CN101404892A - 微晶纤维素组合物 - Google Patents
微晶纤维素组合物 Download PDFInfo
- Publication number
- CN101404892A CN101404892A CNA038142627A CN03814262A CN101404892A CN 101404892 A CN101404892 A CN 101404892A CN A038142627 A CNA038142627 A CN A038142627A CN 03814262 A CN03814262 A CN 03814262A CN 101404892 A CN101404892 A CN 101404892A
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- CN
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- Prior art keywords
- hydrosol
- composition
- microcrystalline cellulose
- carrageenan
- mixture
- Prior art date
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Abstract
公开了超细微晶纤维素,该组合物包含共磨碎微晶纤维素和水溶胶。组合物的平均粒径小于10微米。组合物的制备方法是:在抗滑剂,最好是无机盐水溶液存在的情况下对高固体含量的微晶纤维素与水溶胶所组成的混合物施加高剪切力。组合物特别适用于食品、医药、化妆品和工业领域。
Description
本发明涉及微晶纤维素组合物、它们的制造方法和含有该组合物的产品。更具体地说,本发明涉及平均粒径小于10微米和包含结合紧密的微晶纤维素和至少一种水溶胶的颗粒状微晶纤维素组合物。该组合物的制备方法是:在抗滑剂存在的情况下通过对高固体含量的微晶纤维素与水溶胶组成的混合物施加高剪切力,对混合物进行强有力的捏合。
发明背景
微晶纤维素(MCC)是实际上没有有机和无机杂质的白色、无嗅、无味、流动相对自由的晶体粉末。它是一种纯化过的、部分解聚的纤维素,通常用矿物酸对来自纤维植物材料的纸浆α纤维素进行水解降解的方法来制取。它是一种高结晶度的颗粒状纤维素,主要由晶体凝聚体组成,这种凝聚体是除去纤维素材料中的无定形区(纤维状纤维素)后获得的。MCC应用于包括食品、医药和化妆品在内的各个领域。
微晶纤维素的生产方法是:用矿物酸,最好是盐酸,对纤维素原料,最好是以来自含纤维的植物材料的纸浆形式的α纤维素进行处理。酸有选择地攻击纤维素聚合物链上取向度较低的部位,从而使晶体部位暴露和游离出来,形成了构成微晶纤维素的晶体凝聚体。然后将这些凝聚体从反应混合物中分离出来并加以清洗以除去降解的副产物。所得湿晶体凝聚体,含湿率通常为40-60%,在本行业中有几种称谓,包括水解纤维素、水解纤维素湿饼、DP矫正纤维素、微晶纤维素湿饼或简称湿饼。
当湿饼干燥并脱水后,所得产物微晶纤维素是白色、无嗅、无味、流动相对自由的粉末,不溶于水、有机溶剂、稀碱或酸。微晶纤维素及其制备方法参见美国专利USP2,978,446。该专利描述了微晶纤维素作为药用赋形剂,尤其是作为压缩药片制造用粘合剂、崩解剂、流动助剂和/或填料的用法。
已经对微晶纤维素和/或水解纤维素湿饼作了改性,用于别的用途,主要是用作食品胶凝剂、食品增稠剂、各种食品的脂肪代用物和/或不含热量的填充剂,用作食品用悬浮稳定剂和/或变形剂,以及在药品、化妆洗剂及乳油中用作乳液稳定剂和悬浮剂。
为用于这些用途所进行的改性是通过对微晶纤维素或湿饼施加高强磨碎力,其结果使晶体得以完全再分割而产生细分颗粒。但是,当颗粒的粒径减少时,干燥过程中颗粒往往会发生凝聚或角质化,这很可能是因为较小的颗粒间存在氢键或其他结合力。为防止凝聚或角质化,可以在磨碎期间或磨碎后但在干燥前添加保护性胶体,如羧甲基纤维素钠(CMC),该添加剂完全或部分中和了导致凝聚或结块的结合力。这种添加剂还有利于干燥后材料的再分散。所得产物常被称为磨碎微晶纤维素或胶态微晶纤维素。胶态微晶纤维素的说明、制造方法和用途参见美国专利USP3,539,365。
胶态微晶纤维素为白色无嗅、吸水性粉末。在水中分散时,它成为白色不透明的触变性凝胶,微晶纤维素粒径小于1微米。它由FMC公司(FMC)生产和制造,在包括Avicel RC和Avicel CL在内的各种牌号下有不同规格,包含共同加工的微晶纤维素和羧甲基纤维素钠。
注意到食品添加剂中的CMC在某些人口众多的国家不受欢迎,McGinley在美国专利USP 4,263,334中避免在胶态微晶纤维素中使用CMC,而是采用由第一添加剂和第二添加剂组成的添加剂组合物,第一添加剂为碳水化合物甜味剂,如蔗糖、葡萄糖或水合谷物固体,第二添加剂为水溶胶,如瓜儿胶、槐树豆胶、阿拉伯胶、藻酸钠、藻酸丙二酯、角叉菜胶、刺梧桐树胶或黄原胶。
另一种MCC基稳定剂的说明参见Tuason等人的美国专利USP 5,366,742。这种稳定剂的制备方法是在水中使胶态MCC与藻酸钠混合,然后在浆料中添加可溶解的钙盐,其添加量可使藻酸钠、钙络合物在MCC表面沉淀出来,产生屏蔽涂敷性能。混合均匀后,对浆料加以喷雾干燥。用高强度剪切法可以使所得稳定剂在水中再分散,这种方法似乎破坏了藻酸钙的网络,因此可以发生分散。然而,为了用最小的搅拌力分散这种稳定剂,有必要使用钙多价螯合剂,以便优先与钠、钙络合物中的钙反应,使得藻酸盐稳定化。
并非所有的水溶胶都能在用以前的方法与MCC共同加工时使所生产的喷雾干燥粉末产生有效的隔离涂敷性能。McGinley等人在美国专利USP 5,192,569中描述了MCC与半乳甘露聚糖胶,如槐树豆或瓜儿胶共同加工的情况。在喷雾干燥前对MCC进行磨碎,因而成为胶态。但是,据称该絮凝产物是由粒径在0.1-100微米范围内的球状颗粒组成的。例如在实施例1中,喷雾干燥粉末的粒径范围为5-70微米。这种共同加工材料的再分散或再水合需要高剪切条件。在组合物中含有15wt%或15wt%以上半乳甘露聚糖胶时,对喷雾干燥材料的高强剪切分散导致纤维状颗粒的产生。无论是球状凝聚体还是纤维状材料,在赋予食品类似脂肪性能方面特别有效。
美国专利6,391,368(Tuason等人)公开了一种组合物,该配方包含磨碎胶态微晶湿饼,该胶态微晶与ι角叉菜胶共同加工并干燥。该组合物是用以下方法制备的:
(a)将水解过的纤维素单独进行磨碎,产生胶态微晶纤维素;
(b)将上述胶态微晶纤维素分散到热水中,水被加热到高于要与上述胶态微晶纤维素共同加工的ι角叉菜胶溶解温度的温度;
(c)将干燥的ι角叉菜胶添加到胶态微晶纤维素热分散体中并将各组分混合,产生浆料;
(d)使所述浆料匀质化;并
(e)干燥所述浆料产生共同加工的粉末。
USP 6,037,380(Venables等人)公开了一种组合物,该组合物包含微晶纤维素、较不溶于水的磨碎助剂和任选的保护性胶体。该组合物用以下方法制备:
(a)将未经过磨碎的微晶纤维素、较不溶解于水的磨碎剂和任选的保护性胶体混合在一起;
(b)对混合物进行高强剪切湿研磨些许时候,所用剪切力足以降低微晶纤维素的粒径,并
(c)回收所得超细微晶纤维素组合物。
USP 6,117,474(Kamada等人)公开了一种组合物,该组合物包含细小的纤维素和非水溶性含钙材料。组合物的制备方法为对纤维素颗粒的水悬浮液和含钙颗粒进行共研磨。可以掺入水溶性树胶和/或亲水物质,以防细小的纤维素和水不溶性含钙材料在干燥时再凝聚。
USP 6,270,830(Kamada等人)公开了一种肉产品用稳定剂,该稳定剂包含细小的纤维素和胶凝剂。稳定剂可包含钾盐或钙盐,如不溶于水的碳酸钙,以便控制胶凝。
发明概要
根据本发明,现在已经找到了一种制备胶态微晶纤维素/水溶胶组合物的方法,其中水溶胶的键非均匀分布,与以前所能达到的效果相比,水溶胶与微晶纤维素的混合能力更强,结合得更紧密。这种结果是在抗滑剂存在的情况下,用对高固体含量的微晶纤维素与水溶胶组成的混合物施加剪切进行强有力的捏合的方法获得的。
本发明组合物可以是从捏合工序回收到的经过湿磨碎的微晶纤维素/水溶胶固体;它也可以是用对该湿固体除湿的方法制备的干燥剩留物,后者优选是贮藏、运输和随后在制备微晶纤维素基分散体时使用之需要。在用以下所述方法测量时,组合物的平均粒径为小于约10微米。
发明的详细说明
根据本发明,提供了包含微晶纤维素和水溶胶的改进型组合物。该组合物的制备方法是(a)在水溶胶均匀溶胀之前,将微晶纤维素湿饼、水溶胶和抗滑剂混合,并(b)剪切该混合物。
所得组合物的特点是平均粒径小于过去在MCC/水溶胶组合物中所能达到的,并且根据所使用的水溶胶而具有独特的粒径分布。
水溶胶
在本发明组合物中可以使用任何与单独使用微晶纤维素相比,在与微晶纤维素混合时会增加表面电荷的水溶胶。这些水溶胶包括:角叉菜胶、琼脂、furcellaran之类的海藻多糖,藻酸酯和藻酸盐衍生物如藻酸丙二酯,和钾盐和钠盐之类的单价藻酸盐,包括半乳甘露聚糖在内的植物胶,如瓜儿胶、槐树豆胶和刺云实;羧甲基瓜儿胶、羧甲基槐树豆胶;魔芋粉(konjac)之类的葡甘露聚糖;罗望子;多糖;果胶;刺梧桐;金合欢;黄耆胶;黄原胶和出芽短梗孢糖之类的细菌多糖;结冷胶和wellan;纤维素胶;包括羟丙基甲基纤维素、羟乙基纤维素、羟甲基纤维素和羟丙基纤维素在内的烷基纤维素醚;以及它们的混合物。角叉菜胶可以包括μ、κ、κ-2、ν、ι、λ、θ角叉菜胶和它们的混合物。角叉菜可用无、低或高用量的碱加工。角叉菜可包括精制、半精制或未精制级的或它们的混合物。优选的水溶胶包括藻酸酯和角叉菜胶。当然,尤其优选(ι)角叉菜胶和藻酸钠。可以使用混合水溶胶,尤其是(ι)角叉菜胶或藻酸钠与少量黄原胶或果胶之类的其他水溶胶的混合物,只要抗滑剂能充分相互作用,对水溶胶混合物在微晶纤维素湿饼存在的情况下抑制水合,从而足以在剪切作用下转移足够的机械能来生产共磨碎胶态MCC/水溶胶。
用天然水溶胶可以得到最佳的结果。在此“天然”是指在自然界存在的或自然生成的,包括从植物、细菌等生物来源或微生物发酵中采集的水溶胶。
微晶纤维素
在本发明组合物中可以使用任何微晶纤维素。适用的原料包括,例如,木浆,如漂白的亚硫酸盐和硫酸盐纸浆、谷物壳、甘蔗渣、稻草、棉花、棉绒、亚麻、kemp、苎麻、发酵纤维素等。
根据对最终组合物性能要求,微晶纤维素和水溶胶的用量可以宽范围内变化。最常用的重量比应等于50/50到90/10,70/30到85/15更好。
抗滑剂
抗滑剂是一种非润滑材料,与水溶胶结合在一起发挥作用。使用抗滑剂时其用量应足以在加工时在设备的工作区域减少产品混合物的滑动量,即混合物机械加工期间在双螺杆挤出机的旋转螺杆部件之间以及挤出机螺杆部件与挤出机自身的筒体之间的滑动量。
在本发明中使用的抗滑剂可以是任何几乎完全溶解于水的无机盐。适用的能溶解于水的无机盐可以包括:例如,氯化钠、氯化钾、氯化钙、乳酸钙、酒石酸钙、柠檬酸钙、单磷酸钙和氯化镁。其中优选二价盐。特别优选氯化钙。
无机盐的用量取决于盐和所用的水溶胶的化合价。最小的用量就是该用量足以产生一种具有足够磨碎力的非滑动环境,使MCC凝聚体转变成胶态形式。如果盐的用量过多就会导致磨碎力太大,由此使温度上升而造成水溶胶降解。一般来说,其用量可占固体总重量的0.8重量%到3.0重量%。在一个用藻酸钠作为水溶胶、氯化钙作为无机盐的实施例中,当微晶纤维素与藻酸盐的重量比为85∶15时,氯化钙的添加量在0.8wt%-2.0wt%范围内,以1.0wt%-1.5wt%为好。在另一个用(ι)角叉菜胶作为水溶胶、用氯化钙作为无机盐的实施例中,当微晶纤维素与角叉菜胶的重量比为85∶15时,氯化钙的添加量在1.0wt%-3.0wt%范围内,以2.0wt%-2.5wt%为好。
在最终的组合物中一般要保持一定量的盐。当使用二价盐,如钙时,二价阳离子CA++的用量为基于粉末状组合物总重量的0.18-3.5%。这包括与所用的水溶胶缔结的任意重量的钙离子,因此可以大于加工过程中所用抗滑剂中的离子量。包含的阳离子量用以下所述的原子吸收法测定。
方法
在一个实施例中,本发明方法采用一种如上所述的水解微晶纤维素湿饼作为原料,含水40wt%-60wt%。边搅拌边将干粉状水溶胶添加到湿饼中。只有有限的水可以用来使在微晶纤维素湿饼与添加的水溶胶粉的高固体含量混合物中的水溶胶粉润湿并溶胀。在水溶胶开始水合,即开始润湿和溶胀后添加无机盐溶液。本发明一个重要的方面在于在水溶胶粉均匀润湿和溶胀前开始加盐。但是各组分的添加顺序并非极为关键的,比如可以在添加水溶胶前在MCC中添加无机盐溶液。无论哪种情况,随后都要对所得组合物施加剪切力(例如在双螺杆挤出机中)以强有力地捏合混合物和粉碎微晶纤维素凝聚体。在此所用的剪切力是指所施力的作用结果,导致或将导致混合物的两个接触部分在通常平行于它们的接触面方向上相互作相对滑动。当添加足够的盐时,水溶胶微晶纤维素混合物不再以滑动的形式做出响应,而是能够将受到的剪切力转化为机械能来粉碎微晶纤维素凝聚体。所用力量必须足以迫使微晶纤维素颗粒与水溶胶接触。
如果盐的添加量不足,化合物仍然发生滑动,因滑动作用剪切力主要作为机械能被消耗掉了,而不发生转化以粉碎微晶纤维素凝聚体。如果加盐过多,剪切阻力非常高,混合物中的水溶胶因局部发热而发生降解。
将所得剪切后的材料在水中加以分散、均匀化和喷雾干燥,产生最终的本发明组合物。
最方便的是,本发明用其中添加水溶胶的含湿率为40-60%的水解纤维素湿饼(即未干燥的物体,制作方法是用矿物酸处理纤维素原料,最好是来自含纤维植物的α纤维素纸浆,然后加以洗涤除去酸和副产物)作为原料之一。在水溶胶有机会均匀溶胀前,将水溶性盐的水溶液之类的抗滑剂添加到微晶纤维素湿饼和水溶胶混合物中。然后对部分水合的水溶胶和微晶纤维素颗粒的混合物进行高固体(含量)剪切,其中部分溶胀的水溶胶有利于微晶纤维素的磨碎以产生胶态颗粒。如果允许水溶胶在剪切前均匀溶胀,溶胀的水溶胶就会太滑而难以加工,在剪切期间就不会存在足够的能量转换,以产生必要的颗粒与颗粒的磨碎力,该磨碎力是在磨碎工序将微晶颗粒的粒径降低到一致的次微米大小所必需的。在制备湿混合物时,含湿量可以根据需要加以调节,以产生混合物磨碎所需的稠度,并可以在磨碎期间根据需要进行调节以保持需要的稠度。在一个优选的实施例中,湿饼中的含湿量通常足够了。要避免使用过量的水,因为它会降低颗粒与颗粒的磨碎力,而这种磨碎力是将微晶纤维素颗粒减小到一致的次微米粒径所必需的。
然后对湿混合物进行磨碎,最好在高剪切高固体混合条件下作为高固体含量湿混合物,其中微晶纤维素被研磨成超细次微米粒径的颗粒,这种颗粒的分散体为稳定的胶体。由于夹杂保护性水溶胶,胶态的稳定性得到进一步提高。
保护性水溶胶可以起到几种作用中的一种或多种作用。它们用作微晶纤维素颗粒间/或周围的保护层,据推测是连接于或取代了它们之间的氢键,因此在这种颗粒间形成了保护层以防它们角质化。其次,它们用作分散助剂,在干微晶纤维素的固体组合物再分散时协助微晶纤维素颗粒分散和再水合。此外,它们还有助于改变悬浮体的悬浮性和/或流变性。
最好用对高固体含量的微晶纤维素、无机盐溶液和保护性胶体的混合物进行湿剪切的方法将微晶纤维素的粒径减小到胶态粒径。使用标准挤出机,最好是具有多根螺杆的挤出机是减小微晶纤维素粒径优选手段。也可以使用其他标准设备进行湿剪切操作,诸如行星式混合机,例如Hobart混合机和辊式磨碎机,尤其是那些具有三根辊或多根辊的磨碎机。重要的是所用的设备产生了高剪切作用,并对微晶纤维素起到强有力的磨碎和磨擦作用,举例来说,其方法是迫使混合物通过横截面有限的通道,如在挤出机的多孔板和其他混合设备中找到的通道,或其他空隙有限的通道,如辊式磨碎机的辊子之间。优选挤出方法是因为它在该固体含量、高加工量的情况下操作简便,并能高效地产生非常细的微晶纤维素颗粒。
在本发明的方法中,第一道工序包括将未磨碎的微晶纤维素和水溶胶混合在一起。在进行高强剪切捏合前添加抗滑剂。如上所述,也可以在添加水溶胶前混合微晶纤维素和抗滑剂。
然后对湿混合物高强剪切捏合些许时候,条件为剪切力足以使微晶纤维素的粒径减小到某个粒径,其中约80%-100%,最好是约90-100%的微晶纤维素粒径不大于1微米,在含水介质中分散时呈胶态稳定。水溶胶与微晶纤维素结合紧密。
可回收用挤压法或其他适用的捏合方法生产的湿磨碎微晶纤维素组合物,然后作为悬浮和分散用稳定剂/悬浮剂加以分散并且/或者可以进行进一步加工、干燥,然后用于这种用途的分散。进一步的加工工序,如果使用,可以包括制备起始分散体、使所得分散体匀质化、干燥,例如采用喷雾干燥或其他适用的方法,所有干燥方法都在专业技术范围内。
取决于起始组分和它们在组合物中所占的比例,因此本发明组合物包含超细微晶纤维素组合物,该组合物包含抗滑剂和具有如上所述粒径的微晶纤维素颗粒以及保护性水溶胶,其中微晶纤维素与保护性水溶胶的重量比在约50∶50到90∶10范围内,最好是从70∶30到85∶15。
用在分散体、乳液、悬浮体等中的本发明超细胶体稳定微晶纤维素/水溶胶产品的用量占最终产品的约0.05-15wt%,以0.03-5wt%为好,0.05-3wt%最好,用作填料或膨胀剂时的用量为约1-15wt%。用于食品时,可采用0.05-15wt%。
组合物
用本发明方法制备的产品不同于那些用过去的方法制备的产品。与采用Kamada等人的方法和上述Venables等人使用固体磨碎助剂的专利方法制备的产品相比,本发明产品无机盐的分子分布遍及水溶胶/微晶纤维素组合物,而不是以精细的无机颗粒的形式(分布)。与胶态微晶纤维素紧密结合的交联水溶胶的非均匀分布使得再分散的粉末具有优异的流变性。较之以上述Tuason等人的方法,即预磨碎微晶纤维素和藻酸钠等组分仅仅在浆料中进行混合,这样添加水溶性二价金属盐时藻酸盐就能进行均匀的水合,然后在例如均质器中进行高强剪切,再进行干燥,从而将胶态微晶纤维素颗粒裹在藻酸钙胶基体中的方法,本发明产品胶态粒子更细,同时与藻酸聚合物紧密结合并非均匀交联,这是抗滑剂存在的情况下对微晶纤维素湿饼和部分溶胀的水溶胶进行了高强固体湿剪切的结果。
本发明的组合物被“共磨碎”意味着MCC和水溶胶是在对组合物施加高剪切力之前混合的。它们的物理性能特征是此前所未获得过的。
所有组合物均包含至少70%MCC,平均粒径小于10微米。在此所用的粒径是指用下述方法测得的值。优选的组合物具有取决于所用水溶胶的粒径分布(同样用下述测试方法测定)。特别是,
(i)当水溶胶是角叉菜胶时,至少50%的颗粒具有小于约3.5微米的粒径,
(ii)当水溶胶不是角叉菜胶的水溶胶时,至少30%的颗粒具有小于约3.5微米的粒径,和
(iii)当水溶胶是角叉菜胶与另一种水溶胶的组合时,其中至少20%的颗粒具有小于约3.5微米的粒径。
本发明的产品可用于经常使用胶态级MCC的场合,包括可蒸馏的巧克力饮料、烘焙性稳定的烘焙品填料、冷冻甜食、充气食品系统和色拉调料。这些产品特别适用于那些如含有新鲜大豆蛋白或大豆分离物、可可粉以及维生素和矿物质等营养添加剂的UHT加工饮料、乳品和非乳品。此外,这种新型胶态MCC产品扩大了产品的功能从而为胶态MCC创造了新机遇。新产品的用途归因于产品新的和/或改进了的性能。包括以下性能:降低了的与蛋白质的反应性,增加的在低pH值人工培养牛奶制品中的耐冻耐熔性,在UHT法制备的饮料中加工容限扩大而带来的改善了的悬浮体功能,增强了的在UHT奶油制品中的结构改良(作用)和提高了的在烘焙填料中的热稳定性。由于组合物与蛋白质的反应性降低,其用量可以减少,但具有更大的加工容度,因为有效性的的范围扩大了,故用量不是唯一的关键。干混产品(速溶调味品、肉汁、汤、速溶可可饮料等)、低pH值牛奶制品(酸奶油/酸奶、酸奶饮料、稳定化的冷冻酸奶)、烘焙食品(馅饼/糊状馅料)、饮料(柑橘味饮料等),和全部有标签的产品都是应用领域。其他用途为用作如花生白脱等非含水食品系统和低含湿食品系统中的膨化剂,用作咀嚼片剂、诸如APAP、阿司匹林、布洛芬之类的遮味药片用赋形剂,悬浮剂和药用受控释放剂。这些新型胶态产品也适合在食品、医药和农业领域(包括动物食品)中用作调味剂和营养组分用传输系统,以及用作直接压缩持续释放剂。它们还适合用在诸如药剂、膜和悬浮体之类的药物配方中。此外它们可在个人护理(皮肤、头发)用泡沫、乳液和洗涤剂中用作增稠剂,用作悬浮剂,与颜料和陶瓷中的填料、着色剂、化妆品和口腔护理品一起使用,以及在诸如陶瓷之类的工业领域、包括农药在内的杀虫剂用传输系统和其他农用产品中使用。
为了演示本发明,给出以下例子。
在各例子中,使用以下标准材料和测试方法:
I.“平均粒径”和粒径分布-
用Waring混合器(700系列)制备一分散体,使用一个1000ml的碗,用Powerstat变压器将速度控制在18000-19000rpm,这样做可以使Waring混合器的速度逐渐增加以免喷溅。
1.在一称盘中称取16g(±0.01g)粉末。
2.在500ml量筒中称取587±1g蒸馏水或去离子水并把它倒进混合器的碗内。
3.用变压器慢慢地将混合器的速度提高到约30伏。在水的中心加入粉末,注意防止粉末粘到碗壁上。
4.加完粉末后盖上碗盖混合15秒。
5.混合15秒后尽快将电压升到115伏,在115电压下混合2分钟。
6.将分散体贮存在500ml Nalgene瓶中。
用Horiba LA-910(购自Horiba instruments,Inc.,Irvine,Calif.)静态光扫描粒径分布分析仪测定平均粒径和粒径分布。
II.Ca++和氯化钙含量-用以下钙火焰自动吸收测试方法测定:
方法:
A.标准/空白试样制备:
1.用以下方法制备5%氯化镧:
准确称取12.5g 7水合氯化镧并移入含约100mL 0.1N盐酸(HCl)的250mL容量烧瓶。在超声波浴中放置10分钟,取出并冷却到室温,然后用0.1N HCl加到100mL刻度处。
2.用以下方法制备100-ppm钙储备标准液:
将10.0mL市售1000-ppm钙标准(Thermo Orion#92206,VWR#34813-182)移至含约50mL 0.1N HCl的100mL容量烧瓶内,摇匀并用0.1N加到100mL刻度处。
3.用以下方法制备2,4,7,10和16mL 100-ppm钙标准液:
将2,4,7,10和16mL 100-ppm钙储备标准液移至含约10mL 5%氯化镧溶液和约50mL0.1N HCl的带标签的100mL容量烧瓶内。摇匀并用0.1N加到100mL刻度处。
4.用以下方法制备空白溶液:
将10mL 5%氯化镧溶液移至100mL滴定烧瓶内,并用0.1N加到100mL刻度处。
B.试样制备:
1.对所有试样进行干燥失重(LOD)试验以测定含湿率。
2.将200mgMCC试样移至装有约50mL0.1N HCl的带标签的100mL滴定烧瓶内。
3.在超声波浴中放置30分钟,取出并冷却至室温。
4.添加10mL 5%氯化镧溶液并用0.1N加到100mL刻度处。
5.以3500rpm/5分钟的速度进行离心过滤并将上层清液移入13×100mm的培养管。
6.必要时用含0.5%氯化镧的0.1N HCl进行稀释,以获得钙标准曲线的范围在2-16ppm内的结果。
C.分析:
仪器:PERKIN-Elmer Analyst 300自动吸收能谱仪。
灯:钙
波长:422.8nm
信号测量:平均时间
火焰类型:空气/乙炔
氧化剂流量:10.0L/min
燃料流量:3.0L/min
狭缝宽度:0.7
读取时间:5秒
延迟时间:28秒
校准:直线
D.计算:
钙的重量(mg)=ppm钙·100·稀释因子/1000
钙%=(钙的重量(mg)/试样重量(mg)·(100-%LOD/100))·100
氯化钙%=钙%·(110.98/40.08)
III.烘焙(加热)稳定性-
用以下方法通过测量形状保持力来检验烘焙稳定性。形状保持力定义为在一定温度下烘焙一段规定时间后制备的水果馅料保持其原有形状和体积的能力。将准备好的规定体积的水果馅料(约35g)放在标准环(3.5cm)中,馅料,标准环放在带有同心刻度的纸上。在一通风的炉内水果馅料在特定温度下烘焙一段指定时间(一般为400°F 10分钟)。热处理后测定水果馅料的散开情况。散开情况用百分比表示[(最终直径-最初直径)/最初直径×100]。
实施例1
在5加仑Hobart混合器中,1744.9g固体含量范围为38-44%的微晶纤维素湿饼与90.8g ι角叉菜胶混合,使得MCC与ι角叉菜胶固体重量份数比达到90/10。添加27.7g浓度为30%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用)而易于形成胶态微晶纤维素颗粒。
将418.6gMCC/ι角叉菜胶挤出物分散在2581.4g160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度、所得干燥产品特性及随后的产量等进料性质调节喷雾干燥条件。
得到具有非常细的胶态颗粒尺寸分布的可水分散胶态MCC粉末。用激光衍射法进行的粒径分析表明粉末的平均粒径为5.33微米,85%的粒径分布小于3.5微米。在去离子水中分散时,其2.6%分散体的Brookfield粘度为1100cps,24小时后再测定的粘度为1150cps。
比较例1(无抗滑剂)
在5加仑Hobart混合器中,1744.9g固体含量范围为38-44%的微晶纤维素(MCC)湿饼与90.8g ι角叉菜胶混合,使得MCC与ι角叉菜胶固体重量份数比达到90/10。使混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切并对微晶凝聚体加以粉碎。所得挤出物的稠度很滑溜,因此没有在挤压机中得到必要的摩擦和功型,也就不能机械粉碎凝聚体而产生胶态颗粒。对挤出物的微观评价表明,MCC颗粒颗粒较大而且未磨碎,因此它们不呈胶态。
实施例II
在5加仑Hobart混合器中,1550.5g固体含量范围为38-44%的微晶纤维素湿饼与136.6gι角叉菜胶混合,使得MCC与ι角叉菜胶固体重量份数比达到85/15。添加40g浓度为30%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将584.4g MCC/ι角叉菜胶挤出物分散在2415.6g160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度、所得干燥产品特性及随后的产量等进料性质调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末。用激光衍射法进行的粒径分析表明粉末的平均粒径为4.27微米。在水中分散时,其2.6%分散体的初始粘度为1700cps,24小时后再测定的调整粘度为2450cps,这表明产生了有效的相互作用,即在MCC和ι角叉菜胶之间形成了良好的胶体网络。
0.5%浓度的这种85/15微品纤维素/ι角叉菜胶在可蒸馏营养药巧克力饮料和UHT加工大豆蛋白基巧克力饮料中能产生稳定的可可悬浮体。
比较例II(抗滑剂含量不足)
在5加仑Hobart混合器中,1539.3g固体含量范围为38-44%的微晶纤维素湿饼与127.6gι角叉菜胶混合,使得MCC与ι角叉菜胶固体重量份数比达到85/15。添加25g浓度为30%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度仍很滑溜,因此没有在挤压机中得到必要的摩擦和功型(作用),也就不能将凝聚体机械粉碎超细颗粒。对挤出物的微观评价表明,MCC颗粒颗粒较大而且未磨碎,因此它们不呈胶态。钙盐的添加量不足以与角叉菜胶竞争来争夺水,使角叉菜胶进一步溶剂化。
实施例III
在5加仑Hobart混合器中,1915.3g固体含量范围为38-44%的微晶纤维素湿饼与387.1gι角叉菜胶混合,使得MCC与ι角叉菜胶固体重量份数比达到70/30。添加75g浓度为30%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将309.3g MCC/ι角叉菜胶挤出物分散在2690.7g 160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末。在水中分散时,其2.6%分散体的初始粘度为2000cps,24小时后再测定的调整粘度为12900cps,这表明产生了有效的相互作用,即在MCC和ι角叉菜胶之间形成了良好的胶体网络。
用0.25wt%的这种70/30微晶纤维素/ι角叉菜胶粉末制备的加糖酸奶稠度平滑,结构光滑。在经受冷冻/解冻条件时,70/30MCC/ι基产品稳定,因为它保持其平滑性而且结构光滑。
实施例IV
在5加仑Hobart混合器中,1947.9g固体含量范围为38-44%的微晶纤维素湿饼与171.7g藻酸钠混合,使得MCC与藻酸钠固体重量份数比达到85/15。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将258.6g MCC/藻酸盐挤出物分散在2741.4g 160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末。用激光衍射法进行的粒径分析表明粉末的平均粒径为6.04微米。在水中分散时,其2.6%分散体的初始粘度为1675cps,24小时后再测定的调整粘度为1725cps。
实施例V
在5加仑Hobart混合器中,1938.1g固体含量范围为38-44%的微晶纤维素湿饼与168.9g完全改性的钙κ角叉菜胶混合,得到需要的MCC与κ角叉菜胶固体比。添加100g浓度为15%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将331.1g MCC/κ角叉菜胶挤出物分散在2268.9g 160°F的蒸馏水中。添加1.35gK2CO3并混合几分钟,将pH值调节到8.0-8.5。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末,其中50%的粒径在3.5微米以下。在水中分散时,其2.6%分散体的初始粘度为725ps,24小时后再测定的调整粘度为3.350cps。
用于UHT加工的营养巧克力饮料中时,所用浓度为0.10%的85/15MCC/κ角叉菜胶产生了稳定的可可悬浮体。
实施例VI
在5加仑Hobart混合器中,将1676.1g固体含量范围为38-44%的微晶纤维素湿饼混入100g30%CaCl2溶液,并混合数分钟。添加324.1g高甲氧基(HM)果胶,得到需要的MCC与HM果胶固体比。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将315.1g MCC/ι角叉菜胶挤出物分散在2684.9g 160°F的蒸馏水中。添加3gK2CO3并混合几分钟,将pH值调节到5.0-5.4。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末。用激光衍射法对其2.6%分散体进行的粒径分析表明介质粒径为6.56微米,平均粒径为8.98微米。在水中分散时,其2.6%分散体的初始粘度为675ps,调整粘度为975cps。
用于可饮酸奶中时,所用浓度为0.33%的85/15MCC/HM果胶产生了良好的稳定化效果。
实施例VII(70/30MCC/PGA)
在5加仑Hobart混合器中,将1089.8g固体含量范围为38-44%的微晶纤维素湿饼混入197.2g高酯化度(DE)的藻酸丙二酯(PGA)中,得到需要的MCC与PGA固体比。添加65g浓度为30%的CaCl2溶液并混合数分钟。混合物几次经过同时旋转的双螺杆挤压机,以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。将312.0g MCC/PGA挤出物分散在2688g 160°F的蒸馏水中。添加3g K2CO3并混合几分钟,将pH值调节到5.0-5.4。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以某个能产生需要的出口温度的转速将浆料喂入干燥器。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末。用激光衍射法对其2.6%分散体进行的粒径分析表明介质粒径为5.87微米,平均粒径为7.40微米。在水中分散时,其2.6%分散体的初始粘度为675ps,调整粘度为975cps。
用于可饮酸奶中时,所用浓度为0.35%的70/30MCC/PGA产生了良好的稳定化效果。
实施例VIII(75/15/10MCC/ι角叉菜胶/HM果胶)
在5加仑Hobart混合器中,1818.8g固体含量范围为38-44%的微晶纤维素湿饼与163.7g ι角叉菜胶混合,使得需要的MCC与ι角叉菜胶固体比。添加200g浓度为15%的CaCl2溶液并混合数分钟。混合物经过(一次)同时旋转的双螺杆挤压机。将108g高甲氧基(HM)果胶添加到MCC/ι角叉菜胶混合物中。该混合物数次经过挤压机以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将343.6g MCC/ι角叉菜胶/HM果胶挤出物分散在2656.4g 160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以一定的转速将浆料喂入干燥器以产生需要的出口温度。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末,其中21%的粒径在3.5微米以下。在水中分散时,其2.6%分散体的初始粘度为725cps,调整粘度为925cps。
用于加糖酸奶产品中时,用浓度为0.25%的75/15/10MCC/ι角叉菜胶/HM果胶生产的加糖酸奶稠度平滑,结构光滑。
实施例IX(75/15/10MCC/ι角叉菜胶/黄原胶)
在5加仑Hobart混合器中,1818.8g固体含量范围为38-44%的微晶纤维素湿饼与163.7g ι角叉菜胶混合,使得需要的MCC与ι角叉菜胶固体比。添加200g浓度为15%的CaCl2·2H2O溶液并混合数分钟。混合物经过(一次)同时旋转的双螺杆挤压机。将107.2g黄原胶添加到MCC/ι角叉菜胶混合物中。该混合物数次经过挤压机以便对混合物进行剪切,对微晶凝聚体进行粉碎。所得挤出物的稠度不是很滑溜,使之可以经受高功型(作用),从而易于形成胶态微晶纤维素颗粒。
将343.5g MCC/ι角叉菜胶/HM果胶挤出物分散在2656.6g 160°F的蒸馏水中。所产生的浆料经过压力为2500psi的Manton Gaulin匀化器并加以喷雾干燥而形成粉末。喷雾干燥在以下条件下进行:用口径0.1英寸(0.00254m)的自动喷嘴将匀质化后的浆料喂入3英尺(0.9144m)Bowen喷雾干燥器。用Moyno变速加料泵以一定的转速将浆料喂入干燥器以产生需要的出口温度。喷雾干燥器进口/出口操作空气温度为约195℃/95℃。根据粘度等进料性质、所得干燥产品特性及随后的产量调节喷雾干燥条件。
得到具有非常细的胶态粒径分布的可水分散胶态MCC粉末,其中26%的粒径在3.5微米以下。在水中分散时,其2.6%分散体的初始粘度为450cps,调整粘度为700cps。
实施例X
用下列组分制备水果馅料组合物。所有量均为重量份数。在本实施例中,使用以下材料:
GRINSTED LA410——购自Danisco的低酯酰胺化果胶。
COLFLO 67——购自National Starch的以蜡状玉米为原料的改性烹调淀粉。
木莓浓缩体——购自IFF的20%水果固体。
MCC/藻酸钠——用以上实施例IV所述方法制备。
组分 | 量 |
GRINSTED LA410 | 5 |
MCC/藻酸钠 | 5 |
水 | 420 |
糖 | 337 |
COLFLO 67淀粉 | 20 |
木莓浓缩体 | 200 |
山梨酸钾 | 1 |
3%乳酸钙水溶液 | 5 |
50%柠檬酸水溶液 | 7 |
固体白利糖度 | 43% |
热粘度,cP | 13800 |
烘焙稳定性 | 11% |
胶体强度,克 | 75 |
对GRINSTED LA410和MCC/藻酸钠进行干混,然后用高速剪切混合法在水中分散7分钟。边搅拌边将试样加热到90℃。在搅拌的同时添加COLFLO 67淀粉、糖和山梨酸钾的干混物。煮10分钟以确保淀粉分散,然后添加木莓浓缩体并对试样进行预热,在87-90℃温度下保温10分钟。用折射计测定白利糖度。依次添加乳酸钙和柠檬酸溶液。将水果填料倒入钟罩。1分钟后用Brookfield RVT#4转子以10rpm的转速测定热粘度。将试样冷却到室温并在测试胶体强度和烘焙稳定性之前加以冷冻。
Claims (31)
1.一种组合物,包含:
(a)至少70wt%微晶纤维素,和
(b)水溶胶
其特征在于组合物的平均粒径小于10微米。
2.权利要求1中所述的组合物,其特征在于
(i)当水溶胶为角叉菜胶时,至少50%颗粒的粒径小于3.5微米
(ii)当水溶胶为角叉菜胶以外的水溶胶时,至少30%颗粒的粒径小于3.5微米
(iii)当水溶胶为角叉菜胶与另一种水溶胶的组合时,至少20%颗粒的粒径小于3.5微米。
3.权利要求1所述的组合物,其特征在于其Ca++含量占组合物总重量的0.18-3.5wt%。
4.权利要求1中所述的组合物,其特征在于水溶胶的量等于水溶胶与微晶纤维素的总重量的15%-30wt%。
5.权利要求1中所述的组合物,其特征在于水溶胶为角叉菜胶。
6.权利要求1中所述的组合物,其特征在于水溶胶为藻酸盐。
7.权利要求1中所述的组合物,其特征在于微晶纤维素的量等于水溶胶与微晶纤维素的总重量的70%-85wt%。
8.权利要求1中所述的组合物,其特征在于它还包括水溶性无机盐。
9.权利要求8中所述的组合物,其特征在于无机盐的量等于组合物总重量的至少1wt%。
10.权利要求7中所述的组合物,其特征在于无机盐选自氯化钠、氯化钙、乳酸钙、酒石酸钙和单磷酸钙。
11.权利要求7中所述的组合物,其特征在于无机盐为氯化钙。
12.权利要求8中所述的组合物,其特征在于微晶纤维素和水溶胶是共磨碎的。
13.一种制备微晶纤维素组合物的方法,所述方法包括:
(a)形成高固体含量的微晶纤维素、水溶胶和抗滑剂的混合物,和
(b)捏合该混合物。
14.权利要求13中所述的方法,其特征在于微晶纤维素在添加抗滑剂之前先与水溶胶混合。
15.权利要求13中所述的方法,其特征在于微晶纤维素在添加水溶胶之前先与抗滑剂混合。
16.权利要求13中所述的方法,其特征在于水溶胶选自角叉菜胶和藻酸盐。
17.权利要求13中所述的方法,其特征在于水溶胶为角叉菜胶。
18.权利要求13中所述的方法,其特征在于水溶胶为藻酸盐。
19.权利要求13中所述的方法,其特征在于抗滑剂为无机盐的水溶液。
20.权利要求19中所述的方法,其特征在于无机盐为二价盐。
21.权利要求20中所述的方法,其特征在于二价盐为氯化钙。
22.权利要求19中所述的方法,其特征在于无机盐的量等于混合物中固体总重量的约0.8%-3.0wt%。
23.权利要求17中所述的方法,其特征在于抗滑剂为无机盐。
24.权利要求23中所述的方法,其特征在于无机盐的量等于混合物中固体总重量的1.0%-3.0wt%。
25.权利要求18中所述的方法,其特征在于抗滑剂为无机盐。
26.权利要求25中所述的方法,其特征在于无机盐的量等于混合物中固体总重量的0.8%-2.0wt%。
27.一种食品,包含权利要求1所述的组合物。
28.一种药物组合物,包含权利要求1所述的组合物。
29.一种化妆品组合物,包含权利要求1所述的组合物。
30.一种药物剂型,包含权利要求1所述的组合物。
31.一种工业用组合物,包含权利要求1所述的组合物。
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- 2003-05-14 CN CN038142627A patent/CN101404892B/zh not_active Expired - Fee Related
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CN111094423A (zh) * | 2017-09-08 | 2020-05-01 | 杜邦营养美国公司 | 微晶纤维素和藻酸盐的胶体组合物、其制备及由其获得的产品 |
CN110194446A (zh) * | 2019-06-10 | 2019-09-03 | 广西科学院 | 一种以纤维素深度水解得到的2d纤维素为原料的石墨烯2d粉体的制备方法 |
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AU2003234555A1 (en) | 2003-12-02 |
WO2003096976A2 (en) | 2003-11-27 |
JP2006508195A (ja) | 2006-03-09 |
US7462232B2 (en) | 2008-12-09 |
BR0309894A (pt) | 2005-03-22 |
JP5579578B2 (ja) | 2014-08-27 |
US20110135798A1 (en) | 2011-06-09 |
JP2014185347A (ja) | 2014-10-02 |
EP1575487B1 (en) | 2019-08-14 |
EP1575487A4 (en) | 2012-12-05 |
US8801847B2 (en) | 2014-08-12 |
US20140322282A1 (en) | 2014-10-30 |
ES2752452T3 (es) | 2020-04-06 |
BRPI0309894B1 (pt) | 2019-05-21 |
CN101404892B (zh) | 2012-04-04 |
EP1575487A2 (en) | 2005-09-21 |
JP2011046962A (ja) | 2011-03-10 |
AU2003234555A8 (en) | 2009-05-07 |
WO2003096976A3 (en) | 2009-04-09 |
US20060096500A1 (en) | 2006-05-11 |
US20090130287A1 (en) | 2009-05-21 |
BRPI0309894B8 (pt) | 2021-07-27 |
JP4808960B2 (ja) | 2011-11-02 |
US7871468B2 (en) | 2011-01-18 |
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