CN1303670A - 粉末状稳定维他命和/或类胡萝卜素产品及其生产方法 - Google Patents
粉末状稳定维他命和/或类胡萝卜素产品及其生产方法 Download PDFInfo
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- CN1303670A CN1303670A CN00129016A CN00129016A CN1303670A CN 1303670 A CN1303670 A CN 1303670A CN 00129016 A CN00129016 A CN 00129016A CN 00129016 A CN00129016 A CN 00129016A CN 1303670 A CN1303670 A CN 1303670A
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- Prior art keywords
- vitamin
- dry powder
- water
- sugar
- composition
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- A—HUMAN NECESSITIES
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- 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
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Seasonings (AREA)
Abstract
本发明涉及一种生产不溶于热水、包含1种或多种脂溶性维他命和/或1种或多种类胡萝卜素的稳定干粉末的方法,包括下列加工步聚:A.制备一种水分散体,它包含:a1)2~50wt%至少1种蛋白质,a2)1~30wt%至少1种糖,a3)0.2~20wt%至少1种无机盐,a4)0.1~20wt%至少1种脂溶性维他命和/或至少1种类胡萝卜素,a5)5~95wt%水,其中所有重量百分率数值均以水分散体总重量为基准,各个成分a1)~a5)的百分数之总和等于100%,B.将该分散体转化为干粉末,以及C.将干粉末加热到55℃~180℃的温度,其中以碱金属磷酸盐作为无机盐a3),以便使蛋白质交联到当粉末被引入100℃水中以后至少3min内保持不溶于水的程度。
Description
本发明涉及粉末状稳定维他命和/或类胡萝卜素产品及其生产方法。
粉末状维他命和类胡萝卜素产品为众所周知并大规模用于医药工业以及动物饲料和人类食品工业。因此,有多种生产适当产品的方法描述于文献中。
通常,将脂溶性维他命和/或类胡萝卜素分散在有机成膜胶体的水溶液中,并将获得的分散体最后转化为粉末状干产品。
在先有技术中,通常用明胶作为成膜胶体。
此类产品当准备用作人类食品或动物饲料的添加剂时,其稳定性必须符合特别高的要求,因为在这些用途中它们将受到各种各样的严酷作用,例如高温、潮湿、机械摩擦或压力,这些作用对敏感的维他命和类胡萝卜素都是极其有害的。因此,曾进行过不少尝试以期开发提供热和机械稳定性特别高的稳定产品的方法。
譬如,GB993138公开了含明胶维他命产品的稳定化方法,其中原料颗粒以明胶-变性剂如甲醛、乙二醛、乙醛或二羟基丙酮进行处理,随后进行加热,或者仅进行热处理。
EP-B-0285682公开了一种生产含脂溶性维他命的球形颗粒产品的方法,包括用水、明胶和糖制成乳液,将乳液转化为液滴,以特定方式将液滴收集在淀粉粉末组合物中从而使诸液滴在永久性地成形为较好形状之前保持彼此分开,所形成的颗粒从多余淀粉粉末中分离出来,然后以90~180℃的温度进行热处理。
另外,EP-A-0494417描述了明胶在还原性糖和羧酸或无机酸水溶性盐存在下在55~180℃的温度进行交联的方法。
然而,以上所述方法存在的缺点是,要求过长的交联时间或过高交联温度,以致可能破坏产品中热不稳定的脂溶性维他命或类胡萝卜素。
本发明的目的是提供不具有上述缺点的生产粉末状、稳定维他命和/或类胡萝卜素产品的方法。
我们发现,这一目的可由一种生产不溶于热水、包含1种或多种脂溶性维他命和/或1种或多种类胡萝卜素的稳定干粉末的方法实现,包括下列加工步骤:
A.制备一种水分散体,它包含:
a1)2~50wt%至少1种蛋白质,
a2)1~30wt%至少1种糖,
a3)0.2~20wt%至少1种无机盐,
a4)0.1~20wt%至少1种脂溶性维他命和/或至少1种类胡萝卜素,
a5)5~95wt%水,
其中所有重量百分率数据均以水分散体总重量为基准,各个成分a1)~a5)的百分数之和等于100%,
B.将该分散体转化为干粉末,以及
C.将干粉末加热到55℃~180℃的温度,
其中以碱金属磷酸盐作为无机盐a3),以便使蛋白质交联到当干粉末被引入100℃水中以后至少3min内保持不溶于水的程度。
在加工步骤(A)中,作为保护性胶体用于水分散体制备中的蛋白质a1),可取自植物源或动物源。尤其可举出的例子,当A和B类二者之一处于宽范围起霜(bloom)的状况时,为明胶,特别是骨胶、牛胶、鱼胶;以及果胶、酪蛋白或酪蛋白酸盐、大豆蛋白以及玉米蛋白。优选使用的明胶具有50~300,尤其优选80~150的起霜值。保护性胶体的一般用量介于约2~50wt%,优选3~25wt%,尤其优选5~15wt%,以水分散体总重量为基准。
作为成分a2),可以使用任何还原性糖或含还原性糖的糖浆。还原性糖包括果糖、葡萄糖、乳糖、麦芽糖、木糖、阿糖、核糖及蔗糖,以及蜂蜜和果糖及葡萄糖的糖浆。
用于本发明目的的糖优选是果糖、葡萄糖及蔗糖以及它们的混合物。葡萄糖和/或果糖是尤其优选的糖。这些糖的一般用量介于约1~30wt%,优选2~20wt%,尤其优选3~15wt%,以水分散体的总重量为基准。
成分a4)的脂溶性维他命包括维他命A、E、D和K,包括它们的衍生物,例如维他命A的酯,如维他命A乙酸酯、维他命A丙酸酯或维他命A棕榈酸酯,以及维他命E的酯,如乙酸生育酚酯。为达到本发明的目的,它们可以维他命油溶液的形式使用,如作为维他命原,以及作为天然或合成来源的纯维他命使用。维他命A及其衍生物是尤其有用的,尤其优选维他命A乙酸酯、维他命A丙酸酯以及维他命A棕榈酸酯乃至它们的混合物,最优选维他命A乙酸酯。
类胡萝卜素应理解为诸如下列的化合物:β-胡萝卜素、lycopine(番茄红素)、bixine(胭脂树素)、玉米黄质、citranaxanthine、角黄素、虾青素、黄体素、辣椒红、隐黄质、β-脱辅基(apo)-8’-胡萝卜酸及其酯、β-脱辅基-8’-胡萝卜醛、β-脱辅基-12’-胡萝卜醛以及它们的混合物。优选的类胡萝卜素是β-胡萝卜素、番茄红素、黄体素、玉米黄质、角黄素以及虾青素。
维他命和/或类胡萝卜素的含量一般介于0.1~20wt%,优选1~15wt%,尤其优选2~12wt%,以可由加工步骤(A)获得的水分散体总重量为基准。
按照本发明,为制备上述水分散体,使用至少1种碱金属磷酸盐作为无机盐a3)。其可能的例子是钠、钾或锂的单-、二-或三-磷酸盐以及多磷酸盐。
优选的碱金属磷酸盐是三代磷酸钠、磷酸二氢钠、磷酸氢二钠、二磷酸二氢二钠、三磷酸五钠、三甲磷酸钠[sic]、三代磷酸钾、磷酸二氢钾、磷酸氢二钾、二磷酸氢二钾、三磷酸五钾、三甲磷酸钾[sic]。三代磷酸钠、磷酸二氢钠、磷酸氢二钠、三代磷酸钾、磷酸二氢钾以及磷酸氢二钾是尤其优选的。磷酸氢二钠是最优选的。
碱金属磷酸盐的含量一般介于0.2~20wt%,优选0.3~15wt%,尤其优选0.4~10wt%,最优选0.5~5wt%,以可由加工步骤(A)获得的水分散体总重量为基准。
除了上述成分之外,可以并有利的是,在分散体中再加入其他生产活性物质干粉末惯用的助剂和添加剂。
用此种干粉末作为动物饲料添加剂,而此时其活性物质又对氧化敏感时,尤其重要的是要加入抗氧剂,如ethoxyquin、丁基化羟基甲苯(BHT)、丁基化羟基茴香醚(BHA)或者,合适的话,生育酚,以及诸如柠檬酸或肌醇六磷酸及其碱金属或碱土金属盐之类的稳定剂,或者诸如乙二胺四乙酸(EDTA)或次氮基三乙酸(NTA)之类的络合剂。
然而,诸如甘油、山梨醇或聚乙二醇之类的润湿剂或者另外的乳化剂如卵磷脂,也常常被加入到乳液中。
再有,诸如淀粉,特别是玉米淀粉或麦芽糊精,以及增稠剂如阿拉伯树胶、瓜耳胶、藻酸盐以及某些降解淀粉等的添加,也证明对调节乳液的粘度是有益的。
还发现,在加工步骤(A)的水分散体中,作为附加的化合物a6)加入0.5~20wt%,优选1~10wt%淀粉,特别是玉米淀粉,是有利的。
有关所述配位体的进一步细节、此类添加物的性质和用量,可参见相应的专著,例如上面提到的专著《脂溶性维他命》,卷9,特别是128~133页。
本发明的一种具体实施方案包括在步骤(A)中使用
a1)5~15wt%明胶,起霜值介于50~300,
a2)3~15wt%至少1种糖,选自果糖和葡萄糖,
a3)0.5~5wt%磷酸氢二钠,
a4)2~12wt%至少1种脂溶性维他命,选自维他命A、维他命A乙酸酯、维他命E和维他命E乙酸酯,
a5)30~85wt%水,以及
a6)1~10wt%淀粉。
为在加工步骤(A)中制备分散体,本发明方法的一般程序是,将至少1种蛋白质a1)溶解在50~70℃温度的热水中,向该溶液中加入糖a2)、碱金属磷酸盐a3)、脂溶性维他命和/或类胡萝卜素、稳定剂以及其他传统添加剂每类当中的至少1种,以及合适的话,附加的水,然后通过在高温下剧烈搅拌使混合物分散。为使粉末热交联,这将在最后的加工步骤(C)中进行,制成分散体的pH应介于4~10,优选5~8的范围,其pH值可依据情况恰当选择地加入诸如氢氧化钠、氢氧化钾、氢氧化钙、氧化镁、碳酸钠或氢氧化铵之类的碱来调节。
将分散体进一步制成本发明的粉末的后续加工步骤可按照从文献中已知的方法实施。
由于对粉末所需粒度分布有一定要求(0.1~0.6mm直径),优选的方法是,在实施中小心控制分散体的胶凝液滴,使液滴在其形状变得稳定化之前保持彼此分开的状态。
例如可举出EP-B-74050所公开的方法,其中分散体被喷雾到疏水二氧化硅或高级脂肪酸金属盐当中,或者EP-B-285682公开的方法,其中分散体喷雾到淀粉粉末中。已发现,此种喷雾以采用疏水二氧化硅作为隔离剂来实施尤其有利。
按上述方法生产的粉末,在干燥(加工步骤B)之后,含水量介于5~15wt%,优选5~10wt%。如此获得的粉末状产品由表面成形良好的颗粒组成。它们能迅速溶解在约40℃的温水中,形成乳状分散体。
干燥后的粉末在加工步骤(C)中进行热固化,包括在55~180℃的温度进行加热,其中可能发生的交联过程的速度随温度的升高而增加。交联优选在70~130℃,尤其优选85~125℃的温度进行,反应时间介于5min~3h,优选6~25min。
如此生产的粉末,含水量介于0.1~4wt%,优选0.5~3.5wt%,尤其优选1~3wt%,能够在引入到沸水中以后至少3min内维持不溶于水,并具有极佳贮存稳定性(这方面可参见实例2和表2)以及诸如挤塑和造粒等实际应用过程中的极佳稳定性。
与先有技术的已知交联方法相比,本发明采用碱金属磷酸盐作为交联助剂的优点在于,交联时间缩短(这一点可参见表1)并且加工过程对产品比较温和。与采用EP-A-0494417所描述的采用乙酸钠相比,虽然采用后者可达到相近的交联时间,但是本发明生产的干粉末的贮存稳定性要好得多。因此可避免在乙酸钠的情况下由于例如乙酸的释放导致交联反应期间和贮存期间讨厌异味的产生。
本发明还涉及按照文章开头所描述的方法生产的不溶于热水的稳定干粉末,它包含:
a1)10~70wt%至少1种蛋白质,
a2)5~30wt%至少1种糖,
a3)0.5~25wt%至少1种碱金属磷酸盐,
a4)0.1~60wt%至少1种脂溶性维他命和/或至少1种类胡萝卜素,
a5)0.1~4wt%水,
其中所有重量百分率数值均以干粉末总重量为基准,各个成分a1)~a5)的百分数之和等于100%。
关于各个成分a1)~a5)的更准确定义——不论在一般的和优选的实施方案中——可参见文章开头的陈述。
除了成分a1)~a5)之外,本发明干粉末还可另外包含,作为成分a6),0.5~40wt%淀粉。
为实现本发明的目的,优选这样的干粉末,它包含:
a1)10~70wt%明胶,起霜值介于50~300,被交联到,引入到100℃水中以后至少3min内不溶于水的程度,
a2)5~30wt%至少1种糖,选自果糖和葡萄糖,
a3)0.5~10wt%磷酸氢二钠,
a4)1~50wt%至少1种选自维他命A、维他命A酯、维他命E和维他命E酯的化合物,
a5)1~3wt%水。
本发明还涉及包含不溶于热水的上述稳定干粉末的人类食品及动物饲料。所谓动物饲料是指任何与此相关类型的维他命预混物、预混物、无机饲料以及配混饲料。
本发明的主题在下面的实施例中将得到更详细的阐明。
实例1
维他命A干粉末的制备
34.1g(30g固体)起霜值100的明胶A,加入到300g水中,溶胀30min后,通过在60℃加热而溶解。加入21.1g果糖糖浆(15g固体,糖含量70%,其中95%为果糖干物质),随后,相继加入22.7g玉米淀粉(20g固体)、3g磷酸氢二钠和25g维他命A乙酸酯(2.19MIU/g(百万国际单位每克),由维他命A乙酸酯2.9MIU/g以100mgethoxyquin和14.5mg BHT每MIU维他命A进行稳定化制成),此间混合物在60℃通过剧烈搅拌而乳化。制备的乳液在喷雾塔中、55℃下,采用单组分喷嘴、5.5~6.5bar压力喷雾到疏水二氧化硅的雾中。仍旧潮湿的产品在旋风干燥器中干燥到残余含湿5~6%并分离掉多余二氧化硅。然后,10g获得的粉末在浸泡于加热到110℃的油浴内的旋转铝烧瓶中进行热处理。在这样的条件下,交联点为10min。生产的褐色粉末含有维他命A540,000 IU/g,残余含湿2.9wt%。
替代地,10g未交联的粉末放在120℃条件下进行热处理。在这种条件下生成的褐色粉末仅经过7min(=交联点)之后便不再分散在沸水中(颗粒保持完整)了。
对比例
每种组成如表1所载的乳液在制备后,按照如实例1所述相同方式喷雾,从而生成粉末,并进行干燥。测定在110℃和85℃下进行热处理时的最短交联时间。
表1
乳液组成 | 加入的盐 | 含水量[%bywt] | 110℃最短交联时间[min] | 85℃最短交联时间[min] |
对比例 | ||||
a)如同实例1 | 3.1 | >30 | n.d. | |
b)如同实例1 | 乙酸钠 | 2.9 | 12 | 190 |
c)如同实例1 | CaHPO4 | 2.1 | 22 | 250 |
d)如同实例1 | Ca(H2PO4)2 | 2.3 | 30 | 330 |
e)如同实例1 | CaSO4 | 2.0 | 27 | 260 |
f)如同实例1 | 乙酸钙 | 2.4 | 11 | 115 |
本发明: | ||||
实例1 | Na2HPO4 | 2.9 | 10 | 90 |
如同实例1 | K2HPO4 | 2.8 | 12 | 100 |
实例2
在每种情况中,从如同实例1和对比例a)所制备的干粉末中筛选出粒度250~355μm的级分,并置于标准预混物中进行稳定性试验。为此,约100mg试样称重到样品试管中(每种样品和试验时间称取4份样品),与4g预混物混合,预混物由60%麦糠、30%50%胆碱盐酸盐加载在二氧化硅上,以及10%痕量元素混合物组成,元素混合物包括:37.43%硫酸铜×5H2O;46.78%硫酸亚铁×7H2O;11.79%氧化锌;3.61%MnO和0.39%COCO3,随后用手小心地混合。
各种样品放在恒温恒湿(40℃和70%相对湿度)人工气候室内的敞口容器中贮存6周。在开始贮存和6周以后,取出4个为特定试验时间所准备的试样并检验剩余维他命A活性物质含量。
试验结果载于表2中:
表2
维他命A干粉末贮存稳定性调查
干粉末 | t=0[I.u./g]*) | t=6周**) |
1.实施例1中的 | 540,000=100% | 80.5% |
2.对比例a)中的 | 520,900=100% | 60.4% |
*)稳定性试验开始时干粉末中维他命A浓度。
**)贮存6周以后干粉末中维他命A浓度。含量是采用紫外光谱术测定的。这些数字指出相对于起始浓度的维他命A含量。
Claims (14)
1.一种生产不溶于热水、包含1种或多种脂溶性维他命和/或1种或多种类胡萝卜素的稳定干粉末的方法,包括下列加工步骤:
A.制备一种水分散体,它包含:
a1)2~50wt%至少1种蛋白质,
a2)1~30wt%至少1种糖,
a3)0.2~20wt%至少1种无机盐,
a4)0.1~20wt%至少1种脂溶性维他命和/或至少1种类胡萝卜素,
a5)5~95wt%水,
其中所有重量百分率数值均以水分散体总重量为基准,各个成分a1)~a5)的百分数之和等于100%,
B.将该分散体转化为干粉末,以及
C.将干粉末加热到55℃~180℃的温度,
其中以碱金属磷酸盐作为无机盐a3),以便使蛋白质交联到当干粉末被引入100℃水中以后至少3min内保持不溶于水的程度。
2.权利要求1的方法,其中蛋白质a1)是至少1种选自明胶、果胶、酪蛋白和酪蛋白酸盐的化合物。
3.权利要求1或2的方法,其中用至少1种选自果糖、葡萄糖和蔗糖的糖作为成分a2)。
4.权利要求1~3中任何一项的方法,其中用至少1种选自维他命A、维他命A酯、维他命E和维他命E酯的化合物作为成分a4)。
5.权利要求1~4中任何一项的方法,其中加工步骤A中的水分散体包含,作为附加成分a6)的0.5~20wt%淀粉。
6.权利要求1~5中任何一项的方法,其中在加工步骤A中使用
a1)5~15wt%明胶,起霜值介于50~300,
a2)3~15wt%至少1种糖,选自果糖和葡萄糖,
a3)0.5~5wt%磷酸氢二钠,
a4)2~12wt%至少1种脂溶性维他命,它选自维他命A、维他命A乙酸酯、维他命E和维他命E乙酸酯,
a5)30~85wt%水,以及
a6)1~10wt%淀粉。
7.权利要求1~6中任何一项的方法,其中加工步骤B)的干粉末的含水量介于5~15wt%。
8.权利要求1~7中任何一项的方法,其中加工步骤C)的干粉末的含水量介于0.1~4wt%。
9.一种按照权利要求1所述方法的不溶于热水的稳定干粉末,它包含:
a1)10~70wt%至少1种蛋白质,
a2)5~30wt%至少1种糖,
a3)0.5~25wt%至少1种碱金属磷酸盐,
a4)0.1~60wt%至少1种脂溶性维他命和/或至少1种类胡萝卜素,
a5)0.1~4wt%水,
其中所有重量百分率数值均以干粉末总重量为基准,各个成分a1)~a5)的百分数之和等于100%。
10.权利要求9的干粉末,它包含,作为蛋白质,至少1种选自明胶、果胶、酪蛋白和酪蛋白酸盐的化合物。
11.权利要求9或10的干粉末,它包含,作为成分a2),至少1种选自果糖、葡萄糖和蔗糖的糖。
12.权利要求9~11中任何一项的干粉末,它另外包含,作为成分a6),0.5~40wt%淀粉。
13.权利要求9~12中任何一项的干粉末,它包含
a1)10~70wt%明胶,起霜值介于50~300,被交联到当引入100℃水中以后至少3min内不溶于水的程度,
a2)5~30wt%至少1种糖,选自果糖和葡萄糖,
a3)0.5~10wt%磷酸氢二钠,
a4)1~50wt%至少1种选自维他命A、维他命A酯、维他命E和维他命E酯的化合物,以及
a5)1~3wt%水。
14.一种包含权利要求9~13中任何一项的干粉末的人类食品或动物饲料。
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US (1) | US6328995B1 (zh) |
EP (1) | EP1088486B1 (zh) |
JP (1) | JP4571736B2 (zh) |
CN (1) | CN1149981C (zh) |
AT (1) | ATE319329T1 (zh) |
DE (1) | DE50012343D1 (zh) |
DK (1) | DK1088486T3 (zh) |
ES (1) | ES2259587T3 (zh) |
Cited By (1)
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CN102647980A (zh) * | 2009-12-09 | 2012-08-22 | 安迪苏法国联合股份有限公司 | 稳定的脂溶性活性成分颗粒 |
Families Citing this family (24)
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ATE291856T1 (de) * | 2001-08-23 | 2005-04-15 | Dsm Ip Assets Bv | Neuartige, stabilisierte carotenoid-mischungen |
US6974592B2 (en) * | 2002-04-11 | 2005-12-13 | Ocean Nutrition Canada Limited | Encapsulated agglomeration of microcapsules and method for the preparation thereof |
AR040588A1 (es) | 2002-07-26 | 2005-04-13 | Schering Corp | Formulacion farmaceutica que comprende un inhibidor de la absorcion del colesterol y un inhibidor de una hmg- co a reductasa |
AU2003301654A1 (en) * | 2002-10-22 | 2004-05-13 | Dainippon Pharmaceutical Co., Ltd. | Stabilized composition |
ES2347045T3 (es) * | 2002-11-04 | 2010-10-25 | Ocean Nutrition Canada Limited | Microcapsulas que tienen multiples cortezas, y metodo para su preparacion. |
KR20050088175A (ko) * | 2002-12-17 | 2005-09-02 | 메드이뮨 백신즈 인코포레이티드 | 생물활성 물질의 고압 분무 건조 |
EP1433387A1 (en) * | 2002-12-26 | 2004-06-30 | Adisseo France S.A.S. | Solid granules containing carotenoids |
EP1587375B1 (en) * | 2003-01-31 | 2019-03-27 | DSM IP Assets B.V. | Novel compositions comprising carotenoids |
WO2004084862A1 (en) * | 2003-03-27 | 2004-10-07 | Dsm Ip Assets B.V. | Process for the production of cross-linked gelatin beadlets |
JP4716982B2 (ja) * | 2003-04-03 | 2011-07-06 | ディーエスエム アイピー アセッツ ビー.ブイ. | 脂溶性活性成分の粉末状配合物 |
CN100502673C (zh) * | 2003-07-15 | 2009-06-24 | 帝斯曼知识产权资产管理有限公司 | 脂溶性活性成分的粉末状制剂 |
US8034450B2 (en) * | 2005-01-21 | 2011-10-11 | Ocean Nutrition Canada Limited | Microcapsules and emulsions containing low bloom gelatin and methods of making and using thereof |
DE602006011127D1 (de) * | 2005-01-27 | 2010-01-28 | Ocean Nutrition Canada Ltd | Fettsäure-benzenediol-derivate sowie herstellungs- und verwendungsverfahren dafür |
CA2556520C (en) * | 2005-01-27 | 2008-10-28 | Ocean Nutrition Canada Ltd. | Chromium-fatty acid compounds and methods of making and using thereof |
US9968120B2 (en) | 2006-05-17 | 2018-05-15 | Dsm Nutritional Products Ag | Homogenized formulations containing microcapsules and methods of making and using thereof |
EP2436273A1 (en) * | 2006-04-07 | 2012-04-04 | Ocean Nutrition Canada Limited | Emulsions and microcapsules with substances having low interfacial tension, methods of making and using thereof |
US9056058B2 (en) * | 2006-06-05 | 2015-06-16 | Dsm Nutritional Products | Microcapsules with improved shells |
US7435846B2 (en) * | 2006-08-18 | 2008-10-14 | Industrial Organica, S.A. De C.V. | Absorption and bioavailability of carotenoids, formulations and applications |
ES2604081T3 (es) | 2007-01-10 | 2017-03-02 | Dsm Nutritional Products Ag | Microcápsulas que incluyen proteína de guisante |
CA2691883A1 (en) | 2007-07-06 | 2009-01-15 | Basf Se | Method for the production of an aqueous glucose solution |
JP4781328B2 (ja) * | 2007-08-21 | 2011-09-28 | 新田ゼラチン株式会社 | ゼリー用材料、その製造方法および用途 |
US20120157547A1 (en) | 2010-12-21 | 2012-06-21 | Ricardo Montoya-Olvera | Compositions and applications of carotenoids of improved absorption and bioavailability |
BR112013016679B1 (pt) * | 2010-12-27 | 2018-03-20 | Dsm Ip Assets B.V. | Formulação pulverulenta, uso da formulação e alimentos, rações ou produtos de higiene pessoal compreendendo a formulação |
US20190090529A1 (en) * | 2016-03-02 | 2019-03-28 | Basf Se | Vibration droplet formation |
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US4294856A (en) * | 1977-01-04 | 1981-10-13 | Tokai Regional Fisheries Research Laboratory | Process for manufacture of artificial milk replacer for raising infant pigs and other infant animals |
DE2822324C3 (de) * | 1978-05-22 | 1981-02-26 | Basf Ag, 6700 Ludwigshafen | Herstellung von Vitamin-E-Trockenpulver |
JP2546838B2 (ja) * | 1986-03-24 | 1996-10-23 | エフ・ホフマン―ラ ロシユ アーゲー | ビタミン製剤の製造方法 |
JPS6418439A (en) * | 1987-07-14 | 1989-01-23 | Nippon Oils & Fats Co Ltd | Powdery fat coated with crosslinked coating and its manufacture |
IL88961A (en) * | 1988-01-29 | 1992-07-15 | Basf Ag | Stable mixtures containing oxidation-sensitive compounds |
US5126328A (en) * | 1991-01-10 | 1992-06-30 | Bower David K | Process for crosslinking gelatin |
US5153177A (en) * | 1991-01-10 | 1992-10-06 | Basf Corporation | Process for incorporating a material in a crosslinked gelatin, and product therefrom |
EP0494417B1 (en) * | 1991-01-10 | 1996-04-17 | Basf Corporation | Process for crosslinking gelatin and for incorporation a material therein |
DE4141351A1 (de) * | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
KR950701191A (ko) * | 1992-04-23 | 1995-03-23 | 알렌 제이. 스피겔 | 이온화 가능한 유화제와 이온화가능한 폴리펩티드 및/또는 이온화 가능한 하이드로콜로이드와의 이온성 착체(ionic complexes of lonizable emulsifiers with ionizable polypeptides and/or ionizable hydrocolloids) |
-
1999
- 1999-09-24 US US09/404,600 patent/US6328995B1/en not_active Expired - Lifetime
-
2000
- 2000-08-25 AT AT00118467T patent/ATE319329T1/de not_active IP Right Cessation
- 2000-08-25 DK DK00118467T patent/DK1088486T3/da active
- 2000-08-25 DE DE50012343T patent/DE50012343D1/de not_active Expired - Lifetime
- 2000-08-25 ES ES00118467T patent/ES2259587T3/es not_active Expired - Lifetime
- 2000-08-25 EP EP00118467A patent/EP1088486B1/de not_active Expired - Lifetime
- 2000-09-21 JP JP2000287612A patent/JP4571736B2/ja not_active Expired - Lifetime
- 2000-09-25 CN CNB001290169A patent/CN1149981C/zh not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102647980A (zh) * | 2009-12-09 | 2012-08-22 | 安迪苏法国联合股份有限公司 | 稳定的脂溶性活性成分颗粒 |
CN106173280A (zh) * | 2009-12-09 | 2016-12-07 | 安迪苏法国联合股份有限公司 | 稳定的脂溶性活性成分颗粒 |
Also Published As
Publication number | Publication date |
---|---|
CN1149981C (zh) | 2004-05-19 |
DK1088486T3 (da) | 2006-05-29 |
EP1088486A2 (de) | 2001-04-04 |
EP1088486A3 (de) | 2002-09-11 |
JP4571736B2 (ja) | 2010-10-27 |
JP2001149042A (ja) | 2001-06-05 |
ES2259587T3 (es) | 2006-10-16 |
EP1088486B1 (de) | 2006-03-08 |
DE50012343D1 (de) | 2006-05-04 |
ATE319329T1 (de) | 2006-03-15 |
US6328995B1 (en) | 2001-12-11 |
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