CN1678674A - 环糊精颗粒 - Google Patents
环糊精颗粒 Download PDFInfo
- Publication number
- CN1678674A CN1678674A CNA038210657A CN03821065A CN1678674A CN 1678674 A CN1678674 A CN 1678674A CN A038210657 A CNA038210657 A CN A038210657A CN 03821065 A CN03821065 A CN 03821065A CN 1678674 A CN1678674 A CN 1678674A
- Authority
- CN
- China
- Prior art keywords
- oil
- cyclodextrin
- cellulose
- seasonings
- granule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 77
- 239000002245 particle Substances 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 9
- 235000011194 food seasoning agent Nutrition 0.000 claims description 55
- 239000004278 EU approved seasoning Substances 0.000 claims description 54
- -1 Natvosol Polymers 0.000 claims description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- 239000008187 granular material Substances 0.000 claims description 42
- 235000013599 spices Nutrition 0.000 claims description 33
- 239000007921 spray Substances 0.000 claims description 32
- 238000002156 mixing Methods 0.000 claims description 26
- 229920002678 cellulose Polymers 0.000 claims description 23
- 239000001913 cellulose Substances 0.000 claims description 23
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000005469 granulation Methods 0.000 claims description 13
- 230000003179 granulation Effects 0.000 claims description 13
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 12
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 12
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 12
- 238000005516 engineering process Methods 0.000 claims description 12
- 235000013305 food Nutrition 0.000 claims description 11
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 10
- 239000001116 FEMA 4028 Substances 0.000 claims description 9
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- 238000002360 preparation method Methods 0.000 claims description 7
- 238000010899 nucleation Methods 0.000 claims description 5
- 230000006911 nucleation Effects 0.000 claims description 5
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- 239000001856 Ethyl cellulose Substances 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
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- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000796 flavoring agent Substances 0.000 abstract description 7
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- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 10
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- 239000000463 material Substances 0.000 description 9
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 8
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- 239000007788 liquid Substances 0.000 description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 5
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 5
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetic acid ester Natural products CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 5
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- MQFGIUKCEOGIGS-UHFFFAOYSA-N CC(C)C1=CCC(=C)C1C Chemical compound CC(C)C1=CCC(=C)C1C MQFGIUKCEOGIGS-UHFFFAOYSA-N 0.000 description 4
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- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
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- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明涉及含有芳香和香味物质的环糊精颗粒,该环糊精颗粒含有纤维素醚并具有50~100μm范围的粒径,并涉及含有所述颗粒的产品,以及其生产方法和在食品、药品和日用品中的用途。
Description
本发明涉及含调味剂和/或香料的环糊精颗粒,该颗粒含有纤维素醚且具有50-1000μm范围内的粒径,还涉及含有这些颗粒的产品,以及其生产方法和在食品、药品和日用品中的用途。
环糊精是通过α-1,4-键连接形成环状分子的葡萄糖苷单元的低聚物。根据结构单元的数量,在α-(6结构单元),β-(7结构单元)和γ-(8结构单元)环糊精之间加以区别。它们通常由淀粉通过酶法工艺制得。环糊精的环状结构允许在分子水平上形成包合物。可根据调味剂的几何形状和极性形成完善程度不同的包合物。
调味剂大多是挥发性化合物,由于蒸发或氧化导致在储存或加工操作期间表现出高损耗率,例如在食品工业中。在环糊精复合物中,可保护调味剂避免这些损耗。
调味剂和香料,或者调味剂和香料的混合物,通常是挥发性的,大多为液态物质或这些物质的复杂混合物。通常通过喷雾干燥来包封这些物质或物质混合物,然而该方法仅产生相对精细的不规则结构的颗粒。
调味剂和/或香料的环糊精包合物的许多生产方法是公知的。
这些方法包括将环糊精溶液、悬浮液或浆料(通常在水中)和调味剂和/或香料混合。依靠调味剂和/或香料的极性,从而在多数情况下得到两相混合物。因此,应用高剪切力,例如通过搅拌或捏合来加速该过程。多数情况下,随该步骤之后为干燥步骤,例如喷雾、冷冻或流化床干燥。
根据公知的现有技术,无需另外的添加剂,通过喷雾干燥含水调味剂/环糊精包合物的操作生成非常细的颗粒。
EP-A 392 608说明了一种生产粉状的环糊精复合物的方法,该环糊精复合物的粒径小于12μm,优选小于5μm。在其说明书中,采用例如喷雾干燥和冷冻干燥的方法。
小粒径对于这些包合物的使用是不利的。精细分离的环糊精复合物在水中很难被分散,并且因此降低了溶解速度。此外,当将小的(通常<10μm=环糊精颗粒用在主要含有粒径为50-500μm的组分的干燥混合物中时,存在析出风险。
小粒径具有的另一不利之处在于流动性通常被降低和容易形成粉尘。
因为这些原因,环糊精复合物颗粒具有至少50μm的粒径是有利的。
在喷雾干燥期间,一部分调味剂和/或香料残留在颗粒表面上。该所谓的表面油导致氧化稳定性降低并且还进一步降低了流动性。最小化表面油量是适宜的。
DE-A 31 05 666公开了一种方法,其中借助于在捏合机中将粘合剂加入环糊精复合物的混合物中,并且随后干燥和研磨,来生产具有500-1000μm粒径的颗粒。
这种捏合工艺的缺点是成品颗粒中高比例的表面油。另外,从生产成本的观点来看,采用多个工艺步骤(捏合、干燥、研磨、筛分)是不利的。
在EP-A 1 064 856中,公开了含有碳水化合物和/或多羟基化合物的具有100-400μm范围尺寸的颗粒。这里所公开的生产这些颗粒的多步工艺包括除了喷雾干燥外的其它步骤。在这些步骤之一中,使加工中形成的较小颗粒再循环,从而使其通过集聚生长到所述粒径范围。这些颗粒的缺点是其低磨损稳定性和其表面油含量。
本发明的目的在于提供含有调味剂和/或香料的环糊精颗粒,该颗粒具有至少50μm的尺寸,该颗粒改善了上述现有技术的缺点,并且提供生产该颗粒的尽可能简单的方法。窄粒径分布将是额外的优点。
因此,本发明提供含有调味剂和/或香料的环糊精颗粒,该环糊精颗粒具有在50-1000μm范围内的粒径并含有纤维素醚,同时该环糊精颗粒可通过单级流化床工艺由喷雾混合物得到,其中气体入口温度为80-180℃和气体出口温度为40-95℃
本发明还提供一种生产环糊精颗粒的方法,其特征在于将包含至少一种环糊精,至少一种调味剂和/或香料和至少一种纤维素醚的含水喷雾混合物加入到单级流化床设备中。
本发明还涉及含有根据本发明的环糊精颗粒的产品和根据本发明的环糊精颗粒在食品、药品和日用品中的应用。
可以使用本身公知的造粒工艺由喷雾混合物生产颗粒。根据本发明,适合的工艺为单步的,也就是说将喷雾混合物供应到单个装置,当该混合物离开该装置时,生产完成并且可得到成品环糊精颗粒。与多步工艺相比较,在单步工艺中没有形成中间体。
所述的颗粒可以通过连续流化床喷雾造粒来生产,例如根据EP-A 163 836,或者通过间歇流化床喷雾造粒来生产,例如根据EP-A 70 719。也可以采用如在WO-A97/16078中的在间歇操作的传统流化床旋转造粒机中生产调味剂颗粒的方法。
该工艺优选为连续的。连续工艺更适于工业生产并表现出短的停留时间。以同样的原料吞吐量,在连续流化床喷雾造粒工艺情况下的床容积要低于间歇工艺的情况。在连续流化床喷雾造粒中只有少量的颗粒核被喷出而不是允许所有的颗粒核同时生长,并且一旦达到所需的粒径,它们就立即被排出,例如通过筛分器。根据本发明生产的含有调味剂和/或香料的包封环糊精颗粒表现出低的粒径分布;此外,可以选择性除去所需尺寸的颗粒(微粒)。
在本发明的范围内,流化床优选具有小的床高。优选为3-50cm,尤其优选为5-20cm。
通过连续流化床喷雾造粒,从喷雾混合物得到自由流动的、低粉尘的颗粒。理想地,成核、干燥、成形和选择性排出已达到所需粒径的颗粒的基本操作在造粒装置中同时进行。
连续流化床喷雾造粒(Chemie-Ingenieur-Technik,62 nd(1990),822-834页)的基本原理已通过许多不同方式实现。尤其要对外部成核和内部成核方式加以区别,在外部成核方式中核从外部的筛分器、研磨装置或其它固体贮存器计量供应到该流化床。
在本发明的范围内,优选有内部核供应的工艺。这样的工艺公开在例如EP-A 163836中。这种造粒装置还具有自动调节机构来调节粒径并从而表现出最小的停留时间。
喷雾混合物可从底部、从侧面或从顶部被喷入流化床。许多不同方式都可用于从废气中分离夹带的固体,其中不同方式的差异在于分离方法(例如,旋风分离或过滤)或者在于分离的位置(造粒装置的内部或外部)。
最后,例如在EP-A332 031中所述的筛分器优选用来排出颗粒。筛分器具有仅使粗糙颗粒能够离开流化床的作用。残留颗粒保留在该流化床中直到它们也达到了所需的粒径。
为了生产根据本发明的颗粒,首先要制备含水喷雾混合物。除水之外,该喷雾混合物还包括至少一种环糊精、调味剂和/或香料和至少一种纤维素醚。
在一个工艺步骤内,在流化床装置中,从该喷雾混合物生产根据本发明的颗粒,粒径大于或等于50μm。
根据本发明的颗粒具有从50μm到1000μm的粒径。优选颗粒具有从70μm到500μm的粒径,尤其优选从100到300μm。
关于粒径的数据基于颗粒直径和来自累积分布曲线。这些累积分布曲线表明累积分布Q3(x)对颗粒直径x的相关性。累积分布Q3(x)是所有具有小于或等于x的直径的颗粒的标准化总量。粒径x50,3是在累积分布Q3(x)=0.5时的粒径。除非以其他方式表征,在本文中涉及粒径的数据基于粒径x50,3。下标3指所测量的量的类型是体积(Ullmanns Encyklopdie der technischen Chemie,卷2,Verfhrenstechnik I,第四版,Verlag Chemie,Weinheim,1972,p.24-34)。
通过体积分布来测量粒径可以由激光衍射法进行(例如,使用MalvernInstruments Ltd.,Malvern,UK的Master SizerMSS Longbench)。
合适的环糊精为α-、β-、γ-和取代的环糊精。α-、β-、γ-环糊精或其混合物是有利的,优选为β-环糊精。在优选实施方案中,喷雾混合物的环糊精成分仅由β-环糊精组成。
喷雾混合物中的环糊精量从5到50wt.%是有利的,优选为10-40wt.%,尤其优选为15-30wt.%。
喷雾混合物中的水量从40到95wt.%是有利的,优选为50-90wt.%,尤其优选为60-80wt.%。
喷雾混合物中的调味剂和/或香料的量从0.0005到15wt.%是有利的,优选为0.1-10wt.%,尤其优选为0.25-5wt.%。
喷雾混合物含有纤维素醚形式的粘合剂作为造粒助剂。纤维素醚优选选自甲基纤维素、乙基纤维素、丙基纤维素、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、羧甲基羟乙基纤维素和乙基羟乙基纤维素,尤其优选为羧甲基纤维素(CMC)。
喷雾混合物中的纤维素醚含量优选为从0.1到6wt.%,尤其优选为从0.2到2wt.%。干燥颗粒优选含0.5-10wt.%,尤其优选为从2到4.5wt.%的纤维素醚。
纤维素醚具有15-200,000mPas的粘度是有利的;优选具有1000-50,000mPas粘度,尤其优选具有5000-15,000mPas粘度。粘度数据基于20℃时2wt.%的水溶液。
所用的测量系统是具有40mm直径和4°锥角的锥/板系统。剪切速率为1s-1,温度为20℃。例如,可使用CVO 120流变仪(Bohlin Instruments GmbH,Pforzheim)来确定粘度。
根据依照本发明的工艺,调味剂和/或香料在成品环糊精颗粒中的含量为0.01-30wt.%,优选为1-15wt.%并且尤其优选为5-10wt.%。
从文献可知确定负载(loading)和表面油的方法。在现有情况下,确定调味剂和/或香料在成品环糊精颗粒中的含量以确定负载和表面油的方法类似于J.Agrc.Food Chem,1998,46,1494-1499中的方法。在此所述的方法仅对在提取中所用的溶剂有变动。使用乙酸乙酯代替正己烷来确定负载,并使用正戊烷和二乙醚的2∶1混合物(体积分数)代替正己烷来确定表面油含量。负载和表面油含量以wt.%给出。
已发现可作为根据本发明的环糊精颗粒组分的调味剂和/或香料的例子,例如,在S.Arctander,Perfume and Flavor Chemicals,卷I和II,Montclair,N.J.,1969,Selvstverlag或K.Bauer,D.Garbe和H.Surburg,Common Fragrance and FlavorMaterials,第4版,Wiley-VCH,Weinheim 2001。
可详细提及的有:源自天然原料的提取物例如精油,浸膏,净油,树脂,香树脂,香脂,酊剂,举例来说有:琥珀酊;阿米香树油;当归籽油;当归根油;茴香籽油;缬草油;罗勒油;树苔净油;月桂油;苦艾油;安息香树脂;香柠檬油;蜂蜡净油;桦木焦油;苦杏仁油;香旱芹油;布枯油;卡鲁瓦油;刺柏油;菖蒲油;樟脑油;依兰油;小豆蔻油;卡藜油;肉桂油;金合欢净油;海狸香净油;雪松叶油;雪松油;岩蔷薇油;香茅油;柠檬油;苦配巴香脂;苦配巴香脂油;芫荽油;广木香根油;枯茗油;柏树油;印蒿油;莳萝草油;莳萝子油;eau de brouts absolute;橡苔净油;榄香脂油;龙蒿油;柠檬桉叶油;桉树油;小茴香油;云杉针叶油;格蓬油;格蓬树脂;天竺葵油;葡萄柚油;愈创木油;羯布罗香胶;羯布罗香油;永久花净油;永久花油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;白菖(蒲)油;蓝春黄菊油;罗马甘菊油;胡萝卜籽油;卡藜油;松针油;薄荷油;葛缕子油;岩蔷薇油;岩蔷薇净油;岩蔷薇树脂;杂薰衣草净油;杂薰衣草油;熏衣草净油;熏衣草油;柠檬草油;圆叶当归油;蒸馏白柠檬油;压榨白柠檬油;沉香油;山苍子油;月桂叶油;肉豆蔻衣油;马郁兰油;橘子油;massoirinde oil;含羞草净油;黄葵籽油;黄葵酊;鼠尾草油;肉豆蔻油;没药净油;没药油;桃金娘油;丁香叶油;丁香花油;橙花油;乳香净油;乳香油;愈伤草油;橙花净油;橙油;牛至油;玫瑰草油;广藿香油;紫苏子油;秘鲁香脂油;欧芹叶油;欧芹子油;苦橙叶油;胡椒薄荷油;胡椒油;多香果油;松油;poley oil;玫瑰净油;蔷薇木油;玫瑰油;迷迭香油;达尔马提亚鼠尾草油;西班牙鼠尾草油檀香油;芹菜子油;穗熏衣草油;八角茴香油;安息香油;万寿菊油;杉针油;茶树油;松节油;百里香油;吐鲁香脂;香豆净油;晚香玉净油;香子兰浸液;紫罗兰叶净油;马鞭草油;岩兰油;刺柏油;葡萄子油;苦艾油;冬青油;衣兰油;神香草油;灵猫香净油;肉桂叶油;肉桂皮油;以及其馏分,或从其中分离出的成分;
个别香料选自烃类,例如:3-蒈烷;α-蒎烯;β-蒎烯;α-松油烯;γ-松油烯;对-伞花烃(异丙基甲苯);甜没药醇;莰烯;石竹烯;柏木烯;金合欢烯;苧烯;长叶烯;月桂烯;罗勒烯;朱栾倍半萜;(E,Z)-1,3,5-十一碳三烯;
脂肪醇,例如:己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基庚醇,2-甲基辛醇;(E)-2-己烯醇;(E)-和(Z)-3-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3/4-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛-2-醇;9-癸烯醇;10-十一(碳)烯醇;4-甲基-3-癸烯基-5-醇;脂肪族醛和它们的1,4-二氧环烯-2-酮,例如:己醛;庚醛;辛醛;壬醛;癸醛;十一醛;十二醛;十三醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一烯醛;(E)-4-癸烯醛;2-十二碳烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙基乙缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅基氧乙醛;
脂肪族酮及其肟,例如:2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3-庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;脂肪族含硫化合物,例如:3-甲基硫己醇;3-甲基硫己基乙酸酯;3-巯基己醇;3-巯基己基乙酸酯;3-巯基己基丁酸酯;3-乙酰基硫己基乙酸酯;1-孟烯-8-硫醇;
脂肪族腈,例如:2-壬烯酸腈;2-三癸烯酸腈;2,12-三癸二烯酸腈;3,7-二甲基-2,6-辛二烯酸腈;3,7-二甲基-6-辛烯酸腈;
脂肪族羧酸及其酯,例如:(E)和(Z)-3-己烯基甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;3,5,5-三甲基-己基乙酸酯;3-甲基-2-丁烯基乙酸酯;(E)-2-己烯基乙酸酯;(E)和(Z)-3-己烯基乙酸酯;乙酸辛酯;3-辛基乙酸酯;1-辛烯-3-基乙酸酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)和(Z)-3-己烯基异丁酸酯;巴豆酸己酯;异缬草酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛烯酸甲酯;2-壬烯酸甲酯;2-异戊基氧乙酸烯丙酯;3,7-二甲基-2,6-辛二烯酸甲酯;
非环萜烯醇,例如:香茅醇;香叶醇;橙花醇;沉香醇;lavadulol;橙花叔醇;金合欢醇;四氢里哪醇;四氢香叶醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛烯-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛三烯-3-醇;2,6-二甲基-2,5,7-辛三烯-1-醇;和它们的甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、tiglinates、3-甲基-2-丁烯酸酯;
非环萜烯醛和酮,例如:香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一烯醛;香叶基丙酮;和香叶醛的二甲基和二乙基缩醛、橙花醛、7-羟基-3,7-二甲基辛醛。
环萜烯醇,例如:薄荷醇、异蒲勒醇;α-萜品醇;萜品醇-4;孟-8-醇;孟-1-醇;孟-7-醇;冰片醇;异冰片醇;氧化芳樟醇;诺卜醇;雪松醇;龙涎醇;岩兰草醇;愈创醇;和它们的甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、tiglinates、3-甲基-2-丁烯酸酯;
环萜烯醛和酮,例如:薄荷酮;异薄荷酮;8-巯基孟-3-酮;香芹酮;樟脑;葑酮;α-紫罗(兰)酮;β-紫罗(兰)酮;α-n-甲基紫罗兰酮;β-n-甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-鸢尾酮;α-二氢大马酮;β-二氢大马酮;β-二氢大马烯酮;δ-二氢大马酮;γ-二氢大马酮;1-(2,4,4-三甲基-2-环己-1-烯基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-亚甲基萘甲胺-8(5H)-酮;香柏酮;二氢香柏酮;α-甜橙醛;β-甜橙醛;乙酰基雪松油(甲基柏木酮);
环醇,例如:4-叔丁基环己醇;3,3,5-三甲基-环己醇;3-异莰基环己醇;2,6,9-三甲基-Z2,Z5,E9-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;
环脂族醇,例如:α-3,3-三甲基环己基甲醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;2-乙基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-戊烯-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊烯-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
环醚和环脂醚,例如:桉树脑;甲基柏木醚;环十二烷基甲基醚;(乙氧甲氧基)环十二烷;α-环氧柏木烯;3a,6,6,9a-四甲基十二氢萘酚[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘酚[2,1-b]呋喃;1,5,9-三甲基-13-氧杂二环[10.1.0]-十三烷基-4,8-二烯;玫瑰醚;2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二氧杂环己烷;
环酮,例如:4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺式-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环十五烷酮;3-甲基-5-环十五烷酮;3-甲基环十五烷酮;4-(1-乙氧乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六烷基-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮;5-环十六烷基-1-酮;8-环十六烷基-1-酮;9-环十七烷基-1-酮;环十五烷酮;
环脂醛,例如:2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基-环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
环脂酮,例如:1-(3,3-二甲基环己基)-4-戊烯-1-酮;1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘基甲基酮;甲基2,6,10-三甲基-2,5,9-环十二烷三烯酮;叔丁基-(2,4-二甲基-3-环己烯-1-基)酮;
环醇的酯,例如:2-叔丁基环己基乙酸酯;4-叔丁基环己基乙酸酯;2-叔戊基环己基乙酸酯;4-叔戊基环己基乙酸酯;十氢-2-萘乙酸酯;3-戊基四氢-2H-吡喃-4基乙酸酯;十氢-2,5,5,8a-四甲基-2-萘乙酸酯;4,7-甲酰氧3a,4,5,6,7,7a-六氢-5-或-6-茚基乙酸酯;4,7-甲酰氧3a,4,5,6,7,7a-六氢-5-或-6-茚基丙酸酯;4,7-甲酰氧3a,4,5,6,7,7a-六氢-5-或-6-茚基异丁酸酯;4,7-甲酰氧八氢-5-或-6-茚基乙酸酯;
环脂族羧酸酯,例如:3-环己基丙酸烯丙酯;环己基氧乙酸烯丙酯;甲基二氢茉莉酮酸酯;甲基茉莉酮酸酯;甲基2-己基-3-氧环戊烯羧酸酯;乙基-2-乙基-6,6-二甲基-2-环己烯羧酸酯;乙基2,3,6,6-四甲基-2-环己烯羧酸酯;乙基-2-甲基-1,3-二氧戊环2-乙酸酯;
芳烃,例如:苯乙烯和二苯基甲烷;
芳脂族醇,例如:苯甲醇,1-苯乙醇;2-苯乙醇;3-苯丙醇;2-苯丙醇;2-苯氧乙醇;2,2-二甲基-3-苯丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯乙醇;1,1-二甲基-3-苯丙醇;1-乙基-1-甲基-3-苯丙醇;2-甲基-5-苯戊醇;3-甲基-5-苯戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基苯甲醇;1-(4-异丙基苯基)乙醇;
芳脂族醇和脂肪族羧酸的酯,例如:乙酸苯甲酯;丙酸苯甲酯;异丁酸苯甲酯;异戊酸苯甲酯;2-苯乙基乙酸酯;2-苯乙基丙酸酯;2-苯乙基异丁酸酯;2-苯乙基异戊酸酯;1-苯乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯乙基乙酸酯;α,α-二甲基苯乙基丁酸酯;乙酸肉桂酯;异丁酸2-苯氧基乙酯;乙酸4-甲氧基苄酯;芳脂型醚,例如:2-苯乙基甲基醚;2-苯乙基异戊基醚;2-苯乙基1-乙氧基乙基醚;苯乙醛二甲基乙缩醛;苯乙醛二乙基乙缩醛;hydratropaaldehyde二甲基乙缩醛;苯乙醛甘油乙缩醛;2,4,6-三甲基-4-苯基-1,3-二氧杂环己烷;4,4a,5,9b-四氢茚-[1,2-d]-m-二氧杂环己烯;4,4a,5,9b-四氢-2,4-二甲基茚[1,2-d]-m-二氧杂环己烯;
芳族和芳脂族醛,例如:苯甲醛;苯乙醛;3-苯丙醛;hydratropaaldehyde;4-甲基苯甲醛;4-甲基苯乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧苯基)丙醛;
芳族和芳脂族酮,例如:苯乙酮;4-甲基-苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟苯基)-2-丁酮;1-(2-萘基)乙烯酮;苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲基酮;6-叔丁基-1,1-二甲基-4-茚满基甲基酮;1-[2,3-二氢-1,1,2,3-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙烯酮;5’,6’,7’,8’-四氢-3’,5’,5’,6’,8’,8’-六甲基-2-萘乙酮;
芳族和芳脂族羧酸和它们的酯,例如:苯甲酸;苯乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄酯;甲基苯基乙酸酯;乙基苯基乙酸酯;香叶基苯基乙酸酯;苯乙基苯基乙酸酯;甲基肉桂酸酯;乙基肉桂酸酯;苄基肉桂酸酯;苯乙基肉桂酸酯;肉桂酸肉桂酯;苯氧基乙酸烯丙酯;水杨酸甲酯;水杨酸异戊酯;水杨酸己酯;水杨酸环己酯;水杨酸顺式-3-己烯酯;水杨酸苄基酯;水杨酸苯乙酯;甲基-2,4-二羟基-3,6-二甲基苯甲酸酯;乙基-3-苯基缩水甘油酯;乙基-3-甲基-3苯基缩水甘油酯;
含氮芳香族化合物,例如:2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基乙酰苯;肉桂酸腈;5-苯基-3-甲基-2-戊烯酸腈;5-苯基-3-甲基戊烯酸腈;甲基邻氨基苯甲酸酯;甲基-N-甲基邻氨基苯甲酸酯;甲基邻氨基苯甲酸酯和7-羟基-3,7-二甲基辛醇的Schiff碱;2-甲基-3-(4-叔丁基苯基)丙醇;2,4-二甲基-3-环己烯甲醛;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;吲哚;粪臭素(scatole);2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;
苯酚,苯基醚和苯基酯,例如:草蒿脑;茴香脑;丁子香酚;丁子香甲基醚;异丁子香酚;异丁子香基甲基醚;麝香草酚;香芹酚;二苯醚;β-萘基甲基醚;β-萘基乙基醚;β-萘基异丁基醚;1,4-二甲氧基苯;丁子香乙酯;2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;对甲酚苯基乙酸酯;
杂环化合物,例如:2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
内酯,例如:1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一内酯;1,4-十二内酯;1,5-癸内酯;1,5-十二内酯;1,15-十五内酯;顺式和反式-11-十五-1,15-内酯;顺式和反式-12-十五-1,15-内酯;1,16-十六内酯;9-十六-1,16-内酯;10-氧-1,16-十六内酯;11-氧-1,16-十六内酯;12-氧-1,16-十六内酯;乙烯基-1,12-十二烷基-二内酯;乙烯基-1,13-十三烷基-二内酯;香豆素;2,3-二氢香豆素,八氢香豆素。
除了所有上述物质外,可以作为环糊精颗粒组分的调味剂的例子特别是下面类别的物质:脂族酯(饱和与不饱和的),如丁酸乙酯、己酸烯丙酯;芳香酯,如乙酸苯甲酯、水杨酸甲酯;有机脂肪族酸(饱和与不饱和的),如丁酸、乙酸、己酸;有机芳香族酸;脂肪族醇(饱和与不饱和的),如乙醇、丙二醇、辛烯醇、3-辛烯醇、顺式-3-己烯醇;环醇,如薄荷醇;芳醇,如苄醇;脂肪族醛(饱和与不饱和的),如乙醛、壬二烯醛;芳族醛,如苯甲醛;酮,如薄荷酮;环醚,如4-羟基-5-甲基呋喃酮;芳族醚,如对甲氧基苯甲醛、愈创木酚;苯酚醚,如甲氧基乙烯基苯酚;缩醛,如乙醛缩二乙醇(acetaldehyde diethylacetal);内酯,如γ-癸内酯;萜烯,如柠檬烯、沉香醇、萜品烯、萜品醇、柠檬醛(牻牛儿醛和橙花醛);含硫化合物,如二甲基硫化物、甲基硫醇、乙基硫醇、异硫氰酸烯丙酯、甲基呋喃硫醇、二糠基二硫化物;或吡嗪,如甲基吡嗪、乙酰基吡嗪。
由于表面油的含量极低,根据本发明的环糊精颗粒尤其适于气味强烈的,易挥发的,易氧化的,难以计量的、难以处理的和/或有刺激性的物质的包封。相关的例子有:乙醛,异硫氰酸烯丙酯,柠檬烯,顺式-3-己烯醇,柠檬醛,甲基乙基吡嗪或甲基硫醇。
根据本发明的环糊精颗粒可进一步包括具有生理营养活性(营养科学)的物质或物质的混合物。有关例子包括泛醇,泛酸,基本脂肪酸,维生素A及衍生物,胡罗卜素,维生素C(抗坏血酸),维生素E(生育酚)及衍生物,维生素B和D族,例如维生素B6(烟碱),维生素B12,维生素D1,维生素D3,维生素F,叶酸,生物素,氨基酸,元素镁,硅,磷,钙,锰,铁或铜的化合物,辅酶Q10,不饱和脂肪酸,ω-3-脂肪酸,多不饱和脂肪酸,γ-亚麻酸,油酸,二十碳五烯酸(EPA),二十二碳六烯酸(DHA)和其衍生物,甜没药醇,氯霉素,咖啡因,辣椒素,前列腺素,麝香草酚,樟脑,植物和动物源提取物或其它产品,例如月见草油,琉璃苣油或醋栗籽油,鱼油,鳕鱼肝油,神经酰胺和类神经酰胺的化合物。植物提取物,例如,山金车,芦荟,须松罗,常春藤,刺荨麻,人参,指甲花,甘菊,万寿菊,迷迭香,鼠尾草,马尾或百里香。油类,如杏籽油,鳄梨油,巴巴苏棕油,棉子油,琉璃苣油,蓟油,花生油,γ-谷维素,玫瑰果油,大麻油,榛子油,醋栗籽油,霍霍巴油(JOJOBA OIL),樱仁油,鲑鱼油,亚麻子油,玉米油,夏威夷果油,杏仁油,月见草油,貂油,橄榄油,山核桃果油,桃仁油,阿月浑子果仁油,菜油,米糠油,蓖麻油,红花油,芝麻油,大豆油,向日葵油,茶树油,葡萄子油或麦胚芽油。
当然,根据本发明的环糊精颗粒可包括其它物质,例如:乳化剂,着色剂,抗氧化剂,稳定剂,紫外线吸收剂,维生素和在食品、个人护理、制药或香料工业中常用的其他成分。
例如,可如在EP-A 1 084 625中概述的或如在下文中说明的那样来制备喷雾混合物。
首先形成环糊精和调味剂的复合物。为此目的,必须使环糊精和调味剂至少部分地被溶入溶液。所用的溶剂是温度为10℃~90℃的水,优选为40℃~70℃,尤其优选为50℃~60℃。在调味剂有特别低的沸点或对热有高敏感性的情况下, 优选温度为15~30℃。
依靠调味剂和/或香料的极性,在多数情况下形成两相混合物。为加速该过程,根据本发明引入剪切力。剪切力的引入可通过例如搅拌或分散进行,其中转子-定子分散工具或高压均化器尤其适合该目的。
向调味剂和/或香料/环糊精复合物方向的平衡转移需要时间。根据本发明,在引入剪切力后,保持混合物的静置是有利的,可在4~25℃下冷却静置0.2~24小时,优选为在4~7℃下冷却静置8~16小时。
在敏感的调味剂和/或香料的情况下,优选将静置期缩短为在4~7℃下15~30分钟。
可在任何所需时间点进行喷雾混合物中纤维素醚的加入。这可在复合物形成之前,复合物形成期间,在复合物形成后但在低温储存之前,在低温储存期间或在低温储存后。也可以将环糊精粉末与纤维素醚混合并且然后仅加入水。纤维素醚的总量也可以被分成若干分量,也就是说可被分成几份,并在任何所需时间点加入。
在制备喷雾混合物时,所使用的物质可以任何所需顺序加入。例如,可将环糊精和纤维素醚混合,随后加入水并进行剧烈搅拌或分散。然后加入调味剂和/或香料并剧烈搅拌或分散混合物以及在低温下储存。可选择的顺序包括:首先剧烈混合水,纤维素醚和调味剂和/或香料,随后加入并分散环糊精。在另一变换方式的例子中,可将环糊精加入水中并剧烈搅拌。加入调味剂并分散。在随后的低温储存之后,将纤维素醚加入并通过搅拌或分散来使其散布。
优选在如EP-A 163 836中所公开的造粒设备中进行造粒。因此喷雾混合物的温度选择为调味剂或香料/环糊精复合物不会分解的温度。该温度通常为5~70℃,优选为10~40℃,尤其优选为20~30℃。
可使用例如空气,氮气,氩气或二氧化碳,优选为空气和氮气作为流化气体。流化气体的气体入口和气体出口温度将与讨论的特定喷雾混合物相匹配。气体入口温度为80~180℃,优选为100~140℃,尤其优选为120~130℃。气体出口温度为40~95℃,优选为45~70℃,尤其优选为50~60℃。
根据本发明的环糊精颗粒可用于许多产品中。它们可被用于食品和高档食品中,例如,用于糖果点心中,如:硬糖,口香糖,口腔清新剂,comprimates,硬奶糖,糖果和巧克力,烘焙食品如糕饼,华夫饼干和饼干,小吃,即食餐和其他即食产品(汤,调味汁,饮料粉末和颗粒,茶包,香辛料混合物)。该环糊精颗粒尤其适于热的,高温加热的,温热的,灭菌的或巴氏法灭菌的食品,例如,烧制食物(cateredmeals),油炸食品,薯条,调味panades,快餐,微波食物和腌制的水果及蔬菜。
医药产品可以是,例如,止咳糖浆,润喉或止咳糖,药剂粉末或颗粒。
日用品可以是,例如,个人护理产品,家用产品,烟草产品(如香烟),化妆品,洗涤和清洗剂,空气清新剂,纺织品或除味剂(如猫砂)。
个人护理用品可以是,例如,口腔护理产品,如牙膏,牙胶,牙霜,牙齿护理口香糖和嗽口水。
以下实施例解释本发明:
除非另有指明,所有量均为以重量计。
在本例中,保留率(以wt.%表示)应理解为在成品颗粒中的调味剂和/或香料的量与在喷雾混合物中所用的调味剂和/或香料的量的相对重量比。
实施例
实施例1:柠檬油精/环糊精颗粒
配方:
13,143g的饮用水
4000g的β-环糊精(Kleptoseβ-环糊精,Roquette)
431g的d-柠檬油精
133g的羧甲基纤维素(CMC)(Walocel CRT 10000 GA,Wolff Walsrode);20℃,1s-1下2%溶液的粘度:10,000mPas
将水加热至25℃,加入环糊精,该混合物使用Ultra Turrax T50 DPX混合3分钟。加入d-柠檬油精并进一步分散该混合物15分钟。
混合物在6℃存储6小时后,加入羧甲基纤维素并借助Ultra Turrax T50 DPX进行均质化。然后该混合物在20℃进一步静置15小时,随后送入流化床造粒设备。
将上述喷雾混合物在EP-A 163 836中公开类型的造粒设备(具有以下特征:流入基部直径:225mm,喷嘴:双喷嘴;分离排料:锯齿筛;过滤器:内管过滤器)中造粒。混合物的温度为35℃。为使床体内容物流化,空气以60kg/h的量被吹入。流化气体的进口温度为120℃。出口气体的温度为55℃。作为筛分气体的空气以1.5kg/h的量和34℃的温度被供入。造粒产量约为420g/h。获得平均粒径为131.7μm和堆积密度为470g/l的自由流动颗粒。该颗粒具有光滑表面和球形,主要为球状的几何形状。
因为过滤器的恒定压力损失和同样保持为常量的床体内容物,因此对于造粒过程假设为静态条件。
-负载:7.7%
-保留率:79.2%
-表面油:0.03%
-粒径分布(通过激光衍射;装置:Malvern Master SizerMSS Lonngench):
Q3(x)=0.1:x=75μm
Q3(x)=0.5:x=132μm
Q3(x)=0.9:x=196μm
-堆积密度:470g/l
实施例2:柠檬油精颗粒2
6385g的饮用水
2000g的β-环糊精
215.5g的d-柠檬油精
78g羧甲基纤维素(CMC),TyloseC 6000 G1,Clariant;20℃,1s-1下2%溶液的粘度:6000mPas
将水加热至50℃,加入环糊精,该混合物使用Ultra Turrax T50 DPX混合3分钟。加入d-柠檬油精并进一步分散该混合物15分钟。
混合物在20℃存储30分钟后,加入羧甲基纤维素并借助Ultra Turrax搅拌器进行均质化。
然后该混合物在6℃被进一步静置15小时和(储存),随后加入实施例1的流化床造粒设备中。流化气体的进口温度为125℃。出口气体的温度为49℃。造粒产量约为570g/h。获得平均粒径为165.8μm和堆积密度为460g/l的自由流动颗粒。该环糊精颗粒具有光滑表面和球形,主要为球状的几何形状。
-负载:8.4%
-保留率:86.4%
-表面油:0.04%
-粒径分布(激光衍射):
Q3(x)=0.1:x=89μm
Q3(x)=0.5:x=166μm
Q3(x)=0.9:x=272μm
-堆积密度:460g/l
实施例3:胡椒薄荷味颗粒
6385g的饮用水
2000g的β-环糊精
215.5g的薄荷油调味剂
62g的羧甲基纤维素(CMC)(Walocel CRT 10000 GA,Wolff Walsrode);20℃,1s-1下2%溶液的粘度:10,000mPas
将水加热至50℃,加入环糊精,该混合物使用Ultra Turrax T50 DPX混合3分钟。加入薄荷油调味剂后,用Ultra Turrax T50 DPX进一步彻底混合该混合物15分钟。用Ultra Turrax加入并溶解CMC。
与实施例2类似地进行储存和进一步的制备;造粒产量为600g/h。得到自由流动的颗粒。
-负载:8.8%
-保留率:87%
-粒径分布(通过激光衍射;装置:Malvern Master SizerMSS Longbench):
Q3(x)=0.1:x=103μm
Q3(x)=0.5:x=182μm
Q3(x)=0.9:x=296μm
-表面油:0.03%
-堆积密度:400g/l
实施例4:牛肉味颗粒
6385g的饮用水
2000g的β-环糊精
200g的牛肉调味剂
95g的甲基纤维素(MC),MethocelA4M FG,道康宁化学公司;20℃,1s-1下2%溶液的粘度:4000mPas
在将环糊精加入水(10℃)中后,该混合物使用Ultra Turrax T50 DPX混合3分钟。加入牛肉调味剂并将该混合物进一步分散40分钟。在该混合物在20℃被静置30分钟后,加入甲基纤维素并用Ultra Turrax搅拌器进行均质化。
与实施例1类似地进行储存和进一步的制备。
实施例5-14
喷雾混合物的成分;所用的涉及用量的数据以克计。
5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | |
水 | 6200 | 6000 | 6000 | 6385 | 6385 | 6500 | 6500 | 6385 | 6800 | 6900 |
α-环糊精 | 660 | 2000 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
β-环糊精 | 660 | 0 | 0 | 2000 | 2000 | 2000 | 2000 | 2000 | 2000 | 2000 |
γ-环糊精 | 660 | 0 | 2000 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
羧甲基纤维素(WaloceCRT 10000GA) | 55 | 55 | 55 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
羟丙基甲基纤维素MethocelK4MFG | 0 | 0 | 0 | 90 | 0 | 0 | 0 | 0 | 0 | 0 |
乙基纤维素 | 0 | 0 | 0 | 0 | 60 | 0 | 0 | 0 | 0 | 0 |
丙基纤维素 | 0 | 0 | 0 | 0 | 0 | 70 | 0 | 0 | 0 | 0 |
羟乙基纤维素Tylose MH 4000P2 | 0 | 0 | 0 | 0 | 0 | 0 | 90 | 0 | 0 | 0 |
羟丙基纤维素 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 60 | 0 | 0 |
乙基羟乙基纤维素 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 60 | 0 |
羧甲基羟乙基纤维素 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 90 |
柠檬油 | 200 | 150 | 230 | 10 | 1 | 250 | 100 | 50 | 200 | 75 |
实施例15:对照例
在表1中,根据本发明生产的颗粒比根据现有技术生产的颗粒在氧化稳定性、流动性和再分散性方面的优势是清楚的。更好的氧化稳定性是由于低表面油含量。
表1:
含d-柠檬油精的环糊精颗粒 | 按本发明 | 按EP-A 392608 | 按DE-A 31 05 666 | |
步骤 | 实施例2 | 捏合,喷雾干燥 | 捏合,干燥,研磨,筛分 | |
工艺 | 喷雾混合物的间歇制备连续、同时干燥和造粒 | 喷雾混合物的间歇制备,连续干燥,无造粒 | 连续挤出和造粒 | 混合物的间歇制备,间歇干燥,间歇研磨,间歇筛分 |
粒径 | 50μm-300μm | 0.05μm-5μm | 500μm-1000μm | 500μm-1000μm |
流动性(静止角) | 32° | 63° | 52° | 47° |
在20℃下的再分散性 | 4 | 0 | 3 | 3 |
表面油 | 0.04% | 0.40% | 2.4% | 0.19% |
保留率 | 86% | 74% | 92% | 86% |
氧化敏感性(180天后) | 0 | 3 | 5 | 3 |
根据DIN ISO 4324来测定流动性。静止角<30°意味着非常好的流动性,静止角在30°和40°之间意味着自由流动性,静止角>45°意味着差的流动性(参见Uhlemann,Mhr:Wirbelschichtsprühgranulation,Springer-Verlag Berlin,2000,p.169)。
在1天和180天的储存时间(储存温度20℃)后评估氧化敏感性。在每个例子中,将100克的样品装入250ml的塑料瓶中,该塑料瓶用盖子密封。在特定的储存时间之后,打开瓶子并根据气味评估。在0(无氧化气味)到5(强烈的氧化气味)的等级上作出评估。一天后,所有表1的颗粒仍处于无味状态。
再分散性测定如下:20ml的水(20℃)和200mg的特定颗粒被放在玻璃烧杯中并用磁力搅拌器以200min-1搅拌1分钟。在0(非常差的再分散性)到5(完全再分散)的等级上作出评估。若搅拌后,不是所有的颗粒都被水润湿,在1分钟的静置时间后形成大的团聚和/或大量颗粒沉降到底部,那么颗粒被称为具有非常差的再分散性。
实施例16:具有薄荷口味的口香糖
将来自实施例3的2wt.%的薄荷调味剂/环糊精颗粒(相应于0.18wt.%的调味剂)和1.12wt.%的液态薄荷调味剂混入口香糖(B)中。为了比较,制备含1.30wt.%的液态薄荷调味剂的口香糖(A)。
由一组经过训练的测试者(12人)研究感官时间/强度,含有薄荷调味剂颗粒的口香糖(B)整体显示出明显更高强度的口感。15分钟后,含有薄荷调味剂/环糊精颗粒的样品中的香味强度高两倍。
X=咀嚼时间,以分钟计
Y=薄荷味的强度
A=含有液态薄荷调味剂的口香糖
B=含有液态薄荷调味剂+薄荷调味剂颗粒的口香糖
在0(无薄荷味)到10(非常强的薄荷味)的等级上评估薄荷味的强度。
实施例17:华夫饼干
以1.2wt.%的量(相应于0.1wt.%的调味剂)将实施例2的柠檬油精/环糊精颗粒加入到含有面粉、水、砂糖、卵磷脂、盐和花生油的华夫生面团中。在200℃的温度下烘焙华夫饼1分钟。为比较目的,液态柠檬油精以相同浓度混入具有相同组成的生面团中。在含有柠檬精油/环糊精颗粒的华夫饼的情况下,新鲜产品(1天的)的感官评估给出高的香味强度。可以通过分析证实感官评估,如在表2中所示。
表2:
含有0.1wt.%的以环糊精复合物形式的柠檬油精的华夫饼干 | 含有0.1%柠檬油精(液态)的华夫饼干 | |
在烘焙华夫饼干中的柠檬精油含量 | 2533ppm | 755ppm |
烘焙后的保留率 | 95% | 38% |
柠檬精油评价(储存后) | 3 | 0 |
香味丧失 | 0 | 4 |
感官描述 | 新鲜,类似柑橘 | 霉味,氧化的,腐臭的 |
在20℃下4个月的存储后进行柠檬精油成分的香味强度和香味丧失的感官评估,在0(察觉不到)到5(非常强烈)的等级上。
在本例中,保留率(以%表示)应被理解为在华夫饼干中的柠檬精油量与所用的柠檬精油量的相对重量比。
实施例18:速溶汤
将类似于实施例1生产的顺式-3-己烯醇/环糊精颗粒加入到含有盐,淀粉,香辛料粉末,植脂末和脱水蔬菜(以增强鲜绿感)的粉末混合物中。
由于设定的粒径为100~200μm,在混合过程中得到以下优点:无尘,低析出风险,良好的流动性。
在储存中,尤其是由于根据本发明生产的颗粒的低表面油含量,很好地防止了环糊精复合物中顺式-3-己烯醇的氧化。
当将80℃的水倾入速溶汤混合物中时,该复合物在几秒钟内溶解。
Claims (14)
1.一种含有调味剂和/或香料的环糊精颗粒,所述环糊精颗粒具有50~1000μm的粒径并含有纤维素醚,且可通过单级流化床工艺由喷雾混合物得到,其中气体入口温度为80-180℃和气体出口温度为40-95℃。
2.根据权利要求1的环糊精颗粒,其特征在于,它们含有至少一种选自甲基纤维素,乙基纤维素,乙基羟乙基纤维素,丙基纤维素,羟乙基纤维素,羟丙基纤维素,羟丙基甲基纤维素,羧甲基羟乙基纤维素和羧甲基纤维素的纤维素醚。
3.根据权利要求1或2的环糊精颗粒,其特征在于它们含有羧甲基纤维素。
4.根据权利要求1到3的任何一项的环糊精颗粒,其特征在于,其粒径范围为100~300μm。
5.根据权利要求1到4的任何一项的环糊精颗粒,其特征在于,流化床工艺为流化床喷雾造粒。
6.根据权利要求1到5的任何一项的环糊精颗粒,其特征在于,它们含有的环糊精为α-,β-,或γ-环糊精,优选为β-环糊精。
7.根据权利要求1到6的任何一项的环糊精颗粒,其特征在于,调味剂和/或香料的含量为0.01~30wt.%。
8.根据权利要求1到7的任何一项的环糊精颗粒的制备方法,其特征在于,将包含至少一种环糊精,至少一种调味剂和/或香料和至少一种纤维素醚的含水喷雾混合物加入到单级流化床设备中。
9.根据权利要求8的方法,其特征在于,流化床设备为流化床喷雾造粒装置,优选为连续操作。
10.根据权利要求8或9的方法,其特征在于,在流化床设备中进行成核。
11.根据权利要求8到10的任何一项的方法,其特征在于,含水喷雾混合物包含40~95wt.%的水,5~50wt.%的环糊精,0.0005~15wt.%的调味剂和/或香料和0.1~6wt.%的纤维素醚。
12.根据权利要求11的方法,其特征在于,含水喷雾混合物包含60~80wt.%的水,15~30wt.%的环糊精,0.25~5wt.%的调味剂和/或香料和0.2~2wt.%的纤维素醚。
13.一种含有调味剂和/或香料的环糊精颗粒,所述环糊精颗粒具有50~1000μm的粒径并含有羧甲基纤维素。
14.根据权利要求1到7的任何一项所述的环糊精颗粒在食品、药品和日用品中的用途。
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CN1678674A true CN1678674A (zh) | 2005-10-05 |
CN1329440C CN1329440C (zh) | 2007-08-01 |
Family
ID=31724288
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB038210657A Expired - Fee Related CN1329440C (zh) | 2002-09-04 | 2003-09-02 | 环糊精颗粒 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7348035B2 (zh) |
EP (1) | EP1537174A1 (zh) |
CN (1) | CN1329440C (zh) |
AU (1) | AU2003264145A1 (zh) |
DE (1) | DE10240698A1 (zh) |
WO (1) | WO2004022642A1 (zh) |
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CN102266123A (zh) * | 2010-06-07 | 2011-12-07 | 湖北中烟工业有限责任公司 | 选择性降低烟气酚类化合物的β-环糊精复合颗粒及应用 |
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CN102327617B (zh) * | 2005-10-26 | 2014-08-20 | 锡德克斯药物公司 | 磺基烷基醚环糊精组合物和其制备方法 |
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FI67168C (fi) * | 1980-02-18 | 1985-02-11 | Chinoin Gyogyszer Es Vegyeszet | Foerfarande foer aromatisering av te och foer aromatisering ave anvaendbara produkter |
JPS58172311A (ja) * | 1982-04-02 | 1983-10-11 | Kodama Kk | 持続性製剤及びその製法 |
EP0163836B1 (de) | 1984-04-07 | 1988-10-12 | Bayer Ag | Verfahren und Vorrichtung zur Herstellung von Granulaten |
US5102564A (en) * | 1989-04-12 | 1992-04-07 | The Procter & Gamble Company | Treatment of fabric with perfume/cyclodextrin complexes |
ATE124422T1 (de) * | 1989-04-12 | 1995-07-15 | Procter & Gamble | Festes verbraucherprodukt, welches feinteilige cyclodextrin-komplexe enthält. |
CN1073711A (zh) * | 1991-12-27 | 1993-06-30 | 昆明五华香料厂 | 微囊赋香剂及其制备方法与用途 |
JPH07165616A (ja) * | 1993-12-09 | 1995-06-27 | Hisamitsu Pharmaceut Co Inc | シクロデキストリンの複合組成物及び複合化法 |
CN1188143A (zh) * | 1997-01-13 | 1998-07-22 | 浙江高创科技发展有限公司 | 洗涤用的香料颗粒 |
-
2002
- 2002-09-04 DE DE10240698A patent/DE10240698A1/de not_active Withdrawn
-
2003
- 2003-09-02 AU AU2003264145A patent/AU2003264145A1/en not_active Abandoned
- 2003-09-02 US US10/476,828 patent/US7348035B2/en not_active Expired - Fee Related
- 2003-09-02 WO PCT/EP2003/009713 patent/WO2004022642A1/de not_active Application Discontinuation
- 2003-09-02 EP EP03793785A patent/EP1537174A1/de not_active Withdrawn
- 2003-09-02 CN CNB038210657A patent/CN1329440C/zh not_active Expired - Fee Related
Cited By (8)
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CN101365459B (zh) * | 2005-10-26 | 2011-11-30 | 锡德克斯药物公司 | 磺基烷基醚环糊精组合物和其制备方法 |
CN102327617B (zh) * | 2005-10-26 | 2014-08-20 | 锡德克斯药物公司 | 磺基烷基醚环糊精组合物和其制备方法 |
CN101983018A (zh) * | 2008-06-25 | 2011-03-02 | 日本烟草产业株式会社 | 吸烟物品 |
CN101983018B (zh) * | 2008-06-25 | 2013-03-27 | 日本烟草产业株式会社 | 吸烟物品 |
CN102266123A (zh) * | 2010-06-07 | 2011-12-07 | 湖北中烟工业有限责任公司 | 选择性降低烟气酚类化合物的β-环糊精复合颗粒及应用 |
CN102805425A (zh) * | 2012-08-30 | 2012-12-05 | 江苏中烟工业有限责任公司 | β-胡萝卜素/β-环糊精包合物在降低卷烟烟气中酚类化合物释放量中的应用 |
CN104886528A (zh) * | 2015-05-25 | 2015-09-09 | 昆明理工大学 | 一种牛肝菌肉味香粉及其制备方法 |
CN104886528B (zh) * | 2015-05-25 | 2017-07-28 | 昆明理工大学 | 一种牛肝菌肉味香粉及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2004022642A1 (de) | 2004-03-18 |
EP1537174A1 (de) | 2005-06-08 |
US7348035B2 (en) | 2008-03-25 |
CN1329440C (zh) | 2007-08-01 |
US20040234479A1 (en) | 2004-11-25 |
DE10240698A1 (de) | 2004-03-18 |
AU2003264145A1 (en) | 2004-03-29 |
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