腻的防晒剂膜并具有其它良好的化妆品特性。这为防晒剂的开发者提出了额外的问题。
因此,需要开发一种改进的驱虫的防晒剂。
一方面,本发明提供了一种驱虫的防晒剂组合物。其中包含重量百分数为10%到40%的防晒剂,所说的防晒剂至少在290-400nm的紫外辐射区的某些区域有吸收能力。还包括重量百分数为2%到50%的驱虫剂(优选的是低于25%,甚至更优选的是低于10%),重量百分数为1%到20%的新戊酸酯(优选新戊酸的C30或更低级烷基酯,如新戊酸辛基十二烷基酯),重量百分数为20%到60%的水,以及重量百分数为0.1%到15%的乳化剂(特别优选的是阴离子乳化剂)。还可以包含防水剂,如重量百分数为0.01%到5%的乙烯基吡咯烷酮的聚合物。
新戊酸辛基十二烷基酯(C25H50O2)被Bernel化学公司作为一种润肤剂或皮肤柔润剂ELEFAC I-205在市场上销售。也可添加其它已知的润肤剂,例如液态酯、硅酮油、矿物油、尿囊素、羊毛脂、矿脂、植物油如加州希蒙得木油(jojoba oil)和蓖麻油、丙二醇,以及脂肪醇如十六烷醇和十八烷醇。
所说的驱虫剂优选的是选自由下列物质组成的组中:N,N-二乙基甲苯甲酰胺(“DEET”),N,N-二乙基苯甲酰胺,对烷-3,8-二醇,1S,3S,4S,6R-蒈烯-3,4二醇(Sumitomo-美国专利U.S.5,130,136),2-(2-羟乙基)-1-哌啶甲酸的1-甲基丙酯,1-(3-环己烯-1-基-羰基)-2-甲基哌啶,1-(3-环己烯-1-基-羰基)哌啶,N,N-二乙基扁桃酰胺(N,N-diethylmandelamide),异蒲勒醇水合物,3-[N-正丁基-N-乙酰基]氨基丙酸乙酯,己二酸二异丙基酯(diisopropyladipate),α-联二蓝棕(biasabal),薄荷油,苄醇,N,N-二乙基苯乙酰胺,维生素E,香茅油,丁子香油,椰子油,雪松油,香叶醇,柠檬草油,百里香油,迷迭香油,薄荷油,香叶天竺葵油,丁子香酚,3-乙酰基-2-(2,6-二甲基-5-庚烯基)噁唑烷,(2-羟甲基环己基)乙酸内酯和桉叶油素。如果使用DEET,优选的是DEET在7.5%到30%范围内。然而,在特定的环境下,诸如昆虫滋生的沼泽,更高含量的DEET可能是合适的。
所说的防晒剂可以是任何在290nm到400nm的某些区域有吸光性能的适于人的皮肤涂敷试剂。优选的是选自由下列物质组成的组中:甲氧基肉桂酸2-乙基己基酯,水杨酸2-乙基己基酯,2-氰基-3,3-二苯基丙烯酸2-乙基己基酯,氧苯酮(oxybenzone),对二甲氨基苯甲酸2-乙基己基酯(padimate O)和二氧化钛。然而,还可以包括这些组分的混合物和/或其它的防晒剂,所说的其它防晒剂如氨基苯甲酸;桂醚酯(cinoxate);对-甲氧基肉桂酸二乙醇胺(diethanolamine p-methoxycinnamate);二棓酰的三油酸酯(digalloyl trioleate);4-甲氧基-2,2’-二羟二苯甲酮(dioxybenzone);4-[二(羟丙基)]氨基苯甲酸乙酯;对氨基苯甲酸甘油酯;水杨酸三甲环已酯(homosalate);2-羟基-1,4-萘醌(lawsone);邻氨基苯甲酸酯;2-苯基苯并咪唑-5-磺酸;红矿脂;羟基甲氧基二苯甲酮磺酸;氧化锌和水杨酸三乙醇胺。
所说的防水剂优选的是乙烯基吡咯烷酮类的聚合物,在这类聚合物中,优选的是乙烯基吡咯烷酮与长链烯烃形成的共聚物(“烷基化的乙烯基吡咯烷酮(alkylated PVP)”)。例如见美国专利U-S.4,810,489。最优选的防水剂是Ganex V-220,可从GAF公司得到。Ganex V-220是1-二十碳烯与1-乙烯基-2-吡咯烷酮的共聚物。其它合适的防水剂有聚异丁烯(PrisorineSQS3758,Unichema);tricontanvl PVP(Ganex WP-660-ISP);丙烯酸酯/辛基丙烯酰胺共聚物(Dermacryl-79;Versatyl-42;National Starch);二甲聚硅氧烷350 cSt(Dow);PVP/十六碳烯共聚物(Ganex V-216-ISP);Lexorez100(Inolex);丙烯酸酯/丙烯酸C10-30烷基酯的交联聚合物和PemulenTR1/TR2(Goodrich)。
增稠剂可以帮助达到更高SPF的保护功能,虽然增稠剂对于SPF的贡献的确切机理知道得并不十分清楚,但很显然它是通过对使用防晒组合物之后在皮肤上留下保护膜有贡献来实现的。优选的增稠剂是汉生胶(xanthan gum)、瓜尔胶、藻朊酸胶(alginate gums)、镁铝的硅酸盐、硬脂酸和十六烷醇。其它合适的增稠剂是硅酸盐和粘土类(例如膨润土,合成锂皂石),聚合的增稠剂(如BF Goodrich的丙烯酸聚合物(carbopolpolymers)),聚乙二醇增稠剂,纤维素增稠剂(如羟乙基纤维素),脂肪醇和聚羧乙烯制剂(carbomers)(如CTFA)。
所说的乳化剂优选阴离子表面活性剂如Givaudan-Roure公司的Amphisol(二乙醇胺-十六烷基磷酸盐)。然而,许多其它阴离子表面活性剂也可以用于该目的,如磷酸酯、磷的有机衍生物、醇的硫酸酯和乙氧化醇、链烷醇酰胺、磺化丁二酸酯、烷芳基磺酸盐以及其它基于蛋白质、碳氟化合物和硅酮的表面活性剂。
如果需要的话,还可加入其它常规的防晒剂成分。这些物质包括硅酮油(例如Dow Silicone 200-二甲聚硅氧烷-一种润滑剂)、甘油(一种膜增强剂)、Germaben II(一种防腐剂)和香料。2-氰基-3,3-二苯基丙烯酸2-乙基己基酯也可作为附加的防晒剂加入。这种材料是BASF公司的商品,名为Octocrylene。
一方面,本发明提供了一种方法,它包括在人体的外露部分涂敷这种组合物,使其既具有防晒功能又具有驱虫功能。另一方面,本发明提供了制造这种组合物的方法。
本发明的组合物即使在浸入水中之后仍具有高的SPF保护作用。它们还具有优越的驱虫作用。特别设计上述组合物,使其在“标准测试”(在下文描述)下的SPF(“防晒因子”)至少为SPF 15。这种“标准测试”是在没有防水要求下进行的试验。然而,如下文所述,类似的测试也可在浸没条件下进行。
“SPF 15”通俗的理解就是,例如一个人在没有防晒剂的条件下在太阳下10分钟后晒黑(burn)了,则按要求涂敷该产品后将要花15倍的时间才能晒成同样程度。然而,为了适应本专利的要求,按照“标准测试”更精确地确定了SPF 15(以及SPF)。这种标准测试通常是根据食品和药物管理局(Food and Drug Administration)于1978年8月25日公布的“OTC防晒药物制品提案”(“Proposed monogroph for OTC SunscreenDrug Products”),Federal Register Volume 43,Number 166,38206-38269。
测试用的光源是由Solar Light公司生产的Solar UltravioletSimulator,Model 10S,它由一个150瓦的氙弧光灯以及全部所需光学元件和一个常规电源组成。测试小组包括20个男女受试者,他们是根据上文提到的FDA的提案的标准考虑/排除。他们通过体检来确认被测试的背部区域的晒斑、晒黑、伤痕、有效的皮肤损伤和/或不均匀的皮肤颜色的存在。痣脂瘤(nevl)、缺陷或痣的存在只要不干扰研究结果就可以接受。背上多余的毛被刮掉。
对照组合物是8%的水杨酸三甲环己酯(homosalate,HMS)。每个测试位点区域用于确定受试者在涂敷了所说的防晒产品或8%的HMS对照物后的最小红斑量(minimal erythema dose)(MED),或用于确定受试者在皮肤不加保护的条件下的MED。MED是在16小时的后照射(post-exposure)中出现最小的可觉察的红斑的照射时间。测试部位是背部的腰带线与肩胛之间的区域,横向位置则在中线上。所说的测试位点区域优选的是方形区域。
用于涂敷产品或标准对照物的每个测试区域的面积是50平方厘米。在受试者处于直立位置(也就是进行照射的位置)时,描出这些测试位点区域的轮廓。用于测试物和8%的HMS的各个测试区域都被分成1平方厘米的小测试区。
为保证标准化的报告并确定产品的SPF值,产品的涂敷用量用形成标准膜的单位面积上的重量基准表示。被测的防晒产品的涂敷用量是2mg/cm2,8%的对照物HMS也是如此。
对于乳脂,高粘度凝胶和奶油状的物质,所说的产品要轻微加热以便能够按体积定量施用。在这样的加热过程中,必须小心以保证不改变产品的实质特性。糊剂和软膏称重后涂敷在测试部位。
在涂敷了产品之后以及将测试部位暴露在紫外线辐射之前,有15分钟的等待时间。然后是用日光模拟器对每个受试者的测试小区进行一系列的紫外光照射(多个时间单元)。
对未处理的未加保护的皮肤进行一个系列的照射从而确定MED。受试者未保护的皮肤的MED是在测试的当天确定的。被保护(施用8%的HMS对照和/或被测试的防晒产品)的测试区也用紫外光辐射。
选择的时间间隔呈几何级数,用(1.25)n来表示,其中,各个照射时间间隔都比前一个大25%。第三个测试小区的值是乘上MED的预期的SPF值。因此,所报道SPF值就是被保护皮肤的MED值除以未保护皮肤的MED值。
类似的测试可以用于评价防水SPF。为此,施用了防晒剂和对照物的受试者在紫外光照射之前在一个涡流的水中浸泡80分钟。这80分钟被分为四个20分钟,每两次浸泡之间有20分钟的休息时间。在紫外光照射之前,受试者的背部要在空气中干燥。
因此本发明的目的包括提供上述类型的组合物,它具有:
(a)既有高SPF的保护作用又有良好的驱虫特性;
(b)良好的防水SPF特性;
(c)满意的化妆品特性,特别是与柔润皮肤有关的特性;以及
(d)无油脂感。
本发明的这些目的以及其它目的(例如,制造和使用这些组合物的方法)在下面的描述中将是显而易见的。以下的描述仅仅是优选的实施方案。所以应当注意权利要求书以便理解本发明的全部范围。
以下是本发明的实施例组合物。下面列出的数字是重量百分数。
原料 | A | B | C | D | E |
硬脂酸(Emersol 132) | 5.00 | 4.00 | 5.00 | 4.00 | 5.00 |
十六烷醇 | 2.00 | 1.60 | 2.00 | 1.60 | 2.00 |
Amphisol(DEA-十六磷酸酯) | 2.00 | 2.00 | 2.00 | 2.00 | 2.00 |
Dow Silicone 200(100cps)(聚二甲基硅氧烷) | 0.50 | 0.50 | 0.50 | 0.50 | 0.50 |
甲氧基肉桂酸辛基酯 | 7.50 | 7.50 | 7.50 | 7.50 | 7.50 |
新戊酸辛基十二烷基酯(Elefac I-205) | 10.00 | 10.00 | 10.00 | 10.00 | 10.00 |
水杨酸辛基酯 | 5.00 | 5.00 | 5.00 | 5.00 | 5.00 |
二苯甲酮-3(Benzophenone-3) | 5.00 | 5.00 | 5.00 | 5.00 | 5.00 |
DEET | 7.50 | 20.00 | 7.50 | 25.00 | 7.50 |
去离子水 | 47.20 | 40.10 | 49.20 | 34.60 | 40.20 |
镁铝硅酸盐(Veegum) | 0.75 | 0.75 | 0.75 | 0.75 | 0.75 |
汉生胶(Kelco的Keltrol) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Germaben IIE(防腐剂) | 1.00 | 1.00 | 1.00 | 1.00 | 1.00 |
Ganex V-200 | 2.00 | 2.00 | 2.00 | 2.50 | 2.00 |
甘油 | 4.00 | 4.00 | |||
香料 | 0.30 | 0.30 | 0.30 | 0.30 | 0.30 |
超细TiO2(Cardre) | 2.00 | 2.00 | |||
氰双苯丙烯酸辛酯 | 2.00 | ||||
100.00 | 100.00 | 100.00 | 100.00 | 100.00 |
如下所述,在上面列出的含7.5%DEET的组合物与一种含10%DEET且SPF为15的有竞争力的防晒/驱虫商品“Sunsect”的对比实验中,配方A和C尽管使用了低的DEET含量,但仍较所说的Sunsect 10%组合物有更好的防叮咬性能。在另一个对比实验中,配方B与含20%DEET的同时含有驱虫和防晒组分的Sunsect进行了比较。结果仍然是本发明的产品比对比产品有更好的防虫性能。
防虫(insect protection)测试是用一种“笼中的手臂”的方式进行的。在这些测试中,受试者首先用香皂清洗胳膊,然后用水冲洗并晾干。接着用类似量的产品处理他们的前臂,带上白色的棉手套,然后将他们的前臂暴露在笼子里的昆虫中。笼子中的昆虫类型和数量描述如下。这些实验的结果详述如下。
以小时计的调整*保护时间
试样 | 蚊子密度 | 重复次数 | 第一次叮咬 |
A 7.5%DEET | 200 | 6 | 3.6 |
C 7.5%DEET | 200 | 6 | 2.6 |
Sunsect 10%DEET | 200 | 6 | 2.4 |
*大约三天的测试结果
以小时计的平均保护时间
试样 | 蚊子密度 | 重复次数 | 第一次叮咬 |
B 20%DEET | 1000 | 6 | 5.3 |
Sunsect 20%DEET | 1000 | 6 | 4.2 |
以小时计的平均保护时间
试样 | 马厩蝇密度 | 重复次数 | 第一次叮咬 |
B 20%DEET | 3000 | 6 | 0.9 |
Sunsect 20%DEET | 3000 | 6 | 0.7 |
本发明的组合物具有至少为15的静态(static)(在无水的条件下)的SPF值(使用与标准测试基本相同的测试方法),在浸水之后也可保持良好的SPF保护。配方A具有16.3的静态的SPF值以及15.8的防水SPF值。配方B具有16.2的静态的SPF值以及14.7的防水SPF值。配方C具有26.3的静态的SPF值以及24.6的防水SPF值。配方D具有16.5的静态的SPF值以及15.8的防水SPF值。配方E具有34.5的静态的SPF值以及31.8的防水SPF值。
为了制造优选的组合物,优选的是将除水、甘油、Veegum、Keltrol、香料和Germaben之外的组分在第一釜中混合,然后加热到180°F并保持15分钟直至得到清亮的黄色液体。
在第二釜中将甘油和水混合并加热到160°F。然后单独制备Veegum和Keltrol的干的混合物。在高剪切混合下将它慢慢地加入第二个甘油釜中。搅拌混合物直至水合完成,混合物被增稠了且没有结块。这个过程在160°F下典型地需要15分钟。
然后把第二个甘油釜的温度升至175°F。把第一个釜中的内容物与其混合并把该混合物搅拌15分钟。然后将混合物骤冷至110°F并加入Germaben和香料。把该混合物搅拌30分钟后冷却至室温。
优选的组合物可以挤压、流注或涂敷在人的皮肤上,然后涂抹并在皮肤上铺展开。这一过程优选在日光照射前的几分钟进行。
应当说明的是以上的描述仅仅是本发明的优选的实施方案。在权利要求的范围之内许多其它实施方案是可能的。所以应当注意权利要求书以便判断本发明的全部范围。
本发明提供的防晒制品即使是使用较低含量的驱虫活性成分也能得到比对照的竞争产品更优越的驱虫性能。它特别适合于在户外游泳或日光浴时保护人们的皮肤。
Claims (15)
1.一种驱虫防晒组合物,其特征在于包括:
a.含量在10wt%到40wt%之间的至少在290到400nm的紫外辐射波
段的某些区域有吸光性能的有机防晒剂;
b.含量在2wt%到50wt%之间的驱虫剂;
c.含量在1wt%到20wt%之间的新戊酸酯;
d.防水剂;
e.含量在20wt%到60wt%之间的水;以及
f.含量在0.1wt%到15wt%的乳化剂;
其中,所说的组合物在“标准测试”中的SPF值至少为SPF 15。
2.根据权利要求1的驱虫防晒组合物,其中,所说的乳化剂是一种阴离子乳化剂。
3.根据权利要求2的驱虫防晒组合物,其中,所说的新戊酸酯是新戊酸烷基酯。
4.根据权利要求2的驱虫防晒组合物,其中,所说的新戊酸酯是新戊酸辛基十二烷基酯。
5.根据权利要求2的驱虫防晒组合物,其中,所说的防水剂是乙烯基吡咯烷酮的聚合物。
6.根据权利要求5的驱虫防晒组合物,其中,所说的防水剂的在所说的组合物中的重量分数在0.01%到5%之间。
7.根据权利要求1的驱虫防晒组合物,其中,所说的防水剂是聚乙烯基吡咯烷酮与烯烃的共聚物。
8.根据权利要求2的驱虫防晒组合物,其中,所说的驱虫剂选自由下列物质组成的组中:N,N-二乙基甲苯甲酰胺,N,N-二乙基苯甲酰胺,对烷-3,8-二醇,2-(2-羟乙基)-1-哌啶甲酸的1-甲基丙酯,1-(3-环己烯-1-基羰基)-2-甲基哌啶,香茅油,丁子香油,椰子油,雪松油,香叶醇,柠檬草油,百里香油,迷迭香油,薄荷油,香叶天竺葵油和丁子香酚。
9.根据权利要求8的驱虫防晒组合物,其中,所说的驱虫剂是N,N-二乙基甲苯甲酰胺。
10.根据权利要求2的驱虫防晒组合物,其中,所说的防晒剂选自由下列物质组成的组中:甲氧基肉桂酸2-乙基己基酯,水杨酸2-乙基己基酯,2-氰基-3,3-二苯基丙烯酸2-乙基己基酯,氧苯酮,对二甲氨基苯甲酸2-乙基己基酯和二氧化钛。
11.根据权利要求10的驱虫防晒组合物,其中,所说的防晒剂是甲氧基肉桂酸2-乙基已酯、水杨酸2-乙基己酯和氧苯酮的混合物。
12.根据权利要求2的驱虫防晒组合物,其特征在于还包含一种增稠剂,所说的增稠剂选自由下列物质组成的组中:汉生胶、瓜尔胶、藻朊酸胶、镁铝的硅酸盐、硬脂酸和十六烷醇。
13.根据权利要求12的驱虫防晒组合物,其特征在于还包含硅酮油和香料。
14.一种在人体外露的部分涂敷所说的组合物以使所说的组合物具有防晒和驱虫作用的方法,它包括在人体皮肤涂敷根据权利要求1的组合物的步骤。
15.一种制造既防晒又驱虫的组合物的方法,包括将根据权利要求1的防晒剂、驱虫剂、新戊酸酯、防水剂和乳化剂与水混合以得到根据权利要求1的组合物。
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US08/670,944 | 1996-06-26 | ||
US08/670,944 US5716602A (en) | 1996-06-26 | 1996-06-26 | Insect repellent sunscreen |
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JPH08183720A (ja) * | 1994-12-28 | 1996-07-16 | Kose Corp | 皮膚外用剤 |
US5486352A (en) * | 1995-01-03 | 1996-01-23 | Elizabeth Arden Company | Sunscreen compositions |
US5575988A (en) * | 1995-04-07 | 1996-11-19 | Littlepoint Corp. | Combination sunscreen and insect repellent |
-
1996
- 1996-06-26 US US08/670,944 patent/US5716602A/en not_active Expired - Lifetime
-
1997
- 1997-06-25 TW TW086108872A patent/TW534818B/zh not_active IP Right Cessation
- 1997-06-26 PT PT97930237T patent/PT910335E/pt unknown
- 1997-06-26 ZA ZA9705682A patent/ZA975682B/xx unknown
- 1997-06-26 EP EP97930237A patent/EP0910335B1/en not_active Expired - Lifetime
- 1997-06-26 ES ES97930237T patent/ES2185951T3/es not_active Expired - Lifetime
- 1997-06-26 NZ NZ333629A patent/NZ333629A/xx unknown
- 1997-06-26 PL PL97330917A patent/PL330917A1/xx unknown
- 1997-06-26 KR KR1019980710654A patent/KR100352356B1/ko not_active IP Right Cessation
- 1997-06-26 AT AT97930237T patent/ATE226061T1/de not_active IP Right Cessation
- 1997-06-26 CN CNB97196789XA patent/CN1172654C/zh not_active Expired - Fee Related
- 1997-06-26 AR ARP970102825A patent/AR007629A1/es active IP Right Grant
- 1997-06-26 BR BR9709965A patent/BR9709965A/pt not_active IP Right Cessation
- 1997-06-26 JP JP10503561A patent/JP2000514050A/ja active Pending
- 1997-06-26 CZ CZ19984301A patent/CZ290892B6/cs not_active IP Right Cessation
- 1997-06-26 CA CA002259292A patent/CA2259292C/en not_active Expired - Fee Related
- 1997-06-26 WO PCT/US1997/011221 patent/WO1997049380A1/en active IP Right Grant
- 1997-06-26 DE DE69716429T patent/DE69716429T2/de not_active Expired - Fee Related
- 1997-06-26 AU AU34120/97A patent/AU713810B2/en not_active Ceased
- 1997-06-26 RU RU99101480/14A patent/RU2170573C2/ru not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ES2185951T3 (es) | 2003-05-01 |
US5716602A (en) | 1998-02-10 |
AU713810B2 (en) | 1999-12-09 |
CA2259292A1 (en) | 1997-12-31 |
DE69716429D1 (de) | 2002-11-21 |
TW534818B (en) | 2003-06-01 |
RU2170573C2 (ru) | 2001-07-20 |
KR20000022234A (ko) | 2000-04-25 |
ATE226061T1 (de) | 2002-11-15 |
CA2259292C (en) | 2002-11-19 |
PL330917A1 (en) | 1999-06-07 |
JP2000514050A (ja) | 2000-10-24 |
WO1997049380A1 (en) | 1997-12-31 |
AR007629A1 (es) | 1999-11-10 |
CN1226156A (zh) | 1999-08-18 |
PT910335E (pt) | 2003-02-28 |
KR100352356B1 (ko) | 2002-12-28 |
DE69716429T2 (de) | 2003-02-20 |
CZ430198A3 (cs) | 1999-07-14 |
NZ333629A (en) | 1999-11-29 |
ZA975682B (en) | 1998-01-23 |
EP0910335B1 (en) | 2002-10-16 |
EP0910335A1 (en) | 1999-04-28 |
CZ290892B6 (cs) | 2002-11-13 |
BR9709965A (pt) | 1999-08-10 |
AU3412097A (en) | 1998-01-14 |
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