CN107249553B - 包含碳水化合物偏酯的组合物 - Google Patents
包含碳水化合物偏酯的组合物 Download PDFInfo
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- CN107249553B CN107249553B CN201580075871.2A CN201580075871A CN107249553B CN 107249553 B CN107249553 B CN 107249553B CN 201580075871 A CN201580075871 A CN 201580075871A CN 107249553 B CN107249553 B CN 107249553B
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Abstract
本发明涉及一种包含碳水化合物偏酯的组合物、其制备方法和包含要求保护的碳水化合物偏酯的产品。
Description
本发明涉及一种包含碳水化合物偏酯的组合物、其制备方法和包含本发明碳水化合物偏酯的产品。
用于制备碳水化合物偏酯的方法由EP 1 811 951 A1、EP 0 885 898 B1、GB 1399 053和GB 1 499 989已知。该制备基本上基于碳水化合物与脂肪酸烷基酯或甘油酯的催化酯交换。酯交换后的粗产物的纯化或后处理描述于WO 90 11285A或JP 383 6162B2中。
通常在碱性催化剂的存在下通过在120-160℃的温度下糖与脂肪酸甲酯的酯交换而制备碳水化合物偏酯。加入溶剂和/或软化剂后,冷却至60-130℃后通过倾析和过滤分离出未反应的糖。
为了有效的后处理,通常将导致粘度降低并因此也导致使得在较低温度下通过倾析和过滤快速分离剩余的糖成为可能的辅助物质加入粗产物中。在此优选使用惰性烃如氢化聚异丁烯。如果用于降低粘度的辅助物质(软化剂)在后处理条件下是反应性的,则必须使酯交换催化剂完全失活。在后处理条件下具有反应性的软化剂是例如脂肪醇或酯油。如果催化剂不完全失活,则进行进一步的酯交换反应,使得发现碳水化合物偏酯的分布改变。
此外,在粗产物中也存在未反应的脂肪酸酯,例如上述脂肪酸甲酯或其他具有短链醇组分的酯油,其基于其反应性用作合成碳水化合物偏酯中的离析物。
使用具有较长链醇组分的酯作为软化剂一方面降低了在后处理期间酯交换的反应性,而且另一方面增加了粘度。由于粘度的增加,后处理,特别是过滤必须在显著更高的温度下进行。为了避免更高的温度和降低粘度,必须进一步增加软化剂的含量。粘度的增加和软化剂含量的增加降低了后处理步骤的效率。烃类软化剂通常不利地影响锭剂的性能。
此外,从工艺技术方面,催化剂的完全失活难以实现,并且代表了一个额外的工艺步骤。由于通常使用碱性酯交换催化剂,所以失活通过加入酸而进行,并且通常仅不完全地实现失活。
辅助物质,例如上述额外的软化剂或酸的加入不利地影响粗产物的颜色和酸含量。
本发明的目的是克服现有技术的缺点,特别是就粗产物的后处理而言的缺点。
为此,提供用于制备碳水化合物偏酯和用于后处理粗产物的方法,其由于少的工作步骤数而高效。这应该是无溶剂和低废物的方法。在此特别重要的是在碳水化合物偏酯混合物的合成已经结束之后,粗产物的碳水化合物偏酯的分布与纯化或后处理终产物中的碳水化合物偏酯的分布没有不同。此外,在该方法中,通过使用的软化剂,达到如下粘度,其一方面使得通过过滤和/或倾析,优选仅在一个分离步骤中有效分离剩余的糖(未反应的碳水化合物)成为可能。另一方面,与烃相比,由于稀释剂的极性较高,避免相对大量的剩余的糖(部分)溶解。
本发明的另一目的是提供包含碳水化合物偏酯的组合物。该组合物具有精确限定的偏酯分布,其不会由于后处理或储存而改变。此外,就颜色、稳定性和粘度而言,组合物应满足直接进一步加工的所有要求,特别是用于化妆品或药物配制剂中。优选地,组合物应基本上或仅由可持续的原料组成。在其中应避免或不包含石油化工来源的烃。此外,包含本发明组合物或基本上由其组成的成形体就稠度、颜色和气味而言具有更好的保存期限。成形体必须足够硬并且不粘在一起,以使得即使在较长的储存期间也避免结块。即使在不利的储存条件(例如提高的温度)下,软化剂也不应从成形体中脱离。脆性成形体具有降低的稳定性并导致灰分的形成。要避免加入额外的辅助物质,特别是用于稳定成形体的辅助物质。
这些目的通过根据权利要求的组合物、成形体和方法而实现。本发明提供一种组合物,其包含:
a1)作为具有式R1-COO的酰基组分的至少一种碳水化合物的酯化产物的碳水化合物偏酯,
b1)式R1-COO-R2的烷基酯,和
c1)式R1-COO-R3的酯油,
和任选地一种或多种选自包含碳水化合物、脂肪酸、脂肪皂、水和催化剂或由其组成的组的化合物;
其中酯油c1)具有选自如下的醇组分R3
i)具有C8-C22,优选C10-C20,特别优选C12或C14-C20,特别是C16和/或C18的支化和非支化醇,或
ii)多元醇,或
iii)其混合物
将其用选自链长度为C6-C22,优选C10-C20,特别优选C12或C14-C20,特别是C16和/或C18的单酸和二酸或任何所需组合的酰基组分R1完全酯化。
本发明还提供一种组合物,其包含:
a2)平均酯化度为1-4的碳水化合物偏酯,
b2)具有含有6-22个碳原子,优选C10-C20,特别优选C12或C14-C20,特别是C16和/或C18的酰基组分的有机烷基酯,
c2)具有含有6-22个碳原子,优选C10-C20,特别优选C12或C14-C20,特别是C16和/或C18的直链酰基组分和含有8-22个碳原子,优选C10-C20,特别优选C12或C14-C20,特别是C16和/或C18的直链醇组分的酯油,
和任选地一种或多种选自包含碳水化合物、脂肪酸、脂肪皂、水和催化剂或由其组成的组的化合物。
在一个实施方案中,本发明组合物包含:
a)平均酯化度为1-4的碳水化合物偏酯,其比例为50-90%,优选55-80%,特别优选55-70%,特别是55-65%;
b)具有6-30个碳原子的酰基组分的有机烷基酯,其比例为0-10%,优选2.5-7.5%,特别优选3-5%,特别是4%或5%;
c)酯油,其比例为5-30%,优选10-20%,特别优选12-17%,特别是15%;和任选地碳水化合物(剩余糖),其比例为0-10%,优选3-8%,特别是3-5%;和/或
任选地脂肪皂,其比例为0-20%,优选1-15%,特别优选5-12%,特别是10%或12%和/或任选地
脂肪酸:0-10%,优选2.5-7.5%,特别优选3-5%,特别是4%或7%。化合物或组分a)、b)和c)在每种情况下分别表示a1)和/或a2)、b1)和/或b2)或者c1)和/或c2)。
本发明组合物可以包含5%,优选2%,特别优选1%,特别是0.5-1%或更少的比例的水,或可以基本上或完全无水。“基本上无水”是指组合物的水含量为<5重量%,优选<2重量%,优选<1重量%,特别是<0.1重量%。“完全无水”是指水含量在用于定量测定水的常规和已知方法的检测限以下。
本发明组合物可以包含5%,优选2%,特别优选1%,特别是0.5%或更少的碳水化合物(剩余糖),或可以基本上或完全不含碳水化合物。“基本上不含碳水化合物”是指组合物的碳水化合物含量为<5重量%,优选<2重量%,优选<1重量%,特别是<0.1重量%。“完全不含碳水化合物”是指碳水化合物含量在用于定量测定水的常规和已知方法的检测限以下。
本发明组合物的化合物或组分的总量在每种情况下为100%。
在一个实施方案中,产物a1)或a2)是糖与b1)或b2)酰基组分的碳水化合物偏酯。
糖包括多羟基醛(醛糖)和多羟基酮(酮糖),也称为碳水化合物,以及可通过水解转化成这类物质的较高分子量化合物。在本发明的上下文中,可以将单体多羟基醛或多羟基酮(单糖)或其二聚体至十聚体(二糖、三糖、寡糖)用作糖。可能的单糖(也称为“简单糖”)是例如乙糖、丙糖、丁糖、戊糖、己糖、庚糖等。戊醛糖的典型实例是D-核糖、D-木糖和L-阿拉伯糖。最重要的己醛糖包括D-葡萄糖、D-甘露糖和D-半乳糖;应提及己酮糖,D-果糖和山梨醇糖。6-脱氧糖、L-岩藻糖和L-鼠李糖同样是广泛使用的己糖,也是可能的起始物质。适合作为起始物质的最简单的寡糖是二糖。优选使用蔗糖(甘蔗糖、甜菜糖)、乳糖(lactose,milchzucker)和/或麦芽糖(maltose,malzzucker)。
就该方法而言优选使用单糖和/或二糖;特别优选使用蔗糖(saccharose,sucrose)或葡萄糖。
在本发明的一个实施方案中,酯b1)或b2)的醇组分是C1-C3醇单元,优选甲基和/或乙基。
在一个实施方案中,存在至少一种烷基酯b2)和/或b1),其具有选自具有6-22个碳原子以及0和/或1、2或3个双键的脂族、直链或支化酰基的酰基组分。此外,酰基组分选自己酸、辛酸、2-乙基己酸、癸酸、月桂酸、异十三烷酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、异硬脂酸、油酸、反油酸、岩芹酸、亚油酸、亚麻酸、桐酸、花生酸、顺式二十碳烯酸、山萮酸和芥酸及其工业级混合物与甲醇、乙醇、丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、正戊醇和异戊醇或其工业级混合物的酰基的酰基组分,其例如在天然脂肪和油的加压裂解中,在由Roelen的羰基合成的醛的还原中或不饱和脂肪酸的二聚获得。优选具有12-18个碳原子的工业级脂肪酸,例如椰油酸、棕榈酸、棕榈仁酸或牛油脂肪酸等。
在一个方案中,使用具有12-30个C原子,优选具有16-24个C原子的直链饱和酰基的烷基酯b1)和/或b2)。C16-C24脂肪酸甲酯,特别是C16-C20脂肪酸甲酯是优选的,其中根据本发明特别优选其中的直链和非支化的酯。根据本发明,使用C16脂肪酸甲酯和/或C18脂肪酸甲酯或C16/C18脂肪酸甲酯的任何所需混合物(例如C16/C18含量为50:50,40:60,30:70,60:40或70:30)是有利的。
在一个本发明方法以及本发明组合物和成形体的优选实施方案中,所有组分,即碳水化合物偏酯a)、烷基酯b)和酯油c)因此具有相同的酰基组分R1,即碳长度为C16和C18的脂肪酸基团的混合物。
在一个方案中,使用异硬脂酸的酯。
所用的烷基酯:碳水化合物的摩尔使用比优选为至少0.5,特别是0.5-2.5,特别优选0.6-2.0。在较低的摩尔比下,反应产物的着色增加且为粘稠的,这可能归因于糖的焦糖化。根据本发明,为了减少糖的焦糖化并获得颜色较浅的粗产物,特别优选摩尔比为1.3-1.6,特别是1.4-1.55。
在另一实施方案中,酯a1)、b1)、c1)、a2)、b2)或c2)的至少一种酰基组分是具有16和/或18个碳原子的脂肪酸基团。
在一个替换方案中,酯a1)、b1)、c1)、a2)、b2)或c2)的所有酰基组分是相同的。
在另一替换方案中,酯a1)、b1)、c1)、a2)、b2)或c2)的所有酰基组分是具有16和/或18个碳原子的脂肪酸基团,优选全部相同。
本发明的一个实施方案涉及一种组合物,其特征在于酯油c1)或c2)的醇组分是具有16和/或18个碳原子的脂肪醇或具有16-20个碳原子的格尔伯特醇。
在一个替换方案中,使用棕榈酸鲸蜡酯(例如Cutina CP)作为酯油c1)和/或c2)。
在另一替换方案中,使用棕榈酸鲸蜡酯(例如Cutina CP)、硬脂酸格尔伯特己基癸醇酯(例如Eutanol G16S)和/或氢化棕榈脂肪甘油三酯(例如Waretta 863)作为酯油c1)。通过相应的油中的不饱和脂肪酸的双键(部分)氢化而获得氢化棕榈油(palmfett),其特征尤其在于通过提高的熔点和改进的氧化稳定性。
组合物的一个替换方案的特征在于酯油c1)或c2)的醇组分是选自包含以下/由以下组成的组的多元醇:乙二醇、丙二醇、丁二醇、新戊二醇(NPG、TMP、PE)、甘油。可以使用的新戊二醇是2,2-二甲基-1,3-丙二醇=NPG、三羟甲基丙烷=TMP或季戊四醇=PE。
优选地,多元醇被完全酯化。在一个实施方案中,甘油以完全酯化的形式使用。
在一个方案中,根据本发明可以使用具有6-22个碳原子以及0和/或1、2或3个双键的脂族直链或支化烃基作为醇组分。
选自包含C16-和/或C18-脂肪醇,C16-、C18-和/或C20-格尔伯特醇或由其组成的组的脂肪醇和/或格尔伯特醇是优选的。
在一个替换方案中,醇组分选自包含以下或由以下组成的组:己醇、辛醇、2-乙基己醇、癸醇、2-丙基庚醇、月桂醇、异十三烷醇、肉豆蔻醇、鲸蜡醇、棕榈油醇、硬脂醇、异硬脂醇、油醇、反油醇、岩芹醇、亚油醇、亚麻醇、桐醇、花生醇、顺式二十碳烯醇、山萮醇、瓢儿菜醇和巴西烯醇(barssidylalkohol)及其工业级混合物,其例如基于在脂肪和油的工业级甲基酯或来自Roelen的羰基合成的醛的高压氢化中并且作为不饱和脂肪醇的二聚中的单体级份获得。具有12-18个碳原子的工业级脂肪醇如椰油醇、棕榈醇、棕榈仁醇或牛油脂肪醇是优选的。
在一个方案中,组合物不含酯油的游离醇组分。
在一个方案中,组合物不含酯油的游离偏甘油酯。
在另一实施方案中,本发明组合物包含各种碳水化合物偏酯。
在一个替换方案中,
单酯以0-20%,优选5-15%,特别优选7-12%,特别是7%或8%的比例存在;
二酯以10-40%,优选20-35%,特别优选25-30%,特别是24%或27%的比例存在;
三酯以20-50%,优选30-45%,特别优选35-40%,特别是33%或37%的比例存在,以及
四酯和高级酯以15-40%,优选20-40%,特别优选25-35%,特别是26%或29%的比例存在,其中总和为100%。
在另一替换方案中,单酯:二酯:三酯:四酯的比例为0.5-1.5:3.0-4.0:4.0-5.0:3.0-4.0,优选1:3.5:4.7:3.7,特别优选1:3.4:(4.6或4.7):(3.6或3.7)。
在一个实施方案中,通过GPC测定碳水化合物偏酯分布。该测定优选如下进行:
原理:将样品溶于四氢呋喃中,通过液相色谱法分离,并用RI检测器检测。面积百分比量化基于根据Ph.Eur.monograph of glycerol monostearate type II,方法2.2.30和DGF C-VI 5b(02)的评估方法。
设备:HPLC系统,具有RI检测器,例如Acquity System from Waters;RI检测器;Empower评估软件;2X PLgel 5μm100A 30cm*8mm Dr.Maisch
HPLC条件:
分离柱:PLgel 5μm 100A 30cm*8mm Dr.Maisch
洗脱剂:四氢呋喃
流速:1.0ml/min,在25℃下,等度洗脱
注射器:50μl
检测器:RI,在40℃下
测定程序:
在分析天平上将约0.5g样品分析精确地称入50ml容量瓶中,并用甲酸酸化。容量瓶用四氢呋喃加满至标记处。混合物通过振摇而均化。经后处理的本发明组合物的粘度在100℃和100/s的剪切速率下为0.5-3Pa·s,优选1.0-2.0Pa·s,特别优选1.2-1.5Pa·s,特别是1.3Pa·s。在一个方案中,通过来自Bohlin的V-VOR 120流变仪(4°和40mm的锥/板粘度计),在100℃和100/s的剪切速率下以动态流动平衡测定粘度。本发明还提供了一种成形体,其包含本发明组合物或由其组成。本发明成形体除了本发明组合物之外还可包含其他碳水化合物偏酯。在一个替换方案中,它们还包含适用于化妆品用途的碳水化合物偏酯的软化剂和/或1-10重量%的C16-C40脂肪醇或这些脂肪醇的任何所需混合物,其中其他辅助物质和添加剂的含量为至多20重量%。
在一个实施方案中,为了进一步处理,将碳水化合物偏酯溶解在C16-C40脂肪醇,优选C18-C30脂肪醇,特别优选C20-C24脂肪醇或这些脂肪醇的任何所需混合物中。
在一个替换方案中,本发明组合物和/或本发明成形体不含C16-C40脂肪醇,优选不含C18-C30脂肪醇,特别优选不含C20-C24脂肪醇,或不含这些脂肪醇的任何所需混合物。
成形体的一个优选实施方案包含10-95重量%的碳水化合物偏酯或碳水化合物偏酯的混合物a),5-20重量%的适用于化妆品用途的软化剂,优选酯油c)和辅助物质和添加剂,其中其他辅助物质和添加剂的含量为至多10重量%。优选地,其他辅助物质和添加剂的含量小于总组合物的10重量%,特别是小于5重量%。非常特别优选地,其他辅助物质和添加剂的比例仅限于由于反应而包含在产物混合物中的副产物。
成形体是储存稳定的且即使在40℃下在储存长于一周,优选1个月,特别优选6个月,特别是1年期间不显示出“发汗”,即没有发生导致在锭剂表面或容器壁上形成液体的(连续)膜的液体产物组分分离。“发汗”是不希望的,因为它使产品的处理困难并损害其外观。
为了研究保存期限,将15ml锭剂引入钢瓶中,并装入重量为900g的测试压杵(Prüfstempel),并在40℃下以该设置储存一天。如果保存期限良好,则获得的试样在室温下在没有大的外力作用下崩解。
在一个替换方案中,成形体为锭剂和/或薄片。
锭剂由固化的熔体或固溶体以单剂量形式组成。它们具有与在压片机上由粉末或颗粒在压制压力下产生的片剂或者具有涂层的配制剂的包衣片剂不同的结构。通过将液体倒入预制的粉末模具中而制备锭剂。然后将静止的液体锭剂前体缓慢冷却直至其固化。
在一个优选的形式中,产品的熔体通过作为液滴施加到带上并在运输期间冷却直到固化完成而在冷却输送带装置中制成锭剂。
成形体的另一优选形式是薄片。例如,用剥离辊进行剥离:将熔体以薄层形式施加到冷却的旋转辊上,其中在旋转过程中其完全固化。固体产品通过固定刮板从辊连续分离,从而破碎成小片,即所谓的薄片。本发明还提供了用于制备本发明组合物或本发明成形体的方法,其特征在于以下步骤:
i)在催化剂存在下,用烷基酯b1)或b2)使碳水化合物酯化,
ii)加入酯油c1)或c2),
iii)将粗产物与剩余的糖分离,任选地
iv)使分离出的液相漂白,和任选地
v)制备成形体。
在一个替换方案中,本发明方法可以包括其他步骤。
在另一替换方案中,该方法的特征在于上述步骤,并且不包括其他步骤。
在一个实施方案中,该方法是用于通过在碱金属碳酸盐和碱金属次磷酸盐的催化剂混合物存在下碱催化酯化或酯交换制备平均酯化度为1-4的碳水化合物偏酯的无溶剂方法,其中
i-1)使至少一种碱金属碳酸盐与至少一种烷基酯b1)和/或b2)混合以形成催化活性体系,和
i-2)在恒定搅拌下,将优选具有5-12个碳原子的碳水化合物、任选地作为乳化剂的碳水化合物偏酯和碱金属次磷酸盐加入由i-1)得到的混合物,从而得到分散体,并且将相应的烷基醇在至多100℃的温度下在至多50毫巴的压力下在恒定搅拌下从所得混合物中除去,和
i-3)在至多50毫巴的压力和至多125℃的温度下在恒定搅拌下继续酯化或酯交换,直至烷基酯b1)和/或b2)的含量降至基于总组合物至少8重量%,其中步骤i-1)至i-3)任选地在惰性气体气氛下进行。
在本发明方法中,碱金属碳酸盐和碱金属次磷酸盐的催化剂组合以良好的产率和相对较短的反应时间提供具有相对低灰分含量的改进颜色的产品。此外,减少副产物如皂的形成。氮气优选用作惰性气体。惰性气体的使用使产品颜色更浅。
反应在无溶剂存在下进行,这从经济方面来看和就在化妆品领域中的应用而言是显著有利的。该方法的另一出乎意料的优点是尽管碱金属催化剂还原,但在相对短的反应时间内以改进的颜色品质实现有效反应。在一个替换方案中,本发明方法类似于WO 2006/050832A2中描述的方法进行,其公开内容通过引用并入本文。
根据本发明,使用碱金属碳酸盐和碱金属次磷酸盐的组合作为催化剂。优选使用碳酸钠和/或碳酸钾以及次磷酸钠和/或次磷酸钾。根据本发明有利的是每摩尔糖使用0.06-0.6摩尔碱金属碳酸盐和0.01-0.1摩尔碱金属次磷酸盐。根据本发明,已证明每摩尔糖0.07-0.3摩尔碳酸钾和0.01-0.05摩尔次磷酸钠,特别是每摩尔糖0.08-0.2摩尔碳酸钾和0.01-0.03摩尔次磷酸钠,非常特别优选每摩尔糖0.1-0.15摩尔碳酸钾和0.012-0.02摩尔次磷酸钠的用量是特别有利的。
在本发明的上下文中,已经证明特别有利的是使用如下碳水化合物偏酯作为乳化剂,其碳水化合物单元与目标产物的那些相同。根据本发明,特别有利的是使用如下碳水化合物偏酯,其中碳水化合物单元和酯基均与目标产物的那些相一致,也就是说任选地仅酯化度不同。使用平均酯化度为2-6,特别是3-4的蔗糖偏酯是特别优选的。合适的糖酯是例如Sisterna(R)SP 01、Sisterna(R)SP 30和Sisterna(R)SP 50。根据本发明优选的乳化剂是具有低比例单酯,优选单酯比例小于30重量%,特别是单酯比例小于1重量%的糖酯。根据本发明,使用具有相应低比例单酯的C16/C18-脂肪酸的蔗糖偏酯是特别优选的,因为这些减少反应时间并有助于快速反应。碳水化合物偏酯可作为粉末,以液体形式,以及以丸剂形式使用。因此证明有利的是例如使用具有也用作反应物的那些脂肪酸甲酯的蔗糖偏酯丸剂。
可能的额外的助乳化剂是例如选自如下组中的至少一种的非离子表面活性剂:
(1)2-30摩尔氧化乙烯和/或0-5摩尔氧化丙烯在具有8-22个C原子的支链脂肪醇上,在具有12-22个C原子的脂肪酸上和在烷基中具有8-15个C原子的烷基酚和烷基中具有8-22个C原子的烷基胺上的加成产物;
(2)1-30摩尔氧化乙烯在甘油上的加成产物的C2-C18脂肪酸单酯和二酯;
(3)具有6-22个碳原子的饱和和不饱和脂肪酸的甘油单酯和二酯及脱水山梨糖醇单酯和二酯及其氧化乙烯加成产物;
(4)烷基中具有8-22个碳原子的烷基单糖苷和低聚糖苷及其乙氧基化类似物;
(5)15-60摩尔氧化乙烯在蓖麻油和/或氢化蓖麻油上的加成产物;
(6)多元醇,特别是聚甘油酯,例如聚甘油聚蓖麻醇酸酯或聚甘油聚-12-羟基硬脂酸酯。来自这些物质类别中的几种的化合物的混合物同样适合;
(7)1-15摩尔氧化乙烯在蓖麻油和/或氢化蓖麻油上的加成产物;
(8)基于直链、支化、不饱和或饱和的C6/C22脂肪酸、蓖麻油酸和12-羟基硬脂酸以及甘油、聚甘油、季戊四醇、二季戊四醇、糖醇(例如山梨糖醇)、烷基葡糖苷(例如甲基葡糖苷、丁基葡糖苷、月桂基葡糖苷)和聚葡糖苷(如纤维素)的偏酯;
(9)磷酸单-、二-和三烷基酯以及磷酸单-、二-和/或三-PEG-烷基酯及其盐;
(10)羊毛蜡醇;
(11)聚硅氧烷/聚烷基聚醚共聚物和相应的衍生物;
(12)根据的季戊四醇、脂肪酸、柠檬酸和脂肪醇的混合酯和/或具有6-22个碳原子的脂肪酸、甲基葡萄糖和多元醇,优选甘油的混合酯,和
(13)聚亚烷基二醇。
用作乳化剂的碳水化合物偏酯与用作离析物的碳水化合物的摩尔比优选为0.03-0.25,优选0.04-0.2,特别优选0.09-0.12。
根据本发明优选的方法是其中碱金属碳酸盐:烷基酯b1)和/或b2):用作离析物的碳水化合物:作为乳化剂的碳水化合物偏酯:碱金属次磷酸盐的摩尔比在(0.06-0.6):(0.6-2.0):1:(0.04-0.2):(0.01-0.1)之间变化的方法。
反应通过其中包含催化剂体系、碳水化合物和碳水化合物酯以及任选地其他乳化剂的乳液/分散体在剧烈搅拌下制备的程序进行。在中至高粘度混合物的情况下,机械搅拌以工业规模使用叶轮式搅拌器与挡板组合的搅拌器系统以50-400转/分钟,优选100-300转/分钟的旋转速度进行。
优选地,步骤i-2)和步骤i-3)中的压力为至多25毫巴,非常特别优选至多15毫巴,特别是至多10毫巴。这些压力条件确保尽可能有效地从反应平衡中除去水。特别地,步骤i-2)中的“预干燥”旨在除去由原料导致的残留水。步骤i-2)优选在70-85℃,特别是75-80℃的温度和1-25毫巴,优选1-15毫巴的压力下进行。实际的酯化反应,步骤i-3)优选在100-125℃,特别是110-120℃,特别优选115-120℃的温度和1-25毫巴,优选1-15毫巴,特别优选1-10毫巴的压力下进行。继续酯化反应i-3)直到烷基酯b2)和/或b1)的含量降至基于总组合物至少8重量%,优选基于总组合物至少5重量%。反应时间通常在5-15小时的范围内,并且可以通过有效搅拌而显著减少。
以这种方式制备的产物通常具有上述的碳水化合物偏酯分布。粗产物中未反应的糖的比例通常为至多15重量%,优选至多10重量%。
在另一实施方案中,使氮气惰性气体的温和料流通过反应混合物,但不偏离上述压力条件。该程序得到颜色较浅的产品。
在根据本发明优选的方法形式中,将热反应产物溶解在作为软化剂的酯油c1)和/或c2)中。
在分离出未反应的碳水化合物后,将混合物用过氧化氢漂白,优选在氮气气氛下,任选用酸处理以形成6-8的pH,然后任选地滤过过滤助剂。
在一个替换方案中,在后处理期间不使用其他软化剂。
在另一替换方案中,在制备期间或在后处理期间均不使用其他软化剂。
在一个方案中,在后处理期间使用其他软化剂。
本发明上下文中,其他软化剂在此应理解为意指在40℃,优选在60℃和常压下变为液体的油状物质。
软化剂必须能够在室温下或任选地热的影响下使通过根据本发明方法制备的碳水化合物偏酯溶解。在室温为固体、糊状或蜡状以及处于熔融状态下对碳水化合物偏酯具有良好溶解力的油状物质也适合作为软化剂,根据本发明,适合的是例如烃、酯油、多元醇、二烷基醚、碳酸二烷基酯,例如Cetiol(R)S、Sylko(R)365NF、Panalane(R)L 14E、Cetiol(R)NPC、Cetiol(R)SN、Cetiol(R)PGL1Edenor(R)V、Cetiol(R)OE、Cetiol(R)CC。根据本发明优选合适的是烃,尤其是在20℃和常压下为液体的聚异丁烯,特别是氢化聚异丁烯(其可以名称Panalane L14E(制造商:Amoco;INCI名称:氢化聚异丁烯)市购)。除了低粘度之外,后者的特征在于对根据本发明制备的蔗糖酯非常好的溶解性能和就化妆品终端配制剂而言的感官优点。液体、糊状或蜡状的C6-C22脂肪酸和C1-C3醇的酯油,例如Edenor(R)ME 16V特别适合作为根据本发明制备的碳水化合物偏酯的溶剂。
在一个实施方案中,在碳水化合物偏酯的合成之后,催化剂的失活既不在其他工艺步骤中也不在后处理期间进行。
未反应的碳水化合物可以例如通过倾析、离心和/或通过过滤分离出来。在本发明的一个实施方案中,未反应的碳水化合物通过倾析和/或离心分离。
在另一实施方案中,采用特别是与筛式离心机不同的倾析离心机(优选以连续过程)。
根据本发明优选通过倾析进行分离。
对于本发明方法关键的是步骤i)的产物具有与来自步骤iii)、iv)或v)的产物之一相同的碳水化合物偏酯分布。
中间体,即来自步骤i)的产物是粘稠的,浑浊的和深褐色的。
在分离之后,通常获得其中剩余糖含量基于产物混合物的总组成小于10重量%,特别是小于5重量%的组合物。
然后进行优选在氮气气氛下进行的使用过氧化氢的漂白步骤。然后将反应产物在真空中再次干燥以除去剩余量的水。
产物混合物的pH应在6-8之间,并且任选地通过加入酸而调节。为此可使用常规的无机酸或果酸。根据本发明,加入柠檬酸或乳酸是特别合适的。乳酸是特别合适的,因为以这种方式中和的产物导致更稳定的化妆品终端配制剂。
在与EP 1 811 951B1的方法相同的制备时间内用本发明方法制备碳水化合物偏酯。粗产物的碳水化合物偏酯分布与终产物相同。
本发明还提供了在如上所述的方法中制备的组合物,所述方法的优选特征在于以下步骤:
i)在催化剂存在下用烷基酯b)使碳水化合物酯化,
ii)加入酯油c),
iii)将粗产物与剩余糖分离,任选地
iv)使分离出的液相漂白,和任选地
v)制备成形体。
本发明还提供包含本发明组合物或成形体或在根据本发明的方法中制备的产品的化妆品和/或药物产品或食品。
在本发明的上下文中的化妆品和/或药物产品是:洗发水、美发乳、泡沫浴液、淋浴液、霜、凝胶、乳剂、含酒精和含水/酒精的溶液、乳液、蜡/脂肪组合物、棒制剂、粉末或软膏。
这些组合物还可以包含作为其他辅助物质和添加剂的温和表面活性剂、油性物质、乳化剂、珠光蜡、赋予稠度的试剂、增稠剂、富油剂、稳定剂、聚合物、聚硅氧烷化合物、脂肪、蜡、卵磷脂、磷脂、生物活性化合物、UV光保护因子、抗氧化剂、除臭剂、止汗剂、去头屑剂、成膜剂、溶胀剂、驱虫剂、自晒黑剂、酪氨酸抑制剂(脱色剂)、水溶助长性物质、增溶剂、防腐剂、香料油、染料、颜料、具有赋予颜色性质的物质和/或颜料、杀菌剂或抑菌活性化合物、吸汗物质等。
表面活性剂:组合物可以包含阴离子、非离子、阳离子和/或两性或两性离子表面活性剂作为表面活性物质,其在组合物中的比例通常为约1-70重量%,优选5-50重量%,特别是10-30重量%。阴离子表面活性剂的典型实例是皂、烷基苯磺酸盐、烷烃磺酸盐、烯烃磺酸盐、烷基醚-磺酸盐、甘油醚-磺酸盐、α-甲基酯-磺酸盐、磺基-脂肪酸、烷基硫酸盐、脂肪醇醚-硫酸盐、甘油醚-硫酸盐、脂肪酸醚-硫酸盐、羟基-混合醚-硫酸盐、甘油单酯(醚)硫酸盐、脂肪酸酰胺(醚)硫酸盐、磺基琥珀酸单烷基酯和二烷基酯、磺基琥珀酰胺酸单烷基酯和二烷基酯、磺基甘油三酯、酰胺皂、醚-羧酸和其盐、脂肪酸羟乙磺酸酯、脂肪酸肌氨酸盐、脂肪酸牛磺酸盐、N-酰基氨基酸如酰基乳酸盐、酰基酒石酸盐、酰基谷氨酸盐和酰基天冬氨酸盐、烷基低聚葡糖苷-硫酸盐、蛋白质-脂肪酸缩合物(特别是基于小麦的植物产物)和烷基(醚)磷酸盐。如果阴离子表面活性剂包含聚乙二醇醚链,则它们可以具有常规但优选的窄分布同系物。非离子表面活性剂的典型实例是脂肪醇聚乙二醇醚、烷基酚聚乙二醇醚、脂肪酸聚乙二醇酯、脂肪酸酰胺聚乙二醇醚、脂肪胺聚乙二醇醚、烷氧基化甘油三酯、混合醚或混合甲醛、任选部分氧化的烷基(链烯基)低聚糖苷和葡糖醛酸衍生物、脂肪酸N-烷基葡糖酰胺、蛋白质水解物(特别是基于小麦的植物产物)、多元醇脂肪酸酯、糖酯、脱水山梨糖醇酯、聚山梨糖醇酯和氧化胺。如果非离子表面活性剂包含聚乙二醇醚链,则它们可以具有常规但优选的窄分布同系物。阳离子表面活性剂的典型实例是季铵化合物,例如二甲基二硬脂基氯化铵和酯季铵盐,特别是季铵化脂肪酸三烷醇胺酯盐。两性或两性离子表面活性剂的典型实例是烷基甜菜碱、烷基酰氨基甜菜碱、氨基丙酸酯、氨基甘氨酸盐、咪唑啉甜菜碱和磺基甜菜碱。所提及的表面活性剂是仅已知的化合物。就这些物质的结构和制备而言,可以参考相关的概述著作,例如J.Falbe(编辑),“Surfactants in Consumer Products”,Springer Verlag,Berlin,1987,第54-124页或J.Falbe(编辑),“Katalysatoren,Tensideund”,Thieme Verlag,Stuttgart,1978,第123-217页。特别合适的温和表面活性剂,即特别是皮肤耐受的表面活性剂的典型实例是脂肪醇聚乙二醇醚-硫酸盐、甘油单酯硫酸盐、单和/或二烷基磺基琥珀酸盐、脂肪酸羟乙磺酸盐、脂肪酸肌氨酸盐、脂肪酸牛磺酸盐、脂肪酸谷氨酸盐、烯烃-磺酸盐、醚-羧酸、烷基低聚葡糖苷、脂肪酸葡糖酰胺、烷基酰氨基甜菜碱、两性缩醛和/或蛋白质-脂肪酸缩合物,后者优选基于小麦蛋白质或其盐。
油性物质:身体护理组合物如霜、洗剂和乳剂,通常包含许多其他进一步优化感官性能的油性物质和软化剂。取决于配制剂的性质,油性物质可以以1-90重量%的总量,特别是1-50重量%,优选5-25重量%,特别是5-15重量%的总量包含于其中。
作为油性物质的物质是例如基于具有6-18,优选8-10个碳原子的脂肪醇的格尔伯特醇,直链C6-C22脂肪酸与直链或支化C6-C22脂肪醇的酯和支化C6-C13羧酸与直链或支化C6-C22脂肪醇的酯,例如肉豆蔻酸肉豆蔻酯、棕榈酸肉豆蔻酯、硬脂酸肉豆蔻酯、异硬脂酸肉豆蔻酯、油酸肉豆蔻酯、山萮酸肉豆蔻酯、芥酸肉豆蔻酯、肉豆蔻酸鲸蜡酯、棕榈酸鲸蜡酯、硬脂酸鲸蜡酯、异硬脂酸鲸蜡酯、油酸鲸蜡酯、山萮酸鲸蜡酯、芥酸鲸蜡酯、肉豆蔻酸硬脂醇酯、棕榈酸硬脂醇酯、硬脂酸硬脂醇酯、异硬脂酸硬脂醇酯、油酸硬脂醇酯、山萮酸硬脂醇酯、芥酸硬脂醇酯、肉豆蔻酸异硬脂醇酯、棕榈酸异硬脂醇酯、硬脂酸异硬脂醇酯、异硬脂酸异硬脂醇酯、油酸异硬脂醇酯、山萮酸异硬脂醇酯、油酸异硬脂醇酯、肉豆蔻酸油醇酯、棕榈酸油醇酯、硬脂酸油醇酯、异硬脂酸油醇酯、油酸油醇酯、山萮酸油醇酯、芥酸油醇酯、肉豆蔻酸山萮醇酯、棕榈酸山萮醇酯、硬脂酸山萮醇酯、异硬脂酸山萮醇酯、油酸山萮醇酯、山萮酸山萮醇酯、芥酸山萮醇酯、肉豆蔻酸瓢儿菜醇酯、棕榈酸瓢儿菜醇酯、硬脂酸瓢儿菜醇酯、异硬脂酸瓢儿菜醇酯、油酸瓢儿菜醇酯、山萮酸瓢儿菜醇酯、芥酸瓢儿菜醇酯。此外,直链C6-C22脂肪酸与支化醇,特别是2-乙基己醇的酯,C18-C38烷基羟基羧酸与直链或支化C6-C22脂肪醇的酯(参见DE 19756377a2),特别是苹果酸二辛酯,直链和/或支化脂肪酸与多元醇(例如丙二醇、二聚体二醇或三聚体三醇)和/或格尔伯特醇的酯,基于C6-C10脂肪酸的甘油三酯,基于C6-C18脂肪酸的液体甘油单/二/三酯混合物,C6-C22脂肪醇和/或格尔伯特醇与芳族羧酸,特别是苯甲酸的酯,C2-C12二羧酸与具有1-22个碳原子的直链或支化醇或具有2-10个碳原子和2-6个羟基的多元醇的酯,植物油,支化伯醇,取代的环己烷,直链和支化C6-C22脂肪醇碳酸酯,例如碳酸二辛酯(OE),基于具有6-18个C原子,优选8-10个C原子的脂肪醇的格尔伯特碳酸酯,苯甲酸与直链和/或支化C6-C22醇的酯(例如FinsolvΣTN),每个烷基具有6-22个碳原子的直链或支化的对称或不对称的二烷基醚,例如二辛基醚(OE),环氧化脂肪酸酯与多元醇的开环产物,硅油(环聚甲基硅氧烷,硅聚甲基硅氧烷类等)和/或脂族或环烷烃,如角鲨烷、角鲨烯或二烷基环己烷是合适的。
乳化剂:可能的乳化剂是例如选自如下组中的至少一种的非离子表面活性剂:
聚甘油(平均自缩合度为2-8)、聚乙二醇(分子量400-5,000)、三羟甲基丙烷、季戊四醇、糖醇如山梨糖醇、烷基葡糖苷(例如甲基葡糖苷、丁基葡糖苷、月桂基葡糖苷)和聚葡糖苷(例如纤维素)与具有12-22个碳原子的饱和和/或不饱和的直链或支化脂肪酸和/或具有3-18个碳原子的羟基羧酸的偏酯,及其与1-30摩尔氧化乙烯的加合物;
聚甘油酯:合适的聚甘油酯的典型实例是聚甘油-2二聚羟基硬脂酸酯(DehymulsΣPGPH)、聚甘油-3二异硬脂酸酯(LameformΣTGI)、聚甘油-4异硬脂酸酯(IsolanΣGI34)、聚甘油-3油酸酯、二异硬脂酰基聚甘油-3二异硬脂酸酯(IsolanΣPDI)、聚甘油-3甲基葡萄糖二硬脂酸酯(TegoCareΣ450)、聚甘油-3蜂蜡(Cera BellinaΣ)、聚甘油-4癸酸酯(Polyglycerol Caprate T2010/90)、聚甘油-3鲸蜡基醚(ChimexaneΣNL)、聚甘油-3二硬脂酸酯CremophorΣGS 32)和聚甘油聚蓖麻醇酸酯(AdmulΣWOL 1403)、聚甘油二聚酸酯二异硬脂酸酯及其混合物。其他合适的多元醇酯的实例是三羟甲基丙烷或季戊四醇与月桂酸、椰油脂肪酸、牛油脂肪酸、棕榈酸、硬脂酸、油酸、山萮酸等的单-、二-和三酯(任选地与1-30摩尔氧化乙烯反应)。
阴离子乳化剂:典型的阴离子乳化剂是具有12-22个碳原子的脂族脂肪酸,例如棕榈酸、硬脂酸或山萮酸,以及具有12-22个碳原子的二羧酸,例如壬二酸或癸二酸。
两性和阳离子乳化剂:此外,两性离子表面活性剂可用作乳化剂。在分子中携带至少一个季铵基以及至少一个羧酸根基和一个磺酸根基的那些表面活性化合物称为两性离子表面活性剂。特别合适的两性离子表面活性剂是所谓的甜菜碱,例如N-烷基-N,N-二甲基铵甘氨酸盐,例如椰油烷基二甲基铵甘氨酸盐,N-酰基氨基丙基-N,N-二甲基铵甘氨酸盐,例如椰油酰基氨基丙基二甲基铵甘氨酸盐和2-烷基-3-羧甲基-3-羟乙基咪唑啉(其在烷基或酰基中在每种情况下具有8-18个C原子)和椰油酰基氨基乙基羟乙基羧甲基甘氨酸盐。已知CTFA名称为椰油酰胺丙基甜菜碱的脂肪酸酰胺衍生物是特别优选的。两性表面活性剂是同样适合的乳化剂。两性表面活性剂应理解为意指那些在分子中除了C8/18烷基或酰基之外还包含至少一个游离氨基和至少一个COOH或-SO3H基团并且能够形成内盐的表面活性化合物。合适的两性表面活性剂的实例是N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸(其在每种情况下在烷基中具有约8-18个C原子)。特别优选的两性表面活性剂是N-椰油烷基氨基丙酸盐、椰油酰基氨基乙基氨基丙酸盐和C12/18酰基肌氨酸。最后,阳离子表面活性剂也是可能的乳化剂,其中特别优选酯-季铵盐类,优选甲基季铵化的二脂肪酸三乙醇胺酯盐的那些。
脂肪和蜡:将脂肪和蜡添加到身体护理产品中作为护理物质,并且使得化妆品的稠度提高。脂肪的典型实例是甘油酯,即固体植物或动物产物,其基本上由混合的高级脂肪酸甘油酯组成。对此还可能的是脂肪酸偏甘油酯,即工业级的具有12-18个碳原子的脂肪酸甘油单酯和/或二酯,例如甘油单/二月桂酸酯、棕榈酸酯或硬脂酸酯。脂肪的典型实例是甘油酯,即固体或液体植物或动物产物,其基本上由混合的高级脂肪酸甘油酯组成,可能的蜡尤其是天然蜡,例如小烛树蜡、巴西棕榈蜡、野漆树蜡、西班牙草蜡、软木蜡、瓜拉蜡(guaruma wax)、稻胚芽油蜡、甘蔗蜡、小冠巴西棕蜡、褐煤蜡、蜂蜡、紫胶蜡、鲸蜡、羊毛脂(羊毛蜡)、尾臀脂肪(uropygium fat)、纯地蜡、地蜡、凡士林、石蜡、微晶蜡;化学改性蜡(硬蜡),例如褐煤酯蜡、Sasol蜡、氢化霍霍巴蜡和合成蜡,例如聚亚烷基蜡和聚乙二醇蜡。除了脂肪之外,类脂物质如卵磷脂和磷脂也可以作为添加剂。名称卵磷脂本领域技术人员应理解为是指那些由脂肪酸、甘油、磷酸和胆碱通过酯化而形成的甘油磷脂。卵磷脂因此也是技术领域中的磷脂酰胆碱(PC)。可以提及的天然卵磷脂的实例是脑磷脂,其也称为磷脂酸,并且是1,2-二酰基-sn-甘油-3-磷酸的衍生物。与其不同地,磷脂通常应理解为表示磷酸与甘油的单-和优选二酯(磷酸甘油酯),其通常归类为脂肪。此外,鞘氨醇和鞘脂也是可能的。
珠光蜡:可能的珠光蜡是例如:亚烷基二醇酯,特别是二硬脂酸乙二醇酯;脂肪酸链烷醇酰胺,特别是椰油脂肪酸二乙醇酰胺;偏甘油酯,特别是硬脂酸甘油单酯;多元的、任选羟基取代的羧酸与具有6-22个碳原子的脂肪醇的酯,特别是酒石酸的长链酯;脂肪物质,例如脂肪醇、脂肪酮、脂肪醛、脂肪醚和脂肪碳酸酯,其总共包含至少24个碳原子,特别是月桂酮和二硬脂基醚;脂肪酸,例如硬脂酸、羟基硬脂酸或山萮酸,具有12-22个碳原子的烯烃环氧化物与具有12-22个碳原子的脂肪醇和/或具有2-15个碳原子和2-10个羟基的多元醇的开环产物,及其混合物。
赋予稠度的试剂和增稠剂:可能的赋予稠度的试剂主要是具有12-22个碳原子,优选16-18个碳原子的脂肪醇或羟基脂肪醇,此外还有偏甘油酯、脂肪酸或羟基脂肪酸。这些物质与烷基低聚葡糖苷和/或相同链长的脂肪酸N-甲基葡糖酰胺和/或聚甘油聚-12-羟基硬脂酸酯的组合是优选的。合适的增稠剂是例如Aerosil型(亲水性二氧化硅),多糖,特别是黄原胶、瓜尔胶(Guar-Guar)、琼脂、海藻酸盐和纤维乙酸钠、羧甲基纤维素以及羟乙基-和羟丙基纤维素,以及脂肪酸的较高分子量聚乙二醇单-和二酯,聚丙烯酸酯(例如来自Goodrich的CarbopolsΣ和Pemulen型;来自Sigma的SynthalensΣ;来自Kelco的Keltrol型;来自Seppic的Sepigel型;来自Allied Colloids的Salcare型),聚丙烯酰胺,聚合物,聚乙烯醇和聚乙烯基吡咯烷酮。也已证明膨润土是特别有效的,例如Gel VS-5PC(Rheox),它是环戊硅氧烷、二硬脂基二甲铵水辉石(Disteardimonium Hectorite)和碳酸亚丙酯的混合物。此外可能的是表面活性剂,例如乙氧基化脂肪酸甘油酯、脂肪酸与多元醇如季戊四醇或三羟甲基丙烷的酯、具有窄同系物分布的脂肪醇乙氧基化物或烷基低聚葡糖苷和电解质如氯化钠和氯化铵。
富油剂:可以使用的富油剂是例如羊毛脂和卵磷脂以及聚乙氧基化或酰化羊毛脂和卵磷脂衍生物,多元醇脂肪酸酯,甘油单酯和脂肪酸链烷醇酰胺等物质,后者同时用作泡沫稳定剂。
稳定剂:可以使用的稳定剂是脂肪酸的金属盐,例如硬脂酸或蓖麻酸的镁、铝和/或锌盐。
聚合物:合适的阳离子聚合物是例如阳离子纤维素衍生物,例如季铵化的羟乙基纤维素(可由Amerchol以名称Polymer JR400Σ获得),阳离子淀粉,二烯丙基铵盐和丙烯酰胺的共聚物,季铵化的乙烯基吡咯烷酮/乙烯基咪唑聚合物如LuviquatΣ(BASF),聚二醇和胺的缩合产物,季铵化的胶原多肽如月桂基二甲基铵羟丙基水解胶原(Lamequat□L/Grünau),季铵化的小麦多肽,聚乙烯亚胺,阳离子聚硅氧烷聚合物如氨基封端的聚二甲基硅氧烷,己二酸和二甲基氨基羟丙基二亚乙基三胺的共聚物(CartaretineΣ/Sandoz),丙烯酸与二甲基二烯丙基氯化铵的共聚物(MerquatΣ550/Chemviron),聚氨基聚酰胺(例如如FR2252840A中所述)及其交联的水溶性聚合物,阳离子甲壳质衍生物如季铵化的壳聚糖,任选以微晶形式分布的二卤代烷烃(如二溴丁烷)与双二烷基胺(如双二甲基氨基-1,3-丙烷)的缩合产物,阳离子瓜尔胶如来自Celanese的JaguarΣCBS、JaguarΣC-17、JaguarΣC-16,季铵化的铵盐聚合物如来自Miranol的MirapolΣA-15、MirapolΣAD-1、MirapolΣAZ-1。
可能的阴离子、两性离子、两性和非离子聚合物是例如乙酸乙烯酯/巴豆酸共聚物,乙烯基吡咯烷酮/丙烯酸乙烯酯共聚物,乙酸乙烯酯/马来酸丁酯/丙烯酸异冰片酯共聚物,甲基乙烯基醚/马来酸酐共聚物及其酯,未交联和多元醇交联的聚丙烯酸,丙烯酰氨基丙基三甲基氯化铵/丙烯酸酯共聚物,辛基丙烯酰胺/甲基丙烯酸甲酯/甲基丙烯酸叔丁基氨基乙酯/甲基丙烯酸2-羟丙酯共聚物,聚乙烯基吡咯烷酮,乙烯基吡咯烷酮/乙酸乙烯酯共聚物,乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙酯/乙烯基己内酰胺三元共聚物和任选地衍生化纤维素醚和聚硅氧烷。其他合适的聚合物和增稠剂列于Cosm.Toil.108,95(1993)。
聚硅氧烷化合物:合适的聚硅氧烷化合物是例如二甲基聚硅氧烷,甲基苯基聚硅氧烷,环状聚硅氧烷和氨基、脂肪酸、醇、聚醚、环氧、氟、糖苷和/或烷基改性的聚硅氧烷化合物,其可以在室温下为液体或树脂状。此外合适的是水合硅石聚二甲基硅氧烷,其为具有平均链长200-300个二甲基硅氧烷单元的聚二甲基硅氧烷和氢化硅酸盐的混合物。此外,合适的挥发性聚硅氧烷的详细概述在Todd等,Cosm.Toil.91,27(1976)中找到。
UV光保护过滤剂和抗氧化剂:UV光保护因子应理解为意指例如在室温下为液体或晶体,且其能够吸收紫外线并再次以较长波长的辐射的形式,例如热释放所吸收的能量的有机物质(光保护过滤剂)。UVB过滤剂可以是油溶性的或水溶性的。
要提及的油溶性物质是例如:
N-{(2和4)-[2-氧代冰片-3-亚基)甲基}苄基]丙烯酰胺(Mexoryl SW)2-(2H-苯并三唑-2-基)-4-甲基-6-(2-甲基-3-(1,3,3,3-四甲基-1-(三甲基甲硅烷氧基)二硅氧烷基)丙基)苯酚(Mexoryl XL)
亚苄基丙二酸的酯,优选4-甲氧基亚苄基丙二酸二-2-乙基己酯;三嗪衍生物,例如2,4,6-三苯胺基-(对-羰基-2'-乙基-1'-己氧基)-1,3,5-三嗪和2,4,6-三[对(2-乙基己氧基羰基)苯胺基]-1,3,5-三嗪(Uvinul T 150),如EP 0818450 A1所述或4,4'-[(6-[4-((1,1-二甲基乙基)氨基羰基)苯基氨基]-1,3,5-三嗪-2,4-二基)二亚氨基]双(苯甲酸2-乙基己酯)(UvasorbΣHEB);
可能的水溶性UV过滤剂为:
2,2(-(1,4-亚苯基)双(1H-苯并咪唑-4,6-二磺酸单钠盐)(Neo Heliopan AP)二苯甲酮的磺酸衍生物,优选2-羟基-4-甲氧基二苯甲酮-5-磺酸及其盐;3-亚苄基樟脑的磺酸衍生物,例如4-(2-氧代-3-亚冰片基-甲基)苯磺酸和2-甲基-5-(2-氧代-3-亚冰片基)磺酸及其盐。
可能的典型的UV-A过滤剂特别是苯甲酰基甲烷的衍生物如1-(4'-叔丁基苯基)-3-(4'-甲氧基苯基)丙烷-1,3-二酮、4-叔丁基-4'-甲氧基二苯甲酰基甲烷(ParsolΣ1789)、1-苯基-3-(4'-异丙基苯基)丙烷-1,3-二酮,和烯胺化合物(如DE 19712033 A1(BASF)中所述),和2-[4-(二乙基氨基)-2-羟基苯甲酰基]苯甲酸己基酯(UvinulΣAplus)。
UV-A和UV-B过滤剂当然也可以混合物形式使用。特别有利的组合由苯甲酰基甲烷的衍生物如4-叔丁基-4'-甲氧基二苯甲酰基甲烷(ParsolΣ1789)和2-氰基-3,3-苯基肉桂酸2-乙基己酯(氰双苯丙烯酸辛酯)与肉桂酸酯(优选4-甲氧基肉桂酸2-乙基己酯和/或4-甲氧基肉桂酸丙酯和/或4-甲氧基肉桂酸异戊酯)的组合组成。该类组合有利地与水溶性过滤剂,例如2-苯基苯并咪唑-5-磺酸及其碱金属、碱土金属、铵、烷基铵、链烷醇铵和葡糖铵盐组合。
根据本发明优选的UV光保护过滤剂选自欧洲化妆品法规的附录VII(第24条修订理事会指令,2000年2月29日)。
除了所提及的可溶性物质外,为此还可以使用不溶性光保护颜料,即细分散的金属氧化物或盐。合适的金属氧化物的实例特别是氧化锌和二氧化钛,以及铁、锆、硅、锰、铝和铈的氧化物及其混合物。可以使用的盐是硅酸盐(滑石)、硫酸钡或硬脂酸锌。氧化物和盐以颜料的形式用于皮肤护理和皮肤保护乳液以及用于装饰性化妆品。颗粒的平均直径应小于100nm,优选5-50nm,特别是15-30nm。它们可以具有球形形状,但是也可以使用具有椭圆形状或其他偏离球形的形状的那些颗粒。颜料也可以以表面处理形式存在,即亲水化或疏水化。典型的实例是经涂覆的二氧化钛,例如二氧化钛T 805(Degussa)或T、T-2000、T-Aqua、AVO、T-ECO、T-OLEO和T-S(Merck)。典型的实例是氧化锌,例如氧化锌中性、氧化锌NDM(Symrise)或(BASF)或SUNZnO-AS和SUNZnO-NAS(Sunjun ChemicalCo.Ltd.)。就此而言,可能的疏水涂覆剂主要为聚硅氧烷,且就此而言具体为三烷氧基辛基硅烷或水合硅石聚二甲基硅氧烷。所谓的微米或纳米颜料优选用于防晒组合物中。优选使用微粉化的氧化锌。其他合适的UV光保护过滤剂由P.Finkel在-Journal 122,543(1996)和Parf Kosm.3,11(1999)的概述中已知。
除了两种上述初级光保护物质组之外,还可以使用抗氧剂型的次级光保护剂,其中断当UV辐射穿透到皮肤时引发的光化学反应链。这些的典型实例是氨基酸(例如甘氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物、咪唑(例如尿刊酸)及其衍生物、肽(例如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-胡萝卜素、-胡萝卜素、番茄红素)及其衍生物、绿原酸及其衍生物、脂酮酸及其衍生物(例如二氢脂酮酸)、硫金代葡萄糖、丙基硫氧嘧啶及其他硫醇(例如硫氧还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺及其糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基和月桂基、棕榈酰基、油基、亚油基、胆甾醇基和甘油基的酯)及其盐、硫代二丙酸二月桂基酯、硫代二丙酸二硬脂基酯、硫代二丙酸及其衍生物(酯、醚、肽、类脂、核苷酸、核苷和盐)以及非常低耐受剂量(例如pmol至μmol/kg)的亚砜亚胺化合物(例如丁硫氨酸-亚砜亚胺(Buthioninsulfoximine),高半胱氨酸亚砜亚胺(Homocysteinsulfoximine),丁硫氨酸砜,以及戊-、己-、庚硫氨酸亚砜亚胺),此外还有(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、植酸、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、EGTA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、泛醌和泛醇及其衍生物、维生素C和衍生物(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)、维生素A和衍生物(维生素A棕榈酸酯)以及安息香树脂的苯甲酸松柏醇酯、芸香酸及其衍生物、α-糖基芸香苷、阿魏酸、亚糠基葡糖醇、肌肽、丁基羟基甲苯、丁基羟基苯甲醚、去甲二氢愈创木树脂酸、去甲二氢愈创木酸、三羟基苯丁酮、尿酸及其衍生物、甘露糖及其衍生物、超氧化物歧化酶、锌及其衍生物(例如ZnO、ZnSO4)、硒及其衍生物(蛋氨酸硒)、茋及其衍生物(例如均二苯代乙烯氧化物、反式-均二苯代乙烯氧化物)以及这些根据本发明合适的提及的活性化合物的衍生物(盐、酯、醚、糖、核苷酸、核苷、肽和类脂)。
因此,本发明还提供防晒组合物,其特征在于它们包含选自由3-亚苄基樟脑和3-亚苄基降樟脑及其衍生物、4-氨基苯甲酸衍生物、肉桂酸酯、水杨酸酯、亚苄基丙二酸酯、二苯甲酮衍生物、苯甲酰基甲烷衍生物、三嗪衍生物、丙烷-1,3-二酮、酮三环(5.2.1.0)癸烷衍生物、2-苯基苯并咪唑-5-磺酸及其盐和二苯甲酮和3-亚苄基樟脑的磺酸衍生物组成的组的有机UV光保护过滤剂。
本发明防晒组合物还可以包含无机UV光保护颜料,其选自由二氧化钛、氧化锌、氧化铁、氧化铝、氧化铈、氧化锆、硅酸盐、硫酸钡和硬脂酸锌组成的组。
本发明防晒组合物还可以包含抗氧化剂,其选自由氨基酸及其衍生物、咪唑(例如尿刊酸)及其衍生物、肽及其衍生物、类胡萝卜素、胡萝卜素及其衍生物、绿原酸及其衍生物、脂酮酸及其衍生物、硫金代葡萄糖、丙基硫氧嘧啶和其他硫醇及其盐、硫代二丙酸二月桂基酯、硫代二丙酸二硬脂酸酯、硫代二丙酸及其衍生物、亚砜亚胺化合物、(金属)螯合剂、α-羟基酸、腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、EDTA、EGTA及其衍生物、不饱和脂肪酸及其衍生物、叶酸及其衍生物、泛醌、泛醇及其衍生物、维生素C及其衍生物、生育酚及其衍生物、维生素A及其衍生物、苯甲酸松柏醇酯、芸香酸及其衍生物、α-糖基芸香苷、阿魏酸、亚糠基葡糖醇、肌肽、丁基羟基甲苯、丁基羟基苯甲醚、去甲二氢愈创木树脂酸、去甲二氢愈创木酸、三羟基苯丁酮、尿酸及其衍生物、甘露糖及其衍生物、超氧化物歧化酶、锌及其衍生物、硒及其衍生物和茋及其衍生物组成的组。
生物源活性化合物:生物源活性化合物应理解为是指例如生育酚、生育酚乙酸酯、生育酚棕榈酸酯、抗坏血酸、(脱氧)核糖核酸及其片段产物、β-葡聚糖、视黄醇、红没药醇、尿囊素、植烷三醇、泛醇、AHA酸、氨基酸、神经酰胺、拟神经酰胺、精油、植物提取物(例如李属植物提取物,Bambara坚果提取物)以及维生素复合物。
除臭剂和抑菌剂:化妆品除臭剂中和、掩蔽或消除体味。体味由皮肤细菌对顶泌汗液的作用而形成,形成令人不愉悦的气味的降解产物。因此,除臭剂包含作为抑菌剂、酶抑制剂、气味吸收剂或气味掩蔽剂起作用的活性化合物。
抑菌剂:合适的抑菌剂原则上是所有对革兰氏阳性细菌有活性的物质,例如,4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)脲、2,4,4'-三氯-2'-羟基二苯基醚(三氯生)、4-氯-3,5-二甲基苯酚、2,2'-亚甲基双(6-溴-4-氯苯酚)、3-甲基-4-(1-甲基乙基)苯酚、2-苄基-4-氯苯酚、3-(4-氯苯氧基)-1,2-丙二醇、3-碘-2-丙炔基丁基氨基甲酸酯、氯己定、3,4,4'-三氯碳酰苯胺(TTC)、抗菌气味物质、百里香酚、百里香油、丁香酚、丁香油、薄荷醇、薄荷油、合金欢醇、苯氧乙醇、甘油单癸酸酯、甘油单辛酸酯、甘油单月桂酸酯(GML)、双甘油单癸酸酯(DMC)、水杨酸N-烷基酰胺如水杨酸正辛基酰胺或水杨酸正癸基酰胺。
酶抑制剂:当腋窝区域出现汗液时,细菌形成胞外酶(酯酶,优选蛋白酶和/或脂肪酶),其分离出汗液中包含的酯,从而释放气味物质。合适的酶抑制剂是例如酯酶抑制剂。这些优选为柠檬酸三烷基酯,例如柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯,特别是柠檬酸三乙酯(HydagenΣCAT)。这些物质抑制酶活性,从而减少气味形成。作为酯酶抑制剂可能的其他物质是甾醇硫酸酯或甾醇磷酸酯,例如羊毛甾醇、胆甾醇、菜油甾醇、豆甾醇以及谷甾醇硫酸酯或磷酸酯;二羧酸及其酯,例如戊二酸、戊二酸单乙酯、戊二酸二乙酯、己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸和丙二酸二乙酯,羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙酯以及甘氨酸锌。
气味吸收剂:合适的气味吸收剂是能够吸收并基本保持气味形成化合物的物质。它们降低了单独组分的分压,并且以这种方式也降低了它们扩散的速度。就此而言重要的是香料必须保持不受影响。气味吸收剂对细菌没有活性。它们例如包含蓖麻油酸的复合锌盐或基本中性气味的特定芳香剂作为主要组分,其为本领域技术人员已知的“固定剂”,例如岩蔷薇提取物或苏合香或一些松香酸衍生物。作为气味掩蔽剂起作用的气味物质或香料油是除了作为气味掩蔽剂起作用之外,还赋予除臭剂其特别香味的那些。可提及的香料油是例如天然和合成气味物质的混合物。天然气味物质是花、茎和叶、果实、果皮、根、木材、香草和禾本草、针和枝以及树脂和香脂的提取物。此外,动物原料是可能的,例如麝猫香和海狸香。典型的合成气味化合物是酯类、醚类、醛类、酮类、醇类和烃类的产物。酯类的气味化合物是例如乙酸苄酯、乙酸对叔丁基环己酯、乙酸芳樟酯、乙酸苯乙酯、苯甲酸芳樟酯、甲酸苄酯、环己基丙酸烯丙基酯、丙酸苏合香酯和水杨酸苄酯。醚包括例如苄基乙基醚,醛包括例如具有8-18个碳原子的直链链烷醛、柠檬醛、香茅醛、香茅酰氧基乙醛、仙客来醛、羟基香茅醛、铃兰醛和波洁红醛(Bourgeonal),酮包括例如紫罗兰酮和甲基柏木酮,醇包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯乙醇和萜品醇,烃主要包括萜和香脂。然而,优选使用各种气味物质的混合物,这些混合物一起产生令人愉悦的香调。通常用作芳香组分的相对低挥发性的精油也适合作为香料油,例如鼠尾草油、春黄菊油、丁子香油、蜂花油、薄荷油、肉桂叶油、椴树花油、刺柏油、岩兰油、乳香油、古蓬油、岩蔷薇油和杂薰衣草油。优选以其本身或混合物形式使用香柠檬油、二氢月桂烯醇、铃兰醛、新铃兰醛(lyral)、香茅醇、苯乙醇、α-己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、乙氧基甲氧基环十一烷(boisambrene forte)、龙涎呋喃(ambroxan)、吲哚、二氢茉莉酮酸甲酯(hedione)、Sandelice、柠檬油、红橘油、橙油、戊基甘醇酸烯丙酯、女贞醛(cyclovertal)、杂薰衣草油、香紫苏油(muskateller salbeiol)、β-突厥酮、波旁香叶油(geraniumolbourbon)、水杨酸环己酯、vertofix coeur、龙涎酮(iso-E-Super)、Fixolide NP、合成橡苔(evernyl)、γ-甲基紫罗兰酮(iraldein gamma)、苯乙酸、乙酸香叶酯、乙酸苄基酯、玫瑰醚、romilat、irotyl和floramat。
止汗剂:止汗剂通过影响外分泌腺的活性而减少汗液形成,从而抑制腋下湿润和体臭。止汗剂的水性或无水配制剂通常包含以下成分:收敛剂活性化合物、油性组分、非离子乳化剂、助乳化剂、赋予稠度的试剂、辅助物质如增稠剂或络合剂和/或非水溶剂如乙醇、丙二醇和/或甘油。
合适的收敛止汗活性化合物主要是铝、锆或锌的盐。具有抗水解作用的该类合适的活性化合物是例如氯化铝、氯化羟铝、二氯化羟铝、倍半氯化羟铝及其配合物(例如与1,2-丙二醇的配合物)、尿囊素羟铝、酒石酸氯化铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆及其配合物(例如与氨基酸如甘氨酸的配合物)。此外,止汗剂可以包含相对少量的常规油溶性和水溶性辅助剂。这种油溶性辅助剂可以是例如:抗炎、护肤或令人愉悦的气味的精油,合成的护肤活性化合物,和/或油溶性香料油。
常规的水溶性添加剂是例如防腐剂、水溶性芳香剂、pH调节剂如黄油混合物、水溶性增稠剂如水溶性天然或者合成聚合物(例如黄原胶、羟乙基纤维素、聚乙烯基吡咯烷酮或高分子量聚氧化乙烯)。
成膜剂:常见成膜剂是例如壳聚糖、微晶壳聚糖、季铵化壳聚糖、聚乙烯基吡咯烷酮、乙烯基吡咯烷酮/乙酸乙烯酯共聚物、丙烯酸系聚合物、季铵纤维素衍生物、骨胶原、透明质酸及其盐和类似化合物。
去头皮屑活性化合物:可能的去头皮屑活性化合物是吡罗克酮乙醇胺盐(1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2-(1H)-吡啶酮单乙醇胺盐)、(氯咪巴唑(climbazole))、酮康唑Σ、4-乙酰基-1-Σ-4-[2-(2,4-二氯苯基)-r-2-(1H-咪唑-1-基甲基)-1,3-二氧戊环-c-4-基甲氧基苯基]哌嗪、酮康唑、新康唑、二硫化硒、胶态硫、硫聚乙二醇脱水山梨醇单油酸酯、硫蓖麻醇聚乙氧基化物、硫-焦油馏份、水杨酸(及与六氯酚的组合)、十一碳烯酸单乙醇酰胺磺基琥珀酸钠盐、LameponΣUD(蛋白质-十一碳烯酸缩合物)、吡啶硫酮锌、吡啶硫酮铝和吡啶硫酮镁/双吡啶硫酮-硫酸镁。
溶胀剂:蒙脱石、粘土矿物、Pemulen和烷基改性Carbopol型(Goodrich)可用作水相溶胀剂。其他合适的聚合物和溶胀剂可以在R.Lochhead的Cosm.Toil.108,95(1993)的概述中找到。
驱虫剂:可能的驱虫剂是例如N,N-二乙基-间甲苯甲酰胺、1,2-戊二醇或3Σ(N-正丁基-N-乙酰基氨基)丙酸乙酯(其由Merck KGaA以名称Insect RepellentΣ3535销售)和丁基乙酰氨基丙酸酯。
自晒黑剂和脱色剂:二羟基丙酮适合作为自晒黑剂。防止形成黑色素并用于脱色组合物的可能的酪氨酸抑制剂是例如熊果苷、阿魏酸、曲酸、香豆酸和抗坏血酸(维生素C)。
水溶助长性物质:为了改进流动性,还可以使用水溶助长性物质,例如乙醇、异丙醇或多元醇。在此可能的多元醇优选具有2-15个碳原子和至少两个羟基。多元醇还可以包含其他官能团,特别是氨基,或者可以用氮改性。典型的实例是
香料油和芳香化合物:可以提及的香料油是天然和合成的气味物质的混合物。天然的气味物质是来自花(百合、熏衣草、玫瑰、茉莉、苦橙花、依兰),茎和叶(天竺葵、广藿香、苦橙叶),果实(茴香子、芫荽、芡蒿子(caraway)、刺柏),果皮(香柠檬、柠檬、柑橘),根(肉豆蔻、当归、芹菜、小豆蔻、木香、鸢尾、菖蒲),木(松木、檀香木、愈创木、柏木、蔷薇木),草本植物和禾本植物(龙嵩、香茅、鼠尾草、百里香),针叶和枝桠(云杉、枞树、松树、山松(dwarfpine)),树脂和香脂(古篷香脂、榄香脂、安息香、没药、乳香、防风根)的提取物。此外,动物原料是可能的,例如麝猫香和海狸香。典型的合成气味化合物是酯类、醚类、醛类、酮类、醇类和烃类的产物。酯类的气味化合物是例如乙酸苄酯、异丁酸苯氧基乙酯、乙酸对叔丁基环己酯、乙酸芳樟酯、乙酸二甲基苄基甲酯、乙酸苯乙酯、苯甲酸芳樟酯、甲酸苄酯、甲基苯基甘氨酸乙酯、环己基丙酸烯丙基酯、丙酸苏合香酯和水杨酸苄酯。醚包括例如苄基乙基醚,醛包括例如具有8-18个碳原子的直链链烷醛、柠檬醛、香茅醛、香茅酰氧基乙醛、仙客来醛、羟基香茅醛、铃兰醛和波洁红醛(Bourgeonal),酮包括例如紫罗兰酮、◇-异甲基紫罗酮和甲基柏木酮,醇包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯乙醇和萜品醇,烃主要包括萜和香脂。然而,优选使用各种气味物质的混合物,这些混合物一起产生令人愉悦的香调。通常用作芳香组分的相对低挥发性的精油也适合作为香料油,例如鼠尾草油、春黄菊油、丁子香油、蜂花油、薄荷油、肉桂叶油、椴树花油、刺柏油、岩兰油、乳香油、古蓬油、岩蔷薇油和杂薰衣草油。优选以其本身或混合物形式使用香柠檬油、二氢月桂烯醇、铃兰醛、新铃兰醛(lyral)、香茅醇、苯乙醇、α-己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、乙氧基甲氧基环十一烷(boisambrene forte)、龙涎呋喃(ambroxan)、吲哚、二氢茉莉酮酸甲酯(hedione)、Sandelice、柠檬油、红橘油、橙油、戊基甘醇酸烯丙酯、女贞醛(cyclovertal)、杂薰衣草油、香紫苏油(muskateller salbeiol)、β-突厥酮、波旁香叶油(geraniumol bourbon)、水杨酸环己酯、vertofix coeur、龙涎酮(iso-E-Super)、FixolideNP、合成橡苔(evernyl)、γ-甲基紫罗兰酮(iraldein gamma)、苯乙酸、乙酸香叶酯、乙酸苄基酯、玫瑰醚、romilat、irotyl和floramat。
可能的芳香化合物是例如薄荷油(peppermint oil)、薄荷油(spearmint oil)、茴香油、八角茴香油、葛缕子籽油、桉叶油、小茴香油、柠檬油、冬青油、丁子香油、薄荷醇等。
染料:可以使用的染料是适合和批准用于化妆品目的的物质,例如总结在出版物“Kosmetische”,Dyestuffs Commission of the DeutscheForschungsgemeinschaft,Verlag Chemie,Weinheim,1984,第81-106页中。实例是胭脂红A(C.I.16255),专利蓝V(C.I.42051),靛蓝(C.I.73015),叶绿酸(C.I.75810),喹啉黄(C.I.47005),二氧化钛(C.I.77891),阴丹士林蓝RS(C.I.69800)和茜素红色淀(C.I.58000)。组合物还可以包含鲁米诺作为荧光染料。这些染料通常基于总混合物以0.001-0.1重量%的浓度使用。
杀菌和抑菌活性化合物:合适的杀菌和抑菌活性化合物的典型实例特别是壳聚糖和苯氧乙醇。也已证明特别有效的是5-氯-2-(2,4-二氯苯氧基)-苯酚,其由Ciba-Geigy,Basle/CH以商品名IrgasanΣ销售。合适的抑菌剂原则上是所有对革兰氏阳性细菌有活性的物质,例如4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)脲、2,4,4'-三氯-2'-羟基二苯基醚(三氯生)、4-氯-3,5-二甲基苯酚、2,2'-亚甲基双(6-溴-4-氯苯酚)、3-甲基-4-(1-甲基乙基)苯酚、2-苄基-4-氯苯酚、3-(4-氯苯氧基)-1,2-丙二醇、3-碘-2-丙炔基丁基氨基甲酸酯、氯己定、3,4,4'-三氯碳酰苯胺(TTC)、抗菌气味物质、百里香酚、百里香油、丁香酚、丁香油、薄荷醇、薄荷油、合金欢醇、苯氧乙醇、甘油单癸酸酯、甘油单辛酸酯、甘油单月桂酸酯(GML)、双甘油单癸酸酯(DMC)和水杨酸N-烷基酰胺如水杨酸正辛基酰胺或水杨酸正癸基酰胺。
吸汗物质:吸汗物质是例如改性淀粉,如Dry Flo Plus(National Starch)、硅酸盐、滑石和表现出适合吸汗的其他类似改性物质。本发明制剂可以包含基于化妆品和/或药物配制剂的总重量0.1-30重量%,优选1-20重量%,特别是2-8重量%的吸汗物质。
颜料以细碎的形式存在于颜料制剂中,因此通常具有0.02-5Σm的平均粒度。
有机颜料通常是有机的彩色和黑色颜料。无机颜料同样可以是有色颜料(彩色、黑色和白色颜料)以及珠光颜料和常规用作填料的无机颜料。
可以使用的颜料,特别是赋颜色性质的是氧化铁、二氧化钛、合成氟金云母和二氧化钛、云母和/或氧化锌。
本发明还提供乳液。在一个替换方案中,本发明乳剂,特别是防晒组合物包含以下组分或由以下组分组成:
本发明组合物,1-10%,优选4-6%;
乳化剂,0.5-5%,优选1.5-3%;
软化剂,优选使用各种软化剂,其比例总共为20-50%,优选25-35%;
UV过滤剂,优选使用各种过滤剂,其比例总共为10-35%,优选20-25%;软化水,5-50%,优选20-30%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
在另一替换方案中,本发明乳剂包含以下组分或由以下组分组成:本发明组合物,0.1-5%,优选1-2%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为1-20%,优选5-12%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.5-10%,优选2-5%,
流变物质,0.01-5%,优选0.1-1%;
抗氧化剂,0.01-10%,优选0.1-1%;
保湿剂,1-10%,优选2-8%,特别优选4-6%;
软化水,50-90%,优选75-85%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
本发明还提供霜剂。在另一替换方案中,本发明霜剂包含以下组分或由以下组分组成:
本发明组合物,0.1-10%,优选2-5%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为1-30%,优选10-20%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.1-10%,优选1.5-5%;
流变物质,0.01-5%,优选0.1-1%;
保湿剂,1-10%,优选2.5-5%;
软化水,50-90%,优选70-80%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
本发明还提供一种身体乳。在另一替换方案中,本发明的身体乳包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成:本发明组合物,0.1-10%,优选1-5%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为5-40%,优选20-25%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.5-20%,优选5-10%;
流变物质,0.01-5%,优选0.1-1%;
保湿剂,1-10%,优选2.5-7.5%;
软化水,40-80%,优选60-70%;
抗氧化剂,0.01-5%,优选0.1-1%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
本发明还提供装饰性化妆品的产品,例如
唇膏、唇彩、眼影、脂粉、胭脂、美容品、遮瑕化妆品、眼线笔、睫毛膏、黑色眼影(kajal)和
BB(遮瑕霜)产品,例如BB霜、BB粉底、BB遮瑕膏。
在一个替换方案中,本发明的BB(遮瑕霜)产品包含以下组分或由以下组分组成,使得所有成分的总和为100%:
纯水:至100%;丁二醇:1-10%,优选2-6%;氧化铁:0.01-5%,优选0.1-1%;二氧化钛:1-10%,优选3-7%;黄原胶::0.01-2%,优选0.05-1.0%;本发明组合物:1-10%,优选2-8%;十六/十八烷基磺基琥珀酸二钠:0.1-5%,优选1-3%;二乙基氨基羟基苯甲酰基己基苯甲酸酯:1-10%,优选2-6%;亚甲基双苯并三唑基四甲基丁基苯酚:1-10%,优选2-6%;甲氧基肉桂酸辛酯:1-10%,优选2-8%;双乙基己氧基苯酚甲氧基苯基三嗪:0.1-5%,优选0.5-3%;碳酸二辛酯:1-20%,优选2-15%;环聚甲基硅氧烷:1-10%,优选2-8%;碳酸亚丙酯:0.1-5%,优选0.2-2%;硬脂基二甲基苄基氯化铵和水辉石的反应产物:0.1-10%优选0.5-3%的合成氟金云母和二氧化钛:0.5-6%,优选1-3%;云母:1-10%,优选2-6%;氧化锌:10-30%,优选15-25%;滑石:1-10%,优选2-8%;聚丙烯酸钠:0.1-5%,优选0.5-2.26%;丙烯酸酯/甲基丙烯酰胺共聚物:1-10%,优选2-6%。
本发明还提供一种BB(遮瑕霜)身体霜,特别是防晒组合物。在另一替换方案中,本发明的身体霜包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成,使得所有成分的总和为100%:
本发明组合物,0.1-20%,优选1-10%;
乳化剂,0.01-5%,优选0.1-2%;
软化剂,优选使用各种软化剂,其比例总共为5-40%,优选10-30%;
填料,0.5-20%,优选1-10%;
UV过滤剂,优选使用各种软化剂,其比例总共为1-40%,优选10-30%;
流变物质,0.01-5%,优选0.1-2%;
保湿剂,0.1-10%,优选1-5%;
软化水,30-80%,优选40-50%;
效果颜料,优选使用各种软化剂,其比例总共为0.1-10%,优选1-7%;防腐剂,0.01-5%,优选0.1-2%。
本发明还提供BB(瑕疵膏)霜,特别是防晒组合物。在另一替换方案中,本发明的霜包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成,使得所有成分的总和为100%:
本发明组合物,0.1-20%,优选1-10%;
乳化剂,0.01-8%,优选0.1-3%;
软化剂,优选使用各种软化剂,其比例总共为5-40%,优选10-30%;
填料,0.5-10%,优选1-5%;
UV过滤剂,优选使用各种软化剂,其比例总共为1-40%,优选10-20%;
流变物质,0.01-10%,优选0.1-5%;
保湿剂,0.1-15%,优选2-10%;
软化水,20-70%,优选30-50%;
效果颜料,优选使用各种软化剂,其比例总共为0.1-10%,优选1-5%;
染料,优选使用各种软化剂,其比例总共为0.1-15%,优选2-10%。
防腐剂,0.01-5%,优选0.1-2%。
本发明还提供一种面膜。在另一替换方案中,本发明面膜包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成:本发明组合物,0.1-10%,优选1-5%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为5-30%,优选10-20%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.5-15%,优选2-5%;
流变物质,0.01-5%,优选0.1-1%;
保湿剂,1-10%,优选2-8%;
软化水,50-90%,优选65-75%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
本发明还提供一种护手霜。在另一替换方案中,本发明护手霜包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成,其包含本发明组合物和其他辅助物质:
本发明组合物,0.1-10%,优选1-5%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为1-20%,优选2-15%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.5-15%,优选2-5%;
流变物质,0.01-5%,优选0.1-1%;
保湿剂,1-30%,优选2 5-20%;
软化水,50-90%,优选65-75%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
本发明还提供一种精华液(serum)。在另一替换方案中,本发明精华液包含以下组分和任选其他辅助物质或由以下组分和任选其他辅助物质组成,其包含本发明组合物和其他辅助物质:
本发明组合物,0.1-10%,优选1-5%;
乳化剂,0.01-5%,优选0.1-1%;
软化剂,优选使用各种软化剂,其比例总共为1-20%,优选2-10%;
赋予稠度的试剂和增稠剂,优选使用各种试剂,其比例总共为0.1-10%,优选0.5-2%;
流变物质,0.01-5%,优选0.1-1%;
保湿剂,0.1-10%,优选1-5%;
软化水,60-95%,优选80-90%;
和其他添加剂,优选选自上文公开的那些的组的各种添加剂,使得所有成分的总和为100%。
在另一替换化妆品产品中,特别是装饰性化妆品中,选自下表:基于组合物,辅助物质和添加剂的总比例可以为1-50重量%,优选5-40重量%。组合物可以通过常规的冷或热方法制备。组合物可以通过反相温度法制备。
本发明组合物、本发明成形体和本发明方法显示出优异的感官性能并且使得使用可持续的和/或可再生的原料成为可能。这些原料不是石油化学产生的,而是植物或动物来源的,可用作营养领域(食品和饲料)外的物质或能量。
特别是在本发明的具有其中R1是碳长度为C16和/或C18的烷基和/或烯烃的酰基组分的碳水化合物偏酯的制备中,采用可持续的和/或可再生的(生物可再生的)原料。因此,在一个实施方案中将由棕榈油获得的十六/十八烷基甲基酯用于酯化或酯交换。
本发明方法可以有利地在实验室规模上应用,并且可以在工业规模上应用而无需修改。也就是说,可以将单独工艺步骤从实验室规模转化为工业规模而无需其他努力,但是在工业规模的工艺过程中温度变化为+/-10℃是可能的。在非本发明的其他方法中,这种温度变化可导致产率,特别是产品组成显著变化。
就工业规模的本发明而言,方法是其中将离析物,特别是碳水化合物和用于酯化的烷基酯以每种情况下大于1kg,优选至少5kg,至少10kg,特别优选至少25kg,50kg,特别是至少100kg的量使用的那些。
因此,本发明还提供符合Ecocert对天然化妆品和生物天然化妆品的要求的化妆品产品:
Ecocert天然化妆品
·所有成分的至少95%属于天然来源。
·终产物中所有组分的至少5%来源于生物培养
·至少50%的所用植物物质来源于生物培养
·不允许合成染料和芳香剂、合成脂肪、油、聚硅氧烷和原油产品
·没有用成品进行动物研究
·使用仅来自活体动物的动物原料
·只允许特定物质用于防腐
·禁止通过基因工程控制的原料
·不使用放射性辐照以消毒原料或产品
Ecocert生物天然化妆品:与仅天然化妆品相比,在此规定了受控生物培养的成分含量较高:
·所有成分的至少95%属于天然来源
·所有成分的至少10%来源于生物培养
·至少95%的所用植物物质来源于生物培养
·不允许合成染料和芳香剂、合成脂肪、油、聚硅氧烷和原油产品
·没有用成品进行动物研究
·使用仅来自活体动物的动物原料
·仅允许特定物质用于防腐
·禁止通过基因工程控制的原料
·不使用放射性辐照以消毒原料或产品
实施例:
1.本发明
蔗糖酯根据EP 1 811 951 B1的实施例1制备:
然而,在无催化剂失活下进行后处理。在每种情况下,在100℃下加入棕榈酸鲸蜡酯、硬脂酸己基癸酯和氢化棕榈油作为软化剂。
通过离心机或倾析器在100℃下倾析后,用浓度为35%的H2O2溶液进行漂白。在室温下存在几乎无色的固体。
GPC分析显示粗产物和终产物之间的碳水化合物偏酯分布没有变化。软化剂(酯油):
图1中的棕榈酸鲸蜡酯,图2中的硬脂酸己基癸酯,图3中的氢化棕榈油。
各图在上图显示本发明方法的步骤i)的特定粗产物的GPC,中间的图显示特定纯软化剂的GPC,下图显示特定终产物的GPC。
由终产物生产的锭剂硬而不脆。即使在40℃下储存超过一周也没有观察到“发汗”。锭剂在储存试验中也没有变得发粘。
实施例2:工业规模的本发明产物的合成:
使用Cutina CP的蔗糖聚硬脂酸酯
a)合成:
首先在70℃下将393kg熔融甲酯(Edenor ME AS 16V,十六/十八烷基甲基酯,BASF)引入具有加热、搅拌器、真空装置和氮气进料的反应器中,将容器用氮气惰性化并在彻底混合下连续加入16.3g碳酸钾,124kg Sisterna SP-30C(蔗糖二硬脂酸酯),266kg粉状糖和1.3kg次磷酸钠。除去水(85℃,5毫巴,90分钟)后,将混合物缓慢加热至135℃,真空除去形成的甲醇。反应结束时反应混合物中棕榈酸甲酯的含量小于3%。将粗产物冷却至100℃,并搅拌加入85kg棕榈酸鲸蜡酯(Cutina CP)。
b)后处理:
通过借助倾析器(例如来自Siebtechnik,TS 210的倾析离心机)分离出未反应的糖(氮气气氛,100℃)而将产物中剩余糖的含量降至3.8%。随后的过滤(约10kg过滤助剂Seitz Ultra,滤片K900,Pall,氮气气氛,100℃)将剩余糖含量(通过GC测定)降至仅3.4%。
GPC分析得到如图1所示的相同结果。
为了漂白,使产物在75-80℃下在氮气气氛下置于合适的反应器中,在彻底搅拌下缓慢加入6kg过氧化氢(浓度为35%),以避免过度起泡和在90℃以上的温度升高。随后将混合物搅拌约60分钟,直至过氧化物值在5毫摩尔O2/kg以下。
3.对比例
对比例类似于实施例1而进行。然而,各自使用图4中的山萮醇和图5中的辛酸/癸酸甘油三酯(Myritol 312)作为软化剂。
GPC分析显示在每种情况下在粗产物和终产物之间不同的碳水化合物偏酯分布。
4.工业规模的对比例
非本发明的产物的合成如实施例2所述进行;然而,使用90kg的Myritol 312代替Cutina CP作为酯油。
在后处理过程中,过滤后的剩余糖含量可降至2.4%。然而,终产物显示与粗酯相比显著改变的酯分布,如图5所示。
在使用C8/10-甘油三酯作为酯油时,后处理过程中蔗糖酯的酯组成显著变化,使得未实现本发明的目的。
类似于实施例4和5的相应实验也可以使用非根据本发明使用的其他酯油(软化剂),例如其中醇组分R3是甲基或乙基或链长小于8个碳原子的其他烷基的酯油而进行。
5.本发明产物中的醇含量:
本发明的酯油的酸基转移到蔗糖酯中,伴随着相应稀释剂醇基的释放。当使用根据本发明使用的酯油(例如Cutina CP)时,在其分离之后,因此必然在最终产物中可检测出棕榈醇和硬脂醇的混合物;例如通过气相色谱法。就稳定性研究而言,本发明产物在120℃下储存24小时。
该研究的起始和最终材料的GC即使在24h后也没有显示棕榈醇和硬脂醇的谱带。
6.倾析
实施例1和2显示,在本发明方法中,用于分离出剩余糖的倾析得到令人满意的结果(=剩余糖含量)。因此,不需要对粗产物进行耗时过滤。此外,倾析后的过滤仅不显著进一步降低了剩余糖含量。
Claims (18)
1.一种组合物,包含:
a1)作为具有式R1-COO的酰基组分的至少一种碳水化合物的酯化产物的碳水化合物偏酯,
b1)式R1-COO-R2的烷基酯,和
c1)式R1-COO-R3的酯油,
和任选地碳水化合物、催化剂、脂肪酸和/或脂肪皂;
其中
酯b1)的醇组分R2是C1-C3醇单元,酯油c1)具有选自以下的醇组分R3:
i)具有C8-C22的支化和非支化醇,或
ii)多元醇,或
iii)其混合物
将其用选自链长度为C6-C22的单酸和二酸或任何组合的酰基组分R1完全酯化,
其中所述组合物的水含量为<5重量%,
其中酯a1)、b1)和c1)的所有酰基组分相同。
2.一种组合物,其包含:
a2)平均酯化度为1-4的碳水化合物偏酯,
b2)具有含有6-22个碳原子的酰基组分的有机烷基酯,酯b2)的醇组分R2是C1-C3醇单元,
c2)具有含有6-22个碳原子的直链酰基组分和含有8-22个碳原子的直链醇组分的酯油,
和任选地碳水化合物、催化剂、脂肪酸和/或脂肪皂,
其中所述组合物的水含量为<5重量%,
其中酯a2)、b2)和c2)的所有酰基组分相同。
3.根据权利要求1或2的组合物,其特征在于产物a1)或a2)是具有b1)或b2)的酰基组分的糖的碳水化合物偏酯。
4.根据权利要求3的组合物,其特征在于糖是单糖和/或二糖。
5.根据权利要求1或2的组合物,其特征在于酯a1)、b1)、c1)、a2)、b2)或c2)的至少一个酰基组分是具有16和/或18个碳原子的脂肪酸基团。
6.根据权利要求1或2的组合物,其特征在于酯油c1)或c2)的醇组分是具有16和/或18个碳原子的脂肪醇。
7.根据权利要求1的组合物,其特征在于酯油c1)的醇组分是具有16-20个碳原子的格尔伯特醇或选自以下的多元醇:乙二醇、丙二醇、丁二醇、新戊二醇、甘油,其被完全酯化。
8.根据权利要求1或2的组合物,其特征在于碳水化合物偏酯包含:
比例为0-20%的单酯,
比例为10-40%的二酯,
比例为20-50%的三酯,和
比例为15-40%的四酯,
其中总和为100%。
9.根据权利要求1或2的组合物,其特征在于在偏酯中,单酯:二酯:三酯:四酯的比例为0.5-1.5:3.0-4.0:4.0-5.0:3.0-4.0。
10.一种成形体,包含根据权利要求1-9中任一项的组合物。
11.根据权利要求10的成形体,由根据权利要求1-9中任一项的组合物组成。
12.一种用于制备根据权利要求1-9中任一项的组合物或根据权利要求10或11的成形体的方法,其特征在于以下步骤:
i)使碳水化合物与烷基酯b1)或b2)在催化剂存在下酯化或酯交换,
ii)加入酯油c1)或c2),
iii)从粗产物中分离出剩余的碳水化合物,任选地
iv)漂白分离出的包含粗产物的液相,和任选地
v)制备成形体。
13.根据权利要求12的方法,其特征在于酯a1)、b1)、c1)、a2)、b2)和/或c2)的酰基组分R1是具有16和/或18个碳原子的脂肪酸基团。
14.根据权利要求12的方法,其特征在于不进行催化剂失活。
15.根据权利要求13的方法,其特征在于来自步骤i)的产物具有与来自步骤iii)、iv)或v)的产物之一相同的碳水化合物偏酯分布。
16.一种包含根据权利要求1-9中任一项的组合物或根据权利要求10或11的成形体或根据权利要求12-15中任一项的方法制备的产物的化妆品。
17.一种包含根据权利要求1-9中任一项的组合物或根据权利要求10或11的成形体或根据权利要求12-15中任一项的方法制备的产物的药物产物。
18.一种包含根据权利要求1-9中任一项的组合物或根据权利要求10或11的成形体或根据权利要求12-15中任一项的方法制备的产物的食品。
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EP14197689.4A EP3031443A1 (de) | 2014-12-12 | 2014-12-12 | Zusammensetzung enthaltend Kohlehydratpartialester |
PCT/EP2015/079472 WO2016092088A1 (de) | 2014-12-12 | 2015-12-11 | Zusammensetzung enthaltend kohlehydratpartialester |
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CN1187765A (zh) * | 1994-11-28 | 1998-07-15 | 普罗克特和甘保尔公司 | 以含增稠的羧酸多元醇酯为皮肤调理剂的局部护肤组合物 |
CN101056609A (zh) * | 2004-11-10 | 2007-10-17 | 考格尼斯知识产权管理有限责任公司 | 制备碳水化物偏酯的方法 |
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DE1165574B (de) | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Verfahren zur Herstellung von als Emulgiermittel fuer Salbengrundlagen dienenden Mischestern |
GB1399053A (en) | 1973-03-16 | 1975-06-25 | Tate & Lyle Ltd | Process for the production of surface active agents comprising sucrose esters |
LU68901A1 (zh) | 1973-11-30 | 1975-08-20 | ||
GB1499989A (en) | 1974-10-17 | 1978-02-01 | Tate & Lyle Ltd | Production of a surface active material containing sucrose esters |
DE3588086T2 (de) | 1984-11-05 | 1996-09-19 | Hitachi Ltd | Supraleiteranordnung |
US4983731A (en) | 1989-03-17 | 1991-01-08 | Nebraska Department Of Economic Development | Separation and purification of sugar esters |
JP3836162B2 (ja) | 1993-10-18 | 2006-10-18 | 東和化成工業株式会社 | ショ糖脂肪酸エステルの製造方法 |
DE4426215A1 (de) | 1994-07-23 | 1996-01-25 | Merck Patent Gmbh | Ketotricyclo [5.2.1.0] decan-Derivate |
DE4426216A1 (de) | 1994-07-23 | 1996-01-25 | Merck Patent Gmbh | Benzyliden-Norcampher-Derivate |
WO1996016636A1 (en) * | 1994-11-28 | 1996-06-06 | The Procter & Gamble Company | Topical skin care compositions containing thickened polyol carboxylic acid esters as skin conditioning agents |
DE59709127D1 (de) | 1996-07-08 | 2003-02-20 | Ciba Sc Holding Ag | Triazinderivate als UV-Filter in Sonnenschutzmitteln |
DE19712033A1 (de) | 1997-03-21 | 1998-09-24 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
US5945519A (en) | 1997-06-17 | 1999-08-31 | Th Goldschmidt Ag | Process for the preparation of sucrose fatty acid esters |
DE19756377A1 (de) | 1997-12-18 | 1999-06-24 | Beiersdorf Ag | Verwendung von C¶1¶¶8¶-¶3¶¶8¶-Alkylhydroxystearoylstearat zur Verstärkung der UV-A-Schutzleistung kosmetischer oder dermatologischer Formulierungen |
DE69920745T2 (de) * | 1998-12-05 | 2005-10-06 | Imperial Chemical Industries Plc, Millbank | Emulgiersystem und emulsionen |
JP4906040B2 (ja) * | 2004-08-24 | 2012-03-28 | 株式会社 資生堂 | 油性化粧料 |
EP1958612B1 (en) * | 2005-11-30 | 2014-07-02 | The Nisshin OilliO Group, Ltd. | Trehalose fatty acid ester composition |
EP2269566A1 (en) * | 2009-06-30 | 2011-01-05 | Cognis IP Management GmbH | Ester mixtures and compositions comprising such ester mixtures |
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CN1187765A (zh) * | 1994-11-28 | 1998-07-15 | 普罗克特和甘保尔公司 | 以含增稠的羧酸多元醇酯为皮肤调理剂的局部护肤组合物 |
CN101056609A (zh) * | 2004-11-10 | 2007-10-17 | 考格尼斯知识产权管理有限责任公司 | 制备碳水化物偏酯的方法 |
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EP3229750A1 (de) | 2017-10-18 |
BR112017012524A2 (pt) | 2018-02-27 |
KR102588039B1 (ko) | 2023-10-11 |
EP3229750B1 (de) | 2022-02-09 |
US10357569B2 (en) | 2019-07-23 |
EP3031443A1 (de) | 2016-06-15 |
CN107249553A (zh) | 2017-10-13 |
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KR20170094380A (ko) | 2017-08-17 |
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