CN114340594A - 聚氨酯凝胶 - Google Patents
聚氨酯凝胶 Download PDFInfo
- Publication number
- CN114340594A CN114340594A CN202080061942.4A CN202080061942A CN114340594A CN 114340594 A CN114340594 A CN 114340594A CN 202080061942 A CN202080061942 A CN 202080061942A CN 114340594 A CN114340594 A CN 114340594A
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- Prior art keywords
- gel
- polyurethane elastomer
- carrier fluid
- gel composition
- extract
- Prior art date
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Abstract
本发明涉及包含聚氨酯弹性体的凝胶组合物。所述聚氨酯弹性体由多元醇、多异氰酸酯和任选的聚氨酯反应催化剂任选地在外用可接受的载体流体的存在下反应而形成。在一些实施方案中,所述凝胶组合物包含个人活性成分或保健活性成分,其能够经由预加载方法或后加载方法掺入所述凝胶组合物中。本文还提供了包含所述聚氨酯弹性体的凝胶糊状物和外用制剂,及其制备方法。
Description
技术领域
本发明涉及包含聚氨酯弹性体的凝胶组合物。
背景技术
弹性体凝胶由悬浮在润肤剂中的交联三维聚合物网络组成。弹性体凝胶能够在润肤剂中溶胀,并且可用作化妆品配方中的油相增稠剂。这些弹性体凝胶在皮肤上具有滚珠般的感觉,并且提供增强的美感和感觉。这些期望的属性不能用传统的油凝胶或线性聚合物来实现,使得弹性体凝胶成为独特的化妆品施用载体。
有机硅弹性体凝胶由于其增稠和胶凝效率以及独特的丝滑和粉状感觉特征而被广泛用于个人护理产品中的成分。当掺入配方中时,它们提供光滑、干爽和非油腻的感觉。有机硅弹性体与有机硅基流体相容。最近,对个人护理产品中有机硅基成分的负面环境影响提出了担忧。有机硅耐氧化和化学侵蚀,因此不可生物降解。此外,有机硅源自化石燃料,并且不被认为是可再生资源。随着消费者越来越了解化妆品对环境的影响,对不含有机硅的可生物降解且可再生来源的成分的需求迅速增加。
衍生自生物质的有机硅替代品已经开始进入个人护理市场以满足这些需求。然而,这些线性聚合物和润肤剂并未提供弹性体凝胶所提供的独特美感。因此,需要具有有利的环境特征的不含有机硅的弹性体凝胶。
本发明由不含有机硅且由>99%生物基材料组成的聚氨酯弹性体凝胶组成。聚氨酯弹性体凝胶提供了有机硅基弹性体的美学益处,同时满足了对不含有机硅的可再生资源材料的市场需求。
本发明进一步涉及一种用于制备所述聚氨酯弹性体凝胶的方法。在生物基润肤剂或生物基润肤剂混合物的反应介质中在升高的温度下使用聚氨酯催化剂使生物基多元醇与生物基多异氰酸酯反应,以得到聚氨酯弹性体橡胶。然后向橡胶中添加生物基润肤剂,并且将混合物加工成聚氨酯弹性体凝胶。
发明内容
在一些实施方案中,本发明提供了一种包含聚氨酯弹性体的凝胶组合物,所述聚氨酯弹性体不需要纯化并且在外用可接受的溶剂中由以下物质的反应形成:A)多元醇;B)多异氰酸酯;C)任选的聚氨酯反应催化剂;和D)外用可接受的载体流体。
在实施方案中,通过在聚氨酯弹性体凝胶形成期间将个人护理或保健活性成分(E)溶解在所述外用可接受的载体流体中(预加载方法)或将其与形成的聚氨酯弹性体凝胶混合(后加载方法),将其掺入所述聚氨酯弹性体凝胶中。
在进一步的实施方案中,本发明进一步提供了一种具有以下通用结构的交联聚氨酯弹性体网络:
其中:n为2至10000000;A是选自氢、异氰酸酯和羟基的端基;R1是C1-C60取代或未取代的直链或支链脂族基团、脂环族基团、芳基、杂脂环族基团或杂芳基,任选地包含杂原子;R2是C1-C60取代或未取代的直链或支链脂族基团、脂环族基团、芳基、杂脂环族基团或杂芳基,任选地包含杂原子;并且B是选自异氰酸酯和羟基的端基。
在一些实施方案中,本发明提供了一种根据以下通用反应方案的交联聚氨酯弹性体网络:
其中R是具有两个或更多个官能团的多元醇,并且其中R1是具有三个或更多个官能团的异氰酸酯,并且所述润肤剂是外用可接受的。
在进一步的实施方案中,本发明提供了一种根据以下通用反应方案的交联聚氨酯弹性体网络:
其中R是具有三个或更多个官能团的多元醇,并且其中R1是具有两个或更多个官能团的异氰酸酯,并且所述润肤剂是外用可接受的。
在进一步的实施方案中,本发明提供了一种根据以下通用反应方案的交联聚氨酯弹性体网络:
其中所述润肤剂是外用可接受的。
在仍进一步的实施方案中,本发明提供了一种用于制备聚氨酯弹性体凝胶的方法,所述方法包括:向容器中添加化妆品可接受的润肤剂、多元醇和多异氰酸酯;在室温下搅拌所述混合物,直至获得澄清、均匀的溶液;在搅拌下添加聚氨酯催化剂,并且将所述反应加热至约60℃持续约23小时,此时形成软橡胶;允许所述橡胶冷却至室温,并且添加化妆品可接受的润肤剂并将所述混合物加工成光滑的凝胶。
在实施方案中,在室温下形成所述橡胶。在实施方案中,所述多元醇、所述多异氰酸酯和所述润肤剂是生物基的。在实施方案中,所述多元醇、所述多异氰酸酯和所述润肤剂不是生物基的。在实施方案中,使用铋、锡、锌或胺异氰酸盐催化剂。在实施方案中,基于生物基多元醇、生物基异氰酸酯、铋催化剂和生物基润肤剂或生物基润肤剂混合物的总组合重量,生物基润肤剂的浓度在70-85重量%之间。在实施方案中,所述多元醇具有范围从约500-10,000的分子量。在实施方案中,每个多元醇的OH单元数为约2-20。在实施方案中,每个多元醇的NCO单元数为约2-6。在实施方案中,所述生物基润肤剂选自酯、烃、碳酸酯、植物油或改性植物油。在实施方案中,所述生物基润肤剂具有在500-2500之间的扩散值(mm2/10min)。在实施方案中,所述生物基润肤剂具有240-1200的平均分子量。
在一些实施方案中,本发明提供了一种用于制备聚氨酯弹性体凝胶的方法,所述方法包括:向反应釜中添加三庚酸甘油酯、椰油辛酸酯/癸酸酯、二亚油酸/丙二醇共聚物和1,5-五亚甲基二异氰酸酯基多异氰酸酯;在室温下搅拌所述混合物,直至获得澄清、均匀的溶液;在搅拌下添加新癸酸铋,并且将所述反应加热至60℃,此时形成无色橡胶。
在进一步的实施方案中,本发明提供了一种用于制备聚氨酯弹性体凝胶的方法,所述方法包括:将聚氨酯弹性体橡胶置于鼓中,添加三庚酸甘油酯,用Cowles混合器研磨所述混合物;使所得悬浮液通过分散器,并且允许所得凝胶冷却至室温;以及在混合下添加十一烷和/或十三烷,直至达到所需的粘度。
在实施方案中,在室温下在24小时内在不搅拌下形成所述橡胶。在实施方案中,可以添加含有醇或胺的整理剂以淬灭未反应的异氰酸酯基团。在实施方案中,所述聚氨酯弹性体橡胶具有如本文所述的硬度。在实施方案中,所述聚氨酯弹性体凝胶具有如本文所述的粘度。
在一些实施方案中,本发明提供了一种包含聚氨酯弹性体的凝胶组合物,所述聚氨酯弹性体来自以下物质的反应:A)蓖麻油;B)异佛尔酮二异氰酸酯,其中异氰酸酯基团与羟基的摩尔比在1:1与1:2之间;C)任选的聚氨酯反应催化剂;和D)载体流体,其是化妆品可接受的(此类载体流体的例子包括琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯、椰油辛酸酯/癸酸酯、三庚酸甘油酯、C13-15烷烃、角鲨烯、十一烷、十三烷),其中溶剂浓度在60%(w/w)与99.9%(w/w)之间;其中可以通过在聚氨酯弹性体凝胶形成期间将个人护理或保健活性成分溶解在所述外用可接受的溶剂中(预加载方法)或将其与形成的聚氨酯弹性体凝胶混合(后加载方法),将其掺入所述聚氨酯弹性体凝胶中。
在实施方案中,所述聚氨酯催化剂是含铋基团的催化剂。在实施方案中,所述外用可接受的溶剂的碳含量>50%衍生自植物来源。
在进一步的实施方案中,本发明提供了一种用于制备所述聚氨酯弹性体凝胶的方法,所述方法包括:I)在D)外用可接受的载体流体的存在下,使A)蓖麻油;B)异佛尔酮二异氰酸酯;和(C)任选的聚氨酯反应催化剂反应。在仍进一步的实施方案中,本发明提供了一种根据本文的方法制备的凝胶组合物。
在又进一步的实施方案中,本发明提供了一种用于制备凝胶糊状物组合物的方法,所述方法包括:I)剪切本文的聚氨酯弹性体凝胶;以及II)将所剪切的聚氨酯弹性体凝胶与另外量的载体流体组合以形成凝胶糊状物组合物。
在又进一步的实施方案中,本发明提供了一种用于制备凝胶糊状物组合物的方法,所述方法包括:I)剪切本文的聚氨酯弹性体凝胶;以及II)将所剪切的聚氨酯弹性体凝胶与活性成分组合。
附图说明
图1显示了描述本文实施方案中所述的生物弹性体与常见载体流体的相容性的表格。
图2显示了如本文实施方案中所述的二亚油酸/丙二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图3显示了如本文实施方案中所述的二亚油酸/丙二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图4显示了如本文实施方案中所述的蓖麻油基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图5显示了如本文实施方案中所述的蓖麻油基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图6显示了如本文实施方案中所述的二亚油酸/二亚油酸二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图7显示了如本文实施方案中所述的二亚油酸/二亚油酸二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图。
图8显示了如本文实施方案中所述的蓖麻油基异佛尔酮二异氰酸酯三聚体弹性体的FTIR光谱图。
具体实施方式
定义
如本文所用,“一个/一种(a)”或“一个/一种(an)”可以意指一个或多个/一种或多种。如本文所用,当与词语“包含”结合使用时,词语“一个/一种(a)”或“一个/一种(an)”可以意指一个或多于一个/一种或多于一种。如本文所用,“另一个/另一种”或“一个进一步的/一种进一步的”可以意指至少第二个或更多个/至少第二种或更多种。
如本文所用的术语“约”意指大约±10%。当术语“约”结合数值或范围使用时,其通过扩展所述数值上下的边界来修饰该值或范围。通常,术语“约”在本文中用于向上或向下(更高或更低)以10%的差异修饰高于和低于所述值的数值,即±10%,除非指出不同的差异(例如,±30%、±20%、±5%、±1%等)。
在权利要求中使用术语“或”用于意指“和/或”,除非明确指出仅指代替代方案或替代方案是相互排斥的,尽管本公开文本支持仅指代替代方案和“和/或”的定义。
如本文所用,术语“包含(comprising)”(和包含(comprising)的任何变体或形式,诸如“包含(comprise)”和“包含(comprises)”)、“具有(having)”(和具有(having)的任何变体或形式,诸如“具有(have)”和“具有(has)”)、“包括(including)”(和包括(including)的任何变体或形式,诸如“包括(includes)”和“包括(include)”)或“含有(containing)”(和含有(containing)的任何变体或形式,诸如“含有(contains)”和“含有(contain)”)是包含性的或开放式的,并不排除另外的未列举的要素或方法步骤。可以设想,本说明书中讨论的任何实施方案均可以相对于本公开文本的任何方法和/或组合物来实施。
使用术语“例如(for example)”及其相应的缩写“例如(e.g.)”(无论是否斜体)意指所列举的具体术语是本公开文本的代表性例子和实施方案,其不旨在限于所引用或引述的具体例子,除非另外明确说明。
如本文所用,“在...与...之间”是包括范围端点的范围。例如,在x与y之间的数字明确包括数字x和y以及落在x和y内的任何数字。
如本文所用,术语“聚氨酯”表示通过使多元醇与异氰酸酯在适当催化剂存在下反应形成的材料。
术语“多元醇”是指具有含有活性氢原子的官能团的材料,所述活性氢原子可以与异氰酸酯反应。优选地,多元醇每个分子含有至少两个羟基、胺、羧酸和/或硫醇基团。
术语“多异氰酸酯”是指含有两个或更多个异氰酸酯官能团的物质。
术语“生物基的(bio-based)”是指主要由衍生自活物质的物质(也称为生物质)组成的材料。
术语“聚氨酯弹性体橡胶”是指多元醇、异氰酸酯和聚氨酯催化剂在润肤剂介质中的反应产物。
术语“聚氨酯弹性体凝胶”是指经加工的聚氨酯弹性体橡胶的产物。
本发明进一步涉及聚氨酯弹性体凝胶,其由在生物基外用可接受的载体流体或生物基外用可接受的载体流体混合物中与生物基多异氰酸酯交联的生物基多元醇组成。在一些实施方案中,反应由外用可接受的铋聚氨酯催化剂催化。本文所述的聚氨酯弹性体凝胶与化妆品和天然油具有良好的相容性,并且可以用作这些油的增稠剂。聚氨酯弹性体凝胶进一步提供了光滑、不粘、不油腻、保湿的皮肤感觉,同时延长化妆品配方的使用时间。聚氨酯弹性体凝胶的极性允许其掺入极性化妆品配方介质中。通常用于许多配方中的有机硅弹性体凝胶是非极性的,并且通常与极性配方介质不相容,因此聚氨酯弹性体凝胶满足了个人护理行业中的关键需求。
通过使用生物基多元醇、生物基多异氰酸酯和生物基载体流体,产生了包含>99%生物基材料的聚氨酯弹性体凝胶。有机硅弹性体凝胶衍生自不是可再生资源的化石燃料。通常认为衍生自生物质的化妆品成分被认为是“天然的”,并且对天然化妆品的市场需求推动了对不含有机硅的生物基弹性体的行业需求。
本发明涉及包含聚氨酯弹性体的凝胶组合物,所述聚氨酯弹性体不需要纯化并且在外用可接受的溶剂中由以下物质的反应形成:组分(A)多异氰酸酯;组分(B)多元醇;组分(C)任选的聚氨酯反应催化剂;任选地在组分(D)外用可接受的载体流体中。
组分(A)-多异氰酸酯
在一些实施方案中,组分(A)具有含有多于一个异氰酸酯的分子结构,并且可以通过多种方法由多胺或由多异氰酸酯的聚合制备,并且在其分子结构中应当具有两个或更多个反应性异氰酸酯官能团。在一些实施方案中,多异氰酸酯包含三个异氰酸酯官能团。多异氰酸酯在反应中充当交联剂,其允许使用双官能多元醇共聚物以产生三维聚合物网络。
多异氰酸酯的一个优选例子是六亚甲基二异氰酸酯三聚体,并且具有以下结构:
多异氰酸酯的另一个优选例子是五亚甲基二异氰酸酯三聚体,并且具有以下结构:
多异氰酸酯的另一个优选例子是六亚甲基二异氰酸酯,并且具有以下结构:
多异氰酸酯的另一个优选例子是五亚甲基二异氰酸酯,并且具有以下结构:
多异氰酸酯的另一个优选例子是异佛尔酮二异氰酸酯,并且具有以下结构:
多异氰酸酯的另一个优选例子是4,4'-亚甲基双(苯基异氰酸酯),并且具有以下结构:
多异氰酸酯的另一个优选例子是甲苯二异氰酸酯,并且具有以下结构:
多异氰酸酯的另一个优选例子是六亚甲基二异氰酸酯缩二脲。
含有两个异氰酸酯基团的多异氰酸酯的进一步的非限制性例子包括双(异氰酸基甲基)苯;1,3-双(异氰酸基甲基)环己烷;二苯甲烷二异氰酸酯;六亚甲基二异氰酸酯;六亚甲基二异氰酸酯基多异氰酸酯;1,5-五亚甲基二异氰酸酯;异氰酸基甲基乙基苯;异佛尔酮二异氰酸酯;亚甲基双(4-环己基异氰酸酯);间四亚甲基二异氰酸酯;间四亚甲基二甲苯二异氰酸酯;饱和亚甲基二苯基二异氰酸酯;和甲苯二异氰酸酯。
组分(B)-多元醇
在一些实施方案中,组分(B)具有含有多于一个可与异氰酸酯反应的羟基的分子结构。在某些实施方案中,组分(B)含有除羟基以外的亲核基团,并且术语“多元醇”是指具有可与异氰酸酯反应的活性氢的材料。优选地,多元醇每个分子含有至少两个羟基、胺、羧酸和/或硫醇基团。
当使用含有三个或更多个官能团的多元醇时,双官能异氰酸酯(例如,含有两个异氰酸酯官能团)可以用于合成聚氨酯弹性体凝胶。本文提供了示例性双官能异氰酸酯,并且其包括双(异氰酸基甲基)苯;1,3-双(异氰酸基甲基)环己烷;二苯甲烷二异氰酸酯;六亚甲基二异氰酸酯;六亚甲基二异氰酸酯基多异氰酸酯;1,5-五亚甲基二异氰酸酯;异氰酸基甲基乙基苯;异佛尔酮二异氰酸酯;亚甲基双(4-环己基异氰酸酯);间四亚甲基二异氰酸酯;间四亚甲基二甲苯二异氰酸酯;饱和亚甲基二苯基二异氰酸酯;甲苯二异氰酸酯。
多元醇的一个优选例子是蓖麻油,其天然含有多个羟基并且是生物基的。天然蓖麻油的分子结构是具有三条侧碳链的甘油三酯。通常,每个碳在9、10位处具有双键,并且在第12个碳上具有羟基。蓖麻油本质上具有大约160-165的羟值与大约89%C18OH和9%C18的脂肪酸分布。因此,并非天然的或未处理的蓖麻油中的所有碳链长度均含有OH基团,并且平均而言,仅约90%的所述链含有OH基团。蓖麻油的主要组分是甘油三蓖麻油酸酯,并且具有以下结构:
多元醇的另一个优选例子是二亚油酸/二亚油酸二醇共聚物,并且据报道具有以下结构:
多元醇的另一个优选例子是二亚油酸/丙二醇共聚物(也称为“二亚油酸/丙二醇共聚物”),并且据报道具有以下结构:
二亚油酸/丙二醇共聚物是100%生物基的,具有成膜特性,不粘,并且与化妆品和天然油具有良好的相容性。优选地,二亚油酸/丙二醇共聚物应当以羟基封端并且具有低酸值,因为羟基比羧酸更容易与异氰酸酯反应。二亚油酸/丙二醇共聚物的分子量可以在500-10000g/mol之间,优选在1000-3000g/mol之间。蓖麻油聚氨酯弹性体凝胶和二亚油酸/丙二醇聚氨酯弹性体凝胶表现出类似的特性。
多元醇的另一个优选例子是二亚油酸二醇,并且据报道具有以下结构:
多元醇的另一个优选例子是二亚油酸二胺,并且据报道具有以下结构:
多元醇的另一个优选例子是六亚甲基二胺,并且具有以下结构:
其他适当的多元醇包括甘油、聚甘油、季戊四醇、季戊四醇四(3-巯基丙酸酯)、三羟甲基丙烷、硫醇化大豆油、甘油丙氧基化物、甘油基聚(氧丙烯)三胺和三聚氰胺。
进一步的示例性多元醇包括但不限于二亚油酸/丙二醇共聚物;丙二醇/壬二酸共聚物;壬二酸酯多元醇;丙二醇/癸二酸共聚物;1,3-丙二醇/壬二酸共聚物;1,3-丙二醇/癸二酸共聚物;1,3-丁二醇/壬二酸共聚物;1,3-丁二醇/癸二酸共聚物;1,4-丁二醇/壬二酸共聚物;1,4-丁二醇/癸二酸共聚物;丙二醇/己二酸共聚物;1,3-丙二醇/己二酸共聚物;1,3-丁二醇/己二酸共聚物;1,4-丁二醇/己二酸共聚物;辛酰甘油/癸二酸共聚物;三甲基戊二醇/己二酸共聚物;辛酰甘油/癸二酸共聚物;琥珀酸二庚酯(和)辛酰甘油/癸二酸共聚物;聚羟基硬脂酸;聚醚;聚丁二酸丁二醇酯;聚乳酸;聚对苯二甲酸乙二醇酯;聚酯;羟基封端的聚二甲基硅氧烷;聚乙二醇;聚噁唑啉;聚甘油;聚苯乙烯;聚羟基烷酸酯;多糖;聚交酯;聚乙烯;淀粉;纤维素;壳多糖;壳聚糖;短梗霉聚糖;胶原;明胶;木质素;多糖;藻酸盐;聚对苯二甲酸乙二醇酯;聚对苯二甲酸丙二醇酯;聚(2,5-呋喃二甲酸乙二醇酯);聚酰胺;多萜;聚2,5-呋喃二甲酸乙二醇酯;聚己内酯;聚四氢呋喃;聚交酯;聚乙交酯;聚二噁烷酮;聚碳酸酯;聚交酯-共-乙交酯;聚酐;聚磷腈;聚磷酸酯;甘油;蓖麻油;麻风果油;多羟基大豆油;棕榈油;氢化蓖麻油;辛二醇;辛酸甘油酯;乙基己基甘油;1,2-己二醇;己二醇;十一烯酸甘油酯;甲基丙二醇;1,2-己二醇;季戊四醇;二季戊四醇;三季戊四醇;三羟甲基丙烷;异山梨醇;乙二醇;二甘醇;三甘醇;四甘醇;丙二醇;二丙二醇;三丙二醇;1,3-丁二醇;1,4-丁二醇;新戊二醇;1,6-己二醇;1,4-环己烷二甲醇;乙醇胺;二乙醇胺;甲基二乙醇胺;苯基二乙醇胺;1,2,6-己三醇;三乙醇胺;二乙基甲苯二胺;二甲硫基甲苯二烷;柠檬酸;乳酸;聚乳酸;二亚油酸;三亚油酸;壬二酸;和癸二酸。
组分(C)-聚氨酯反应催化剂:
在一些实施方案中,组分(C)聚氨酯反应催化剂任选地用于增加聚氨酯弹性体形成速率。羧酸铋是用于合成聚氨酯弹性体凝胶的优选催化剂,这是由于它们有利的毒性特征和在外用产品中可接受的使用。
优选地,将新癸酸铋用作聚氨酯催化剂。也可以使用锌、锡和胺基聚氨酯催化剂。适当的聚氨酯催化剂包括但不限于:三亚乙基二胺、N,N,N',N",N"-五甲基二亚乙基三胺、1,2-二甲基咪唑、N,N,N',N'-四甲基-1,6-己二胺、N,N',N'-三甲氨基乙基哌嗪、1,1'-[[3-(二甲氨基)丙基]亚氨基]双丙-2-醇、N,N,N'-三甲氨基乙基乙醇胺、N,N',N"-三(3-二甲氨基丙基)-六氢-均三嗪、1,4-二氮杂双环[2.2.2]辛烷、辛酸亚锡、草酸亚锡、氧化亚锡、氯化亚锡、二(2-己基己酸)二辛基锡溶液、二硫代乙醇酸二辛基锡、二月桂酸二辛基锡、二辛基氧化锡共混物、二月桂酸二丁基锡、三(2-乙基己酸)单丁基锡、二酮酸二辛基锡、二乙酸二辛基锡、二辛基氧化锡、二乙酸二丁基锡、改性的二乙酸二丁基锡、二丁基氧化锡、单丁基二羟基氯化锡、有机锡氧化物、单丁基氧化锡、二辛基二羧酸锡、二辛基羧酸锡、二辛基锡锡氧烷、新癸酸锌、辛酸锌、乙酰丙酮锌、草酸锌、乙酸锌、羧酸铋和新癸酸锌。
组分(D)-载体流体
在一些实施方案中,聚氨酯弹性体含在外用可接受的任选的载体流体(D)中。在示例性实施方案中,载体流体是“外用可接受的载体流体”,其是外用于皮肤表面即皮肤、嘴唇、粘膜等的溶剂。术语“外用可接受的”和“化妆品可接受的”在本文中可互换使用,并且外用可接受的载体流体在本文中也可以称为“润肤剂”。尽管不是必需的,但通常载体流体可以与用于进行如上所述的聚氨酯弹性体反应的溶剂相同。用于合成聚氨酯弹性体橡胶和凝胶的外用可接受的载体流体可以是完全、部分或非生物基的。如本文所述,术语“生物基的”是指主要由衍生自活物质的物质(也称为生物质)组成的材料。
外用可接受的载体流体应当与形成本文所述的聚氨酯弹性体橡胶的反应相容,使得橡胶不会太硬和/或太脆而不能加工成凝胶。当将聚氨酯弹性体橡胶加工成凝胶时,应当使用具有适当极性的载体流体以便在研磨时使弹性体颗粒溶胀。如果润肤剂不能使颗粒溶胀,则聚氨酯弹性体橡胶不能加工成光滑的凝胶。具有适当极性的甘油三酯、酯和醚可以用于在研磨过程期间使弹性体颗粒溶胀。在一些实施方案中,外用可接受的载体流体包括甘油三酯、酯、烷烃、醚或其混合物。优选地,外用可接受的载体流体是三庚酸甘油酯或三庚酸甘油酯和椰油辛酸酯/癸酸酯的混合物。三庚酸甘油酯是用于使如本文所述的弹性体颗粒溶胀的优选载体流体。三庚酸甘油酯具有相对较高的极性,是100%生物基的,并且具有低粘度和轻盈不油腻的皮肤感觉。
一旦将聚氨酯弹性体橡胶加工成光滑的凝胶,就可以在高剪切混合下将具有干爽皮肤感觉的挥发性载体流体添加到凝胶中,直至达到所需的粘度。挥发性载体流体用于增强聚氨酯弹性体凝胶在皮肤上的干爽感。在此过程期间可以使用甘油三酯、酯、醚和烷烃。优选地,使用十一烷和/或十三烷和/或椰子烷烃。
聚氨酯弹性体凝胶的稳定性部分地取决于在聚氨酯弹性体橡胶和凝胶的合成中使用的载体流体或载体流体混合物。如果载体流体的极性太低,则最初可能形成凝胶,但是将随时间分离。通常,甘油三酯、酯、醚和烷烃可以以各种组合使用。优选地,使用比率为约1/1/0.5的三庚酸甘油酯、椰油辛酸酯/癸酸酯和十一烷和/或十三烷的混合物。如果发生分离,也可以使用表面活性剂来维持凝胶稳定性。
外用可接受的载体流体优选地在20℃下具有在1-65mPas之间的粘度。外用可接受的载体流体的扩散值优选地在500-2500mm2/10min之间。用于合成聚氨酯弹性体橡胶和加工聚氨酯弹性体凝胶的适当的外用可接受的载体流体包括但不限于:双-二甘油基多酰基己二酸酯-1、双-二甘油基多酰基己二酸酯-1、双-二甘油基多酰基己二酸酯-2、丁二醇二辛酸酯/二癸酸酯、乳木果(Butyrospermum Parkii)油、辛酸/癸酸甘油酯、辛酸/癸酸甘油三酯、辛酸/癸酸/肉豆蔻酸/硬脂酸甘油三酯、辛酸/癸酸/琥珀酸甘油三酯、辛基聚甲基硅氧烷、椰油辛酸酯/癸酸酯、十甲基环戊硅氧烷、油酸癸酯、聚二甲基硅氧烷醇、二苯基硅烷二醇、十二甲基环己硅氧烷、乙基三硅氧烷、辛酸甘油酯、辛酸甘油酯、柠檬酸/乳酸/亚油酸/油酸甘油酯、柠檬酸/乳酸/亚油酸/油酸甘油酯、椰油酸甘油酯、异硬脂酸甘油酯、油酸甘油酯、蓖麻酸甘油酯、蓖麻酸甘油酯、生育酚、硬脂酸甘油酯、硬脂酸甘油酯、柠檬酸硬脂酸甘油酯、六甲基二硅氮烷、六甲基二硅氧烷、氢化椰油甘油酯、氢化棕榈油、羟基三甲基硅烷、异丙氧基三甲基硅烷、异硬脂酸甲基庚酯、八甲基环四硅氧烷、芥酸油醇酯、Olus油、有机改性的硅氧烷、有机硅流体、PCA甘油油酸酯、PEG-6辛酸/癸酸甘油酯、苯基三氯硅烷、聚(二甲基硅氧烷)、含聚(乙二醇)的硅氧烷、聚二甲基硅氧烷、聚甘油基-2癸酸酯、聚甘油基-3癸酸酯、聚甘油基-3癸酸酯、聚甘油基-3二异硬脂酸酯、聚甘油基-3聚蓖麻酸酯、聚甘油基-4椰油酸酯、聚甘油基-4椰油酸酯、碳酸丙烯酯、碳酸丙烯酯、碳酸丙烯酯、碳酸丙烯酯、丙二醇二辛酸酯/二癸酸酯、丙二醇二辛酸酯/二癸酸酯、丙二醇二辛酸酯/二癸酸酯、硅油、司拉氯铵膨润土、司拉氯铵锂蒙脱石、司拉氯铵锂蒙脱石、司拉氯铵锂蒙脱石、三庚酸甘油酯、三甲基(溴二氟甲基)硅烷、三肉豆蔻酸甘油酯和三硬脂酸甘油酯。
在一些实施方案中,外用可接受的载体流体的浓度为凝胶组合物的约0%至约99.9%(w/w)、凝胶组合物的约1%(w/w)至约99.9%(w/w)、凝胶组合物的约10%(w/w)至约99.9%(w/w)、凝胶组合物的约20%(w/w)至约99.9%(w/w)、凝胶组合物的约30%(w/w)至约99.9%(w/w)、凝胶组合物的约40%(w/w)至约99.9%(w/w)、凝胶组合物的约50%(w/w)至约99.9%(w/w)、凝胶组合物的约60%(w/w)至约99.9%(w/w)、凝胶组合物的约70%(w/w)至约99.9%(w/w)、凝胶组合物的约80%(w/w)至约99.9%(w/w)或凝胶组合物的约90%(w/w)至约99.9%(w/w)。在某些实施方案中,凝胶组合物不包含外用可接受的载体流体。在一些实施方案中,用于制备本文的凝胶组合物的方法在外用可接受的载体流体的存在下进行。在进一步的实施方案中,用于制备本文的凝胶组合物的方法不在外用可接受的载体流体的存在下进行。
组分(E)-活性成分
在一些实施方案中,本文的凝胶组合物进一步包含组分(E)活性成分。
在一些实施方案中,组分(E)是选自任何个人或保健活性成分的“药物活性成分”。如本文所用,“药物活性成分”意指本领域已知作为个人护理配方中的添加剂的任何化合物或化合物混合物,其通常出于治疗皮肤、嘴唇或提供化妆和/或美学益处的目的而添加。“保健活性成分”意指本领域已知的提供药物或医学益处的任何化合物或化合物混合物。因此,“保健活性成分”包括如被美国卫生与人类服务部食品和药物管理局普遍使用和定义的活性成分或活性药物成分的材料,其含在美国联邦法规第I章第21篇第200-299部分和第300-499部分中。因此,活性成分可以包括旨在在疾病的诊断、治愈、缓解、治疗或预防中提供药理活性或其他直接作用,或影响人或其他动物身体的结构或任何功能的任何组分。所述短语可以包括在药物产品的制造中可经历化学变化并以旨在提供指定的活性或效果的改性形式存在于药物产品中的那些组分。
活性成分的一些代表性例子包括:药物,维生素,矿物质,激素,外用抗微生物剂(诸如抗生素活性成分,用于治疗脚癣、股癣或癣的抗真菌活性成分,和痤疮活性成分),收敛剂活性成分,除臭剂活性成分,疣去除剂活性成分,鸡眼和胼胝去除剂活性成分,用于治疗头虱、阴虱(蟹虱)和体虱的杀虱剂活性成分,用于控制头皮屑、脂溢性皮炎或牛皮癣的活性成分,以及晒伤防治剂。
用于在根据本发明的方法中使用的有用活性成分包括维生素及其衍生物,包括“维生素原”。在本文中有用的维生素包括但不限于维生素A、视黄醇、视黄醇的C-C酯、维生素E、生育酚、维生素E的酯及其混合物。视黄醇包括反式视黄醇、1.3-顺式视黄醇、11-顺式视黄醇、9-顺式视黄醇和3,4-二脱氢-视黄醇、维生素C及其衍生物、维生素B、维生素B。维生素原B5、泛醇、维生素B、维生素B2、烟酸、叶酸、生物素和泛酸。在本文中考虑包括的其他合适的维生素和维生素的INCI名称是抗坏血酸二棕榈酸酯、抗坏血酸甲基硅烷醇果胶酸酯、抗坏血酸棕榈酸酯、抗坏血酸硬脂酸酯、抗坏血酸葡糖苷、抗坏血酸磷酸酯钠、抗坏血酸钠、抗坏血酸硫酸酯二钠、(抗坏血酸/生育酚)磷酸酯钾。
应当注意,视黄醇是由华盛顿特区的化妆品、盥洗用品和香水协会(TheCosmetic,Toiletry,and Fragrance Association,CTFA)指定用于维生素A的化妆品成分国际命名(International Nomenclature Cosmetic Ingredient,INCI)名称。在本文中考虑包括的其他合适的维生素和维生素的INCI名称是视黄醇乙酸酯、视黄醇棕榈酸酯、视黄醇丙酸酯、邻生育酚、托可索仑、生育酚乙酸酯、生育酚亚油酸酯、生育酚烟酸酯和生育酚琥珀酸酯。
用于根据本发明的方法的药物活性成分可以是活性药物成分。可使用的一些合适的活性药物成分的代表性例子是氢化可的松、酮洛芬、噻吗洛尔、匹罗卡品、阿霉素、丝裂霉素C、吗啡、氢吗啡酮、地尔硫卓、茶碱、多柔比星、柔红霉素、肝素、青霉素G、羧苄青霉素、头孢噻吩、头孢西丁、头孢噻肟、5-氟尿嘧啶、阿糖胞苷、6-氮尿苷、6-硫鸟嘌呤、长春碱、长春新碱、硫酸博来霉素、金硫葡萄糖、苏拉明、甲苯达唑、可乐定、东莨菪碱、普萘洛尔、盐酸苯丙醇胺、哇巴因、阿托品、氟哌啶醇、异山梨醇、硝酸甘油、布洛芬、泛醌、吲哚美辛、前列腺素、萘普生、沙丁胺醇、胍那苄、拉贝洛尔、非尼拉敏、美曲磷脂和类固醇。
出于本发明的目的,考虑作为活性药物成分包括在本文中的是抗痤疮剂,诸如过氧化苯甲酰和维甲酸;抗细菌剂,诸如氯己二烯葡糖酸盐;抗真菌剂,诸如硝酸咪康唑;抗炎剂;皮质类固醇药物;非类固醇抗炎剂,诸如双氯芬酸;抗银屑病剂,诸如丙酸氯倍他索;麻醉剂,诸如利多卡因;止痒剂;抗皮炎剂;以及通常被认为是阻隔膜的药剂。
本发明的药物活性成分E)可以是蛋白质,诸如酶。在聚氨酯弹性体凝胶中内部包含酶具有防止酶失活和较长时间维持酶的生物活性作用的优点。酶包括但不限于市售型、改良型、重组型、野生型、在自然界中未发现的变体及其混合物。例如,合适的酶包括水解酶、角质酶、氧化酶、转移酶、还原酶、半纤维素酶、酯酶、异构酶、果胶酶、乳糖酶、过氧化物酶、漆酶、过氧化氢酶及其混合物。水解酶包括但不限于蛋白酶(细菌、真菌、酸性、中性或碱性)、淀粉酶(α或β)、脂肪酶、甘露聚糖酶、纤维素酶、胶原酶、溶菌酶、超氧化物歧化酶、过氧化氢酶及其混合物。所述蛋白酶包括但不限于胰蛋白酶、胰凝乳蛋白酶、胃蛋白酶、胰酶和其他哺乳动物酶;木瓜蛋白酶、菠萝蛋白酶和其他植物酶;枯草杆菌蛋白酶、表皮素、乳链菌肽、柚苷酶(L-鼠李糖苷酶)尿激酶和其他细菌酶。所述脂肪酶包括但不限于三酰基-甘油脂肪酶、单酰基甘油脂肪酶、脂蛋白脂肪酶,例如胰脂酶、肠蛋白酶、胃蛋白酶、其他哺乳动物、植物、细菌脂肪酶和纯化的脂肪酶。天然木瓜蛋白酶优选作为所述酶。进一步地,刺激性激素(例如胰岛素)可以与这些酶一起使用以增强它们的有效性。
药物活性成分还可以是防晒剂。防晒剂可以选自本领域已知的保护皮肤免受暴露于阳光的有害影响的任何防晒剂。防晒化合物通常选自吸收紫外(UV)光的有机化合物、无机化合物或其混合物。因此,可用作防晒剂的代表性的非限制性例子包括:氨基苯甲酸、西诺沙酯、甲氧基肉桂酸二乙醇胺、二没食子酰三油酸酯、二羟苯宗、4-双(羟基丙基)氨基苯甲酸乙酯、氨基苯甲酸甘油酯、胡莫柳酯、指甲花醌与二羟基丙酮、邻氨基苯甲酸薄荷酯、奥克立林、甲氧基肉桂酸辛酯、水杨酸辛酯、氧苯酮、帕地马酯O、苯基苯并咪唑磺酸、红凡士林、舒利苯酮、二氧化钛、水杨酸三乙醇胺、cetarninosalol、尿囊素、PABA、亚苄基酞、二苯甲酮、二苯甲酮1-12、3-亚苄基樟脑、亚苄基樟脑水解胶原磺酰胺、亚苄基樟脑磺酸、水杨酸苄酯、bomelone、布美三唑(bumetriozole)、丁基甲氧基二苯甲酰甲烷、丁基PABA、二氧化铈/二氧化硅、二氧化铈/二氧化硅滑石、西诺沙酯、DEA-甲氧基肉桂酸酯、二苯并噁唑萘、二叔丁基羟基亚苄基樟脑、二没食子酰三油酸酯、二异丙基肉桂酸甲酯、二甲基PABA乙基鲸蜡硬脂基二甲基铵甲苯磺酸盐、二辛基丁酰胺基三嗪酮、二苯基甲酯基乙酰氧基萘并吡喃、双乙基苯基三氨基三嗪二苯乙烯二磺酸二钠、二苯乙烯基二苯基三氨基三嗪二苯乙烯二磺酸二钠、二苯乙烯基二苯基二磺酸二钠、甲酚曲唑、甲酚曲唑三硅氧烷、乙基二羟基丙基PABA、二异丙基肉桂酸乙酯、甲氧基肉桂酸乙酯、乙基PABA、尿刊酸乙酯、依托立林(etrocrylene)阿魏酸、辛酸二甲氧基肉桂酸甘油酯、甘油基PABA、水杨酸乙二醇酯、胡莫柳酯、对甲氧基肉桂酸异戊酯、水杨酸异丙基苄酯、异丙基二苯甲酰甲烷、甲氧基肉桂酸异丙酯、邻氨基苯甲酸薄荷酯、水杨酸薄荷酯、4-甲基亚苄基樟脑、奥克立林、奥克三唑、辛基二甲基PABA、甲氧基肉桂酸辛酯、水杨酸辛酯、辛基三嗪酮、PABA、PEG-25PABA、戊基二甲基PABA、苯基苯并咪唑磺酸、聚丙烯酰胺甲基亚苄基樟脑、甲氧基肉桂酸钾、苯基苯并咪唑磺酸钾、红凡士林、苯基苯并咪唑磺酸钠、尿刊酸钠、TEA-苯基苯并咪唑磺酸盐、TEA-水杨酸盐、对苯二亚甲基二樟脑磺酸、二氧化钛、二氧化锌、二氧化铈、三PABA泛醇、尿刊酸和VA/巴豆酸(酯)/甲基丙烯酰氧基二苯甲酮-1共聚物。
防晒剂可以是单一的一种或多于一种的组合。可替代地,防晒剂是肉桂酸酯基有机化合物,或者可替代地,防晒剂是甲氧基肉桂酸辛酯,诸如Uvinul R.MC 80(对甲氧基肉桂酸和2-乙基己醇的酯)。
组分(E)也可以是香料或香精。香精可以是香精工业中常用的任何香精或香料活性成分。这些组合物通常属于多种化学类别,如醇、醛、酮、酯、醚、乙酸酯、亚硝酸酯、萜烯烃、含氮或硫的杂环化合物以及天然或合成来源的精油。许多这些香精成分详细描述于标准教科书参考文献中,诸如Perfume and Flavour Chemicals,1969,S.Arctander,Montclair,N.J。
香料的例子可以是但不限于香精酮和香精醛。说明性的香精酮是布枯肟(buccoxime)、异茉莉酮、甲基β萘基酮、麝香茚酮、吐纳麝香/麝香+、α大马酮、β-大马酮、δ-大马酮、异大马酮、大马烯酮、大马玫瑰(Damarose)、二氢茉莉酮酸甲酯、薄荷酮、香芹酮、樟脑、小茴香酮、α-紫罗兰酮、β-紫罗兰酮、γ-甲基所谓的紫罗兰酮、2-庚基环戊酮(Fleuramone)、二氢茉莉酮、顺式茉莉酮、龙涎酮(Iso-E-Super)、甲基柏木酮(Methyl-Cedrenyl-ketone或Methyl-Cedrylone)、苯乙酮、甲基-苯乙酮、对甲氧基-苯乙酮、甲基-β-萘基-酮、苄基-丙酮、二苯甲酮、对羟基-苯基-丁酮、芹菜酮(Celery Ketone或LiveScone)、6-异丙基十氢-2-萘酮、二甲基-辛烯酮、鲜薄荷酮(Freskomenthe)、4-(1-乙氧基乙烯基)-3,3,5,5,-四甲基-环己酮、甲基-庚烯酮、2-(2-(4-甲基-3-环己烯-1-基)丙基)-环戊酮、1-(对薄荷烯-6(2)-基)-1-丙酮、4-(4-羟基-3-甲氧基苯基)-2-丁酮、2-乙酰基-3,3-二甲基降冰片烷、6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮、4-大马醇(Damascol)、Dulcinyl或Cassione、2-己基乙酰乙酸乙酯(Gelsone)、Hexylon、龙涎酮(Isocyclemone E)、甲基环柠檬酮(Methyl Cyclocitrone)、甲基熏衣草酮(Methyl Lavender-Ketone)、Orivon、对叔丁基-环己酮、芳多酮(Verdone)、2-戊基环戊酮(Delphone)、麝香酮、新丁烯酮、普利卡酮(Plica tone)、凡路酮(Veloutone)、2,4,4,7-四甲基-辛-6-烯-3-酮和Tetrameran。
更优选地,香精酮因其气味特征而选自α大马酮、δ大马酮、异大马酮、香芹酮、γ-甲基-紫罗兰酮、龙涎酮、2.4.4.7-四甲基-辛-6-烯-3-酮、苄基丙酮、β大马酮、大马烯酮、二氢茉莉酮酸甲酯、甲基柏木酮及其混合物。
优选地,香精醛因其气味特征而选自阿道克醛、大茴香醛、环丁碳杂氧杂脒(cymal)、乙基香草醛、花青醛、新洋茉莉醛、洋茉莉醛、羟基香茅醛、高芳烯(koavone)、月桂醛、新铃兰醛、甲基壬基乙醛、芳香醋醛(P.T.bucinal)、苯乙醛、十一烯醛、香草醛、2,6,10-三甲基-9-十一烯醛、3-十二烯-1-醛、α-正戊基肉桂醛、4-甲氧基苯甲醛、苯甲醛、3-(4-叔丁基苯基)-丙醛、2-甲基-3-(对甲氧基苯基)丙醛、2-甲基-4-(2,6,6-三甲基-2(1)-环己烯-1-基)丁醛、3-苯基-2-丙烯醛、顺式/反式3,7-二甲基-2,6-辛二烯-1-醛、3,7-二甲基-6-辛烯-1-醛、(3,7-二甲基-6-辛烯基)氧基乙醛、4-异丙基苯甲醛、1,2,3,4,5,6,7,8-八氢-8.8-二甲基-2-萘甲醛、2,4-二甲基-3-环己烯-1-甲醛、2-甲基-3-(异丙基苯基)丙醛、1-癸醛(decanal;decyl aldehyde)、2,6-二甲基-5-庚烯醛、4-(三环[5.2.1.0(2,6)]-亚癸基-8)-丁醛、八氢-4,7-甲桥-1H-茚甲醛、3-乙氧基-4-羟基苯甲醛、对乙基-α,α-二甲基氢化肉桂醛、α-甲基-3,4-(亚甲二氧基)-氢化肉桂醛、3,4-亚甲基二氧基苯甲醛、α-正己基肉桂醛、间伞花烃-7-甲醛、α-甲基苯基乙醛、7-羟基-3,7-二甲基辛醛、十一烯醛、2,4,6-三甲基-3-环己烯-1-甲醛、4-(3)(4-甲基-3-戊烯基)-3-环己烯-甲醛、1-十二醛、2,4-二甲基环己烯-3-甲醛、4-(4-羟基-4-甲基戊基)-3-环己烯1-甲醛、7-甲氧基-3,7-二甲基辛-1-醛、2-甲基十一醛、2-甲基癸醛、1-壬醛、1-辛醛、2,6,10-三甲基-5.9-十一碳二烯醛、2-甲基-3-(4-叔丁基)丙醛、二氢肉桂醛、1-甲基-4-(4-甲基3-戊烯基)-3-环己烯-1-甲醛、5(或6)-甲氧基六氢-4,7-甲桥茚满-1(或2)-甲醛、3,7-二甲基辛-1-醛、1-十一醛、10-十一烯-1-醛、4-羟基-3-甲氧基苯甲醛、1-甲基-3-(4-甲基戊基)-3-环己烯甲醛、7-羟基-3,7-二甲基辛醛、反式4-癸烯醛、2,6-壬二烯醛、对甲苯基乙醛、4-甲基苯基乙醛、2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯醛、邻甲氧基肉桂醛、3,5,6-三甲基-3-环己烯甲醛、3,7-二甲基-2-亚甲基-6-辛烯醛、苯氧基乙醛、5,9-二甲基-4,8-癸二烯醛、芍药醛(6,10-二甲基-3-氧杂-5.9-十一碳二烯-1-醛)、六氢-4,7-甲桥茚满-1-甲醛、2-甲基辛醛、α-甲基-4-(1-甲基乙基)苯乙醛、6,6-二甲基-2-降蒎烯-2-丙醛、对甲基苯氧基乙醛、2-甲基-3-苯基-2-丙烯-1-醛、3.5.5-三甲基己醛、六氢-8,8-二甲基-2-萘甲醛、3-丙基-双环[2.2.1]-庚-5-烯-2-甲醛、9-癸烯醛、3-甲基-5-苯基-1-戊醛、甲基壬基乙醛、己醛、反式2-己烯醛、1-对薄荷烯-q-甲醛及其混合物。更优选的醛因其气味特征而选自1-癸醛、苯甲醛、花青醛、2,4-二甲基-3-环己烯-1-甲醛、顺式/反式3,7-二甲基-2,6-辛二烯-1-醛、洋茉莉醛、2,4,6-三甲基-3-环己烯-1-甲醛、2,6-壬二烯醛、α-戊基-肉桂醛、α-正己基-肉桂醛、芳香醋醛、新铃兰醛、环丁碳杂氧杂脒、甲基壬基乙醛、己醛、反式2-己烯醛及其混合物。在香精成分的上述列表中,一些是本领域技术人员常规已知的商品名,并且还包括异构体。此类异构体也适用于在本发明中使用。
组分(E)也可以是一种或多种植物提取物。这些组分的例子如下:明日叶(Ashitaba)提取物、鳄梨提取物、绣球花属植物(hydrangea)提取物、蜀葵属植物(Althea)提取物、山金车属植物(Arnica)提取物、芦荟属(aloe)提取物、杏提取物、杏仁提取物、银杏(Ginkgo Biloba)提取物、小茴香提取物、姜黄(turmeric Curcuma)提取物、乌龙茶提取物、玫瑰果提取物、紫锥花属(Echinacea)提取物、黄芩属(Scutellaria)根提取物、黄柏属(Phellodendro)树皮提取物、日本黄连提取物、大麦提取物、金丝桃属(Hyperium)提取物、白荨麻提取物、豆瓣菜提取物、柑橘提取物、脱水盐水、海草提取物、水解弹性蛋白、水解小麦粉、水解蚕丝、洋甘菊提取物、胡萝卜提取物、蒿属(Artemisia)提取物、甘草属(Glycyrrhiza)提取物、芙蓉茶提取物、火棘果提取物、猕猴桃提取物、金鸡纳属(Cinchona)提取物、黄瓜提取物、鸟苷、栀子属(Gardenia)提取物、山白竹(Sasa Albo-marginata)提取物、苦参属(Sophora)根提取物、核桃提取物、葡萄柚提取物、铁线莲属(Clematis)提取物、小球藻属(Chlorella)提取物、桑椹提取物、龙胆属(Gentiana)提取物、红茶提取物、酵母提取物、牛蒡提取物、米糠发酵提取物、稻米胚芽油、紫草科植物(comfrey)提取物、胶原蛋白、越橘提取物、栀子属(Gardenia)提取物、萍叶细辛属(Asiasarum)根提取物、柴胡属(Bupleurum)科提取物、脐带提取物、鼠尾草属(Salvia)提取物、肥皂草属(Saponaria)提取物、竹提取物、山楂属(Crataegus)果提取物、花椒属(Zanthoxylum)果提取物、香菇提取物、地黄根提取物、紫草属(gromwell)提取物、紫苏属(Perilla)提取物、椴树提取物、蚊子草属(Filipendula)提取物、芍药提取物、省藤属(calamus)根提取物、白桦树提取物、马尾草提取物、洋常春藤(Hedera Helix)(Ivy)提取物、山楂提取物、接骨木(Sambucus migra)提取物、欧蓍草(Achillea millefolium)提取物、洋薄荷(Mentha piperita)提取物、鼠尾草提取物、锦葵属植物(mallow)提取物、川芎(Cnidium officinale)根提取物、日本绿色龙胆提取物、大豆提取物、枣提取物、百里香属(thyme)提取物、茶提取物、丁香提取物、禾本科白茅属(Gramineae imperata cyrillo)提取物、蜜柑皮提取物、日本当归根提取物、金盏花属(calendula)提取物、桃仁提取物、苦橙皮提取物、鱼腥草(Houttuyna cordata)提取物、番茄提取物、纳豆提取物、人参提取物、绿茶提取物(茶树(camelliea sine sis))、大蒜提取物、野玫瑰提取物、木槿属(hibiscus)提取物、沿阶草属(Ophiopogon)块茎提取物、荷花(Nelumbo nucifera)提取物、欧芹提取物、蜂蜜、金缕梅属(hamamelis)提取物、墙草属(parietaria)提取物、溪黄草(isodonis herba)提取物、红没药醇提取物、枇杷提取物、款冬提取物、蜂斗菜提取物、茯苓(Poria cocos wolf)提取物、假叶树提取物、葡萄提取物、蜂胶提取物、丝瓜提取物、红花提取物、薄荷提取物、椴树提取物、芍药属(Paeonia)提取物、啤酒花提取物、松树提取物、七叶树提取物、水芭蕉(Mizu-bashou Lysichitoncamtschatcese)提取物、无患子果皮提取物、蜜蜂花提取物、桃提取物、矢车菊提取物、桉属(eucalyptus)提取物、虎耳草属植物(saxifrage)提取物、香橼提取物、薏苡属(coix)提取物、艾属植物(mugwort)提取物、薰衣草提取物、苹果提取物、莴苣提取物、柠檬提取物、紫云英提取物、玫瑰提取物、迷迭香提取物、罗马洋甘菊提取物和蜂王浆提取物。
存在于聚氨酯凝胶组合物中的组分(E)的量可以变化,但是通常范围如下:0.05至50wt%、可替代地1至25wt%或者可替代地1至10wt%,基于按存在于组合物中的聚氨酯弹性体凝胶的重量(即凝胶组合物中组分(A)、(B)、(C)和(D)的总重量)计的量。
组分(E)可以在制备聚氨酯弹性体期间添加到聚氨酯凝胶组合物中(预加载方法),或者在形成聚氨酯弹性体凝胶之后添加(后加载方法)。
预加载方法包括:使以下物质反应:(A)多异氰酸酯;(B)多元醇;和(C)任选的聚氨酯反应催化剂,任选地在(D)载体流体中;以及将(E)个人护理或保健活性物质与聚氨酯弹性体凝胶混合以形成含有活性物质的聚氨酯弹性体凝胶。
后加载方法包括:(I)使以下物质反应:(A)多异氰酸酯;(B)多元醇;(C)任选的聚氨酯反应催化剂,任选地在(D)载体流体中以形成聚氨酯弹性体凝胶;(II)将聚氨酯弹性体凝胶剪切成光滑的糊状物;以及(III)将(E)个人护理或保健活性成分与聚氨酯弹性体凝胶混合以形成含有活性物质的聚氨酯弹性体凝胶。个人护理活性物质也可以作为另一种混合物的组分与一种或多种赋形剂混合。
聚氨酯弹性体
本发明的聚氨酯弹性体可作为组分(A)多异氰酸酯、(B)多元醇和(C)任选的聚氨酯反应催化剂任选地在(D)载体流体中的聚氨酯反应产物获得。术语“聚氨酯反应”意指在催化剂(诸如组分(C))的存在下,将含有羟基的化合物(诸如组分(A))添加到含有异氰酸酯基团的化合物(诸如组分(B))中,其中羟基与异氰酸酯基团的摩尔比为1:1。可替代地,此比率的范围可以从8:1至0.9:1。聚氨酯反应在溶剂的存在下进行,其中溶剂与描述为组分(D)的载体流体相同并且不经进一步纯化即使用。
在一个具体的实施方案中,本发明提供了交联聚氨酯弹性体网络,其根据以下通用结构并通过以下通用方案制备(所描绘的结构基于蓖麻油的主要甘油三酯组分甘油三蓖麻油酸酯),由蓖麻油与异佛尔酮二异氰酸酯的反应形成:
在一个进一步的实施方案中,聚氨酯弹性体的结构是重复单元二亚油酸/丙二醇共聚物、氨基甲酸烷基酯和三嗪三酮的交联聚合物网络。聚氨酯聚合物网络的典型化学结构如下所示并根据以下反应方案形成:
在某些实施方案中,以三步法制备上述聚氨酯弹性体凝胶。首先,使二亚油酸/丙二醇共聚物与1,5-五亚甲基二异氰酸酯三聚体在新癸酸铋的存在下在三庚酸甘油酯和椰油辛酸酯/癸酸酯的反应介质中在升高的温度下在混合下反应。二亚油酸/丙二醇共聚物的分子量范围为约1000-3000。多异氰酸酯的NCO与共聚物的OH的摩尔比可以在2:1至1:2之间。新癸酸铋在反应混合物中的量可以在大约0.05-2.25重量%之间。在催化剂的存在下,在共聚物的羟基与多异氰酸酯的异氰酸酯基团之间发生反应,以产生氨基甲酸酯键-RNHCOOR'-。产物是交联聚氨酯弹性体橡胶,其中外用可接受的载体流体三庚酸甘油酯和椰油辛酸酯/癸酸酯包埋在弹性体基质中。所得灰白色橡胶是柔软的,不是脆性的,并且触摸起来稍粘。在第二步中,用载体流体(诸如三庚酸甘油酯)稀释橡胶,并且使用高剪切混合器、分散器或均化器将其研磨成凝胶。所得凝胶浓缩物是稠厚且光滑的,没有颗粒。当施用于皮肤时,凝胶容易地被吸收并均匀地扩散而没有起球。在第三步中,可以用高剪切混合器将载体流体(诸如十一烷和/或十三烷或椰子烷烃)添加到凝胶浓缩物中,直至达到所需的粘度。
聚氨酯弹性体橡胶的硬度是决定其是否可以容易地加工成凝胶的重要因素。如果聚氨酯弹性体橡胶太硬,则橡胶颗粒在加工时将不会适当地溶胀或碾磨成光滑的凝胶。如果聚氨酯弹性体橡胶太软,由于粘性和缺乏可溶胀颗粒,它将不容易加工成凝胶。五个因素主要决定聚氨酯弹性体橡胶的硬度。
第一个,如由聚氨酯弹性体橡胶的合成中反应物的重量百分比确定的固体含量是决定聚氨酯弹性体橡胶硬度和胶凝能力的关键因素。如果固体含量太高,则橡胶将是硬且脆的。如果固体含量太低,则橡胶将是粘且软的。在实践中,橡胶形成中反应物的总重量百分比可以在70%-95%之间。
第二个,一种或多种外用可接受的载体流体的身份影响聚氨酯硬度和加工。如果将椰油辛酸酯/癸酸酯用作唯一的载体流体,则聚氨酯弹性体橡胶可能太硬太脆,因此将不会加工成光滑的凝胶。使用三庚酸甘油酯或比率为4:1至1:1的三庚酸甘油酯与椰油辛酸酯/癸酸酯的混合物可以产生具有适当硬度的聚氨酯弹性体橡胶。优选地,使用3:1的比率。
第三个,多元醇与多异氰酸酯基多异氰酸酯的比率影响聚氨酯弹性体橡胶硬度。如果羟基与异氰酸酯的摩尔比太大或太小,则将不会发生充分的交联,并且将形成软且粘的产物,其不能被加工成凝胶。所述异氰酸酯的NCO与所述多元醇的OH的摩尔比可以在2:1至1:2之间。
第四个,用于合成聚氨酯弹性体橡胶的铋催化剂的量是决定其加工成凝胶的能力的另一个因素。如果使用太多的催化剂,则橡胶将在加热时过度固化,并且将太硬而不能加工成凝胶。如果使用太少的催化剂,则将不会形成橡胶。在实践中,铋催化剂的量可以为约0.05-2.25重量%。
第五个,反应温度不应当超过80℃,或者弹性体橡胶可能过度固化,导致橡胶太硬。此外,可能在高于80℃的温度下发生溶剂的泄漏。橡胶形成的反应温度应当为约40℃-80℃。
用于测量聚氨酯弹性体凝胶糊状物的粘度的方法
当与装配有特殊T形杆式锭子的合适的Brookfield粘度计一起使用时,Brookfield HELIPATHTM支架将允许以厘泊值测量具有类似于糊状物、油灰、乳膏、明胶或蜡的特征的材料的粘度/稠度。使用具有HELIPATHTM支架(Brookfield型号D)和T形杆锭子(Brookfield HELIPATHTM锭子组)的Brookfield型号DV-II+Pro粘度计确定聚氨酯弹性体共混物的粘度。所有均购自Brookfield Engineering Laboratories,Inc.(美国马萨诸塞州米德尔伯勒商业大道11号(11Commerce Boulevard Middleboro,Mass.,USA))。需要在4盎司圆罐中装入50g样品量。在测量前使用以下制备程序:首先经由离心从样品中除去气泡,然后在真空下保持两小时。在除气后,将样品在25℃下调节最少4小时。根据HELIPATHTM锭子的典型程序进行测量。通常,使用锭子93(T形杆锭子E),并且rpm的标准设置为6.5。将锭子速度维持在恒定的6.5rpm下。
外用制剂
本文还提供了包含所述凝胶组合物或凝胶糊状物的外用制剂。在此类制剂中,凝胶组合物或凝胶糊状物适合用作外用制剂的增稠剂或稳定剂。外用制剂的其他组分是本领域已知的,并且可以包括例如各种组分,诸如乳化稳定剂、乳化剂、皮肤调理剂、助悬剂等。这些另外组分的量可以近似约0.01重量%至约50重量%。
如本文所用,“乳化稳定剂”是指有助于防止乳液分离成其油组分和水性组分的组合物。在实施方案中,用于本文所述的制剂中的乳化稳定剂是天然衍生的树胶或改性树胶或天然矿物质。示例性乳化稳定剂包括但不限于阿拉伯胶、纤维素、结晶纤维素、结冷胶、瓜尔胶、刺槐豆胶(角豆胶)、黄原胶、硅酸铝镁、膨润土或锂蒙脱石粘土等,包括其组合。
如本文所用,“皮肤调理剂”是指在皮肤表面上充当润滑剂的组合物或增加皮肤表面的含水量的组合物。用于在制剂中使用的示例性皮肤调理剂包括但不限于己二酸酯、苯甲酸烷基酯、C8或更高的脂肪酸酯、酯化芥酸酯、月桂酸酯、新戊酸酯、水杨酸酯、硬脂酸酯、甘油三酯、碳酸酯、二醇、甘油、矿物油等,包括其组合。
如本文所用,“乳化剂”是指有助于形成水包油或油包水乳液的组合物。用于在制剂中使用的示例性乳化剂包括但不限于聚山梨醇酯,乙氧基化脂肪酸,用氢氧化钠、氢氧化钾或胺中和的脂肪酸,取代的葡糖苷,月桂基和月桂基醚硫酸钠,乙氧基化酯,卵磷脂和卵磷脂衍生物等,包括其组合。
如本文所用,“助悬剂”是指改变固体颗粒与液体介质之间的界面以改善颗粒对聚在一起和从溶液中脱落的抗性的组合物。用于在制剂中使用的示例性助悬剂包括但不限于羟基硬脂酸、聚羟基硬脂酸、聚丙烯酸钠聚合物、甲基丙烯酸甲酯交联聚合物等,包括其组合。
在另外的实施方案中,聚氨酯弹性体可以以固体基形式利用,包括例如作为足部贴合鞋垫或鞋底。
示例性实施方案
实施方案1:一种包含聚氨酯弹性体凝胶的凝胶组合物,所述聚氨酯弹性体凝胶由以下物质的反应制备:
(A)包含两个或更多个异氰酸酯官能团的多异氰酸酯或多异氰酸酯混合物;
(B)包含两个或更多个羟基、胺、硫醇或羧酸官能团的多元醇或多元醇混合物;
(C)任选的聚氨酯反应催化剂;以及
(D)任选的外用可接受的载体流体。
实施方案2:根据实施方案1所述的凝胶组合物,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体、油及其组合。
实施方案3:根据实施方案1所述的凝胶组合物,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯、椰油辛酸酯/癸酸酯、三庚酸甘油酯、辛酸/癸酸甘油三酯、十二烷、十三烷、C13-15烷烃、角鲨烯、角鲨烯、月桂酸异戊酯(isoamyl laurate)、月桂酸异戊酯(isopentyl laurate)、辛酸/癸酸/肉豆蔻酸/硬脂酸甘油三酯、辛酸/癸酸/琥珀酸甘油三酯、肉豆蔻酸异丙酯、荷荷巴酯、三辛酸甘油酯和棕榈油。
实施方案4:根据实施方案1所述的凝胶组合物,其进一步包含溶解在所述外用可接受的载体流体中的药物活性成分。
实施方案5:根据实施方案1所述的凝胶组合物,其中所述多异氰酸酯或多异氰酸酯混合物是低分子量多异氰酸酯或多异氰酸酯混合物,并且其中所述多元醇或多元醇混合物含有两个或更多个羟基、胺、硫醇或羧酸基团。
实施方案6:一种包含聚氨酯弹性体的凝胶组合物,所述聚氨酯弹性体来自以下物质的反应:
(A)蓖麻油;
(B)异佛尔酮二异氰酸酯,其中异氰酸酯基团与羟基的摩尔比在1:1与1:2之间;
(C)任选的聚氨酯反应催化剂;以及
(D)浓度为所述凝胶组合物的60%(w/w)至99.9%(w/w)的外用可接受的载体流体;
其中通过在形成所述聚氨酯弹性体凝胶期间将个人护理或保健活性成分溶解在所述外用可接受的溶剂中,或者通过将所述个人护理或保健活性成分与形成的聚氨酯弹性体凝胶混合,将所述个人护理或保健活性成分任选地掺入所述聚氨酯弹性体凝胶中。
实施方案7:根据实施方案6所述的凝胶组合物,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体及其组合。
实施方案8:根据实施方案6所述的凝胶组合物,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯和椰油辛酸酯/癸酸酯。
实施方案9:根据实施方案6所述的凝胶组合物,其进一步包含溶解在所述外用可接受的载体流体中的药物活性成分。
实施方案10:根据实施方案1所述的凝胶组合物,其中所述聚氨酯催化剂是含铋基团的催化剂。
实施方案11:根据实施方案6所述的凝胶组合物,其中所述聚氨酯催化剂是含铋基团的催化剂。
实施方案12:根据实施方案1所述的凝胶组合物,其中所述外用可接受的溶剂的大于50%的碳含量衍生自植物来源。
实施方案13:根据实施方案6所述的凝胶组合物,其中所述外用可接受的溶剂的大于50%的碳含量衍生自植物来源。
实施方案14:一种用于制备根据实施方案1所述的凝胶组合物的方法,所述方法包括使以下物质:
(A)多元醇;
(B)异佛尔酮二异氰酸酯;以及
(C)任选的聚氨酯反应催化剂;
任选地在
(D)外用可接受的载体流体的存在下反应。
实施方案15:一种用于制备根据实施方案6所述的凝胶组合物的方法,所述方法包括使以下物质:
(A)蓖麻油;
(B)异佛尔酮二异氰酸酯;以及
(C)任选的聚氨酯反应催化剂;
任选地在
(D)外用可接受的载体流体的存在下反应。
实施方案16:一种根据根据实施方案14所述的方法制备的凝胶组合物。
实施方案17:一种根据根据实施方案15所述的方法制备的凝胶组合物。
实施方案18:一种用于制备凝胶糊状物组合物的方法,所述方法包括:
(I)剪切根据实施方案1所述的凝胶组合物,以及
(II)将所剪切的聚氨酯弹性体凝胶与另外量的所述载体流体组合以形成凝胶糊状物组合物。
实施方案19:一种用于制备凝胶糊状物组合物的方法,所述方法包括:
(I)剪切根据实施方案1所述的凝胶组合物,以及
(II)将所剪切的聚氨酯弹性体凝胶与活性成分组合。
实施方案20:一种用于制备凝胶糊状物组合物的方法,所述方法包括:
(I)剪切根据实施方案6所述的凝胶组合物,以及
(II)将所剪切的聚氨酯弹性体凝胶与另外量的所述载体流体组合以形成凝胶糊状物组合物。
实施方案21:一种用于制备凝胶糊状物组合物的方法,所述方法包括:
(I)剪切根据实施方案6所述的凝胶组合物,以及
(II)将所剪切的聚氨酯弹性体凝胶与活性成分组合。
实施方案22:一种制备聚氨酯弹性体的方法,所述方法包括:
I)将多异氰酸酯反应物和多元醇反应物任选地在外用可接受的载体流体中混合以形成反应物浓度为约80%(w/w)的反应混合物,其中所述多异氰酸酯反应物包含两个或更多个异氰酸酯官能团,并且所述多元醇反应物包含两个或羟基;
II)任选地添加聚氨酯反应催化剂;以及
III)任选地将所述反应混合物加热至约80℃以形成所述聚氨酯弹性体。
实施方案23:根据实施方案22所述的方法,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体及其组合。
实施方案24:根据实施方案22所述的方法,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯、椰油辛酸酯/癸酸酯及其组合。
实施方案25:根据实施方案22所述的方法,所述方法进一步包括将药物活性成分溶解在所述外用可接受的载体流体中。
实施方案26:根据实施方案22所述的方法,其中所述多异氰酸酯反应物衍生自另一种多异氰酸酯的聚合。
实施方案27:根据实施方案22所述的方法,所述方法进一步包括由六亚甲基二异氰酸酯制备所述多异氰酸酯反应物。
实施方案28:根据实施方案22所述的方法,所述方法进一步包括由五亚甲基二异氰酸酯制备所述多异氰酸酯反应物。
实施方案29:一种通过根据实施方案18所述的方法制备的聚氨酯弹性体凝胶糊状物。
实施方案30:一种通过根据实施方案19所述的方法制备的聚氨酯弹性体凝胶糊状物。
实施方案31:一种通过根据实施方案20所述的方法制备的聚氨酯弹性体凝胶糊状物。
实施方案32:一种通过根据实施方案21所述的方法制备的聚氨酯弹性体凝胶糊状物。
实施方案33:一种外用制剂,其包含:
根据实施方案1或实施方案6所述的凝胶组合物;和药物活性成分,其中所述药物活性成分是个人护理活性成分或保健活性成分。
实施方案34:一种外用制剂,其包含:
根据实施方案29至32中任一项所述的聚氨酯弹性体凝胶糊状物;和药物活性成分,其中所述药物活性成分是个人护理活性成分或保健活性成分。
实施方案35:一种足部贴合鞋垫或鞋底,其包含根据实施方案1或实施方案6所述的凝胶组合物。
实施方案36:一种医学上可接受的医用凝胶,其包含根据实施方案1或实施方案6所述的凝胶组合物。
实施方案37:一种外用制剂,其包含根据实施方案1或实施方案6所述的凝胶组合物。
通过以下实施例进一步说明本公开文本,提供所述实施例仅是示例性的,并不限制本发明的范围。某些修改和等同物对于本领域技术人员而言应是清楚的,并且旨在包括在本公开文本的范围内。本公开文本提供了但不限于以下制剂实施例。
实施例1-用三庚酸甘油酯、椰油辛酸酯/癸酸酯和十一烷(和)十三烷制备二亚油酸/丙二醇共聚物基聚氨酯弹性体凝胶。
向反应釜中添加三庚酸甘油酯、椰油辛酸酯/癸酸酯、二亚油酸/丙二醇共聚物和五亚甲基二异氰酸酯三聚体。在室温下搅拌此混合物,直至获得澄清、均匀的溶液。在搅拌下添加新癸酸铋,并且将反应加热至60℃持续约1小时,此时形成灰白色软橡胶。在橡胶形成后,允许橡胶冷却至室温。
然后将聚氨酯弹性体橡胶置于鼓中,在高剪切混合下添加三庚酸甘油酯。然后使所得悬浮液通过分散器,并且允许所得凝胶冷却至室温。然后在混合下添加十一烷和/或十三烷,直至达到所需的粘度。
实施例2-用三庚酸甘油酯、椰油辛酸酯/癸酸酯和椰子烷烃制备二亚油酸/丙二醇共聚物基聚氨酯弹性体凝胶。
根据实施例1制备聚氨酯弹性体橡胶。通过以下方式来制备聚氨酯弹性体凝胶:将聚氨酯弹性体橡胶置于鼓中,然后在高剪切混合下添加三庚酸甘油酯。然后使所得悬浮液通过分散器,并且允许所得凝胶冷却至室温。然后在混合下添加椰子烷烃,直至达到所需的粘度。
实施例3-用三庚酸甘油酯和椰油辛酸酯/癸酸酯制备二亚油酸/丙二醇共聚物基聚氨酯弹性体凝胶。
根据实施例1制备聚氨酯弹性体橡胶。通过以下方式来制备聚氨酯弹性体凝胶:将聚氨酯弹性体橡胶置于鼓中,然后在高剪切混合下添加三庚酸甘油酯。然后使所得悬浮液通过分散器,并且允许所得凝胶冷却至室温。然后在混合下添加椰油辛酸酯/癸酸酯,直至达到所需的粘度。
实施例4-用三庚酸甘油酯制备二亚油酸/丙二醇共聚物基聚氨酯弹性体凝胶。
根据实施例1制备聚氨酯弹性体橡胶。通过以下方式来制备聚氨酯弹性体凝胶:将聚氨酯弹性体橡胶置于鼓中,然后在高剪切混合下添加三庚酸甘油酯。然后使所得悬浮液通过分散器,并且允许所得凝胶冷却至室温。然后在混合下添加三庚酸甘油酯,直至达到所需的粘度。
实施例5-蓖麻油基五亚甲基二异氰酸酯三聚体聚氨酯弹性体的制备
向罐中添加三庚酸甘油酯、蓖麻油和五亚甲基二异氰酸酯三聚体。在室温下搅拌此混合物,直至获得澄清、均匀的溶液。在搅拌下添加新癸酸铋,并且将反应加热至60℃持续约1小时,此时形成灰白色软橡胶。在橡胶形成后,允许橡胶冷却至室温。
然后将聚氨酯弹性体橡胶置于钢制容器中,并且在高剪切混合下添加三庚酸甘油酯,直至达到所需的粘度。
在某个例子中,向不锈钢反应容器中添加三庚酸甘油酯(202.0克)、蓖麻油(32.0克)、五亚甲基二异氰酸酯三聚体(15.9克)和新癸酸铋(2.5克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物。将反应混合物置于铝制容器中,并且加热至80℃持续1小时,此时形成半透明橡胶。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加三庚酸甘油酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
在另一个例子中,向4盎司玻璃罐中添加三庚酸甘油酯(41.1克)、蓖麻油(6.7克)、五亚甲基二异氰酸酯三聚体(3.31克)和新癸酸铋(0.5克)。将此混合物在室温下剧烈搅拌约10分钟,直至获得澄清、均匀的混合物。将反应混合物覆盖,并且加热至80℃持续19.5小时,此时形成半透明橡胶。50克凝胶样品的硬度为1.72N,如使用具有5千克荷重元的StableMicro Systems质构仪确定的,所述质构仪装配有TA-18B Stable Micro Systems探针并插入凝胶表面5mm。
实施例6-蓖麻油/异佛尔酮二异氰酸酯聚氨酯弹性体的制备
向不锈钢反应容器中添加琥珀酸二异辛酯(440克)、羟值为166.87mg/g的蓖麻油(71.1克)、异氰酸酯含量为37.80%的异佛尔酮二异氰酸酯(23.5克)和新癸酸铋(5.33克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品加热至75℃持续18小时,此时形成半透明凝胶。50克凝胶样品的硬度为2.85N,如使用具有5千克荷重元的Stable MicroSystems质构仪确定的,所述质构仪装配有TA-18B Stable Micro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体凝胶破碎成较小的块,置于金属容器中,并且添加十一烯酸庚酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
在某个例子中,向玻璃反应容器中添加三庚酸甘油酯(293.5克)、羟值为166.87mg/g的蓖麻油(87.9克)、异氰酸酯含量为37.80%的异佛尔酮二异氰酸酯(29.0克)和新癸酸铋(8.9克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品覆盖,并且加热至75℃持续19.5小时,此时形成半透明橡胶。50克凝胶样品的硬度为3.69N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18B StableMicro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加三庚酸甘油酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
实施例7-二亚油酸/丙二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的制备
向塑料反应容器中添加十一烯酸庚酯(1959.2g(克))、羟值为56mg/g的二亚油酸/丙二醇共聚物(410.0克)、异氰酸酯含量为22.77%的六亚甲基二异氰酸酯三聚体(70.0克)和新癸酸铋(10.0克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品覆盖,并且在25℃下放置25小时,此时形成半透明橡胶。50克凝胶样品的硬度为3.14N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18B StableMicro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加十一烯酸庚酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
实施例8-二亚油酸/丙二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的制备
向不锈钢反应容器中添加椰油辛酸酯/癸酸酯(445.0克)、二亚油酸/丙二醇共聚物(87.5克)、五亚甲基二异氰酸酯三聚体(20.6克)和新癸酸铋(3.2克)。将此混合物在室温下剧烈搅拌约10分钟,直至获得澄清、均匀的混合物。将反应混合物加热至80℃持续1小时,此时形成半透明橡胶。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加椰油辛酸酯/癸酸酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
在某个例子中,向4盎司玻璃罐中添加椰油辛酸酯/癸酸酯(39.5克)、羟值为56mg/g的二亚油酸/丙二醇共聚物(7.8克)、异氰酸酯含量为23.5%的五亚甲基二异氰酸酯三聚体(1.8克)和新癸酸铋(0.3克)。将此混合物在室温下剧烈搅拌约10分钟,直至获得澄清、均匀的混合物。将反应混合物覆盖,并且加热至80℃持续19.5小时,此时形成半透明橡胶。50克凝胶样品的硬度为7.12N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18B Stable Micro Systems探针并插入凝胶表面5mm。
实施例9-蓖麻油基六亚甲基二异氰酸酯三聚体弹性体的制备
向塑料反应容器中添加三庚酸甘油酯(2354.7克)、蓖麻油(373.0克)、异氰酸酯含量为22.77%的六亚甲基二异氰酸酯三聚体(188.6克)和新癸酸铋(27.0克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品覆盖,并且在室温下放置20小时,此时形成半透明橡胶。50克凝胶样品的硬度为2.72N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18B Stable Micro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加三庚酸甘油酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
实施例10-二亚油酸/二亚油酸二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的制备
向玻璃反应容器中添加椰油辛酸酯/癸酸酯(826.3g(克))、羟值为56mg/g的二亚油酸/二亚油酸二醇共聚物(172.8克)、异氰酸酯含量为22.77%的六亚甲基二异氰酸酯三聚体(29.5克)和新癸酸铋(4.23克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品覆盖,并且加热至75℃持续17小时,此时形成半透明橡胶。50克凝胶样品的硬度为4.51N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18B Stable Micro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加椰油辛酸酯/癸酸酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
实施例11-二亚油酸/二亚油酸二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的制备
向玻璃反应容器中添加椰油辛酸酯/癸酸酯(231.6g(克))、羟值为56mg/g的二亚油酸/二亚油酸二醇共聚物(49.0克)、异氰酸酯含量为23.5%的五亚甲基二异氰酸酯三聚体(7.7克)和新癸酸铋(1.2克)。将此混合物在室温下剧烈搅拌约20分钟,直至获得澄清、均匀的混合物,并且将50克的混合物倒入4盎司玻璃罐中。将剩余的反应混合物和50克样品覆盖,并且加热至80℃持续19.5小时,此时形成半透明橡胶。50克凝胶样品的硬度为0.49N,如使用具有5千克荷重元的Stable Micro Systems质构仪确定的,所述质构仪装配有TA-18BStable Micro Systems探针并插入凝胶表面5mm。
然后将聚氨酯弹性体橡胶破碎成较小的块,置于金属容器中,并且添加椰油辛酸酯/癸酸酯,然后使用具有30mm直径转子、方孔高剪切筛且在4500至8000转/分钟下操作的Silverson L5M-A均化器均化为具有所需粘度的光滑凝胶糊状物。
实施例12-聚氨酯弹性体的配制
为了探索将本文所述的聚氨酯弹性体配制为外用制剂的能力,进行以下实验。
下表1提供了本说明书的示例性聚氨酯弹性体(“生物弹性体”)以及比较弹性体。表1中的组成省略了生物弹性体A和C的异氰酸酯交联剂,其为六亚甲基二异氰酸酯三聚体。对于生物弹性体D,IPDI是异佛尔酮二异氰酸酯。
表1:所检查的弹性体
将上述生物弹性体添加到以下常见外用载体中,以确定它们配制成外用制剂的能力。
在图1中,利用5至1的评分系统,其中得分“5”表示硬凝胶,得分“1”表示可流动凝胶。在所研究的量下,本文所述的生物弹性体显示出与以下物质的良好相容性:脂肪醇>甘油三酯>酯;与烃的较小相容性;并且与有机硅无相容性。
然后将这三种生物弹性体与不同的防晒剂组合以检查它们与活性剂的相容性以及它们用作配制剂的能力。表2-4描述了这三种所述的生物弹性体的结果。
表2:在10%固体下的生物弹性体A
表3:在9%固体下的生物弹性体C
表4:在10%固体下的生物弹性体D
这些实验的结果表明,本文所述的生物弹性体与有机和物理防晒剂高度相容,并且不会不利地影响最终制剂的透明度。
然后如下在水包油乳液和油包水乳液两者中评价生物弹性体的加工性。
表5:5%弹性体凝胶在油包水(W/O)乳液中的加工性
研究以下每种弹性体凝胶*:生物弹性体A;生物弹性体C;生物弹性体D;VelvesilDM凝胶;和Dowsil 9040。将所有弹性体凝胶作为与辛基聚甲基硅氧烷的预混物添加到制剂的油相(B)中。在添加前将预混物均化。在预混物中可见弹性体的小颗粒,但是在产物中不可见。在高混合下将相A非常缓慢地添加到相B中(冷制法,标准w/Si乳液制备)。在任何弹性体凝胶在w/o乳液中的加工性期间没有观察到重大差异,这证实本文所述的生物弹性体可以容易地在油包水乳液中加工。
如下研究弹性体凝胶在水包油乳液中的加工性:
表6:2.5%弹性体凝胶在水包油(O/W)乳液中的加工性
研究以下每种弹性体凝胶*:对照-无弹性体;生物弹性体C;生物弹性体D;生物弹性体A;Velvesil DM 6;和DM 9040。将水相(A)和油相(B)分别加热至70℃,然后混合并均化。在50℃下,添加卡波姆的预混物,混合并中和。生物弹性体C和D需要预混,但是生物弹性体Velvesil DM 6和DM 9040不需要预混。实验结果表明,易加工性从最大到最小为Velvesil DM>DC 9040>生物弹性体A>生物弹性体C~生物弹性体D。
还评价弹性体的感官(皮肤感觉)特征。结果显示如下:对照-“平坦”感觉,没有缓冲;生物弹性体C-提供光滑的缓冲感觉,湿润且不干燥。皮肤是柔软的;生物弹性体D-有点光泽和光滑,手感光滑,有弹性和缓冲;生物弹性体A-在C与D之间;Velvesil DM-粉末状和干燥的缓冲感觉,有消光效果;Dowsil 9040-粉末状但有弹性的缓冲,没有Velvesil DM干燥,提供消光效果。
还评价弹性体制剂的以下内容:流变学:生物弹性体的剪切稀化行为;易生产性:使用Ross混合器和在线均化器在润肤剂中制备一千克的生物弹性体并评价剪切敏感性。
实施例13-聚氨酯弹性体的傅立叶变换红外光谱
进行傅立叶变换红外光谱术(FTIR)以分析聚氨酯弹性体的分子结构。
二亚油酸/丙二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图1中。
二亚油酸/丙二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图2中。
蓖麻油基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图3中。
蓖麻油基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图4中。
二亚油酸/二亚油酸二醇共聚物基五亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图5中。
二亚油酸/二亚油酸二醇共聚物基六亚甲基二异氰酸酯三聚体弹性体的FTIR光谱图示于图6中。
蓖麻油基异佛尔酮二异氰酸酯三聚体弹性体的FTIR光谱图示于图7中。
Claims (37)
1.一种包含聚氨酯弹性体凝胶的凝胶组合物,所述聚氨酯弹性体凝胶由以下物质的反应制备:
(A)包含两个或更多个异氰酸酯官能团的多异氰酸酯或多异氰酸酯混合物;
(B)包含两个或更多个羟基、胺、硫醇或羧酸官能团的多元醇或多元醇混合物;
(C)任选的聚氨酯反应催化剂;以及
(D)任选的外用可接受的载体流体。
2.根据权利要求1所述的凝胶组合物,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体、油及其组合。
3.根据权利要求1所述的凝胶组合物,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯、椰油辛酸酯/癸酸酯、三庚酸甘油酯、辛酸/癸酸甘油三酯、十二烷、十三烷、C13-15烷烃、角鲨烯、角鲨烯、月桂酸异戊酯(isoamyllaurate)、月桂酸异戊酯(isopentyl laurate)、辛酸/癸酸/肉豆蔻酸/硬脂酸甘油三酯、辛酸/癸酸/琥珀酸甘油三酯、肉豆蔻酸异丙酯、荷荷巴酯、三辛酸甘油酯和棕榈油。
4.根据权利要求1所述的凝胶组合物,其进一步包含溶解在所述外用可接受的载体流体中的药物活性成分。
5.根据权利要求1所述的凝胶组合物,其中所述多异氰酸酯或多异氰酸酯混合物是低分子量多异氰酸酯或多异氰酸酯混合物,并且其中所述多元醇或多元醇混合物含有两个或更多个羟基、胺、硫醇或羧酸基团。
6.一种包含聚氨酯弹性体的凝胶组合物,所述聚氨酯弹性体来自以下物质的反应:
(A)蓖麻油;
(B)异佛尔酮二异氰酸酯,其中异氰酸酯基团与羟基的摩尔比在1:1与1:2之间;
(C)任选的聚氨酯反应催化剂;以及
(D)浓度为所述凝胶组合物的60%(w/w)至99.9%(w/w)的任选的外用可接受的载体流体;
其中通过在形成所述聚氨酯弹性体凝胶期间将个人护理或保健活性成分溶解在所述外用可接受的溶剂中,或者通过将所述个人护理或保健活性成分与形成的聚氨酯弹性体凝胶混合,将所述个人护理或保健活性成分任选地掺入所述聚氨酯弹性体凝胶中。
7.根据权利要求6所述的凝胶组合物,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体及其组合。
8.根据权利要求6所述的凝胶组合物,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯和椰油辛酸酯/癸酸酯。
9.根据权利要求6所述的凝胶组合物,其进一步包含溶解在所述外用可接受的载体流体中的药物活性成分。
10.根据权利要求1所述的凝胶组合物,其中所述聚氨酯催化剂是含铋基团的催化剂。
11.根据权利要求6所述的凝胶组合物,其中所述聚氨酯催化剂是含铋基团的催化剂。
12.根据权利要求1所述的凝胶组合物,其中所述外用可接受的溶剂的大于50%的碳含量衍生自植物来源。
13.根据权利要求6所述的凝胶组合物,其中所述外用可接受的溶剂的大于50%的碳含量衍生自植物来源。
14.一种用于制备根据权利要求1所述的凝胶组合物的方法,所述方法包括使以下物质:
(A)多元醇;
(B)异佛尔酮二异氰酸酯;以及
(C)任选的聚氨酯反应催化剂;
任选地在
(D)外用可接受的载体流体的存在下反应。
15.一种用于制备根据权利要求6所述的凝胶组合物的方法,所述方法包括使以下物质:
(A)蓖麻油;
(B)异佛尔酮二异氰酸酯;以及
(C)任选的聚氨酯反应催化剂;
任选地在
(D)外用可接受的载体流体的存在下反应。
16.一种根据根据权利要求14所述的方法制备的凝胶组合物。
17.一种根据根据权利要求15所述的方法制备的凝胶组合物。
18.一种用于制备凝胶糊状物组合物的方法,所述方法包括:
I)剪切根据权利要求1所述的凝胶组合物,以及
II)将所剪切的聚氨酯弹性体凝胶与另外量的所述载体流体组合以形成凝胶糊状物组合物。
19.一种用于制备凝胶糊状物组合物的方法,所述方法包括:
I)剪切根据权利要求1所述的凝胶组合物,以及
II)将所剪切的聚氨酯弹性体凝胶与活性成分组合。
20.一种用于制备凝胶糊状物组合物的方法,所述方法包括:
I)剪切根据权利要求6所述的凝胶组合物,以及
II)将所剪切的聚氨酯弹性体凝胶与另外量的所述载体流体组合以形成凝胶糊状物组合物。
21.一种用于制备凝胶糊状物组合物的方法,所述方法包括:
I)剪切根据权利要求6所述的凝胶组合物,以及
II)将所剪切的聚氨酯弹性体凝胶与活性成分组合。
22.一种制备聚氨酯弹性体的方法,所述方法包括:
I)将多异氰酸酯反应物和多元醇反应物任选地在外用可接受的载体流体中混合以形成反应物浓度为约80%(w/w)的反应混合物,其中所述多异氰酸酯反应物包含两个或更多个异氰酸酯官能团,并且所述多元醇反应物包含两个或羟基;
II)任选地添加聚氨酯反应催化剂;以及
III)任选地将所述反应混合物加热至约80℃以形成所述聚氨酯弹性体。
23.根据权利要求22所述的方法,其中所述外用可接受的载体流体选自酯、甘油三酯、烃、有机硅流体及其组合。
24.根据权利要求22所述的方法,其中所述外用可接受的载体流体选自琥珀酸二异辛酯、十一烯酸庚酯、新戊二醇二庚酸酯、椰油辛酸酯/癸酸酯及其组合。
25.根据权利要求22所述的方法,所述方法进一步包括将药物活性成分溶解在所述外用可接受的载体流体中。
26.根据权利要求22所述的方法,其中所述多异氰酸酯反应物衍生自另一种多异氰酸酯的聚合。
27.根据权利要求22所述的方法,所述方法进一步包括由六亚甲基二异氰酸酯制备所述多异氰酸酯反应物。
28.根据权利要求22所述的方法,所述方法进一步包括由五亚甲基二异氰酸酯制备所述多异氰酸酯反应物。
29.一种通过根据权利要求18所述的方法制备的聚氨酯弹性体凝胶糊状物。
30.一种通过根据权利要求19所述的方法制备的聚氨酯弹性体凝胶糊状物。
31.一种通过根据权利要求20所述的方法制备的聚氨酯弹性体凝胶糊状物。
32.一种通过根据权利要求21所述的方法制备的聚氨酯弹性体凝胶糊状物。
33.一种外用制剂,其包含:
根据权利要求1或权利要求6所述的凝胶组合物;和药物活性成分,其中所述药物活性成分是个人护理活性成分或保健活性成分。
34.一种外用制剂,其包含:
根据权利要求29至32中任一项所述的聚氨酯弹性体凝胶糊状物;和药物活性成分,其中所述药物活性成分是个人护理活性成分或保健活性成分。
35.一种足部贴合鞋垫或鞋底,其包含根据权利要求1或权利要求6所述的凝胶组合物。
36.一种医学上可接受的医用凝胶,其包含根据权利要求1或权利要求6所述的凝胶组合物。
37.一种外用制剂,其包含根据权利要求1或权利要求6所述的凝胶组合物。
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WO2021231527A1 (en) * | 2020-05-12 | 2021-11-18 | Nanometics Llc (D.B.A. Phd Biosciences) | Non-isocyanate polyurethane elastomers and compositions comprising such elastomers |
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