CN1078069C - 活性物质供给体系 - Google Patents
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Abstract
本发明涉及一类组合物,它包括一种合氮化合物,其中该氮原子经由一个酯键连接到一个活性物质基团上,该组合物具有其活性物质基团可有效地沉积在一个表面上,然后活性物质延迟释放到该表面上的功能。
Description
本发明涉及一类组合物,该组合物包括一种含氮化合物,这个氮原子经由一个酯键连接到一个活性物质基团上。所说的组合物具有其活性物质基团极好地沉积到一个表面上,和之后此活性物质延缓释放到该表面上的功能。
众所周知,使用活性物质例如醇和/或酸时,由于其本身固有的特性,它们的活性常常难于控制。虽然本发明不局限于织物软柔顺剂(softener)组合物,但是在使用织物柔顺剂组合物的实例中,在常规组合物中附加了香料、防汗剂化合物等以便在衣物洗涤过程中的漂洗之后得到所希望的结果。
近些年,人们对更符合环保要求的材料的需要提高了,而且可快速生物降解的季铵化合物已经作为传统上使用的二-长链氯化铵的取代物出现了。这类季铵化合物含有被诸如羧基的官能团隔断的长链烷(烯)基团。
所说的含有这些物质的材料和织物柔顺组合物已公开在诸如EPA 0040562和EPA 239910的大量出版物上。
在EPA 239910中,已经公开2.5-4.2的pH值范围向所说的可快速生物降解的铵化合物提供最佳的贮存稳定性。
上述体系的缺点是难以控制在相应柔顺剂组合物中诸如香料和防汗剂的活性物质的活性。活性物质对表面的亲和性不佳。一旦它们在一个表面上,由于其水溶性或高挥发性,它们就会被移走,并且有时可能失去全部活性。
EP 56152叙述了通过让液体在衣物上作用、从衣物上除去液体和干燥衣服的方法在含有织物柔顺剂季铵化合物和抗菌活性物质的水溶液中同时对被洗衣物进行柔顺和抗菌处理的工艺。被洗衣物在液体中旋转,液体中除含有至少一种标准织物柔顺季铵化合物外,还含有至少一种吡咯化合物作为抗菌活性物质。但在EP 56152中所述的这一体系中,为得到例如防不良气味的最理想的结果,该活性物质的活性是难以控制的。
上述难题可通过本发明制得的组合物加以解决,并且在一项优选实施方案中本发明的组合物是一种织物柔顺剂的组合物,其中基本原理是将一种诸如醇或酸的活性物质经由一个酯键连接到一个氮原子上。本身不是表面的一部分的活性物质用本发明的方法可有效地沉积到表面上。由于酯连接的微弱,结果很可能是活性物质的释放例如由于水解过程而发生。表面为织物时,本发明使活性物质令人惊奇地有效地沉积和保留在织物表面上,之后活性物质再缓慢释放。
或者它的一种胺的前体,
其中:
R1是Q′-T1或Q′-T2或T2或R6,
R2是Q″-T1或Q″-T3或T3或R6,
Q′和Q″的定义如Q,其中分别地R4为R4′或R4″以及R5为R5′或R5″,
R3和R6是相同或不同的C1-C4烷基或C1-C4羟烷基或H,
R4、R4′和R4″以及R5、R5′和R5″是任何(未)取代无环或任何(未)取代单或多(杂)环有机基团,
T1是一种活性物质基团,
T2和T3是(相同或不同的)C5-C30烷基或链烯基或芳香基,X-是一个可相容阴离子。
T′被定义为一个活性物质基团。“活性物质基团”意指例如水解时产生活性物质的化合物部分。
如果活性物质是一种醇,那末活性醇可能首先与一种二酸(或二酸酐)反应生成一种酸酯。根据本发明,这一产物随后经由这一游离酸官能团连接到化合物中心部分的游离醇官能团上。可另外,活性醇也可以直接连接到化合物中心部分的游离酸官能团上。
分子的中心部分可以是任何乙氧化的胺(例如三乙醇胺、甲基二乙醇胺以及诸如此类)或有可能是一个更为复杂的羟基官能团化的胺或季铵或一个(多)羧基官能团化的胺或季铵。
活性物质可以是任何需要沉积在织物上的酸或醇。根据不同的应用,可以用活性物质与化合物中心部分的单酯、含有酯肪酸的混合酯或多酯。
这一体系同样可用于将活性物质沉积在除织物以外的表面上,例如皮肤、头发或任何人们打算处理的表面上。
一种应用是在织物柔顺化时的香料供给。
这一技术允许香料成分非常有效的沉积,之后,由于将活性物质连接到分子中心部分的酯键水解而缓慢释放。
在织物柔顺剂基质中的其它可能应用是杀菌剂的供给(防止不良气味)、防汗剂的供给(防止穿着时的不良气味)以及衣物助熨烫剂的供给。
选择不同的活性物质,这一供给体系同样用于织物柔顺剂以外的领域:例如洗涤剂中香料的供给。在诸如除不良气味剂的化妆品中防汗剂的供给、在防头皮屑香波中杀霉菌素的供给、在衣物熨烫时由于湿和/或热导致的水解而释放挥发性顶部标记(top notes)而在助熨烫剂中的顶部标记的供给、在杀虫剂中杀害虫剂、杀昆虫/驱虫剂的供给或者在硬表面清洗剂中防腐蚀剂的供给。
发明详述
R1是Q′-T1或Q′-T2或T2或R6,
R2是Q″-T1或Q″-T3或T3或R6,
Q′和Q″的定义为Q,其中分别地R4为R4′或R4″以及R5为R5′或R5″,
R3和R6是相同或不同的C1-C4烷基或C1-C4羟烷基或H,
R4、R4′和R4″以及R5、R5′和R5″是任何(未)取代无环或任何(未)取代单或多(杂)环有机基团,
T1是一种活性物质基团,
T2和T3是(相同或不同的)C5-C30烷基或链烯基或芳香基,X-是一个可相容阴离子。
阴离子仅仅作为带正电的季铵化合物或质子化胺的反离子而存在。本发明的范围并不被认为局限于某一特定阴离子,尽管在某些组合物中一些特定阴离子的使用可能更为优选。
“其胺的前体”意指与上述季铵化合物相应的伯胺或叔胺。
本发明还包括一种组合物,它包括含有一个氮的一种化合物,其中该氮原子以一种咪唑鎓基、咪唑啉或吡啶鎓基团或其它环铵化合物和/或它们的前体存在,或以一种氧化胺基团存在。
R1是Q′-T1或Q′-T2或T2或R6,
Q′和Q″的定义为Q,其中分别地R4是R4′或R4″以及R5是R5′或R5″,
R3和R6是相同或不同的C1-C4烷基或C1-C4羟烷基或H,
R4、R4′和R4″以及R5、R5′和R5″是任何(未)取代无环或任何(未)取代单或多(杂)环有机基团,
T1是一种活性物质基团,
T2和T3是(相同或不同的)C5-C30烷基或链烯基或芳香基,X-是一个可相容阴离子。
本发明的另一方面还包括一种组合物,它包括含有几个氮的一种化合物,其中化合物有下列结构式:
或其胺的前体
Q″的定义如Q,其中R4是R4″,R5是R5″。
R3和R6是相同或不同的C1-C4烷基或C1-C4羟烷基或H,
R4、R4′、R4″、R5和R5″是任何(未)取代无环或任何(未)取代单或多(杂)环有机基团,
T1是一种活性物质基团,
T2和T3是(相同或不同的)C5-C30烷基或链烯基或芳香基,X-是一可相容阴离子,p和q是整数。
或其胺的前体:
其中:
R1是Q′-T1或Q′-T2或T2或R6,
R2是Q″-r1或Q″-T3或T3或R6
Q′和Q″的定义为Q,其中分别地R4是R4′或R4″以及R5是R5′或R5″,
R3和R6是相同或不同的C1-C4烷基或C1-C4羟基烷基或H,
R4、R4′和R4″和R5、R5′和R5″是任一(未)取代无环或任何(未)取代单或多(杂)环有机基团,
T1是一多羟基和/或多羧基官能团活性物质基团,
T2和T3是(相同或不同的)C5-C30烷基或链烯基或芳香基,X-是一可相容阴离子。
根据本发明的活性物质可以选自天然或合成的含有酸或醇的一类活性物质。
进一步来讲,根据本发明的活性物质可以选自羟基或羧基官能团香料成分、杀细菌剂、杀真菌剂、防汗剂、淀粉或改性淀粉、杀害虫剂、杀昆虫剂、驱虫剂或防腐剂。
根据应用情况,本发明的组合物还可以这样使用,例如常规织物调理剂或织物柔顺剂基质组份以及添加剂也可以加入组合物中。
在另一应用中,常规洗涤剂基质组份和添加剂可以加入本组合物中。
同样,常规香料和/或除味剂基质组份、常规香波/头皮调理剂基质组份。杀虫剂基质组份或硬表面清洗剂基质组份也可以加入到本发明的组合物中。
根据所选择的活性物质和相应的基质组份的情况,组合物可以用作香料供给体系、杀细菌剂供给体系、杀真菌剂供给体系、防汗剂供给体系、杀昆虫剂或驱虫剂供给体系或衣物助熨烫剂供给体系。
为获得织物柔顺剂组合物而使用的成分在例如EP239,910已有所叙述。
实施例通过下列实施例举例说明了本发明。
实施例1根据本发明的一种化合物的合成,其中的活性物质是香叶酸。1摩尔香叶酸与1摩尔甲基二乙醇胺反应(160℃、16小时真空下)生成香叶酸与甲基二乙醇胺的酯。反应混合物进一步与1摩尔硬脂酸反应(160℃、24小时真空下)生成与甲基二乙醇胺的混合二酯。然后用甲基氯化物加15%异丙醇作为季铵化溶剂将二酯季铵化。得到的季铵化合物可以按照本发明引入一个组合物中。
实施例2根据本发明一种化合物的合成,其中活性物质是香茅醇。1摩尔N-甲基,N,N-二乙酸胺与0.5摩尔香茅醇反应(150℃、24小时、真空下)。得到的混合物再与1.5摩尔脂肪醇反应(150℃、24小时、真空下)。然后用甲基氯化物加10%异丙醇作为季铵化溶剂将二酯季铵化。得到的季铵化合物可以按照本发明引入一个组合物中。
实施例3根据本发明一种化合物的合成,其中活性物质是异戊酸。评价改进的活性。3.a)化学合成1摩尔甲基二乙醇胺与0.2摩尔异戊酸反应(160℃、16小时、真空下)生成异戊酸与甲基二乙醇胺的单酯。反应混合物进一步与1.8摩尔硬脂酸反应(160℃、24小时、真空下)生成混合二酯。然后用甲基氯化物加入15%异丙醇作为季铵化溶剂将二酯季铵化。因此1000g这种原材料中含有850g季铵化合物和与季铵化合物化学相连的27.3g异戊酸。3.b)分散剂制备下面1.a所述原材料的7%酸化分散剂的制备。1)927.3g脱矿物质水加热至65℃并维持在此温度下。2)2.7g10%盐酸溶液加入上述水中。3)70g下面1.a所述原材料加热至75℃并在连续搅拌下加入酸化水中。加入时间为1分钟。4)得到的分散剂在连续搅拌下冷却至环境温度。该分散剂有3.3±0.3的pH值。最终产物中含有0.19%与季铵化合物化学相连的异戊酸。3.c)产品应用2.1kg织物(60%纯棉、40%混纺聚酯/棉)在60℃下用180g常用Belgium Ariel洗涤剂在一个AEG ko-Lavamat579的洗衣机中洗涤(仅仅大致地洗涤)。衣物桶中含有12个原绒布(棉质)示踪物,每个重30g。3.c.1.参照处理用70g其中混以2.73%的异戊酸的标准季铵化合物(即按1.a所述合成的季铵化合物,未加入异戊酸,使用2摩尔硬脂酸)按照下面1.b所述的步骤制备参照分散剂。该参照分散剂因此含有0.19%的自由异戊酸。3.c.1.a(自由活性(free active),未加另外漂洗)110g该参照分散剂加入洗衣机最后一次漂洗液中,洗衣机停止漂洗循环后取出12个示踪物中的6个。3.c.1.b(自由活性,另加漂洗)先取出6个示踪物后,对剩余衣物再在相同洗衣机中进行一次漂洗循环。洗衣机停止漂洗循环后取出剩下的6个示踪物。3.c.2)试验处理3.c.2.a(EQDS,未加另外漂洗)110g 1.6所述分散剂加入洗衣机最后一次漂洗液中,在洗衣机停止漂洗循环后取出12个示踪物中的6个。3.c.2.b(EQDS,另加漂洗)先取出6个示踪物后,再在相同的洗衣机里对剩余衣服再进行一次漂洗。洗衣机停止漂洗循环后取出剩下的6个示踪物。3.d)织物分级3.d.1)示踪物贮存示踪物(湿的)从洗衣机中取出后被分级。然后在环境温度下将织物搭在绳上晾干,并在第二天(干燥一天)再次分级。然后将示踪物包在铝箔中并在环境温度下贮存在实验室的长凳上。评价者在贮存一星期和二星期后重新评价。3.d.2分级步骤示踪物成对地比较(自由、未加另外漂洗对EQDS、未加另外漂洗;自由、另加漂洗对EQDS、另加漂洗)。每对示踪物被4个蒙住眼睛的评价者评价。示踪物以不同的顺序提供给评价者。评价使用下列标准:0:没有区别1:我认为一个闻起来浓些2:我肯定一个闻起来浓些3:我肯定一个闻起来浓得多4:一种闻起来浓很多实验监督者当EQDS处理物味浓时划以分级正号,当参照处理物味浓时划以分级负号。将不同分级的平均值记录下来。3.d.3)结果3.d.3.a)未加另外漂洗EQDS对自由异戊酸,+表示EQDS气味较浓,0-4级。湿 -1.5干燥1天 0贮存1周 2.5贮存2周 3.03.d.3.b)另加漂洗EQDS对自由异戊酸,+表示EQDS气味较浓,0-4级。湿 0干燥1天 1.5贮存1周 2.5贮存2周 3.0上面提到的结果清楚地表明活性基团已经有效地沉积在织物上,并在随后的漂洗中停留在织物上,而且在织物贮存期间活性物质逐渐释放出来.
实施例4下列包含按照实施例1的化合物的织物柔顺剂组合物进一步说明了本发明。N,N-二(2-牛脂氧基-氧-乙基) 18%N,N甲基氯化铵牛脂醇25乙氧化物 2%多甘油单硬脂酸酯 5.0%HCl 0.08%CaCl2 0.3%香料 0.5%实施例1的化合物 0.3%染料、抗泡沫剂、水 余量
实施例5下列包含按照实施例1的化合物的洗涤剂组合物进一步说明了本发明。C11-12烷基苯磺酸(钠)盐 6.5%牛脂醇硫酸(钠)盐 1.0%牛脂醇乙氧化物(EO11) 0.8%氢化牛脂脂肪酸 1.0%二硬脂酰甲胺 3.0%十二烷基二甲胺N-氧化物 0.4%沸 20%聚环氧乙烷(MW=5MW) 0.05%硫酸钠 12.7%硅酸钠 2.0%过硼酸钠(4 aq.) 20.0%羧基甲基纤维素 0.4%聚丙烯盐酯(MW=4000-5000) 3.0%酶(蛋白酶、淀粉酶、纤维素酶) 0.3%光鲜剂 0.25%乙二胺四亚甲基膦酸 0.1%四乙酰乙二胺 1.5%硅氧烷/硅石泡沫压伏剂 0.2%蒙脱石粘土 10%香料 0.2%实施例1的化合物 0.5%
实施例6下列包含按照实施例1的化合物的头发调理剂组合物进一步说明了本发明。牛脂醇乙氧化物(TAE11) 2.0%二甲基苄基硬脂酰氯化铵 1.0%十六烷基单甘油酯 2.0%十六烷醇 2.5%甲基羟丙基纤维素 0.7%四级结构化羟乙基纤维素 0.5%盐酸 0.2%香料 0.2%实施例1的化合物 0.3%染料、杀菌剂、水 剩余部分
Claims (25)
1.一种含有含氮化合物的组合物,该氮原子经由一个酯键连接到一个活性物质基团上,该组合物的活性物质基团可有效地沉积在一个表面上,之后活性物质缓慢释放到该表面上,所述的化合物具有下列结构式:或其一个胺的前体
其中:
R1是Q′-T1或Q′-T2或T2或R6,
R2是Q″-T1或Q″-T3或T3或R6,
Q′和Q″的定义如Q,其中分别地R4是R4′或R4″以及R5为R5′或R5″,
R3和R6相同或不同,为C1-C4烷基或C1-C4羟烷基或H,
R4、R4′和R4″以及R5、R5′和R5″是任何取代或未取代的无环或任何取代或未取代的单或多环有机基团或单或多杂环有机基团,
T1是一种活性物质基团,会产生一种选自天然或合成的一类酸或醇的活性物质,
T2和T3相同或不同,是C5-C30烷基或链烯基或芳基,X-是一个可相容阴离子。
2.根据权利要求1的组合物,其中R4是(CH2)n或(CH2-CH2-O)nCH2-CH2-以及R5是C1-C4烷基或链烯基或芳基,n是1与4之间的一个整数。
3.根据权利要求1的组合物,其中R4含有一个或多个羟基和/或羧基和/或酯官能团。
4.根据权利要求1的组合物,其中化合物是:
[N(Me)x(CH2-CH2-OOC-T4)Y(CH2-CH2-O-R7)z]+X-
或
[N(Me)x((CH2)n-COO-T1)Y((CH2)n-COO-R8)Z]+X-
或
[N(Me)3-(CH2-CH(OOC-T4)(CH2-O-R9))]+X-
或
[N(Me)3-(CH2-CH(OR9)(CH2-OOC-T4))]+X-
或上述其中之一的一个胺的前体,
其中x+y+z=4
n是1与4之间的一个整数,
R7是H或-OC-T2;R8是H或T2;R9是R7或-OC-T4
T2按权利要求1中所定义,
T4是按权利要求1中所定义的T1,或是一活性物质基团,它在水解时产生一个活性物质和一个二酸,并且
x-是氯化物或Me硫酸盐。
5.根据权利要求1的组合物,含有含氮化合物,其中这个氮原子以一种环铵化合物和/或以它的一种胺的前体或以一种氧化胺的基团存在。
7.根据权利要求6的组合物,其中R4是(CH2)n或(CH2-CH2-O)nCH2-CH2-,并且R5是C1-C7烷基或链烯基或芳香基,n是1与4间的一个整数。
9.根据权利要求8的组合物,其中R4是(CH2)n或(CH2-CH2-O)nCH2-CH2-,R5是C1-C7烷基或链烯基或芳基,n是1至4之间的一个整数。
或它的一种胺的前体,
其中:
R1是Q′-T1或Q′-T2或T2或R6,
R2是Q″-T1或Q″-T3或T3或R6,
或
Q′和Q″的定义如Q,其中分别地R4是R4′或R4″,R5是R5′或R5″,
R3和R6相同或不同,是C1-C4烷基或C1-C4羟烷基或H,
R4、R4′和R4″、R5、R5′和R5″是任一取代或未取代无环或任何取代或未取代的单或多环有机基团或单或多杂环有机基团,
T1是一种活性物质基团,如权利要求1定义,
T2和T3相同或不同,是C5-C30烷基或链烯基或芳香基,X-是一个可相容的阴离子,
p是1与MWT1/50之间的一个整数,q是一个整数。
11.根据权利要求10的组合物,其中p为MWT1/1000-MWT1/100。
12.根据权利要求10的组合物,其中R4是(CH2)n或(CH2-CH2-O)nCH2-CH2-,R5是C1-C7烷基或链烯基或芳香基团,n是1与4之间的整数。
13.根据前述任一权利要求的组合物,其中T2和T3相同或不同,是C12-C22烷基或链烯基。
14.根据权利要求1-12中任一 的组合物,其中T1会产生一种活性物质,它选自一类羟基和/或羧基官能团香料成分、杀细菌剂、杀真菌剂、防汗剂、淀粉或改性淀粉、杀害虫剂、杀昆虫剂、驱虫剂或防腐剂。
15.根据权利要求14的组合物,它还含有常规织物调理剂或织物柔顺剂基质组份和添加剂。
16.根据权利要求15的组合物,它含有0.005-20.0%的活性物质基团。
17.根据权利要求16的组合物,它含有0.01-5.0%的活性物质基团。
18.根据权利要求16的组合物,它含有0.02-2.0%的活性物质基团。
19.根据权利要求15的组合物,它的pH值在2.0-5.0之间。
20.根据权利要求14的组合物,它还含有常规洗涤剂基质组份和添加剂。
21.根据权利要求20的组合物,其中X-是含有C7-C30烷基或链烯基团的阴离子。
22.权利要求15的组合物的应用,用于织物柔顺剂/调理剂基质中作为一种香料供给体系、杀细菌剂供给体系、杀真菌剂供给体系、防汗剂供给体系、杀虫或驱虫剂供给体系、或助熨烫剂供给体系。
23.根据权利要求20的组合物的应用,于洗涤剂基质中用作一种香料、杀菌剂、杀真菌剂、防汗剂、杀虫或驱虫剂或者一种衣物助熨烫剂的供应体系。
24.根据权利要求14的组合物,它还含有来自香波或头发调理剂或硬表面清洗剂或香料或除味剂或杀虫剂的常规基质组份或添加剂。
25.权利要求24的组合物的应用,用作一种香料供给体系、杀菌或杀虫/驱虫剂供给体系、杀真菌剂供给体系、一种防汗剂供给体系、一种防头屑剂供给体系或一种防腐剂供给体系。
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US4720383A (en) * | 1986-05-16 | 1988-01-19 | Quaker Chemical Corporation | Softening and conditioning fibers with imidazolinium compounds |
DE3734185A1 (de) * | 1987-10-09 | 1989-04-27 | Henkel Kgaa | Dicarbonsaeuremono-2(dodecyl(2-hydroxyethyl)-amino)ethylester, deren salze und deren verwendung als korrosionsinhibitor in waessrigen systemen |
JPH0317025A (ja) * | 1989-06-15 | 1991-01-25 | Nippon Oil & Fats Co Ltd | 徐放性活性成分放出剤 |
-
1994
- 1994-09-22 HU HU9600825A patent/HUT74082A/hu unknown
- 1994-09-22 CN CN94194130A patent/CN1078069C/zh not_active Expired - Fee Related
- 1994-09-22 ES ES94929306T patent/ES2179850T3/es not_active Expired - Lifetime
- 1994-09-22 JP JP51037795A patent/JP4030577B2/ja not_active Expired - Fee Related
- 1994-09-22 DE DE69431253T patent/DE69431253T2/de not_active Expired - Lifetime
- 1994-09-22 CA CA002171421A patent/CA2171421A1/en not_active Abandoned
- 1994-09-22 WO PCT/US1994/010748 patent/WO1995008976A1/en active IP Right Grant
- 1994-09-22 EP EP94929306A patent/EP0729344B1/en not_active Expired - Lifetime
- 1994-09-22 AU AU78409/94A patent/AU7840994A/en not_active Abandoned
- 1994-09-22 BR BR9407725A patent/BR9407725A/pt not_active IP Right Cessation
- 1994-09-22 CZ CZ96925A patent/CZ92596A3/cs unknown
- 1994-09-27 MA MA23661A patent/MA23339A1/fr unknown
- 1994-09-28 EG EG60194A patent/EG20670A/xx active
- 1994-09-30 TR TR01008/94A patent/TR28155A/xx unknown
- 1994-09-30 ZA ZA947664A patent/ZA947664B/xx unknown
-
1996
- 1996-03-29 FI FI961437A patent/FI961437A/fi unknown
- 1996-03-29 NO NO961294A patent/NO961294D0/no not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4429859A (en) * | 1980-05-14 | 1984-02-07 | Lesieur-Cotelle & Associes | Concentrated softening composition for textile fibers |
US4967547A (en) * | 1988-07-23 | 1990-11-06 | Fritz And Hans Stahlecker | Drafting unit for a spinning machine |
Also Published As
Publication number | Publication date |
---|---|
AU7840994A (en) | 1995-04-18 |
HU9600825D0 (en) | 1996-05-28 |
DE69431253D1 (de) | 2002-10-02 |
NO961294L (no) | 1996-03-29 |
EP0729344B1 (en) | 2002-08-28 |
JPH09503536A (ja) | 1997-04-08 |
FI961437A0 (fi) | 1996-03-29 |
ZA947664B (en) | 1995-05-24 |
CN1135172A (zh) | 1996-11-06 |
NO961294D0 (no) | 1996-03-29 |
EG20670A (en) | 1999-11-30 |
EP0729344A4 (en) | 1996-07-02 |
ES2179850T3 (es) | 2003-02-01 |
TR28155A (tr) | 1996-02-08 |
EP0729344A1 (en) | 1996-09-04 |
MA23339A1 (fr) | 1995-04-01 |
BR9407725A (pt) | 1997-03-04 |
CA2171421A1 (en) | 1995-04-06 |
JP4030577B2 (ja) | 2008-01-09 |
DE69431253T2 (de) | 2003-04-30 |
CZ92596A3 (en) | 1996-06-12 |
FI961437A (fi) | 1996-03-29 |
HUT74082A (en) | 1996-10-28 |
WO1995008976A1 (en) | 1995-04-06 |
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