CN101106911A - 喷雾干燥组合物及其应用 - Google Patents
喷雾干燥组合物及其应用 Download PDFInfo
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- CN101106911A CN101106911A CNA2006800028744A CN200680002874A CN101106911A CN 101106911 A CN101106911 A CN 101106911A CN A2006800028744 A CNA2006800028744 A CN A2006800028744A CN 200680002874 A CN200680002874 A CN 200680002874A CN 101106911 A CN101106911 A CN 101106911A
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- 229920000084 Gum arabic Polymers 0.000 claims abstract description 48
- 235000010489 acacia gum Nutrition 0.000 claims abstract description 48
- 239000000205 acacia gum Substances 0.000 claims abstract description 48
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract description 23
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229940041616 menthol Drugs 0.000 claims abstract description 23
- 235000015218 chewing gum Nutrition 0.000 claims abstract description 10
- 244000215068 Acacia senegal Species 0.000 claims description 46
- 239000003921 oil Substances 0.000 claims description 41
- 235000019198 oils Nutrition 0.000 claims description 41
- 239000000843 powder Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 20
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- 230000001166 anti-perspirative effect Effects 0.000 claims description 16
- 239000003213 antiperspirant Substances 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 238000004880 explosion Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
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- 239000003826 tablet Substances 0.000 claims description 9
- 239000006260 foam Substances 0.000 claims description 8
- 239000008368 mint flavor Substances 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007910 chewable tablet Substances 0.000 claims description 6
- 235000011194 food seasoning agent Nutrition 0.000 claims description 6
- 239000003205 fragrance Substances 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001525 mentha piperita l. herb oil Substances 0.000 claims description 4
- 235000019477 peppermint oil Nutrition 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
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- 235000008935 nutritious Nutrition 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 2
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
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- 159000000007 calcium salts Chemical class 0.000 claims description 2
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- 229960000448 lactic acid Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 229960005137 succinic acid Drugs 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 229960001367 tartaric acid Drugs 0.000 claims description 2
- 229940005605 valeric acid Drugs 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims 3
- 239000002781 deodorant agent Substances 0.000 claims 3
- 230000000050 nutritive effect Effects 0.000 claims 3
- 239000000344 soap Substances 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 claims 2
- 235000019837 monoammonium phosphate Nutrition 0.000 claims 2
- 239000001488 sodium phosphate Substances 0.000 claims 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims 2
- 235000011008 sodium phosphates Nutrition 0.000 claims 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims 1
- 239000004111 Potassium silicate Substances 0.000 claims 1
- 239000004115 Sodium Silicate Substances 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims 1
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- 150000008282 halocarbons Chemical class 0.000 claims 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims 1
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- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 claims 1
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- 235000019353 potassium silicate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims 1
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- 235000019795 sodium metasilicate Nutrition 0.000 claims 1
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明涉及一种喷雾干燥组合物,该组合物含有一种或多种分散于阿拉伯树胶载体与非离子表面活性剂的混合物中的活性成分。该组合物对于包封薄荷醇特别有用,并能用于制备口香糖和压制片剂。
Description
技术领域
本发明涉及包封形式的组合物以及制备所述组合物的方法。
背景技术
包封是将一种或多种活性成分用另一种材料或系统涂覆,或包埋于其中的方法。在香料和调味料工业中,活性成分的包封用于保留食品或消费品在贮藏过程中的香味,保护活性成分免于与环境(特别是食品)的不期望的相互作用,最小化香料/香料或调味料/调味料的相互作用,防止光引发反应或氧化,并且提供香料或调味料的受控释放。
在该工业中,生产包封的产品的最普遍的方法是喷雾干燥和范围稍小的挤出和凝聚方法。
喷雾干燥是一种香料业中用于使液体香料成为干燥的自由流动的粉末形式的公知的操作。它是达到该目的的划算并且有效的方法。工业标准的配方由两种主要成分组成:80份的非调味成分和20份的调味料(在室温下通常为疏水液体)。如果非调味料成分的乳化特性缺乏或不足,习惯上添加一定的乳化剂作为配方的一部分。
在喷雾干燥粉末中,活性成分(例如调味料或香料,通常为疏水的)作为液滴被包埋于脱水载体的固化的基质中,该基质通常由糖类,例如淀粉,水解淀粉(麦芽糖糊精),化学改性淀粉,乳化聚合物(阿拉伯树胶)和特定情况下的简单己醛糖的单体或二聚物,或它们的任意组合构成。传统的喷雾干燥技术在现有技术中已经有非常好的记载,例如见Spray-Drying Handbook,第四版,K.Masters,(1985)或者其它关于该主题的参考文献。
用于制备喷雾干燥粉末的方法通常包括:首先将载体于水中形成分散体,然后将该分散体与香料或调味料的混合物在均质化之前形成水包油的乳浊液。然后将该乳浊液喷雾干燥以生产粉末产品。
本发明主要涉及喷雾干燥的疏水物质的制备,其中基质主要由阿拉伯树胶组成,并且在最终粉末产品中疏水包封物的含量高于最终产品的重量的25wt%,更优选高于35wt%。这种喷雾干燥产品以“高固着度(high-fix)”著称,即粉末中疏水材料或包封油的含量比这种类型包封技术的传统含量值高20~25%。
阿拉伯树胶(也被称为金合欢胶)是一种节约成本的,备受好评并且广泛使用于喷雾干燥产品的包封材料。它的应用符合Kosher和Halal认证限制的需要。此外,它没有强烈的味道或香味的事实使得它成为包封多种的调味料材料的理想的载体。
该树胶由低分子量的多糖和少量的富含羟基脯氨酸的糖蛋白以及矿物质组成。这种独特的化学组成产生一些独特的为喷雾干燥所期望的官能度。相对低分子量的多糖允许在高固体含量时制备低粘度的树胶溶液。糖蛋白提供了有用的树胶的乳化特性。糖蛋白还具有形成连续膜的能力,有温和的味道并显示出低的吸湿性。
虽然大量的文献描述了关于使用糖聚合物作为载体时影响喷雾干燥效率的各种因素,但是涉及阿拉伯树胶通过其自身或者结合其它糖作为载体使用时,现有技术中的信息非常少。
在最近的研究中,B.F.McNamee等在J.Agric.Food Chem.49,3385-3388,2001中指出通过增加供给干燥机的进料固体,用麦芽糖糊精部分替换阿拉伯树胶可改进风味保持力。Y.Watanabe等在J.Agric.Food Chem.50,3984-3987,2002中描述了使用麦芽糖糊精和阿拉伯树胶作为载体的喷雾干燥系统中酰基抗坏血酸酯对亚油酸的氧化的作用,并指出用麦芽糖糊精部分替代阿拉伯树胶改进了粉末的氧化稳定性。最后,A.C.Bertolini等在Agric.Food Chem.49,780-785,2002中研究了阿拉伯树胶喷雾干燥产品中的单萜的氧化降解。所检测的所有通常使用的单萜例如柠檬烯、β-月桂烯、β-蒎烯、柠檬醛和里哪醇在55℃时迅速被氧化,表明阿拉伯树胶膜的弱的氧防护性能。
喷雾干燥的过程产生挥发损失并且这种损失随着固着度水平的增加而增加也是已知的事实。但是关于高固着度喷雾干燥的文献很少。
为了获得高固着度水平的疏水材料,公知可使用特殊的包封基质。具有高固着度水平的配方(通常高于50%)可有效地进行喷雾干燥,其具有超过90%的油的保持力并使用改性淀粉(辛烯基琥珀酰化淀粉-OSS)作为载体。它例如记载在美国US3,971,852号专利中。该专利主要涉及应用乳化淀粉(OSS)结合低分子量的糖的载体系统获得最终产品的氧化稳定性。在一个实施例中,它还描述了使用阿拉伯树胶与山梨醇和二异辛基磺基丁二酸酯(乳化剂)的结合以获得具有57.2%(w/w)的油含量的喷雾干燥粉末。
然而,由于限制的原因,二异辛基磺基丁二酸酯(离子表面活性剂/乳化剂)的使用不可能对食品应用总是适合。
传统上,当使用阿拉伯树胶作为载体时,在该喷雾干燥配方中有香味的油的固着度水平相对于喷雾干燥产品的重量不多于25wt%。这种限制的原因是由于当固着度水平超过25%时在喷雾干燥过程中油大量的损失。
例如,由本发明人进行的最近的研究中,对于在阿拉伯树胶中薄荷醇、薄荷精油或其它薄荷调味料组合物的包封,结果显示在或接近传统的油的固着度水平(20%)时在阿拉伯树胶载体上的薄荷醇的保持力至多为89%。
本发明的目标是提供一种以阿拉伯树胶作为载体的改进的喷雾干燥产品。本发明的该产品携带的包封疏水材料的量高于喷雾干燥产物重量的25wt%,并且更优选至少为35wt%,具有高于90%,大多数情况接近100%的油的保持力水平。
发明内容
现在本发明涉及一种新型喷雾干燥组合物,该组合物含有至少一种分散于阿拉伯树胶载体中的活性成分,其中所述活性成分以高于组合物干重的30wt%的量存在,所述载体中还进一步包含非离子表面活性剂。
这里所指的“活性成分”是一种通过固体包封的形式受到保护的疏水成分。它可包括挥发性香味或调味成分,以及其它种类的成分,即营养补充剂如Ω-3脂肪酸和Ω-6脂肪酸,维生素或药物活性成分。
本发明进一步涉及还含有防燃剂的上述喷雾干燥组合物。
本发明还涉及其中活性成分为薄荷醇,含有薄荷醇的调味料或香料或具有薄荷调和料的调味料或香料的上述喷雾干燥组合物。该组合物具体优点在于它们赋予食品和其它消费品冰凉和感觉特性,并且具体地将可能与薄荷的感官特性相关的刺激效果最小化。
本发明还涉及这种喷雾干燥组合物的制备方法,和其对产品如食品、饮料、药物或口腔护理组合物,或者甚至是香味组合物进行调味或加香的应用。
本发明的喷雾干燥粉末也可被有利地用作二次包封方法的中间体或起始产物,即作为能够被进一步包封的固体产品例如玻璃态基质中的挤出物以生成粒状的输送系统或者在独特或相似的基质中进行二次喷雾干燥操作的固体产品,并且本发明还涉及组合物的该应用。
本发明的更多的目的、方面和优点将会在此后的详细描述中变得更加明显。
附图说明
图1表示在阿拉伯树胶和麦芽糖糊精基的喷雾干燥产品中薄荷醇的保持力(百分比)作为薄荷醇浓度的函数。
图2表示溶剂可萃取的油(薄荷醇)的量(油未被包封,保留在喷雾干燥产品的表面)作为薄荷醇浓度的函数。
具体实施方式
本发明因而涉及新型喷雾干燥组合物,该组合物含有分散于阿拉伯树胶载体中的至少一种活性成分,其中所述活性成分高于组合物干重的30wt%,载体中还含有非离子表面活性剂。
根据本发明的实施方式,乳化剂优选食品级乳化剂,即二乙酰基酒石酸的甘油单酯或甘油二酯(DATEM)。后者的例子是商标为Panodan的购自Danisco A/S,Langenbrogade 1,PO Box 17,Copenhagen,DK-1001的产品。
如上所述,阿拉伯树胶具有非常好的乳化特性(但其乳化能力有限)。由于该原因,当它在喷雾干燥中用作载体时,可产生极好的香料保持力。然而,当另外的乳化剂/表面活性剂作为配方的一部分被添加时,对这种载体的性能可产生不利影响。但是,我们发现添加非离子表面活性剂对喷雾干燥在阿拉伯树胶基质中至多50wt%的薄荷调味料没有有害影响,这是个非常令人惊讶的结果。
本发明进一步涉及喷雾干燥粉末形式的组合物,该组合物含有一种或多种分散于载体中的活性成分,其中所述载体主要由阿拉伯树胶和非离子表面活性剂的混合物组成。
本发明的喷雾干燥产品证明对于包封香料业和调味料工业中使用的高含量的疏水液体成分非常有用,特别是对于获得薄荷醇和含有粉末产品重量的45wt%以上的薄荷醇的薄荷调味料或香料的粉末非常有用。这样的薄荷醇,薄荷油或其它薄荷调味组合物粉末对于口腔护理产品,具体例如口香糖,咀嚼片的应用非常重要,其中高浓度使得喷雾干燥的薄荷调味料在应用中特别节约成本。它们还具体用于加香应用例如泡沫剃须油和止汗剂。
本发明的组合物防止了喷雾干燥过程中过多的油的损失,使获得接近50%的活性成分的浓度,并具有在一般保存期限内接近100%保持力成为可能,并且这种使用的载体满足宽的限制标准,即适用于食品。
根据本发明的实施方式,该组合物含有相对于组合物重量的至少0.5wt%的非离子乳化剂和30wt%~50wt%的活性成分。
根据更加有利的实施方式,组合物将包含2wt%~10wt%的乳化剂和至少40wt%的活性包封物,组合物中剩余的成分为阿拉伯树胶。
根据本发明最佳实施方式,提供了一种喷雾干燥组合物,该组合物由55wt%~60wt%的阿拉伯树胶,2wt%~5wt%的DATEM和剩余为薄荷醇或薄荷活性组合物,即薄荷调味料组成。
在本发明的组合物中,可使用任何商业可用的阿拉伯树胶,例如任何俗名为土耳其树胶,印度树胶,金合欢树胶,Gum#414或阿拉伯树胶。树胶的种类和来源不是本发明的必要参数。
因而,本发明的必要特征在于阿拉伯树胶与非离子乳化剂(更具体的为DATEM)的结合。已证明适合本发明的其它非离子乳化剂包括Tween 80(聚氧乙烯失水山梨糖醇单油酸酯;购自Uniquema,3411 Silverside Road,Wilmington,DE 19803)和Glycosperse L20-K(聚氧乙烯失水山梨糖醇单月桂酸酯;[购自Lonza Inc.,90 Boroline Road,Allendale,NJ 07401])。
作为活性包封物,可使用任何想要获得粉末形式的液体疏水成分,本发明的组合物对生产高浓缩的,自由流动粉末有实际的价值,该粉末可溶于含水系统中以释放活性成分。
根据本发明非常有用的实施方式,本发明的喷雾干燥组合物的分散于载体中的活性成分优选为目前使用的疏水调味料或香料成分或组合物。
在此使用的术语“调味料和香料成分或组合物”定义为是天然或合成来源的多种调味料或香料成分。它们包括单一的化合物或混合物。本发明的组合物可包封液体形式的挥发性或不稳定成分,优选疏水的。这种成分的特定的例子可以在现有文献中找到,例如Fenaroli的Handbook of Flavor Ingredients,1975,CRC Press;或者VanNostrand编辑的M.B.Jacobs的Synthetic Food Adjuncts,1947;或者S.Arctander的Perfume and Flavor Chemicals 1969,Montclair,N.J.(USA),以及涉及香料和调味料工业的技术发展的众多的出版物和专利文献。对于加香,调味和/或增香消费品(即赋予传统上已加香或已调味的消费品以气味和/或风味或味道,或改变所述消费品的气味和/或味道)领域的技术人员来说,这些物质是公知的。
天然提取物同样可被包封到本发明的系统中;这些物质包括如柑橘提取物如柠檬油、橙油、酸橙油、柚子油或柑橘油,或者咖啡、茶、薄荷、可可、香草或草本精油和辛香料,以及其它。如前所述,优选的应用涉及薄荷油的包封。
本发明的可被优选包封的其它成分涉及营养成分,例如含有大量的Ω-3脂肪酸和/或Ω-6脂肪酸,即鱼油的动物油或植物油。
本发明的另一目的是制备喷雾干燥粉末的方法,该方法包括以下步骤:在阿拉伯树胶和非离子乳化剂的混合物中乳化活性成分;均质该乳浊液并喷雾干燥该乳浊液以形成颗粒状产品。
本发明方法的具体优点在于如本文所述的含有阿拉伯树胶和非离子乳化剂结合的组合物显示出活性成分的保持力,其非常有利地不受起始水乳浊液的固体含量的变化的影响。更具体地,在传统的喷雾干燥方法中,用于提供单一分散体的树胶粉末的高稀释率必然等同于这样的事实:稀释率越高,保留活性油(即调味料或香料)的载体膜在喷雾干燥后的效率将会越低。此外确定了在初始水乳浊液中的固体含量低于10%时预计将导致在喷雾干燥后活性成分的保持力将明显降低。目前,如以下的实施例所示,证明在本例子中本发明产品的活性疏水包封物的保持力不受稀释率或引入喷雾干燥机中的水乳浊液固体含量的影响。换句话说,可以采用高的稀释率以获得好的载体粉末的单一分散体而不引起包封油的保持力的任何缺陷,其完全是一个出乎意料的结果。
在本发明方法中使用的喷雾干燥设备可以是多种商业可用设备中的任一种。喷雾干燥设备的实例为Anhydro干燥机(来自:Attleboro Falls,Mass.的Anhydro Corp.),Niro干燥机(由Niro Atomizer Ltd.,Copenhagen,Denmark制造),或者Leaflash设备(来自:CCM Sulzer)。优选使用具有压力喷嘴的喷雾干燥机。
该方法将会在实施例1中做更加详细地描述。然而,喷雾干燥方法的典型参数在本领域是公知的并且本领域的技术人员可以轻易地调整。
本发明的颗粒具有通常为50~70μm的大小并且堆密度为0.4~0.6g/cm3。然而,获得的干燥粉末的颗粒测定法和堆密度可通过选择喷嘴(口大小/直径)和雾化压力的来调整以获得期望的粉末流动性。
根据本发明方法制备的喷雾干燥的粉末可以在应用中原样利用,例如用于给组合物加香或调味,其中释放是通过与水或潮湿源接触(例如在香水施敷中与汗接触,或在食物摄取或咀嚼片或口香糖情况下与唾液接触)引发的。该产品可节约成本地使用于任何应用中,在这些应用中载体的可能的水溶解度预期导致了活性成分的释放。
一个典型并且非常有用的应用是制备咀嚼片。在这种片剂应用中,在生产片剂时,当使用高速度的机器时,自由流动的调味料组合物是很重要的。然而,主要由于在颗粒表面上的非包封油(溶剂萃取油)的原因,传统的高固着度粉末的自由流动性较它们低固着度的相似物的小。本发明的配方导致了低的溶剂萃取油,因而生产出具有高的风味保持力的高固着度水平的自由流动的产品。这使得它们在用于部分包装或片剂制作的高速机器中使用时非常有价值。
在多种应用中被使用作为输送系统之前,本发明的喷雾干燥组合物还可有利地被用作可被进一步加工的起始材料。
具体地在本发明的一个实施方式中,为了生产具有改进的热稳定性的玻璃态基质,通过上述描述的方法获得的喷雾干燥颗粒可进一步被包封于挤出玻璃态基质中,该基质可由一种或多种糖材料形成或其仅包含增塑剂和乳化剂。美国专利US 5,087,461(其内容以参考方式包括于此)公开了一种挤出方式的喷雾干燥组合物的包封方法。该方法生成了具有0.3~3mm直径的细棒。
除了挤出方法之外,喷雾干燥之后使用其它种类的包封方法是可能的。获得的粉末例如可进行第二次喷雾干燥,因而提供两级喷雾干燥产品。这种技术以及一般多级喷雾干燥具体地被描述于W.J.Coumans,P.J.A.M.Kerkhof和S.Bruin的Drying Technology,Vol.12(1和2),(1994)中,其中的教示以参考方式包括于此。
这些实例并非限制性的包封技术,为了使颗粒适合于具体的应用,明显地以增加它的大小或者改进粉末的具体特征为目的,应用这些技术对根据本发明获得的喷雾干燥粉末进一步加工。
本发明的组合物除了阿拉伯树胶,非离子乳化剂和疏水的活性成分之外还可包含非强制性选择的成分。根据本发明的具体的有用的实施方式,它们可以进一步含有有效量的防燃剂或抑爆剂用于减少粉末爆炸的猛烈程度。喷雾干燥组合物中的这样试剂的类型和浓度详细描述于WO 03/043728 A1(FIRMENICH)中,其内容以参考方式包括于此。该文献公开了具有分散于或吸收于聚合载体材料中的防燃剂的加香或调味微胶囊,防燃剂基本上为无机盐。在此要特别涉及该文献中的教示和实施例,因为它们涉及在本发明上下文中用到的具体试剂的引用,将他们掺入本发明组合物的方法和使用它们的典型浓度。
除了WO 03/043728描述的那些之外,还可能具有另外的有益特性的适合作为抑爆剂的其它试剂也是本发明所预期的。例如它们可以使用很少的量,对微胶囊的吸湿性有有益的作用,或者甚至特别适合用于食品应用。
例如,C1-C12羧酸,C1-C12羧酸盐,和它们的混合物可以有效量被直接添加至加香或调味微胶囊中以降低在它们的制备过程中,特别是当它们悬浮于热空气和在它们的贮存过程中可能发生爆炸的猛烈程度。
术语“C1-C12羧酸”在此指含有1~12个碳原子(包括羧基的碳原子)的羧酸。因此,如果多于1个的羧基存在于羧酸中时,每个羧基的碳应该计算在上述的碳原子总数中。
在本发明微胶囊中可能被用作抑爆剂的羧酸和/或它们的盐可以是直链,支链,环状的和/或芳香的羧酸和/或它们的盐。羧酸可以是饱和烃或不饱和烃。
环状羧酸的例子为内酯,例如抗坏血酸即为优选的这类抑爆剂。合适的芳香族羧酸的例子是水杨酸。
优选地,羧酸和/或它们的盐为被官能化的烃的羧酸和/或它们的盐。
优选地,羧酸包含少于7个,更优选少于5个并且最优选少于3个共价地结合到2个氢原子上的碳原子。
优选地,本发明的羧酸含有5个或者更少的碳原子,其氧化数为(-II)或更负。更优选,羧酸含有3个或更少的碳原子,其氧化数为(-II)或更负。
在本发明的实施方式中,羧酸和/或它们的盐是羟基官能化和/或酮基官能化的烃基羧酸和/或它们的盐。
优选地,本发明的羧酸含有至少1个羟基。优选地,其含有2个羟基。
在本发明微胶囊的另一实施方式中,羧酸和/或它们的盐为二羧酸,三羧酸,或多羧酸和/或它们的盐。多羧酸的例子包括为C6-三羧酸的柠檬酸。
优选地,羧酸至少为二羧酸。更优选其至少为三羧酸,意思是它携带着至少三个羧基。
优选地,羧酸和/或它们的盐是C4-C8羧酸和/或它们的盐。
在本发明的优选实施方式中,羧酸和/或它们的盐选自C2-C6羧酸和/或它们的盐。
在实施本发明的优选模式中,羧酸和/或它们的盐选自由以下物质组成的组中:乙酸、丙酸、丁酸、异丁酸、戊酸、己酸、柠檬酸、琥珀酸、羟基琥珀酸、马来酸、富马酸、草酸、乙醛酸、己二酸、乳酸、酒石酸、水杨酸、抗坏血酸、任意前述酸的钾盐、钙盐和/或钠盐,和任意这些物质的混合物。
优选地,羧酸的盐为钾盐和/或钠盐。更优选地使用三羧酸的三钾盐和/或三钠盐。最优选地。其为柠檬酸的三钾盐和/或三钠盐。
以上的酸和/或它们的盐都是商业可用的,它们还可以由本身已知的方法合成或从天然物质中提取。
通常胶囊含有相对于微胶囊干重的2~15wt%,更优选2~10wt%的抑爆剂。
抑爆剂可添加到由分散于阿拉伯树胶和非离子乳化剂中的加香或调味成分组成的水乳浊液中。然后将得到的乳浊液喷雾干燥以形成粉末。这种包封技术在此不需要更加详细的描述,因为其所依赖的传统喷雾干燥技术之前已经提及并且已经很好地记载在现有技术中[例如见Spray-Drying Handbook,第三版,K.Masters;JohnWiley(1979)]并且在食品工业或调味料和香料业中普遍地应用。
在另一实施方式中,固体粉末形式的抑爆剂简单地与之前获得的喷雾干燥粉末混合,该喷雾干燥粉末如之前所述来自于在阿拉伯树胶载体和非离子乳化剂中的疏水的水样成分或组合物的水乳浊液。
进一步进行第二次的包封的本发明的产品(即如喷雾干燥粉末)和喷雾干燥组合物还可被有利地用于具体如食品组合物的加香或调味。
因此,本发明的输送系统可在如口香糖或咀嚼糖果、咀嚼片、成味食品或烤制食品调味料领域中应用。同样地,香料领域有很多应用,其中该种包封系统非常有用,特别是对于片剂形式的洗涤剂,泡沫剃须油和止汗剂喷雾,止汗剂粉末和止汗剂棒。
在消费品中掺入本发明的微胶囊的浓度可以在很宽数值范围内变动,其依赖于被加香和调味产品的性质。严格根据实施例的典型浓度为从几ppm至包括其在内的加香或调味组合物或最终消费品的重量的至多5%或10%。
采用阿拉伯树胶结合非离子表面活性剂/乳化剂制备的本发明的高固着度产品,特别是具有至多50%重量含量的活性成分的那些产品,与使用麦芽糖糊精作为载体制备的它们的相似物相比,具有充分改进的活性成分(即调味料)保持力。它们也可生产具有相对低的溶剂萃取精油(表明了有效的包封特别是在高活性成分〔具体为调味料〕保持力水平>95%时)的粉末。一些配方和分析结果在以下的实施例中给出。
现在将通过以下的实施例进一步详细地描述本发明,其中温度以摄氏度来表示并且缩写具有本领域常规含义。
实施例
以下的实施例进一步举例说明了本发明的实施方式,并且进一步指出了本发明设计较现有技术教示的优点。
实施例1~9
制备本发明喷雾干燥组合物并与含有组合物的麦芽糖糊精的
比较
使用以下所述的材料,设备和通用方法的条件制备九种粉末配方。
材料:
载体:阿拉伯树胶
麦芽糖糊精Morex 10-18DE
乳化剂:豆油来源的Panodan-FDPK DATEM
葵花籽油来源的Lamegin 39665 DWPS Cognis-DATEMTween 80K
Glycosperse L020K(脱水山梨糖醇单椰油酸酯)
调味料:薄荷醇
设备:具有标定的水蒸发速率60kg/hr的喷雾干燥机(箱型)
具有高压泵的两阶段均质器
Clevenger连续蒸气蒸馏装置
气相色谱-Hewlett Packard
粉末配方:
表1
样本# | %成分 | |||||
阿拉伯树胶 | 麦芽糖糊精 | 薄荷醇 | DATEM | Tween 80 | GlycosperseL20-K | |
1 | 58.00 | -- | 40.00 | 2.00 | -- | -- |
2 | 47.50 | -- | 50.00 | 2.50 | -- | -- |
3 | 37.00 | -- | 60.00 | 3.00 | -- | -- |
4* | -- | 58.00 | 40.00 | 2.00 | -- | -- |
5* | -- | 47.50 | 50.00 | 2.50 | -- | -- |
6* | -- | 37.00 | 60.00 | 3.00 | -- | -- |
7 | 58.00 | -- | 40.00 | -- | 2.00 | -- |
8 | 58.00 | -- | 40.00 | -- | -- | 2.00 |
9 | 55.00 | -- | 42.00 | 3.00 | -- | -- |
*对比样本,使用麦芽糖糊精作为载体
喷雾干燥方法:
喷雾干燥的条件给出如下:
进料固体=40%(非含水物质)
进料温度=65℃
均质化压力=100bar
进料压力=170~200bar
干燥器入口温度=175℃
干燥器出口温度=80℃
干燥器空气流动速率=30m3/min
Spraying Systems Inc.提供的喷嘴=70/216
将样本收集并分析如下:
全油测定:将10g样本使用Clevenger装置通过连续蒸气蒸馏测定全油。将1ml甲苯加入到蒸馏烧瓶中防止薄荷醇在装置的侧臂上结晶。蒸馏持续两个小时,通过以下公式计算油的含量:
重量测定油含量=[(油ml-1)×0.89a]/[样本重g]
a薄荷醇的密度
溶剂萃取油:将A.Scottitantawat等的J.Food Sci.,Vol 68,No.7,2003,p.2256-2261文献中描述的GC-内标方法予以改进和使用。萃取时间减少到10秒并且使用2-壬酮作为内标。
表2总结了通过以上方法用表1中列出的各自的材料制备的九种喷雾干燥薄荷醇样本的分析结果。
表2
样本# | %固着度 | %油含量 | %保持力 | 萃取油% |
1 | 40.00 | 40.05 | >100.00 | 0.75 |
2 | 50.00 | 48.06 | 96.12 | 5.52 |
3 | 60.00 | 56.07 | 93.45 | 29.40 |
4* | 40.00 | 37.38 | 94.50 | 3.70 |
5* | 50.00 | 35.60 | 71.20 | 7.50 |
6* | 60.00 | 44.50 | 74.17 | 8.20 |
7 | 40.00 | 41.83 | >100.00 | 0.08 |
8 | 40.00 | 39.60 | 99.00 | 0.04 |
9 | 42.00 | 40.50 | 96.43 | -- |
*对比样本,使用麦芽糖糊精作为载体
在该表中的结论清楚地显示出喷雾干燥中使用的载体系统对薄荷醇保持力以及溶剂萃取调味料/油具有明显的效果,当与麦芽糖糊精比较时,在它的很宽浓度范围内保存油的能力方面和被包封油的浓度低于50wt%时减少溶剂萃取油的水平两方面,阿拉伯树胶显示出稳定的优越性。这些效果以表格的形式分别列于表1和表2中。
溶剂萃取油被认为未包封于干燥粉末中。如果溶剂萃取薄荷醇以粉末中全部的薄荷醇的比例来计算,将显示出非常高(>98%)的包封。但是当乳化剂以基于薄荷醇含量的5%的水平使用并且用阿拉伯树胶作为载体时,随着固着度水平的增加,溶剂萃取油的量非常显著地增加。
当在相同的乳化剂中使用麦芽糖糊精作为载体,固着度水平超过40%时调味料的损失是非常显著的,但溶剂萃取油的增加不是很明显。
实施例10
以不同的固体含量,制备本发明的喷雾干燥组合物
如之前实施例所示进行,通过改变在该方法中使用的进料固体重量百分比,制备具有与表2中的样本1相同的干重组合物的本发明的包封油。这些测试的结果给出如下:
样本 | %溶剂萃取油 | 进料固体(%非含水物质) | %保持力 |
A | 0.037 | 20 | 97.90 |
B | 0.037 | 30 | 99.03 |
C | 0.057 | 50 | 99.03 |
以上结果显示在本发明方法中改变起始乳浊液的固体含量不影响包封油的保持力。
实施例11
制备泡沫剃须油
通过包封了香料的本发明的阿拉伯树胶的胶囊为泡沫剃须油加香,并以通常已知的方式混合下述成分来制备泡沫剃须油:
成分 %重量
异丙基棕榈酸酯 49.00
三[月桂基聚氧乙烯(4)醚]磷酸酯 2.00
MIPA-[月桂基聚氧乙烯醚]硫酸酯(和)
月桂基聚氧乙烯(4)醚(和)椰油酰胺DEA 42.30
酰胺丙基葵花籽 0.50
二甲胺乳酸红没药醇酯 0.50
椰油酰胺DEA 3.00
KATHON CG(Rohm & Haas) 0.10
生育酚(TENOX GT-2,Eastmann) 0.50
硫代二丙酸二月桂酯 0.10
香料 1.00
阿拉伯树胶胶囊 1.00
实施例12
制备止汗剂喷雾
通过包封了香料的本发明的阿拉伯树胶胶囊为止汗剂喷雾加香,并以通常已知的方式混合下述成分来制备止汗剂喷雾:
成分 %重量
环聚甲基硅氧烷 11.75
肉豆蔻酸异丙酯 2.20
硅石 0.25
季铵盐-18水辉石 0.80
氢氯酸铝 8.00
香料 0.40
阿拉伯树胶胶囊 1.60
丙烷/丁烷2.5bar 75.00
实施例13
制备止汗剂粉末
通过包封了香料的本发明的阿拉伯树胶胶囊为止汗剂粉末加香,并以通常已知的方式混合下述成分来制备止汗剂粉末:
成分 %重量
滑石 87.00
氢氯酸铝 10.00
香料 1.50
阿拉伯树胶的胶囊 1.50
实施例14
制备止汗剂棒
通过包封了香料的本发明的阿拉伯树胶胶囊为止汗剂棒加香,并以通常已知的方式混合下述成分来制备止汗剂棒:
成分 %重量
环聚甲基硅氧烷 48.50
十八醇 21.00
聚丙二醇-14丁基醚 2.00
氢化蓖麻油 1.00
辛基十二醇 4.00
氢氯酸铝 21.00
香料 1.00
阿拉伯树胶胶囊 1.50
实施例15
制备口香糖
通过包封了香料的本发明的阿拉伯树胶胶囊为口香糖加香,并以通常已知的方式混合下述成分来制备口香糖:
成分 %重量
特细精糖粉 59.35
树胶基-Nova Base T 19.40
玉米糖浆,42 DE 19.80
柠檬酸 0.70
甘油 0.50
阿拉伯树胶胶囊 0.25
Claims (19)
1.喷雾干燥组合物,含有至少一种分散于阿拉伯树胶载体中的活性成分,其中所述活性成分以高于组合物干重的30wt%的量存在,所述载体中进一步包含非离子表面活性剂。
2.根据权利要求1的喷雾干燥组合物,其中非离子表面活性剂是二乙酰基酒石酸的甘油单酯或甘油二酯。
3.根据权利要求2的喷雾干燥组合物,其中活性成分是调味料或香料成分或组合物。
4.根据权利要求3的喷雾干燥组合物,其中活性成分是薄荷醇,薄荷油或薄荷调味料。
5.根据权利要求1的喷雾干燥组合物,其含有相对于组合物干重的2~15wt%的选自由以下物质构成的组中的非离子表面活性剂:二乙酰基酒石酸的甘油单酯或甘油二酯,聚氧乙烯失水山梨糖醇单油酸酯和聚氧乙烯失水山梨糖醇单月桂酸酯型的表面活性剂。
6.根据权利要求1的喷雾干燥组合物,其含有相对于组合物干重的30~50wt%的活性成分。
7.根据权利要求6的喷雾干燥组合物,其含有薄荷醇,薄荷油或薄荷调味料,并且其中非离子表面活性剂为二乙酰基酒石酸的甘油单酯或甘油二酯。
8.根据权利要求7的喷雾干燥组合物,其中非离子表面活性剂以相对于组合物干重的2~10wt%的浓度存在。
9.根据权利要求1的喷雾干燥组合物,其进一步含有抑爆剂。
10.根据权利要求9的喷雾干燥组合物,其中抑爆剂选自由以下物质组成的组:硅酸钠、硅酸钾、碳酸钠、碳酸氢钠、磷酸二氢铵、碳酸氢铵、磷酸氢二铵、磷酸二氢钠、磷酸氢钠、磷酸钠、次磷酸钠、氰尿酸三聚氰胺、卤代烃和它们的混合物。
11.根据权利要求10的喷雾干燥组合物,其中抑爆剂选自由下列物质组成的组: 乙酸、丙酸、丁酸、异丁酸、戊酸、己酸、柠檬酸、琥珀酸、羟基琥珀酸、马来酸、富马酸、草酸、乙醛酸、己二酸、乳酸、酒石酸、水杨酸、抗坏血酸、任意前述酸的钾盐、钙盐和/或钠盐,和任意这些物质的混合物。
12.根据权利要求10的喷雾干燥组合物,其含有相对于组合物干重的5~15wt%的抑爆剂。
13.根据权利要求11的喷雾干燥组合物,其含有相对于组合物干重的5~15wt%的抑爆剂。
14.由食品、饮料、营养补充剂、口腔护理组合物、除臭剂、片剂或口香糖组成的产品,其含有足够量的权利要求1的喷雾干燥组合物以赋予、改进、改变或提高它的味道、气味和/或营养价值。
15.根据权利要求14的产品,其为咀嚼片或口香糖形式。
16.根据权利要求14的产品,其为肥皂或清洁剂片剂或身体除臭剂或泡沫剃须油的形式。
17.对产品进行调味、加香和/或强化营养的方法,该产品是食品、饮料、营养补充剂、口腔护理组合物、片剂或口香糖、肥皂或清洁剂片剂或身体除臭剂或泡沫剃须油,该方法包括在该产品中加入足够量的权利要求1的喷雾干燥组合物以赋予、改进、改变或提高所述产品的味道、气味和/或营养价值。
18.根据权利要求17的方法,其中所述产品是咀嚼片或口香糖。
19.根据权利要求17的方法,其中该产品是肥皂或清洁剂片剂,止汗剂喷雾、止汗剂粉末、或止汗剂棒,或泡沫剃须油。
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2006
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- 2006-01-20 JP JP2007553752A patent/JP2008528680A/ja active Pending
- 2006-01-20 WO PCT/IB2006/050225 patent/WO2006082536A1/en active Application Filing
- 2006-01-20 CN CN2006800028744A patent/CN101106911B/zh active Active
- 2006-01-20 PL PL06710713T patent/PL1845803T3/pl unknown
- 2006-01-20 EP EP06710713.6A patent/EP1845803B1/en active Active
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- 2006-01-20 BR BRPI0607250-0A patent/BRPI0607250A2/pt not_active Application Discontinuation
- 2006-01-20 MX MX2007009167A patent/MX2007009167A/es active IP Right Grant
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2007
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2012
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CN103501634A (zh) * | 2011-05-03 | 2014-01-08 | 奇华顿股份有限公司 | 方法 |
CN103501634B (zh) * | 2011-05-03 | 2017-12-01 | 奇华顿股份有限公司 | 方法 |
CN105307510A (zh) * | 2013-06-21 | 2016-02-03 | 弗门尼舍有限公司 | 包含薄荷醇的干燥颗粒的制备 |
CN116076691A (zh) * | 2013-06-21 | 2023-05-09 | 弗门尼舍有限公司 | 包含薄荷醇的干燥颗粒的制备 |
CN107923896A (zh) * | 2015-04-24 | 2018-04-17 | 高露洁-棕榄公司 | 作为活性剂载体的多孔蛋白颗粒 |
CN107690284A (zh) * | 2015-05-27 | 2018-02-13 | 奇华顿股份有限公司 | 喷雾干燥 |
CN108472220A (zh) * | 2015-11-15 | 2018-08-31 | 西姆莱斯股份公司 | 减少皮肤刺痛感受 |
CN111278531A (zh) * | 2017-10-13 | 2020-06-12 | W·M·巴尔公司 | 呈压制片剂形式的包封的香料 |
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RU2007132911A (ru) | 2009-03-10 |
PL1845803T3 (pl) | 2014-09-30 |
ES2484793T3 (es) | 2014-08-12 |
MX2007009167A (es) | 2007-08-14 |
JP2013051964A (ja) | 2013-03-21 |
JP2008528680A (ja) | 2008-07-31 |
WO2006082536A1 (en) | 2006-08-10 |
US20080044551A1 (en) | 2008-02-21 |
CN101106911B (zh) | 2011-11-02 |
US20140056836A1 (en) | 2014-02-27 |
BRPI0607250A2 (pt) | 2010-03-23 |
JP5762383B2 (ja) | 2015-08-12 |
EP1845803A1 (en) | 2007-10-24 |
EP1845803B1 (en) | 2014-04-30 |
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