CN1337875A - 洗发组合物 - Google Patents
洗发组合物 Download PDFInfo
- Publication number
- CN1337875A CN1337875A CN99814989A CN99814989A CN1337875A CN 1337875 A CN1337875 A CN 1337875A CN 99814989 A CN99814989 A CN 99814989A CN 99814989 A CN99814989 A CN 99814989A CN 1337875 A CN1337875 A CN 1337875A
- Authority
- CN
- China
- Prior art keywords
- hair
- washing composition
- active component
- sodium
- lauryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000002453 shampoo Substances 0.000 title claims abstract description 14
- 229930182558 Sterol Natural products 0.000 claims abstract description 15
- 150000003432 sterols Chemical class 0.000 claims abstract description 15
- 235000003702 sterols Nutrition 0.000 claims abstract description 15
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 14
- -1 dimethyl sulfopropyl betaine Chemical compound 0.000 claims description 61
- 238000005406 washing Methods 0.000 claims description 35
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 20
- 235000012000 cholesterol Nutrition 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 235000001014 amino acid Nutrition 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229940057950 sodium laureth sulfate Drugs 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 229960003237 betaine Drugs 0.000 claims description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 3
- JHJUUEHSAZXEEO-UHFFFAOYSA-M sodium;4-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHJUUEHSAZXEEO-UHFFFAOYSA-M 0.000 claims description 3
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 3
- MKDRQQLTZMMMHY-UHFFFAOYSA-N 2-hydroxyethylsulfonyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OS(=O)(=O)CCO MKDRQQLTZMMMHY-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 claims description 2
- 229940063953 ammonium lauryl sulfate Drugs 0.000 claims description 2
- CESHKJCQQFFQQQ-UHFFFAOYSA-N azane 2-dodecyl-2-sulfobutanedioic acid Chemical compound N.CCCCCCCCCCCCC(S(O)(=O)=O)(C(O)=O)CC(O)=O CESHKJCQQFFQQQ-UHFFFAOYSA-N 0.000 claims description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical group CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 claims description 2
- 229940094506 lauryl betaine Drugs 0.000 claims description 2
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 claims description 2
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 claims description 2
- 235000010334 sodium propionate Nutrition 0.000 claims description 2
- 239000004324 sodium propionate Substances 0.000 claims description 2
- 229960003212 sodium propionate Drugs 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- 125000002091 cationic group Chemical group 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 241000282372 Panthera onca Species 0.000 description 10
- 230000008021 deposition Effects 0.000 description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- 230000003750 conditioning effect Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 241001597008 Nomeidae Species 0.000 description 7
- 239000003292 glue Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 229940106189 ceramide Drugs 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 235000021313 oleic acid Nutrition 0.000 description 5
- 229960002969 oleic acid Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004475 Arginine Substances 0.000 description 4
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 4
- 244000241257 Cucumis melo Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 4
- 235000009697 arginine Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
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- 150000002430 hydrocarbons Chemical class 0.000 description 4
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- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 4
- 150000003904 phospholipids Chemical class 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003512 tertiary amines Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- 229920000289 Polyquaternium Polymers 0.000 description 3
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
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- 238000005457 optimization Methods 0.000 description 3
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 208000001840 Dandruff Diseases 0.000 description 2
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Abstract
一种洗发组合物,含有一种活性成分和多层泡,其特征在于多层泡基本上由阴离子表面活性剂和甾醇组成。
Description
发明领域
本发明涉及洗发组合物，更具体的是掺入多薄层气泡的洗发组合物，该组合物对掺入其中的活性成分提供改善的包胶和输送。
发明背景和现有技术
当用掺入活性成分的漂去产品处理头发时，相当数量的活性成分将被漂洗掉，特别是如果活性成分是可溶于表面活性剂的情况时。研究表明，在简单洗发组合物的情况下，这时活性成分溶解在产品中的表面活性剂胶粒中，保留水平可能低至5％。
与将活性成分掺入头发处理组合物中相关的另一问题是它们可能对如热、氧化、光、湿、pH和(特别是在营养活性成分如氨基酸的情况下)微生物的攻击这样的因素敏感。它们可能倾向于与配方中的其它成分发生反应。
希望提供一种对掺入其中的活性成分具有改善的包胶和输送功能的洗发组合物，因为这样将能提供更好的活性成分效能，并提供减少产品中昂贵活性成分含量的选择余地，进而节约了成本。
脂质体即脂质粒的制造和它们在包胶和输送很多种物质方面的用途是已知的(例如见New，R.R.C.，Liposomes-a practicalapproach，Oxford University Press)。大多数经常使用的脂质体是由磷脂制备的单层气泡。其原因是磷脂是天然膜的基本结构组分。然而磷脂对酶的降解、自动氧化和酸性pH条件是敏感的，并且制造过程非常昂贵。此外，磷脂泡较易碎，容易破裂、聚结和释放出其中被包胶的物质。
为了避免这些缺点，有趋势朝向研究发展由各种脂类和表面活性剂制造的泡体。例如，WO-A-9 219 214描述了一种用于人类皮肤的人工致软方法的水包油乳液组合物，其中含有的脂泡由聚氧亚烷基烷基醚、甾醇、季铵化合物和任选的非表面活性油制成。WO 95/23578叙述了一种头发调理剂，其中多层泡通过掺混阳离子表面活性剂和胆固醇形成。
发明概述
本发明已令人惊奇地发现，当含有阴离子表面活性剂的洗发基质加入到胆固醇的悬浮液中时，便可自发地形成多层泡。该多层泡贮存时稳定，并且可用于包胶洗发剂中的活性成分，因而增强了洗发剂中活性成分的效能和输送。
因此，本发明提供了含有活性成分和多层泡的洗发组合物，其特征是该多层泡基本上由阴离子表面活性剂和甾醇组成。
本发明详述
本发明人已经发现将甾醇水分散液加入到含有至少一种阴离子表面活性剂的洗发剂基质中使诱导多层泡的形成。这样产生的结构用常规对照显微技术便可容易地观察到。
将固体甾醇(适当的是固体胆固醇)加入水中，加热，高剪切混合，并且在搅拌的同时令混合物冷至室温，可以制得合适的甾醇(合适的是胆固醇)的含水分散液。
制备这种水分散液的适当方法的具体实例可描述如下：
(a)加热水至60至80℃；
(b)加入固体胆固醇，同时用磁搅拌器匀速搅拌1小时；
(c)高剪切下混合30秒(适当的仪器是Ystral混合器，5mm探针，设置7)；
(d)放回到磁搅拌器上并搅拌直到冷却，经过这段时间，混合物是均匀的分散液了。
根据本发明形成的多层泡贮存时稳定，并且可用于对洗发剂中的活性成分包胶，进而增强了洗发剂中的活性成分的效能和输送。对根据本发明制得的洗发组合物进行显微研究表明，这种被掺入的活性成分至少在该多层泡中部分包胶。优选使这种包胶作用最优化，以便自本发明洗发组合物中的沉积增强作用最有效，特别是涉及到可溶的或被溶解的活性组分。已经发现，活性成分的最优化包胶作用通常发生在于多层泡形成之前就加入欲包胶的活性成分的情况下。这一方法能使得在多层泡形成时发生活性成分的最优化掺入。
因此，根据本发明，制备洗发组合物的优选方法包括下列步骤：
(i)形成甾醇的水分散液；
(ii)向所得到的水分散液中加入活性成分；和
(iii)向(ii)中得到的混合物中加入包含至少一种阴离子表面活性剂的洗发剂基质；
本发明的洗发组合物的成分可以更详细地描述特征如下：
甾醇
甾醇是本发明洗发组合物的基本组分。甾醇在Hackh’s ChemicaiDictionary第4版第638页(McGraw-Hill，New York；1972)中描述。用于本发明的一种优选甾醇是胆固醇。
在洗发组合物中，甾醇、优选胆固醇的适当含量(重量百分数)是0.005％至2％，优选0.00625％至1％，最优选是0.025％至0.05％，以洗发组合物的总重量为基础。
活性成分
合适的活性成分中包括：
(i)防晒剂。合适的防晒剂中有：樟脑衍生物，二苯酮化合物如4，4’-四羟基二苯酮，以Urinul D50商售，和2-羟基-4-甲氧基二苯酮，以Eusolex 4360商售，二苯甲酰基甲烷衍生物如叔丁基-4-甲氧基二苯甲酰基甲烷，以Parsol 1789商售，和异丙基二苯甲酰基甲烷，以Eusolex 8020商售。优选的防晒物质是肉桂酸盐，如2-乙基己基-对-甲氧基肉桂酸盐，以Parsol MCX商售，2-乙氧基乙基-对-甲氧基肉桂酸盐，以Giv-Tan F商售，和异戊基-对-甲氧基肉桂酸盐，以Neo-Hel iopan E1000商售。
(ii)去头屑剂，如吡啶噻酮(pyrithione)锌，和其他1-羟基吡啶酮。优选的去头屑剂是1-羟基-2-吡啶酮衍生物，称为Piroctone olamine，化学名称是1-羟基-4-甲基-6-(2，4，4-三甲基戊基)-2-吡啶酮单乙醇胺盐，它以商品名OCTIPIROX由Hoechst AG出售。
(iii)天然发根营养素，如氨基酸和糖类。适当的氨基酸的实例包括精氨酸，半胱氨酸，谷氨酰胺，谷氨酸，异亮氨酸，亮氨酸，蛋氨酸，丝氨酸和缬氨酸，和/或其前体和它们的衍生物。氨基酸可以单独一种、混合物形式或以肽如二肽或三肽形式加入。氨基酸还可以蛋白质水解产物、如角蛋白或胶原蛋白水解产物形式加入。合适的糖类是葡萄糖，右旋糖和果糖。这些可以单独加入或以例如水果提取物形式加入。特别优选的氨基酸营养物是精氨酸。
(iv)头发纤维补益剂。实例有：
-神经酰胺类，用于湿润纤维并保持角质层完整性。神经酰胺可由天然来源萃取、或作为合成的神经酰胺和假神经酰胺得到。优选的神经酰胺是神经酰胺II，购自Quest。神经酰胺混合物也可能适用，如神经酰胺LS，购自Serobiologiques实验室。
-脂肪酸，用于角质层修复和防止损伤。实例有支链脂肪酸，如18-甲基二十碳酸和这一系列的其他同系物，直链脂肪酸如硬脂酸，肉豆蔻酸和棕榈酸，和不饱和脂肪酸，如油酸，亚油酸，亚麻酸和花生四烯酸。优选的脂肪酸是油酸。脂肪酸可以单独一种、作为混合物，或以得自例如羊毛脂的萃取物的掺合物形式加入。
也可使用上述活性成分中任何成分的混合物。特别优选的结合是精氨酸和油酸。
存在的活性成分的浓度通常是0.005％至5％，优选0.085％至2％，基于洗发组合物总重量按活性成分总重量计算。
阴离子表面活性剂
适合于本发明洗发组合物的阴离子表面活性剂包括烷基硫酸盐，烷基醚硫酸盐，烷芳基磺酸盐，烷酰基羟乙磺酸盐，烷基琥珀酸盐，烷基磺基琥珀酸盐，N-烷酰基肌氨酸盐，烷基磷酸盐，烷基醚磷酸盐，烷基醚羧酸盐，α-烯烃磺酸盐，和酰基甲基牛磺酸盐(taurate)，特别它们的钠、镁、铵和单-、二-和三乙醇胺盐。烷基和酰基通常含有8至18个碳原子，且可以是不饱和的。烷基醚硫酸盐、烷基醚磷酸盐和烷基醚羧酸盐每个分子可含有1至10个亚乙氧基或亚丙氧基单元，优选每个分子含2至3个亚乙氧基单元。
适当的阴离子表面活性剂的实例包括月桂基硫酸钠、月桂基醚硫酸钠、月桂基磺基琥珀酸铵、月桂基硫酸铵、月桂基醚硫酸铵、十二烷基苯磺酸钠、十二烷基苯磺酸三乙醇胺、椰子酰基(cocoyl)羟乙磺酸钠、月桂酰基羟乙磺酸钠、N-月桂基肌氨酸钠、和它们的混合物。
阴离子表面活性剂在本发明洗发组合物中的含量通常是组合物总重量的3-50％，优选3-30％，更优选5-20％。
任选成分
-其他表面活性剂
本发明的洗发组合物还可以含有辅助表面活性剂，以有助于使组合物具有美学的、物理的或清洗方面的性能。优选实例包括两性、两性离子和/或非离子表面活性剂，其含量可以是0％至约10％重量比，以洗发组合物的总重量为基础。
两性或两性离子表面活性剂的实例包括烷基胺氧化物，烷基甜菜碱，烷基酰胺基丙基甜菜碱，烷基磺基甜菜碱(sultains)，烷基甘氨酸盐，烷基羧基甘氨酸盐，烷基两性(ampho)丙酸盐，烷基两性甘氨酸盐，烷基酰胺基丙基羟基磺基甜菜碱，酰基牛磺酸盐和酰基谷氨酸盐，其中烷基和酰基有8至19个碳原子。用于本发明洗发剂的典型的两性和两性离子表面活性剂包括月桂基胺氧化物，椰子二甲基磺基丙基甜菜碱和优选的月桂基甜菜碱，椰子酰胺基丙基甜菜碱，椰子两性丙酸钠，和它们的混合物。
可以包括在本发明洗发组合物中的代表性非离子表面活性剂包括脂肪族(C8-C18)伯或仲直链或支链醇或酚与亚烷基氧化物、通常是环氧乙烷的缩合产物，并且通常具有6至30个亚乙氧基。
其他代表性非离子物包括单-或二烷基烷醇酰胺。实例包括椰子单-或二乙醇酰胺和椰子单-异丙醇酰胺。
可以包括在本发明的洗发组合物其他非离子表面活性剂是烷基聚糖苷(APG)。典型地，APG中含有一个连结(任选地经过一个桥基)到一个或多个糖基建筑块上的烷基。优选的APGs由下式定义：
RO-(G)n其中R是支链或直链烷基，其可以是饱和的或不饱和的，并且G是糖基。
R可表示约C5至约C20的平均烷基链长。优选R表示约C8至C12的平均烷基链长。最优选的R值在约9.5至约10.5之间。G可选自C5或C6单糖基，且优选为葡糖苷。G可选自葡萄糖、木糖、乳糖、果糖、甘露糖和它们的衍生物。优选G是葡萄糖。
聚合度n可具有约1至10或更大的值。优选n的值在约1.1至约2之间。最优选该n值在约1.3至约1.5之间。
本发明所用的合适的烷基聚糖苷是商业上可购得的，包括例如称为Oramix NS 10(购自Seppic)、Plantaren 1200和Plantaren 2000(购自Henkel)的物质。
也可使用上述任何非离子表面活性剂的混合物。
作为该洗发组合物中被乳化组分的乳化剂，例如被乳化的硅氧烷颗粒，还可存在其他表面活性剂。这可以是和上述阴离子表面活性剂或任何复合表面活性剂相同的，也可以是不同的。
合适的乳化表面活性剂是本领域中熟知的，并且包括阴离子和非离子表面活性剂。用作例如硅氧烷颗粒的物质的乳化剂的阴离子表面活性剂的实例有烷芳基磺酸盐，例如十二烷基苯磺酸钠、烷基硫酸盐如月桂基硫酸钠，烷基醚硫酸盐如月桂基醚硫酸钠nEO，其中n是1至20烷基苯酚醚硫酸盐如辛基苯酚醚硫酸盐nEO，其中n是1至20，以及磺基琥珀酸盐，如二辛基磺基琥珀酸钠。
用作如硅氧烷颗粒材料的乳化剂的非离子表面活性剂的实例有烷基苯酚乙氧化物，如壬基苯酚乙氧化物nEO，其中n是1至50，醇乙氧化物如月桂基醇nEO，其中n是1至50，酯乙氧化物，如聚氧亚乙基单硬脂酸盐，其中氧亚乙基单元的数目的是1至30。
本发明洗发组合物中表面活性剂的总量(包括任何复合表面活性剂和/或任何乳化剂)通常是总洗发组合物的0.1至50％重量比，优选5至30％，更优选10％至25％重量。
-调理剂
本发明洗发组合物还可以包含一种或多种调理剂。这里所用的术语“调理剂”包括用来给予头发和/或皮肤特别调理益处的任何物质。例如在用以洗头发组合物中，合适的物质是能够给予一种或多种有关光泽、柔软、梳理性、湿处理、抗静电性、抗损伤保护、厚实(body)、蓬松(volume)，可定型性和易调理性等益处的那些物质。
用于本发明的优选的调理剂包括乳化的硅氧烷，用以赋于头发例如湿和干调理益处，如柔软、润滑感和易于梳理。
硅氧烷在组合物的含水基质中是不溶的，因而以被乳化形式存在，硅氧烷以被分散颗粒形式存在。
合适的硅氧烷包括聚二有机硅氧烷，具体是聚二甲基硅氧烷，其CTFA名称为“dimethicone”。也适合于本发明组合物(具体是洗发剂和调理剂)的是具有羟端基的聚二甲基硅氧烷，其CTFA名称是“dimethiconol”。也适合于本发明组合物的有硅氧烷胶。“硅氧烷胶”表示分子量为200,000至1,000,000的聚二有机硅氧烷，具体实例包括聚二甲基硅氧烷胶、端羟基聚二甲基硅氧烷胶、聚二甲基硅氧烷/二苯基/甲基乙烯基硅氧烷共聚物，聚二甲基硅氧烷/甲基乙烯基硅氧烷共聚物和它们的混合物。实例包括例如在WO 96/31188中所述的低交联度的那些物质。这些物质可以赋予头发厚实(body)、蓬松(Volume)和可定型性，以及好的湿和干调理性能。
被乳化的硅氧烷本身(不是乳液或最终头发调理组合物)的粘度通常至少是10,000 cst。通常，我们已发现调理效能随着粘度增加而增加。因此，硅氧烷本身的粘度优选是至少60,000 cst，最优选至少500,000 cst，理想地至少1,000,000 cst。为易于配制，优选该粘度不超过109cst。
通常，用于本发明洗发剂和头发调理剂中的乳化的硅氧烷在组合物中具有平均硅氧烷颗粒大小为小于30、优选小于20、更优选小于10微米。我们已经发现，减小颗粒大小通常改进调理效能。最优选组合物中的被乳化的平均硅氧烷颗粒大小为小于2微米，理想的是在0.01至1微米之间。平均硅氧烷颗粒大小≤0.15微米的硅氧烷乳液通常称为微乳液。
颗粒大小可以通过激光溅射技术使用Malvern Instruments公司的2600D Particle Sizer仪器测量。
用于本发明的合适的硅氧烷乳液也可以预乳化形式购得。
适合的预形成乳液的实例包括乳液DC 2-1766，DC 2-1784和微乳液DC 2-1865和DC 2-1870，可由Dow Corning公司购得。这些都是端羟基二甲基硅氧烷的乳液/微乳液。交联的硅氧烷胶也可以预乳化形式购得，其优点是易于形成。优选实例是购自Dwo Corning公司的DC X2-1787材料，它是交联的端羟基二甲基硅氧烷胶的乳液。
进一步优选的实例是购自Dow Corning公司的DC X2-1391材料，它是交联的端羟基二甲基硅氧烷胶的微乳液。
包含在本发明洗发剂和调理剂中的更优选的一类硅氧烷是氨基功能化的硅氧烷。“氨基功能化的硅氧烷”是指含有至少一个伯、仲或叔胺基、或一个季铵基的硅氧烷。
氨基功能化的硅氧烷的预形成乳液也可以自硅氧烷油的供应商如Dow Corning和GE公司购得。具体实例包括DC 929阳离子乳液、DC 938阳离子乳液和非离子乳液DC 2-7224、DC 2-8467、DC 2-8177和DC 2-8154(均购自Dow Corning)。
掺入本发明组合物中的硅氧烷的量取决于所期望的调理水平和所使用的物质。优选的量是总组合物的0.01至约10％重量比，尽管该限制不是绝对的。低限决定于达到调理的最低含量而上限决定于要避免使头发和/或皮肤不可接受的油滑时的最大含量。我们已经发现，硅氧烷的量占总组合物的0.5至1.5％重量是特别合适的含量。
另一类优选的调理剂是全烷(烯)基烃类物质，用以提高头发的厚实(body)、蓬松(Volume)和可定型性。
EP 567 326和EP 498 119描述适用的全烷(烯)烃类物质，目的是使头发具有可定型性和增加的厚实性(body)。优选的物质是聚异丁烯物质，可由Presperse公司以PERMETHYL商品名购得。
掺入到本发明组合物中的全烷(烯)基烃类物质的量取决于所期望的body和Volume增强程度以及所用的具体物质。优选的量是总组合物的0.01至约10％重量，尽管这些限制不是绝对的。低限决定于达到body和Volume增强效果的最小含量，而上限决定于避免使头发不可接受地干硬的最大含量。我们已经发现，全烷(烯)基烃类物质的含量为总组合物的0.5至2％重量时是特别合适的含量。
-阳离子沉积聚合物
阳离子沉积聚合物是可被包含在本发明洗发组合物中的优选成分，用以增加洗发剂的调理效能。“沉积聚合物”是指一种物质，在使用时，它可增强活性成分和/或调理成分(如硅氧烷)自洗发组合物中沉积到所希望的部位、即头发和/或头皮上。
沉积聚合物可以是均聚物或由两种或多种单体类型形成。聚合物的分子量通常在5000和10,000,000之间，通常至少为10,000，并且优选在100,000和2,000,000之间。该聚合物含有阳离子含氮基团，如季铵或质子化氨基，或它们的混合物。
阳离子含氮基团通常作为在该沉积聚合物中总单体单元的一部分上的取代基存在。于是，当该聚合物不是均聚物时，它可含有间隔基非阳离子单体单元。这类聚合物描述在CTFA Cosmetic IngredientDirectory，第3版。选择阳离子和非阳离子单体单元的比率，以使得聚合物具有所需范围的阳离子电荷密度。
合适的阳离子沉积聚合物包括例如具有阳离子胺或季铵官能团的乙烯基单体和水溶性间隔基单体如(甲基)丙烯酰胺、烷基和二烷基(甲基)丙烯酰胺、(甲基)丙烯酸烷基酯、乙烯基己内酯和乙烯基吡咯烷酮的共聚物。烷基和二烷基取代的单体优选具有C1-C7烷基，更优选C1-3烷基。基他合适的间隔基包括乙烯基酯、乙烯基醇、马来酸酐、丙二醇和乙二醇。
阳离子胺可以是伯、仲或叔胺，取决于组合物的具体类别和pH。通常是仲和叔胺、尤其叔胺是优选的。
胺取代的乙烯基单体和胺可以以胺形式聚合，然后通过季铵化转为铵。
阳离子沉积聚合物可以含有衍生自胺-和/或季铵-取代的单体和/或相容的间隔基单体的单体单元的混合物。
合适的阳离子沉积聚合物包括例如：
-1-乙烯基-2-吡咯烷酮和1-乙烯基-3-甲基-咪唑鎓盐(如盐酸盐)的共聚物，在工业上被CTFA(the Cosmetic，Toiletry，andFragrance Association)称为Polyquaternium-16。该物质可由BASFWyandotte公司(parsippany，NJ，USA)以商品名LUVIQUAT(例如LUVIQUAT FC 370)购得。
-1-乙烯基-2-吡咯烷酮和甲基丙烯酸二甲氨基乙酯的共聚物，在工业上被CTFA称作Polyguaternium-11。该物质可由Gaf公司(Wayne，NJ，USA)以商品名GAFQUAT(如GAFQUAT 755N)购得。
-含二烯丙基季铵的阳离子聚合物包括例如二甲基二烯丙基氯化铵均聚物和丙烯酰胺与二甲基二烯丙基氯化铵的共聚物，在工业上被CTFA分别称作Polyquaternium 6和Polyquaternium 7。
-具有3至5个碳原子的不饱和羧酸的均聚物和共聚物的氨基烷基酯的无机酸盐(如USP 4,009,256中所述)。
-阳离子聚丙烯酰胺(如在WO 95/22311中所述)
可以使用的其他阳离子沉积聚合物包括阳离子多糖聚合物，如阳离子纤维素衍生物、阳离子淀粉衍生物和阳离子瓜耳胶衍生物。
适用于本发明组合物的阳离子多糖聚合物包括具有下式的那些
A-O-[R-N+(R1)(R2)(R3)X-]，其中A是无水葡萄糖残基，如淀粉或纤维素无水葡萄糖残基。R是亚烷基，氧亚烷基，聚氧亚烷基，或羟亚烷基，或它们的组合。R1、R2、和R3独立表示烷基、芳基、烷芳基、芳烷基、烷氧烷基或烷氧芳基，各基团含有至多约18个碳原子。每个阳离子部分的碳原子总数(即R1、R2和R3中碳原子之和)优选为约20或更少，X是抗衡阴离子。
阳离子纤维素可由Amerchol公司(Edison，NJ，USA)自其PolymerJR(商标)和LR(商标)聚合物系列、作为羟乙基纤维素与三甲胺取代的环氧化物反应生成的盐、在工业上(CTFA)称为Polyquaternium10中购得。其他类型的阳离子纤维素包括由羟乙基纤维素与月桂基二甲基铵取代的环氧化物反应生成的聚合的季铵盐，在工业上(CTFA)称其为Polyquaternium 24。这些物质可由Amerchol公司(Edison，NJ，USA)以商品名Polymer LM-200购得。
其他合适的阳离子多糖聚合物包括含季氮原子的纤维素醚(如USP 3,962,418中所述)，和醚化的纤维素和淀粉的共聚物(如USP3,958,581中所述)。
可使用的特别适合的阳离子多糖聚合物类型是阳离子瓜耳胶衍生物，如瓜耳羟丙基trimonium氯化物(可由Rhone-Poulenc按其JAGUAR商标系列购得)。
实例有JAGUAR C13S，其具有阳离子基的低度取代和高粘度；JAGUAR C15，其具有中度取代和低粘度；JAGUAR C17(高度取代，高粘度)；JAGUAR C16，其是含有低含量取代基以及阳离子季铵基的羟丙基化的阳离子瓜耳衍生物；以及JAGUAR 162，其是具有低度取代的高透明、中粘度瓜耳。
优选该阳离子沉积聚合物选自阳离子纤维素和阳离子瓜耳衍生物，特别优选的沉积聚合物是JAGUAR C13S，JAGUARC15，JAGUAR C17和JAGUAR C16以及JAGUAR C162。
阳离子沉积聚合物的含量通常是占总组合物的0.001至5％，优选约0.01至1％，更优选约0.02％至约0.5％重量。
作为包含在本发明组合物中的其他任选组分，除水之外，可提及的还有：pH调节剂、粘度调节剂、珠光剂、遮光剂、悬浮剂、防腐剂、着色剂、染料、蛋白质、药草和植物提取物、多醇和其他润湿和/或调理剂。
现通过参照下述实施例进一步说明本发明的实施方案。除非另有指明，给出的所有的量都是基于组合物总重量的重量百分数。
实施例
制备具有下列成分的洗发组合物：
成分 ％重量
月桂基醚硫酸钠(2EO) 9
椰子酰胺丙基甜菜碱 5
L-精氨酸 0.2
胆固醇 0.05
油酸 0.01
水，微量组分 至100
将胆固醇溶于60℃水中，在室温搅拌过液，制得组合物。然后加入油酸和精氨酸，接着是其他组分，用Ystral混合器将各成分结合在一起并形成乳液。
观察到该组合物含有多层泡，这一结果是这样证实的：取其试样1ml，在13,000rpm离心15分钟，通过×20倍偏光显微镜考察所得到的沉淀物。在显微镜下明显看到多层泡的族群，可由其“MalteseCross”外观区分出来。
对于离心和再离心作用，多层泡是稳定的。因此，当需要时，这就提供了用以生产更加浓缩的多层泡分散液以掺入头发制剂中的方便途径。
Claims (6)
1.包含活性成分和多层泡的洗发组合物，其特征在于该多层泡基本上由阴离子表面活性剂和甾醇组成。
2.根据权利要求1的洗发组合物，其中甾醇是胆固醇。
3.根据权利要求1或2的洗发组合物，其中活性成分选自氨基酸、脂肪酸和它们的混合物。
4.根据前述权利要求中任一项的洗发组合物，其中阴离子表面活性剂选自月桂基硫酸钠，月桂基醚硫酸钠，月桂基磺基琥珀酸铵，月桂基硫酸铵，月桂基醚硫酸铵，十二烷基苯磺酸钠，十二烷基苯磺酸三乙醇胺，椰子酰基羟乙磺酸钠，月桂酰基羟乙磺酸钠，N-月桂基肌氨酸钠，和它们的混合物。
5.根据前述权利要求中任一项的洗发组合物，还含有两性或两性离子表面活性剂，选自月桂基胺氧化物，椰子基二甲基磺基丙基甜菜碱和优选的月桂基甜菜碱，椰子酰氨基丙基甜菜碱，椰子两性丙酸钠，和它们的混合物。
6.制备含有多层泡和活性成分的洗发组合物的方法，该方法包括下列步骤：
(i)形成甾醇的水分散液；
(ii)向得到的水分散液中加入活性成分，和
(iii)向(ii)中得到的混合物中加入含有至少一种阴离子表面活性剂的洗发剂基质。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9824024.5A GB9824024D0 (en) | 1998-11-03 | 1998-11-03 | Shampoo compositions |
| GB9824024.5 | 1998-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1337875A true CN1337875A (zh) | 2002-02-27 |
| CN1217653C CN1217653C (zh) | 2005-09-07 |
Family
ID=10841742
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN998149896A Expired - Fee Related CN1217653C (zh) | 1998-11-03 | 1999-10-27 | 洗发组合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20020119113A1 (zh) |
| EP (1) | EP1126819A1 (zh) |
| JP (1) | JP2002528481A (zh) |
| CN (1) | CN1217653C (zh) |
| AR (1) | AR021070A1 (zh) |
| AU (1) | AU756682B2 (zh) |
| BR (1) | BR9915008A (zh) |
| CA (1) | CA2350249A1 (zh) |
| GB (1) | GB9824024D0 (zh) |
| PL (1) | PL347941A1 (zh) |
| WO (1) | WO2000025741A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4001310B2 (ja) * | 1999-09-30 | 2007-10-31 | 株式会社資生堂 | 脂質複合体及びこれを含有する外用組成物 |
| FR2816834B1 (fr) * | 2000-11-20 | 2005-06-24 | Oreal | Composition de traitement des fibres keratiniques comprenant un polymere polyurethane associatif cationique et un agent protecteur ou conditionneur |
| JP2005515215A (ja) | 2001-12-21 | 2005-05-26 | ローディア インコーポレイティド | 成分を懸濁させるための安定な界面活性剤組成物 |
| EP1496887B1 (en) * | 2002-04-22 | 2016-08-03 | The Procter & Gamble Company | Personal care compositions comprising a zinc containing material in an aqueous surfactant composition |
| US8349302B2 (en) * | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
| US8367048B2 (en) * | 2002-06-04 | 2013-02-05 | The Procter & Gamble Company | Shampoo containing a gel network |
| US8361450B2 (en) * | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
| US8349301B2 (en) | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network |
| US8470305B2 (en) * | 2002-06-04 | 2013-06-25 | The Procter & Gamble Company | Shampoo containing a gel network |
| US8361448B2 (en) * | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network |
| US9381382B2 (en) * | 2002-06-04 | 2016-07-05 | The Procter & Gamble Company | Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network |
| US8491877B2 (en) * | 2003-03-18 | 2013-07-23 | The Procter & Gamble Company | Composition comprising zinc-containing layered material with a high relative zinc lability |
| CA2524589A1 (en) * | 2003-05-07 | 2004-11-18 | Ifac Gmbh & Co. Kg | Compositions for the targetted release of fragrances and aromas |
| EP1670426A4 (en) * | 2003-07-22 | 2009-12-09 | Rhodia | NEW BRANCHED SULFATES FOR USE IN PERSONAL CARE FORMULATIONS |
| JP4331625B2 (ja) * | 2004-01-23 | 2009-09-16 | 日本精化株式会社 | 毛髪化粧料 |
| JP2007532765A (ja) * | 2004-04-15 | 2007-11-15 | ローディア インコーポレイティド | 組織化界面活性剤組成物 |
| CA2577460C (en) * | 2004-08-17 | 2013-05-14 | Rhodia, Inc. | Low ph structured surfactant compositions |
| US8828364B2 (en) * | 2007-03-23 | 2014-09-09 | Rhodia Operations | Structured surfactant compositions |
| JP5026205B2 (ja) * | 2007-09-18 | 2012-09-12 | 日本メナード化粧品株式会社 | 毛髪用組成物 |
| AU2009312929A1 (en) * | 2008-11-07 | 2010-05-14 | Unilever Plc | Conditioning shampoo comprising an aqueous conditioning gel phase in the form of vesicles |
| JP2013529659A (ja) | 2010-07-08 | 2013-07-22 | ユニリーバー・ナームローゼ・ベンノートシヤープ | ヘアケア組成物 |
| CA2850039C (en) | 2011-10-07 | 2017-03-07 | The Procter & Gamble Company | Shampoo composition containing a gel network |
| EP2833975B1 (en) * | 2012-04-02 | 2017-03-22 | DSM IP Assets B.V. | Shampoo preparations |
| US10945935B2 (en) | 2016-06-27 | 2021-03-16 | The Procter And Gamble Company | Shampoo composition containing a gel network |
| CN112261931B (zh) | 2018-06-05 | 2023-12-08 | 宝洁公司 | 透明清洁组合物 |
| JP7328336B2 (ja) | 2018-12-14 | 2023-08-16 | ザ プロクター アンド ギャンブル カンパニー | シート状マイクロカプセルを含むシャンプー組成物 |
| US11896689B2 (en) | 2019-06-28 | 2024-02-13 | The Procter & Gamble Company | Method of making a clear personal care comprising microcapsules |
| JP7453395B2 (ja) | 2020-02-14 | 2024-03-19 | ザ プロクター アンド ギャンブル カンパニー | 中に懸濁された審美的設計を有する液体組成物の保管に適合されたボトル |
| US11633072B2 (en) | 2021-02-12 | 2023-04-25 | The Procter & Gamble Company | Multi-phase shampoo composition with an aesthetic design |
| US12053130B2 (en) | 2021-02-12 | 2024-08-06 | The Procter & Gamble Company | Container containing a shampoo composition with an aesthetic design formed by bubbles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4911928A (en) * | 1987-03-13 | 1990-03-27 | Micro-Pak, Inc. | Paucilamellar lipid vesicles |
| US5032457A (en) * | 1988-03-03 | 1991-07-16 | Micro Vesicular Systems, Inc. | Paucilamellar lipid vesicles using charge-localized, single chain, nonphospholipid surfactants |
| GB9811754D0 (en) * | 1998-06-01 | 1998-07-29 | Unilever Plc | Hair treatment compositions |
-
1998
- 1998-11-03 GB GBGB9824024.5A patent/GB9824024D0/en not_active Ceased
-
1999
- 1999-10-27 JP JP2000579185A patent/JP2002528481A/ja not_active Withdrawn
- 1999-10-27 PL PL99347941A patent/PL347941A1/xx not_active Application Discontinuation
- 1999-10-27 EP EP99955935A patent/EP1126819A1/en not_active Ceased
- 1999-10-27 BR BR9915008-5A patent/BR9915008A/pt not_active Application Discontinuation
- 1999-10-27 CA CA002350249A patent/CA2350249A1/en not_active Abandoned
- 1999-10-27 AU AU12683/00A patent/AU756682B2/en not_active Ceased
- 1999-10-27 CN CN998149896A patent/CN1217653C/zh not_active Expired - Fee Related
- 1999-10-27 WO PCT/EP1999/008326 patent/WO2000025741A1/en not_active Application Discontinuation
- 1999-11-03 US US09/433,162 patent/US20020119113A1/en not_active Abandoned
- 1999-11-03 AR ARP990105557A patent/AR021070A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000025741A1 (en) | 2000-05-11 |
| CA2350249A1 (en) | 2000-05-11 |
| JP2002528481A (ja) | 2002-09-03 |
| US20020119113A1 (en) | 2002-08-29 |
| AU756682B2 (en) | 2003-01-23 |
| AU1268300A (en) | 2000-05-22 |
| AR021070A1 (es) | 2002-06-12 |
| CN1217653C (zh) | 2005-09-07 |
| EP1126819A1 (en) | 2001-08-29 |
| PL347941A1 (en) | 2002-04-22 |
| BR9915008A (pt) | 2001-08-07 |
| GB9824024D0 (en) | 1998-12-30 |
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