CN108290906B - 一种烷氧基硅烷化合物或其盐、其制备方法以及含有该化合物的毛发用组合物 - Google Patents
一种烷氧基硅烷化合物或其盐、其制备方法以及含有该化合物的毛发用组合物 Download PDFInfo
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- CN108290906B CN108290906B CN201680069569.0A CN201680069569A CN108290906B CN 108290906 B CN108290906 B CN 108290906B CN 201680069569 A CN201680069569 A CN 201680069569A CN 108290906 B CN108290906 B CN 108290906B
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- alkoxysilane
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- -1 Alkoxy silane compound Chemical class 0.000 title claims abstract description 69
- 210000004209 hair Anatomy 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title description 35
- 150000003839 salts Chemical class 0.000 title description 24
- 229910000077 silane Inorganic materials 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- PVNHWQFFHAUMIB-UHFFFAOYSA-N n-[2-(3-trimethoxysilylpropylamino)ethyl]dodecanamide;hydrochloride Chemical compound Cl.CCCCCCCCCCCC(=O)NCCNCCC[Si](OC)(OC)OC PVNHWQFFHAUMIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 3
- SMUMTCNTZHFRSU-UHFFFAOYSA-N [Cl-].C(CCCCCCCCCCCCCCC)NCC[NH2+]CCC[Si](OC)(OC)OC Chemical compound [Cl-].C(CCCCCCCCCCCCCCC)NCC[NH2+]CCC[Si](OC)(OC)OC SMUMTCNTZHFRSU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- KKQSYBUSGIONOQ-UHFFFAOYSA-N [Cl-].C(CCCCCCCCCCC)(=O)N(CC[NH3+])CCC[Si](OC)(OC)OC Chemical compound [Cl-].C(CCCCCCCCCCC)(=O)N(CC[NH3+])CCC[Si](OC)(OC)OC KKQSYBUSGIONOQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003750 conditioning effect Effects 0.000 abstract description 10
- 239000008346 aqueous phase Substances 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 4
- 230000002459 sustained effect Effects 0.000 abstract description 3
- 239000006185 dispersion Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 150000003863 ammonium salts Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
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- 229940008099 dimethicone Drugs 0.000 description 5
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 210000004761 scalp Anatomy 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
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- MRKXCQPDRPTZCG-IUQGRGSQSA-N (9e,12e,15e)-octadeca-9,12,15-trienoyl chloride Chemical compound CC\C=C\C\C=C\C\C=C\CCCCCCCC(Cl)=O MRKXCQPDRPTZCG-IUQGRGSQSA-N 0.000 description 2
- FBWMYSQUTZRHAT-HZJYTTRNSA-N (9z,12z)-octadeca-9,12-dienoyl chloride Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O FBWMYSQUTZRHAT-HZJYTTRNSA-N 0.000 description 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种具有新型结构的烷氧基硅烷盐化合物、其制备方法和含有该化合物的毛发用组合物，所述烷氧基硅烷衍生物在水相中形成自聚集体从而可以提高毛发用组合物的储存稳定性及分散稳定性，并且可以提供对毛发的持续调理效果。
Description
技术领域
本申请主张基于2015年9月30日申请的韩国专利申请第10-2015-0137229号、2016年9月23日申请的韩国专利申请第10-2016-0121880号的优先权，同时，所述韩国专利申请文献中所揭示的全部内容作为本说明书的一部分包含在本说明书中。
本发明涉及一种通过自聚集性来提高组合物的稳定性和调理效果的烷氧基硅烷化合物或其盐、其制备方法和含有该化合物的毛发用组合物。
背景技术
头发因重复洗涤和梳理等物理刺激、染色和烫发等化学刺激而受到损害。为了改善受损的头发，已经开发了各种调理化合物如阳离子表面活性剂、阳离子聚合物和硅化合物，但目前调理效果的持久性不足。
最近，据报道，具有胺基的烷氧基硅烷化合物有助于赋予头发调理效果和体积感，因此对其越来越关注。
赋予头发调理效果的烷氧基硅烷化合物不仅在施用于头发表面后表现出有限的持久性(Limited durability)，而且还存在由于其与水的反应性产生的储存时的稳定性问题以及与表面活性剂或调理剂中包含的组分不相容的问题。
为了解决这些问题，韩国公开专利第2014-0040762号公开了烷氧基硅烷化合物中包含脂肪酸酯和硅酮的组合物，以及韩国公开专利第2014-0040764号公开了含有烷氧基硅烷和改性淀粉的组合物。
然而，尽管做了这些努力，烷氧基硅烷化合物仍然存在持久性和稳定性方面的问题。
[现有技术文献]
[专利文献]
韩国公开专利第2014-0040762号“包含烷氧基硅烷、脂肪酸酯和硅酮的组合物及其美容用途”
韩国公开专利第2014-0040764号“包含烷氧基硅烷和改性淀粉的组合物以及其美容用途”
发明内容
【技术课题】
对此，本发明的发明人确认通过以往的方法即向烷氧基硅烷化合物中加入其它组分不能解决上述问题，因此为了解决所述问题，进行了多方面的研究，结果制备出同时具有亲水性和疏水性的烷氧基硅烷盐化合物，并且确认该化合物在水相中形成自聚集体而提高了组合物的稳定性并改善了调理持久性，从而完成了本发明。
因此，本发明的目的是提供一种具有新型结构的烷氧基硅烷化合物或其盐。
另外，本发明的另一个目的是提供所述烷氧基硅烷化合物或其盐的制备方法。
另外，本发明的又一个目的是提供包含所述烷氧基硅烷化合物或其盐的毛发用组合物的用途。
【技术解决方法】
本发明为了达到所述目的，提供包含由以下化学式1表示的烷氧基硅烷的化合物或其盐：
[化学式1]
(在所述化学式1中，R1至R5和n如说明书中所述。)
在这种情况下，所述烷氧基硅烷盐化合物的特征为，由以下化学式2或化学式3表示：
[化学式2]
(在所述化学式2中，R1至R3、R5和n、X如说明书中所述。)
[化学式3]
(在所述化学式3中，R1至R4、n、X如说明书中所述。)
此外，本发明提供了化学式1的制备方法，该方法包括使由以下化学式4表示的三烷氧基甲硅烷基化合物与由以下化学式5表示的脂肪酸卤化物反应。
[化学式4]
(在所述化学式4中，R1至R3、和n如说明书中所述。)
[化学式5]
R'-X
(在所述化学式5中，R’和X如说明书中所述。)
另外，本发明提供包含所述化学式1表示的烷氧基硅烷化合物或其盐的毛发用组合物。
【发明的效果】
本发明的烷氧基硅烷化合物或其盐可以在水相中形成纳米级自聚集体，以此阻止与水的直接反应，从而提高了在水相中的稳定性，而稳定性是在传统烷氧基硅烷化合物中一直存在的问题。此外，由于所述烷氧基硅烷化合物的亲水性/疏水性特性，它与毛发用组合物中的其他组分或添加剂的混溶性极好，因此可以提高毛发用组合物的分散稳定性。
根据本发明的毛发用组合物施用于头发后，会残留在头发上，从而提供持续的调理效果，并且在弹性、柔软度、光泽和持久性等所有方面提供高水平的满意度。
另外，这种毛发用组合物在自聚集体中可含有对头发有用的组分，因此能够生产出各种功能性产品。
附图说明
图1是用于说明本发明的烷氧基硅烷盐化合物自聚集体的形成的示意图；
图2示出实验例2的比色测量结果的图像，各表示(a)无处理组、(b)比较例1的组合物、(c)实施例1的组合物和(d)实施例2的组合物。
具体实施方式
本发明提出了一种新型结构的化合物，由于其自聚集特性，能够制备具有优异稳定性的组合物，并且当施用于头发时表现出持续的头发调理效果。
优选地，本发明提供由以下化学式1表示的烷氧基硅烷化合物或其盐：
[化学式1]
(所述化学式1中，R1至R3彼此相同或不同，且各自独立地为H、C1～C6的烷基或-Si(OR6)3，其中所述R6为H或C1～C6的烷基，R4为H或-C(＝O)OR7，其中所述R7为C8～C24的烷基，R5为H或-C(＝O)OR8，其中所述R8为C8～C24的烷基，n是1至10的整数。)
如本文所用，除非另有说明，烷基包括直链和支链基团。例如，所述烷基可以是甲基、乙基、丙基、异丙基、丁基、戊基、己基、辛基、异辛基、壬基、癸基、十二烷基、异壬酰基、癸酰基、新癸酰基、月桂酰基、肉豆蔻基、棕榈酰基、硬脂酰基、油酰基、亚油酸基、亚麻烯基、花生四酰基、二十二酰基等。
优选地，在所述化学式1中，所述R1至R3彼此相同或不同，且各自独立地为H、甲基、乙基或丙基，R4为H或-C(＝O)OR7，其中所述R7为C10～C20烷基，R5为H或-C(＝O)OR8，其中所述R8为C10～C20烷基，n是1或2。
特别地，根据本发明的烷氧基硅烷盐化合物可以以盐形式制备。具体而言，由化学式1的结构内-NR5或-NHR4制备为铵盐，盐的位置取决于R4和R5的官能团的类型。在这种情况下，铵盐的是由游离酸(free acid)形成的酸加成盐更有利。
酸加成盐可以是无机酸如盐酸、硝酸、磷酸、硫酸、氢溴酸、氢碘酸、亚硝酸和亚磷酸；有机酸如脂族单体和二羧酸酯、苯基取代的链烷酸酯、羟基链烷酸酯和链烷二酸酯、芳族酸、脂族和芳族磺酸等；和有机酸如乙酸、苯甲酸、柠檬酸、乳酸、马来酸、葡糖酸、甲磺酸、4-甲苯磺酸、酒石酸和富马酸。
优选地，所述盐可以是含有卤素离子的铵盐，更优选含有阴离子F、Cl、Br或I。
本发明中揭示的化学式1的烷氧基硅烷化合物，在分子结构中含有两个胺基，因此具有由R4和R5表示的高级脂肪酸的长烷基。优选地，当R4为H时，R5为-C(＝O)OR8，当R5为H时，R4为-C(＝O)OR7。
(i)当R4＝H，R5＝-C(＝O)OR8时
当R4是H时，其连接处的胺具有铵盐形式，R5具有高级脂肪酸的长烷基，并且该化合物可以由以下化学式2表示：
[化学式2]
(在所述化学式2中，R1至R3、R5和n如前所述，X为F、Cl、Br或I。)
(ii)当R4＝-C(＝O)OR7，R5＝H时
当R5是H时，其连接处的胺具有铵盐形式，R4具有高级脂肪酸的长烷基，并且该化合物可以由以下化学式3表示：
[化学式3]
(在所述化学式3中，R1至R4、n和X如前所述。)
更优选地，所述烷氧基硅烷盐化合物的具体实施例的化合物如下：
(1)[2-(N-十六烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵；
(2)[2-(N-十二烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵；
(3)[2-(N-十六烷酰氨基)乙基]氨基乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵；
(4)[2-{N-十二烷酰基-[3-(三甲氧基甲硅烷基)丙基]氨基}乙基氯化铵和
(5)2-{N-十六烷酰基-[3-[(三甲氧基甲硅烷基)丙基]氨基]}乙基氯化铵。
所述化学式1表示的烷氧基硅烷盐化合物可以以水合物或溶剂合物的形式提供。
所述化学式1的烷氧基硅烷盐化合物在分子结构中同时含有可显示疏水性的长烷基即高级脂肪酸烷基和具有亲水性的铵盐，在固体/气体、固体/液体、固体/固体，液体/气体和液体/液体界面具有活性。如图1所示，这种化学式1的烷氧基硅烷盐化合物在水相(water phase)中形成自聚集体，其特征为，具有疏水性的硅氧烷基和具有疏水性的烷基排列在自聚集体内部，具有亲水性的铵基排列在自聚集体外部，对于这种自聚集性质，高级脂肪酸的烷基越长越有利。
另外，根据本发明的化学式1的烷氧基硅烷化合物或其盐可以通过由以下化学式4表示的三烷氧基甲硅烷基化合物与由以下化学式5表示的脂肪酸卤化物的反应来制备：
[化学式4]
(在所述化学式4中，R1至R3和n如前所述。)
[化学式5]
R'-X
(在所述化学式5中，R'是H或-C(＝O)OR",其中所述R"是C8～C24的烷基，X如前所述。)
化学式4的三烷氧基甲硅烷基化合物是分子结构中具有胺基的化合物，并且可以使用任何满足R1～R3和n的定义的化合物，可以直接制备或者购买使用。例如，所述三烷氧基甲硅烷基化合物可以是N-[3-(三甲氧基甲硅烷基)丙基]-乙二胺、N-[3-(三乙氧基甲硅烷基)丙基]-乙二胺、N-[3-(三甲氧基甲硅烷基)丙基]-二亚乙基三胺或N-[3-(三乙氧基甲硅烷基)丙基]-二亚乙基三胺。
所述化学式5的脂肪酸卤化物可以是任何通过与化学式4的三烷氧基甲硅烷基化合物的胺结合生成铵盐的任何化合物。例如，所述脂肪酸卤化物可以选自由异壬酰氯(isononanoyl chloride)、癸酰氯(capryl chloride)、新癸酰氯(neodecanoylchloride)、月桂酰氯(lauroyl chloride)、肉豆蔻酰氯(myristoyl chloride)、棕榈酰氯(palmitoyl chloride)、硬脂酰氯(stearoyl chloride)、油酰氯(oleoyl chloride)、亚油酸酰氯(linoleoyl chloride)、亚麻烯酰氯(linolenoyl chloride)、花生酰氯(arachidoyl chloride)、二十二酰氯(behenoyl chloride)组合的群中至少一种，并且可优选使用棕榈酰氯或月桂酰氯。
在这种情况下，盐可以以铵盐的形式获得，并且可以通过去除卤素X来制备化学式1的烷氧基硅烷化合物。在这种情况下，X的去除在本发明中没有特别限制，并且可以通过已知的方法来制备。
特别地，化学式1的化合物可以制备为化学式2或化学式3的盐化合物的形式，根据R4和R5的定义，它们可以大致以两种方式制备。
(i)当R4＝H，R5＝-C(＝O)OR8时[化学式2的盐]
化学式2的烷氧基硅烷盐化合物的制备如以下反应式1所示，通过化学式4的化合物与化学式6的脂肪酸卤化物的反应来制备。
[反应式1]
(在所述反应式1中，R1至R3、R5和n、X如前所述。)
所述化学式4的化合物如前所述。
化学式6的脂肪酸卤化物R5-X用于满足R5和X的定义，如R’-X中所述。
此反应在溶剂中进行，且本发明对溶剂没有特别限制，可以是脂族烃溶剂如己烷、庚烷或环己烷；卤代烃溶剂如氯仿、四氯乙烯、四氯化碳、二氯甲烷或二氯乙烷；碳酸丙烯酯、碳酸亚乙酯、碳酸二甲酯、碳酸二丁酯、碳酸甲乙酯、碳酸二丁酯、硝基甲烷、硝基苯等；酮溶剂如丙酮、甲乙酮、甲基异丁基酮或环己酮；酰胺溶剂如N-甲基-2-吡咯烷酮、2-吡咯烷酮、N-甲基甲酰胺或N，N-二甲基甲酰胺；亚砜溶剂如二甲基亚砜或二乙基亚砜；砜溶剂如二乙基砜或环丁砜；腈溶剂如乙腈或苯甲腈；胺溶剂例如烷基胺、环胺或芳香胺；酯溶剂如丁酸甲酯、丁酸乙酯或丙酸丙酯；羧酸酯溶剂如乙酸乙酯或乙酸丁酯；或芳族烃溶剂如苯、乙苯、氯苯、甲苯或二甲苯，作为一个实例，所述溶剂可以是二氯甲烷。
所述有机溶剂可以单独使用或混合两种以上使用，并且相对于1重量份的化学式6的化合物，可以使用10至100重量份，以使反应可以充分进行。
所述反应可以在-4至40℃进行，更优选在0至10℃的低温下进行，并且反应可以进行30分钟至3小时，更优选进行1至2小时。当反应后晶体沉淀时，可以通过过滤获得化学式2的盐。
(ii)当R4＝-C(＝O)OR7，R5＝H时[化学式3的盐]
由化学式3表示的烷氧基硅烷盐化合物，如以下反应式2所示，可以通过以下步骤制备：
在碱存在下将保护基团(PG)引入由化学式4表示的三烷氧基甲硅烷基化合物的伯胺中的步骤；
使引入保护基团的化学式7的化合物与化学式8的脂肪酸卤化物反应的步骤；及
从获得的化学式9的化合物中去除保护基团的步骤。
[反应式2]
(在所述反应式2中，R1至R4、n和X如前所述。)
使用所述保护基团(PG)，用于在分子结构中形成铵盐，而不是在末端形成铵盐如所述反应式1，即用于保护末端胺基。可以使用的保护基团(PG)可以选自由Bz(苄基，benzyl)、Trt(三苯甲基，trityl)、BOC(叔丁氧基羰基，t-butyloxycarbonyl)、AC(乙酸根，acetate)、Cbz(羧基苄基,carboxybenzyl)或Fmoc(9-芴基甲氧羰基,9-fluorenylmethoxycarbonyl)组合的群中的至少一种，优选地可以使用BOC。
在此反应中，碱可以包括选自由三甲胺、三乙胺、三丙胺、三丁胺、三戊胺、三辛胺、三苄胺、氢氧化钠、氢氧化钾、氢氧化锂、氢氧化钙、碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾组合的群中的至少一种，并且优选三乙胺。
化学式8的脂肪酸卤化物可以选自所述反应式1中提及的脂肪酸卤化物，并且优选棕榈酰氯或月桂酰氯。
此时，反应温度、反应时间、溶剂等参照所述反应式1。
从反应后得到的化学式9化合物中去除末端的保护基团。在这种情况下，保护基团的去除在本发明中不受特别限制，可以通过已知方法去除，并且可以根据保护基团的种类采用不同的方式。
例如，Boc可以通过如盐酸、硫酸、甲磺酸、磷酸、溴酸、硝酸、亚硝酸、三氟乙酸、乙酸等酸处理而去除。另外，Boc可以通过在Pd/C催化剂存在下并在1-2atm的压力下加氢进行催化氢化处理来去除。
用途
如上所述，烷氧基硅烷盐化合物形成自聚集体，如图1所示，因此可用于需要它们的各种领域。
优选地，化学式1的烷氧基硅烷盐化合物可以用于毛发用组合物。
大多数常规的烷氧基硅烷化合物以液体形式存在，并且在施用于表面之后具有有限的持久性，储存时具有低稳定性，以及存在与其他组分(例如表面活性剂和调理剂组分)的混溶性差的问题。根据本发明的引入高级脂肪酸的烷氧基硅烷化合物或其盐，可以在水相中形成自聚集体，组合物内稳定性高，分子结构内具有亲水性及疏水性官能团，由此与其它组分的混溶性(或相容性)优异，因此提高了组合物的稳定性并进一步增强了调理剂等活性组分的持久性。
本发明的化学式1的烷氧基硅烷化合物或其盐，基于毛发用组合物总重量，含量为0.001至15重量％，优选为0.1至10重量％。当含量小于上述范围时，不能保证上述效果。与此相反，当含量超过上述范围时，组合物的稳定性可能降低或表现出粘稠的使用感。因此，在上述范围内适当使用烷氧基硅烷化合物或其盐。
特别地，可以期待以下效果，即可以由化学式1的烷氧基硅烷化合物或其盐形成直径为50至500nm，优选100至400nm的自聚集体，在所述自聚集体内携带并递送可以减轻脱发的成分或有助于头发健康的成分。
所述可携带的头发有效成分可以选自由米诺地尔、4-吡咯烷2，6-二氨基嘧啶-1-氧化物(4-pyrrolidine 2,6-diaminopyrimidine-1-oxide)、柏子仁、维生素B5衍生物(泛醇衍生物)、獐牙菜提取物(獐牙菜，Swertiall)、薏苡仁、甘草提取物(甘草甜素和甘草次酸，glycyrrhizin and glycyrrhetic acid)、烟酰胺(niacinamide)、维生素E衍生物、腺苷(adenosine)、十五烷酸甘油酯(glyceryl pentadecanoate)、苄基氨基嘌呤(6-苄基氨基嘌呤，6-benzylaminopurine)、丁香油酚(Eugenol)、锯棕榈(Saw palmetto)、二烷基单胺衍生物(dialkylmonoamine derivatives)、异黄酮(isoflavones)、桧醇(Hinokitiol)和烟酸苄酯(benzyl nicotinate)组合的群中至少一种，但不限于此。
包含所述烷氧基硅烷盐化合物及有效成分的毛发用组合物，可适用于任何形式的制剂，例如洗发香波、染发剂(hair rinse)、护发素(hair conditioner)、发膏、润发乳、头皮发膜、生发剂、头发营养化妆水、头发护理剂(hair treatment)、头发安瓿、精华素、摩丝、发蜡、发胶、定型凝胶或头皮护理剂等。
在各制剂中，对于除上述必需成分以外的成分，本领域技术人员可以根据制剂的种类或使用目的适当选择和添加。
例如，可以使用硅化合物例如环聚二甲基硅氧烷、二甲聚硅氧烷、苯基三甲基聚硅氧烷、氨端聚二甲基硅氧烷、聚二甲基硅氧烷(polydimethylsiloxane)、苯基硅氧烷(phenyl siloxane)、烷基甲基硅氧烷(alkylmethylsiloxane)和聚二甲基硅氧烷共聚醇(dimethicone copolyol)。
除了所述硅化合物之外，可添加用于维持物质基本特性及品质的本领域技术人员公知和使用的常规成分，如防腐剂、增稠剂、粘度调节剂、pH调节剂、香料等，并且可以包含去离子水、有机溶剂等作为溶剂。
例如，有机溶剂可以包括正丁醇、叔丁醇、苯甲醇、苯乙醇、己醇、异丙醇、甲醇、油醇、丙醇、环己烷二甲醇、苯氧乙醇、丁氧基乙醇、二氧乙醇、甲氧基乙醇、甲氧基乙二醇、丁二醇、丙二醇、戊二醇、己二醇、苄基乙二醇、二乙二醇、二丙基二醇、1,2-丁二醇、1,4-丁二醇、2,3-丁二醇、丙二醇、1,5-戊二醇、异戊二醇、乙基己二醇、1,2-己二醇、1,2,6-己二醇、1,10-癸二醇、3-甲氧基丁醇、甲氧基异丙醇、甲氧甲基丁醇、碳酸乙烯酯、碳酸丙烯酯及其混合物。
防腐剂可以含有对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯、对羟基苯甲酸丙酯、苯甲醇、苯氧基乙醇、苯氧基异丙醇、苯丙醇、甲基氯异噻唑啉酮和甲基异噻唑啉酮的混合物。
增稠剂或粘度调节剂可以包括脂肪酸醇、脂肪酸、羟丙基甲基纤维素、羟甲基纤维素、氯化钠、氯化铵、丙二醇和己二醇。
pH调节剂可以包括乙酸、己二酸、氨基乙基丙二醇、氨基甲基丙二醇、氨基甲基丙醇、氨基丙二醇、抗坏血酸、壬二酸、苯甲酸、二丁基乙醇胺、丁基乙醇胺、柠檬酸、二丁醇乙醇胺、二乙醇胺、二异丙胺、二异丙醇胺、二甲基异丙醇胺、甲基乙醇胺、富马酸、半乳糖醛酸、戊二酸、乙醇酸、异丙醇胺、异丙胺、马来酸、苹果酸、丙二酸和甲基乙醇胺。
此时，对于每个组分的选择及其含量在本发明中没有特别限制，但可以由本领域普通技术人员适当地选择，例如，可以在0.001到10％重量％范围内包含相关组分。
【发明实施的具体形态】
为了帮助理解本发明，下面将提供实施例。下面说明的实施例，是与本发明的效果有关的示例性说明，本发明的权利范围及效果并不局限于此。
[实施例1]
<制备例1>
制备[2-(N-十六烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵
[化学式12]
将6.67g(30mmol)的N-[3-(三甲氧基甲硅烷基)丙基]-乙二胺溶于二氯甲烷中，然后在冰浴中搅拌的同时缓慢加入9.15mL(30mmol)棕榈酰氯。30分钟后，将反应完成后得到的反应产物在减压下蒸馏，然后加入乙醚进行沉淀反应。过滤沉淀的固体并干燥，得到13.8g(收率：92％)的白色固体即化学式12的化合物。
1H-NMR(ppm):δ0.73,0.88,1.24,1.57,2.23,3.21,3.55,3.64
<制备例2>
制备[2-(N-十二烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵
[化学式13]
将6.67g(30mmol)的N-[3-(三甲氧基甲硅烷基)丙基]-乙二胺溶于二氯甲烷中，然后在冰浴中搅拌的同时缓慢加入6.9mL(30mmol)月桂酰氯。30分钟后，将反应完成后得到的反应产物在减压下蒸馏，然后加入乙醚进行沉淀反应。过滤沉淀的固体并干燥，得到12.0g(收率：90％)的白色固体即化学式13的化合物。
1H-NMR(ppm):δ0.73,0.88,1.25,1.56,2.25,3.21,3.55,3.68
<制备例3>
制备[2-(N-十六烷酰氨基)乙基]氨基乙基]-[3-(三甲氧基甲硅烷基)丙
基]氯化铵
[化学式14]
将7.96克(30mmol)的N-[3-(三甲氧基甲硅烷基)丙基]-二亚乙基三胺溶于二氯甲烷中，然后在冰浴中搅拌的同时缓慢加入9.15(30mmol)棕榈酰氯。30分钟后，将反应完成后得到的反应产物在减压下蒸馏，然后加入乙醚进行沉淀反应。过滤沉淀的固体并干燥，得到14.2g(收率：90％)的白色固体即化学式14的化合物。
1H-NMR(ppm):δ0.73,0.89,1.25,1.56,2.24,2.74,3.23,3.57,3.65
<制备例4>
制备[2-{N-十二烷酰基-[3-(三甲氧基甲硅烷基)丙基]氨基}乙基氯化铵
[化学式15]
将6.67g(30mmol)的N-[3-(三甲氧基甲硅烷基)丙基]-乙二胺和4.6mL(33mmol)三乙胺溶于二氯甲烷中，然后在冰浴中搅拌的同时缓慢加入7.2g(30mmol)二碳酸二叔丁酯的溶解溶液。向反应混合物中缓慢滴加9.15mL(30mmol)棕榈酰氯，进行反应。
然后，将得到的反应产物减压蒸馏，加入乙醚，过滤。收集滤液并浓缩，然后在HCl甲醇溶液中搅拌。30分钟后，将反应完成后得到的反应产物在减压下蒸馏，然后加入乙醚进行沉淀反应。过滤析出的固体并干燥，得到10.9g(收率73％)白色固体即化学式15的化合物。
1H-NMR(ppm):δ0.72,0.87,1.24,1.59,2.26,3.20,3.52,3.61
<制备例5>
制备2-{N-十六烷酰基-[3-[(三甲氧基甲硅烷基)丙基]氨基]}乙基氯化铵
[化学式16]
将6.67g(30mmol)的N-[3-(三甲氧基甲硅烷基)丙基]-乙二胺和4.6mL(33mmol)三乙胺溶于二氯甲烷中，然后在冰浴中搅拌的同时缓慢加入7.2g(30mmol)二碳酸二叔丁酯的溶解溶液。向反应混合物中缓慢滴加6.9mL(30mmol)月桂酰氯，进行反应。
然后，将得到的反应产物减压蒸馏，加入乙醚，过滤。收集滤液并浓缩，然后在HCl甲醇溶液中搅拌。30分钟后，将反应完成后得到的反应产物在减压下蒸馏，然后加入乙醚进行沉淀反应。过滤沉淀的固体并干燥，得到9.6g(收率：72％)白色固体即化学式16的化合物。
1H-NMR(ppm):δ0.73,0.88,1.25,1.56,2.25,3.21,3.55,3.68
实验例1：确认自聚集体的形成和稳定性
将所述<制备例1>～<制备例5>的盐分别加入到二氯甲烷中通过加热溶解，并将所得溶液逐滴加入到60-70℃的去离子水中，同时搅拌。搅拌完成后，通过减压蒸馏去除反应溶液中的溶剂以制备自聚集的样品。使用激光粒度仪(Zetasizer)在制备时和制备所得样品三天后观察自聚集体的粒径，结果显示在下表1中。
表1
| 区分 | 制备时 | 制备三天后 |
| 制备例1 | 263nm | 266nm |
| 制备例2 | 247nm | 259nm |
| 制备例3 | 281nm | 288nm |
| 制备例4 | 267nm | 265nm |
| 制备例5 | 253nm | 263nm |
参照所述表1，制备例1至5的所有化合物均形成了直径为200至300nm的自聚集体。
此外，在比较制备时和制备3天后的自聚集体的尺寸时，可以确定经过3天粒径没有发生大的变化，其稳定性优秀。
由于这种自聚集作用，烷氧基硅烷基团被置于自聚集体中的疏水部分，从而减少了与水的接触，从而提高了储存期间的稳定性。另外，可判断出烷基越长，这种效果越明显。
实施例1、实施例2和比较例1：头发护理剂型的制备
以下表2的组成，根据已知方法制备包含所述<制备例1>及<制备例2>化合物的头发护理剂型的毛发用组合物。
表2
实验例2：评估毛发残余力
用1g上述实施例和比较例中制备的毛发用组合物处理羊毛布，在30～35℃用水充分洗涤，然后用一定量的洗发剂反复洗涤三次。
将用水洗涤的羊毛布和用洗发剂洗涤三次的羊毛布浸入0.5％鲁宾染料(Rubindye)溶液染色3分钟，然后使用比色计的红色(a值)进行毛发上的残余力评价，结果如表3和图2所示。此时，未处理组是指作为对照组的未经处理的羊毛布。由于鲁宾染料是阴离子染料并且与吸附在头发上的阳离子聚合物或阳离子聚合物-阴离子表面活性剂复合物进行离子结合，通过测量染色程度可以估算毛发上的残留量。此时，a值越高，吸附在头发上的残留量越高。
表3
| 区分 | 用洗发剂洗涤三次后的比色计a值 |
| 未处理组 | 4.0 |
| 比较例1的组合物 | 11.1 |
| 实施例1的组合物 | 17.6 |
| 实施例2的组合物 | 16.3 |
参考所述表3，根据本发明包含烷氧基硅烷盐化合物的实施例1和2的组合物，残余力与未处理组相比，显示出改善约4至5倍。
另外，可以确定，与不含烷氧基硅烷盐化合物的比较例1的组合物相比，洗发剂清洁后的毛发残余力得到改善，从而表现出持久的调理效果。
实验例3：评价满意度
通过20人专家小姐，对上述实施例和比较例中制备的毛发用组合物的头发弹性、柔软度、光泽和定型持久性等整体满意度进行评估。
每个项目的满意度通过1、3、5、7、9分的分值(评分越高，满意度越高)进行评估，然后对每个评分累计以获得平均值(满意度)，结果显示在下表4中。
表4
| 区分 | 比较例1 | 实施例1 | 实施例2 |
| 弹性 | 2.8 | 4.3 | 4.5 |
| 柔软度 | 2.9 | 5.8 | 5.5 |
| 光泽 | 2.9 | 4.2 | 4.1 |
| 持久性 | 2.6 | 6.8 | 6.1 |
| 满意度 | 2.7 | 6.1 | 5.7 |
参照表4，确认了与比较例1相比，本发明的包含烷氧基硅烷盐化合物的实施例1和2的毛发用组合物在弹性、柔软度、光泽和持久性等所有方面显示出优异的结果，并且整体满意度得到改善。
下面，将对其他剂型进行说明，但根据本发明的包含烷氧基硅烷盐化合物的毛发用组合物的剂型并不局限与此。
剂型例1：生发剂
根据如下所述的组成以常规方法制备生发剂。
表5
剂型例2：头皮精华
根据如下所述的组成以常规方法制备头皮精华。
表6
| 组成 | 含量(重量％) |
| 制备例1的化合物 | 0.5 |
| 乙醇 | 30.0 |
| 聚山梨酯60 | 1.5 |
| 甘油 | 3.0 |
| 聚羧乙烯 | 0.1 |
| 三乙醇胺 | 0.2 |
| 防腐剂 | 适量 |
| 香料和色素 | 适量 |
| 纯化水 | 余量 |
Claims (9)
1.一种用于毛发用组合物的烷氧基硅烷盐化合物，其特征在于，由以下化学式2或化学式3表示：
[化学式2]
[化学式3]
所述化学式2和化学式3中，R1至R3彼此相同或不同，且各自独立地为C1～C6的烷基，
R4为H或-C(＝O)R7，其中所述R7为C8～C24的烷基，
R5为H或-C(＝O)R8，其中所述R8为C8～C24的烷基，
n是1，
X是F、Cl、Br或I。
2.根据权利要求1所述的用于毛发用组合物的烷氧基硅烷盐化合物，其特征在于，
所述化学式2或化学式3的烷氧基硅烷盐化合物选自由
(1)[2-(N-十六烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵；
(2)[2-(N-十二烷酰氨基)乙基]-[3-(三甲氧基甲硅烷基)丙基]氯化铵；
(4)[2-{N-十二烷酰基-[3-(三甲氧基甲硅烷基)丙基]氨基}]乙基氯化铵和
(5)2-{N-十六烷酰基-[3[-(三甲氧基甲硅烷基)丙基]氨基]}乙基氯化铵
组合的群中的任何一种。
3.一种由化学式2表示的用于毛发用组合物的烷氧基硅烷盐化合物的制备方法，其特征在于，根据以下反应式1包含化学式4的化合物与化学式6的脂肪酸卤化物的反应的步骤：
[反应式1]
在所述反应式1中，
R1至R3彼此相同或不同，且各自独立地为C1～C6的烷基，
R5为H或-C(＝O)R8，其中所述R8为C8～C24的烷基，
n是1，
X是F、Cl、Br或I。
4.一种由化学式3表示的用于毛发用组合物的烷氧基硅烷盐化合物的制备方法，其特征在于，根据以下反应式2包含：
在碱存在下将保护基团引入由以下化学式4表示的三烷氧基甲硅烷基化合物的伯胺中的步骤；
使引入保护基团的化学式7的化合物与化学式8的脂肪酸卤化物反应的步骤；及
从获得的化学式9的化合物中去除保护基团的步骤：
[反应式2]
在所述反应式2中，
R1至R3彼此相同或不同，且各自独立地为C1～C6的烷基，
R4为H或-C(＝O)R7，其中所述R7为C8～C24的烷基，
n是1，
X是F、Cl、Br或I。
5.根据权利要求4所述的用于毛发用组合物的烷氧基硅烷盐化合物的制备方法，其特征在于，所述碱是三乙胺。
6.根据权利要求4所述的用于毛发用组合物的烷氧基硅烷盐化合物的制备方法，其特征在于，所述保护基团是叔丁氧基羰基。
7.一种毛发用组合物，其特征在于，包含权利请求第1项及第2项中任何一项的用于毛发用组合物的烷氧基硅烷盐化合物作为活性成分。
8.根据权利要求7所述的毛发用组合物，其特征在于，所述烷氧基硅烷盐化合物具有自聚集性。
9.根据权利要求7所述的毛发用组合物，其特征在于，所述烷氧基硅烷盐化合物，基于毛发用组合物总重量，其含量为0.001至15重量％。
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| EP0342788A1 (en) * | 1988-04-13 | 1989-11-23 | Bridgestone Corporation | Synthetic resin composition |
| CN1468887A (zh) * | 2002-07-17 | 2004-01-21 | 黄振宏 | 有机硅季铵盐高分子聚合物制备与应用方法 |
| CN101791278A (zh) * | 2008-09-30 | 2010-08-04 | 欧莱雅 | 包含有机硅化合物、疏水性成膜聚合物、颜料和挥发性载体的化妆品组合物 |
| CN101889962A (zh) * | 2009-04-30 | 2010-11-24 | 莱雅公司 | 使用包含氨基三烷氧基硅烷或氨基三烯氧基硅烷化合物的组合物淡化和/或着色人角蛋白纤维和装置 |
| CN103619316A (zh) * | 2011-05-27 | 2014-03-05 | 莱雅公司 | 包含烷氧基硅烷、脂肪酯和有机硅的组合物及其化妆品用途 |
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| JP2012167055A (ja) * | 2011-02-15 | 2012-09-06 | Konishi Co Ltd | 毛髪化粧料 |
| FR2975593B1 (fr) | 2011-05-27 | 2013-05-10 | Oreal | Composition comprenant un alcoxysilane et un amidon modifie et son utilisation en cosmetique |
| JP6092545B2 (ja) * | 2012-08-22 | 2017-03-08 | 東レ・ダウコーニング株式会社 | カルボシロキサンデンドリマー構造および親水性基を有する共重合体およびその用途 |
| FR3009680B1 (fr) * | 2013-08-13 | 2018-05-18 | L'oreal | Composition comprenant un silane, un polymere fixant particulier et un polymere epaississant cellulosique |
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- 2016-09-23 KR KR1020160121880A patent/KR102634260B1/ko active IP Right Grant
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0342788A1 (en) * | 1988-04-13 | 1989-11-23 | Bridgestone Corporation | Synthetic resin composition |
| CN1468887A (zh) * | 2002-07-17 | 2004-01-21 | 黄振宏 | 有机硅季铵盐高分子聚合物制备与应用方法 |
| CN101791278A (zh) * | 2008-09-30 | 2010-08-04 | 欧莱雅 | 包含有机硅化合物、疏水性成膜聚合物、颜料和挥发性载体的化妆品组合物 |
| CN101889962A (zh) * | 2009-04-30 | 2010-11-24 | 莱雅公司 | 使用包含氨基三烷氧基硅烷或氨基三烯氧基硅烷化合物的组合物淡化和/或着色人角蛋白纤维和装置 |
| CN103619316A (zh) * | 2011-05-27 | 2014-03-05 | 莱雅公司 | 包含烷氧基硅烷、脂肪酯和有机硅的组合物及其化妆品用途 |
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| BR112018006513A2 (pt) | 2018-10-09 |
| KR102634260B1 (ko) | 2024-02-06 |
| TWI715637B (zh) | 2021-01-11 |
| US20180222927A1 (en) | 2018-08-09 |
| BR112018006513B1 (pt) | 2021-10-26 |
| TW201718607A (zh) | 2017-06-01 |
| KR20170038674A (ko) | 2017-04-07 |
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