CN102036716B - 清凉组合物 - Google Patents
清凉组合物 Download PDFInfo
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- CN102036716B CN102036716B CN200980118611.3A CN200980118611A CN102036716B CN 102036716 B CN102036716 B CN 102036716B CN 200980118611 A CN200980118611 A CN 200980118611A CN 102036716 B CN102036716 B CN 102036716B
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- isopropyl
- cooling compounds
- methyl
- ethyl
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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Abstract
一种液体清凉组合物，其为至少一种主要清凉化合物、至少一种不同的次要清凉化合物和至少一种用于主要清凉化合物的可摄入的非极性溶剂的混合物，主要清凉化合物∶次要清凉化合物∶溶剂的重量比为1∶1.5-2.25∶2-4.4。
Description
本公开涉及用于实用制剂中的清凉化合物的混合物。
清凉化合物就是向皮肤或身体粘膜赋予清凉感觉的化合物，其是公知和广泛使用的。成功化合物的例子包括(1R，2S，5R)-N-乙基-2-异丙基-5-甲基环己烷甲酰胺和2-异丙基-N，2，3-三甲基丁酰胺，其分别商业化为WS-3TM和WS-23TM。近来，特别有效的清凉化合物是(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷-甲酰胺，EvercoolTM180。
清凉化合物的一个问题是如何实现其最大效果。一些清凉化合物在溶剂中溶解性不好，这就意味着其在一些用品中所能加入的量，以及由此而来的能够观察到的效果受到了限制。人们认为借助封装技术控制释放是一种改善这种状况的方式，但是其同样引起了在所用封装溶剂中的溶解性的问题。此外，还有所述化合物的结晶问题。
已经发现，可以大大提高可溶解的以及由此而来的可用在用品中的量。因此，提供一种液体清凉组合物，其为至少一种主要清凉化合物、至少一种不同的次要清凉化合物和至少一种用于主要清凉化合物的可摄入的非极性溶剂的混合物，主要清凉化合物∶次要清凉化合物∶溶剂的重量比为1∶1.5-2.25∶1.75-4.4。
此外，还提供一种将至少一种主要清凉化合物结合在用品中的方法，所述方法包括将所述主要清凉化合物与至少一种不同的次要清凉化合物和至少一种用于主要清凉化合物的可摄入的非极性溶剂混合，并将所得混合物加入到所述用品中。
“液体”意指组合物形成时为液体并保持如此，至少直至结合至终产品或结合至捕集形式中时。组合物的一个特征为，其在室温下可以在几小时至几周的相当长的时间内保持为液体。在一些情况下，组合物在升高的温度下可以保持为液体直至加工时。虽然在任何情况下都不希望发生结晶，但是当其发生在所述组合物结合至终产品或捕集形式中时是可以接受的。
所述组合物具有两种不同类型的清凉化合物，称为主要清凉化合物和次要清凉化合物。“主要”清凉化合物意指熔点为至少75°的清凉化合物，而次要清凉化合物的熔点为低于90℃。
一些清凉化合物，例如(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)的熔点允许其可以作为主要或次要清凉化合物。在这种情况下，将所述化合物选择为主要或次要清凉化合物，并且选择不同的次要或主要清凉化合物与其混合。
主要清凉化合物的典型例子包括(1R，2S，5R)-N-乙基-2-异丙基-5-甲基环己烷甲酰胺、(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)、(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)。
次要清凉化合物的典型例子包括乳酸薄荷酯、2-异丙基-N，2，3-三甲基丁酰胺(WS-23TM)、(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)。
本申请中使用的非极性溶剂为可摄入液体，即其为可以用在食物、饮料和口服可接受的药物产品中的溶剂。其至少能够在一些程度上溶解主要清凉化合物，优选溶解程度为至少0.0005g/mL。
这种溶剂的典型例子包括Mygliol(MCT)、薄荷油、留兰香油、甘油三乙酸酯、橙油、柠檬油、白柠檬油、液体调味剂和薄荷醇。
特殊的组合物包括：
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)/乳酸薄荷酯/Mygliol；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)/乳酸薄荷酯/甘油三乙酸酯；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)/2-异丙基-N，2，3-三甲基丁酰胺(WS-23TM)/Mygliol；
(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)/乳酸薄荷酯/Mygliol；
(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)/2-异丙基-N，2，3-三甲基丁酰胺(WS-23TM)/Mygliol；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)/乳酸薄荷酯/薄荷油；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺(EvercoolTM180)/(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺(EvercoolTM190)/乳酸薄荷酯/甘油三乙酸酯。
在特殊的实施方案中，主要清凉化合物∶次要清凉化合物∶溶剂的比例为1∶1.8-2.2∶2.5-3.5。
本公开的液体组合物特别稳固，其中的一些格外如此，具有良好的贮存稳定性并且很少或者没有沉淀，甚至在易变的温度和湿度下。其可以很容易地结合至所有类型的食物、饮料和口服可接受的药物产品中。
这些组合物可以用在可施用于粘膜，例如口腔粘膜，或皮肤上以赋予清凉感觉的产品中。“施用”是指任何形式的接触，例如口服摄入、局部施用，或者对于烟草制品而言是指吸入。当施用于皮肤时，可以例如在乳霜或药膏中包含该化合物。因此，还提供一种向粘膜或皮肤提供清凉感觉的方法：向其施用包含有效量的上述清凉组合物的产品。
施用于口腔粘膜的产品包括但不限于经口摄入和吞咽的食物和饮料，以及摄入原因不在于其营养价值的产品，例如片剂、锭剂、漱口水、喷喉剂、牙粉和口香糖，其可以是为了清洁、清新、治疗和/或除臭的目的而施用于口腔粘膜。
施用于皮肤的产品包括但不限于香水、化妆用品、化妆品，例如乳液、油、软膏和洗浴试剂，其可以出于医疗或其它原因而施用于人体的皮肤上。
食物和饮料的特殊例子包括冷冻糖果，例如冰激凌和果汁冰水；甜点心，例如果冻和布丁；糖果，例如蛋糕、饼干、巧克力和口香糖；果酱；糖；面包；茶饮料，例如绿茶、红茶、甘菊茶、桑叶茶、南非茶、薄荷茶；汤；调味品；速溶饮料；点心等。
局部施用的产品的其它例子可包括但不限于皮肤护理化妆品，例如清洁纸巾、爽身粉、面霜、乳液、强壮剂(tonics)和凝胶；护手霜、手和身体用乳液、去脂肪/纤体霜和乳液、乳液、香膏、凝胶、喷雾剂和乳霜；晒斑化妆品，包括防晒液、香膏、凝胶、喷雾剂和乳霜；晒后液、喷雾剂和乳霜；肥皂、牙签、唇膏、洗浴用试剂、除臭剂和止汗药、洁面霜、按摩霜等。
施用于口腔粘膜的产品的其它例子可以包括但不限于口腔护理产品，例如牙膏、牙凝胶、牙粉、牙增白产品、牙线、抗牙菌斑和抗牙龈炎组合物、用于治疗鼻部症状的组合物等。
因此，还提供一种选自下组的终产品：施用于口腔粘膜的产品和施用于皮肤的产品，例如局部施用产品、口腔护理产品、鼻部护理产品、化妆用品、可摄入产品和口香糖等，其包含产品基质和有效量的至少一种如上定义的清凉组合物。
上述清凉组合物还可以与已知的天然感觉化合物混合物，所述化合物例如为水蓊(Jambu)、高良姜、高良姜乙酸酯、山椒醇、capscacian、胡椒和生姜，或者所属领域熟练技术人员公知的其它调味剂和香料。调味剂和香料成分的适当的例子包括醇、醛、酮、酯、醚、乙酸酯、腈、萜烯烃、含氮或含硫的杂环化合物。调味剂和香料成分可以为天然或合成来源。许多的这些物质都列在参考文献，例如S.Arctander的书籍，PerfumeandFlavorChemicals，1969，Montclair，NewJersey，USA中。
简单地通过将组合物与产品直接混合就可以将所述清凉组合物用在所述产品中，或者可以在之前的步骤中在适当的捕集物质中对其进行捕集。适当的捕集物质和方式包括但不限于聚合物熔体或水凝胶、胶囊、微胶囊和纳米胶囊、脂质体、成膜剂和吸收剂，例如环状低聚糖(例如，环糊精)。可选地，可以使用乳化剂或分散稳定剂，例如天然树胶(例如，***树胶)或低分子量表面活性剂，例如甘油脂肪酸酯和糖类脂肪酸酯，将其作为溶液或乳液加入到适当的液体中，这种液体包括醇或多元醇(例如，甘油、丙二醇)甘油三乙酸酯和Mygliol。
可以按照任何方便的方法提供所述胶囊，例如芯-壳复合凝聚胶囊、基质型水凝胶胶囊和涂覆的胶囊。可以与这些组合物一起使用的可商购获得的捕集物质的例子包括GivaudanFlavorsCorp.的ULTRASEALTM、GRANUSEALTM和QPEARLTM产品，但是还可以使用任何类似的其它技术。
在特殊的实施方案中，所述组合物以喷雾干燥形式使用。喷雾干燥是一种所属领域公知的技术。通常，其包括在适当的乳化剂存在下，将所述组合物乳化至水中，然后将所述乳液喷雾至加热的空气流中。结果得到精细的颗粒物质。所述乳化剂可以为所属领域已知的任何适当的乳化剂，典型的例子包括***树胶、食物改性淀粉、麦芽糖糊精、印度树胶、明胶、酪蛋白酸钠、乳清蛋白、牛乳蛋白、藻酸钠和柑橘果胶。
因此，提供一种如上定义的、喷雾干燥形式的组合物。
如果将捕集组合物用在产品中，则其可以为清凉化合物的唯一来源，或者其中可以添加现有技术中已知的其它清凉化合物，例如薄荷醇、薄荷酮、异胡薄荷醇、N-乙基对薄荷烷甲酰胺(WS-3TM)、N，2，3-三甲基-2-异丙基丁酰胺(WS-23TM)、2-(2-异丙基-5甲基环己烷甲酰胺基)-乙酸乙酯(WS-5TM)、乳酸薄荷酯、薄荷酮甘油缩醛(FrescolatMGA)、琥珀酸单薄荷酯(Physcool)、戊二酸单薄荷酯、O-薄荷基甘油(CoolAct10)和2-仲丁基环己酮(Freskomenthe)、薄荷烷、樟脑、胡薄荷醇、桉油醇、薄荷油(mintoil)、薄荷油(peppermintoil)、留兰香油、桉树油、3-1-薄荷氧基丙-1，2-二醇、3-1-薄荷氧基-2-甲基丙-1，2-二醇、对薄荷烷-3，8-二醇、2-1-薄荷氧基乙-1-醇、3-1-薄荷氧基丙-1-醇、4-1-薄荷氧基丁-1-醇和以商品名QuesticeTM出售的薄荷基吡咯烷酮羧酸化合物。清凉化合物的其它例子可以在例如下述文献中找到：WO2005/049553(例如，2-异丙基-5-甲基-环己酸(4-氰基甲基-苯基)-酰胺和2-异丙基-5-甲基-环己酸(4-氰基-苯基)-酰胺)、WO2006/125334(例如，4-[(2-异丙基-5-甲基-环己烷羰基)-氨基]-苯甲酰胺、3-[(2-异丙基-5-甲基-环己烷羰基)-氨基]苯甲酰胺，和(2-异丙基-5-甲基-N-(4-(4-甲基哌嗪-1-羰基)苯基)环己烷甲酰胺)，和WO2007/019719(例如，2-异丙基-5-甲基-环己酸吡啶-2-基酰胺，和2-异丙基-5-甲基-环己酸(2-吡啶-2-基-乙基)-酰胺)，所述专利申请结合入本文作为参考。这些物质可以方便地以所属领域已知的量加入。
现在参考下列非限制性实施例进一步描述所述组合物和方法，所述实施例描述了特殊的实施方案。
实施例1：
确定适当的主要清凉剂(EvercoolTM180)、次要清凉剂(WS-23TM)和溶剂(Mygliol)的重量比。
制备溶液的一般步骤：
将主要清凉剂溶解在熔融的次要清凉剂中，然后用溶剂稀释。使所述溶液冷却至室温。
可以看出，主要清凉剂∶次要清凉剂∶Mygliol的比例为1∶1.5-2∶2-3特别有效。
实施例2：
主要清凉剂(WS-3TM)、次要清凉剂(WS-23TM)和溶剂(Mygliol)。
实施例3：
主要清凉剂(EvercoolTM180)、次要清凉剂(乳酸薄荷酯)和溶剂(Mygliol)。
该实施方案的最佳比例：
主要清凉剂∶次要清凉剂∶Mygliol1∶1.9-2.1∶2-4.4
实施例4：
主要清凉剂(WS-3TM)、次要清凉剂(乳酸薄荷酯)和溶剂(Mygliol)。
实施例5：
主要清凉剂(WS-3TM)，无次要清凉剂和溶剂(Mygliol)。
实施例6：
主要清凉剂(EvercoolTM180)、次要清凉剂(WS-3TM)和溶剂(Mygliol)-较高熔点的次要清凉剂的例子。
实施例7：
使用WS-23TM作为次要清凉剂，EvercoolTM180作为主要清凉剂，确定在作为溶剂的橙油(1x，巴西的)中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：1x巴西橙油100-3x％
与常规条件下在橙油(1x巴西的)中的＞1％EvercoolTM180相比，溶解性显著改善。
实施例8：
使用WS-23TM作为次要清凉剂，EvercoolTM180作为主要清凉剂，确定在作为溶剂的甘油三乙酸酯中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：甘油三乙酸酯100-3x％
实施例9：
使用WS-23TM作为次要清凉剂，EvercoolTM180作为主要清凉剂，确定在作为溶剂的薄荷醇中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：薄荷醇100-3x％
在65℃，常规条件下，与17％EvercoolTM180在薄荷醇中的溶解性相比，溶解性显著改善。
实施例10：
使用WS-23TM作为次要清凉剂，Evercool180作为主要清凉剂，确定在作为溶剂的10x加利福利亚橙油中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：10x加利福利亚橙油100-3x％
实施例11：
使用WS-23TM作为次要清凉剂，EvercoolTM180作为主要清凉剂，确定在作为溶剂的薄荷油中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：薄荷油100-3x％
室温，常规条件下，与12％EvercoolTM180在薄荷油中的溶解性相比，溶解性显著改善。
实施例12：
使用WS-23TM作为次要清凉剂，EvercoolTM180作为主要清凉剂，确定在极性溶剂丙二醇中的最佳浓度。
浓度
主要清凉剂：Evercool180x％
次要清凉剂：WS-232x％
溶剂：丙二醇100-3x％
实施例13：
主要清凉剂(EvercoolTM180)，次要清凉剂(WS-5TM)，溶剂(Mygliol)。
将1gEvercoolTM180热溶解在2gWS-5TM中，然后加入3gMygliol。使所述溶液在搅拌下冷却至室温，仅3h后即产生浑浊，4h后结晶。
实施例14：
主要清凉剂(EvercoolTM180)，次要清凉剂((1R，2S，5R)-2-异丙基-5-甲基-N-苯乙基环己烷甲酰胺)，溶剂(Mygliol)
将1gEvercool180热溶解在2g(1R，2S，5R)-2-异丙基-5-甲基-N-苯乙基环己烷甲酰胺中，然后加入3gMygliol。在搅拌下使所述溶液冷却至室温，仅1h后即产生浑浊，6h后结晶。
实施例15：
将乳酸薄荷酯(次要清凉剂)和Evercool180(主要清凉剂)以及Mygliol(溶剂)的混合物封装在非致龋的喷雾干燥基质中：
在将所述清凉剂加入到所述喷雾干燥基质中以形成乳液之前，可以将所述清凉剂溶解在油相中。对于该体系而言，32g乳酸薄荷酯在高于60℃时熔化。向其中加入16gEvercool180(2∶1重量比的乳酸薄荷酯∶Evercool180)，并加热至高于100℃直至溶解。然后以1∶1的比例向该均匀溶液中加入48g热的Mygliol(高于100℃)。之后使所述溶液保持在高于80℃以维持溶解性。然后将该油相加入到保持在60℃的***树胶溶液(36％的水溶液，400g***树胶，700g水)中。然后在标准条件下喷雾干燥该乳液。
实施例16：
乳酸薄荷酯(次要清凉剂)和EvercoolTM180的喷雾干燥混合物的应用及与参照物的对比：
树胶基质Solsona-T30g
山梨糖醇粉末50.6g
麦芽糖醇糖浆85％9g
甘露糖醇粉末5g
甘油5g
双氧噻嗪钾(Ace-KTM)0.09g
阿斯巴甜0.21g
喷雾干燥的清凉剂混合物(参见下表的量)
将树胶基质和一半的山梨糖醇混合，加入麦芽糖醇糖浆，然后与树胶物质混合。加入剩余的粉末成分(剩余的山梨糖醇、甘露糖醇、ace-K和阿斯巴甜)，混合约1分钟，此时加入甘油，将树胶物质混合约5分钟，以形成口香糖物质半成品。将清凉剂混合物加工至所述物质中，请评审小组成员咀嚼一片制得的口香糖(2g)，咀嚼20分钟并吐出。评价清凉感觉并记录其时间强度特性(参见图1)。
实施例17：
将乳酸薄荷酯(次要清凉剂)和Evercool180(主要清凉剂)以及Mygliol(溶剂)的混合物封装在封装基质中：
在将所述清凉剂加入到所述喷雾干燥基质中以形成乳液之前，必须将其溶解在油相中。对于该体系而言，50g乳酸薄荷酯在60℃以上熔化。将25gEvercool180加入到其中(2∶1重量比的乳酸薄荷酯∶Evercool180)，加热至高于100℃直至溶解，将其加至95g热的Mygliol(高于75℃)中。然后将该溶液加入到在340g水中的132g明胶100、42g明胶0、13g马铃薯淀粉和43g木糖醇的热(75℃)溶液中并将其搅匀。在75℃下持续搅拌溶液，期间使用Wurster插件(insert)将其涂覆在100g明胶100上(T溶液：75℃，P喷嘴：2.5巴，T入口：90)。
实施例18：
乳酸薄荷酯(次要清凉剂)和EvercoolTM180的封装混合物的应用以及与参照物的对比：
树胶基质Solsona-T30g
山梨糖醇粉末50.6g
麦芽糖醇糖浆85％9g
甘露糖醇粉末5g
甘油5g
双氧噻嗪钾(Ace-KTM)0.09g
阿斯巴甜0.21g
封装或喷雾干燥的清凉剂混合物(参见下表的量)
将树胶基质和一半的山梨糖醇混合，加入麦芽糖醇糖浆，然后与树胶物质混合。加入剩余的粉末成分(剩余的山梨糖醇、甘露糖醇、ace-K和阿斯巴甜)，混合约1分钟，此时加入甘油，将树胶物质混合约5分钟，以形成口香糖物质半成品。将清凉剂混合物加工至所述物质中，请评审小组成员咀嚼一片制得的口香糖(2g)，咀嚼20分钟并吐出。评价清凉感觉并记录其时间强度特性(参见图2)。
应该理解，本文中描述的实施方案仅仅是示例，所属领域熟练技术人员在不偏离发明的范围的情况下可以进行改变和变型。应该理解，上述实施方案不仅仅是相互替换的，而且可以组合。
Claims (9)
1.液体清凉组合物，其为至少一种主要清凉化合物、至少一种不同的次要清凉化合物和至少一种用于主要清凉化合物的可摄入的非极性溶剂的混合物，所述主要清凉化合物选自下组：(1R，2S，5R)-N-乙基-2-异丙基-5-甲基环己烷甲酰胺、(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺和(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺及其混合物，所述次要清凉化合物选自下组：乳酸薄荷酯、2-异丙基-N，2，3-三甲基丁酰胺和(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺及其混合物，主要清凉化合物：次要清凉化合物：溶剂的重量比为1∶1.5-2.25∶1.75-4.4。
2.根据权利要求1的组合物，其中主要清凉化合物：次要清凉化合物：溶剂的重量比为1∶1.8-2.2∶2.5-3.5。
3.根据权利要求1的组合物，其中所述非极性溶剂能够溶解所述主要清凉化合物的程度为至少0.0005g/mL。
4.根据权利要求1的组合物，其中所述主要清凉化合物/次要清凉化合物/溶剂的组合选自下组：
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺/乳酸薄荷酯/Mygliol；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺/乳酸薄荷酯/甘油三乙酸酯；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺/2-异丙基-N，2，3-三甲基丁酰胺/Mygliol；
(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺/乳酸薄荷酯/Mygliol；
(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺/2-异丙基-N，2，3-三甲基丁酰胺/Mygliol；
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺/乳酸薄荷酯/薄荷油；和
(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺/(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺/乳酸薄荷酯/甘油三乙酸酯。
5.适合用于口腔粘膜和皮肤中的至少一种的产品，其包含产品基质和有效量的至少一种根据权利要求1的清凉组合物。
6.根据权利要求5的产品，其中所述清凉组合物以捕集形式存在。
7.根据权利要求6的产品，其中所述捕集形式选自下组：聚合物熔体或水凝胶、胶囊、微胶囊和纳米胶囊、脂质体、成膜剂和吸收剂。
8.根据权利要求6的产品，其中所述捕集形式为喷雾干燥的颗粒。
9.将至少一种主要清凉化合物结合在产品中的方法，所述方法包括使所述主要清凉化合物与至少一种不同的次要清凉化合物和至少一种用于主要清凉化合物的可摄入的非极性溶剂混合，并将所得混合物加入到所述产品中，其中所述主要清凉化合物选自下组：(1R，2S，5R)-N-乙基-2-异丙基-5-甲基环己烷甲酰胺、(1R，2S，5R)-N-(4-(氰基甲基)苯基)-2-异丙基-5-甲基环己烷甲酰胺和(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺及其混合物，所述次要清凉化合物选自下组：乳酸薄荷酯、2-异丙基-N，2，3-三甲基丁酰胺和(1R，2S，5R)-2-异丙基-5-甲基-N-(2-(吡啶-2-基)乙基)环己烷甲酰胺及其混合物。
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- 2009-05-19 JP JP2011509833A patent/JP2011520925A/ja not_active Ceased
- 2009-05-19 CN CN200980118611.3A patent/CN102036716B/zh active Active
- 2009-05-19 BR BRPI0913127-2A patent/BRPI0913127B1/pt active IP Right Grant
- 2009-05-19 KR KR1020107025921A patent/KR101602513B1/ko active IP Right Grant
- 2009-05-19 US US12/992,375 patent/US20110091531A1/en not_active Abandoned
- 2009-05-19 SG SG10201810240TA patent/SG10201810240TA/en unknown
- 2009-05-19 WO PCT/CH2009/000161 patent/WO2009140783A1/en active Application Filing
- 2009-05-19 EP EP09749387.8A patent/EP2296759B1/en active Active
- 2009-05-19 SG SG2013063896A patent/SG193815A1/en unknown
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| CN1348352A (zh) * | 1999-04-16 | 2002-05-08 | 荷兰联合利华有限公司 | 化妆品组合物 |
| CN1501794A (zh) * | 2001-04-17 | 2004-06-02 | 凉爽组合物 | |
| CN1711075A (zh) * | 2002-11-14 | 2005-12-21 | Wm.雷格利Jr.公司 | 含有新香味组合物的口用产品 |
| CN101052369A (zh) * | 2004-10-04 | 2007-10-10 | 科蒂德国股份有限公司 | 化妆品清凉组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102036716A (zh) | 2011-04-27 |
| EP2296759A1 (en) | 2011-03-23 |
| SG193815A1 (en) | 2013-10-30 |
| SG10201810240TA (en) | 2018-12-28 |
| WO2009140783A1 (en) | 2009-11-26 |
| EP2296759B1 (en) | 2019-10-02 |
| JP2011520925A (ja) | 2011-07-21 |
| KR20110020777A (ko) | 2011-03-03 |
| BRPI0913127B1 (pt) | 2022-04-12 |
| BRPI0913127A2 (pt) | 2016-01-05 |
| KR101602513B1 (ko) | 2016-03-10 |
| US20110091531A1 (en) | 2011-04-21 |
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