CN102030615A - 4-己基间苯二酚的高透明度水性浓缩物 - Google Patents
4-己基间苯二酚的高透明度水性浓缩物 Download PDFInfo
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Abstract
本发明涉及己基间苯二酚/水的浓缩物，其透明度高、易处理，并且易于与其他成分共混以形成皮肤护理组合物。
Description
技术领域
本发明涉及4-己基间苯二酚的水性浓缩物，其透明度高、易处理，并且易于与其他成分共混以制备个人护理组合物、消费者用组合物和家用组合物。
背景技术
4-己基间苯二酚是一种已被描述为外用以亮白肌肤、用于口服抗菌锭剂以及其他用途的化合物。然而，4-己基间苯二酚已被描述并被公认为是“水不溶物”。因此，结合水来配制4-己基间苯二酚相当受限。通常，用水配制4-己基间苯二酚涉及(例如)在诸如乙氧基乙二醇的二醇中预混合4-己基间苯二酚，并通过添加各种其他成分(包括水)将此混合物稀释成低浓度的4-己基间苯二酚。该方法可能还涉及加热。
然而，现已发现可以制备4-己基间苯二酚与水的混合物，特别是具有高浓度4-己基间苯二酚的混合物。此类混合物可以(例如)用于将4-己基间苯二酚递送至制剂，而无需使用其他溶剂、增溶剂等。具体地讲，包含约64重量％至约80重量％的4-己基间苯二酚的水性浓缩物易于处理，并且用于制备各种制剂和组合物。有利地，此类水性浓缩物具有极高的透明度。
发明内容
在一个方面，本发明提供一种包含约64重量％至约80重量％的4-己基间苯二酚和水的4-己基间苯二酚水性浓缩物，其中该水性浓缩物具有高透明度。
本发明还提供一种包含4-己基间苯二酚和水的4-己基间苯二酚水性浓缩物，其中4-己基间苯二酚和水以约1.7至约4的重量比浓度存在，并且其中该浓缩物具有高透明度。
本发明还提供一种制备组合物的方法，其包括：将高透明度4-己基间苯二酚水性浓缩物与第二组合物混合，其中该水性浓缩物包含(i)约64重量％至约80重量％的4-己基间苯二酚和(ii)水；并且第二组合物包含选自山疏水剂、表面张力抑制剂、芳香剂及其组合组成的组中的成分。
本发明还提供一种制备组合物的方法，其包括：将高透明度4-己基间苯二酚水性浓缩物与第二组合物混合，其中该水性浓缩物包含4-己基间苯二酚和水，并且4-己基间苯二酚和水以约1.7至约4的重量比浓度存在，并且第二组合物包含选自由疏水剂、表面张力抑制剂、芳香剂及其组合组成的组的成分。
本发明还提供一种组合物，其包含：高透明度4-己基间苯二酚水性浓缩物，其包含(i)约64重量％至约80重量％的4-己基间苯二酚和(ii)水；和第二组合物，其包含选自由疏水剂、表面张力抑制剂、芳香剂及其组合组成的组的成分。
通过本发明的具体实施方式和权利要求书，本发明的其他特征和优点将显而易见。
具体实施方式
据信根据本文的描述，本领域的技术人员可最大限度地利用本发明。下面的具体实施例应该理解为仅仅是示例性的，并且无论如何都不会以任何方式限制本公开的其余部分。
除非另有定义，否则本文使用的所有科技术语的含义与本发明所属领域的普通技术人员通常所理解的含义相同。另外，将本文提及的所有出版物、专利中请、专利及其他参考文献以引用方式并入本文中。除非另外指明，否则用于表示成分浓度的百分比为重量百分比(即，％(W/W))。相似地，用于表示成分相对比例的浓度比也采用重量百分比来确定(即，通过将一种成分与另一种成分的重量百分比相除来计算浓度比)。除非另外规定，否则所有范围均包括端值，如“4至9”包括端值4和9。
本文所用的“基本上不含”是指以小于约1％、优选地小于约0.5％、更优选地小于约0.1％的浓度存在，最优选地为完全不存在。
本文所用的“产品”任选地为成品包装的形式。在一个实施例中，包装为容纳组合物的容器，例如塑料、金属或玻璃管或广口瓶。该产品还可以包含其他包装，例如用于储存此类容器的塑料或纸板箱。在一个实施例中，该产品包括本发明的组合物，并且包含指导用户将该组合物施用到皮肤或毛发上的说明书。
本文所用的“外用”是指(例如)通过使用手或诸如试巾、滚筒或喷雾器的涂敷器直接涂于或敷于外部皮肤、头皮或毛发上。
本文所用的“美容上可接受的”是指该术语所描述的成分适用于接触组织(例如皮肤或毛发)而无不适当的毒性、不相容性、不稳定性、刺激性、变应性反应等。
在某些实施例中，本发明的水性浓缩物和组合物适于治疗皮肤老化迹象。本文所用的“皮肤老化迹象”包括细纹和皱纹、弹性损失、皮肤不平以及红疤的存在。在特别优选的实施例中，老化迹象是存在细纹和皱纹和/或弹性损失。
本文所用的“治疗皮肤老化迹象”是指缓和、减轻、预防、改善或消除上述皮肤老化的存在或迹象。
本文所用的“皱纹”包括微细纹、微皱纹或粗皱纹。皱纹的实例包括但不限于眼睛周围的微细纹(例如“鱼尾纹”)、前额和颊皱纹、眉心纹和嘴巴周围的笑纹。
本文所用的“弹性损失”包括皮肤或组织的弹性或结构完整性的损大，包括但不限于松垂、松弛和松散组织。弹性或组织结构完整性的损失可由多种因素所致，包括但不限于疾病、衰老、激素变化、机械创伤、环境损害，或者是向组织施用诸如美容品或药物的产品的结果。
本文所用的“皮肤不平”是指与弥漫性或斑驳性色素沉着有关的皮肤状况，所述色素沉着可分类为色素沉着过度，如发炎后色素沉着过度。
本文所用的“红疤”是指与发红或红斑有关的皮肤状况。
本文所用的“美容品”指能保持、恢复、赋予、刺激或增强体美外观或者似乎能增进美貌或年轻的美容物质或制品，具体地涉及到组织或皮肤的外观。
本文所用的“美容上有效量”是指足以治疗一种或多种皮肤老化迹象、但充分低以避免严重副作用的生理活性化合物或组合物的量。化合物或组合物的美容上有效量要随以下因素而变：所治疗的具体病症、最终用户的年龄和身体状况、所治疗/预防的病症的严重程度、治疗的持续时间、其他治疗的性质、所采用的具体化合物或产品/组合物、所具体采用的美容上可接受的载体等等。
4-己基间苯二酚与水的高透明度浓缩物
4-己基间苯二酚(“4-HR”)为具有以下结构的二羟基酚化合物：
4-HR可以通过本领域中已知的方法制备。合适方法的例子描述于美国专利申请公开No.2006/0129002中，该专利全文引入本文以供参考。4-HR可以(例如)“SYNOVEA HR”从新泽西州(NJ)的Sytheon of Lincoln Park商购获得。
4-HR在现有技术中被描述为水不溶物。然而，发明人已发现虽然4-HR在整个大部分可能的浓度/与水的混合比例下明显不溶于水，但是颇为意外的是存在特定的“相容性窗”，在该相容性窗中4-HR与水形成高透明度混合物。
因此，在本发明的一个实施例中，高透明度4-己基间苯二酚水性浓缩物包含约64重量％至约80重量％的4-HR。
水性浓缩物的剩余部分优选地包含水。浓缩物中水的重量百分比可以为约1％至约36％、优选地为约16％至约36％、最优选地为约20％至约36％。
在本发明的另一方面，高透明度4-己基间苯二酚水性浓缩物包含4-己基间苯二酚和水，其中4-己基间苯二酚和水以约1.7至约4的重量比浓度存在。
在某些实施例中，水性浓缩物包含约64重量％至约80重量％的4-HR，并且剩余部分基本上由水组成，即，剩余部分由水和一种或多种不妨碍或减弱浓缩物高透明度特征的附加成分组成。
在一个实施例中，此类附加成分限于：(1)低浓度离子盐(例如Na、K、Cl、Ca、Mg、Zn等的盐)，其总共以小于约0.1重量％的浓缩物的浓度存在，和/或(2)诸如4-己基苯-1，3-二醇的含酚化合物和通常以杂质存在于4-HR中的其他物质，两者总共以小于约3重量％、优选地小于2重量％、优选地小于约1重量％、最优选地小于约0.5重量％的浓缩物的浓度存在。
在某些其他实施例中，附加成分包括一种或多种生物活性成分，这些成分可以(例如)溶于4-HR。合适的生物活性成分的例子包括水杨酸、有机防晒剂和类视色素。
附加成分优选地总共以小于约20重量％、优选地小于约10重量％、更优选地小于约5重量％、甚至更优选地小于约3重量％、最优选地小于约1重量％的水性浓缩物的浓度存在。
在某些实施例中，附加成分总共以4-HR与附加成分的重量比为至少约3.2∶1、优选地至少约6∶1、更优选地至少约12∶1、更优选地至少约20∶1、最优选至少约30∶1的浓度存在于浓缩物中。
该水性浓缩物具有高透明度。在一个实施例中，该水性浓缩物透射至少25％(优选地至少50％、更优选地至少70％)的光，该光具有通过1cm路径长度的700nm的波长。对于距离12英寸处的一般观察者而言，当将该水性浓缩物置于(例如)常规的100mL透明塑料容器中时，其看起来是透光的，并且一般无任何可见层。
透明度可以采用设为700nm的紫外可见分光光度计来测试。使样品在室温下平衡至少约24小时后，将其置于测试单元(1cm比色杯)中，并且采用紫外可见分光光度计测量透射百分率。
由于该水性浓缩物具有高透明度，因此无需添加成分来增加透明度。例如，在某些实施例中，该水性浓缩物基本上不含相容剂，即，使疏水性成分与亲水性成分相容的成分。具体地讲，在某些实施例中，该水性浓缩物基本上不含以下相容剂中的一种、多种或全部：表面张力抑制剂(表面活性剂和乳化剂)、C2-C6醇(诸如乙醇和异丙醇的脂肪醇)、二醇(即，具有不止一个羟基并且各羟基均附接到不同碳原子上的化合物；如甘油、包括丙二醇或丁二醇在内的二醇)；乙二醇醚(如，二甘醇一乙基醚)；以及诸如二甲苯磺酸钠或异丙基苯磺酸钠的水溶助长剂。
可通过使用磁力搅拌棒、螺旋桨式搅拌器等在室温下混合水、4-HR以及不减弱水性浓缩物高透明度的任选的附加成分来制备该水性浓缩物。添加顺序并不重要。在某些实施例中，将4-HR和水混合在一起后添加附加成分。
使用方法
该高透明度4-HR水性浓缩物可用于制备组合物，诸如用于保健、个人护理、美容、医药或家居产品用途的产品用组合物。
根据本发明的另一个方面，提供一种制备组合物的方法，该方法包括将高透明度4-己基间苯二酚水性浓缩物与第二组合物混合，其中水性浓缩物包含(i)约64重量％至约80重量％的4-己基间苯二酚和(ii)水；并且第二组合物包含选自由疏水剂、表面张力抑制剂、芳香剂及其组合组成的组。
作为另外一种选择，可以将高透明度4-己基间苯二酚水性浓缩物与第二组合物混合，其中水性浓缩物包含以约1.7至约4的重量比浓度存在的4-己基间苯二酚和水；并且第二组合物包含选自由疏水剂、表面张力抑制剂、芳香剂及其组合组成的组。
第二组合物包含一种或多种成分，这些成分与水性浓缩物混合时增强了该组合物用于一种或多种产品用途的特性，例如使其在美容上更可接受、在药学上更可接受、更适于生物递送、更具表面活性、更美观、更方便等。
第二组合物可以包括一种或多种以下成分，特别是适于美容品、医药或家居产品的那些成分：疏水剂、二醇、表面张力抑制剂、C2-C6醇、芳香剂及其组合。在某些优选的实施例中，第二组合物包括一种或多种疏水剂、表面张力抑制剂和/或芳香剂。
合适的疏水剂包括那些适用于美容产品的烃类，诸如具有支链或直链、饱和或不饱和的约C7至约C50、更优选地约C8至约C22的碳链的那些烃，例如油类、脂肪脂、脂肪醇、蜡或适于提供润肤性、铺展性或相稳定性的有机硅。在一个实施例中，疏水剂不适于作为如下所述的表面张力抑制剂。
合适的二醇包括能够提供保湿性的那些，诸如相对于适于作为相容剂的二醇在上文举例说明的那些。合适的C2-C6醇包括适于提供溶解性或铺展性的那些，也包括作为相容剂而在上文举例说明的那些。合适的芳香剂包括挥发性醛、酯等的芳香混合物，包括常用于保健、个人护理、美容品、医药或家居产品的那些。
合适的表面张力抑制剂包括能够减小表面张力、提供乳化作用、增加或减少泡沫、增强清洁性或去污力等的多种表面活性剂中的任何一种。在一个实施例中，当表面张力抑制剂以小于0.5％的浓度与纯去离子水混合时，其能够将去离子水的表面张力减小至小于约45达因/厘米。
第二组合物可以具有常用于保健、个人护理、美容品、医约或家居产品的附加成分，例如染料、螯合剂、分散剂、美容或药物活性剂等。用于第二组合物的美容或药物活性剂的非限制性实例包括抗痤疮剂、抗微生物剂、抗炎剂、抗真菌剂、抗寄生虫剂、抗寄生虫剂、外用止痛剂、防晒剂、光保护剂、抗氧化剂、角质层分离剂、维生素、抗汗剂、除臭剂、皮肤(脱色素)色素沉着剂、抗老化/抗皱剂和pH调节剂、防腐剂以及抗氧化剂。这些活性剂可以美容上有效量存在或者以适于提供合适的生物效应的量存在。
可以将4-HR的高透明度水性浓缩物与足量的第二组合物混合以制备配制的组合物，该组合物适用于保健、个人护理、美容品、医药或家居领域。
在一个实施例中，将该水性浓缩物(单独或任选地与第二组合物混合后)施用到基底(例如可用于擦拭皮肤或毛发的基底)上。基底可以包括无纺布，例如个人护理拭巾领域中已知的那些。
包含该水性浓缩物的组合物可为单相或多相体系，如溶液、分散体、乳状液(O/W、W/O等)、微乳液、脂质体体系或凝胶，包括洗液、霜膏、凝胶、棒状物、喷雾剂、油膏剂中的任何一种。
该组合物可使用本领域中已知的任何方法制备。
此外，在一个实施例中，组合物可以外用，即施用到需要治疗一种或多种皮肤老化迹象、粉刺或其他皮肤状况的哺乳动物的皮肤上。
可以根据合适的治疗方案(如每月、每周、每隔一天、每天、一天两次等)将该组合物施用到皮肤上。
据信根据本文的描述，本领域的技术人员可最大限度地利用本发明。下面的具体实施例应该理解为仅仅是示例性的，并且无论如何都不会以任何方式限制本公开的其余部分。以下非限制性实例将进一步说明本发明。
实例I
将4-HR(得自新泽西州(NJ)的Sytheon of Lincoln Park的“SYNOVEA HR”)与水以不同的浓度混合。使样品处于环境条件下约7天，然后按如下进行目视检测和透光率试验。
首先，记录各样品的外观。然后通过轻微摇动来搅拌样品，以得到各混合物的代表性透射百分率。约30秒后结束搅拌，将各样品置于透射百分率设为700nm波长的紫外可见分光光度计(Agilent 8453，得自加利福尼亚州圣克拉拉(Santa Clara，California)的Agilent technologies)的1cm的比色杯中。
下表1中示出了目视分析和透光率试验的结果。
表1
结果显示，虽然现有技术将4-HR描述为水不溶物，但是就包含64％-80％的4-HR(4-HR与水的重量比为1.78至4)的4-HR/水混合物而言，存在意外的相容性。
实例II
将4-辛基间苯二酚和3-甲氧基苯酚(得自密苏里州圣路易斯市(St.Louis，Missouri)的Sigma-Aldrich)分别以50％和75％的浓度与水混合。无混合物透光，并且所有示出的“层状物”均类似于比较例C3(上文)中所观察到的。
实例III
采用表2示出的成分来制备根据本发明的以下组合物。
表2
如下制备组合物：
1.将水加入主混合容器中并打开搅拌器。
2.将PEMULEN TR-1聚合物撒入混合容器中，并将这些成分混合至完全分散为止(15-20分钟)。
3.制备水、EDTA和透明质酸的预混物。将EDETA BD加入单独烧杯中的水中并混合至完全溶解。添加透明质酸预混物，并将这些成分混合至均匀为止(30分钟)。
4.将甘油加入水相并混合至均匀为止。
5.然后将混合物加热到70℃至75℃。
6.添加Olivem 1000；然后将这些成分混合5分钟，然后开始冷却至60℃至65℃。
7.在60℃至65℃下添加ARISTOFLEX AVC，并将这些成分混合至完全分散为止(20分钟)。将温度保持在60℃至65℃。
8.添加氢氧化钠(10％的溶液)以中和水相。
9.开始冷却至60℃以下。
10.当冷却至60℃后，添加道康宁200 50cst，并将这些成分混合至均匀为止。
11.将道康宁345加入水相中并混合10分钟。
12.添加道康宁1403流体并混合15分钟直到均匀为止。
13.当冷却至35℃后，依次添加下列物质：NEOLONE MxP、马齿苋提取物、PRODEW 300、α-红没药醇、水、EDTA；透明质酸预混物(步骤3)、Sepitonic M3和海藻粘多糖体。将所得混合物混合至均匀为止。
14.确保无团块后，添加预混有丁二醇(第7项)的干燥flopure(第6项)。
15.然后添加预混有芳香剂的Net-DG，然后将这些成分混合至均匀为止。
16.在单独的容器中，将75％的4-HR与水混合以形成高透明度水性浓缩物，然后将其加入其他成分中。
17.然后将所得组合物匀化3分钟。
实例IV
针对人类表皮等同物上的局部抗炎活性评估实例III的组合物。作为包含正常人表皮角质细胞的多层分化表皮的表皮等同物(EPI 200 HCF)购自马萨诸塞州阿什兰(Ashland，MA)的MatTek。收到以后，所述表皮等同物在没有氢化可的松的维持介质中在37℃下温育24小时。用实例III的组合物对等同物局部处理(2mg/cm2)2小时，然后暴露在100ng/mL的肿瘤坏死因子-α(TNFα，Sigma-Aldrich of St.Louis，MO)下。用维持介质将等同物在37℃下温育24小时。使用市售试剂盒(Upstate Biotechnology，Charlottesville，VA)分析上清液的IL-8细胞因子释放。结果示出于表3中。
表3
| 处理 | 皮肤发炎抑制百分比 |
| 安慰剂 | 14.88 |
| 实例III组合物 | 77.89** |
**经使用显著性水平设为P＜0.05的学生t-检验处理，表明与经处理的安慰剂有显著差异。
实例III的组合物显著地减轻了炎症。
Claims (6)
1.一种4-己基间苯二酚的水性浓缩物，其包含：
约64重量％至约80重量％的4-己基间苯二酚；和
水，
其中所述水性浓缩物具有高透明度。
2.根据权利要求1所述的水性浓缩物，其中所述水性浓缩物透射至少25％的光，所述光具有通过1cm路径长度的700nm的波长。
3.根据权利要求1所述的水性浓缩物，其包含约20重量％至约36重量％的水。
4.根据权利要求1所述的水性浓缩物，其主要由4-己基间苯二酚和水组成。
5.一种4-己基间苯二酚水性浓缩物，其包含：
4-己基间苯二酚；和
水，
其中所述4-己基间苯二酚和水以约1.7至约4的重量比浓度存在，并且其中所述组合物具有高透明度。
6.一种组合物，其包含：
高透明度4-己基间苯二酚水性浓缩物，其包含(i)约64重量％至约80重量％的4-己基间苯二酚和(ii)水；以及
第二组合物，其包含选自由疏水剂、表面张力抑制剂、芳香剂及其组合组成的组的成分。
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| US12/572,377 | 2009-10-02 | ||
| US12/572,377 US8084504B2 (en) | 2009-10-02 | 2009-10-02 | High-clarity aqueous concentrates of 4-hexylresorcinol |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2316412A3 (en) | 2013-03-20 |
| US20120064149A1 (en) | 2012-03-15 |
| BRPI1003846A2 (pt) | 2013-02-13 |
| CA2716184C (en) | 2017-06-27 |
| KR20110036687A (ko) | 2011-04-08 |
| CA2716184A1 (en) | 2011-04-02 |
| ES2612939T3 (es) | 2017-05-19 |
| US8084504B2 (en) | 2011-12-27 |
| CN102030615B (zh) | 2015-09-23 |
| US20130171219A1 (en) | 2013-07-04 |
| EP2316412A2 (en) | 2011-05-04 |
| US9370474B2 (en) | 2016-06-21 |
| KR101817490B1 (ko) | 2018-01-11 |
| EP2316412B1 (en) | 2016-11-23 |
| US20110082217A1 (en) | 2011-04-07 |
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