CN1642523A - 萜类化合物在化妆品组合物中的稳定 - Google Patents
萜类化合物在化妆品组合物中的稳定 Download PDFInfo
- Publication number
- CN1642523A CN1642523A CNA038067463A CN03806746A CN1642523A CN 1642523 A CN1642523 A CN 1642523A CN A038067463 A CNA038067463 A CN A038067463A CN 03806746 A CN03806746 A CN 03806746A CN 1642523 A CN1642523 A CN 1642523A
- Authority
- CN
- China
- Prior art keywords
- ester
- acid
- resorcinol
- terpenoid
- methyl
- 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
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- 150000003505 terpenes Chemical class 0.000 title claims abstract description 56
- 239000002537 cosmetic Substances 0.000 title claims abstract description 25
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- -1 4-substituted resorcinol Chemical class 0.000 claims abstract description 72
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 53
- 150000002148 esters Chemical class 0.000 claims description 50
- 229960001755 resorcinol Drugs 0.000 claims description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
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- 235000007586 terpenes Nutrition 0.000 claims description 15
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
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- 238000007254 oxidation reaction Methods 0.000 claims description 8
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- 229940114124 ferulic acid Drugs 0.000 claims description 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 4
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- SHEUEEZGXLCROM-YHYXMXQVSA-N α-santalal Chemical compound C1C2C3(C)C2CC1C3(C)CC/C=C(C=O)/C SHEUEEZGXLCROM-YHYXMXQVSA-N 0.000 description 1
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Abstract
本发明涉及一种化妆品组合物，它含有萜类化合物和4－取代间苯二酚衍生物，该组合物显示改进的储存稳定性和氧化稳定性。
Description
本发明涉及用于个人护理和个人洗涤产品中的含有被4-取代间苯二酚衍生物稳定的萜类化合物的化妆品组合物。
萜在自然界中广泛存在，主要存在于植物中作为精油的成分。许多萜是烃类化合物，但是也有含氧化合物例如醇、醛或酮(萜类化合物)。它们的构建模块是属于烃的异戊二烯，即CH2＝C(CH3)-CH＝CH2(isoprene rule，Wallach 1887)。所以，萜烃具有分子式(C5H8)n，它们根据异戊二烯单元的数目被分为：
异戊二烯单元的数目
单萜 2
倍半萜 3
二萜 4
三萜 6
四萜 8
单萜的例子是：蒎烯，橙花醇，柠檬醛，樟脑，香叶醇，1，8-萜二烯。倍半萜的例子是：橙花叔醇，法呢醇。二萜的例子是：维生素A1(视黄醇)。角鲨烯是三萜的例子，胡萝卜素(维生素原A1)是四萜。
在本发明中，术语“萜类化合物”包括萜及其衍生物，它们具有至少一个C5H8烃单元，在其化学结构内具有一个或多个不饱和点。
萜类化合物是在许多工业中有用的有机化合物，特别是在树脂、香料、芳香剂等中。萜类化合物是许多香料和香味剂的芳香原料。芳香萜类化合物公开在Arctander，S.，
Perfume and Flavour Chemicals，第I、II卷，Allured Pub.Co.(1969)中，其例子包括Ambregris味化学品、茉莉酮、麝香、吡喃衍生物和檀香木香味化学品。
公知的是，香料或芳香原料的混合物当沉积在表面上或当引入化妆品组合物中时会丧失强度，并且会由于许多因素而随着时间改变特性。已经有许多尝试来使这些缺点最小化，但是至今很少成功。例如，Gardlick等在美国专利6147037中涉及用于向个人护理用品传递持久芳香的芳香传递体系。
芳香强度损失或特性改变的一个因素是萜是对氧化不稳定的。氧化不稳定性的程度取决于不饱和度，或在有机化合物中的双键或三键的数目。
氧化不稳定性是在萜类化合物中不希望有的特性。所以，需要一种能使萜类化合物对氧化稳定的试剂。特别是，需要一种能防止在其化学结构中具有至少一个双键的萜类化合物发生氧化的试剂。
因此，本发明的第一方面提供一种个人护理组合物，它含有：
a.约0.000001-10％的不饱和萜类化合物，
b.约0.000001-10％的4-取代间苯二酚衍生物，和
c.一种介质或载体。
合适的4-取代间苯二酚衍生物包括4-直链烷基间苯二酚、4-支链烷基间苯二酚、4-环烷基间苯二酚以及它们的混合物。优选的间苯二酚衍生物包括4-乙基间苯二酚、4-异丙基间苯二酚、4-丁基间苯二酚、4-环戊基间苯二酚和4-环己基间苯二酚，以及它们的酰化形式。
本发明的组合物在感官上令人愉快并具有改进的储存/氧化稳定性。
在这里使用的术语“化妆品组合物”表示用于局部施用到人皮肤上的组合物，包括免洗和需要洗除的产品。
在这里使用的术语“皮肤”包括面部、颈部、胸部、背部、臂部、腋部、手部、腿部和头皮上的皮肤。
在这里使用的术语“不饱和”表示具有双键或三键的有机化合物，例如烯烃或炔烃。
在这里使用的术语“香料”表示一种、但优选两种或多种的芳香原料，它们有技巧地组合在一起以赋予令人愉快的香气、气味、香味，或芳香特性。
除了在实施例中或另有说明，所有在此处表示材料的量或反应条件、材料的物理特性和/或应用的数字应该理解为包含“约”的情况。所有用量是以组合物的重量计，除非另有说明。
为了避免产生怀疑，术语“包含”表示包括但并非必须由其组成。换句话说，所列的步骤或选择不是穷举的。
我们已经发现4-取代间苯二酚衍生物可抑制不饱和萜类化合物的氧化。根据本发明，优选的是4-取代间苯二酚用于稳定在化妆品组合物中引入的不饱和萜类化合物。
间苯二酚衍生物是公知的化合物，可以例如通过如下的方法很容易地获得：使饱和羧酸和间苯二酚在氯化锌存在下缩合，所得的缩合物用锌汞齐/盐酸还原(Lille，J.Bitter，LA.Peiner.V，Tr.Nauch-Issled.Inst.Slantsev 1969，No.18，127)；或通过如下的方法获得：使间苯二酚和相应的烷基醇在氧化铝催化剂存在下在200-400℃的高温下反应(英国专利1581428)。
本发明的组合物通常含有约0.000001-50％的不饱和萜类化合物和约0.000001-50％的4-取代间苯二酚。本发明组合物的特别益处在于萜类化合物可以用4-取代间苯二酚进行抗氧化稳定。
在本发明中，萜类化合物是萜及其衍生物，在其化学结构中具有至少一个具有一个或多个不饱和点的C5H8烃单元。芳香萜类化合物描述在Bauer，K.，等的
Common Fragrance and Flavor Materials，VCHPublishers(1990)中。
可以引入本发明化妆品组合物中的萜类化合物分为三类，包括无环萜类化合物、环状萜类化合物和在结构上与萜类化合物有关的脂环族化合物。
在这三类中，萜衍生物包括醇、醚、醛、缩醛、酸、酮、酯以及含有杂原子例如氮或硫的萜化合物。
可以引入本发明组合物中的萜类化合物的例子列在下表中：
表1
无环萜类化合物
烃类
月桂烯
罗勒烯
β-法呢烯
醇类
二氢月桂烯醇 (2，6-二甲基-7-辛烯-2-醇)
香叶醇 (3，7-二甲基-反-2，6-辛二烯-1-醇)
橙花醇 (3，7-二甲基-顺-2，6-辛二烯-1-醇)
芳樟醇 (3，7-二甲基-1，6-辛二烯-3-醇)
月桂烯醇 (2-甲基-6-亚甲基-7-辛烯-2-醇)
熏衣草醇
香茅醇 (3，7-二甲基-6-辛烯-1-醇)
反-反-法呢醇 (3，7，11-三甲基-2，6，10-十二碳三烯-1-醇)
反-橙花叔醇 (3，7，11-三甲基-1，6，10-十二碳三烯-3-醇)
醛和缩醛
柠檬醛 (3，7-二甲基-2，6-辛二烯-1-醛)
柠檬醛二乙缩醛 (3，7-二甲基-2，6-辛二烯-1-醛二乙缩醛)
香茅醛 (3，7-二甲基-6-辛烯-1-醛)
香茅基氧基乙醛
2，6，10-三甲基-9-十一醛
酮
万寿菊酮
茄酮
香叶基丙酮 (6，10-二甲基-5，9-十一二烯-2-酮)
酸和酯
顺-香叶酸
香茅酸
香叶基酯，包括甲酸香叶基酯、乙酸香叶基酯、丙酸香叶基酯、异丁
酸香叶基酯、异戊酸香叶基酯；
橙花基酯，包括乙酸橙花基酯；
芳樟基酯，包括甲酸芳樟基酯、乙酸芳樟基酯、丙酸芳樟基酯、丁酸
芳樟基酯、异丁酸芳樟基酯；
熏衣草基酯，包括乙酸熏衣草基酯；
香茅基酯，包括甲酸香茅基酯、乙酸香茅基酯、丙酸香茅基酯、异丁
酸香茅基酯、异戊酸香茅基酯、惕各酸香茅基酯
含氮的不饱和萜衍生物
顺-香叶酸腈
香茅酸腈
表2
环状萜类化合物
烃类
1，8-萜二烯 (1，8-对-menthadiene)
α-萜品烯
γ-萜品烯 (1，4-对-menthadiene)
萜品油烯
α-水芹烯
β-水芹烯
α-蒎烯 (2-蒎烯)
β-蒎烯 (2(10)-蒎烯)
莰烯
3-蒈烯
石竹烯
(+)-朱栾倍半萜
罗汉柏烯
α-雪松烯
β-雪松烯
长叶烯
醇和醚
(+)-新异-异薄勒醇
异薄勒醇 (8-对-menten-3-ol)
α-萜品醇 (1-对-menten-8-ol)
β-萜品醇
γ-萜品醇
δ-萜品醇
1-萜品-4-醇 (1-对-menten-4-ol)
醛和酮
香芹酮 (1，8-对-mantadien-6-one)
α-芷香酮 (C13H20O)
β-芷香酮 (C13H20O)
γ-芷香酮 (C13H20O)
弋尾酮，α-、β-、γ- (C14H22O)
n-甲基紫罗兰酮，α-、β-、γ- (C14H22O)
异甲基紫罗兰酮，α-、β-、γ- (C14H22O)
烯丙基紫罗兰酮 (C16H24O)
假紫罗兰酮
n-甲基假紫罗兰酮
异甲基紫罗兰酮
突厥酮 1-(2，6，6-三甲基环己烯基)-2-丁烯-1-酮
包括β-大马烯酮 1-(2，6，6-三甲基-1，3-环己烯二基)-2-丁烯-
1-酮
诺卡酮 5，6-二甲基-8-异丙烯基双环[4.4.0]-1-癸烯-
3-酮
柏木甲基酮 (C17H26O)
酯
乙酸α-萜品烯 (乙酸1-对-menthen-8-基酯)
乙酸诺卜酯 乙酸(-)-2-(6，6-二甲基双环[3.1.1]-庚-2-
烯-2-基)乙基酯
乙酸khusymil酯
表3
结构上与萜相关的脂环族化合物
醇
5-(2，2，3-三甲基-3-环戊烯-1-基)-3-甲基戊-2-醇
醛
2，4-二甲基-3-环己烯甲醛
4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛
4-(4-羟基-4-甲基戊基)-3-环己烯甲醛
酮
灵猫酮
二氢茉莉酮 (3-甲基-2-戊基-2-环戊烯-1-酮)
顺-茉莉酮 3-甲基-2-(2-顺-戊烯-1-基)-2-环戊烯-1-酮
5-环十六碳烯-1-酮
2，3，8，8-四甲基-1，2，3，4，5，6，7，8-八氢-2-萘烯基甲基酮
3-甲基-2-环戊烯-2-醇-1-酮
酯
乙酸4，7-亚甲基-3a，4，5，6，7，7a-六氢-5-(或6)-茚基酯
3-环己基丙酸烯丙酯
二氢茉莉酮酸甲酯乙酸甲基(3-氧代-2-戊基环戊基)酯
优选地，萜类化合物在化妆品组合物中的量是约0.000001-10％，更优选约0.00001-5％，最优选约0.0001-2％。
如上所述，芳香强度损失或特性改变的一个因素是不饱和萜对氧化不稳定。
本发明组合物的稳定性通过使用一种抗氧化剂来实现，该抗氧化剂含有作为有效成分的下式(I)的4-取代间苯二酚衍生物：
其中每个R1和R2独立地表示氢原子、-CO-R(酰基)、-COO-R、CONHR；后三个基团分别由下式A表示：
其中R表示饱和或不饱和的、直链或支链或环状的C1-C18烃。在一个优选的实施方案中，R1和/或R2中的每一个或这两者代表氢。在一个更优选的实施方案中，R1和R2都代表氢。
R3代表：
(1)饱和或不饱和的、直链或支链或环状的C1-C18烃，优选C2-C12烃；或
(2)下面的通式，其中X和n应该如下定义
在上式(1)中，R3代表的基团优选具有2-12个碳原子，可以是直链或支链的，可以包括乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基和十二烷基。这些直链烷基的一个或多个氢原子可以被甲基或乙基取代。取代烷基的具体例子包括异丙基、异丁基、异戊基、2-甲基己基等。优选的烷基是其中R3代表乙基、丙基、异丙基、丁基、戊基、己基、庚基或辛基的那些。最优选的烷基间苯二酚是其中R3代表乙基、异丙基、丁基或己基的那些。
在上文所示其中R3代表上式(II)结构的通式(I)的间苯二酚衍生物中，间苯二酚衍生物称为4-环烷基间苯二酚，并由下式(III)表示：
在通式(III)(以及上式(II))中：
X表示氢；OR1，其中R1代表氢、(C1-C6)烷基或芳基-(C1-C6)烷基；OCOR2，其中R2代表(C1-C6)烷基、芳基-(C1-C6)烷基或苯基；卤素；(C1-C6)烷基；芳基-(C1-C6)烷基，或芳基-(C1-C6)烷基；或NHR1，其中R1如上所定义；
n是0-3，使得该结构是5、6、7或8元环；和
虚线表示在该位置上的任选双键。
4-环烷基间苯二酚的更具体的例子包括：
(a)式(III)的化合物，其中单键连接虚线处的两个碳原子；
(b)式(III)的化合物，其中n是1；
(c)式(III)的化合物，其中X是氢；
(d)式(III)的化合物，其中X是氢、甲基或乙基；
(e)式(III)的化合物，其中n是0；
(f)式(III)的化合物，其中n是2；和
(g)式(III)的化合物，其中X是苄氧基。
优选的式(III)化合物是4-环戊基间苯二酚、4-环己基间苯二酚、4-环庚基间苯二酚和4-环辛基间苯二酚。最优选的式(III)化合物是4-环己基间苯二酚和4-环戊基间苯二酚。
能有效抑制不饱和萜类化合物氧化的4-取代间苯二酚衍生物的量通过实验确定。不饱和萜类化合物和4-取代间苯二酚衍生物在组合物中以1∶10000至10000∶1的萜∶间苯二酚重量比存在，优选1∶1000至1∶5000，更优选1∶1至1∶1000。
间苯二酚衍生物的量是化妆品组合物总量的约0.00001-10％，优选约0.001-7％，最优选约0.01-5％。
本发明的化妆品组合物可以用于个人护理和个人洗涤产品中，例如洗剂、皂、除臭剂等。当被引入个人护理组合物中时，形成本发明组合物的萜类化合物和稳定剂可以具有其它有用的功能。
优选的个人护理组合物是适合于施用到人皮肤的那些，任选地、但优选地包括皮肤护理剂。合适的皮肤护理剂包括抗老化剂、抗皱剂、皮肤增白剂、抗痤疮剂和皮脂减少剂。这些的例子包括α-羟基酸和酯，β-羟基酸和酯，多羟基酸和酯，曲酸和酯，阿魏酸和阿魏酸酯衍生物，香草酸和酯，二元酸(例如癸二酸(sebacid)和壬二酸(azoleicacids))和酯，视黄醇、视黄醛、视黄基酯，氢醌，叔丁基氢醌，桑树提取物，甘草提取物，和除了这里所述4-取代间苯二酚衍生物之外的间苯二酚衍生物(从而起到萜类化合物氧化稳定性和护肤例如抗痤疮、增白皮肤或用于头发处理的双重作用)。
化妆上可接受的介质可以用作组合物中护肤成分的稀释剂、分散剂或载体，从而当将组合物施用到皮肤上时促进它们的分布。
介质可以是含水的、无水的或是乳液。优选的是，组合物是含水的或是乳液，特别是油包水或水包油乳液，优选水包油乳液。当存在水时，水的量可以是5-99重量％，优选20-70重量％，最好是40-70重量％。
除了水之外，挥发性较强的溶剂也可以用作本发明组合物中的载体。最优选的是一元C1-C3链烷醇。这些包括乙醇、甲醇和异丙醇。一元链烷醇的量可以是1-70重量％，优选10-50重量％，最好是15-40重量％。
润肤剂材料也可以用作化妆上可接受的载体。它们可以是硅油和合成酯的形式。润肤剂的量可以是0.1-50重量％，优选1-20重量％。
硅油可以分成挥发性和非挥发性的。这里使用的术语“挥发性”表示在环境温度(25℃)下具有可测量的蒸气压的那些材料。挥发性硅油优选选自环状或线型的聚二甲基硅氧烷，其含有3-9个、优选4-5个硅原子。线型挥发性硅氧烷材料通常具有在25℃下小于约5厘沲的粘度，而环状材料通常具有小于约10厘沲的粘度。用作润肤物质的非挥发性硅油包括聚烷基硅氧烷，聚烷基芳基硅氧烷和聚醚硅氧烷共聚物。在这里使用的基本非挥发性聚烷基硅氧烷包括例如在25℃下粘度为约5-25000000厘沲的聚二甲基硅氧烷。在本发明组合物中优选使用的非挥发性润肤剂是在25℃下粘度为约10-400厘沲的聚二甲基硅氧烷。
合适的酯类润肤剂是：
(1)具有10-20个碳原子的脂肪酸的链烯基或烷基酯。例子包括新戊酸异花生基酯、异壬酸异壬基酯、肉豆蔻酸油基酯、硬脂酸油基酯和油酸油基酯；
(2)醚酯，例如乙氧基化脂肪醇的脂肪酸酯；
(3)多元醇酯，包括乙二醇单-和二-脂肪酸酯，二甘醇单-和二-脂肪酸酯，聚乙二醇(200-6000)单-和二-脂肪酸酯，丙二醇单-和二-脂肪酸酯，聚丙二醇2000单油酸酯，聚丙二醇2000单硬脂酸酯，乙氧基化丙二醇单硬脂酸酯，甘油单-和二-脂肪酸酯，聚甘油聚脂肪酸酯，乙氧基化甘油单硬脂酸酯，1，3-丁二醇单硬脂酸酯，1，3-丁二醇二硬脂酸酯，聚氧乙烯多元醇脂肪酸酯，失水山梨醇脂肪酸酯，和聚氧乙烯失水山梨醇脂肪酸酯是满意的多元醇酯；
(4)蜡酯，例如蜂蜡、鲸蜡、肉豆蔻酸肉豆蔻酯，硬脂酸硬脂基酯和山俞酸花生基酯；和
(5)固醇酯，例子是胆固醇脂肪酸酯。
具有10-30个碳原子的脂肪酸也可以作为化妆上可接受的载体用于本发明的组合物。其例子是壬酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、异硬脂酸、羟基硬脂酸、油酸、亚油酸、蓖麻油酸、花生酸、山萮酸和芥酸。
多元醇型的润湿剂也可以作为化妆上可接受的载体用于本发明的组合物。润湿剂帮助增加润肤剂的效果、降低皮肤干燥和改进肤感。典型的多元醇包括甘油、聚亚烷基二醇和更优选亚烷基多元醇及其衍生物，包括丙二醇、二丙二醇、聚丙二醇、聚乙二醇和其衍生物、山梨醇、羟基丙基山梨醇、己二醇、1，3-丁二醇、1，2，6-己三醇、乙氧基化甘油、丙氧基化甘油以及它们的混合物。润湿剂的用量可以是组合物重量的0.5-30％，优选1-15％。
增稠剂也可以作为本发明组合物的化妆上可接受的载体的一部分。典型的增稠剂包括交联丙烯酸酯(例如Carbopol 982)、疏水改性的丙烯酸酯(例如Carbopol 1382)、纤维素衍生物和天然树胶。有用的纤维素衍生物是羧甲基纤维素钠、羟丙基甲基纤维素、羟丙基纤维素、羟乙基纤维素、乙基纤维素和羟甲基纤维素。适用于本发明的天然树胶包括瓜尔胶、黄原胶、菌核、卡拉胶、果胶以及这些树胶的组合物。增稠剂的用量可以是0.0001-50重量％，通常是0.001-1重量％，优选0.01-0.5重量％。
水、溶剂、硅氧烷、酯、脂肪酸、润湿剂和/或增稠剂一起将构成化妆上可接受的载体，其量通常是1-99.9重量％，优选80-99重量％。
油或油状物质可以与乳化剂一起形成油包水乳液或水包油乳液，这主要取决于所用乳化剂的平均亲水亲油平衡值(HLB)。
表面活性剂也可以存在于本发明的化妆品组合物中。对于免洗产品，表面活性剂的总浓度将是组合物重量的0.1-40％，优选1-20％，最好是1-5％。对于要洗除的产品，例如清洁剂和皂类，表面活性剂的总浓度将是约1-90％。表面活性剂可以选自阴离子、非离子、阳离子和两性的活性物质。
特别优选的非离子表面活性剂是具有以下的那些：以每摩尔疏水物质计与2-100摩尔氧化乙烯或氧化丙烯缩合的C10-C20脂肪醇或酸疏水物质；与2-20摩尔氧化烯缩合的C2-C10烷基酚；乙二醇的单-和二-脂肪酸酯；脂肪酸单甘油酯；失水山梨醇、单-和二-C8-C20脂肪酸；氧化乙烯/氧化丙烯的嵌段共聚物；和聚氧乙烯失水山梨醇以及它们的混合物。烷基多苷和多糖脂肪酰胺(例如甲基葡糖酰胺)也是合适的非离子表面活性剂。
优选的阴离子表面活性剂包括皂、烷基醚硫酸盐和磺酸盐，烷基硫酸盐和磺酸盐，烷基苯磺酸盐，烷基和二烷基磺基琥珀酸盐，C8-C20酰基羟乙基磺酸盐，酰基谷氨酸盐，C8-C20烷基醚磷酸盐，以及它们的混合物。
本发明的化妆品组合物任选地含有泡沫化表面活性剂。“泡沫化表面活性剂”表示这样的表面活性剂，当其与水混合并机械搅拌时，产生了泡沫或起泡。优选的是，泡沫化表面活性剂应当是温和的，这表示它必须提供足够的清洗或洗涤剂作用，但是不会过度使皮肤干燥，并且满足上述泡沫化标准。本发明的化妆品组合物可以含有浓度为约0.01-50％的泡沫化表面活性剂。
可以向常用的化妆品基料中加入UV吸收剂、UV分散剂(通常是细分散的氧化钛)、各种其它增塑剂、弹性体、菱锌矿、颜料、抗氧化剂、螯合剂和香料。
其它次要的助剂组分也可以引入本发明的化妆品组合物中。这些成分可以包括着色剂、不透明剂和香料。这些其它次要的助剂组分的用量可以是组合物重量的0.001-20％。
以下具体实施例进一步说明本发明，但是本发明不限于此。在所有实施例中，萜类化合物是从Aldrich Chemicals获得的。
实施例
实施例1
制备本发明范围内的化妆品组合物。
通过将相A成分在搅拌下加热到70-85℃来制备下表中显示的基本配料。相B成分在另一个容器中在搅拌下加热到70-85℃。然后，将相A加入到相B中，使这两相都保持在70-85℃。将该混合物在70-85℃搅拌至少15分钟，然后冷却。在50℃加入相C成分，然后在40℃下加入相D成分。
基本配料显示在下表4中。
表4
a b 相
组分
重量％
重量％
棕榈酸异硬脂基酯 6.00 6.00 A
辛酸C12-C15烷基酯 3.00 3.00 A
PEG100硬脂酸酯 2.00 2.00 A
羟基硬脂酸甘油酯 1.50 1.50 A
硬脂醇 1.50 1.50 A
硬脂酸 3.00 4.00 A
TEA，99％ 1.20 1.20 B
聚二甲基硅氧烷 1.00 1.00 A
单硬脂酸失水山梨醇酯 1.00 1.00 A
硅酸镁铝 0.60 0.60 B
维生素E乙酸酯 0.10 0.10 A
胆固醇 0.50 0.50 A
Simethicone 0.01 0.01 B
黄原胶 0.20 0.20 B
羟乙基纤维素 0.50 0.50 B
对羟基苯甲酸丙酯 0.10 0.10 A
EDTA二钠 0.05 0.05 B
芳香成分(不是萜类化合物) 0.50 0.50 D
烟酰胺 0.05 0.05 C
BHT 0.10 0.10 C
4-乙基间苯二酚 0.05 2.00 C
檀香醛(萜类化合物) 0.0005 0.001 D
对羟基苯甲酸甲酯 0.15 0.15 B
水
余量
余量 B
总量 100.00 100.00 B
实施例2
制备在本发明范围内的另一个化妆品组合物。
表5
| 组分 | 重量％ | 相 |
| 水，DI | 余量 | A |
| EDTA＝钠 | 0.05 | A |
| 硅酸镁铝 | 0.6 | A |
| 对羟基苯甲酸甲酯 | 0.15 | A |
| Simethicone | 0.01 | A |
| 1，3-丁二醇 | 3.0 | A |
| 羟乙基纤维素 | 0.5 | A |
| 甘油，USP | 2.0 | A |
| 黄原胶 | 0.2 | A |
| 三乙醇胺 | 1.2 | B |
| 硬脂酸 | 3.0 | B |
| 对羟基苯甲酸丙酯，NF | 0.1 | B |
| 羟基硬脂酸甘油酯 | 1.5 | B |
| 硬脂醇 | 1.5 | B |
| 棕榈酸异硬脂基酯 | 6.0 | B |
| 辛酸C12-C15烷基酯 | 3.0 | B |
| 聚二甲基硅氧烷 | 1.0 | B |
| 胆固醇，NF | 0.5 | B |
| 硬脂酸失水山梨醇酯 | 1.0 | B |
| 非萜类化合物芳香成分 | 1.0 | B |
| 乙酸生育酚酯 | 0.1 | B |
| PEG-100硬脂酸酯 | 2.0 | B |
| 硬脂酰基乳酸钠 | 0.5 | B |
| 羟基辛酸 | 0.1 | C |
| 4-环己基间苯二酚 | 10.0 | C |
| 芳樟醇 | 0.001 | D |
| BHT | 0.10 | C |
| 烟酰胺 | 0.05 | C |
| α-红没药醇 | 0.2 | C |
实施例2的组合物如下制备：
1、在搅拌下将相A加热到80℃。
2、在另一个容器中在搅拌下将相B加热到75℃。
3、将B加入A，并在70-80℃下热混合15分钟，然后停止加热，继续混合15分钟。
4、在50℃下加入相C，混合10分钟。
5、在40℃下加入相D，混合10分钟。
实施例3-10
通过实施例1的方法制备在本发明范围内的另一组化妆品组合物，并列在下表中。
表6
| 成分 | 相 | 实施例(重量％) | |||||||
| 3酸性皂基 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | ||
| 硬脂酸 | A | 17.9 | 17.9 | 17.9 | 17.9 | 17.9 | 17.9 | 17.9 | 17.9 |
| cetearyl基硫酸钠 | A | 2.2 | 1 | 1.5 | 2 | 3 | 2 | ||
| Myrj59 | A | 2 | 2 | 2 | 2 | 2 | 1 | ||
| 对羟基苯甲酸丙酯 | A | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| EDTA二钠 | A | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
| Span 60 | A | 2 | 2 | 2 | 2 | 2 | 1 | ||
| BHT | C | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 |
| 4-丁基间苯二酚 | C | 0.05 | 0.05 | 2.0 | 2.0 | 3.5 | 3.5 | 5.0 | 10.0 |
| 1，8-萜二烯和芳樟醇的混合物 | D | 0.001 | 0.001 | 0.01 | 0.01 | 0.5 | 0.5 | 0.001 | 0.01 |
| KOH，22％ | B | 2.20 | |||||||
| 甘油 | B | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
| 对羟基苯甲酸甲酯 | B | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
| 水 | B | 余量 | 余量 | 余量 | 余量 | 余量 | 余量 | 余量 | 余量 |
实施例11
典型芳香剂的萜成分的稳定性用含有4-取代间苯二酚衍生物的护肤组合物检测，以便确定间苯二酚对于防止老化和储存时的萜损失的效果。两种萜类化合物组分，即1，8-萜二烯和芳樟醇，作为护肤液中的芳香剂的一部分配制，该护肤液包含BHT(一种标准抗氧化剂)、未取代的间苯二酚、4-乙基间苯二酚和4-己基间苯二酚。这些芳香成分的稳定性使用GC/HS分析检测以测定在常规消费产品储存条件(于40℃和在室温下在日光下储存5个月)下每个萜类化合物分子随着时间的损失。在不含“抗氧化剂”的标准配料中，1，8-萜二烯和芳樟醇的损失直接与这些含有BHT、未取代的间苯二酚和4-取代间苯二酚衍生物的材料比较。配料显示在表7中，稳定性数据显示在表8中。
参考下表中的数据，在Agilent 6890 GC/5973MS上使用GerstelMPS2 Headspace Sampler进行GC/HS检测。将这些样品在35℃下培育1小时，然后将样品之上的2.50ml空间注入Agilent Technologies序号19091S-433、HP-5MS、5％苯基甲基硅氧烷柱上，该柱具有30m×0.25mm ID，膜厚度是0.25微米。记录两个芳香组分的峰面积作为GC数据。
在下表中显示的配料按照实施例1的方法制备。
表7护肤液配料
| #1 | #2 | #3 | #4 | #5 | ||
| 原料 | 重量％ | 重量％ | 重量％ | 重量％ | 重量％ | |
| 硬脂酸 | A | 17.90 | 17.90 | 17.90 | 17.90 | 17.90 |
| 十六醇十八醇混合物 | A | 0.53 | 0.53 | 0.53 | 0.53 | 0.53 |
| 聚二甲基硅氧烷(DC200，350cSt) | A | 0.50 | 0.50 | 0.50 | 0.50 | 0.50 |
| Parsol MCX | A | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 |
| Parsol 1789 | A | 0.40 | 0.40 | 0.40 | 0.40 | 0.40 |
| 对羟基苯甲酸丙酯 | A | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 |
| 水 | B | 55.88 | 55.88 | 55.88 | 55.88 | 55.88 |
| 甘油 | B | 1.00 | 1.00 | 1.00 | 1.00 | 1.00 |
| EDTA | B | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 |
| 对羟基苯甲酸甲酯 | B | 0.20 | 0.20 | 0.20 | 0.20 | 0.20 |
| KOH，22％ | B | 2.20 | 2.20 | 2.20 | 2.20 | 2.20 |
| 香料(含有20％1，8-萜二烯和20％芳樟醇) | D | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 |
| 烟酰胺 | C | 1.00 | 1.00 | 1.00 | 1.00 | 1.00 |
| BHT | C | 0.10 | ------- | --------- | -------- | -------- |
| 4-乙基间苯二酚 | C | --------- | 3.55 | --------- | -------- | -------- |
| 4-己基间苯二酚 | C | --------- | -------- | 5.00 | ------- | -------- |
| 间苯二酚 | C | --------- | -------- | ------- | 2.84 | -------- |
| 适量用水加至100％ 适量 适量 适量 适量 适量 | ||||||
表8在配料中的1，8-萜二烯和芳樟醇的稳定性
| 配料编号 | 初始GC/HS | 日光下5个月GC/HS | 损失％ | 稳定％ | 40℃下5个月GC/HS | 损失％ | 稳定％ | |
| 5 | 对比 | |||||||
| 1，8-萜二烯 | 51812033 | 36654323 | 29.2 | 26830284 | 48.2 | |||
| 芳樟醇 | 8109405 | 5054708 | 37.6 | 4878857 | 39.8 | |||
| BHT样品 | ||||||||
| 1，8-萜二烯 | 38342803 | 32465677 | 15.3 | 48 | 26286287 | 31.7 | 35 | |
| 芳樟醇 | 6853529 | 4678449 | 31.4 | 16.5 | 4918953 | 28.2 | 29 | |
| 2 | 4-乙基间苯二酚 | |||||||
| 1，8-萜二烯 | 54736538 | 54753996 | 0 | 100 | 46790409 | 12.9 | 74 | |
| 芳樟醇 | 3288967 | 2650924 | 19.4 | 49 | 2292953 | 30.2 | 25 | |
| 3 | 4-己基间苯二酚 | |||||||
| 1，8-萜二烯 | 40778538 | 34662250 | 7.7 | 84 | 3381932 | 18.5 | 72 | |
| 芳樟醇 | 2222930 | 1666185 | 7.5 | 80 | 1466948 | 10.2 | 75 | |
| 4 | 间苯二酚 | |||||||
| 1，8-萜二烯 | 45478209 | 25743642 | 43.4 | 0 | 19260141 | 57.6 | 0 | |
| 芳樟醇 | 6088780 | 3856563 | 36.7 | 3 | 4286137 | 29.6 | 26 |
上表的数据显示，与BHT相比，4-取代间苯二酚能够同样有效地或者甚至更好地在一些情况下用于稳定萜类化合物分子以抗降解，而未取代的间苯二酚几乎没有提供稳定这些芳香成分的作用。在大多数情况下，不合抗氧化剂的“对比”配料或含有未取代间苯二酚的“对比”配料损失的1，8-萜二烯和/或芳樟醇是含有4-取代间苯二酚的配料的两倍。这些结果表明了添加4-取代间苯二酚对于萜类化合物稳定性有显著的额外益处。
应当理解的是，这里描述的本发明的具体形式仅仅用于说明。可以在不明显偏离公开内容下的改变，包括但不限于在本说明暗示的那些。因此，应当参考所附的权利要求确定本发明的整个范围。
Claims (11)
1、一种个人护理组合物，它含有：
a.约0.000001-10％的不饱和萜类化合物，
b.约0.000001-10％的通式(I)的4-取代间苯二酚衍生物：
其中每个R1和R2独立地选自氢原子、-CO-R、-COO-R和CONHR；其中R表示C1-C18烃；R3代表C1-C18烃或具有通式(II)：
其中X表示氢；OR1，其中R1代表氢、(C1-C6)烷基或芳基-(C1-C6)烷基；OCOR2，其中R2代表(C1-C6)烷基、芳基-(C1-C6)烷基或苯基；卤素；(C1-C6)烷基；芳基-(C1-C6)烷基，或芳基-(C1-C6)烷基；或NHR1，其中R1如上所定义；
n是0-3，使得通式II的结构是5、6、7或8元环；和
虚线表示在该位置上的任选双键；和
c.化妆品可接受的介质。
2、权利要求1的组合物，其中萜类化合物选自无环萜类化合物，环状萜类化合物，在结构上与萜类化合物相关的脂环族化合物，以及它们的混合物。
3、权利要求1或2的组合物，其中萜类化合物包括萜和萜衍生物，所述萜衍生物选自醇、醛、缩醛、酮、酸、酯以及含有选自氮或硫的杂原子的萜化合物，以及它们的混合物。
4、权利要求2或3的组合物，其中无环萜类化合物选自月桂烯，罗勒烯，β-法呢烯，二氢月桂烯醇，香叶醇，橙花醇，芳樟醇，月桂烯醇，熏衣草醇，香茅醇，反-反-法呢醇，反-橙花叔醇，柠檬醛，柠檬醛二乙缩醛，香茅醛，香茅基氧基乙醛，2，6，10-三甲基-9-十一醛，万寿菊酮，茄酮，香叶基丙酮，顺-香叶酸，香茅酸，甲酸香叶基酯、乙酸香叶基酯、丙酸香叶基酯、异丁酸香叶基酯、异戊酸香叶基酯，乙酸橙花基酯，甲酸芳樟基酯、乙酸芳樟基酯、丙酸芳樟基酯、丁酸芳樟基酯、异丁酸芳樟基酯、乙酸熏衣草基酯、甲酸香茅基酯、乙酸香茅基酯、丙酸香茅基酯、异丁酸香茅基酯、异戊酸香茅基酯、惕各酸香茅基酯，顺-香叶酸腈，香茅酸腈，以及它们的混合物。
5、权利要求2-4任一项的组合物，其中环状萜类化合物选自1，8-萜二烯，α-萜品烯，γ-萜品烯，萜品油烯，α-水芹烯，β-水芹烯，α-蒎烯，β-蒎烯，莰烯，3-蒈烯，石竹烯，(+)-朱栾倍半萜，罗汉柏烯，α-雪松烯，β-雪松烯，长叶烯，(+)-新异-异薄勒醇，异薄勒醇，α-萜品醇，β-萜品醇，γ-萜品醇，δ-萜品醇，1-萜品-4-醇，香芹酮，α-芷香酮，β-芷香酮，γ-芷香酮，α-弋尾酮，β-弋尾酮，γ-弋尾酮，α-n-甲基紫罗兰酮，β-n-甲基紫罗兰酮，、γ-n-甲基紫罗兰酮，α-异甲基紫罗兰酮，β-异甲基紫罗兰酮，γ-异甲基紫罗兰酮，烯丙基紫罗兰酮，假紫罗兰酮，n-甲基假紫罗兰酮，异甲基假紫罗兰酮，突厥酮，大马烯酮，诺卡酮，柏木甲基酮，乙酸α-萜品烯，乙酸诺卜酯，乙酸Khusymil酯，以及它们的混合物。
6、权利要求2-5任一项的组合物，其中结构上与萜相关的脂环族化合物选自5-(2，2，3-三甲基-3-环戊烯-1-基)-3-甲基戊-2-醇，2，4-二甲基-3-环己烯甲醛，4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛，4-(4-羟基-4-甲基戊基)-3-环己烯甲醛，灵猫酮，二氢茉莉酮，顺-茉莉酮，5-环十六碳烯-1-酮，2，3，8，8-四甲基-1，2，3，4，5，6，7，8-八氢-2-萘烯基甲基酮，3-甲基-2-环戊烯-2-醇-1-酮，乙酸4，7-亚甲基-3a，4，5，6，7，7a-六氢-5-(或6)-茚基酯，3-环己基丙酸烯丙酯，二氢茉莉酮酸甲酯，乙酸甲基(3-氧代-2-戊基环戊基)酯，以及它们的混合物。
7、前述权利要求任一项的组合物，其中4-取代间苯二酚衍生物以至少能抑制不饱和萜类化合物氧化的有效量存在。
8、前述权利要求任一项的组合物，其中4-取代间苯二酚选自4-直链烷基间苯二酚、4-支链烷基间苯二酚、4-环烷基间苯二酚以及它们的混合物。
9、前述权利要求任一项的组合物，其中4-取代间苯二酚选自4-甲基间苯二酚、4-乙基间苯二酚、4-丙基间苯二酚、4-丁基间苯二酚、4-戊基间苯二酚、4-己基间苯二酚、4-庚基间苯二酚、4-辛基间苯二酚、4-壬基间苯二酚、4-癸基间苯二酚、4-环戊基间苯二酚、4-环己基间苯二酚、4-环庚基间苯二酚、4-环辛基间苯二酚、以及它们的混合物。
10、前述权利要求任一项的化妆品组合物，其还包含一种护肤剂，选自α-羟基酸和酯，β-羟基酸和酯，多羟基酸和酯，曲酸和酯，阿魏酸和阿魏酸酯衍生物，香草酸和酯，二元酸和酯，视黄醇、视黄醛、视黄基酯，氢醌，叔丁基氢醌，间苯二酚衍生物，以及它们的混合物。
11、一种化妆品组合物，它包含：
a.被4-取代间苯二酚衍生物稳定的不饱和萜类化合物；
b.护肤剂，和
c.化妆上可接受的介质；
其中萜类化合物的存在量是该化妆品组合物的约0.0001-5重量％；和
其中萜类化合物与4-取代间苯二酚衍生物的重量比是约10000∶1至约1∶100000。
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| PCT/EP2003/002658 WO2003080011A1 (en) | 2002-03-22 | 2003-03-13 | Stabilization of terpenoids in cosmetic compositions |
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| JP3217299B2 (ja) * | 1996-07-26 | 2001-10-09 | 松下電器産業株式会社 | 半導体集積回路のレイアウト方法 |
| US6147037A (en) * | 1996-08-19 | 2000-11-14 | The Procter & Gamble Company | Fragrance delivery systems |
| US5961961A (en) * | 1998-06-04 | 1999-10-05 | Chesebrough-Pond's Usa Co. | Sunscreen cosmetic composition |
| JP2000016917A (ja) | 1998-07-01 | 2000-01-18 | Shiseido Co Ltd | 美白化粧料 |
| JP4814409B2 (ja) * | 1998-07-22 | 2011-11-16 | 昭 神谷 | シャンプー組成物 |
| JP4358957B2 (ja) * | 2000-01-21 | 2009-11-04 | 三井製糖株式会社 | フリーラジカル又は活性酸素を消去もしくは低減する剤 |
| JP4615671B2 (ja) * | 2000-04-20 | 2011-01-19 | ポーラ化成工業株式会社 | 炎症存在下使用用のしわ形成又は皮膚の弾力喪失の防止剤 |
| JP3623430B2 (ja) * | 2000-07-06 | 2005-02-23 | 築野ライスファインケミカルズ株式会社 | 抗酸化性組成物 |
-
2003
- 2003-03-11 US US10/386,258 patent/US6858217B2/en not_active Expired - Lifetime
- 2003-03-13 CN CN038067463A patent/CN1642523B/zh not_active Expired - Lifetime
- 2003-03-13 WO PCT/EP2003/002658 patent/WO2003080011A1/en active Application Filing
- 2003-03-13 JP JP2003577842A patent/JP2005526093A/ja active Pending
- 2003-03-13 AU AU2003208708A patent/AU2003208708A1/en not_active Abandoned
- 2003-03-13 BR BRPI0307541-9A patent/BR0307541B1/pt active IP Right Grant
- 2003-03-13 KR KR1020047014630A patent/KR100959717B1/ko active IP Right Grant
- 2003-03-13 MX MXPA04008843A patent/MXPA04008843A/es active IP Right Grant
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107530231A (zh) * | 2015-04-23 | 2018-01-02 | 宝洁公司 | 低粘度毛发护理组合物 |
| CN109152713A (zh) * | 2016-05-12 | 2019-01-04 | 荷兰联合利华有限公司 | 稳定视黄酸前体的方法和具有稳定视黄酸前体的皮肤有益组合物 |
| US11324679B2 (en) | 2016-05-12 | 2022-05-10 | Conopco, Inc. | Method for stabilizing retinoic acid precursors and a skin benefit composition with stabilized retinoic acid precursors |
| US11826449B2 (en) | 2016-05-12 | 2023-11-28 | Conopco, Inc. | Method for stabilizing retinoic acid precursors and a skin benefit composition with stabilized retinoic acid precursors |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030185867A1 (en) | 2003-10-02 |
| BR0307541A (pt) | 2004-12-07 |
| US6858217B2 (en) | 2005-02-22 |
| AU2003208708A1 (en) | 2003-10-08 |
| KR100959717B1 (ko) | 2010-05-25 |
| MXPA04008843A (es) | 2004-11-26 |
| WO2003080011A1 (en) | 2003-10-02 |
| JP2005526093A (ja) | 2005-09-02 |
| CN1642523B (zh) | 2012-10-10 |
| BR0307541B1 (pt) | 2014-03-11 |
| KR20040106294A (ko) | 2004-12-17 |
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