CN1106660A - 表皮用制剂和其制备方法 - Google Patents
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Abstract
本发明给出了一种表皮用制剂和其制备方法,该
制剂包括曲酸和/或其衍生物,紫外线吸收剂,该制
剂稳定性增强,并具有持久效能。稳定性的增强是通
过向制剂中添加至少一种选自醇和多酚的物质而实
现的。
Description
本发明涉及一种表皮用制剂,以及这种制剂的制备方法,该制剂含有曲酸和/或其衍生物,紫外线吸收剂,它还至少含有一种选自醇和多酚的物质,该物质用于增强曲酸和/或其衍生物的稳定性并使其效能持续长久。
表皮制剂的形式通常有两种:O/W乳剂(水包油)和W/O乳剂(油包水),它们的水与油的比例不同且物理性能有异。但是,借助于表面活性剂,可以稳定地乳化和分散油相或水相,从而两种制剂均为均匀的制剂。
对曲酸和其衍生物本发明人进行过长期的研究,它们是公知的具有各种优异性能的有用试剂,如下文献均有报导:日本未审专利公开号55-157509,日本审查专利公开号S56-18569,S58-22151,S58-22152,S58-34446,S60-7961,S60-9722和S60-10005,日本未审专利公开号S60-137253,日本审查专利公开号S61-10447和S61-60801,日本未审专利公开号S62-5909,日本审查专利公开号S62-3820和S63-27322,日本未审专利公开号H1-132502和日本审查专利公开号H5-30422。
但是,曲酸和其衍生物(以下有时仅称之为曲酸)也是公知的自身稳定性较差的试剂。特别是,当曲酸被掺入上述O/W乳剂或W/O乳剂中时,需要相当复杂的技术来设计一种适宜的配方。因此,对于配制含曲酸的制剂来说,一个紧迫的任务是发展以下一种技术:该技术可使含曲酸的制剂具有足够的稳定性以耐受严重的分布机制,且当将其施加于皮肤上时不会有令人不快的感觉。
在各种表皮制剂中含有曲酸时,这些制剂被置于可能暴露于紫外线的条件至变化程度,紫外线可能是其变色或分解的外部原因。因此,可推断出应混合一种适量的紫外线吸收剂来抑制由紫外线辐射造成的损害。
例如,以下文献给出了相应的实例,日本未审专利公开号S62-108804和S64-83008,日审查专利公开号H4-46924。
这些紫外线吸收剂多数存在溶解性问题,它们还会从制剂中离析出来,故难以完全显示其紫外线吸收能力,从而导致曲酸的稳定性降低。
为了克服上述缺陷,可适当地采用一些加溶剂。但是,大量使用油性加溶剂会带来如下问题:当将制剂施加于皮肤上时有一种令人不愉快的感觉如粘着感。
此外,业已清楚,热也会影响曲酸的稳定性。目前,还没有解决由热引起的问题。
进而,非离子表面活性剂为一种适宜的表面活性剂,将其形成含曲酸的外用制剂并使用该制剂后,能抑制色变,并有一种令人愉快的感觉而对皮肤无害,但是,非离子表面活性剂与离子型表面活性剂相比其乳化能力较弱,在高极性成分存在下乳化能力会降低,或者受pH值的影响。因而,在通常将pH值调至4~5的含曲酸制剂中,高极性紫外线吸收剂的掺入会造成随着时间变化乳化稳定性降低。
因而,本发明的目的是提供一种表皮用制剂,这种制剂克服了传统的含曲酸制剂存在的上述缺陷,即该制剂不会出现紫外线吸收剂的离析,增强了随时间变化曲酸色变和分解的稳定性,特别是解决了热引起的问题,该制剂是通过向含曲酸和/或其衍生物的外用制剂中至少加入一种选自醇和多酚的物质而制成的。
本发明的其它目的、特征及优点通过以下对本发明优选实施方式的详细描述将充分展现出来。
本发明所采用的曲酸(5-羟基-2-羟甲基-γ-吡酮)为第一种成分,它可为5-羟基-2-羟甲基-γ-吡酮的纯产物,包含曲酸作为主要成分且通过培养已知的能产生曲酸的细菌种而得到的发酵液,发酵液的浓缩液,由发酵液中提取曲酸并使提取物结晶获得的产物,等等。
曲酸衍生物可单独使用,或者两种或多种组合使用,曲酸衍生物公开了例如以下的文献中:日本审查专利公开号S60-10005,H1-45472和H3-74229,曲酸和其衍生物的酯化产物公开了例如以下的文献中:日本审查专利公开号S58-22151和S58-22152。上述酯化产物中,糖被键合到曲酸2-位的-CH2OH基团上。
曲酸和/或其衍生物在制剂中的掺入量为0.001~10%(wt),优选0.1~5%(wt),以外用制剂总量计。
用于本发明中作为第二种成分的紫外线吸收剂没有特别限定。优选的实例包括:二苯酮衍生物如:羟基二苯酮,羟二苯酮磺酸,羟基甲氧基二苯酮磺酸钠和二羟基二甲氧基二苯酮;水杨酸衍生物如:水杨酸乙二醇酯,水杨酸单
酯和水杨酸苯酯;尿刊酸和尿刊酸乙酯;肉桂酸衍生物如:对甲氧基肉桂酸2-乙基已酯和甲氧基肉桂酸辛酯;对氨基苯甲酸衍生物如:对氨基苯甲酸甘油酯和对二甲基氨基苯甲酸2-乙基已酯;二苯甲酰甲烷衍生物如4-叔丁基-4′-甲氧基二苯甲酰甲烷;苯并三唑衍生物如2-(2-羟基-5-甲苯基)苯并三唑。这些化合物可以单独使用或两种或多种组合使用。此外,其它具有紫外线吸收能力的动物或植物提取物也可适宜地单独或组合使用。
这些紫外线吸收剂的用量取决于其种类,但一般说来,其用量为0.001~10%(wt),优选0.1~5%(wt),以外用制剂总量计。
本发明中采用醇作为第三种成分,它可以是:低级醇如乙醇、丙醇和异丙醇;高级醇,如辛基十二烷醇、橄榄油醇、油醇、硬脂醇、鲸蜡基硬脂醇(cetostearyl alcohol)、癸基十四烷醇、已基癸醇、西蒙德木醇、肉豆蔻醇和月桂醇;多元醇,如亚烷基(含15-18个碳原子)二醇,亚烷基(含20-30个碳原子)二醇,乙二醇,高聚聚乙二醇,二甘油,二丙二醇,已二醇,聚乙二醇200,聚乙二醇300,聚乙二醇400,聚乙二醇600,聚乙二醇1000,聚乙二醇1500,聚乙二醇4000,聚乙二醇6000,聚乙二醇20000,聚丙二醇400和聚丙二醇1200;糖醇如果糖、木糖醇、D-木糖,山梨醇,D-山梨醇,葡萄糖,麦芽糖醇,麦芽糖,D-mznnitol和淀粉分解糖醇;多元醇烷基醚,如异硬脂酸甘油醚,乙二醇乙醚,乙二醇甲醚,乙二醇单丁醚,鲛肝醇,二乙二醇乙醚,二甘油油基醚,鲨肝醇。
如下的优选实例可单独或两种或多种组合使用:多酚;焦棓酚;间苯三酚;儿茶素,如儿茶素,表儿茶素,棓儿茶素,棓酸儿茶素,棓酸棓儿茶酸,表棓酸儿茶素,表棓酸棓儿茶素和表棓儿茶素;葡糖棓苷;proanthocyanidin;棓酸;棓酸酯,如棓酸丙酯、棓醇异戊基辛酯、棓酸十二烷酯;黄酮,如芸香苷,五羟黄酮,quercetagin,六羟黄酮,棉子皮亭;五-0-棓酰葡萄糖,丹宁酸;各种丹宁,如棓单宁、鞣花单宁和由收敛剂日本柿或茶中提取的浓缩单宁;莽草酸。
第三种成分的用量取决于其种类,但一般说来,其用量为0.001~20%(wt),优选0.1~10%(wt),以制剂总量计。
可以按已知的方法将上述三种成分制成外用制剂。该种制剂不会出现紫外线吸收剂的离析,因而该制剂为一种稳定的乳化制剂,其随着时间变化显示出良好的稳定性,其中曲酸表现出随时间变化色变和分解的稳定性增强了,且表现出持久效能。
无需多言,本发明的制剂形式不限于乳剂如O/W乳剂和W/O乳剂,还可以为一种经适当选择成分而成的透明型制剂。此外,本发明也可适于作为一种基本技术用来制备多层乳剂制剂如W/O/W或O/W/O乳剂或微胶囊制剂。
本发明的表皮用制剂并不特别限制使用方式,它可以以已知的药物、准药物和化妆品的使用方式使用,如糊剂、膏药剂、膏剂、乳霜剂、软膏剂、汽雾剂、乳剂、洗剂、香精剂(essence)、润肤膏、胶凝剂、粉剂、粉底(foundatian)防晒剂(suncare)、浴盐(batbsalts)等。
在本发明的制剂制备过程中,各种已知的常用有效成分也可选择性地加入,但要求其量不会损坏本发明目的。这些已知的有效成分的实例包括:毛细血管扩张剂,如氯化三甲胺丁酸甲酯氯、顶花防已碱、维生素E、烟酸维生素E酯烟酸、烟酸酰胺、烟酸苯甲酯、姜酊和辣椒酊(ginger tincture,chilitincture);冷却剂如樟脑、薄荷醇和薄荷油;抗微生物剂如:4-异丙基环庚二烯酚酮、氯化苯甲烃铵十一碳烯酸;抗炎剂如肾上腺皮质激素、氨基已酸、溶菌酶氯化物、甘草、尿囊素;皮肤白嫩剂(fairness imparting agents)如:抗坏血酸和熊果苷;各种动植物提取物,如,胎盘提取物、肝提取物,lithospermum根提取物,乳酸菌培养液提取物。
除了已知的有效成分,各种添加剂均可使用,如润湿剂、防腐剂、抗氧化剂、螯合剂、PH调节剂、香料、着色剂,以及基底成分如脂肪和油,只要它的加入不会损坏本发明上述药物、准药物和化妆品的应用方式。
通过下述实例和配方对本发明进行更为详细的描述,它们不是对本发明的限制。
实施例1
制剂稳定性试验
实验方法:
按照表1所示配方制备各种乳油(pH约4.5)。将它们置于4盎司的蜡瓶中,在50℃下放置2个月并同时用紫外线照射。2个月后,测量其色差(△E)(使用Nihon Denshoku kogyo制造的Z-1001DP型色差仪)。同时对其外观变化进行观察(紫外线吸收剂的离析和乳剂的稳定性),测量曲酸的残余量比例(用传统方法做HPLC方法,取开始测量时起始值为100进行计算),并评估其应用效果。
实验结果:
如表1所示,本发明的制剂没有出现紫外线吸收剂的离析,同时表明了极佳的乳剂稳定性。制剂中所包含的曲酸的色变或分解未由于加热而观测到,应用感觉良好。
表1-1
*1:微量
*2:足以使总量达100%(重量)的量
*3:分离紫外线吸收剂
*4:乳液状态(未分离)
⊙:良好;△:部分分离;×:分离
*5:评价标准:
⊙:良好;○:几乎没问题;△:有轻微问题;×:不好
*6:粗糙感
*7:粘着感
*8:皮肤舒适
表1-2
*1:微量
*2:足以使总量达100%(重量)的量
*3:分离紫外线吸收剂
*4:乳液状态(未分离)
⊙:良好;△:部分分离;×:分离
*5:评价标准:
⊙:良好;○:几乎没问题;△:有轻微问题;×:不好
*6:粗糙感
*7:粘着感
*8:皮肤舒适
本发明的配制实施例如下:
配制实施例1[霜剂(1)] (重量%)
1.曲酸 1.00
2.羟苯磺酸(Hydroxybenzenesulfonic acid) 0.50
3.甘露醇 2.00
4.聚乙二醇400 3.00
5.聚氧乙烯鲸蜡醚(25EO) 5.00
6.硬脂酸 5.00
7.鳄梨酸 1.00
8.杏仁油 10.00
9.dl-吡咯烷酮羧酸钠溶液 5.00
10.对羟基苯甲酸酯 0.20
11.乙二胺四乙酸二钠 0.01
12.纯化水加至 100.00
配制实施例2[霜剂(2)] (重量%)
1.曲酸 5.00
2.4-叔丁基-4′-甲氧基-二苯甲酰甲烷 0.50
3.西蒙得木醇 1.00
4.山梨醇 3.00
5.表儿茶素棓酸酯 0.50
6.二甲基硅氧烷甲基(聚氧乙烯-聚氧丙烯共聚物) 3.00
7.西蒙得木油 7.00
8.癸基环戊硅氧烷 3.00
9.辛基环丁硅氧烷 3.00
10.二甲基聚硅氧烷 5.00
11.天然维生素E 0.04
12.1%透明质酸钠溶液 2.00
13.角叉菜胶 1.00
14.乙二胺四乙酸二钠 0.01
15.纯化水加至 100.00
配制实施例3[乳剂(1)] (重量%)
1.曲酸 4.00
2.2-乙基已基-对甲氧基肉桂酸酯 2.00
3.聚乙二醇4000 3.00
4.辛基十二烷醇 3.00
5.聚氧乙烯鲸蜡醚(25EO) 0.50
6.聚氧乙烯油醚 1.00
7.硬脂酸 0.50
8.牛油树脂 0.50
9.鳄梨油 4.00
10.对羟基苯甲酸酯 0.20
11.榠栌子提取物 5.00
12.黄原胶 0.14
13.乙二胺四乙酸二钠 0.01
14.纯化水加至 100.00
配制实施例4[乳剂(2)] (重量%)
1.曲酸 0.50
2.水杨酸乙二醇酯 0.10
3.甲氧基肉桂酸辛酯 2.00
4.鲨肝醇 3.50
5.莽草酸 2.00
6.可可油脂肪酸单乙醇酰胺 2.00
7.硬脂酸 0.50
8.肉豆蔻酸 0.50
9.鳄梨酸 4.00
10.天然维生素E 0.04
11.对羟基苯甲酸酯 0.20
12.透明质酸钠 5.00
13.黄原胶 0.14
14.乙二胺四乙酸二钠 0.01
15.纯化水加至 100.00
配制实施例5[洗剂] (重量%)
1.曲酸葡糖苷 7.00
2.4-叔丁基-4′-甲氧基-二苯甲酰甲烷 2.00
3.2-乙基已基-对甲氧基肉桂酸酯 0.05
4.乙二醇乙醚 3.00
5.聚氧乙烯鲸蜡醚(60E、O) 5.00
6.人参提取物 2.00
7.日本chirate提取物 0.50
8.对羟基苯甲酸酯 0.10
9.抗坏血酸 0.10
10.柠檬酸钠 0.30
11.5%弹性蛋白水解液 4.00
12.乙二胺四乙酸二钠 0.01
13.纯化水加至 100.00
配制实施例6[霜剂润肤膏] (重量%)
1.曲酸乙酯 2.00
2.4-叔丁基-4′-甲氧基-二苯甲酰甲烷 0.50
3.癸基四癸醇 2.00
4.聚乙二醇1500 5.00
5.硬脂酸二乙醇酰胺 5.00
6.硬脂酸 5.00
7.肉豆蔻酸 0.50
8.可可油 15.00
9.天然维生素E 0.04
10.对羟基苯甲酸酯 0.20
11.dl-吡咯烷酮羧酸钠溶液 5.00
12.乙二胺四乙酸二钠 0.01
13.纯化水加至 100.00
配制实施例7[软膏剂] (重量%)
1.曲酸 1.00
2.羟苯磺酸 0.10
3.水杨酸苯酯 0.40
4.羟基甲氧基苯并苯甲酰磺酸钠(Sodium hydoxyme thoxy benzophenonesulfonat) 1.00
5.棓酸异戊基辛基醚 2.00
6.可可油脂肪酸单乙醇酰胺 5.00
7.凡士林 10.00
8.硬脂酸 5.00
9.油酸 1.00
10.橄榄油 10.00
11.对羟基苯甲酸酯 0.20
12.角叉菜胶 5.00
13.乙二胺四乙酸二钠 0.01
14.纯化水加至 100.00
配制实施例8[泥敷剂] (重量%)
1.曲酸果糖苷 0.50
2.对氨基苯甲酸甘油酯 4.00
3.芦丁 1.00
4.硬脂酸二乙醇酰胺 3.00
5.聚丙烯酸 27.00
6.甘草提取物(乙醇提取物) 0.10
7.黄岭根提取物(水提取物) 0.05
8.乙二胺四乙酸二钠 0.50
9.聚丙烯酸钠 7.00
10.氯化铝 0.30
11.浓甘油 20.00
12.氧化钛 4.00
13.纯化水加至 100.00
配制实施例9[香精] (重量%)
1.曲酸 1.00
2.尿刊酸 0.50
3.2-乙基已基-对甲氧基肉桂酸酯 1.00
4.异丙醇 0.50
5.苄醇 0.05
6.木糖 1.50
7.可可油脂肪酸单乙醇酰胺 2.00
8.硬脂酸 0.50
9.亚麻酸 0.50
10.鳄梨油 2.00
11.龟油 3.00
12.天然维生素E 0.04
13.对羟基苯甲酸酯 0.20
14.1%羧乙烯聚合物水溶液 5.00
15.黄原胶 0.14
16.乙二胺四乙酸二钠 0.01
17.纯化水加至 100.00
已证实且述配制实施例1~9提供了具有同样令人满意效果(如表1中所示)的制剂。
在不背离本发明精神和基本特征的前提下,本发明可以其它特定形式实现。因此本发明的具体方案在各方面均被认为是用于说明而非限制,本发明的范围通过附加的权利要求而不是前面的描述来指明;并且其中包括了在权利要求相当的方法和范围内发生的全部变化。
Claims (13)
1、一种表皮用制剂,它含有曲酸和/或其衍生物及一种紫外线吸收剂,它还含有至少一种组份,该组份选自醇和多酚。
2、如权利要求1所述的表皮用制剂,其中所述的醇选自低级醇、高级醇、糖醇、多醇和多元醇烷基醚,且所述的多酚选自棓酸的儿茶素酯、黄酮和单宁。
3、如权利要求1所述的表皮制剂,其中所述醇是辛基十二烷醇。
4、如权利要求1所述的表皮用制剂,其中所述醇是聚乙二醇。
5、如权利要求1所述的表皮用制剂,其中所述多酚是表棓儿茶素。
6、如权利要求1所述的表皮用制剂,其中所述多酚是莽草酸。
7、如权利要求1所述的表皮用制剂,其中所述曲酸衍生物是曲酸糖苷。
8、如权利要求7所述的表皮用制剂,其中所述曲酸糖苷是曲酸葡糖苷。
9、如权利要求7所述的表皮用制剂,其中所述曲酸糖苷是曲酸果糖苷。
10、如权利要求1所述的表皮用制剂,其中所述曲酸衍生物是曲酸乙酯。
11、如权利要求1所述的表皮用制剂,其中所述一种组份的掺入量占该制剂总重量的0.001~20%。
12、如权利要求1所述的表皮用制剂,其中所述一种组份的掺入量占该制剂总重量的0.1~10%。
13、如权利要求1所述的表皮用制剂,它的形式选自泥敷剂、膏剂、糊剂、霜剂、软膏剂、气雾剂、乳剂、洗剂、香精(essence)、润肤膏、胶剂、粉剂、粉底、防晒剂和沐浴盐。
Applications Claiming Priority (3)
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JP270972/93 | 1993-10-28 | ||
JP27097293A JP3661707B2 (ja) | 1993-10-28 | 1993-10-28 | 皮膚外用剤 |
JP270972/1993 | 1993-10-28 |
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CN1106660A true CN1106660A (zh) | 1995-08-16 |
CN1077429C CN1077429C (zh) | 2002-01-09 |
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US (1) | US5750563A (zh) |
JP (1) | JP3661707B2 (zh) |
KR (1) | KR100309401B1 (zh) |
CN (1) | CN1077429C (zh) |
MY (1) | MY115307A (zh) |
TW (1) | TW307683B (zh) |
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WO1996029895A1 (de) * | 1995-03-31 | 1996-10-03 | Schuer Joerg Peter | Verfahren zur haltbarkeitsverbesserung und/oder stabilisierung von mikrobiell verderblichen produkten |
KR19980034293A (ko) * | 1996-11-06 | 1998-08-05 | 성재갑 | 갈로일시키믹산을 함유하는 피부 미백용 조성물 |
KR19980034827A (ko) * | 1996-11-08 | 1998-08-05 | 성재갑 | 피부 미백용 조성물 |
US20020176882A1 (en) * | 1997-06-23 | 2002-11-28 | Schur Jorg Peter | Additive the improvement and/or stabilization of the keeping quality of microbially perishable products |
US20050203187A1 (en) * | 1998-06-01 | 2005-09-15 | Verbiscar Anthony J. | Formulations useful for the treatment of varicella zoster virus infections and methods for the use thereof |
EA003741B1 (ru) * | 1998-06-01 | 2003-08-28 | Энтони Дж. Вербискар | Местное трансдермальное лечение |
DE19923713A1 (de) * | 1999-05-22 | 2000-11-23 | Beiersdorf Ag | Kosmetische oder dermatologische Lichtschutzzubereitungen mit einem Gehalt an Flavonderivaten und/oder Flavanonderivaten, insbesondere von Flavonoiden und Benzotriazol sowie die Verwendung von UV-Filtersubstanzen, welche das Strukturmotiv des Benzotriazols aufweisen, zur Stabilisierung von Flavonderivaten und/oder Flavanonderivaten, insbesondere von Flavonoiden |
DE19923712A1 (de) * | 1999-05-22 | 2000-11-23 | Beiersdorf Ag | Wirkstoffkombination aus sulfonierten UV-Filtersubstanzen und Flavonderivaten und/oder Flavanonderivaten, insbesondere Flavonoiden, sowie kosmetische Zubereitungen, solche Wirkstoffkombinationen enthaltend |
DE19931185A1 (de) | 1999-07-07 | 2001-01-18 | Joerg Peter Schuer | Verfahren zur Entkeimung von Luft |
DE19940283A1 (de) * | 1999-08-25 | 2001-03-01 | Joerg Peter Schuer | Pflanzenschutz |
DE19940605A1 (de) | 1999-08-27 | 2001-03-01 | Joerg Peter Schuer | Imprägnierungsverfahren |
JP4671205B2 (ja) * | 1999-10-25 | 2011-04-13 | 三省製薬株式会社 | 皮膚外用剤 |
US8529970B2 (en) | 2000-01-03 | 2013-09-10 | International Flora Technologies, Ltd. | High unsaponifiables and methods of using the same |
DE20100121U1 (de) * | 2001-01-05 | 2002-05-16 | Schür, Jörg Peter, Prof., 41844 Wegberg | Vorrichtung zur Anreicherung von Luft mit Luftbehandlungsmittel |
DE10100595A1 (de) * | 2001-01-09 | 2002-07-18 | Joerg Peter Schuer | Verfahren zur untoxischen Geruchsneutralisierung von Luft |
US20030031588A1 (en) * | 2001-06-13 | 2003-02-13 | Schur Jorg Peter | Device for enriching air with an air treatment agent, especially for the disinfection of air, and/or perfuming of air and/or for odor masking |
US20030059488A1 (en) * | 2001-07-30 | 2003-03-27 | Eugene Daniels | Bioflavanoid-rich potent extract and process for the extraction from white oak bark and pine bark |
US6559182B1 (en) * | 2001-11-07 | 2003-05-06 | Purcell Jojoba International, Llc | Method for treatment of enveloped viruses using jojoba oil esters |
US7314634B2 (en) * | 2002-02-22 | 2008-01-01 | Steven Hernandez | Use of polyphenols to treat skin conditions |
KR100868905B1 (ko) * | 2004-03-26 | 2008-11-14 | (주)아모레퍼시픽 | 진세노사이드 f1과 egcg을 함유한 자외선 조사로유도되는 피부손상 방지용 조성물 |
IT1392474B1 (it) * | 2008-12-10 | 2012-03-09 | Sinerga S P A Ora Sinerga Group S R L | Formulazioni cosmetiche e dermofarmaceutiche a base di acido shikimico. |
FR2939669B1 (fr) * | 2008-12-17 | 2011-03-25 | Oreal | Procede cosmetique pour controler le brunissement de la peau induit par les radiations uv ; compositions. |
JP5610741B2 (ja) * | 2009-10-30 | 2014-10-22 | 三省製薬株式会社 | 化粧のり向上用化粧料 |
KR102001257B1 (ko) * | 2013-10-31 | 2019-07-17 | 주식회사 엘지생활건강 | 에틸헥실갈레이트를 포함하는 항균용 조성물 |
KR20150102727A (ko) * | 2014-02-28 | 2015-09-07 | 교와 가부시키가이샤 | 유중수형 유화 조성물 |
US20220175000A1 (en) | 2019-03-28 | 2022-06-09 | Sumitomo Bakelite Co., Ltd. | Water-soluble additive composition |
AU2019448729A1 (en) * | 2019-10-16 | 2022-03-31 | Mesoestetic Pharma Group, SL | Cosmetic compositions and use thereof |
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JPS61109705A (ja) * | 1984-11-01 | 1986-05-28 | Sansho Seiyaku Kk | 色白化粧料 |
US4956353A (en) * | 1988-06-16 | 1990-09-11 | The United States Of America As Represented By The Secretary Of Agriculture | Kojic acid and esters as insecticide synergists |
JP2903240B2 (ja) * | 1990-03-23 | 1999-06-07 | 株式会社コーセー | 皮膚外用剤 |
JP2822093B2 (ja) * | 1990-05-10 | 1998-11-05 | 株式会社コーセー | W/o/w型乳化化粧料 |
JPH0517317A (ja) * | 1991-07-02 | 1993-01-26 | Nippon Saafuakutanto Kogyo Kk | 化粧料及び外用剤 |
JP2977980B2 (ja) * | 1991-12-04 | 1999-11-15 | 日本鋼管工事株式会社 | ライニング装置及びライニング工法 |
-
1993
- 1993-10-28 JP JP27097293A patent/JP3661707B2/ja not_active Expired - Lifetime
-
1994
- 1994-04-27 TW TW083103814A patent/TW307683B/zh not_active IP Right Cessation
- 1994-04-27 KR KR1019940008977A patent/KR100309401B1/ko not_active IP Right Cessation
- 1994-05-13 MY MYPI94001211A patent/MY115307A/en unknown
- 1994-06-04 CN CN94106506A patent/CN1077429C/zh not_active Expired - Lifetime
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1995
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Publication number | Publication date |
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US5750563A (en) | 1998-05-12 |
JP3661707B2 (ja) | 2005-06-22 |
JPH07126135A (ja) | 1995-05-16 |
KR100309401B1 (ko) | 2002-02-19 |
MY115307A (en) | 2003-05-31 |
CN1077429C (zh) | 2002-01-09 |
KR950010877A (ko) | 1995-05-15 |
TW307683B (zh) | 1997-06-11 |
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