CN114340775A - 有机化合物中或与之相关的改进 - Google Patents
有机化合物中或与之相关的改进 Download PDFInfo
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- CN114340775A CN114340775A CN202080060930.XA CN202080060930A CN114340775A CN 114340775 A CN114340775 A CN 114340775A CN 202080060930 A CN202080060930 A CN 202080060930A CN 114340775 A CN114340775 A CN 114340775A
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- chitosan
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Abstract
描述了一种包封的组合物,其包含至少一种芯‑壳微胶囊。所述至少一种芯‑壳微胶囊包含芯和包围所述芯的壳,所述芯包含至少一种有益剂。所述壳包含通过至少一种三官能异氰酸酯与至少一种不是脱乙酰壳多糖的多官能胺的反应形成的聚脲树脂。所述至少一种三官能异氰酸酯为脂族三元醇与至少一种芳脂族二异氰酸酯的加合物。衍生自所述三官能异氰酸酯的聚脲树脂部分与所述芯之间的重量比为0.09至0.30,优选0.10至0.20,更优选0.11至0.18。所述壳还包含脱乙酰壳多糖。本公开还涉及制备这类包封的组合物的方法以及它们在增强消费品中有益剂的性能中的用途。
Description
本发明涉及包含至少一种芯-壳微胶囊的包封的组合物。本发明还涉及制备此类组合物的方法以及它们用于增强消费品中有益剂的性能的用途。
已知将包封的有益剂掺入消费品中,例如家庭护理,个人护理和织物护理产品。有益剂包括例如香料,化妆品试剂,食品成分,营养保健食品(nutraceuticals),药物和基质增强剂。
特别适合递送此类有益剂的微胶囊为芯-壳微胶囊,其中所述芯通常包含有益剂并且所述壳对有益剂是不可渗透的或部分不可渗透的。通常,这些微胶囊用于水性介质中并且包封的有益剂是疏水的。可以使用广泛选择的壳材,条件是壳材对包封的有益剂是不可渗透的或部分不可渗透的。
出于多种原因将有益剂包封。微胶囊可以隔离和保护这些材料免受外部悬浮介质例如消费品基料的影响,在其中它们可能不相容或不稳定。它们还用于辅助将有益剂沉积在基质例如皮肤或头发上,或者在香料成分的情况下,也用于织物或坚硬的家居表面。它们还可以作为控制有益剂时空释放的方式。
现有技术中已经提出了多种适用于制备包封的组合物的包封介质以及有益剂。这种包封介质包括由聚酰胺,聚脲,聚氨酯,聚丙烯酸酯,蜜胺衍生的树脂或其混合物制成的合成树脂。
在许多情况下,此类微胶囊在光滑表面上且尤其是在角质表面如皮肤和头发上的沉积和粘附不充分,并且与使用微胶囊相关的预期益处并非最佳。对于涉及大量水的冲洗型产品尤其如此。在这种情况下,缺乏沉积可能归因于微胶囊的稀释。大量的冲洗水也可能从表面冲洗掉微胶囊。
WO2011/161229A1描述了包封的香料组合物,其包含芯-壳微胶囊,其中壳由聚脲树脂制成,所述聚脲树脂通过两种结构不同的异氰酸酯反应形成。这些微胶囊在冲洗应用中表现出良好的角质表面沉积。
然而,已经发现,特别是在头发护理中,冲洗后干燥的方法对微胶囊带来的益处具有显著影响。虽然使用空气干燥通常观察到良好的沉积和粘附,但使用吹风机会导致性能下降。
因此,基于本发明的问题在于克服现有技术中的上述缺点。特别地,基于本发明的问题在于提供上述类型的包封的组合物,其在用吹风机干燥毛发后在毛发上表现出改善的沉积和粘附。这些微胶囊在制造,储存和应用过程中应保持其期望的有益剂释放特性。此外,该组合物应当可以在操作安全,稳定和成本有效的过程中生产。
这些问题通过本发明的包封的组合物得到解决。这种组合物包含至少一种芯-壳微胶囊。所述至少一种芯-壳微胶囊包含芯和包围所述芯的壳,所述芯包含至少一种有益剂。所述壳包含通过至少一种三官能异氰酸酯与至少一种不是脱乙酰壳多糖的多官能胺的反应形成的聚脲树脂。所述至少一种三官能异氰酸酯为脂族三元醇与至少一种芳脂族(araliphatic)二异氰酸酯的加合物。衍生自所述三官能异氰酸酯的聚脲树脂部分与所述芯之间的重量比为0.09至0.30,优选为0.10至0.20,更优选为0.11至0.18。所述壳还包含脱乙酰壳多糖。
在本上下文中,术语“有益剂”是指当添加到产品中时可以改善消费者对该产品的感知或可以增强该产品在应用中的作用的任何物质。典型的有益剂包括香料成分,调味剂成分,化妆品成分,生物活性剂(例如杀菌剂,驱虫剂和信息素),基质增强剂(如聚硅氧烷和增亮剂),酶(例如脂肪酶和蛋白酶),染料,颜料和营养保健食品。
有机异氰酸酯为其中异氰酸酯基团结合至有机残基的化合物(R-N=C=O或R-NCO)。在本发明的上下文中,多异氰酸酯(或多官能异氰酸酯)为在分子上带有两个或多个(例如3,4,5个等)异氰酸酯基团的有机异氰酸酯。三官能异氰酸酯为在分子上带有3个异氰酸酯基团的异氰酸酯。
正如本领域已知的,脱乙酰壳多糖为衍生自壳多糖的生物聚合物,其形成甲壳类动物的外骨骼并保持各种真菌,例如子囊菌纲(Ascomycetes),接合菌亚纲(Zygomycetes),担子菌纲(Basidiomycetes)和半知菌(Deuteromycetes),例如犁头霉属(Absidia),毛霉菌属(Mucor),黑曲霉菌(Aspergillus Niger),灵芝(Ganoderma Lucidum)和稻根霉菌(Rhizopus Oryzae)的形状。脱乙酰壳多糖生产牵涉壳多糖的碱性或酶促脱乙酰作用,且其特征在于脱乙酰度(deacetylation grade)。低脱乙酰度(典型地低于80%)和高脱乙酰度(典型地高于或等于80%脱乙酰度)均存在。脱乙酰的脱乙酰壳多糖是由N-乙酰基-D-葡糖胺和D-葡糖胺部分组成的共聚物。脱乙酰度可以通过1H和/或13C核磁共振波谱法确定。脱乙酰壳多糖以典型地3’000至5’000’000g/mol的分子量得到。根据本领域已知的方法,可以通过粘度测量和/或凝胶渗透色谱法测定分子量。
在本发明的上下文中,术语“不是脱乙酰壳多糖的多官能胺”表示包含至少两个能够与NCO基团反应的基团的胺,其中能够与NCO基团反应的基团的至少一个为伯氨基或仲氨基。这些胺在结构上与脱乙酰壳多糖不同。当多官能胺仅包含一个伯氨基或仲氨基时,其包含一个或多个能够在聚合反应中与NCO基团反应的另外的官能团。对NCO基团具有反应性的多官能胺的基团优选选自羟基和伯氨基或仲氨基。NCO基团与氨基的反应导致脲基形成。NCO基团与OH基团的反应导致尿烷(urethane)基团形成。然而。与OH基团的反应通常需要催化剂。导入的多官能胺的量相对于转化游离异氰酸酯基团所需的化学计算量通常为摩尔过量的。
通常,“芳脂族异氰酸酯或多异氰酸酯”为其中至少一个异氰酸酯基团通过烷基残基,特别是亚甲基残基结合至芳族残基的化合物。
为了避免任何歧义,“壳还包含脱乙酰壳多糖”并不一定意味着,在包封期间,脱乙酰壳多糖发生与其他成壳材料,特别是与所述至少一种三官能异氰酸酯的反应,以构成聚脲树脂,虽然很可能确实是这种情况,正如下文进一步解释的。更特别地,本发明还包括其中微胶囊壳例如包含脱乙酰壳多糖涂层的情况,这意味着脱乙酰壳多糖沉积在所述壳上。另一方面,脱乙酰壳多糖也可以包埋在微胶囊的壳中。
在解决现有技术的问题时,已经发现在聚脲微胶囊壳的形成中使用特定量的至少一种三官能异氰酸酯与脱乙酰壳多糖的组合导致胶囊在用吹风机干燥头发后胶囊在头发上的沉积和粘附得到改善。
脂族三元醇可以选自2-乙基丙-1,2,3-三醇和2-乙基-2-(羟基甲基)丙-1,3-二醇,优选2-乙基丙-1,2,3-三醇。
优选地,所述至少一种芳脂族二异氰酸酯选自1,2-双(异氰酸基甲基)苯,1,3-双(异氰酸基甲基)苯,1,4-双(异氰酸基甲基)苯,1-异氰酸基-2-(异氰酸基甲基)苯,1-异氰酸基-3-(异氰酸基甲基)苯和1-异氰酸基-4-(异氰酸基甲基)苯。
此类三官能异氰酸酯可在商标Takenate D-110N(ex Mitsui)或Desmodur Quix175(ex Covestro)下得到。这种异氰酸酯具有比脂族多异氰酸酯更具反应性并且比芳族多异氰酸酯具有更低反应性的优点。不受任何理论的束缚,可以推定,由于这种中间反应性,芳脂族多异氰酸酯与多官能胺的加聚过程中形成的聚脲树脂比使用芳族多异氰酸酯得到的聚脲树脂更均匀地交联。另一方面,交联比用脂族多异氰酸酯得到的交联更有效。
在本发明的一个具体的实施方案中,三官能异氰酸酯为2-乙基丙-1,2,3-三醇和1,3-双(异氰酸基甲基)苯的加合物。
如前所述,在本发明的一个优选实施方案中,脱乙酰壳多糖沉积在包围所述芯的壳的外表面上和/或脱乙酰壳多糖包埋在包围所述芯的壳中。在这种情况下,该组合物可以还包含游离脱乙酰壳多糖,因为可能发生脱乙酰壳多糖的吸附/解吸平衡。
在本发明的上下文中,术语“游离脱乙酰壳多糖”用于描述当微胶囊分散在分散介质中时,通过分散介质在空间上与微胶囊分离的脱乙酰壳多糖。
另一方面,聚脲树脂也可以通过所述至少一种三官能异氰酸酯与所述至少一种不是脱乙酰壳多糖的多官能胺和与所述脱乙酰壳多糖反应而形成。不受任何理论的束缚,本申请人认为使用脱乙酰壳多糖作为聚脲树脂形成过程中的活性种类使该树脂更具粘弹性,进而促进微胶囊壳与基质的粘附。
在本发明的另一个优选的实施方案中,聚脲树脂通过所述至少一种三官能异氰酸酯和水可分散性多异氰酸酯与至少一种不是脱乙酰壳多糖的多官能胺的反应来形成,并且任选地与脱乙酰壳多糖的反应来形成。
在本文的上下文中,“水可分散性多异氰酸酯”是指可以分散在水性介质中的细固体颗粒或液滴形式的多异氰酸酯。
适合的水可分散性多异氰酸酯为,例如芳族,脂环族或脂族的。
水可分散性多异氰酸酯优选为阴离子改性的多异氰酸酯。阴离子改性的多异氰酸酯包含至少两个异氰酸酯基团和至少一个为阴离子或阴离子源性(anionogenic)的官能团。“阴离子源性官能团”为取决于化学环境例如pH的不同可以变成阴离子的基团。适合的阴离子或阴离子源性基团为,例如羧酸基团,磺酸基团,膦酸基团及其盐。
阴离子改性的多异氰酸酯可以包含一个或多个磺酸基团或其盐。适合的盐可以为钠,钾或铵盐。优选铵盐。
优选地,阴离子改性的多异氰酸酯通过多异氰酸酯与2-(环己基氨基)-乙磺酸和/或3-(环己基氨基)-丙磺酸的反应来得到。
更优选地,阴离子改性的多异氰酸酯通过多异氰酸酯与2-(环己基氨基)-乙磺酸和/或3-(环己基氨基)-丙磺酸的反应来得到,其中所述多异氰酸酯选自六亚甲基二异氰酸酯,四亚甲基二异氰酸酯,异佛尔酮二异氰酸酯,二环己基甲烷-4,4’-二异氰酸酯,2,4-和2,6-甲苯二异氰酸酯及其异构体混合物,二苯基甲烷二异氰酸酯,缩二脲,脲基甲酸酯和/或上述多异氰酸酯的异氰脲酸酯。
在每种情况中,阴离子改性的多异氰酸酯可以选自阴离子改性的六亚甲基二异氰酸酯,异佛尔酮二异氰酸酯,二环己基甲烷-4,4’-二异氰酸酯,六亚甲基二异氰酸酯的异氰脲酸酯及其混合物。
优选地,所述阴离子改性的多异氰酸酯具有:
-至少1.8的平均异氰酸酯官能度,
-4.0至26.0wt.-%的异氰酸酯基团含量(计算为NCO;分子量=42),
-0.1至7.7wt.-%的磺酸酯基团含量(计算为SO3;分子量=80),和
-任选地0至19.5wt.-%的聚醚链中键合的环氧乙烷单元含量(计算为C2H2O;分子量=44),其中聚醚链含有5至55个环氧乙烷单元的统计学平均值。
在本发明的一个优选的实施方案中,水可分散性多异氰酸酯为基于六亚甲基二异氰酸酯的水可分散性的多异氰酸酯。更特别地,阴离子改性的多异氰酸酯可以选自阴离子改性的六亚甲基二异氰酸酯,阴离子改性的六亚甲基二异氰酸酯的异氰脲酸酯及其混合物。
在一个特别优选的实施方案中,所述阴离子改性的多异氰酸酯是根据式(1)的。
式(1)显示了商购的阴离子改性的多异氰酸酯,其为改性的六亚甲基二异氰酸酯的异氰脲酸酯,由Covestro以商标Bayhydur XP2547销售。
衍生自所述水可分离性多异氰酸酯的聚脲树脂的部分与所述芯的重量比可以为0.001至0.2,优选为0.005至0.1,更优选为0.01至0.05。
不是脱乙酰壳多糖的多官能胺优选选自二胺,三胺,四胺和更高级的多官能胺,氨基醇,蜜胺,脲,肼,聚合多胺及其混合物。
适合的二胺为,例如1,2-乙二胺,1,3-丙二胺,1,4-二氨基丁烷,1,5-二氨基戊烷,1,6-二氨基己烷,1,3-二氨基-1-甲基丙烷,1,4-二氨基环己烷,哌嗪或其混合物。
适合的氨基醇为,例如2-氨基乙醇,2-(N-甲基氨基)乙醇,3-氨基丙醇,4-氨基丁醇,1-乙基氨基丁-2-醇,2-氨基-2-甲基-1-丙醇,4-甲基-4-氨基戊-2-醇或其混合物。
适合的聚合多胺主要为直链或支链聚合物,其具有至少两个伯氨基或仲氨基。另外,这些聚合物可以在聚合物链上具有叔氨基。
所述聚合多胺优选选自聚亚烷基胺,聚乙烯胺,聚醚胺及其混合物。更优选地,所述聚合多胺选自聚(亚烷基亚胺),特别是聚(乙烯亚胺)。
优选具有重均分子量为至少300g/mol的聚合多胺。更优选具有重均分子量为500至2’000’000g/mol,特别地为700至1’000’000g/mol,甚至更特别地为800至500’000g/mol的聚合多胺。
在一个优选的实施方案中,不是脱乙酰壳多糖的多官能胺为聚(乙烯亚胺)。
聚(乙烯亚胺)可以为短链聚(乙烯亚胺),其具有式H2N(CH2CH2NH)nH,其中n为>1的整数(n=2:二亚乙基三胺;n=3:三亚乙基四胺;n=4:四亚乙基五胺)。它们有时称作聚(乙烯亚胺)或聚(亚烷基多胺)。聚(乙烯亚胺)还可以为长链聚(乙烯亚胺)。
根据本发明,优选使用具有至少500g/mol,优选600至30’000或650至25’000g/mol且特别是700至10’000g/mol或850至5’000g/mol的分子量的聚(乙烯亚胺)。
多官能胺可以为包含如下重复单元的聚(乙烯亚胺):
其中
-x为8至1’500,优选10至1’000;
-y为0至10,优选0至5,尤其是0;
-z为2+y。
使用这些聚(乙烯亚胺)可以得到良好的效果,特别是在提取介质中的渗漏方面。
优选的聚(乙烯亚胺)为直链聚(乙烯亚胺),其中x为8至1500,y为0,且z为2。
优选的商购聚(乙烯亚胺)由BASF SE在商标Lupasol,特别是Lupasol G100下销售。
衍生自所述多官能胺的聚脲树脂部分与所述芯之间的重量比可以为0.01至0.1,优选为0.015至0.05,且更优选为0.018至0.025。
在本发明的一个优选实施方案中,所述壳还包含阳离子聚合物。一方面,已知阳离子聚合物可改善微胶囊在各种基质如织物,皮肤和头发上的沉积和耐冲洗性。另一方面,阳离子聚合物也可以作为分散助剂起作用。
阳离子聚合物可以为两性聚合物。在本发明的上下文中,“两性聚合物”应理解为包含阳离子和阴离子基团或包含相应可电离基团的聚合物。阳离子两性聚合物包含比阴离子基团或可以形成阴离子的基团更多的阳离子基团,且照此具有净正电荷。
两性聚合物可以包含1至99mol-%的阳离子基团和1至99mol-%的阴离子基团或可以形成阴离子的基团。在本发明的一个优选实施方案中,两性聚合物包含2至99mol-%,特别地为30至95mol-%,且更特别地为60至90mol-%的阳离子基团和1至98mol-%,特别地为5至70mol-%,且更特别地为10至40mol-%的阴离子基团或可以形成阴离子的基团。
阳离子聚合物中的阳离子基团可以不依赖于pH。阳离子聚合物中的阳离子基团可以为季铵基团。
阳离子聚合物可以衍生自至少一种带有季铵官能团的单体。特别地,阳离子单体可以选自季铵化丙烯酸二甲基氨基乙酯(ADAME),季铵化甲基丙烯酸二甲基氨基乙酯(MADAME),二甲基二烯丙基氯化铵(DADMAC),丙烯酰氨基丙基三甲基氯化铵(APTAC)和甲基丙烯酰氨基丙基三甲基氯化铵(MAPTAC)。
当阳离子聚合物包含阴离子基团或可以形成阴离子的基团时,其还可以衍生自选自基于丙烯酸的单体和强酸单体的单体,所述基于丙烯酸的单体包括丙烯酸,甲基丙烯酸,衣康酸,巴豆酸,马来酸,富马酸,所述强酸单体例如为具有磺酸或膦酸型官能团的单体,例如2-丙烯酰氨基-2-甲基丙磺酸,乙烯基磺酸,乙烯基膦酸,烯丙基磺酸,烯丙基膦酸,苯乙烯磺酸。基于丙烯酸的单体还可以为这些单体的任何水溶性盐,其中所述盐为碱金属盐,碱土金属盐或铵盐。最优选的基于丙烯酸的单体为丙烯酸,甲基丙烯酸或其水溶性盐。
阳离子聚合物可以进一步衍生自非离子单体,所述非离子单体选自水溶性乙烯基单体,更特别地为丙烯酰胺,甲基丙烯酰胺,N-异丙基丙烯酰胺,N,N-二甲基丙烯酰胺,N-羟甲基丙烯酰胺,N-乙烯基甲酰胺,N-乙烯基乙酰胺,N-乙烯基吡啶和/或N-乙烯基吡咯烷酮。
阳离子聚合物可以为衍生自阳离子单体或可以形成阳离子的单体,特别是包含至少一个季铵基团的单体,阴离子单体或可以形成阴离子的单体,特别是基于丙烯酸,甲基丙烯酸或其衍生物的单体,和任选的非离子单体的两性共聚物。这类聚合物提供了与壳相容,具有良好分散效率,良好流动性能和与上文举出的各种基质的优异亲合力的最佳组合。
在一个更具体的实施方案中,两性共聚物为丙烯酸或甲基丙烯酸与丙烯酰氨基丙基三甲基氯化铵(APTAC)或甲基丙烯酰氨基丙基三甲基氯化铵(MAPTAC)的共聚物,例如WO2016/207180A1或WO2016/207187A1中所述。
仍然在一个更具体的实施方案中,两性共聚物为由丙烯酸单体,MAPTAC单体和丙烯酰胺单体形成的三元共聚物。
在一个更优选的实施方案中,丙烯酸/MAPTAC共聚物,且更特别地三元共聚物通过使1至2摩尔当量的丙烯酸单体与4摩尔当量的MAPTAC单体,更特别地1摩尔当量的丙烯酸单体与4摩尔当量的MAPTAC单体(例如Floset CAPS 371L),且仍然更特别地1.6摩尔当量的丙烯酸单体与4摩尔当量的MAPTAC单体反应而形成。
尽管在本发明的上下文中,Floset CAPS 371L是一种优选的阳离子聚合物,但它也可以被上述段落中所述的任何其他丙烯酸/MAPTAC共聚物替代。另一种优选的基于MAPTAC/丙烯酰胺的阳离子聚合物为Salcare SC60,其商购自BASF。在本发明的一个实施方案中,该共聚物具有为100,000g/mol,更特别地至少为500,000g/mol的分子量。
具有较低分子量的聚合物无法提供期望的性能,而具有较高分子量的聚合物会在很大程度上增加乳液和微胶囊分散体的粘度。
两性聚合物与芯的重量比可以为0.04至0.20,优选为0.07至0.15,更优选为0.8至0.12。
可以使用本领域技术人员众所周知的聚合技术制备两性聚合物。这些已知的聚合技术包括溶液聚合,凝胶聚合,沉淀聚合,反相乳液聚合,水性乳液聚合,悬浮聚合和胶束聚合。
优选地,所述脱乙酰壳多糖和/或衍生自所述脱乙酰壳多糖的聚脲树脂部分与所述芯之间的重量比为0.002至0.01,优选为0.004至0.008,更优选为0.006至0.007。脱乙酰壳多糖的水平受到其在微囊化过程中的普遍条件下的溶解度限制。如果脱乙酰壳多糖的水平过高,则该聚合物的一部分将沉淀在微胶囊浆液中。相反,如果脱乙酰壳多糖水平过低,则不存在期望的益处。
脱乙酰壳多糖可以具有5’000至1’000’000g/mol,优选7’500至500’000g/mol,仍然更优选10’000至250’000g/mol的平均分子量。如果脱乙酰壳多糖的分子量过高,则微胶囊可能会结块。如果脱乙酰壳多糖的分子量过低,则微胶囊在角质表面上的沉积和粘附可能不足。
脱乙酰壳多糖可以具有高于60%,优选高于70%,更优选高于80%的平均脱乙酰度。具有这种高脱乙酰度的脱乙酰壳多糖比具有较低乙酰化度的脱乙酰壳多糖更易溶解且由此更适合于本发明。
在本发明的上下文中,脱乙酰壳多糖的来源可以选自甲壳类动物(即虾脱乙酰壳多糖)或真菌(即蘑菇脱乙酰壳多糖)。蘑菇脱乙酰壳多糖的应用具有如下优点:可以得到完全由非动物来源的或换句话说为素食的微胶囊。一些消费者倾向于赞同具有完全非动物来源的材料。
有益剂可以选自至少一种香料成分和至少一种化妆品成分。
所述至少一种香料成分可以选自ADOXALTM(2,6,10-三甲基十一碳-9-烯醛);AGRUMEXTM(乙酸2-(叔丁基)环己酯);癸醛C 10(癸醛);醛C 11 MOA(2-甲基癸醛);十一碳烯醛C11(十一碳-10-烯醛);十一醛C 110(十一醛);月桂醛C 12(十二醛);醛C 12 MNA PURE(2-甲基十一醛);醛ISO C 11((E)-十一碳-9-烯醛);红桔醛10%/TEC((E)-十二碳-2-烯醛);烯丙基戊基乙醇酸酯(2-(异戊氧基)乙酸烯丙酯);烯丙基环己基丙酸酯(3-环己基丙酸烯丙酯);庚酸烯丙酯(庚酸烯丙酯);AMBER CORETM(1-((2-(叔丁基)环己基)氧基)丁-2-醇);AMBERMAXTM(1,3,4,5,6,7-六氢-β,1,1,5,5-五甲基-2H-2,4a-亚甲基萘-8-乙醇);水杨酸戊酯(2-羟基苯甲酸戊酯);阿弗曼酯(甲酸1-(3,3-二甲基环己基)乙酯);BELAMBRETM((1R,2S,4R)-2’-异丙基-1,7,7-三甲基螺[二环[2.2.1]庚烷-2,4’-[1,3]二噁烷]);BIGARYL(8-(仲丁基)-5,6,7,8-四氢喹啉);BOISAMBRENE FORTETM((乙氧基甲氧基)环十二烷);BOISIRISTM((1S,2R,5R)-2-乙氧基-2,6,6-三甲基-9-亚甲基二环[3.3.1]壬烷);乙酸龙脑酯(乙酸(2S,4S)-1,7,7-三甲基二环[2.2.1]庚-2-基酯);丁酰乳酸丁酯(丁酸1-丁氧基-1-氧代丙-2-基酯);对丁基环己基乙酸酯(乙酸4-(叔丁基)环己酯);石竹烯((Z)-4,11,11-三甲基-8-亚甲基二环[7.2.0]十一碳-4-烯);CASHMERANTM(1,1,2,3,3-五甲基-2,3,6,7-四氢-1H-茚-4(5H)-酮);CASSYRANETM(5-叔丁基-2-甲基-5-丙基-2H-呋喃);柠檬醛(CITRAL)((E)-3,7-二甲基辛-2,6-二烯醛);CITRALLEMAROMETM N((E)-3,7-二甲基辛-2,6-二烯醛);CITRATHALTM R((Z)-1,1-二乙氧基-3,7-二甲基辛-2,6-二烯);香茅醛(3,7-二甲基辛-6-烯醛);香茅醇(3,7-二甲基辛-6-烯-1-醇);乙酸香茅酯(乙酸3,7-二甲基辛-6-烯-1-基酯);甲酸香茅酯(甲酸3,7-二甲基辛-6-烯-1-基酯);香茅腈(3,7-二甲基辛-6-烯腈);丙酸香茅酯(丙酸3,7-二甲基辛-6-烯-1-基酯);爽腈(十二腈);花冠醇(4-环己基-2-甲基丁-2-醇);COSMONETM((Z)-3-甲基环十四碳-5-烯酮);兔耳草醛(3-(4-异丙基苯基)-2-甲基丙醛);环格蓬酯(2-(环己基氧基)乙酸烯丙酯);水杨酸环己酯(2-羟基苯甲酸环己酯);CYCLOMYRAL(8,8-二甲基-1,2,3,4,5,6,7,8-八氢萘-2-甲醛);突厥烯酮((E)-1-(2,6,6-三甲基环己-1,3-二烯-1-基)丁-2-烯-1-酮);甲位突厥酮((E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮);丁位突厥酮((E)-1-(2,6,6-三甲基环己-3-烯-1-基)丁-2-烯-1-酮);癸烯醛-4-反式((E)-癸-4-烯醛);2-戊基环戊酮(DELPHONE)(2-戊基环己酮);二氢茴香脑(丙二酸1-(1-(3,3-二甲基环己基)乙基)3-乙酯);二氢茉莉酮(3-甲基-2-戊基环戊-2-烯酮);二甲基苄基甲醇(2-甲基-1-苯基丙-2-醇);二甲基苄基甲基乙酸酯(乙酸2-甲基-1-苯基丙-2-基酯);二甲基苄基甲基丁酸酯(丁酸2-甲基-1-苯基丙-2-基酯);二甲基辛烯酮(4,7-二甲基辛-6-烯-3-酮);二甲基庚醇(2,6-二甲基庚-2-醇);DIPENTENE(1-甲基-4-(丙-1-烯-2-基)环己-1-烯);DUPICALTM((E)-4-((3aS,7aS)-六氢-1H-4,7-亚甲基茚-5(6H)-亚基)丁醛);EBANOLTM((E)-3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-4-烯-2-醇);己酸乙酯(己酸乙酯);辛酸乙酯(辛酸乙酯);乙基芳樟醇((E)-3,7-二甲基壬-1,6-二烯-3-醇);乙基芳樟基乙酸酯(乙酸(Z)-3,7-二甲基壬-1,6-二烯-3-基酯);庚酸乙酯(庚酸乙酯);藏红花酸乙酯(2,6,6-三甲基环己-1,3-二烯-1-甲酸乙酯);桉叶素((1s,4s)-1,3,3-三甲基-2-氧杂二环[2.2.2]辛烷);乙酸葑酯(乙酸(2S)-1,3,3-三甲基二环[2.2.1]庚-2-基酯);葑醇((1S,2R,4R)-1,3,3-三甲基二环[2.2.1]庚-2-醇);FIXOLIDETM(1-(3,5,5,6,8,8-六甲基-5,6,7,8-四氢萘-2-基)乙酮);FLORALOZONETM(3-(4-乙基苯基)-2,2-二甲基丙醛);花青醛(3-(3-异丙基苯基)丁醛);FLOROCYCLENETM(丙酸(3aR,6S,7aS)-3a,4,5,6,7,7a-六氢-1H-4,7-亚甲基茚-6-基酯);FLOROPALTM(2,4,6-三甲基-4-苯基-1,3-二噁烷);FRESKOMENTHETM(2-(仲丁基)环己酮);果糖酯((3aS,4S,7R,7aS)-八氢-1H-4,7-亚甲基茚-3a-甲酸乙基酯);果腈(2-甲基癸腈);格蓬酮(1-(3,3-二甲基环己-1-烯-1-基)戊-4-烯-1-酮);茴香酯(异丁酸(3aR,6S,7aS)-3a,4,5,6,7,7a-六氢-1H-4,7-亚甲基茚-6-基酯);香叶醇((E)-3,7-二甲基辛-2,6-二烯-1-醇);合成乙酸香叶酯(乙酸(E)-3,7-二甲基辛-2,6-二烯-1-基酯);异丁酸香叶酯(异丁酸(E)-3,7-二甲基辛-2,6-二烯-1-基酯);奇华酮(2-乙基-6,6-二甲基环己-2-烯甲酸乙酯);环十五烯内酯((E)-氧杂环十六碳-12-烯-2-酮);二氢茉莉酮酸甲酯(3-氧代-2-戊基环戊烷乙酸甲酯);HERBANATETM((2S)-3-异丙基二环[2.2.1]庚-5-烯-2-甲酸乙酯);丁酸顺式-3-己烯基酯(丁酸(Z)-己-3-烯-1-基酯);己基肉桂醛((E)-2-亚苄基辛醛);异丁酸己酯(异丁酸己酯);水杨酸己酯(2-羟基苯甲酸己酯);INDOFLORTM(4,4a,5,9b-四氢茚并[1,2-d][1,3]二噁英);乙位紫罗兰酮((E)-4-(2,6,6-三甲基环己-1-烯-1-基)丁-3-烯-2-酮);甲位紫罗兰酮((E)-4-(2,6,6-三甲基环己-2-烯-1-基)丁-3-烯-2-酮);甲位鸢尾酮((E)-4-(2,5,6,6-四甲基环己-2-烯-1-基)丁-3-烯-2-酮);龙涎酮(1-(2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);ISOCYCLOCITRAL(2,4,6-三甲基环己-3-烯甲醛);乙酸异壬酯(乙酸3,5,5-三甲基己酯);甲基-2-丁酸异丙酯(2-甲基丁酸异丙酯);ISORALDEINETM 70((E)-3-甲基-4-(2,6,6-三甲基环己-2-烯-1-基)丁-3-烯-2-酮);JASMACYCLENETM(乙酸(3aR,6S,7aS)-3a,4,5,6,7,7a-六氢-1H-4,7-亚甲基茚-6-基酯);顺式茉莉酮((Z)-3-甲基-2-(戊-2-烯-1-基)环戊-2-烯酮);KARANALTM(5-(仲丁基)-2-(2,4-二甲基环己-3-烯-1-基)-5-甲基-1,3-二噁烷);高芳烯((Z)-3,4,5,6,6-五甲基庚-3-烯-2-酮);叶醇缩醛((Z)-1-(1-乙氧基乙氧基)己-3-烯);LEMONILETM((2E,6Z)-3,7-二甲基壬-2,6-二烯腈);LIFFAROMETM GIV((Z)-己-3-烯-1-基甲基碳酸酯);LILIALTM(3-(4-(叔丁基)苯基)-2-甲基丙醛);芳樟醇(3,7-二甲基辛-1,6-二烯-3-醇);乙酸芳樟酯(乙酸3,7-二甲基辛-1,6-二烯-3-基酯);MAHONIALTM((4E)-9-羟基-5,9-二甲基-4-癸醛);异丁酸麦芽酚酯(异丁酸2-甲基-4-氧代-4H-吡喃-3-基酯);母菊酯(2-甲基戊酸乙酯);甜瓜醛(2,6-二甲基庚-5-烯醛);薄荷醇(2-异丙基-5-甲基环己醇);薄荷酮(2-异丙基-5-甲基环己酮);甲基柏木基酮(1-((1S,8aS)-1,4,4,6-四甲基-2,3,3a,4,5,8-六氢-1H-5,8a-亚甲基甘菊环-7-基)乙酮);甲基壬基酮(十一烷-2-酮);甲基辛炔碳酸酯(壬-2-炔酸甲酯);圆柚甲烷(6,6-二甲氧基-2,5,5-三甲基己-2-烯);柑青醛(4-(4-甲基戊-3-烯-1-基)环己-3-烯甲醛);仙酒酮(2-(2-(4-甲基环己-3-烯-1-基)丙基)环戊酮);NEOBERGAMATETM FORTE(乙酸2-甲基-6-亚甲基辛-7-烯-2-基酯);NEOFOLIONETM((E)-壬-2-烯酸甲酯);NEROLIDYLETM(乙酸(Z)-3,7,11-三甲基十二碳-1,6,10-三烯-3-基酯);乙酸橙花酯HC(乙酸(Z)-3,7-二甲基辛-2,6-二烯-1-基酯);诺纳多(6,8-二甲基壬-2-醇);壬烯醛-6-顺式((Z)-壬-6-烯醛);NYMPHEALTM(3-(4-异丁基-2-甲基苯基)丙醛);ORIVONETM(4-(叔戊基)环己酮);PARADISAMIDETM(2-乙基-N-甲基-N-(间甲苯基)丁酰胺);香叶吡喃(2-甲基-4-亚甲基-6-苯基四氢-2H-吡喃);PEONILETM(2-亚环己基-2-苯基乙腈);PETALIATM(2-亚环己基-2-(邻甲苯基)乙腈);PIVAROSETM(丙酸2,2-二甲基-2-苯基乙酯);PRECYCLEMONETM B(1-甲基-4-(4-甲基戊-3-烯-1-基)环己-3-烯甲醛);PYRALONETM(6-(仲丁基)喹啉);RADJANOLTM SUPER((E)-2-乙基-4-(2,2,3-三甲基环戊-3-烯-1-基)丁-2-烯-1-醇);覆盆子酮(N112)(4-(4-羟基苯基)丁-2-酮);RHUBAFURANETM(2,2,5-三甲基-5-戊基环戊酮);结晶玫瑰(乙酸2,2,2-三氯-1-苯基乙酯);9-癸烯醇(癸-9-烯-1-醇);ROSYFOLIA((1-甲基-2-(5-甲基己-4-烯-2-基)环丙基)-甲醇);ROSYRANETM SUPER(4-亚甲基-2-苯基四氢-2H-吡喃);SERENOLIDE(环丙烷甲酸2-(1-(3,3-二甲基环己基)乙氧基)-2-甲基丙酯);SILVIALTM(3-(4-异丁基苯基)-2-甲基丙醛);SPIROGALBANONETM(1-(螺[4.5]癸-6-烯-7-基)戊-4-烯-1-酮);STEMONETM((E)-5-甲基庚-3-酮肟);SUPER MUGUETTM((E)-6-乙基-3-甲基辛-6-烯-1-醇);SYLKOLIDETM(环丙烷甲酸(E)-2-((3,5-二甲基己-3-烯-2-基)氧基)-2-甲基丙酯);丙位松油烯(1-甲基-4-丙-2-基环己-1,4-二烯);松油烯(1-甲基-4-(丙-2-亚基)环己-1-烯);乙酸松油酯(乙酸2-(4-甲基环己-3-烯-1-基)丙-2-基酯);四氢芳樟醇(3,7-二甲基辛-3-醇);四氢月桂烯醇(2,6-二甲基辛-2-醇);西藏麝香(氧杂环十六烷-2-酮);十三烯-2-腈((E)-十三碳-2-烯腈);甲基癸烯醇((E)-4-甲基癸-3-烯-5-醇);VELOUTONETM(2,2,5-三甲基-5-戊基环戊酮);VIRIDINETM((2,2-二甲氧基乙基)苯);ZINARINETM(2-(2,4-二甲基环己基)吡啶);及其混合物。
可以根据本发明包封的香料成分的完整列表可以在香料文献中找到,例如“Perfume&Flavor Chemicals”,S.Arctander,AlluredPublishing,2000。
所述至少一种有益剂还可以是化妆品成分。优选地,所述化妆品成分具有经计算的辛醇/水分配系数(ClogP),其为1.5或更大、更优选3或更大。或者优选化妆品成分的ClogP为2至7。
特别有用的化妆品成分可以选自润肤剂、平滑活性剂、水化活性剂、平滑和舒缓活性剂、装饰活性剂、抗衰老活性剂、排水活性剂、重塑活性剂、皮肤平整活性剂、防腐剂、抗氧化活性剂、抗菌或抑菌活性剂、清洁活性剂、润滑活性剂、结构化活性剂、头发调理活性剂、美白活性剂、纹理化活性剂、软化活性剂、去头皮屑活性剂和去角质活性剂。
特别有用的化妆品成分包括、但不限于疏水性聚合物,例如烷基二甲基硅氧烷、聚甲基倍半硅氧烷(polymethyl silsesquioxane)、聚乙烯、聚异丁烯、苯乙烯-乙烯-苯乙烯和苯乙烯-丁烯-苯乙烯嵌段共聚物、矿物油例如氢化异链烷烃、聚硅氧烷、植物油例如摩洛哥坚果油(argan oil)、霍霍巴油(jojoba oil)、芦荟油、脂肪酸和脂肪醇及其酯、糖脂、磷脂、鞘脂例如神经酰胺、固醇和类固醇、萜烯、倍半萜、三萜及其衍生物、精油例如山金车油(Arnica oil)、蒿油(Artemisia oil)、树皮油(Bark tree oil)、桦树叶油、金盏花油(Calendula oil)、桂皮油、紫锥花油(Echinacea oil)、桉叶油、人参油、枣油、向日葵油(Helianthus oil)、茉莉油、熏衣草油、莲子油、紫苏油、迷迭香油、檀香油、茶树油、百里香油、缬草油、苦艾油、依兰依兰油,丝兰油(Yucca oil)。
本发明的芯-壳微胶囊通常具有1至100μm,优选5至50μm,甚至更优选10至20μm的体积平均尺寸(d50)。可以通过光散射测量,根据本领域技术人员已知的方法得到分散颗粒例如微胶囊的体积平均尺寸。
本发明的另一个方面涉及制备包封的组合物,特别是如上文所述的包封的组合物的方法。该方法包括下列步骤:
a)提供芯组合物,所述芯组合物包含:至少一种三官能异氰酸酯,和至少一种有益剂,所述芯组合物任选地包含水可分散性多异氰酸酯;
b)将所述芯组合物与水混合并任选地与阳离子共聚物混合;
c)将b)中得到的混合物乳化以得到体积平均尺寸为1至100μm,优选5至50μm,甚至更优选10至20μm的芯组合物液滴;
d)添加至少一种不是脱乙酰壳多糖的多官能胺,优选同时将c)中得到的混合物在搅拌下保持;
e)将d)中得到的混合物逐步加热至60至95℃,优选80至90℃的温度,优选历时2小时至4小时,例如3±0.5小时;
f)将脱乙酰壳多糖添加到步骤e)中得到的混合物中,并优选将该混合物维持在步骤e)中采用的温度下,特别是历时1至5小时,例如2±0.5小时或4.5±0.5小时;
g)让f)中得到的混合物冷却至室温,以得到微胶囊的浆液。
步骤a)中使用的三官能异氰酸酯的重量相对于步骤a)中提供的芯组合物的重量为8至20wt.-%,优选9至16wt.-%,更优选10至12wt.-%。
水包油型乳液具有提供多个液滴的优点,这些液滴可用作壳形成的模板,其中所述壳包围这些液滴中的每一个构建。此外,可以通过控制乳化条件(例如搅拌速度和搅拌器几何形状)来控制乳液中的液滴尺寸分布。作为结果,得到了具有受控平均尺寸和尺寸分布的多个微胶囊,其中油相被包封且由此形成微胶囊的芯。在本发明的一个具体实施方案中,让步骤b)中形成的混合物在不搅拌下静置,直至芯组合物和水相分离。
步骤a)中任选地使用的水可分散性多异氰酸酯的重量相对于步骤a)中提供的芯组合物的重量可以为0.1至20wt.-%,优选0.5至10wt.-%,更优选1至5wt.-%。在步骤d)中使用的所述至少一种不是脱乙酰壳多糖的多官能胺的重量相对于在步骤f)中得到的混合物的重量可以为0.1至2wt.-%,优选为0.25至1wt.-%,更优选为0.4至0.8wt.-%。
步骤b)中任选地使用的阳离子共聚物的重量相对于步骤f)中得到的混合物的重量可以为2至10wt.-%,优选为2.5至7.5wt.-%,更优选为3至5wt.-%。
在步骤f)中使用的脱乙酰壳多糖的重量相对于在步骤f)中得到的混合物的重量可以为0.06至0.3wt.-%,优选为0.12至0.24wt.-%,更优选为0.18至0.21wt.-%。
可以选择适合的搅拌速度和混合器的几何形状以得到期望的平均液滴尺寸和液滴尺寸分布。在本发明的方法中,可以使用配备有涡轮机或具有斜梁的横梁搅拌器(例如Mig搅拌器)并且具有搅拌器直径与反应器直径之比为0.6至0.8的一升容器。可以在约100至约1200rpm,更特别是约600至1000rpm的搅拌速度下,在具有体积平均尺寸(d50)为30微米或更小,更特别是20微米或更小的这种反应器中形成微胶囊。优选地,使用Mig搅拌器以850+/-50rpm的速度运行。然而,本领域技术人员易于理解,这类搅拌条件可一根据反应器的大小和批量大小,搅拌器的精确几何形状,搅拌器的直径与反应器的直径之比的不同而改变。例如,对于具有搅拌器与反应器直径比为0.5至0.9且浆液体积为0.5至8吨的Mig搅拌器,本发明上下文中优选的搅拌速度为150rpm至50rpm。
在形成微胶囊之后,通常让包封的组合物冷却至室温(参见上述步骤g))。在冷却之前,期间或之后,可以进一步加工包封的组合物。进一步的加工可以包括用抗微生物防腐剂处理组合物,所述防腐剂在本领域中是众所周知的。进一步加工还可以包括添加助悬剂,例如水胶体助悬剂,以有助于微胶囊的稳定物理分散并防止任何乳状化或聚结。优选的助悬剂为羟乙基纤维素,例如Natrosol 250HX(ex Ashland)。在进一步加工过程中也可以添加本领域常规的任何另外的佐剂。
本发明的另一个方面涉及可通过上文所述的方法得到的包封的组合物。
本发明的又一个方面涉及如上文所述的包封的组合物在增强消费品中有益剂的性能中的用途。
本发明还涉及包含如上文所述的包封的组合物的消费品。所述消费品优选为护发产品,特别是选自洗发香波和头发调理剂。但是,另一方面,所述消费品也可以是其他种类的个人护理产品,例如肥皂,沐浴露,沐浴凝胶或护肤品。
如本文所用,“化妆品”是指旨在以销售形式使用或消费而不是用于随后的商业制造或改性的制品。
本发明的包封的组合物在用作消费品中的香料递送载体时特别有用,所述消费品需要微胶囊很好地粘附到它们所施加的基质上,以提供最佳的香味益处。这种消费品尤其包括洗发香波和头发调理剂,而且还包括纺织品处理产品,例如洗衣洗涤剂和调理剂。
本发明的消费品可以包含0.01至5wt.-%,优选0.05至2.5wt.-%,更优选0.1至1wt.-%的本文所述的微胶囊,以消费品的总重为基准。
本发明的消费品可以包含0.00001至0.005wt.-%,更特别地0.00005至0.001wt.-%,仍然更特别地0.00008至0.0005wt.-%的游离脱乙酰壳多糖,以消费品的总重为基准。
本公开还涉及用于增强消费品中有益剂的性能的方法,所述方法通过添加本发明的包封的组合物来进行。
本发明的具体特征和进一步的优点从以下实施例变得显而易见。
实施例1-本发明聚脲微胶囊的制备
在实施例1.1中,通过进行下列步骤得到微胶囊:
-通过在配备搅拌器的反应器中混合1g Bayhydur XP 2547(ex Covestro),4gTakenate D110N(ex Mitsui)和30g香料组合物(ex Givaudan)制备芯组合物;
-将该芯组合物以600rpm搅拌10分钟;
-向该芯组合物中添加40g水,然后添加根据WO2016/207187A1(实施例1)制备的3g聚(甲基丙烯酰氨基丙基三甲基氯化铵-共-丙烯酸),其具有71mol-%的甲基丙烯酰氨基丙基三甲基氯化铵和29mol-%的丙烯酸;
-将得到的混合物以1100rpm搅拌30分钟,以便得到具有10±2μm的体积平均芯组合物液滴尺寸(d50)的乳液;
-添加0.6g Lupasol G100,(ex BASF);
-以0.3℃/min的速率加热该混合物;
-120分钟后,添加0.2g具有200’000g/mol的平均分子量的脱乙酰壳多糖(来自虾,ex Acros),0.4g 30vol.-%乙酸水溶液和10g水的混合物;
-一旦温度达到85℃,则将该混合物在该温度下再保持120分钟;
-添加4g 20%的氨水溶液,并且将该混合物再保持35分钟;
-让得到的混合物在60分钟内冷却至25℃,以便得到微胶囊的浆液。
通过使用在120℃下操作的热天平测量浆液的固体含量。在干燥引起的重量变化率下降到低于0.1%/min的点处取得的以沉积在天平上的初始浆液的重量百分比表示的固体含量。将测量的固体含量与基于所涉及的香料和包封材料的重量计算之比视为包封收率的测量值,以wt.-%表示。
得到的浆液的固体含量为37wt.-%,胶囊的体积平均尺寸(d50)为10±1μm,且包封效率为100%。
在实施例1.1中,相对于提供的芯组合物的重量使用的三官能异氰酸酯的重量为11wt.-%(三官能异氰酸酯与香料的重量比:0.13)。
在实施例1.2中,通过使用与实施例1.1中相同的方法得到微胶囊,但相对于提供的芯组合物的重量使用的三官能异氰酸酯的重量为14wt.-%(三官能异氰酸酯与香料的重量比:0.17)。
在实施例1.3中,通过使用与实施例1.1中相同的方法得到微胶囊,但相对于提供的芯组合物的重量使用的三官能异氰酸酯的重量为19wt.-%(三官能异氰酸酯与香料的重量比:0.25)。
在实施例1.4中,通过使用与实施例1.1中相同的方法得到微胶囊,但使用具有的分子量为85’000g/mol的蘑菇脱乙酰壳多糖(ex Kionutrime)。
在实施例1.5中,通过使用与实施例1.1中相同的方法得到微胶囊,但使用具有的分子量为15’000g/mol的蘑菇脱乙酰壳多糖(ex Kionutrime)。
表1:多异氰酸酯和脱乙酰壳多糖类型的变化
实施例2-对比例
通过实施实施例1.1中所述的方法已经得到了一系列微胶囊,其中TakenateD110N与香料油的重量比和脱乙酰壳多糖与香料油的重量比根据表2变化。
在实施例2.1和2.2中,用Desmodur W(双(4-环己基异氰酸亚甲酯))替代TakenateD110N。
表2:多异氰酸酯和脱乙酰壳多糖量的变化
参比样品2.1和2.2在储存期间不稳定,其中洗发香波基质中有100%的香料渗漏。
实施例3-嗅觉性能的比较
由4名专家组成的小组评估微胶囊的嗅觉性能,他们以1至5的等级评定气味强度(1=几乎察觉不到,2=微弱,3=中等,4=强烈和5=非常强烈)。
评估在未加香的洗发香波和未加香的头发调理剂中的样品。在用桨式混合器适度搅拌下将上述浆液添加到这些基料中,使得浆料的水平为0.6wt.-%,以每种基料的总重为基准。
在洗发香波的情况下,将基于头发样本总重20wt.-%的洗发香波施加到在先用相同重量的水润湿的样本上。每个样本的干重为约12g。
在头发调理剂的情况下,将样本预先用未加香的洗发香波洗涤并用水冲洗。然后,在用洗发香波洗涤后即刻施用基于样本总重10wt.-%的调理剂。
对于洗发香波和头发调理剂,样本均经过按摩20秒,然后在37℃的自来水下以3.2l/min的流速冲洗30秒,不用手接触样本。为了进行该评估,谨慎处理样本,以尽量减少机械破坏微胶囊的风险。在室温下干燥样本24h(冷空气干燥)后,进行摩擦前和摩擦后的嗅觉评估。该评估通过适度梳理每个样本的一部分进行5次。
对于牵涉吹风机(热头发干燥)的评估,将头发样本在空气中放置15分钟。然后将内部温度为180℃下操作并提供0.016m3/s体积空气流速的标准吹风机放置在距离头发样本5cm处,并且施加气流5分钟,同时在这5分钟期间使气流在样本上下移动。头发上的温度为约40至45℃。
结果如表3和表4中所示。
表3:对头发样本的嗅觉性能-洗发香波情况
表4:新鲜制备和老化的微胶囊的头发样本的嗅觉性能-头发调理剂情况
这些结果表明,将Takenate D110N与脱乙酰壳多糖组合对保持微胶囊在用吹风机吹干头发后的性能有积极影响,即使在洗发香波和头发调理剂基质中储存后也是如此。
Claims (20)
1.包封的组合物,包含至少一种芯-壳微胶囊,其中所述至少一种芯-壳微胶囊包含芯和包围所述芯的壳,所述芯包含至少一种有益剂,其中所述壳包含通过至少一种三官能异氰酸酯与至少一种不是脱乙酰壳多糖的多官能胺的反应形成的聚脲树脂,其中所述至少一种三官能异氰酸酯为脂族三元醇与至少一种芳脂族二异氰酸酯的加合物,其中衍生自所述三官能异氰酸酯的聚脲树脂部分与所述芯之间的重量比为0.09至0.30,优选0.10至0.20,更优选0.11至0.18,且其中所述壳还包含脱乙酰壳多糖。
2.根据权利要求1的组合物,其中所述脂族三元醇选自2-乙基丙-1,2,3-三醇和2-乙基-2-(羟基甲基)丙-1,3-二醇,优选2-乙基丙-1,2,3-三醇。
3.根据权利要求1或2之一的组合物,其中所述至少一种芳脂族二异氰酸酯选自1,2-双(异氰酸基甲基)苯,1,3-双(异氰酸基甲基)苯,1,4-双(异氰酸基甲基)苯,1-异氰酸基-2-(异氰酸基甲基)苯,1-异氰酸基-3-(异氰酸基甲基)苯和1-异氰酸基-4-(异氰酸基甲基)苯。
4.根据权利要求1的组合物,其中所述至少一种三官能异氰酸酯为2-乙基丙-1,2,3-三醇和1,3-双(异氰酸基甲基)苯的加合物。
5.根据权利要求1至4之一的组合物,其中所述脱乙酰壳多糖沉积在包围所述芯的壳的外表面上和/或所述脱乙酰壳多糖包埋在包围所述芯的壳中。
6.根据权利要求5之一的组合物,还包含游离脱乙酰壳多糖。
7.根据权利要求1至4之一的组合物,其中所述聚脲树脂通过所述至少一种三官能异氰酸酯与所述至少一种不是脱乙酰壳多糖的多官能胺以及与脱乙酰壳多糖的反应形成。
8.根据权利要求1至7之一的组合物,其中所述聚脲树脂通过所述至少一种三官能异氰酸酯和水可分散性多异氰酸酯与所述至少一种不是脱乙酰壳多糖的多官能胺以及任选地与脱乙酰壳多糖的反应形成。
9.根据权利要求1至8之一的组合物,其中所述水可分散性多异氰酸酯为基于六亚甲基二异氰酸酯的水可分散性多异氰酸酯。
10.根据权利要求1至9之一的组合物,其中所述不是脱乙酰壳多糖的多官能胺为聚(乙烯亚胺)。
11.根据权利要求1至10之一的组合物,其中所述壳还包含阳离子聚合物。
12.根据权利要求1至11之一的组合物,其中所述脱乙酰壳多糖和/或衍生自所述脱乙酰壳多糖的聚脲树脂部分与所述芯之间的重量比为0.002至0.01,优选0.004至0.008,更优选0.006至0.007。
13.根据权利要求1至12之一的组合物,其中所述脱乙酰壳多糖具有5’000至1’000’000g/mol,优选7’500至500’000g/mol,仍然更优选10’000至250’000g/mol的平均分子量。
14.根据权利要求1至13之一的组合物,其中所述脱乙酰壳多糖具有高于60%,更特别地高于70%,仍然更特别地高于80%的平均脱乙酰度。
15.根据权利要求1至14之一的组合物,其中所述有益剂选自至少一种香料成分和至少一种化妆品成分。
16.用于制备包封的组合物,特别是权利要求1至15之一的包封的组合物的方法,该方法包括下列步骤:
a)提供芯组合物,所述芯组合物包含:至少一种三官能异氰酸酯,和至少一种有益剂,所述芯组合物任选地包含水可分散性多异氰酸酯;
b)将所述芯组合物与水混合并任选地与阳离子共聚物混合;
c)将b)中得到的混合物乳化以得到体积平均尺寸为1至100μm,优选5至50μm,甚至更优选10至20μm的芯组合物液滴;
d)添加至少一种不是脱乙酰壳多糖的多官能胺,优选同时将c)中得到的混合物在搅拌下保持;
e)将d)中得到的混合物逐步加热至60至95℃,优选80至90℃的温度,优选历时2小时至4小时,例如3±0.5小时;
f)将脱乙酰壳多糖添加到步骤e)中得到的混合物中,并优选将该混合物维持在步骤e)中采用的温度下,特别是历时1至5小时,例如2±0.5小时或4.5±0.5小时;
g)让f)中得到的混合物冷却至室温,以得到微胶囊的浆液,
其中步骤a)中使用的三官能异氰酸酯的重量相对于步骤a)中提供的芯组合物的重量为8至20wt.-%,优选9至16wt.-%,更优选10至12wt.-%。
17.根据步骤16的方法,其中让步骤b)中形成的混合物在不搅拌下静置,直至芯组合物和水相分离。
18.包封的组合物,其可通过根据权利要求16或17之一的方法得到。
19.根据权利要求1至15或18之一的包封的组合物在增强消费品中有益剂的性能中的用途。
20.消费品,包含根据权利要求1至15或18之一的包封的组合物,其中该消费品优选为护发产品,特别地选自洗发香波和头发调理剂。
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GB202018435D0 (en) * | 2020-11-24 | 2021-01-06 | Givaudan Sa | Improvements in or relating to organic compounds |
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EP4021629A1 (en) | 2022-07-06 |
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