CN1364426A - 水溶性、少量水溶性或水不溶性活性化合物固体制品的生产 - Google Patents
水溶性、少量水溶性或水不溶性活性化合物固体制品的生产 Download PDFInfo
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- CN1364426A CN1364426A CN01130192A CN01130192A CN1364426A CN 1364426 A CN1364426 A CN 1364426A CN 01130192 A CN01130192 A CN 01130192A CN 01130192 A CN01130192 A CN 01130192A CN 1364426 A CN1364426 A CN 1364426A
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Abstract
本发明描述了一种生产至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品的方法,该制品适用于食品和动物饲料成分或者适用于药品和化妆品。此外,本发明涉及油性悬浮液,其中这些制品以分散相存在,本发明还涉及这些制品作为动物饲料、食品、药品和化妆品的添加剂的用途。
Description
技术领域
本发明涉及一种适用于食品和动物饲料成分或者适用于药品和化妆品的至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品的生产方法。此外本发明涉及含有这些制品的油性悬浮液及其作为动物饲料、食品、药品和化妆品的添加剂的用途。
背景技术
适用于食品和动物饲料成分或者适用于药品和化妆品的大量活性化合物,例如脂溶性维生素、类胡萝卜素,以及天然颜料姜黄色素和胭脂红,由于它们不溶于水并且对氧化敏感,因此它们仅能以特别稳定的制品形式使用。这些结晶物料,尤其是用于染色含水食品,通常不能直接用作饲料添加剂或者作为化妆品中的活性化合物。在生物利用度、着色性能和分散性,特别是在水性介质以及亲油介质中,这些方面的高要求使其仅能通过特定制剂满足。
在直接着色食品的情况下,只有借助于以细分散形式存在以及如果适宜的话,通过保护性胶体防止活性化合物(例如类胡萝卜素)氧化的制品,才可以获得令人满意的着色产品。这些用于动物饲料的制品使得活性化合物的生物利用度升高,并且因此间接地提高了着色效果,例如在蛋黄着色或鱼着色时。
从文献中已知大量差异非常大的制备方法,所有这些方法都具有降低活性化合物的结晶尺寸的目的,并使其细度低于10μm。
许多方法,尤其在Chimia 21 329(1967)、WO 91/06292和WO 94/19411中所述的,使用胶体磨粉碎类胡萝卜素,由此获得2-10μm的细度。
此外,例如在DE-A-1211911或EP-A-0410236中描述了乳化/喷雾干燥的组合方法。
按照欧洲专利EP-B-0065193,通过例如在50-200℃的温度下,可以在高压下,在低于10秒钟的时间内将β-胡萝卜素溶于挥发性可水混的有机溶剂中制备细分散的粉状类胡萝卜素制品。在0-50℃下通过立即快速地与保护性胶体水溶液混合将β-胡萝卜素从所得的分子分散体中沉淀出。这样来生产一种橙黄色胶体分散的β-胡萝卜素水溶胶。接着将该分散体喷雾干燥,生产出自由流动的干粉,将该干粉溶于水可形成一种澄清的橙黄色分散体。
在EP-A-0937412中描述了一种使用非水混的溶剂生产细分散粉状类胡萝卜素制品的类似方法。
WO98/26008涉及将低分子量和高分子量保护性胶体用于生产可再分散的含叶黄素干粉的用途。
类胡萝卜素越来越多地以液体制品形式作为动物营养的饲料添加剂。尤其是其优点可以简化计量并且更准确。此外,直到其用饲料添加剂的液体制剂生产之后,在称之为后造粒应用中可以不加入饲料颗粒。这意味着可以使用甚至是氧化敏感性的和热敏性添加剂如类胡萝卜素,而且没有相当大的损失。
后造粒应用(PPA)的例子尤其可以在GB-A-2232573和EP-A-0556883中找到,将这些文献引入本文作为参考。
WO96/23420描述了细度小于2μm的结晶虾青素的油性悬浮液。这类悬浮液尤其是通过在油中将这些虾青素晶体粉碎生产的。此外,该公开物包括了挤出之后负载挤出饲料的悬浮液的用途。然而,其中这些悬浮液的稳定性和存在其中的虾青素的生物利用度对许多应用来说有时是不够的。
类胡萝卜素乳液,作为液体制剂的特定形式,经常具有如下缺点:它们在物理(发生相分离)和化学(发生不需要的水解和/或氧化还原反应,单独溶解的组分的化学不相容性)方面不稳定,此外,经常发生微生物污染的危险。
在其它方法中,例如WO94/19411中所述,在有保护性胶体水溶液存在的情况下将结晶β-胡萝卜素粉碎,然后通过短时间加热到其熔点将其转变成非晶形改性。
在有稳定的保护性胶体存在的情况下,该制品和大量描述过的含水类胡萝卜素分散体和含有该活性化合物的O/W乳液,由于它们与油不能混溶,因此也不适合。
EP-A-0845503描述了液态可油混的类胡萝卜素制品,它作为双重分散体系,包含粒径小于100μm的含水分散相,其中保护性胶体稳定的一种或多种类胡萝卜素颗粒以分散体形式存在于作为分散介质的油中。
发明内容
本发明的目的在于提出一种生产水溶性、少量水溶性或水不溶性的活性化合物固体制品的方法。此外,可以获得具有高活性化合物浓度的制品。
本发明的目的还在于提供尤其适用于动物营养成分中用于提供饲料颗粒的液态油混性类胡萝卜素制品。
我们已发现,按照本发明该目的可以通过一种生产至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品的如下方法达到,该制品适用于食品和动物饲料成分或者用于药品和化妆品:
a)将上述活性化合物中的至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将该蛋白质保护性胶体与活性化合物一起从该分散体中絮凝出来和
c)将絮凝固体从水和另外使用的任意溶剂中分离,接着将它们转变成干粉。
适用于本发明目的的用于食品和动物营养成分或药品和化妆品的活性化合物例如为以下化合物:
脂溶性维生素,例如K维生素、维生素A及其衍生物如维生素A乙酸酯、维生素A丙酸酯或维生素A棕榈酸酯、维生素D2和维生素D3,以及维生素E及其衍生物。本文中的维生素E是天然或合成的α-、β-、γ-或δ-生育酚,优选天然或合成的α-生育酚以及生育三烯酚。维生素E及其衍生物例如是生育酚-C1-C20-羧酸酯,例如生育酚乙酸酯或生育酚棕榈酸酯。
水溶性维生素,例如抗坏血酸及其盐如抗坏血酸钠和维生素C衍生物如抗坏血酸-2-一磷酸钠、钙或镁或抗坏血酸-2-聚磷酸钙、泛酸钙、羟泛酸(Panthenol)、维生素B1(硫胺),如其盐酸盐、硝酸盐或焦磷酸盐,维生素B2(核黄素)及其磷酸盐,维生素B6及其盐、维生素B12、生物素、叶酸和叶酸衍生物如四氢叶酸、5-甲基四氢叶酸、5-甲酰四氢叶酸、烟酸和烟酰胺。
聚不饱和脂肪酸,例如亚油酸、亚麻酸、花生四烯酸、廿碳五烯酸、廿二碳六烯酸。
天然食品颜料,例如类胡萝卜素、姜黄色素、胭脂红或叶绿素。
水不溶性或少量水溶性紫外线过滤剂有机物,例如选自以下类别的化合物:三嗪类、酰基苯胺类、二苯酮类、三唑类、肉桂酰胺类和磺化苯并咪唑类。
其中取代基彼此独立,并且具有以下含义:R是H、卤素、OH、C1-C20-烷基、C1-C20-烷氧基、C1-C20-烷氧基烷基、C1-C20-羟基烷氧基、NR1R2或通式Ia的基团R1和R2
是H、C1-C20-烷基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基、C5-C8-环烷基;R3-R5
是H、OH、NR9R10、C1-C20-烷氧基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基、C5-C8-环烷基;R6-R8
是H、C1-C20-烷氧基、-C(=O)-R11、-C(=O)-X-R12、SO2R13、CN;R9-R11
是H、C1-C20-烷基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基、C5-C8-环烷基;R12是H、C1-C20-烷基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基、C5-C8-环烷基、或式为Sp-Sil的基团;R13是C1-C20-烷基、C5-C8-环烷基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基;X是O、NR14;R14是H、C1-C20-烷基、可以被一个或多个C1-C4-烷基取代的C6-C12-芳基、可以被一个或多个C1-C4-烷基取代的C7-C10-芳烷基、可以被一个或多个C1-C4-烷基取代的杂芳基、C5-C8-环烷基;Sp是间隔基团;Sil是来自由以下基团组成的基团:硅烷类、低聚硅氧烷和聚硅氧烷。
R、R1和R2、以及R9-R14中的烷基是支化或非支化的C1-C20-烷基链,优选甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、正庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、正壬基、正癸基、正十一烷基、1-甲基十一烷基、正十二烷基、1,1,3,3,5,5-六甲基己基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基或正二十烷基。
R为卤素时是氟、溴、碘,或者优选氯。
R和R3-R8为烷氧基是含有1-20个碳原子,优选1-12个碳原子,特别优选1-8个碳原子的直链和支链基团。
例如它们是:甲氧基 乙氧基异丙氧基 正丙氧基1-甲基丙氧基 正丁氧基正戊氧基 2-甲基丙氧基3-甲基丁氧基 1,1-二甲基丙氧基2,2-二甲基丙氧基 己氧基1-甲基-1-乙基丙氧基 庚氧基辛氧基 2-乙基己氧基
R为羟基烷氧基时是具有附加末端羟基官能团的上述烷氧基。
R1-R5和R9-R14是环烷基时优选为支链的或未支链化的C3-C10-环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基、1-甲基环丙基、1-乙基环丙基、1-丙基环丙基、1-丁基环丙基、1-戊基环丙基、1-甲基-1-丁基环丙基、1,2-二甲基环丙基、1-甲基-2-乙基环丙基、环辛基、环壬基或环癸基。优选C5-C8-环烷基,例如环戊基、环庚基、环辛基,尤其是环己基。
这些环烷基可以未取代的或者被一个或多个取代基,例如1-3个基团如卤素,例如氟、氯或溴、硝基、氨基、C1-C4-烷基氨基、C1-C4-二烷基氨基、羟基、C1-C4-烷基、C1-C4-烷氧基或其它基团取代的,或者在环中可以含有1-3个杂原子,例如硫、氮,它们的自由价可以被H或C1-C4-烷基、或者氧饱和。
C6-C12-芳基的例子尤其是苯基、萘基和联苯基。
C7-C10-芳烷基的例子是苯甲基、苯乙基、α-甲基苯乙基和α,α-二甲基苯甲基。
有利地,杂芳基是具有一个或多个杂芳族3-至7-元环的单一或稠合芳环体系。可以存在于该环或环体系的杂原子是一个或多个氮、硫和/或氧原子。
上述芳基、芳烷基和杂芳基的取代基是C1-C4-烷基,例如甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基和1,1-二甲基乙基。
术语间隔基团Sp在本文中意思是将硅烷、低聚硅氧烷或聚硅氧烷部分与三嗪基团连接起来的二价支化或未支化的C3-C12-亚烷基或-亚烯基链。
C3-C12-亚烷基链的例子是亚丙基、2-甲基亚丙基、亚丁基、亚戊基和亚己基。
C3-C12-亚烯基链的例子是2-丙烯-2-亚基(2-propen-2-ylene)、2-甲基-3-亚丙烯基(2-methyl-3-propenylene)、3-丁烯-3-亚基(3-buten-3-ylene)和4-戊烯-4-亚基(4-penten-4-ylene)。
优选的间隔基团是-(CH2)3-、-(CH2)4-、-(CH2)5-、-[CH(CH3)]-(CH2)-、-(CH)2-CH=CH-、-C(=CH2)-CH2-、-C(=CH2)-(CH2)2-O-(CH2)4-、-(CH2)4-O-(CH2)2-。
本文中的术语硅烷是基团SiR15R16R17,其中R15、R16、R17彼此独立地是C1-C6-烷基、C1-C6-烷氧基或苯基。
例子是:Si(CH2-CH3)3、Si(CH2-CH2-CH3)3、Si(异丙基)3、Si(叔丁基)3、Si(叔丁基)(CH3)2、Si(CH3)2-(己基)、Si(OCH3)3、Si(OEt)3、SiPh3。
术语低聚硅氧烷是选自以下通式的基团:SiR18 m(OSiR18 3)n,其中m=0、1或2;n=3、2或1,并且m+n=3;R18-[Si(R18)2-O-]r-Si(R18)2-A和R18-[Si(R18)2-O-]r-Si(A)(R18)-O-Si(R18)3,其中A是化学键或间隔基团,并且R18是C1-C6-烷基或苯基,以及r的值是1-9。
术语聚硅氧烷例如包括选自以下通式的基团:A-[Si(R19)2-O-]s-Si(R19)2-A或(R19)3-Si-[O-Si(R19)2]t-[O-Si(R19)-(A)]q-O-Si(R19)3,其中A是一化学键或一间隔基团,并且R19是C1-C6-烷基或苯基,s和t的值是4-250,并且q的值是1-30。
其中R12是式Sp-Sil基团的硅烷基三嗪类的例子可以在EP-A-0933376中找到。
其中R3-R5位于与该三嗪的苯氨基相邻的位置。
优选用作防晒的是干粉,该干粉含有至少一种通式Ib的1,3,5-三嗪衍生物,其中取代基彼此独立地具有以下含义:R3-R5
H、OH;R6-R8
C1-C12-烷氧基、-C(=O)-X-R12;X是O、NR14;R12和R14
是H、C4-C8-烷基。
UvinulT150以良好的UV吸收性能著称,并且具有特别高的消光系数,其在314nm下>1500。
来自三嗪类的其它少量水溶性或水不溶性有机UV滤过剂包括在WO94/05645和EP-A-0444323中所述的以下化合物:
特别优选的是N-(2-乙氧基苯基)-N’-(2-乙基苯基)乙二酰胺。
这组水不溶性三嗪的代表物还优选通式为IIIb和IIIc的化合物,其中T6和T7彼此独立地是C1-C18-烷基,优选叔丁基、-C(CH3)2-CH2-C(CH3)3或2-乙基己基。在这类通式为IIIa的特别优选的化合物中,基团T6和T7是-C(CH3)2-CH2-C(CH3)3。通式IIIc中的T8也是C1-C18-烷基,优选甲基。
优选的肉桂酰胺类是通式为IV的化合物,其中彼此独立地,Y1和Y2是H或C1-C4-烷基,优选甲基或乙基,并且Y3是芳基,优选苯基或4-甲氧基苯基。
优选的二苯酮类是通式VI的化合物,其中彼此独立地,M1-M4是H或C1-C4-烷基,M1和M4优选是甲基或乙基,并且M2和M3优选是H。
其它水溶性、少量水溶性或水不溶性活性化合物是矿物质、氨基酸、蛋白质或酶。
矿物质可以是例如,硫酸亚铁(iron Sulfate)、硫酸锌、硫酸锰、硫酸铜、硫酸钙、硫酸钠、氧化铜、氧化镁、氟化钙、氯化钾、碘化钾、氯化钠、碘酸钙、磷酸钙、磷酸镁、磷酸钾、磷酸钠或磷酸铁、碳酸钴、硒酸钠或硅酸及其盐。矿物质的使用量,例如在动物营养成分中,在每种情况下取决于喂食动物的需求。
氨基酸通常可以是所有已知的生理上可相容的α-氨基酸。优选丙氨酸、精氨酸、天冬酰胺、天冬氨酸、半胱氨酸、胱氨酸、谷酰胺、谷氨酸、甘氨酸、组氨酸、异亮氨酸、亮氨酸、赖氨酸、甲硫氨酸、苯丙氨酸、马尿酸、丝氨酸和牛磺酸。特别优选是赖氨酸、甲硫氨酸和半胱氨酸。
本文中的酶优选磷酸酶、葡聚糖酶,以及如果适宜的话优选酯酶或脂肪酶,后者为包封形式。
其它活性化合物可以是:
具有维生素或辅酶特性的化合物,例如氯化胆碱、肉碱、γ-丁内铵盐、硫辛酸、肌酸、泛醌、S-甲基甲硫氨酸、S-腺苷甲硫氨酸。
药用饲料的饲料抗生素和用于改善消化的微生物。
本文的水不溶性活性化合物是那些在20℃下水中的溶解度低于0.05%wt,优选低于0.01%wt的化合物。
少量水溶性活性化合物是那些在20℃下在水中的溶解度低于5%wt,优选低于1%wt,特别优选低于0.5%wt,尤其特别优选0.5-0.05%wt的化合物。
本文中的水溶性活性化合物是那些在20℃下水中的溶解度大于5%wt,优选大于10%wt,特别优选大于20%wt,尤其优选大于60%wt的化合物。
优选提供了一种生产至少一种少量水溶性或水不溶性活性化合物的固体制品的方法,所述制品适用于食品和动物饲料成分,或者适用于药品和化妆品,该方法是通过在步骤a)中,将上述少量水溶性或水不溶性的活性化合物中的至少一种分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中。
术语分散特别优选产生含水悬浮液和含水乳液。尤其优选分散步骤a)是在蛋白质保护性胶体的含水分子分散体或胶体分散体中产生至少一种的上述固体活性化合物悬浮液,其中分散相含有至少一种为纳米级粒子的活性化合物。
适用于本发明蛋白质保护性胶体不仅是水溶性的而且是水膨胀性的动物或植物源蛋白质。优选保护性胶体是酪蛋白、酪蛋白酸盐、牛明胶、猪明胶或鱼明胶,特别是Bloom数为0-250的酸或碱降解的明胶,例如明胶A 100、A 200、B 100和B 200和低分子量、和Bloom数为0且分子量为15,000-25,000 D的酶降解的明胶类,例如Collagel A和Gelitasol P(Stoess,Eberbach)和这些明胶的混合物。然而,在某些情况下,奶粉、全乳或脱脂乳适宜作为保护性胶体。植物蛋白质的典型代表是谷蛋白、玉米醇溶蛋白、大豆蛋白和豌豆蛋白。特别优选的保护性胶体是酪蛋白和酪蛋白酸盐。
就上述保护性胶体的更详细的内容,可参见R.A.Morton,Fat SolubleVitamins,Intern.Encyclopedia of Food and Nutrition,Vol.9,PergamonPress 1970,pp.128-131。
上述聚合物的水溶性或水膨胀性依赖于温度、pH和溶液的离子强度。
术语絮凝出的意思是在胶体体系中引起分散于该体系中的颗粒以片状沉积并由此引起溶胶/凝胶的转变。颗粒通常可以通过加入絮凝助剂、电解质、聚电解质、相反电荷的胶体或者通过加热并由此使蛋白质变性来絮凝出。在步骤b)中将蛋白质保护性胶体絮凝出的有益方法特征在于将该分散体的pH调整至用作保护性胶体蛋白质的等电点范围。按照本发明,该范围包括等电点上下的一个pH单位,优选0.5pH单位,特别优选0.1-0.2pH单位。尤其优选通过将分散体的pH调整至相应于用作保护性胶体的蛋白质的等电点的值来开始该絮凝。
絮凝出的固体以本身已知的方式,例如通过过滤或离心,从水和从任意附加使用的有机溶剂中分离出来。
可以将该材料转变成干粉,尤其是通过喷雾干燥、冷冻干燥或在流化床中干燥,也可以在有涂布材料的情况下。尤其适宜的涂布材料是玉米淀粉、硅酸和磷酸三钙。
分离的固体在冷冻干燥的过程中,可以加入低温防护剂,例如海藻糖或聚乙烯吡咯烷酮类。
上述方法的一个优选实施方式是,在絮凝之前将步骤a)中生产的悬浮液研磨。在这种情况下,在研磨之前优选将活性化合物以结晶形式悬浮。
可用本身已知的方式进行研磨,例如使用球磨机。根据所使用球磨机的类型,连续进行研磨,直到颗粒的平均细度D[4.3](它是由Fraunhofer衍射测定的)为0.1-100μm,优选0.2-50μm,特别优选0.5-30μm,尤其优选0.8-20μm,特别是1.0-10μm。术语D[4.3]是指容重的平均直径(参见handbook on theMalvern Mastersizer S,Malvern Instruments Ltd.,UK)。
关于研磨及其使用设备的其它细节尤其可以在如下文献中找到:Ullmann’sEncyclopedia of Industrial Chemistry,Sixth Edition,1999,ElectronicRelease,Size Reduction,Chapter 3.6.:Wet Grinding和EP-A-0498824。
也优选的本发明方法的变化形式是,阶段a)中的分散包括以下步骤:
a1)将一种或多种上述活性化合物溶于水混性有机溶剂或者水与水混性有机溶剂的混合物中,或者
a2)将一种或多种上述活性化合物溶于非水混的有机溶剂中,和
a3)将a1)或a2)获得的溶液与蛋白质保护性胶体的含水分子分散体或胶体分散体混合,活性化合物的疏水相以纳米分散相产生。
阶段a1)中所用的非水混的溶剂最初是水混性、热稳定的挥发性溶剂,其仅含有碳、氢和氧,例如醇类、醚类、酯类、酮类和缩醛类。方便地,使用那些至少10%可水混、沸点低于200℃和/或少于10个碳的溶剂。特别优选使用甲醇、乙醇、正丙醇、异丙醇、1,2-丁二醇1-甲醚、1,2-丙二醇1-正丙醚、四氢呋喃或丙酮。
用于本发明目的的术语“非水混的有机溶剂”是在大气压下水溶性低于10%的有机溶剂。可考虑的溶剂尤其是卤化脂族烃类,例如二氯甲烷、氯仿和四氯化碳、羧酸酯如碳酸二甲酯、碳酸二乙酯、碳酸丙烯酯、甲酸乙酯、乙酸甲酯、乙酸乙酯或乙酸异丙酯、和醚类如甲基叔丁基醚。优选的非水混溶剂是选自以下的化合物:碳酸二甲酯、碳酸丙烯酯、甲酸乙酯、乙酸乙酯、乙酸异丙酯和甲基叔丁基醚。
当步骤a2)中使用非水混的溶剂时,可以有利地将步骤a3)之后获得的分散体从非水混的溶剂中释放,例如在步骤b)中将蛋白质絮凝出来之前通过蒸馏来进行。
此外,本发明方法优选是含类胡萝卜素干粉的制备。
本发明的特别优选的含类胡萝卜素干粉是含有选自以下活性化合物的那些:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质(canthaxanthin)、柠黄质(citranaxanthin)、海胆酮、叶黄素、番茄红素和玉米黄质。
在上述含类胡萝卜素干粉的特别优选生产方法中,
a)在30℃以上的温度下,将一种或多种类胡萝卜素溶于水混性有机溶剂中,或者溶于水与水混性有机溶剂的混合物中,
b)将所得溶液与酪蛋白水溶液或酪蛋白酸盐溶液混合,
c)在分散体的pH为酪蛋白或酪蛋白酸盐的等电点范围内时,将酪蛋白或酪蛋白酸盐与类胡萝卜素一起从分散体中絮凝出来,
d)将絮凝出的固体从水和溶剂中分离出来并干燥。
上述含类胡萝卜素的制品通常是以这样的方式制备的:在30℃以上的温度下,优选50-240℃,特别是100℃-200℃,特别优选140-180℃,如果适宜的话在压力下,将至少一种类胡萝卜素溶于水混性有机溶剂中。
由于在一定环境下高温作用可以降低所需高比例的全反式异构体,因此将该类胡萝卜素可以尽可能快地溶解,例如几秒钟左右,例如0.1-10秒钟,特别优选低于1秒钟。就分子分散体的快速生产而言,使用高压,例如20bar-80bar,优选30-60bar是有益的。
然后以将混合物温度设定为约35℃-80℃的方式,将所得分子分散体与可能冷却的含水分子分散体或酪蛋白或酪蛋白酸盐的胶体分散体直接加入。
将溶剂组分转移到含水相中,并且类胡萝卜素的疏水相形成纳米分散相。
就上述分散的过程和设备的更详细的说明,可以参见EP-B-0065193。
在步骤c)中将酪蛋白或酪蛋白酸盐絮凝出来,特别是在分散体的pH为4.0-5.5,优选4.4-5.2,特别优选4.6-5.0,尤其优选4.7-4.9。最优选在pH4.8下将酪蛋白或酪蛋白酸盐絮凝出来。
有益的保护性胶体是低分子量和/或高分子量酪蛋白或酪蛋白酸盐或其混合物。优选使用分子量为10,000-100,000的酪蛋白酸钠,特别优选MW为20,000-60,000的,例如MW为约38,000的来自Lacto Bretagne Associés S.A.(France)的酪蛋白酸钠。
所用的酪蛋白/酪蛋白酸盐的细节尤其可以在如下文献中找到:Ullmann’sEncyclopedia of Industrial Chemistry,6th Edition,1998 ElectronicRelease,Chapter 11.1.,Wiley VCH,Weinheim,Germany和CD Rmpp ChemieLexikon[Rmpp′s Chemistry Lexicon]Version 1.0,Stuttgart/New York:Georg Thieme Verlag 1995,并将该文献引入本文作为参考。
为了增加最终产物的机械稳定性,在一些情况下可以方便的向胶体中加入增塑剂,例如糖或糖醇,如蔗糖、葡萄糖、乳糖、转化糖、山梨糖醇、甘露糖醇或甘油。
为了增加活性化合物对氧化降解的稳定性,加入稳定剂如α-生育酚、叔丁基化羟甲苯、叔丁基化羟茴香醚、抗坏血酸或乙氧喹是有益的。可以将它们加入水相或溶剂相中,但是优选将它们与活性化合物一起溶于溶剂相中。
在某些情况下,也可以有益地另外在溶剂相中溶解生理上允许的油,例如芝麻油、玉米油、棉籽油、大豆油或花生油和中链植物脂肪酸酯,以活性化合物为基础计其浓度为0-500%wt,优选10-300%wt,特别优选20-100%wt,然后将它与活性化合物一起极细分散地沉淀出,并且所述添加剂与水相混合。
本发明还涉及上述水溶性、少量水溶性或水不溶性活性化合物之中至少一种的固体制品,该活性化合物适用于食品和动物饲料成分或者适用于药品和化妆品,并且它们是通过最初所述的方法之一获得的。
这里优选含有适用于食品和动物饲料成分或适用于药品和化妆品的至少一种少量水溶性或水不溶性活性化合物的固体制品。
本发明干粉中的活性化合物含量是0.1-80%wt,优选1.0-75%wt,特别优选5.0-70%wt,尤其优选20-65%wt。
本文中优选的固体制品是含类胡萝卜素的干粉,特别是含类胡萝卜素并选自以下的干粉:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。
在含水体系中,在所用蛋白质保护性胶体等电点的pH之外,可以容易地将本发明的固体制品再分散。
本发明的干粉特别适宜作为食品和动物饲料的添加剂以及作为化妆品和药品的添加剂。在动物饲料成分中含类胡萝卜素干粉的典型应用领域例如有,在水产养殖中的鱼着色和家禽饲养中的蛋黄和小鸡皮肤着色。
就上述用途而言,有利地将干粉以油性悬浮液形式使用。
因此本发明还涉及含有作为分散相的至少一种水溶性、少量水溶性或水不溶性活性化合物的油性悬浮液,所述活性化合物被一种或多种保护性胶体所包围并适用于食品和动物饲料成分或者适用于药品和化妆品,条件是所述油性悬浮液不含水溶性维生素。
上述水溶性维生素尤其是抗坏血酸及其盐如抗坏血酸钠和维生素C衍生物如抗坏血酸-2-一磷酸的钠盐、钙盐或镁盐或者抗坏血酸-2-聚磷酸钙、泛酸钙、羟泛酸、维生素B1(硫胺素),如其盐酸盐、硝酸盐或焦磷酸盐、维生素B2(核黄素)及其磷酸盐、维生素B6及其盐、维生素B12、生物素、叶酸和叶酸衍生物如四氢叶酸、5-甲基四氢叶酸、5-甲酰基四氢叶酸、烟酸和烟酰胺。
本发明油性悬浮液的优选实施方式在于,它们含有作为分散相的适用于食品和动物饲料成分或者适用于药品和化妆品的至少一种水溶性、少量水溶性或水不溶性活性化合物的固体制品,它们是通过如下获得的:
a)将上述活性化合物中至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将蛋白质保护性胶体与活性化合物一起从分散体中絮凝出来,和
c)将絮凝出的固体从水和附加使用的任意溶剂中分离出来,接着将它们转变成干粉。
还优选这些油性悬浮液含有至少一种类胡萝卜素作为活性化合物。
可用于本发明内容的类胡萝卜素是可以由天然源或合成获得的这类物质的已知代表。例如是以下这些化合物单独或其混合物:β-胡萝卜素、番茄红素、叶黄素、虾青素、玉米黄质、隐黄质、柠黄质、斑螯黄质、海胆酮、红木素、β-阿朴-4-胡萝卜素醛、β-阿朴-8-胡萝卜素醛、β-阿朴-8-胡萝卜素酸酯类。优选至少一种类胡萝卜素来自虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。特别优选的类胡萝卜素是虾青素和斑螯黄质,尤其优选虾青素。
作为保护性胶体,分散相,除了上述蛋白质类化合物,例如明胶如牛明胶、猪明胶或鱼明胶、明胶水解物、酪蛋白、酪蛋白酸盐、乳清蛋白和植物蛋白之外,还可以单独或混合地含有淀粉、糊精、果胶、阿拉伯胶、改性淀粉,例如辛烯基琥珀酸淀粉钠、高直链淀粉(例如Hylon,National Starch)。植物蛋白的典型代表是谷蛋白、玉米蛋白、大豆蛋白、大米蛋白、马铃薯蛋白和豌豆蛋白。然而,也可以使用聚乙烯醇、聚乙烯吡咯烷酮、甲基纤维素、羧甲基纤维素、羟丙基纤维素和藻酸盐。优选保护性胶体是至少一种选自以下的蛋白质保护性胶体:酪蛋白、酪蛋白酸盐、大豆蛋白、大豆蛋白水解物、猪明胶和鱼明胶、或者改性淀粉。
关于上述保护性胶体的其它细节参见R.A.Morton,Fat Soluble Vitamins,Intern.,Encyclopedia of Food and Nutrition,Vol.9,Pergamon Press 1970,pp.128-131。
为了提高其性能,可以将这些保护性胶体与乳化剂混合。
本发明的油性制品,特别是含类胡萝卜素的油性悬浮液性能优良,尤其是在下列含水量下:水分含量为0.1-6%wt,优选0.2-4%wt,特别优选0.5-3%wt。
油性悬浮液的分散相的平均细度D[4.3]是0.1-100μm,优选0.2-50μm,特别优选0.5-30μm,尤其优选0.8-20μm,特别是1.0-10μm。术语D[4.3]在本文中是指容重平均直径(参见handbook on the Malvern Mastersizer S,MalvernInstruments Ltd.,UK)。
在优选的含类胡萝卜素的油性悬浮液中,至少一种类胡萝卜素以非晶形或者部分非晶形的形式存在。以非晶形存在的类胡萝卜素的比例,经x-射线衍射图测定,为30-100%,优选40-99%,特别优选60-98%,尤其优选70-95%。
由于活性化合物,特别是类胡萝卜素在油性悬浮液中非晶形度非常高,因此这些制品呈现出特别高的生物利用度,并且在例如蛋黄或如大麻哈鱼的鱼着色时得到非常好颜色的产品。
以油性悬浮液的总量为基础计,活性化合物在油性悬浮液中的含量通常是0.1-50%wt,优选0.2-30%wt,特别优选0.5-20%wt,尤其特别优选1.0-15%wt。
所用分散介质在20℃下可以是固体或液体,并且不仅可以是合成的、矿物或植物源,而且也可以是动物源。其中,典型代表是芝麻油、玉米油、棉籽油、大豆油或花生油、中链植物脂肪酸酯类、食用牛油、油硬脂精和石蜡油、硬脂酸甘油酯、豆蔻酸异丙酯、己二酸二异丙酯、2-乙基己酸十六烷基硬脂酰酯、氢化聚异丁烯、凡士林、辛酸/癸酸甘油三酸酯、微晶蜡、羊毛脂和硬脂酸。
本文优选20℃下呈液态的食用油,例如葵花籽油、棕榈油、芝麻油、玉米油、棉籽油、大豆油或花生油、中链甘油三酸酯、以及鱼油,例如鲭鱼油、西鲱鱼油或大麻哈鱼油。就动物营养而言,特别优选的是鱼油、玉米油、向日葵油、大豆油和花生油。另外有益于食品/药品成分的那些是中链甘油三酸酯。
根据所用的分散介质(油或硬脂),本发明的悬浮液可以是作为固体/液体体系的自由流动形式,或者,根据其粘性和分散介质的熔点,它可以是固体形式,也就是说作为不均匀固体/固体体系。
为了避免油性制品中含类胡萝卜素颗粒的沉淀,例如贮藏相当长的时间的情况下,在一定情况下上述硬脂(例如食用牛油或油硬脂精)也是优选的分散介质。
以油性悬浮液的总量计,分散介质的量通常为20-99.9%wt,优选50-99%wt,特别优选55-97%wt,尤其优选60-99%wt。
在某些情况下,油性悬浮液可以必需含有其它助剂,例如增稠剂、硬脂、螯合剂,例如柠檬酸、肌醇六磷酸或磷酸的碱金属盐或碱土金属盐和/或乳化剂。
可以使用的乳化剂或加溶剂例如有抗坏血酸棕榈酸酯、聚脂肪酸甘油酯、脂肪酸脱水山梨醇酯、脂肪酸丙二醇酯或卵磷脂。
本发明还涉及油性分散体,它含有作为分散相的至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品,其适用于食品和动物饲料成分或用于药品和化妆品,它们可通过如下获得:
a)将上述活性化合物中至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将蛋白质保护性胶体与活性化合物一起从分散体中絮凝出和
c)将絮凝出的固体从水和附加使用的任何溶剂中分离出来,接着将它们转变成干粉。
当油性悬浮液含有作为分散相的上述絮凝固体时,以油性分散体的总量计,分散介质的量通常为50-99.9%wt,优选70-99.8%wt,特别优选80-99.5%wt,尤其优选90-99%wt。
本发明还涉及一种生产含类胡萝卜素油性悬浮液的方法,优选油性悬浮液含有作为活性化合物的至少一种选自以下的类胡萝卜素:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质,该方法包括:
a)在至少一种油中将含有用一种或多种保护性胶体包围的至少一种类胡萝卜素的干粉研磨至平均细度为0.1-100μm,或者
b)没有使用连续相的情况下将含有用一种或多种保护性胶体包围的至少一种类胡萝卜素干粉研磨至平均细度为0.1-100μm,然后将研碎的颗粒悬浮于至少一种油中,或者
c)将含类胡萝卜素的悬浮液研磨至平均细度为0.1-100μm,该悬浮液含有作为固体分散相的至少一种用一种或多种保护性胶体包围的类胡萝卜素,并且含有作为分散介质的水或者水与水混性溶剂的混合物,然后将该固相从水或水/溶剂混合物中释放,并将所得研碎颗粒悬浮于至少一种油中。
在所有三个方法变体中,可以本身已知的方式,例如使用球磨机进行研磨。根据所用研磨机的类型,进行连续研磨,直到颗粒的平均细度D[4.3](它是通过Fraunhofer衍射测定的)为0.1-100μm,优选0.2-50μm,特别优选0.5-30μm,尤其优选0.8-20μm,特别是1.0-10μm。
关于研磨及其使用设备的其它细节尤其可以在如下文献中找到:Ullmann’sEncyclopedia of Industrial Chemistry,Sixth Edition,1999,ElectronicRelease,Size Reduction,Chapter 3.6.:Wet Grinding。
在方法变体c)中所用的水混性溶剂是特定水混性、热稳定的挥发性溶剂,它仅含有碳、氢和氧,例如醇类、醚类、酯类、酮类和缩醛类。方便地,使用那些至少10%可水混、沸点低于200℃和/或少于10个碳的溶剂。特别优选使用甲醇、乙醇、正丙醇、异丙醇、1,2-丁二醇1-甲醚、1,2-丙二醇、1-正丙醚、四氢呋喃或丙酮。
在方法c)中可以使用本身为已知的方式,例如通过蒸馏,如果适宜的话在减压下,将水或水/溶剂混合物分离出来。蒸馏通常在研磨之后进行,但是也可以在研磨过程中进行。
在本发明的方法中,用作分散介质的油是20℃下为液体的食用油,或者20℃下为固体的硬脂。
关于所用的保护性胶体和分散介质的其它细节已在最初给出的油性悬浮液的说明中给出了。
通常用于研磨的干粉可以是现有技术中已知的全固体制品,其中存在至少一种用保护性胶体包围的类胡萝卜素。
优选如以下文献中所述生产的干粉:EP-A-0065193、EP-A-0832569、DE-A-19919751、WO98/26008、EP-A-0937412、WO91/062292和WO94/19411。
EP-A-0065193中所述的类胡萝卜素干粉可以通过如下方法获得:在高温下简单地将类胡萝卜素溶于水混性有机溶剂中,通过与保护性胶体的水溶液快速混合,将类胡萝卜素以胶体分散体形式从所得溶液中沉淀,并将所得分散体转变成干粉。
根据EP-A-0832569,通过在40-90℃的温度下将根据EP-A-0065193生产的分散体加热,然后将其喷雾干燥,获得类胡萝卜素干粉,其中通过X-射线衍射显示,这些活性化合物颗粒基本上为非晶形。
DE-A-19919751中所述的干粉含有至少一种选自以下的叶黄素:虾青素、叶黄素和玉米黄质,它包含在作为保护性胶体的酪蛋白基质中。
WO98/26008中所述的干粉含有至少一种叶黄素,这种叶黄素包含在低分子量保护性胶体和高分子量保护性胶体的混合物基质中。
EP-A-0937412涉及通过如下获得的粉状类胡萝卜素制品:a)在有或者没有抗氧化剂和/或油的情况下将类胡萝卜素悬浮于非水混的溶剂中;b)将该悬浮液加热至100-250℃的温度;c)将b)所得的溶液与保护性胶体水溶液在20-100℃下混合;d)分离出有机溶剂,并将该分散体转变成干粉。
WO91/062292中公开的干粉是通过将类胡萝卜素在保护性胶体水溶液中研磨,并且接着将研碎的类胡萝卜素含水悬浮液喷雾干燥获得的。
在WO94/19411中,在有保护性胶体水溶液的情况下将结晶类胡萝卜素研磨,通过短时加热至熔点将其转变成非晶形改性,然后喷雾干燥。
关于这些干粉生产的其它细节,参见上述公开物的说明书。
用于生产本发明油性悬浮液的类胡萝卜素干粉,除了保护性胶体之外,可以含有其它助剂如增塑剂、乳化剂和/或稳定剂。
所用的增塑剂是糖类和糖醇,例如蔗糖、葡萄糖、乳糖、转化糖、山梨糖醇、甘露糖醇或甘油。
保护性胶体和增塑剂与类胡萝卜素的比例通常以如下方式选择:干粉含有0.5-65%wt,优选1-25%wt的类胡萝卜素;含有10-50%wt,优选15-35%wt的保护性胶体;含有20-70%wt,优选30-60%wt的增塑剂,所有百分比都是以粉末的干重为基础的,含有少量的稳定剂或不含稳定剂。
为了增加类胡萝卜素抗氧化降解的稳定性,以干粉总量计,可以有益地加入0-10%wt,优选0.5-7.5%wt的一种或多种稳定剂如α-生育酚、叔丁基化的羟基甲苯、叔丁基化的羟基茴香醚、抗坏血酸或乙氧喹。
乳化剂可以是例如抗坏血酸棕榈酸酯、聚甘油脂肪酸酯、脱水山梨醇脂肪酸酯、丙二醇脂肪酸酯或卵磷脂,以干粉中的类胡萝卜素计,其浓度为0-200%wt,优选5-150%wt,特别优选10-80%wt。
当为类胡萝卜素混合物时,在本发明的研磨过程中,可以将悬浮液中所用的所有组分作为一个总的混合物研磨。然而,待研磨的每一种类胡萝卜素也可以在所用的油中以高浓度单独研磨。然后通过将各自单独的悬浮液混合生产最终制品。
在使用之前,通过加入脂肪或油,可以将本发明的油性悬浮液稀释至各自的使用浓度。它们可以例如在高温下,例如在30-80℃下搅拌稀释。
上述悬浮液尤其适宜作为动物饲料和食物制品或混合饲料,作为生产药品和化妆品的组分和用于生产人和动物的食品补充制品。
优选这些悬浮液可以用作动物营养的饲料添加剂,例如通过在挤出过程中掺入饲料颗粒或者涂布或喷雾到饲料颗粒上。
用作饲料添加剂尤其是在有或没有用油稀释的情况下通过称之为后造粒涂布的方法将本发明的悬浮液直接喷雾到例如动物饲料颗粒上进行的。
喷雾法的优选实施方式是在减压下将饲料颗粒用油性悬浮液加料。
该例子尤其可在GB-A-2232573和EP-A-0556883中找到。
用于食品成分的典型领域例如饮料、乳制品如酸奶、风味化乳饮料或乳制冰淇淋,和布丁粉、蛋制品、焙烤混合物和甜食的维生素化和着色。
在化妆品成分中,可以将油性悬浮液用于例如装饰性身体保护产品,例如以乳膏、洗剂的形式作为口红或化妆品。
本发明还涉及含有前面所述的油性悬浮液的食品补充物、动物饲料、食品和药品和化妆品。
本发明优选涉及用所述悬浮液装料的动物饲料,尤其是饲料颗粒。
含有本发明悬浮液的食品补充制品和药品尤其是片剂、糖衣药丸,并且优选硬和软明胶胶囊。
可以含有本发明悬浮液的化妆品例如是可以局部涂敷的制品,尤其是以乳膏、洗剂形式存在的装饰性身体保护产品如口红、脸部化妆品。
当为开始所述的吸收紫外线的活性化合物(防晒)时,本发明含防晒物的固体制品以及由此生产的油性分散体也适宜作为化妆品和药品中的光稳定性紫外线过滤器,从而单独或与已知用于化妆品或药品并吸收紫外线的化合物一起用于保护人皮肤或人头发免受日光和高紫外线含量人工光的照射。同时该化妆品和药品本身显然也是稳定的,从而尽可能长地保持了活性。
因此,本发明还涉及含防晒物的化妆品和药品,用于防止人皮肤或人头发受到280-400nm的紫外线光照射,它是在化妆品方面或制药方面适宜的载体中单独含有活性量的少量水溶性或水不溶性有机紫外线滤过物质制品,或者与本身已知用于化妆品和药品的在UVA和UVB的范围内吸收的化合物一起作为光稳定性紫外线过滤剂,其中这些制品是前面所述的本发明的固体制品或者由其生产的油性分散体。
以化妆品和药品的总量计,少量水溶性或水不溶性有机紫外线滤过物质在用于化妆品和药品的本发明制品形式中的量是0.05-20%wt,优选0.1-10%wt,特别优选1-7%wt。
含防晒物的化妆品和药品通常以含有至少一种油相的载体为基质。然而,制品也可以仅以水为基础。因此,组合物是油、水包油和油包水乳剂、乳膏和糊剂、保护性口红组合物或无脂凝胶。
乳剂尤其是以分散形式含有式I的氨基取代的羟基二苯酮的O/W粗乳剂、O/W微乳剂或O/W/O乳剂,这些乳剂可以通过DE-A-19726121的相转化技术获得。
可以考虑用作添加剂的常规化妆品助剂有如辅助乳化剂、脂肪和蜡、稳定剂、增稠剂、生物活性化合物、成膜剂、香料、染料、上光剂、防腐剂、颜料、电解质(例如硫酸镁)和pH调节剂。可考虑的辅助乳化剂优选已知的W/O乳化剂以及其它O/W乳化剂,例如聚甘油酯、脱水山梨糖醇酯或部分酯化的甘油酪。脂肪的典型例子是甘油酯;蜡尤其是蜂蜡、石蜡或微蜡,可以与亲水蜡混合。可以使用的稳定剂是脂肪酸的金属盐,例如硬脂酸镁、硬脂酸铝和/或硬脂酸锌。适宜的增稠剂是例如交联聚丙烯酸及其衍生物、多糖,特别是黄原胶、瓜尔胶、琼脂、藻酸盐和纤基乙酸钠、羧甲基纤维素和羟乙基纤维素、其它脂肪醇、单甘油酯和脂肪酸、聚丙烯酸酯、聚乙烯醇和聚乙烯基吡咯烷酮。生物活性化合物是例如植物提取物、蛋白质水解物和维生素复合物。常规成膜剂是例如亲水胶体,例如壳聚糖、微晶壳聚糖或季化壳聚糖、聚乙烯基吡咯烷酮、乙烯基吡咯烷酮/乙酸乙烯酯共聚物、丙烯酸系列的聚合物、季纤维素衍生物和类似化合物。适宜的防腐剂是例如甲醛溶液、对羟基苯甲酸盐或山梨酸。上光剂是例如二硬脂酸二醇酯类如二硬脂酸乙二醇酯,但是还有脂肪酸和脂肪酸单二醇酯类。可以使用的染料是批准并适用于化妆品的染料,如汇编于出版物“Kosmetische Farbemittel”[Cosmetics Dyes]of the Farbstoffkommissionder Deutschen Forschungsgeinschaft,[Dye Commission of the GermanResearch Association],published by Verlag Chemie,Weinheim,1984中的。以总混合物计,这些染料经常以0.001-0.1%wt的浓度使用。
附加含量的抗氧化剂通常也是优选的。因此适用于或常用于化妆品和/或皮肤病学应用的所有抗氧化剂都可用作良好的抗氧化剂。
有利地,抗氧化剂选自:氨基酸类(例如甘氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物、咪唑类(例如尿刊酸)及其衍生物、肽如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(例如鹅肌肽)、类胡萝卜素、胡萝卜素(例如β-胡萝卜素、番茄红素)及其衍生物、绿原酸及其衍生物、硫辛酸及其衍生物(例如二氢硫辛酸)、金硫葡糖、丙基硫尿嘧啶和其它硫醇类(例如thiorodoxin、谷胱甘肽、半胱氨酸、胱氨酸、胱胺及其葡基酯、N-乙酰酯、甲酯、乙酯、丙酯、戊酯、丁酯和月桂酯、棕榈酰酯、油酰酯、γ-亚油酰酯、胆甾醇酯和甘油酯)及其盐、硫代二丙酸二月桂酯、硫代二丙酸二硬脂基酯、硫代二丙酸及其衍生物(酯、醚、肽、脂类、核苷酸、核苷及其盐)和以非常低的可接受量(例如Pmoe-μmoe/kg的磺基肟(Sulfoximine)化合物(例如丁硫磺基肟、高半胱氨酸磺基肟、丁硫砜、戊-、己-和庚硫磺基肟),此外(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、肌醇六磷酸、乳铁蛋白)、α-羟基酸(例如柠檬酸、乳酸、苹果酸)、腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、EDTA及其衍生物、不饱和脂肪酸及其衍生物(例如γ-亚麻酸、亚油酸、油酸)、叶酸及其衍生物、泛醌和泛醌醇(ubiquinol)及其衍生物、维生素C及其衍生物(例如抗坏血酸棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸乙酸酯)、生育酚及其衍生物(例如维生素E乙酸酯、生育三烯酚)、维生素A及其衍生物(维生素A棕榈酸酯)和安息香树脂的松柏基苯甲酸酯、芸香酸及其衍生物、α-葡基芸香苷、阿魏酸、呋喃亚甲基葡糖醇、肌肽、丁基化羟甲苯、丁基化羟茴香醚、去甲二氢愈创木脂树脂酸、去甲二氢愈创木酸、三羟基丁酰苯、尿酸及其衍生物、甘露糖及其衍生物、锌及其衍生物(例如ZnO、ZnSO4)、硒及其衍生物(例如硒代蛋氨酸)、二苯乙烯及其衍生物(例如氧化二苯乙烯、反式-氧化二苯乙烯)。
以制品总量计,上述抗氧化剂(一种或多种化合物)在制品中的量优选为0.001-30%wt,特别优选0.05-20%wt,尤其是1-10%wt。
如果维生素E和/或其衍生物是抗氧化剂,那么以制品总量计,有利地选择其它们各自的浓度为0.001-10%wt。
如果维生素A和/或其衍生物或类胡萝卜素是抗氧化剂,那么以制品总量计,有利地选择其各自浓度为0.001-10%wt。
化妆品中常用油的组分是例如石蜡油、甘油硬脂酸酯、豆蔻酸异丙酯、己二酸二异丙酯、2-乙基己酸十六烷基硬脂酰酯、氢化聚异丁烯、凡士林、辛酸/癸酸甘油三酸酯、微晶蜡、羊毛脂和硬脂酸。
以介质为基础计,助剂和添加剂的总量可以是1-80,优选6-40%wt,并且非水部分(“活性物”)可以是20-80,优选30-70%wt。介质可按本身为已知的方式制备,也就是说例如通过热、冷、热-热/冷或PIT乳化。这是一个纯机械的过程:没有发生化学反应。
因此这些防晒制品可以为液体、糊剂或固体形式,例如作为油包水乳膏、水包油乳膏和洗剂、气溶胶泡沫乳膏、凝胶、油、脂肪棒、粉末、喷雾剂或含水醇洗剂。
最后,可以结合使用吸收紫外线且本身为已知的其它物质,只要它们在本发明使用的紫外线滤过物的组合整体体系中稳定。
在化妆品和药品中用于保护人表皮防晒物的主要部分,由在UVB区域,即在280-320nm吸收紫外线的化合物组成。例如,以UVB和UVA吸收物的总量为基础计,本发明使用的UVA吸收剂的含量是10-90%wt,优选20-50%wt。
可将作为紫外线滤过物的任意UVA和UVB过滤物与本发明使用的制品组合使用。例子有:
编号 | 物质 | CAS No.(=酸) |
1 | 4-氨基苯甲酸 | 150-13-0 |
2 | 3-(4’-三甲基铵)亚苄基硼烷-2-酮硫酸甲酯 | 52793-97-2 |
3 | 3,3,5-三甲基环己基水杨酸酯(homosalatum) | 118-56-9 |
4 | 2-羟基-4-甲氧基二苯酮(oxybenzonum) | 131-57-7 |
5 | 2-苯基苯并咪唑-5-磺酸及其钾盐、钠盐和三乙醇铵盐 | 27503-81-7 |
6 | 3,3’-(1,4-亚苯基二次甲基)二(7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲磺酸)及其盐 | 90457-82-2 |
7 | 4-二(聚乙氧基)氨基苯甲酸聚乙氧基乙酯 | 113010-52-9 |
8 | 4-二甲氨基苯甲酸(2-乙基己基)酯 | 21245-02-3 |
9 | 水杨酸(2-乙基己基)酯 | 118-60-5 |
10 | 4-甲氧基肉桂酸(2-异戊基)酯 | 71617-10-2 |
11 | 4-甲氧基肉桂酸(2-乙基己基)酯 | 5466-77-3 |
12 | 2-羟基-4-甲氧基二苯酮-5-磺酸(sulisobenzonum)及其钠盐 | 4065-45-6 |
13 | 3-(4’-磺基)亚苄基硼烷-2-酮及其盐 | 58030-58-6 |
14 | 3-亚苄基硼烷-2-酮 | 16087-24-8 |
15 | 1-(4’-异丙基苯基)-3-苯基丙烷-1,3-二酮 | 63260-25-9 |
16 | 4-异丙基苄基水杨酸酯 | 94134-93-7 |
17 | 2,4,6-三苯氨基-(邻羰基-2’-乙基-1’-己氧基)-1,3,5-三嗪 | 88122-99-0 |
18 | 3-咪唑-4-基丙烯酸及其乙酯 | 104-98-3 |
19 | 2-氰基-3,3-二苯基丙烯酸乙酯 | 5232-99-5 |
20 | 2-氰基-3,3-二苯基丙烯酸(2’-乙基己基)酯 | 6197-30-4 |
21 | 邻氨基苯甲酸基酯类或:5-甲基-2-(1-甲基乙基)-2-氨基苯甲酸酯类 | 134-09-8 |
22 | 对氨基苯甲酸甘油酯或:4-氨基苯甲酸(1-甘油基)酯 | 136-44-7 |
23 | 2,2’-二羟基-4-甲氧基二苯酮(二氧苯酮类) | 131-53-3 |
24 | 2-羟基-4-甲氧基-4-甲基二苯酮(mexonone) | 1641-17-4 |
25 | 三乙醇胺水杨酸酯 | 2174-16-5 |
26 | 二甲氧基苯基乙醛酸或:3,4-二甲氧基苯基乙醛酸钠 | 4732-70-1 |
27 | 3-(4’-磺基)亚苄基硼烷-2-酮及其盐 | 56039-58-8 |
28 | 4-叔丁基-4’-甲氧基二苯甲酰基甲烷 | 70356-09-1 |
29 | 2,2’,4,4’-四氢二苯酮 | 131-55-5 |
30 | 2,2’-亚甲基二[6(2H-苯并三唑-2-基)-4-(1,1,3,3-四甲基丁基)苯酚] | 103597-45-1 |
31 | 2,2’-(1,4-亚苯基)二-1H-苯并咪唑-4,6-二磺酸,钠盐 | 180898-37-7 |
32 | 2,4-二[4-(2-乙基己氧基)-2-羟基]苯基-6-(4-甲氧基苯基)-(1,3,5)-三嗪 | 187393-00-6 |
33 | 3-(4-甲基亚苄基)樟脑 | 36861-47-9 |
34 | 4-二(聚乙氧基)对氨基苯甲酸聚乙氧基乙酯 | 113010-52-9 |
35 | 2,4-二羟基二苯酮 | 131-56-6 |
36 | 2,2’-二羟基-4,4’-二甲氧基二苯酮-5,5’-二磺酸钠 | 3121-60-6 |
按照本发明,也可以使用聚合或聚合物连接的过滤物。
有利地,本发明的化妆品和皮肤病学制品也可以含有以金属氧化物为基础的无机颜料和/或其它少量水溶性或水不溶性的金属化合物,特别是钛的氧化物(TiO2)、锌的氧化物(ZnO)、铁的氧化物(例如Fe2O3)、锆的氧化物(ZrO2)、硅的氧化物(SiO2)、锰的氧化物(例如MnO)、铝的氧化物(Al2O3)、铈的氧化物(例如Ce2O3),相应金属的混合氧化物和这些氧化物的混合物。特别优选这些颜料基于TiO2和ZnO。
尽管不是限制性的,但是本发明特别有利的是无机颜料以疏水形式存在,即它们以防水的方式经过表面处理。这种表面处理可以是以本身为已知的方式将颜料以疏水薄涂层来提供,如DE-A-3314742中所述。
为了防止人头发受到紫外线的照射,可以将本发明的防晒制品加入香波、洗剂、凝胶、发胶、气溶胶泡沫膏或乳剂中,其浓度为0.1-10%wt,优选1-7%wt。这里,尤其可以将各种制品用于洗发、染发或头发造型。
本发明所用制品通常的特征在于在具有尖谱带结构的UVA照射区的吸收能力特别高。此外,它们易溶于化妆品油中并且可以容易地掺入到化妆品中。使用这些制品所生产的乳剂的特征尤其在于它们特别稳定,制品I本身的光稳定性高,并且这些制品给皮肤带来舒适感。
本发明制品的紫外线过滤剂也可用于稳定化妆品和药品中的活性化合物和助剂。
本发明制品的特征在于在具有尖谱带结构的UVB照射范围内的吸收能力特别高并且防晒因子高。
具体地说,这些制品的高防晒因子,甚至在低浓度的UV吸收活性化合物下测定时也是出人意料的。
具体实施方式
在下面的实施例中,详细描述本发明方法的步骤。
实施例1
虾青素干粉
在室温下将45g结晶虾青素悬浮于375g共沸的异丙醇/水混合物中。然后将该活性化合物悬浮液加热到96℃,并在2.1kg/h的流速下与在227℃的温度和2.7kg/h的流速下的另外的异丙醇/水共沸物连续混合,虾青素在169℃的混合温度和60bar的压力下溶解。然后在56.1kg/h的流速下将所得活性化合物溶液与如下的水相溶液混合:80g酪蛋白酸钠的12L蒸馏水溶液,其中使用18mL的1M NaOH将其pH调整至8.0。
混合过程中形成的纳米粒子活性化合物颗粒在异丙醇/水混合物中的细度是100nm。然后使用1M HCl将该活性化合物分散体调整至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。通过一过滤器袋将絮凝粒子过滤出来,接着冷冻干燥之后,获得虾青素含量为36%wt的干粉。
实施例2
虾青素干粉
在室温下将50g结晶虾青素和5.6g乙氧喹悬浮于416g共沸的异丙醇/水混合物中。然后将该活性化合物悬浮液加热到97℃,并在2.1kg/h的流速下与在216℃的温度和2.7kg/h的流速下的另外的异丙醇/水共沸物连续混合,虾青素在169℃的混合温度和60bar的压力下溶解。然后在55.6kg/h的流速下将所得活性化合物溶液与如下水相溶液混合:23.3g酪蛋白酸钠的14L蒸馏水溶液,其中使用5mL的1M NaOH将其pH调整至8.3。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的细度是116nm。然后使用1M HCl将该活性化合物分散体调整至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。然后通过一过滤器袋将悬浮液过滤并将滤饼干燥,所得固体的虾青素含量为62%wt。
实施例3
番茄红素干粉
在室温下将45g结晶番茄红素、3.6g棕榈酸和6.6g生育酚悬浮于388g共沸的异丙醇/水混合物中。然后将该活性化合物悬浮液加热到94℃,并在2.0kg/h的流速下与在206℃的温度和3.3kg/h的流速下的另外的异丙醇/水共沸物混合,番茄红素在171℃的混合温度和63bar的压力下溶解。然后在33.8kg/h的流速下将所得活性化合物溶液与如下的水相溶液混合:80g酪蛋白酸钠的7L蒸馏水溶液,其中使用19mL的1M NaOH将其pH调整至8.0。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的细度是125nm。然后使用1M HCl将该活性化合物分散体调整至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。然后通过一过滤器袋将悬浮液过滤并冷冻干燥。干燥滤饼的番茄红素含量为32%wt。
实施例4
β-胡萝卜素干粉
在室温下将45g β-胡萝卜素、3.6g抗坏血酸棕榈酸酯和6.6g生育酚悬浮于388g共沸的异丙醇/水混合物中。然后将该活性化合物悬浮液加热到96℃,并在2.1kg/h的流速下与在210℃的温度和3.0kg/h的流速下另外的异丙醇/水共沸物混合,β-胡萝卜素在170℃的混合温度和62bar的压力下溶解。然后在35.5kg/h的流速下将该活性化合物溶液与如下溶液的水相混合:80g酪蛋白酸钠的7L蒸馏水溶液,其中使用18mL的1M NaOH将其pH调整至8.0。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的细度是138nm。然后使用1M HCl将该活性化合物分散体调整至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。然后通过一过滤器袋将悬浮液过滤。滤饼然后经并冷冻干燥。干燥滤饼的β-胡萝卜素含量为32%wt。
实施例5
虾青素干粉(酸法)
在室温下将45g结晶虾青素和4.5g香兰素悬浮于375g共沸的异丙醇/水混合物中。然后将该活性化合物悬浮液加热到98℃,并在2.1kg/h的流速下与在230℃的温度和2.8kg/h的流速下的另外的异丙醇/水共沸物连续混合,虾青素在171℃的混合温度和61bar的压力下溶解。然后在55.2kg/h的流速下将所得活性化合物溶液与如下的水相溶液混合:80g酪蛋白酸钠(Lacto Bretagne Associés)的12000g蒸馏水溶液,其中使用88g的1M HCl将其pH调整至2.9。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的细度是1.2μm。然后使用1M NaOH将该活性化合物分散体调整至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。然后通过一过滤器袋将悬浮液过滤。滤饼然后经冷冻干燥,干燥滤饼的虾青素含量为35%wt。
实施例6
用酪蛋白酸盐研磨番茄红素
在室温下将3.3g结晶番茄红素、2.5g酪蛋白酸钠和0.33g抗坏血酸棕榈酸酯悬浮于40g去离子水中,并用3g的1N NaOH使该悬浮液的pH为碱性。将该活性化合物悬浮液与约200g、直径为1mm的氧化锆陶瓷研磨珠一起分散在100ml玻璃烧瓶中的Red Devil混合器上。研磨时间为3、6和12小时之后,取出样品,以便鉴定研磨过程。在这些时间下的平均细度是651nm,方差67%;487nm,方差50%;494nm,方差55%。在E1/1值为136下,最终样品的pH是7.7。
然后使用1M HCl将该活性化合物分散体调节至pH4.8,致使活性化合物/酪蛋白酸盐颗粒絮凝出。然后通过一过滤器袋过滤,滤饼然后经冷冻干燥。
实施例7
虾青素的油悬浮液
为了生产高度浓缩的油性虾青素悬浮液,使用Ultra Turrax将20g如实施例2中获得的虾青素干粉与1.0g乙氧喹、1.0g防腐剂(BHT)和4.0g乳化剂(Span65,Sigma)在100g中性油(Delios SK,Grünau)悬浮5分钟。所得对沉降稳定的油悬浮液中虾青素含量为8.5%wt,二级细度是34μm。
实施例8
虾青素的油悬浮液
将2kg的含虾青素30%wt的干粉(LucantinPink 10%strength,BASF AG)和70%wt大豆油的混合物用轮叶搅拌器搅拌,直到悬浮液均匀。然后将该混合物转移到可搅拌的贮器中,由此通过一蠕动泵经连续球磨机(Dyno Mill KDLSpezial)将悬浮液运输。球磨机的研磨容器填充有400g玻璃球(直径为800-1200μm)。收集从球磨机中出来的细分过的悬浮液并使用细度测定装置(MalvernMastersizer)测定。重复研磨操作,直到90%的悬浮颗粒的细度低于10μm[D(0.9)<10μm]。这相应于平均细度D[4.3]是5.2μm。
从研磨体中分离出来之后,部分悬浮液用10倍量的所用油稀释,并静置12小时。在此期间,未稀释和稀释过的悬浮液都没有沉淀现象。
Claims (40)
1.一种生产至少一种水溶性、少量水溶性或水不溶性的活性化合物固体制品的方法,该制品适用于食品和动物饲料成分或者适用于药品和化妆品,其特征在于:
a)将上述活性化合物中的至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将该蛋白质保护性胶体与活性化合物一起从该分散体中絮凝出和
c)将絮凝固体从水和另外使用的任意溶剂中分离,接着将它们转变成干粉。
2.如权利要求1的生产至少一种少量水溶性或水不溶性的活性化合物固体制品的方法,该制品于食品和动物饲料成分或者适用于药品和化妆品,其中,在步骤a)中,将上述活性化合物中的至少一种分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中。
3.如权利要求2的方法,其中分散步骤a)是制备蛋白质保护性胶体的含水分子分散体或胶体分散体中至少一种固体活性化合物的悬浮液。
4.如权利要求3的方法,其中在絮凝之前将步骤a)中制备的悬浮液研碎。
5.如权利要求2的方法,其中阶段a)中的分散包括以下步骤:
a1)将一种或多种少量水溶性或水不溶性的活性化合物溶于水混性有机溶剂或者水与水混性有机溶剂的混合物中,或者
a2)将一种或多种少量水溶性或水不溶性的活性化合物溶于非水混的有机溶剂中,和
a3)将a1)或a2)获得的溶液与蛋白质保护性胶体的含水分子分散体或胶体分散体混合,活性化合物的疏水相是以纳米分散相生产的。
6.如权利要求5的方法,其中当进行步骤a2)时,在保护性胶体絮凝之前蒸馏掉非水混溶剂。
7.如权利要求1-6任一项的方法,其中,在步骤b)中,通过将分散体的pH调节至在用作保护性胶体的蛋白质等电点的范围内的值来开始絮凝。
8.如权利要求1-7任一项的方法,其中保护性胶体是酪蛋白或酪蛋白酸盐。
9.如权利要求1-8任一项的方法,其中涉及含类胡萝卜素干粉的生产。
10.如权利要求9的方法,用于生产含有选自以下类胡萝卜素的干粉:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。
11.如权利要求9的方法,其中
a)在30℃以上的温度下,将一种或多种类胡萝卜素溶于水混性有机溶剂中,或者溶于水与水混性有机溶剂的混合物中,
b)将所得溶液与酪蛋白水溶液或酪蛋白酸盐水溶液混合,
c)在分散体的pH为酪蛋白或酪蛋白酸盐等电点的范围内时,酪蛋白或酪蛋白酸盐与类胡萝卜素一起从分散体中絮凝出,
d)将絮凝固体从水和溶剂中分离出来并干燥。
12.一种至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品,其适用于食品和动物饲料成分或者适用于药品和化妆品,并且是可通过权利要求1-11之一的方法获得的。
13.如权利要求12的固体制品,含有至少一种少量水溶性或水不溶性的活性化合物,该制品适用于食品和动物饲料成分或者适用于药品和化妆品。
14.如权利要求12或13的固体制品,其活性化合物的含量是0.1-80%wt。
15.如权利要求13或14的固体制品,它是含类胡萝卜素的干粉。
16.如权利要求15的干粉,含有选自以下的类胡萝卜素:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。
17.如权利要求12的固体制品的用途,其作为食品、动物饲料、药品和/或化妆品的添加剂。
18.如权利要求17的用途,其中将固体制品以油性悬浮液的形式使用。
19.如权利要求12的固体制品的用途,用于生产油性悬浮液。
20.含有作为分散相的至少一种水溶性、少量水溶性或水不溶性活性化合物的油性悬浮液,所述活性化合物被一种或多种保护性胶体所包围并适用于食品和动物饲料成分或者适用于药品和化妆品,条件是所述油性悬浮液不含水溶性维生素。
21.如权利要求20的油性悬浮液,其中含有作为分散相的适用于食品和动物饲料成分或者适用于药品和化妆品的至少一种水溶性、少量水溶性或水不溶性活性化合物的固体制品,它是通过如下方法获得的:
a)将上述活性化合物中至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将蛋白质保护性胶体与活性化合物一起从分散体中絮凝出来,和
c)将絮凝的固体从水和附加使用的任意溶剂中分离出来,接着将它们转变成干粉。
22.如权利要求20或21的油性悬浮液,以油性悬浮液的总量为基础计,活性化合物的含量为0.1-50%wt。
23.如权利要求20-22任一项的油性悬浮液,其含有至少一种选自以下的类胡萝卜素作为活性化合物:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。
24.如权利要求23的含类胡萝卜素的油性悬浮液,水分含量为0.1-6%wt。
25.如权利要求23或24的含类胡萝卜素的油性悬浮液,其中固体相的平均细度是0.1-100μm。
26.如权利要求23-25任一项的含类胡萝卜素的油性悬浮液,其中至少一种类胡萝卜素以非晶形或者部分非晶形形式存在。
27.如权利要求23-26任一项的含类胡萝卜素的油性悬浮液,其中含有至少一种蛋白质保护性胶体或改性淀粉作为保护性胶体。
28.一种油性悬浮液,它含有作为分散相的至少一种水溶性、少量水溶性或水不溶性的活性化合物的固体制品,其适用于食品和动物饲料成分或适用于药品和化妆品,它们可通过如下获得:
a)将上述活性化合物中至少一种溶于或分散于蛋白质保护性胶体的含水分子分散体或胶体分散体中,
b)将蛋白质保护性胶体与活性化合物一起从分散体中絮凝出,
和
c)将絮凝的固体从水和附加使用的任意溶剂中分离出来,接着将它们转变成干粉。
29.如权利要求28的油性悬浮液,以油性悬浮液的总量计,活性化合物的含量是0.1-50%wt。
30.如权利要求28或29的油性悬浮液,它含有作为活性化合物的至少一种选自以下的类胡萝卜素:虾青素、β-胡萝卜素、β-阿朴-8’-胡萝卜素醛、β-阿朴-8’-胡萝卜素酸乙酯、斑螯黄质、柠黄质、海胆酮、叶黄素、番茄红素和玉米黄质。
31.一种生产权利要求23的含类胡萝卜素的油性悬浮液的方法,包括:
a)在至少一种油中将含有用一种或多种保护性胶体包围的至少一种类胡萝卜素的干粉研磨至平均细度为0.1-100μm,或者
b)在没有使用连续相的情况下将一种或多种保护性胶体包围的至少一种类胡萝卜素的干粉研磨至平均细度为0.1-100μm,然后将研碎的颗粒悬浮于至少一种油中,或者
c)将含类胡萝卜素的悬浮液研磨至平均细度为0.1-100μm,该悬浮液含有作为固相的至少一种被一种或多种保护性胶体包围的类胡萝卜素,并且含有作为分散介质的水或者水与水混性溶剂的混合物,然后将该固相从水或水/溶剂混合物中分出,并将所得研碎颗粒悬浮于至少一种油中。
32.如权利要求31的方法,其中油是20℃下为液体的食用油。
33.如权利要求31的方法,其中油是20℃下为固体的硬脂。
34.如权利要求20-30任一项的油性悬浮液的用途,用于生产食品补充物和作为动物饲料、食品、药品和化妆品的添加剂。
35.如权利要求34的用途,其中油性悬浮液含有类胡萝卜素。
36.如权利要求34或35的用途,作为动物营养的饲料添加剂。
37.如权利要求36的用途,用于掺入饲料颗粒中。
38.如权利要求36的用途,用于涂敷到食品颗粒上。
39.如权利要求38的用途,其中饲料颗粒是在减压下用油性悬浮液装料的。
40.含有权利要求20-30任一项的油性悬浮液的食品补充物、动物饲料、食品或药品或化妆品。
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DE10059213.9 | 2000-11-29 | ||
DE10059213A DE10059213A1 (de) | 2000-11-29 | 2000-11-29 | Verfahren zur Herstellung fester Zubereitungen wasserunlöslicher oder schwer wasserlöslicher Wirkstoffe |
DE10129713A DE10129713A1 (de) | 2001-06-22 | 2001-06-22 | Verfahren zur Herstellung fester Zubereitungen wasserlöslicher, schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe |
DE10129713.0 | 2001-06-22 |
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CN01130192A Pending CN1364426A (zh) | 2000-11-29 | 2001-11-29 | 水溶性、少量水溶性或水不溶性活性化合物固体制品的生产 |
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US (1) | US7105176B2 (zh) |
JP (1) | JP2002255931A (zh) |
KR (1) | KR100760764B1 (zh) |
CN (1) | CN1364426A (zh) |
AU (1) | AU783606B2 (zh) |
BR (1) | BR0105753A (zh) |
CA (1) | CA2363823A1 (zh) |
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CN100459968C (zh) * | 2003-09-15 | 2009-02-11 | 巴斯福股份公司 | 包含2,4,6-三苯胺基-对-(碳-2′-乙基己基-1′-氧基)-1,3,5-三嗪和二乙氨基羟基苯甲酰基苯甲酸己基酯的混合物的粉末制剂 |
CN101291598B (zh) * | 2005-10-21 | 2012-10-31 | 帝斯曼知识产权资产管理有限公司 | 具有高生物利用度的脂溶性活性成分的新颖制剂 |
CN101415395B (zh) * | 2006-03-29 | 2012-02-08 | 富士胶片株式会社 | 酪蛋白纳米粒子 |
CN102665664A (zh) * | 2009-12-21 | 2012-09-12 | 富士胶片株式会社 | 美发产品的制备方法 |
CN102665664B (zh) * | 2009-12-21 | 2013-08-28 | 富士胶片株式会社 | 美发产品的制备方法 |
CN107708436A (zh) * | 2015-06-12 | 2018-02-16 | 帝斯曼知识产权资产管理有限公司 | 包含胭脂树素的酸稳定饮料 |
CN111867566A (zh) * | 2018-03-15 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 包含维生素a的挤出物 |
CN112137974A (zh) * | 2020-10-09 | 2020-12-29 | 迪沙药业集团有限公司 | 一种罗红霉素分散片及其制备方法 |
CN112137974B (zh) * | 2020-10-09 | 2022-06-17 | 迪沙药业集团有限公司 | 一种罗红霉素分散片及其制备方法 |
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KR100760764B1 (ko) | 2007-10-04 |
AU783606B2 (en) | 2005-11-17 |
US7105176B2 (en) | 2006-09-12 |
KR20020042467A (ko) | 2002-06-05 |
CA2363823A1 (en) | 2002-05-29 |
AU9514601A (en) | 2002-05-30 |
JP2002255931A (ja) | 2002-09-11 |
US20020110599A1 (en) | 2002-08-15 |
BR0105753A (pt) | 2002-07-02 |
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