CN107635540B - 作为化妆品原料和涂层化妆品粉末的烷氧基硅烷化合物及其相关缩合产品 - Google Patents
作为化妆品原料和涂层化妆品粉末的烷氧基硅烷化合物及其相关缩合产品 Download PDFInfo
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- CN107635540B CN107635540B CN201680027868.8A CN201680027868A CN107635540B CN 107635540 B CN107635540 B CN 107635540B CN 201680027868 A CN201680027868 A CN 201680027868A CN 107635540 B CN107635540 B CN 107635540B
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- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
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- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
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- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 1
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- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
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- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- Veterinary Medicine (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
本发明描述了烷氧基硅烷化合物和相关缩合产物作为化妆品原料和用于涂层化妆品粉末；这种化合物和缩合产物的合成方法以及涂层的化妆品粉末的生产。所述化妆粉可用于制备化妆品，如面部/眼部/嘴唇的无水产品、化妆笔和面部/眼部的乳液。
Description
本发明涉及作为化妆品原料和用于涂敷化妆品粉末的烷氧基硅烷化合物和相关的缩合产物。
美容产品通过改变皮肤的光学特性并赋予其所需的外观(装饰、皱纹遮盖、肤色晚间效果、缺陷遮盖，例如色斑和病理或生理性皮肤损伤)而改善皮肤的外观。
这些光学修饰通过借助于施用的化妆品材料层来改变由使用者的皮肤引起的光吸收和/或散射，这取决于所使用以分散液、洗液、乳液或粉末的形式出现的配方。
在装饰性化妆品中考虑的大多数情况下，这种光学改性是通过着色粉末(颜料和/或珍珠)与白色粉末(实际上透明的，如赋形剂和触感改性剂)组合获得的。
通过化妆品配方施用的装饰性薄膜作为外部物质沉积在功能性和高度专化的器官如皮肤上，因此限制由化妆品配方引起的皮肤生理机能的改变是必不可少的。
特别地，本领域广泛使用的粉状化妆品成分(如颜料和赋形剂)，由于其减小的粒径和高比表面积，引起皮肤脂质和水分的吸收，因此不可避免地改变由皮肤产生的保护性水解脂膜，其因此被耗尽。这种改变的结果是出现皮肤干燥、弹性和色泽损失等不良症状。
实际上，被称为角质层的皮肤外层由浸渍在由神经酰胺、脂肪酸、矿物盐、氨基酸和水组成的水脂基底中的一系列具有蛋白质性质的分化分层的非活细胞层(角质细胞)组成。为了确保角质细胞和它们浸入其中的水脂基底之间的粘附和亲和力，存在共价地锚定到角质细胞本身表面的神经酰胺(ω-羟基神经酰胺，参见Macheleidt,o.et al.(2002)“Deficiency of epidermal protein-bound omega-hydroxyceramides in atopicdermatitis”J.Invest.Dermatol.119,166–173(Macheleidt,o.等(2002)“表皮蛋白结合的ω-羟基神经酰胺在特应性皮炎中的缺乏”，皮肤病学研究杂志119,166-173)和Behne,M.etal,(2000)Omega-hydroxyceramides are required for corneocyte lipid envelope(CLE)formation and normal epidermal permeability barrier function”J.Invest.Dermatol.114,185-192.(Behne,M.等，(2000)“ω-羟基神经酰胺是角膜细胞脂质包膜(CLE)形成和正常表皮渗透屏障功能所需的”，皮肤病学研究杂志114，185-192.))：这种功能化被认为改善了整个表皮的界面和连续性，从而促进其生理功能(机械弹性、体内平衡、汗液屏障、防止微生物攻击等)，使皮肤成为真正的复合生物材料。
与现有技术相比，保护表皮平衡并模仿其化学结构的化妆品粉末的发明是一种需求和改进。
WO2014084657描述了具有共价地锚定到二氧化钛和绢云母表面的季铵和磷酸盐的聚合物涂层，以促进所述粉末粘附到皮肤上。不利的是，缺乏模拟脂质层组成的脂肪特征从而不能保证有效的仿生学。
JP2000290532描述了具有更好的皮肤亲和力的化妆品粉末的制备，其通过简单沉淀的物理方式沉积N-月桂酰基-L-赖氨酸(脂肪氨基酸)，没有形成粉末表面和涂层之间的共价键，而这削弱了其在复杂配方中的稳定性。
KR1446500描述了具有改善的皮肤亲和力的涂层粉末的制备，其通过用相当于表皮中存在的脂质混合物的脂质混合物处理无机基底，在基底和涂层之间没有形成共价键。
JP2014088350描述了涂层有烷氧基硅烷的化妆品粉末，其确保涂层与粉末的共价连接，但没有提供对于有效的防汗作用必不可少的与表皮脂质相似的脂肪功能性和分子量。
本发明的目的是获得具有皮肤角质细胞表面特征的化妆品粉末，能够与角质层无缝地自我整合。
进一步的目的是获得保护表皮平衡的粉末，模拟表皮化学结构。因此，本发明的第一目标是用于化妆品使用的涂层粉末的有机化合物。
所述涂层化合物兼具疏水特征和极性特征，即能够形成或参与氢键，类似于上皮脂质中发生的情况。
本发明的涂层化合物可以进行水解和缩合反应。所述化合物具有脂肪官能团并且同时具有用于氢键(尿烷/尿素基团)的供体——受体能力，类似于上皮脂质的酰胺基团。
这种亲肤涂层化合物具有通式(1)：
A-B-C (1)
其中：
A是具有10至100个碳原子的烃基。
更优选地，A是具有15至25个碳原子的烃基，并且形式上衍生自具有X＝-OH或-NH2的AX前体，其熔点和软化点高于25℃且低于100℃。这样的烃基A可以是线性的、支化的或环状的，此外它可以是饱和的或单不饱和的或多不饱和的或者包含芳环，此外，它可以具有含极性基团、离子或可离子化基团的分支；
B可以是脲基/氨基甲酸酯基，更优选化学式(2)的氨基甲酸酯基：
C是丙基三烷氧基硅烷基团–(CH2)3Si(OR1)x(OR2)3-x，其中0≤x≤3(3)：
其中，R1是乙基–CH2CH3和R2是甲基–CH3。根据通式1的亲肤有机涂层化合物可以从市售试剂开始合成。
在一个实际的实施方案中，通式1可以通过使异氰酸3-(三乙氧硅基)丙酯化合物(4)(CAS#24801-88-5，购自Wako Pure Chemical Industries,Ltd.,Osaka,Japan(日本大阪的和光纯药工业株式会社)，TCI Europe N.V.,Zwijndrecht,Belgium(比利时兹韦恩德雷赫特的东京化成工业株式会社欧洲公司)或美国宾夕法尼亚州莫里斯维尔的Gelest公司)
与等摩尔量的1-二十二醇(INCI：山嵛醇)(CAS#661-19-8，购自Acros Organics,Geel,Belgium(比利时赫尔的Acros Organics公司)，Sigma-Aldrich,St.Louis,MO,UnitedStates(美国密苏里州圣路易斯的Sigma-Aldrich公司)或Merck KGaA,Darmstadt,Germany(德国达姆施塔特的默克集团))在无水癸烷中在80℃的温度下反应6小时，并且在合适的加成反应催化剂(本领域已知)的存在下，得到中间体二十二碳氨甲酰丙基三乙氧基硅烷化合物(5)
中间体化合物(5)可以通过结晶、过滤和干燥以白色蜡状固体的形式从反应环境中提纯。
通式(1)的涂层化合物可以进行溶胶-凝胶工艺，即用于化妆品粉末表面改性的水解和缩合反应，从而产生具有高度粘合能力且具有肌理、润滑和消光整理功能的弹性化妆品粉末。
由于本发明粉末赋予化妆品配方脂肪和极性官能团的化学相容性，涂层化合物(1)的这种水解和缩合反应会获得对皮肤有强粘附性和天然性的化妆品粉末。
所述细粉形式的缩合产物具有的美容特性如：疏水性，因为它不会减少皮肤中的水分；粘附性，因为它适于形成粘附在皮肤上的薄膜；透明度，因为它产生半透明的粉末薄膜，赋予皮肤自然的外观；柔软和光滑性，因为在使用过程中产生愉悦的感觉。
制备化妆品粉末的第一个实施方案，始于化合物(5)在1:1的乙醇:异十二烷混合物中以重量计占10％，在酸性或碱性催化作用下，制备由化合物(5)缩聚得到的有机-无机杂化化合物，具有结构：
这样的固体化合物(6)可以通过过滤、干燥和可能的研磨从缩合环境中提纯，获得粒径<500μm，更优选<250μm，甚至更优选<100μm的粉末状固体，当将其以80-1％加入化妆品配方，更优选50-5％，甚至更优选30-10％，赋予所述配方期望的美容特性。
生产化妆品粉末的第二个实施方案要求缩聚反应在合适的化妆品基底存在下进行。所得到的功能性粉末永久接纳来自缩聚的化合物的新的表面特征。事实上，赋予化妆品粉末新的表面性能的需要要求涂层剂和粉末本身之间稳定的化学改性。
借助于基体上涂层的溶胶-凝胶化学的接枝可以选择具有表面羟基(硅酸盐、硅石、氧化铝、氢氧化铝、钛、珍珠岩)的各种化妆品基底，通过与涂层剂(每个涂层分子最高达3个共价键)形成稳定共价键(Si-O键，452kJ/mol)官能化它们。
举例来说，这样的化学涂层通过在滑石粉上用相对于滑石粉重量1-10％的中间体化合物(5)喷雾获得，更优选相对于滑石重量2-5％，在挥发性有机溶剂(例如乙醇，异丙醇，乙酸乙酯，异十二烷或其混合物)中通过合适的溶液输送化合物。加入酸性(例如稀释的HCL)或碱性(例如NaOH)溶液可以使反应如图所示：
如此获得的粉末在充分混合后，在50-150℃，更优选80-100℃的烘箱中干燥2小时至48小时，更优选超过24小时。
或者，在不同的实施方案中，这样的化妆品粉末可以通过将化合物(1)与化妆品基底用犁铧磨粉机加热到涂层的熔融温度进行干混(无溶剂)获得，然后进行酸或碱催化，温度处理2小时至48小时，更优选大于4小时。
实施例
以下实施例旨在说明本发明但不以任何方式对本发明进行限制。
实施例1
制备通过与直链醇反应获得的“涂层相”
本发明的涂层相通过将相A置于配备有搅拌器、温度计和冷凝器的反应器中来制备。该反应在氮气流下进行，将所述反应物加热至90℃反应约10小时直至活性异氰酸酯基消失。所述消失通过IR评估。随后在约70℃下加入相B。
由此获得的产物具有白色蜡状稠度，熔点约为60℃。
实施例2
制备通过与支链醇反应获得的“涂层相”
按照实施例1所示的步骤制备本发明的涂层相。
由此获得的产物具有白色蜡状稠度，熔点约为35℃。
实施例3
制备通过与部分酯化的乙二醇反应获得的“涂层相”
按照实施例1所示的步骤制备本发明的涂层相。
由此获得的产物具有白色蜡状稠度，熔点约为55℃。
实施例4
制备通过与双亲两性离子分子反应获得的“涂层相”
按照实施例1所示的步骤制备本发明的涂层相。
由此获得的产物具有白色蜡状稠度，软化点约为37℃。
实施例5
制备涂层的化妆品粉末
本实施例的涂层化妆品粉末是通过将相A装入混合机中并用合适的叶轮搅拌获得的，相B和相C在室温下在相A粉末上依次雾化。然后将湿粉末卸载到合适的容器中，并在80℃的烘箱中干燥24小时。烘箱处理后的挥发物含量应<1％。最后，用200目筛筛分粉末。这种涂层粉末的表面张力是35.4dyn/cm。
对于本实施例选择的粉末绝不限制可以使用的所有其他化妆品粉末(云母、二氧化硅等)。
实施例6
制备涂层的化妆品颜料
本实施例的涂层的化妆品颜料是通过将相A装入混合机中并用合适的叶轮搅拌而获得的，室温下相B和相C在相A的颜料上依次雾化。然后将湿粉末卸载到合适的容器中，并在80℃的烘箱中干燥24小时。烘箱处理后的挥发物含量应<1％。最后用200目筛筛分颜料。这种涂层颜料的表面张力是33.9dyn/cm。
对于本实施例选择的颜料决不限制可以使用的所有其他化妆品颜料(二氧化钛、氧化铁黄、氧化铁黑等)。
实施例7
制备涂层的化妆品颜料
本实施例的涂层的化妆品颜料是通过将相A装入混合机中并用合适的叶轮搅拌而获得的，室温下相B和相C在相A的颜料上依次雾化。然后将湿粉末卸载到合适的容器中，并在80℃的烘箱中干燥24小时。烘箱处理后的挥发物含量应<1％。最后用200目筛筛分颜料。这种涂层的颜料的表面张力是35.4dyn/cm。
对于本实施例选择的颜料决不限制可以使用的所有其他化妆品颜料(蓝色1号色淀，黄色5号色淀等)。
实施例8
制备着色的化妆品乳液
实施例9
实施例10
制备口红
实施例11
制备化妆笔
Claims (15)
1.一种具有亲肤表面的化妆品粉末产品，该亲肤表面由涂层化合物提供，而该涂层化合物利用以下通式的溶胶-凝胶化学：
A-B-C (1)
其中：
A是具有10至100个碳原子的烃基，并且形式上衍生自具有X＝–OH或–NH2的AX前体，其熔点或软化点高于25℃且低于100℃；AX前体选自二十二醇基团、十四烷基十八醇基团和C20-30乙二醇异硬脂酸酯基团
B是以下化学式的脲基或氨基甲酸酯基团：
C是化学式(3)的丙基三烷氧基硅烷基团–(CH2)3Si(OR1)x(OR2)3-x，其中，0≤x≤3，
其中，R1代表乙基–CH2CH3，R2代表甲基–CH3。
2.如权利要求1所述的化妆品粉末产品，其特征在于：
A是具有15至25个碳原子的烃基；
B是氨基甲酸酯基团；
C是丙基三烷氧基硅烷基–(CH2)3Si(OR1)x(OR2)3-x，其中0≤x≤3，R1代表乙基–CH2CH3，R2代表甲基–CH3。
3.如权利要求1所述的化妆品粉末产品，其特征在于，所述涂层化合物形成固体化合物，该固体化合物衍生自由以下化学式表示的二十二碳氨甲酰丙基三乙氧基硅化合物：
4.如权利要求3所述的化妆品粉末产品，其特征在于，所述固体化合物是粒度<250μm的粉末状固体。
5.如权利要求3所述的化妆品粉末产品，其特征在于，所述固体化合物是粒径<100μm的粉末状固体。
6.如权利要求4所述的化妆品粉末产品，其特征在于，所述粉末状固体以80％至1％的百分比添加至化妆品配方中。
7.如权利要求6所述的化妆品粉末产品，其特征在于，所述粉末状固体以50％至5％的百分比添加至化妆品配方中。
8.如权利要求6所述的化妆品粉末产品，其特征在于，所述粉末状固体以30％至10％的百分比添加至化妆品配方中。
9.如权利要求1所述的化妆品粉末产品，其特征在于，所述化妆品粉末产品还包括化妆品基底，所述化妆品基底包含适于通过与所述涂层化合物形成稳定的共价键而官能化的表面硅烷醇。
10.如权利要求9所述的化妆品粉末产品，其特征在于，所述涂层化合物包括相对于化妆品基底重量1％至10％的二十二碳氨甲酰丙基三乙氧基硅化合物。
11.如权利要求10所述的化妆品粉末产品，其特征在于，所述涂层化合物包含2至5％的二十二碳氨甲酰丙基三乙氧基硅化合物。
12.如权利要求1所述的化妆品粉末产品，其中，所述涂层化合物用于形成压制粉底。
13.如权利要求1所述的化妆品粉末产品，其中，所述涂层化合物用于形成口红。
14.如权利要求1所述的化妆品粉末产品，其中，所述涂层化合物用于形成化妆笔。
15.如权利要求5所述的化妆品粉末产品，其特征在于，所述粉末状固体以80％至1％的百分比添加至化妆品配方中。
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| US20180133136A1 (en) | 2018-05-17 |
| EP3294266A1 (en) | 2018-03-21 |
| EP3294266B1 (en) | 2019-06-05 |
| JP6732802B2 (ja) | 2020-07-29 |
| KR20180030472A (ko) | 2018-03-23 |
| JP2018520998A (ja) | 2018-08-02 |
| KR102593238B1 (ko) | 2023-10-23 |
| WO2016181251A1 (en) | 2016-11-17 |
| US10292923B2 (en) | 2019-05-21 |
| CN107635540A (zh) | 2018-01-26 |
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