CN1231167A - 含新型颜料的化妆品组合物 - Google Patents
含新型颜料的化妆品组合物 Download PDFInfo
- Publication number
- CN1231167A CN1231167A CN99104433A CN99104433A CN1231167A CN 1231167 A CN1231167 A CN 1231167A CN 99104433 A CN99104433 A CN 99104433A CN 99104433 A CN99104433 A CN 99104433A CN 1231167 A CN1231167 A CN 1231167A
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- Prior art keywords
- compositions
- composition
- skin
- lip
- pigment
- Prior art date
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Abstract
本发明涉及化妆品组合物,尤其涉及彩妆组合物,它含有一种颜色强烈且饱和、不产生自由基的新型红颜料。该新型颜料是符合下式的二酮基吡咯并吡咯(DPP)化合物:式中,R1和R2独立地代表:氢原子;C1-C18烷基;C3-C12烯基;C2-C5烷氧羰基;任选地被一个卤原子取代的苯基;R3和R4独立地代表:氢原子;C1-C18烷基;C1-C4烷氧基;卤原子;苯基;或-SO3M基团,其中M代表卤原子、金属原子或铵基团;其中烷基、烯基或烷氧基可以是直链或支链的。由于使用了该颜料,组合物能保护皮肤、嘴唇和角质纤维免受自由基的侵害,而无需在组合物中使用抗氧剂。
Description
本发明涉及含一种颜色强烈且饱和、不产生自由基的新的红颜料的化妆品组合物,更具体而言,本发明涉及用于人体面部或身体的皮肤、角质物或表皮生长物,例如指甲、眉毛、睫毛、头发和嘴唇的化妆组合物。
化妆品组合物,例如粉末或粉饼、粉底霜、面霜或眼影、口红、防黑眼圈剂(les anticernes)、胭脂(les blushes)、睫毛油、眼线、唇笔、眼部化妆笔、指甲油和体用化妆品,是由合适的载体和不同性质的生色剂组成的,后者用于在组合物施用到皮肤、嘴唇和/或表皮生长物上之前或之后,使组合物产生一定的颜色。
这些生色剂可以是色淀类(les laques)、无机或有机颜料和/或珠光颜料,或者是着色剂(des colorants)。在红色颜料中,化妆师可以采用无机颜料,例如红色氧化铁颜料或棕黄氧化铁颜料的混合物,或者采用有机颜料。无机颜料,尤其是无机氧化物颜料,具有相当稳定的优点,但是也具有色彩枯燥黯淡的缺点。有机颜料可以为组合物带来生动的颜色,但是大多数对光、温度和pH不稳定。某些此类色淀还具有如下缺点,即在施用之后,由于释放出着色剂而弄脏皮肤,使之难看。至于珠光颜料,它可以产生多种颜色,但是这些颜色都不强烈,这些颜色具有彩虹色的效果,但是绝大多数情况下相当微弱。
另外,某些生色剂还具有如下缺点,即在化妆品制剂中产生自由基,从而改变了组合物的颜色和稳定性,施用到皮肤上之后,会导致表皮老化(出现皱纹、细线,使皮肤发黄)。在具有这些缺点的生色剂中,作为例子尤其可以提及的是:BASF公司以“Sicomet Brun ZP 3569”为商品名销售的棕黄色氧化铁混合物、有机颜料例如WACKER公司以“DC Red36W 008”为商品名销售的火焰红(Rouge Flaming)(D&C Red No.36,颜色索引号是12085),以及铝基色淀(laque d’aluminium),载于氧化铝上的根皮红B(D&C Red No.27铝色淀)。
为了克服这些缺点,现使用例如乙氧基醌(ethoxyquine)的抗氧剂。但是考虑到化妆品组合物中成分的多样性,难以找到一种完全有效的抗氧剂。而且这些抗氧剂本身通常会产生降解(抗氧剂的氧化)产物,这是令人讨厌的。
本发明的目的正好在于在化妆品组合物中应用一种颜色强烈且饱和、稳定、与常用的尤其为了产生红颜色的颜料相比,产生少得多的自由基的新型红色颜料。
出乎意料的是,申请人已发现,由于二酮基吡咯并吡咯类(简称为DPP)产生很少的自由基,它们可以限制自由基的生成,从而避免在组合物中使用抗氧剂。此外,这些颜料可以产生强烈的颜色,尤其是生动而强烈的朱红色,它们不会在皮肤上迁移,对光、温度和pH稳定。
更精确地讲,本发明涉及局部施用的生色组合物,更具体而言,是一种含有下式(A)颜料的化妆和彩妆组合物:式中,R1和R2独立地代表:氢原子;C1-C18烷基;C3-C12烯基;C2-C5烷氧羰基;任选地被一个卤原子取代的苯基;R3和R4独立地代表:氢原子;C1-C18烷基;C1-C4烷氧基;卤原子;苯基;或-SO3M基团,其中M代表卤原子、金属原子或铵基团;其中烷基、烯基或烷氧基可以是直链或支链的。R3可以在2、3、4、5或6位上,优选在4位上。金属可以是钠、钾或锂。
烷基或烷氧基可以是直链或支链的,尤其选自:甲基、乙基、正丙基、异丙基、正丁基、二级丁基、叔丁基、异丁基、正戊基、二级戊基、叔戊基或异戊基等。烯基可以是直链或支链的,选自:烯丙基、甲基烯丙基、2-丁烯基、2-己烯基、3-己烯基、2-辛烯基等。卤原子可以是氯或氟。优选地,R1和R2独立地代表氢原子、甲基或4-氯苯基。有利地,R3和R4独立地代表氢原子、4-氯或者4-叔丁基。本发明的颜料可以是透明或不透明的,且任选地与其它颜料联用,以提高所述DPP颜料和本发明组合物对光和文件WO-A-98/56859中所述因素的稳定性,或者为了改善其色彩强度,和/或改善具有各向异性发色(goniochromatic)性质的液晶颜料或多层颜料的各向异性生发色性。
式(A)的二酮基二芳基吡咯并吡咯的制备方法尤其见述于汽巴-嘉基公司的EP-A-542669、EP-A-787730、EP-A-787731和WO-A-96/08537。
优选使用“Rouge Irgazine DPP-red BO”,颜色索引(color index,缩写为CI)号为Pigment Red 254-No.CI 56110。它涉及吡咯(3,4-c)吡咯-1,4-二酮,其中的两个苯环在2,5位上被氢化,在4位上被卤代。该化合物具有下式(B):
本发明组合物中可以应用的其他DPP颜料可以举例如下:
-Cromophtal DPP Red BP P-CI Pigment Red 254-No.CI 56110;
-Cromophtal DPP Red BP-CI Pigment Red 254-No.CI 56110;
-Irgazine DPP Red 5G-CI Pigment Red 255;
-Irgazine DPP Rubbine TR-CI Pigment Red 264;
-Irgazine DPP Red 5049 B-CI Pigment Red 270;
Irgazine Orange RA-CI Pigment Orange 73。
为了证明DPP不产生自由基的特性,申请人按照下面的文章中所述的方法进行了乙烯试验:J.B.Galey,F.Millecamps和Q.L.Nguyen,《由甲硫氨酸产生乙烯作为一种评价化妆品清除氧自由基和使金属减活性能的方法》,国际化妆品科学杂志,13,65-78,1991。
目的在于比较本发明有机颜料和常用颜料在光氧化反应中的性质,使用铁作为自由基产生剂。
在乙烯试验方法中,用于激发产生自由基的FeCl3被任何一种待试验颜料所代替。试验结果报告于下表:
乙烯产物(峰面积)(surface de pic) | |||
着色剂 | |||
浓度 | 0.0001% | 0.002% | 0.02% |
棕黄氧化铁 | 6641 | 14213 | 9708.5 |
火焰红(Rouge Flaming) | 4447 | 3316.5 | 2579.5 |
DPP | 1854 | 2215 | 1903 |
对照物0.005%FeCl3的平均值是9000(绝对单位,相对测量)。
乙烯量越大,产生的自由基越多。
原材料棕黄氧化铁(CI 77491+CI 77492)和火焰红(CI 12085)不是惰性的。在低剂量下,它们是活化的直至一定浓度,对颜料的保护作用才开始显现,而对于DPP,与另两个试剂相比,所产生的乙烯量相当低,并且不随浓度而改变。因此这种颜料可以应用在彩妆组合物和有色防晒组合物中,特别是后者用于保护皮肤和粘膜,例如嘴唇,而不会产生自由基,由此限制了皮肤和/或粘膜的伤害。
本发明的颜料还可以加入到尤其是彩妆组合物的化妆品组合物中,其用量可以由本领域技术人员按常识来确定,相对于组合物的总重量,其量特别可以占0.01%-50%(重量),优选为0.5%-25%(重量)。颜料还可以具体通过接枝或镶嵌方法固定在聚合物上。
本发明组合物可以呈用于嘴唇、眼部、皮肤和/或表皮生长物的产品形式。因此它含有一种化妆品可以接受的基质,即可以与所有的角质物,例如人体和面部皮肤、指甲、头发、睫毛和眉毛相容的介质。该介质可以含有或具体呈如下形式:溶剂介质、水中或水醇介质中的悬浮液、分散液或溶液,并任选地被增稠或凝胶化;水包油型、油包水型或多重乳液;凝胶或泡沫;乳化凝胶;泡囊分散体,尤其是离子或非离子类脂的;两相或多相洗剂;喷雾剂;粉尘、粉饼或流动粉末;无水糊剂。一方面考虑到所用的组分的性质,尤其是它们在载体中的溶解性,另一方面考虑到组合物的预定用途,本领域技术人员可以按照常识选择适当的药物剂型式及其制备方法。
当本发明组合物呈乳液形式时,还可以任选地含有一种表面活性剂,相对于组合物总重量,其量优选为0.01%-30%(重量)。
按照预定的用途,组合物还可以含有一种聚合物成膜剂(例如硝化纤维素、烃树脂和/或聚硅氧烷树脂)。当需要制备指甲油、染眉油、眼线或色淀类发用组合物时,情况尤其如此。聚合物可以溶解或分散在化妆品可接受的介质中,并可任选地联用聚结剂和/或增塑剂。
本发明组合物还可以含有脂肪相,具体由室温(一般为25℃)下为液体和/或固体的脂肪物质组成,例如蜡类、膏状脂肪物质、树胶类或其混合物。
室温下呈液体的脂肪物通常称作油,在本发明中可以应用的举例如:来自于动物的烃类油,如全氢角鲨烯;烃类植物油,例如液体的含4-10个碳原子的脂肪酸的三酸甘油酯,例如庚酸或辛酸的三酸甘油酯,或者向日葵油、玉米油、大豆油、葡萄籽油、芝麻油、杏油、澳洲坚果油、蓖麻油、鳄梨油、辛酸/癸酸的三酸甘油酯、西蒙得木油、乳油木油;矿物或合成的直链或支链烃油,例如液体石蜡油及其衍生物、凡士林、聚癸烯、例如parleam的聚异丁烯;尤其是脂肪酸的合成脂类或醚类,例如Purcellin油,肉豆蔻酸异丙酯,棕榈酸2-乙基己基酯,硬脂酸2-辛基十二烯基酯,芥酸2-辛基十二烯基酯或异硬脂酸异硬脂基酯;羟基化酯类,例如乳酸异硬脂基酯,羟基硬脂酸辛酯,羟基硬脂酸辛基十二烷基酯,苹果酸二异硬脂基酯,柠檬酸三异鲸蜡基酯,脂肪醇的庚酸、辛酸和癸酸酯;多元醇的酯,例如丙二醇的二辛酸酯,新戊二醇的二庚酸酯,二乙二醇的二异壬酸酯,季戊四醇酯;含12-26个碳原子的脂肪醇,例如辛基十二烷醇,2-丁基辛醇,2-己基癸醇,2-十一烷基十五烷醇或油醇;部分烃化和/或聚硅氧烷化的氟化油;聚硅氧烷油,例如挥发或不挥发、线型或环状、室温下为液体或膏状的聚甲基硅氧烷(PDMS),例如环聚甲基硅氧烷类,二甲基硅氧烷类,并可任选地带有苯基,例如苯基三甲基硅氧烷类,苯基三甲基硅氧基二苯基硅氧烷类,二苯基甲基二甲基-三硅氧烷类,二苯基二甲基硅氧烷类,苯基二甲基硅氧烷类,聚甲基苯基硅氧烷类,及其混合物。
相对于脂肪相总量而言,油的重量可以为0-100%。
本发明的组合物还可以含有相关领域内常用的任何成分,尤其是化妆品领域和皮肤病领域常用的。这些成分特别可以选自:防腐剂,水相或脂肪相增稠剂(多糖生物聚合物或合成聚合物),香料,亲水性或亲脂性活性剂及其混合物。这些成分的用量为其在相关领域内的常用量,例如相对于组合物总重量而言,为0.01%-20%。这些成分及其用量必须与本发明所产生的组合物相容,稳定、稠厚且有光泽。该组合物还可以含有水,其量相对于组合物的总重量为0-98%。
本发明的组合物还可以含有另一种特定的附加相,其量相对于组合物总重量为0-35%,优选为0.05%-20%,该相中可以含有颜料和/或珠光剂和/或化妆品组合物中所采用的填料。
颜料应当被理解为包括无机或有机的白色或有色颗粒颜料,不溶于液体脂肪相中,用于给组合物上色或使之不透明。填料包括无机或合成、层状或非层状的无色或白色颗粒。珠光剂包括彩虹色颗粒,尤其是某些软体动物在其壳中的产物,或者是合成的产物。这些填料和珠光剂尤其对组合物质地起到改良的作用。
除DPP外的颜料在组合物中的存在量,相对于最终组合物的重量,为0-25%,优选为2%15%。本发明可采用的无机颜料中,可以提及的是钛氧化物、锆氧化物、铈氧化物、锌氧化物、铁氧化物和铬氧化物,以及铁蓝。本发明可采用的有机颜料中,可以提及碳黑,钡、锶、钙和铝基色淀(laque)。
珠光剂在组合物中的含量为占组合物总重量的0-20%,优选为约1%-15%。本发明可用的珠光剂中,可以提及的是涂覆了钛氧化物、铁氧化物或氯氧化铋的云母,例如彩色氧化钛云母。
填料在组合物中的含量可以占组合物总重量的0-35%,优选为0.5%-15%。其中尤其可以提及的是滑石,硬脂酸锌,云母,高岭土,尼龙粉末(尤其是Orgasol)和聚乙烯粉末,聚四氟乙烯,淀粉,氮化硼,聚合物微球,例如聚乙二烯-丙烯腈共聚物(Nobel Industry),丙酸廿烷基酯聚合物(Dow Corning)和聚硅氧烷树脂微球(例如Toshiba的Tospearl)。
本发明组合物有利地含有一种固体或膏状脂肪相,含有一种或多种树胶和/或一种或多种蜡。蜡可以是烃蜡,氟化蜡和/或聚硅氧烷蜡,来自于植物,矿物,动物和/或合成的。特别地,蜡的熔点高于25℃,高于45℃更好。
本发明组合物中可用的蜡中,可以提及蜂蜡,Carnauba或Cardellila蜡,烃蜡,微晶蜡,纯地蜡或l’ozokerite,合成蜡,例如聚乙烯蜡或Fischer Tropsch蜡,聚硅氧烷蜡,例如含16-45个碳原子的烷基或烷氧基二甲基硅氧烷(dimeticone)。
树胶一般是高分子量PDMS,膏状物一般是烃类化合物,例如羊毛脂或其衍生物,或者是PDMS。
固体物的性质和用量与所需要的机械性能和质地有关。比如,相对于组合物总重量来说,组合物中可以含0-50%的蜡,5%-30%更好。
本发明的组合物还可以含有一种或多种化妆品可接受(耐受性、毒性和触感上可接受)的有机溶剂。这些有机溶剂可以占组合物总重量的0-98%,并且可以选自:亲水性有机溶剂、亲脂性有机溶剂、两性溶剂或其混合物。
亲水性有机溶剂中,可以举例如含1-8个碳原子的直链或支链的低级一元醇,多元醇,单-烷基或双-烷基的isosorbide(其中的烷基含有1-5个碳原子),二元醇的醚,脂肪酯。
该组合物外观可以呈粉剂、霜剂、膏剂、液体洗剂、25℃下动态粘度为约1-40Pa.s的软膏,油膏,浇铸或成型固体剂,尤其呈棒状或盛于碟内的。
按照所采用的组分的性质,本发明组合物可以有利地用作皮肤和/或嘴唇和/或表皮生长物的彩妆组合物。具体而言,本发明组合物可以是口红棒,或者是口红增亮物,本身可以使用或用在口红膜上,尤其用于改善其亮度和颜色(英语称作表层涂料)。它还可以含有一种固体粉底霜,抗黑眼圈剂(anti-cerne),眼线,染眉油,眼影,粉,胭脂(blush)。该组合物还可以含有其他的化妆或皮肤活性物质,以便特别为组合物带来护理或治疗效果。因此该组合物还可以含有维生素和其他的亲脂性活性剂(羊毛脂、紫外光防晒剂)或亲水性活性剂(例如甘油的润肤剂)。
本发明的目的还在于上述组合物的化妆应用,用于皮肤和/或嘴唇和/或角质纤维的护理、彩妆和/或保护;以及该组合物在制备用于保护皮肤和/或嘴唇的油膏中的应用。本发明的目的还在于皮肤和/或嘴唇和/或角质纤维的化妆处理方法,该方法在于在皮肤和/或嘴唇和/或角质纤维上施用上述定义的组合物。
更具体地讲,本发明的目的在于一种唇用产品或一种胭脂(blush)。
本发明的组合物可以按照如下方法制备:在蜡的熔点或更高的温度下加热各种组分,然后在模具(碟(coupelle)或套管(doigt de gant))内浇铸熔融混合物。如专利申请EP-A-667 146所述,该组合物还可以通过挤出来制备。
本发明还涉及在有色化妆品组合物中应用例如上述的生色剂,用以保护皮肤和/或嘴唇和/或角质纤维免受自由基的侵害,防止皮肤老化,尤其是防止光致老化。这些老化表现为皱纹、细线、皮肤松弛和/或皮肤发黄。
本发明的目的还在于皮肤和/或嘴唇和/或角质纤维的化妆保护方法,防止其受到自由基的侵害,防止皮肤老化现象,尤其是光致老化现象,该方法在于在皮肤和/或嘴唇和/或角质纤维上施用如前述定义的组合物。
下述组合物实施例作说明之用,不构成对本发明的限制。
实施例1:口红
聚乙烯蜡 14克
芝麻油 78克
DPP颜料(式B) 5克
二氧化钛 3克
操作方式:
-在油浴中匀化油和颜料混合物45分钟;
-使混合物连续3次通过一台三辊研磨机;
-在油浴中匀化油和颜料混合物30分钟;
-42℃下浇铸到模具中,30分钟后凝固。
得到一种口红,其颜色鲜艳而强烈,覆盖率高,有光泽,对光稳定,卸妆后不留下任何痕迹。
实施例2:口红
滑石 38克
云母 20克
氯氧化铋 8克
硬脂酸锌 3克
尼龙粉末 20克
DPP颜料(式B) 5克
脂肪粘接剂(*) 适量至 100克
(*)含有如下成分的含碳油混合物:
-3.6克辛酸/癸酸的甘油三酸酯;
-2.0克氢化异链烷烃(非挥发性);
-1.0克西蒙得木油。
操作方式:
-预混合所有的颜料和填料;
-在Lodige(粉末匀化混合器)中混合5分钟;
-加入有机粘接剂;
-在Lodige中混合5分钟;
-通过空气喷射研磨机(CHRISPRO);
-160微米过筛。
实施例3:唇用色淀(lip laquer)
丙烯酸/苯乙烯聚合物水分散液 20%(活性物质)
(Zeneca公司的Ncoaryla-1052)
乙酰基三丁基柠檬酸酯 2.5%
DPP颜料 1.5%
火焰红(CI 17085) 1.5%
甘油 1.25%
水 适量至 100%
Claims (15)
1.局部应用的有色组合物,其特征在于含有式(A)的颜料:式中,R1和R2独立地代表:氢原子;C1-C18烷基;C3-C12烯基;C2-C5烷氧羰基;任选地被一个卤原子取代的苯基;R3和R4独立地代表:氢原子;C1-C18烷基;C1-C4烷氧基;卤原子;苯基;或-SO3M基因,其中M代表卤原子、金属原子或铵基团;其中烷基、烯基或烷氧基可以是直链或支链的。
2.权利要求1的组合物,其特征在于R1和R2独立地代表:氢原子;甲基或4-氯苯基。
3.权利要求1或2的组合物,其特征在于R3和R4独立地代表:氢原子;4-氯或4-叔丁基。
4.上述权利要求中一项的组合物,其特征在于该生色剂是吡咯并(3,4-c)吡咯-1,4-二酮,其中的两个苯并环在2,5位被二氢化,且在4位被氯代。
5.上述权利要求中一项的组合物,其特征在于该生色剂的量相对于组合物的重量为0.01%-50%。
6.上述权利要求中一项的组合物,其特征在于该生色剂的量相对于组合物的重量为1%-25%。
7.上述权利要求中一项的组合物,其呈人体皮肤、嘴唇和/或角质纤维的化妆产品的形式。
8.上述权利要求中一项的组合物,其呈指甲油、染眉油、眼线、或色淀类发用组合物(composition capillaire de type laque)、口红、嘴唇增亮物、粉底霜、防黑眼圈剂、腮红或眼影、粉、胭脂、体用化妆品的形式。
9.上述权利要求中一项的组合物,还含有至少一种脂肪相,该脂肪相选自:油、蜡、树胶、膏状脂肪物质及其混合物。
10.上述权利要求中一项的组合物,其特征在于还含有附加的颗粒相,其量相对于组合物总重量可以为0-35%。
11.上述权利要求中一项的组合物,其呈无水形式。
12.上述权利要求中一项的组合物的化妆应用,用于皮肤和/或嘴唇和/或角质纤维的护理、化妆和/或保护。
13.权利要求1-11中一项的组合物的应用,用于制备治疗和/或保护皮肤和/或嘴唇的油膏。
14.权利要求1-4定义的式(A)生色剂在有色化妆品组合物中或此类组合物生产中的应用,用于保护皮肤和/或嘴唇和/或角质纤维免受自由基的侵害,和/或防止皮肤老化现象。
15.防止自由基侵害和光致皮肤老化现象的皮肤和/或嘴唇和/或角质纤维的化妆保护方法,该方法在于在皮肤和/或嘴唇和/或角质纤维上施用权利要求1-11中一项的组合物。
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FR9803839A FR2776512B1 (fr) | 1998-03-27 | 1998-03-27 | Composition cosmetique contenant un nouveau pigment |
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ES2330342T3 (es) | 2003-12-16 | 2009-12-09 | Colgate-Palmolive Company | Metodos y composiciones para el cuidado bucal y personal. |
EP1781247B1 (en) * | 2004-08-23 | 2010-11-03 | Basf Se | Cosmetic compositions containing fluorescent colorants for natural skin appearance |
US7824663B2 (en) * | 2005-03-10 | 2010-11-02 | Kokyu Alcohol Kogyo Co., Ltd. | Lip gloss composition |
FR2902331B1 (fr) * | 2006-06-20 | 2009-02-20 | Oreal | Mascara comprenant au moins 21% de cire et une charge |
ATE515275T1 (de) * | 2007-05-15 | 2011-07-15 | Procter & Gamble | Verwendung einer lotionszusammensetzung auf einem saugfähigen artikel zur reduktion von fäkal- oder mensesanhaftung an der haut |
EP1992367B1 (en) | 2007-05-15 | 2012-06-27 | The Procter & Gamble Company | Absorbent article comprising a lotion composition for reducing adherence of feces or menses to the skin |
US20080287896A1 (en) * | 2007-05-15 | 2008-11-20 | The Procter & Gamble Company | Absorbent Article With Hydrophilic Lotion And High Barrier Cuffs |
JP2019516672A (ja) | 2016-04-15 | 2019-06-20 | エッカルト ゲゼルシャフト ミット ベシュレンクテル ハフツングEckart GmbH | 表面変性エフェクト顔料およびネイルエナメル組成物 |
EP3624755B1 (de) | 2017-10-18 | 2021-09-01 | ECKART GmbH | Nagellackkomposition enthaltend geprägte effektpigmente sowie oberflächenmodifizierte geprägte effektpigmente |
EP4255988A1 (en) * | 2020-12-03 | 2023-10-11 | Sun Chemical B.V. | A seed surface composition comprising a dpp pigment and a seed treated with said composition |
WO2022147504A1 (en) * | 2021-01-04 | 2022-07-07 | Evkm Technologies, Llc | Thermoreactive compositions, systems, and methods |
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DE69219074T2 (de) * | 1991-11-04 | 1997-10-30 | Chimie Ind Sa Soc Nouv | Verfahren zur Herstellung von Pigmenten, insbesondere fluoreszierenden Pigmenten |
GB9418499D0 (en) * | 1994-09-14 | 1994-11-02 | Ciba Geigy Ag | Process for producing n-methylated organic pigments |
US5618343A (en) * | 1994-12-27 | 1997-04-08 | Ciba-Geigy Corporation | Pigment compositions for coatings |
EP0787731B1 (de) * | 1996-01-30 | 2002-08-07 | Ciba SC Holding AG | Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere |
EP0787730B1 (de) * | 1996-01-30 | 2001-08-01 | Ciba SC Holding AG | Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere |
EP0811625B1 (en) * | 1996-06-05 | 2002-04-17 | Ciba SC Holding AG | Process for preparing diketopyrrolopyrrole derivatives |
DE69709687T2 (de) * | 1997-06-09 | 2002-08-14 | Ciba Sc Holding Ag | Farbstoffmischungen enthaltend ein salzbildendes azopigment und ein 1,4-diketo-3,6-diarylpyrrolo(3,4-c)pyrrol |
-
1998
- 1998-03-27 FR FR9803839A patent/FR2776512B1/fr not_active Expired - Fee Related
-
1999
- 1999-02-11 BR BR9900408-9A patent/BR9900408A/pt not_active IP Right Cessation
- 1999-03-01 CA CA002262134A patent/CA2262134A1/fr not_active Abandoned
- 1999-03-09 KR KR1019990007769A patent/KR100318658B1/ko not_active IP Right Cessation
- 1999-03-25 EP EP99400733A patent/EP0953343B1/fr not_active Expired - Lifetime
- 1999-03-25 DE DE69915922T patent/DE69915922T2/de not_active Expired - Fee Related
- 1999-03-25 ES ES99400733T patent/ES2218963T3/es not_active Expired - Lifetime
- 1999-03-26 JP JP08494699A patent/JP3758885B2/ja not_active Expired - Fee Related
- 1999-03-26 US US09/276,812 patent/US6042842A/en not_active Expired - Fee Related
- 1999-03-26 CN CN99104433A patent/CN1231167A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102167701A (zh) * | 2011-02-25 | 2011-08-31 | 华东理工大学 | 含氟吡咯并吡咯二酮系(dpp)色素及制备方法 |
CN102167701B (zh) * | 2011-02-25 | 2013-04-17 | 华东理工大学 | 含氟吡咯并吡咯二酮系(dpp)色素及制备方法 |
CN107157876A (zh) * | 2017-05-16 | 2017-09-15 | 广州市柏亚化妆品有限公司 | 一种用于提高头发色泽和新生头发的洗发水 |
Also Published As
Publication number | Publication date |
---|---|
BR9900408A (pt) | 2000-05-02 |
KR100318658B1 (ko) | 2002-01-18 |
JP3758885B2 (ja) | 2006-03-22 |
DE69915922T2 (de) | 2005-03-10 |
KR19990077718A (ko) | 1999-10-25 |
FR2776512A1 (fr) | 1999-10-01 |
ES2218963T3 (es) | 2004-11-16 |
EP0953343A1 (fr) | 1999-11-03 |
US6042842A (en) | 2000-03-28 |
JPH11322576A (ja) | 1999-11-24 |
CA2262134A1 (fr) | 1999-09-27 |
EP0953343B1 (fr) | 2004-03-31 |
FR2776512B1 (fr) | 2001-04-13 |
DE69915922D1 (de) | 2004-05-06 |
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