CN1055285A - 多重包封的香料释放体系和其制备方法 - Google Patents
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- CN1055285A CN1055285A CN91102082A CN91102082A CN1055285A CN 1055285 A CN1055285 A CN 1055285A CN 91102082 A CN91102082 A CN 91102082A CN 91102082 A CN91102082 A CN 91102082A CN 1055285 A CN1055285 A CN 1055285A
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
- A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/02—Apparatus specially adapted for manufacture or treatment of chewing gum
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/066—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the fat used
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/72—Encapsulation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/804—Low calorie, low sodium or hypoallergic
Abstract
一种用于将增强的香味和甜味提供给食物组合
物的流动细粒释放体系,该体系包括包封在一种基质
中的粉状香料组合物,该基质包括含有溶解度高达所
限定的一种强甜味剂的包覆层的亲水外包覆层,该释
放体系在口香糖类、食品类和药物制剂以及其他食物
制品中特别有用。
Description
本发明是本发明者的同时待审的其系列号为452,660(于1989年12月18日提交)的申请的延续部分,一方面该申请又是同时待审的其系列号为329,742(于1989年3月28日提交)的申请的延续部分,该申请又是同时待审的、系列编号为945,743(于1986年12月23日提交)的申请的延续部分,上述的后二者是以Subraman Rao Cherukuri和Gul Mansukhani的名称申请的。申请人要求所有的先有申请的利益。
本发明涉及用于香料的新释放体系和这种体系的制备方法,这种体系具有在多种产品中的用途,这些产品包括应用于象口香糖组合物、糖果、药物等可食物品、食物象饮料和一些烘制的食品等的食物产品、洁牙剂的组合物和托牙粘合剂中,以及在包庄中的应用。特别是本发明涉及促进香料有较高水平的释放和促进香料强度而没有以往在较高香料浓度时所感到的涩味和气味不佳的香料释放体系的制备方法。
香料释放体系在现有技术中是已知的,这种体系可按它们的物理状态即液状、乳状、糊状或固体状而分为许多类。不仅这些状态不同而且在将它们用于生产方法中时各状态的潜在用途也不同。
多年来的大量工作已针对香料物质的制备。特别是已经找到能提供较强香味并能长期持续释放香味的香料物质。
已经观察到这种活性的一个结果,是当将任意的香料油加到树胶基料中时,在咀嚼时只有大约5%至40%的原始香料油从树胶基料中释放出来。看来有80%之多的余下的香料油变为不可逆地与树胶基料结合而且不能咀嚼出来。
要克服特别是香料油的这种难题,已经进行过将香料油包封或应用干的成份以抑制树胶基料的结合作用等多种尝试。而且对于可延缓地释放香味剂同时使香味在一个较长的时间中均匀地释放出来的缓释香味剂的发展也已投入了大量的努力,立即和(或)延缓释放的明显得益是在于有能力在整个消耗期间提供均匀的香味感觉而这是以前通过将通常的调味料和香料油直接加到口香糖配方中而没有达到的。
喷洒干燥是用于包封或固定香料最广泛采用的技术。在这种方法中,通常将一种香料油与分散在水中的一种成膜剂混合,然后使之乳化而形成一种稳定的乳化液、乳化作用是必需的因为香料油并不溶于需要溶解成膜剂的水中。对于生产合格的产品来说在高固体含量时,得到一种低粘性乳浊液的要求是严格的。为了避免香料油的挥发在较高温度时对稳定性的要求也是严格的。如果香料在化学上是不稳定的,那么保持低的入口温度(在155℃左右)以及减少在干燥器中停留的时间是有利的。空气干燥的条件取决于乳浊液和产品的特性(如所需要的产品的颗粒大小)而定。也作过热应用的改良以从乳浊液中除去水份尝试,这些方法包括应用一种脱水溶剂作为干燥介质而不用热空气。已也仔细考虑过冷冻干燥法。
应用挤压法其中将香料油与水溶的糖或糖混合物共挤压、干燥和磨细以供应用,已达到了使香料固定。已发现这些产品可应用于作为与水接触而立即释出香味的干混合物中。这些产品通常含有10%至15%(重量)的香料油。
先有技术关于延长香味的广泛讨论可在Wei等人的美国专利4,590,075中找到。这些专利权的独得者讨论了一种在配制入口香糖之前与一定量的不受限制的疏水香料油一起加到一种悬浮剂中的包封的香料制剂(Marmo等人,美国专利3,920,849号);在高分子量物质如聚乙烯乙酸酯中包封的香料制剂(Ogawa等人,美国专利3,826,847号);通过水不溶的亲水聚合物如丙烯酸羟乙酯与香料交联而成的香料复合物制剂(美国专利3,761,286号);以及在口香糖表面的微封装的香料颗料与它们在淤浆中的分散液所成的制剂(美国专利3,962,463号)。另外,美国专利4,695,463号(Yang等人)记录和公开了一种香料释放体系,这种体系依赖一种在交联的水解胶体多价藻酸盐或角义菜胶基质中固定的香料。
再者,美国专利4,597,970(Sharma等人)制备了用于活性物如甜味剂和包括利用一种由可食用的脂肪酸或蜡、卵磷酯和一种甘油酯组分组成的疏水基质的香料的释放体系。这种体系提供一种保护性的阻挡层和控制释放所含的活性物质的特性。在包封的基质中的物质混合作用提供了有关非均匀的核心物质如糖精的湿润能力,同时提供了改进的热稳定性并因而延长了高温工艺运作的能力。这些属性经常是以延缓释放活性物的代价来达到的。
在美国专利3,867,556号(Darragh等人)中也在脂肪或蜡物质中包封挥发的香料。这些专利权获得者由于原来准备将它们的产品用于混入焙烧的商品中而发现原本的或基本的包封作用显示出对热的过度不稳定。它们应用了一种水溶的物质例如阿拉伯胶作第二层包覆,而提供了高温稳定性同时在与水份接触时使之具有快速的分解作用。Darragh等人的产品也显示了延缓的香料释放。
另外美国专利4,515,769号和4,386,106(均为Merritt等人)公开了在一种含有白明胶,一种天然胶(或白蛋白如在769专利中所公开的)或者在一种塑化剂的部分亲水基质中包封的香料物质。这种合并的包封剂被放入有香味剂的一种乳浊液中,然后干燥成一种固体的基质,再粉碎成一种基料粉末。然后将这种基料粉末用一种意图在与水分接触时防止香料损失和延缓香料释放的水不溶物质来包覆。Merritt等人只是寻找当物理咀嚼它们的香料组合物时裂开外层包封物质以达到爆出香料的目的。对于Merritt等人的发明,有关文献中他们的评述,也可以以积累的方式询问他们。
美国专利4,087,557号(Bakal等人)涉及将人造甜味剂直接加到口香糖基料的酯树胶组分中,以达到使甜味剂延缓和相应地延长的释放(31-42行第2栏)。该专利企图将某些香料,具体地说如食用酸类(如酒石酸、琥珀酸等)直接混入酯树胶组份中,但是该专利指出通常的香料如香料油在树胶基料组成物(包括含有人造甜味剂的树胶基料)中被互相混合和冷却以后再分别加入通常的多种香料如香料油。将香料组分混入按该专利以通常的方式制备的口香糖中,即通过直接混入人造香料和/或通过混入用亲水物质如阿拉伯胶包覆的香料(见Bakal等人,实例6)。因此Bakal等人并没有提供与香料释放和延长有关的技术难题的解决办法。
已有关于用其他途径特别是用香料油去制备香料组合物的记载,因而,美国专利3,041,180(Swisher)公开了一种用甘油和玉米糖浆固体挤出一种香料油以形成一种包封挤出的香料油的方法。将该固体干燥并产生细粒的固体。美国专利4,610,890号(Miller等人)公开了用糖、一种淀粉水解产物和一种乳化剂制备一种挤出的香料油的另一种方法。
美国专利4,448,789号和4,569,852号(Yang)公开了一种新的香味剂-亲水的聚合物此种香味剂是用香料与聚合物混合并在混合时加热以制备均相的产品。一旦偶合和碾细后,就可将该产物用作口香糖和糖果制品的香料。
美国专利4,271,202号(Giel)涉及一种用于形成一种每一总的颗粒单位重量可以含有高百分比的香料油的固体香料物质的喷洒干燥方法。由于可以有高的油含量,已发现这种喷洒干燥的产物在许多饮料和其他食物中都有广泛的用途。但是,也已发现由这种方法和相似的已知方法制备的喷洒干燥的香料,典型地显示出相对地有限的货架寿命。再者,已经发现,在喷洒干燥的程序中必然牵涉的高温,会损害香料和许多对热敏感的油性香料的香味如柠檬果的香味。此外,由喷洒干燥形成的固体通常显示出吸湿的特性,造成难于处理和贮存的问题。
除了美国专利4,452,821号(Gergely)的这些技术直接关系到糖果制品特别是口香糖之外,该专利还意图提供延长的、延续释放的香料香味和/或活性的药物成份。这是通过在一种固体溶液或在一种含官能团的蜡中的混合物,所说的蜡形成了一种固体溶液的均匀混合物。不含有任何官能团的蜡基本上是与香料、芳香或活性的药物成份不混溶的。
在以上讨论对香料改良的多种途径中,全都没有提供可达到香料强度的优点的和在香料油中与改良的释放和延长特性相结合的全部固有的优点的香料释放体系。在许多例子中,当改良的这类型的香料混到口香糖组合物中时,树胶基料和尤其是高弹体组分会隔绝香料因而阻碍了在咀嚼过程中香料的释出。而且,通常用于树胶配方中的增塑剂和软化剂易于增加水分的吸收以及相应的香料转移和损失。因此,在咀嚼时可能会有效地释放的香料在含量和所导致的延长释放以及味感方面都会进一步减少。
因此,从以上的讨论可看出,已经尝试过多种技术,包括从香料油与亲水的成膜物质混合而形成喷洒干燥颗粒,但是所得到的产物的被接受程度是有限的。如果混入高水平的香料油,所得到的产品会产生一种过分的涩味和苦味,并且可感觉到臭味。相反,如减少香料的强度以避免苦味而减少在颗粒中的香料浓度,这样就会造成必须将不希望有的大量颗粒加到特定的产物中藉以提供所期望的香味感。最后,不按照这些途径去处理,香味感的长期保持又会受到不理想的限制。
在共同指定的同时待审的编号为452,660的申请中,公开了一种甜味剂释放体系它应用一种由包覆有初级或第一种甜味剂的内部或核心,以及由具有一定量的甜味剂溶于其中的亲水聚合物溶液制备成的次外层包覆为基础的多层次包覆体系。该核心可由疏水或亲水的物质制成,然而外层包覆主要是一种水解胶体,在这个例子中的体系已被发展成提供保护并增进对于难处理的强甜味剂如糖精的前沿释放(up front delivery),并提供有利于保护与增进前沿和长期释放特性相结合的基本活性。
本发明寻求使申请编号为452,660的甜味剂释放体系的特性适应于香料的实例,以反映对可与较高的稳定性和活性的保护相结合的香料强度、表现、耐久性的改进和释放的香料释放体系的发展需要。
本发明公开了一种香料释放体系,该体系提供了一种改进性质的组合这种组合包括在该体系加到口香糖和其他产品中时,可改进香味强度和减少苦味,以及改进了香味的延长特性和释放特性。
释放体系的最后形式是一种细粒、自由流动物质、企图提供对可食用的组合物加强香味和甜味,所说的释放体系包括:
(a)包含一种颗粒状的香料的核心;和
(b)用于上述核心的一种包封基质,这种基质包括外层包覆一种含有强甜味剂的亲水聚合物,由亲水聚合物与甜味剂的溶液制备的外包覆层,存在于聚合物溶液中的甜味剂量的范围是约0.1%至50%(按上述溶液重量为基准)优选的是约3%至约15%(按上述溶液为基准),外包覆层存在量以核心重量计为约2%至约100%而优选的是约15%至约50%。
(c)其中封装的基质保护了在核心中的香料并使高浓度的香料包含于其中而没有将苦味赋予所形成的香料释放体系,并促进始终如一地释放香味。
本发明的释放体系预期一种实际上可用于任何香料制剂的释放体系,该释放体系包括用香料而特别是用喷洒干燥的香料油并用脂肪或蜡作外层包覆制备成的颗粒状香料,和用液体白明胶包封香料油制备成的微胶囊。核心中确切的组合物可以不同。
特别是该释放体系直接关系到用喷洒干燥的那些香料。名词“喷洒干燥的香料”的含意是包括由天然或合成的香味剂(如一种油或精油)被吸收入细粒载体介质如淀粉、阿拉伯胶、糖、麦芽糊精、玉米糖浆、多羟基化合物等等而形成的粉状产品。这些喷洒干燥的物质可用任何通常喷洒技术以及通过挤压、研碎或凝聚法来制成。
亲水外包覆层可以包括一种水解胶体。该水解胶体通常可从包括树胶类、果胶类、藻酸盐类、粘质类、成膜碳水化合物或它们的混合物组成的一组水解胶体中选出。
该亲水的外包覆层由于它的保护作用和由于相信是在最后的释放体系中存在着与含香料的核心处于紧密接触相联的甜味剂而使香料具有前缘释放(up front delivery)和减少香料苦味或臭气的混合优点。当有较大量的香料被包封而没有显现有害的苦味时会令香味的强度和释放增加,也促进了始终如的香气释放。香味的这些增量被保护而免于受降解的影响如在口香糖的情况下免受水份和与其他成份相互作用的影响,因而增进了香料的前缘和长期释放。
本发明的香料释放体系的另一特性和优点是所获得的颗粒显示出生物粘附性质,据信这种性质促进了所希望的两种活性释放的延长。因此,树胶薄膜的形成物被推理为用以包覆口部并因而是以生物粘附剂的方式起作用的。
本发明的释放体系发现了作为一种添加剂应用于食物和糖果产品中,它提供了香味和甜味的混合感觉。也对于两者的活性提供了同样的保护,因而对香味和甜味释放的强度和耐久性在感觉上就增强了。
可将释放体系加到多种糖果中(包括硬的和软的糖果、口香糖)和特别是低热量和低水分配方以及药物制剂中作为片剂包覆物的一部分,而在这种的新产品中作为“抓擦和吸气味”(“scratch-and-sniff”)以及香味包装。
本发明的香料释放体系可在多种食用产品中单独应用或与普通的香料(包括液体香料)、其他喷洒干燥的香料等、以及可取舍地选择的甜味剂混合应用。
在另外的具体实践中,本发明包括含有树胶基料、本发明的香料释放体系和可取舍地选择的甜味剂、填充料以及其他的添加剂的口香糖。所设想的含糖的和无糖的树胶,包括有高树胶基低碳水化合物含量的树胶。
因此,本发明的一个主要的目的是提供一种可释放高浓度的香料油而没有苦味的香料释放体系。
本发明的另一目的是提供一种可提供改进了香味强度和耐久性的上述香料释放体系。
本发明的另一目的是提供一种上述香料释放体系,该体系可提供对于在该核心中的香料有改良了的稳定性。
本发明还有一个目的是制备具有在其中包含有用以改进香味和甜味释放的人造甜味剂的香料释放体系。
本发明还有另一个目的是提供各在其中含有本发明的香料释放体系的口香糖或其他可食用的产品、药用产品或口腔卫生产品。
其他的目的和优点,从考虑根据以下说明性的图进行的随后说明,对于本专业的技术人员来说会变得很明显。
图1是用本发明的香料释放体系制备的胡椒薄荷香味口香糖的涩味与用普通的喷洒干燥胡椒薄荷香料制备的口香糖作为对照的涩味,作比较的比较图。
因此,本发明涉及一种香料释放体系,这种体系其最后的形式是一种提供了改进的香味强度和减少苦味的、以及改良了的香味延长和释放特性的细粒流动性材料该释放体系包括:
(a)一种包括细粒形式香料的核心。
(b)用于该核心的一种包封基质,这种基质包括含有强的甜味剂的亲水聚合物的一种外包覆层,该外包覆层由亲水聚合物与甜味剂的溶液制成,对于存在于聚合物溶液中的甜味剂其含量范围是约0.1%至约50%(以上述溶液重量为基准),而较好是约3%至约15%(以上述溶液为基准),外包覆层的存在量为约2%至约100%(重量)而较好是约15%至约50%(按核心重量计);
(c)其中的包封基质保护了在核心中的香料并让高浓度的香料包含于其中而没有将苦味赋与制成的香料释放体系,并促进了始终如一的气味释放。
正如以前所讨论的,该核心可以用不同的方法来制备,并可包含用直接或用混入或以一种固体载体组合物的方法配成细颗粒形式的所有香料。可用多种已知的香味剂来制备核心,该核心可包含亲水和疏水载体或包封物质。核心的香料含量可以不同,并可以有从约5%至约90%核心重量的宽范围,而较好是约1%至约30%的核心重量。
适合的香料可包括合成香料液体,如合成的香料油和香味的芳香剂和/或油;和/或液体;油树脂或从植株、叶子、花、果实,等以及它们的混合物而来的萃取物。较好的是,可选自留兰香油、肉桂油、冬绿油(甲基水杨酸酯)和薄荷油、丁香油、月桂油、茴香油、按树油、百里香油、柏木叶油、肉豆蔻油、众香子油、鼠尾草油、肉豆蔻衣油、苦杏仁油和中国肉桂皮油。当然,多种人造的、天然的或合成的果香香料也是预期的如留兰香油和柑桔属油包括柠檬、橙、葡萄、白柠檬和圆柚,而果香香精油包括苹果、梨、桃、葡萄、草霉,复盆子、樱桃、李、菠萝、杏仁等等的精油。
在应用亲水包封物质的实例中,适合的物质包括糖和多元醇以及多种水解胶体如树胶类、果胶类、藻酸盐类、粘质类、成膜碳水化合物,以及混合物。在其载体或包封物质是疏水的实例中,适合的疏水物质包括脂肪类和蜡类。
适合的脂肪包括脂肪酸类如氢化的或部分氢化的油,其有代表性的物质包括棕榈油、棕榈核油、黄豆油、棉子油、花生油、油菜子油、米糠油、向日葵子油、红花油和它们的混合物,也可作脂肪用的其他物质可由单甘油酯类、二甘油酯类、三甘油酯类、多甘油酯类、山梨醇酯类以及它们的混合物中选中。
适合的蜡包括天然蜡、合成蜡和它们的混合物,特别是包括从石蜡、蜂蜡、巴西棕榈蜡、小烛树蜡、羊毛脂蜡、月桂子蜡、甘蔗蜡、矿脂蜡、聚乙二醇、鲸蜡、米糠蜡、微晶蜡和它们的混合物中选出的蜡。
当然,对于上述包含于核心的包封介质中的适合物质,以上所述只是说明性的而不是限制性的,而本发明考虑扩展未名命的等同物质于本发明的范围内。
具体地说,可制备多种组合的核心,如在编号为393,442的同时待审的申请中公开了一种核心,其中将一种香料和一种树脂如松脂的混合溶液用喷洒凝固的方法相继地包封在一种含有脂肪和蜡的包封基质中。另一种可选择的制剂包括如在美国专利4,597,959(Barr)中所公开的一种微胶囊制剂。这一公开的内容已加入本文作为参考。
具体的说,将液体香料做成小液滴,然后被处理成可由白明胶和粘合剂(如阿拉伯树胶)、一种白明胶交联剂(如戊二醛)和硅酸纳制备的微胶囊。该香料物质可由85-95%(按微胶囊重量计),以及包括余下部分的包封壁物质构成。当然,以上的核心配方仅为说明性的而不应被认为限制本发明的。
在具体的实施中,可以用多种香料组合物通过单独喷洒干燥或与固体载体组合物联合干燥来制备核心。虽然多种其他的普通物质都可应用作为固体载体,但糖和多元醇是用作喷洒干燥香料的最普通的载体。对于任何方式的本发明来说,个别的粉末香料组合物并不是关键性的。通常,喷洒干燥的香料组合物将有约50%至95%(重量)的载体量存在,以及包括香料油和精油的其余部分。释放体系的核心是粉状香料组合物。除了香料组合物外,可加入任何数量的附加成分如甜味剂、药物、填充剂等等。
核心周围是一种包封的亲水基质。亲水基质包含有一种含有强甜味剂的亲水聚合物的外包覆层,该外包覆层由亲水聚合物和甜味剂的溶液制成,在聚合物溶液中的甜味剂存在量其范围从约0.1至约50%(以上述溶液重量为基准计),而较好是从约3%至约15%(以上述溶液为基准计),外包覆层的存在量从约2%至约100%(重量)而较好是从约15%至约50%(按核心重量计)。
本发明的核心和包封基质可用水解胶体来制备,适合的水解胶体通常可从由树胶类、果胶类、藻酸盐类、粘质类、成膜碳水化合物和它们的混合物组成的胶体组中选出。
具体来说,水解胶体可以是从由阿拉伯胶、黄蓍胶、刺梧桐胶、茄替胶、琼脂、角叉菜胶、fucellan、欧车前胶和它们的混合物组成的胶体组中选出。水解胶体也可以从聚乙烯吡咯烷酮、白明胶、聚葡糖、xanthin、curdan、纤维素、甲基纤维素、乙基纤维素、羟乙基纤维素、羟丙基纤维素、羟丙基甲基纤维素、羧甲基纤维素、低甲氧基果胶、丙二醇藻酸酯、聚葡糖、改性淀粉、麦芽糖糊精和它们的混合物中选出。
甜味剂可选自天然的和合成的强甜味剂,而在较好的实施中可包括至少一种第一种固体天然的或人造的、从由氨基酸基的甜味剂、蔗糖的氯衍生物、二氢黄素醇、羟基愈创木酚酯类、L-氨基二羧酸偕二胺类、L-氨基二羧酸氨基链烯酸酯酰胺类、二肽甜味剂类、甘草甜、糖精及其盐、acesulfame盐类、环磺酸盐类、蛇菊苷类、talin、二氢查耳酮类化合物和它们的混合物组成的甜味剂中选出的高强度甜味剂,在此应用同一甜味剂组中的一种作为甜味剂。
本发明的优点之一是外包覆层可提供对于活性的保护并在同一时候通过让高浓度的香料被包含于其中而大大地加强前缘香料释放(up front flavor release)而不显现苦味和涩味。据信这至少有一部分是由于存在的强甜味剂处在含香料的核心的邻近处的造成的,但是在同时,包封的基质得到了改进,因为它是很有效的,虽然它被施用并且主要以从经常用作核心物质的外包覆层的脂肪/蜡包覆层中减为出来的量存在。
根据本发明的另一实施,包括用于制备在调节香料的释放和对香料提供较大的保护的同时可提供较大的前缘香料(up front flavor)的香料释放体系的一种方法,该方法包括:
(a)形成含有香料的细颗粒核心;
(b)通过一种流化床一型的方法用包封基质包覆所得到的细颗粒核心,所说的包封基质包括一种含有强甜味剂的亲水聚合物的外包覆层,所说的外包覆层是由亲水聚合物与所说的强甜味剂的溶液制备的,所说的强甜味剂在聚合物溶液中的存在量范围从约0.1%至约50%(按所说的溶液重量计),外包覆层的存在量为约2%至100%(按所说的核心重量计);以及
(c)回收最后的复合包覆的颗粒;
(d)其中包封的基质保护了在核心中的香料并让较浓度的香料被包含于其中而不会把苦味赋予所得到的香料释放体系,并促进始终如一的香味释放。
本发明的释放体系的制备以核心香料颗粒的制备开始、这种制备过程可根据要制备的核心颗粒而改变。例如核心可以包含喷洒干燥的香料如用载体(如阿拉伯胶或白明胶)制备的那一种。该香料核心也可以用脂肪和/或蜡来制备,在这种情况下制备过程可包括喷洒凝固过程。
本发明的组合物的制备下一步是通过形成强甜味剂与亲水包覆物质的水溶液混合物而制备包封基质的溶液。因而,亲水的包覆物质水溶液是通过例如将亲水包覆物质放在去离子水的溶液中来制备。然后将甜味剂加到所得到的溶液中以形成水溶液混合物。在整个外包覆层的制备过程中,温度可保持在约50°至约60℃。
此后,将包括核心的本发明的释放体系的颗粒用包封基质或外包覆层包覆。将外包覆层敷于核心颗粒,可用美国专利4,384,004(Cea等人)所公开的用于这类型的物质的相同技术来完成。从而可应用包括流化床包覆方法等多种包覆技术。较好的包覆方法是流化床方法,其中将核心物质颗粒悬浮在能产生一股向上的气流的设备中颗粒就在气流中运动。该股气流通过一个细喷雾的包覆物质区,在此使通过的颗粒被包覆,在此之后包覆的颗粒在一个流体化条件的逆流中从向上的气流移动并运行向下到达一股在其中这些颗粒被干燥的热流动气流中。这些颗粒可以再进入向上气流以进一步包覆或可从包覆的装置中排出。这个典型的方法和装置是已知的Wurster方法而在以下的美国专利作了详细的说明。已将这些专利的公开内容加入本文作为参考:美国专利3,089,824号;美国专利3,117,027号;美国专利3,196,827号;美国专利3,241,520号和美国专利3,253,944号。
外包覆层的包覆操作可在温度低于大多数包封方法并因而大概不会破坏被处理的颗粒的温度水平进行。特别是外层包覆方法可在入口温度为100°至125°F的水平进行,因此在包覆程序中所发生的是相对温和的颗粒加热。当然,这个温度可以改变而最适温度的选择属于工艺的技术的问题。
如上所述,供使用的外包覆层是由能被均匀地喷雾的液体的形成来制备的、因此,可将水溶的水解胶体物质制成水溶液。如有需要,可加入其他成份如增塑剂以改进最终的包覆层的性质。适当的增塑剂包括癸二酸的甘油酯,邻苯二甲酸二乙酯、三乙酸甘油酯,柠檬酸三丁酯、乙酸甘油单酯、柠檬酸单甘油二酯、己二酸酯以及其他。可以将在本发明范围以内已知有效量的增塑剂加于其中。
可将快速释放体系加到一些的可摄取的产品如糖果类等等以及口香糖组合物、药物制剂和托牙产品中。
所制得的本发明的化合物是粉状或粒状的。颗粒大小对于释放体系并不是关继问题而且可调节至适应于所需的释放速率的细粒大小和口感,这取决于释放体系所混入的载体例如口香糖、糖或药剂。这种产品可被用作多方面的用途,如用作烘制物品的冠面或者用作托牙粘合剂的添加剂。包覆基质对于除香料以外的多种核心物质有用,如需要包覆以作为保护、控制释放或作气味掩盖用的甜味剂,药物和其他的细粒物质。
在另外的实施中,可将香料颗粒直接与包封基质混合物混合然后展开成片,使其冷却后再研碎成用于食物制品的适当大小的颗粒。但是,这个方法有缺点,因为研碎时易于分离环绕着香料颗粒的包覆层的连续性并会导致由于包封基质和香料颗粒本身之间紧密相接触而提供的保护性受到破坏。因此,当在实施本发明的时使用,较好是使用如上所述的流化床包覆法。
正如以上所述,亲水的包覆层提供了防止在香料颗粒与存在于细粒产品中的其他组分或化学品之间进行相互反应的保护性屏障,以及提供了增加会在高浓度显示苦味的某种香料的含量的办法。然而使这种亲水的包覆层有特定的厚度并不是关键性的,只应该是有效地包覆这些香料颗粒即可。如果需要增加包覆,可以让释放体系的颗粒悬浮在空气流中就可进行进一步用溶液喷洒外包覆层。
本发明的香料释放体系可用于许多可食的制品中,在这些可食的制品中特别是口香糖、糖果、药物制剂以及其他食物产品如焙烧的商品,通过本发明的释放系统提供的增强香味/甜味将使这些可食用的制品受惠。
关于应用了新的释放体系的口香糖配方,所应用的树胶基料量在很大程度上取决于多种因素如所用的基料类型、所要求的连续性和用来做成终产物的其他成份。通常,将约5%至约45%的口香糖组合物成品重量的量用于口香糖组合物中是可以接受的量而优选的量是约15%至约25%(重量)。树胶基料可以是任何水不溶的在技术上已知的树胶基料。在树胶基料中,适合的聚合物的说明性实例包括其他天然的和合成的高弹体和橡胶、例如在树胶基料中适合的那些聚合物包括(但没有限制)由植物来的物质如糖胶树胶、节路顿胶、古塔波橡胶和皇冠胶。合成的高强性如丁二烯-苯乙烯共聚物、异丁烯-异戊二烯共聚物、聚乙烯、聚异丁烯和聚乙烯乙酸酯和它们的混合物是特别有用的。
树胶基料组合物可以含有高弹体溶剂以帮助软化橡胶组分。这些高弹体溶剂可以包括甲基、甘油或松香或改性松香的季戊四醇酯,如氢化的、二聚合的多聚合的松香或它们的混合物。适用于本发明的高弹体溶剂的实例包括部分氢化的木松香的季戊四醇酯、木松香的季戊四醇酯、妥尔油松香的甘油酯、木松香的甘油酯和部分氢化的木松香和部分氢化的松香甲基酯,如α-蒎烯和β-蒎烯的聚合物。萜烯树脂类包括聚萜烯和它们的混合物。应用的溶剂量范围从约10%至约75%而较好是约45%至约70%(按树胶基料的重量计)。
可应用多种传统的成份如增塑剂或软化剂如羊毛脂、硬脂酸、硬脂酸纳、硬脂酸钾、三乙酸甘油酯、甘油等等,以及天然蜡类和石油蜡类如聚氨基甲酸乙酯蜡类、石蜡类和微晶蜡类。这些成分都可以混入树胶基料中以得到多种所需要的结构和稳定的性质。这些添加的物质通常是单独地应用和较好是以高至约30%(重量)的量而较好是从约3%至约20%(重量)的量(按最终的树胶基料组合物的重量计)混合。
口香糖组合物可再包括通常的添加剂如甜味剂、染色剂如二氧化钛;乳化剂如卵磷酯和甘油单硬脂酸酯;以及添加的填充物如氢氧化铝、氧化铝、硅酸铝、碳酸钙,滑石粉和它们的混合物。这些填充物也可以不同的量用于树胶基料中。在应用填充物时的优选量改变可从约4%至约30%(按口香糖成品重量计)。
在应用辅助香料的实例中除了在释放体系中的辅助香料之外,本发明预期包含本技术领域中已知的那些香料,即预期包括天然和人造的香料,薄荷类如胡椒薄荷、薄荷醇、人造香兰素、肉桂、各种果香香料,单独的和混合的等等。通常应用的香料用量的改变取决于个别的香料,用量的改变范围例如约0.5%至约3%(按口香糖组合物成品重量计)。这些香料可存在于释放体系中或在口香糖组合物本身中或者同时存在于两者之中。
可独立加入的适当的甜味剂包括天然的和人造的甜味剂。因此甜味剂可选自以下没有限制的名单:糖如蔗糖、葡萄糖(玉米糖浆)、葡萄糖、转化糖、果糖和它们的混合物;氯化蔗糖化合物如sucralose和它的衍生物;糖精酸和它的多种盐如糖精钠或糖精钙;环己烷氨基磺酸和它的多种盐如钠盐;二肽甜味剂如糖精和其已知有甜味的衍生物;二氢查耳酮化合物;甘草甜;斯替维亚属rebaudiana(卡哈苡苷);和糖醇类如山梨醇、山梨醇糖浆、甘露醇、木糖醇等等。这预期作为甜味剂的是已公开在美国再颁发的专利26,959号中的非发酵的糖取代物(氢化淀粉水醇物);和合成的甜味剂3,6-二氢-6-甲基-1,1,2,3-氧噻嗪-4-酮-2,2-二氧化物,特别是如在德国专利2,001,017.7号中所叙述的它的钾盐(Acesulfame-K)、钠盐和钙盐。
用于本发明中的染色剂包括颜料如氧化钛,并可用高达1%(重量)的量混入而较好是用高达约0.6%(重量)。染色剂也可包括共他适于食物、药物和化妆使用的染料,和已知的F.D.&C.染料等等。在以上所列的用途中可接受的物质较好是水溶的。说明的例子包括已知为F.D.&C.兰2号的靛类染料,它是5,5′-靛兰二磺酸的二磺酸的二钠盐,类似的,已知为F.D.&C.绿1号的染料包括三苯基甲烷染料,是4-〔4-N-乙基-对磺基苄甲氨基)二苄基亚甲基〕-〔1-(N-乙基-N-对锍苄基)-2,5-环己二烯亚胺〕,在kirk-Othmer著的Encyclopedia of Chemical Technology第5卷,857-884页记载了所有F.D.&C.和D.&C.以及其他相应的化学结构的详尽说明,因此将这一材料加到本申请中作为参考。
本发明的口香糖可以是本技术中已知的任何形式,如棒状的、厚片的、大块的、碎条的、硬包覆的、小片的、以及中心填充的形等形式的口香糖。
本发明也包括制备改进了香料强度和持续释放香料性质的口香糖组合物的方法,该方法概括地包括:
(1)制备本发明的香料释放体系;
(2)将第一步制成的香料体系加到树胶基料和余下的口香糖成份的混合物中;
(3)使所得到的混合物形成适当的口香糖形状。
更具体地说,制备根据本发明的口香糖组合物的方法如下:首先,将树胶基熔融(约85°至90℃),冷却至78℃并放在一个预热(60℃)的装有∑刀片的标准混合锅中,加入一种乳化剂(卵磷酯)并混合之。另外,加入一部分糖醇(山梨醇)和软化剂(甘油)并再混合3至6分钟。将混合的锅冷却然后再加入甜味剂(甘露醇)、余下的山梨醇和甘油并继续混合。在此时未加香料的口香糖温度约为39-42℃。然后加入含有核心物质的香料释放体系并混入基料中,再继续混合1至10分钟。此时口香糖成品的温度是39-43℃。然后将口香糖组合物从锅中卸出,辊压、划痕并形成口香糖片。
以下的实例用作提供进一步理解本发明但并不意味着以任何方式限制本发明的有效范围。整个说明书所用的全部百分数除了另有指示外都以释放体系成品的重量百分数计算。
实例1
根据以上所述的方法制备本发明的释放体系。具体来说,用通常的喷洒干燥方法制备重量为500g的核心,包括用含有20%重量的胡椒薄荷香料,用余下的阿拉伯树胶作为载体的一种包封。
通过将阿拉伯树胶加到去离子水中以形成溶液用一种强甜味剂制备285.7g量的包封基质。然后将甜味剂acesulfame-K加到所得到的溶液中以形成作包覆用的水溶液。制成的包覆溶液含有10%阿拉伯胶,20%acesulfame-K和65%去离子水。
然后用流化床包覆的方法将包封基质敷在核心上。因此,至此已准备好将包覆物质送到一种可喷洒凝固的装置(Glatt GPCG-1)流化床粒化器中,此装置将被用来包覆粉状喷洒干燥香料的流化床。将香料颗粒悬浮在粒化器的冷空气气流中,在此冷空气气流中包覆物质被喷洒出或喷成雾状。在用较冷的空气温度和流化的香料颗粒接触的基础上,熔融的包覆物质固化在香料颗粒上并穿出向上的气流。调节喷咀压力和温度以控制终颗粒小滴大小。
所得到的是具有椭圆形或球形的干颗粒或团块(在此称为释放体系)。然后,释放体系颗粒被筛分以作具体的应用或使之留在粒化器中以得到进一步包封的包覆。当干燥时,所得的颗粒被测定为含有7.27%acesulfame-K和12.73%香料(以释放体系成品的干重计)。
实例2
根据本发明另一个释放体系是根据早先概述的普通方法制备的。具体来说,在这个实例中重量为500g的核心是通过喷洒凝结来制备的,它包括含有20%(重量)的胡椒薄荷香料以及余下物质是一种脂肪/蜡和一种乳化剂,所有都是根据先有申请系列号393,442。
至于先前的实例,含有包封基质的285.7g阿拉伯树胶是用强甜剂acesulfame-K在一含有65%去离子水,15%阿拉伯树胶和20%acesulfame-K的混合物中制备的,然后通过流化床包覆过程将包封的基质敷到核心上。并将包覆物送入一个喷洒凝固装置(Glatt GPCG-1)流化床粒化器中。将香料颗粒悬浮在粒化器中并将熔融的包覆物配置并固化在香料颗粒上以形成所得到的干颗粒或团块。在干燥时,测定颗粒成品含有7.27%acesulfame-K和12.73%香料(二者均按释放体系的干重计)。
实例3
在此实例中另一个可供选择的释放体系是通过制备包括根据美国专利4,597,959的方法制备的微包封的香料小珠的核心来制备的。在此实例中其小珠含有85%香料而余下的是白明胶的包覆组合物。
然而将此小珠用由阿拉伯胶和acesulfame-K制备的基质包覆成500mg重。该基质含65%去离子水、15%阿拉伯胶和20%acesulfame-K。然后将该包封的基质通过以上讨论的流化床包覆步骤敷到核心上,在干燥时,测定所得的颗粒含有62.96%香料和14.81%acesulfame-K(以释放体系成品的干重计算)。
实例4
根据本发明的方法制备两种胡椒薄荷香味的树胶组合物,并正如在以上所讨论的关于口香糖组合物的制备。口香糖组合物各含有等量的游离的液态香料以及样品A含有按上述实例1制备的包封香料,而对照样品B则含有一定量的喷洒干燥的香料和游离的acesulfame-K。以下表1中说明了各个树胶组合物样品的配方。
表1
成份 样品A 样品B
树胶基料 26.000% 26.000%
碳水化合物 59.872% 61.015%
软化剂 9.350% 9.350%
液体香料 0.850% 0.850%
喷洒干燥的香料* - 2.500%
Acesulfame-K(游离的) - 2.285%
实例1包封** 3.928% -
*20%(重量)负载于喷洒干燥的香料上的液体香料
**2850ppm acesulfame-K,500ppm液体香料负载
一次配制份量大小:2000g
两种组合物都被配制成一次配制的份量大小为2,000g,然后再形成最后供使用的形式。然后再使这些树脂经受品味比较试验,如果有任何涩味被专家小组觉察的话则要评估涩味量。在图1中说明了比较试验结果。
从图1的评述,含有本发明的包封香料树脂(样品A)显示一致的低涩味经历的时间,比应用游离的accsulfame-K和未包覆喷洒干燥的胡椒薄荷香料的对照树胶组合物要长,正如早先所指出的,将两种组合物制备成含有相同香料量和acesulfame-K甜味剂,从而象本发明的香料释放体系那样清楚的表现出有减少涩味的能力。有这种减少涩味也就有一种含有较大量香料的能力和因而在咀嚼时有增加香味感觉的能力。
本发明可以其他形式来实现或以不离开本发明的精神或主要的特性的其他方法来实行。因此,现在所公开的内容应被认为是全面地说明性的而不是限制性的,本发明的范围已在附上的权利要求书中指出。在处于相等的范围和含义之内的所有改变都已被认为包含于其中。
Claims (22)
1、一种用于向食物组合物提供增强香味或甜味的流动性细粒释放体系,该释放体系包括:
(a)一种含有细粒状香料的核心;和
(b)一种用于上述核心的包封基质,该基质包括含有一种强甜味剂的亲水聚合物的外包覆层,该外包覆层由亲水聚合物和上述强甜味剂的溶液制成,上述强甜味剂于聚合物溶液中的存在量范围按上述溶液重量计为从约0.1%至约50%,外包覆层的存在量按上述核心重量计为约2%至约100%;
(c)其中包封基质保护了在核心中的香料并让在核心中的高浓度香味被包含在内而不将苦味赋予所得到的香味释放体系,并促进香味始终如一的释放。
2、根据权利要求1的释放体系,其中的核心是一种喷洒干燥的天然或人造香料或精油。
3、根据权利要求2的释放体系,其中喷洒干燥的香料是从由留兰香香料、胡椒薄荷香料、肉桂香料、果香香料、果香精油、可乐果香料、可乐果萃取物和它们的混合物组成的香料组中选出。
4、根据权利要求1的释放体系,其中香料组合物的存在量按核心重量计为约5%至约90%。
5、根据权利要求1的释放体系,其中香料组合物的存在量按核心重量计为约20%至约30%。
6、根据权利要求1的释放体系,其中所说的外包覆层是从由水解胶体、多糖类、多元醇和它们的混合物组成的组中选出。
7、根据权利要求6的释放体系,其中所说的外包覆层是从由树胶类、果胶类、藻酸盐类、粘质类、成膜碳水化合物类、和它们的混合物组成的组中选出。
8、根据权利要求6的释放体系,其中所说的外包覆层是从由阿拉伯胶、黄蓍胶、刺梧酮胶、茄替胶、琼脂、藻酸盐类、角义菜胶、fucellun、欧车前胶、和它们的混合物组成组中选出。
9、根据权利要求6的释放体系,其中所说的外包覆层是从由聚乙烯吡咯烷酮、白明胶、聚葡糖、xanthin、curdan、纤维素、甲基纤维素、乙基纤维素、羟乙基纤维素、羟丙基纤纤素、羟丙基甲基纤维素、羧甲基纤维素、低甲氧基果胶、丙二醇藻酸酯和它们的混合物组成的组中选出。
10、根据权利要求1的释放体系,其中所说的外包覆层的存在量按所说的核心重量计从约15%至约50%。
11、根据权利要求1的释放体系,其中甜味剂的存在量范围按外包覆层的重量计从约3%至约15%。
12、一种制备在调节香料释放同时能提供较多的前缘香料(up front flavor)供对香料的较大保护的香料释放体系的方法,该方法包括:
(a)形成含有一种香料的细粒核心;
(b)通过一种流化床型的方法用一种包封基质包覆所得到的细粒核心,所说的包封基质包括一种含有强甜味剂的亲水聚合物的外包覆层,所说的外包覆层是由亲水聚合物和所说的强甜味剂的溶液制备成,所说的强甜味剂在聚合物溶液中的存在量范围按所说的核心重量计从约0.1%至约50%,外包覆层的存在量从约2%至约100%;和
(c)回收复合包覆的颗粒成品;
(d)其中包封基质保护了在核心中的香料并让高浓度的香料包含于其中而不将苦味赋予所得到的香料释放体系,并促进始终如一的香味释放。
13、一种制备具有改进的香味强度并保持香料释放性质的口香糖组合物的方法,该方法包括:
(1)应用权利要求12的方法制备一种香料释放体系;
(2)将在第一步中制备的香料释放体系加到一种树胶基料和其余的口香料成份所形成的均匀混合物中;以及
(3)使所得到的混合物形成适当的口香糖形状。
14、根据权利要求1的释放体系混合到一种口香糖组合物中。
15、根据权利要求1的释放体系混合到一种糖果组合物中。
16、根据权利要求1的释放体系混合到一种药物组合物中。
17、根据权利要求1的释放体系混合到一种食物产品中。
18、根据权利要求1的释放体系混合到一种洁牙剂组合物或托牙粘合剂中。
19、一种包含权利要求1的释放体系的硬糖果。
20、一种包含权利要求1的释放体系的口腔卫生制剂。
21、一种包含权利要求1的释放体系的口腔药物制剂。
22、一种包含权利要求1的甜味剂释放体系的面包产品。
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CN115460932A (zh) * | 2020-04-30 | 2022-12-09 | 弗门尼舍有限公司 | 风味剂颗粒、其制备方法以及稳定风味剂的用途 |
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CN114307887B (zh) * | 2021-06-10 | 2023-03-10 | 广州昆特臣香精香料科技有限公司 | 一种油性香精微胶囊的制备方法及其微胶囊 |
Also Published As
Publication number | Publication date |
---|---|
KR910016275A (ko) | 1991-11-05 |
NO911260D0 (no) | 1991-03-27 |
IE911064A1 (en) | 1991-10-09 |
DE69106764T2 (de) | 1995-05-18 |
JPH04222558A (ja) | 1992-08-12 |
US5004595A (en) | 1991-04-02 |
GR3015813T3 (en) | 1995-07-31 |
ZA912407B (en) | 1992-11-25 |
ES2067195T3 (es) | 1995-03-16 |
PH27497A (en) | 1993-07-23 |
PT97155A (pt) | 1991-11-29 |
EP0453397A1 (en) | 1991-10-23 |
CA2039247C (en) | 1997-05-13 |
AU7401191A (en) | 1991-10-03 |
DK0453397T3 (da) | 1995-06-06 |
JP3031641B2 (ja) | 2000-04-10 |
NO911260L (no) | 1991-10-01 |
EP0453397B1 (en) | 1995-01-18 |
DE69106764D1 (de) | 1995-03-02 |
MX166660B (es) | 1993-01-26 |
CA2039247A1 (en) | 1991-10-01 |
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