CN103492497A - 基于肽的染发剂 - Google Patents
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Abstract
包含肽染料的染料组合物,所述肽染料包含共价键合至带负电荷的活性染料的肽;其中通过使含有伯胺、仲胺、OH、SH基团或混合物的肽与负电荷的活性染料反应,能够获得所述肽染料。
Description
本发明涉及包含染料的护发组合物和使用所述组合物染发的方法。
背景
WO2006/028503(Dupont)公开了共价键合至特定染料的头发结合肽。通过必须存在于染料上的羧酸、醇、胺或醛基团来进行连接。
FR2456764(L’Oréal)公开了用于头发着色的连接至染料的季胺聚合物。所用染料不携带带负电荷的取代基。
US4228259(L’Oréal)公开了用于角质材料的染料,其包含水溶性阳离子聚合物。
WO2008/009579(Ciba)和WO2009/090121至WO2009/090125(BASF)公开了用于头发着色的共价连接至聚合物的阳离子染料。
共同待决的Unilever申请No.PCT/CN2010/071156公开了头发染料组合物,该头发染料组合物包含共价键合至还负电荷的活性染料的带正电荷聚合物。
尽管有现有技术,但对于更简单的将染料键合至头发结合肽的方法仍然存在需求。
发明描述
本发明提供了包含肽染料的染料组合物,所述肽染料包含共价键合至带负电荷的活性染料的肽;其中通过使含有伯胺、仲胺、OH、SH基团或混合的肽与带负电荷的活性染料反应,能够获得所述肽染料。
在第二个方面中,本发明提供了通过将上述组合物施用至头发的着色头发方法。
发明详述
在本申请的范畴中,术语“MB50”指的是给出在基于ELISA的结合试验中获得的最大信号的50%信号的结合肽浓度。MB50提供了复合物组分的结合相互作用或亲和性强度的指示。MB50值越低,肽与其相应底物的相互作用越强。
术语“结合亲和性”指的是结合肽与其各自的底物的相互作用的强度。本文中根据在基于ELISA的结合试验中测定的MB50值来定义结合亲和性。
组合物可以用于任何材料的染色,优选用于角质材料的染色,更优选其是染发组合物。
染料肽
本发明的组合物包含染料肽,所述染料肽包含共价键合至带负电荷活性染料的肽。
在本发明的范畴中,染料肽和肽染料可以互换使用。
水解活性染料是其中活性基团已经与氢氧根阴离子HO-、而不是与所述聚合物反应的染料。具有两个活性基团的活性染料,在其中一个活性基团已与所述肽反应形成共价键,而一个活性基团已与HO-反应的情况下,并不归类为本发明范畴中的水解活性染料。
同样地,具有三个活性基团的活性染料,在其中一个或两个活性基团已与所述肽反应形成共价键,而一个或两个活性基团已与HO-反应的情况下,并不归类为本发明范畴中的水解活性染料。
水解染料与所述肽不共价键合。
本发明的组合物优选包含低于100ppm水解活性染料/10000ppm染料肽,更优选低于50ppm,最优选低于5ppm。最优选地,组合物中不存在水解活性染料。这样的染料可以通过透析或仔细地控制反应条件而除去。发现不存在水解染料降低了对织物的沾染(staining)。
具有两个活性基团的活性染料,在其中一个已与所述肽反应形成共价键,而一个已与HO-反应的情况下,并不归类为本发明范畴中的水解染料。
优选地,组合物包含总组合物的0.01至15重量%的染料肽,更优选0.2至10重量%,最优选0.5至3重量%的染料肽。
活性染料
活性染料描述于Industrial Dyes(K.Hunger编辑,Wiley VCH2003)。许多活性染料列于colour index(颜色索引)(Society of Dyersand Colourists and American Association of Textile Chemists and Colorists(漂染师与印染师学会以及美国纺织化学师与印染师协会))中。
活性基团优选选自杂环活性基团和磺基氧乙基磺酰基活性基团(-SO2CH2CH2OSO3Na)。
磺基氧乙基磺酰基活性基团在碱中转化成乙烯砜。
杂环活性基团优选是与卤素或铵基或季铵基键合的含氮芳环,其与肽的NH2或NH基团反应,形成共价键。优选卤素,最优选Cl或F。
优选地,活性染料含有不止一个活性基团,优选两个或三个。
优选地,活性染料包含选自如下的活性基团:二氯三嗪基、二氟氯嘧啶、单氟三嗪基、二氯喹喔啉、乙烯砜、二氟三嗪、单氯三嗪基、溴代丙烯酰胺和三氯嘧啶。
除了基于铜酞菁的染料以外,所述染料不包含金属络合物染料,优选所述染料不包含基于偶氮金属络合物染料。
活性基团可以通过烷基间隔基与染料的发色团连接,例如:染料-NH-CH2CH2-活性基团。
尤其优选的杂环活性基团是:
其中R1选自H或烷基,优选H。
X选自F或Cl。
当X=Cl时,Z1选自-Cl、-NR2R3、-OR2、-SO3Na。
当X=F时,Z1选自-NR2R3。
R2和R3独立地选自H、烷基和芳基。芳基优选是苯基并且优选被-SO3Na或-SO2CH2CH2OSO3Na取代。烷基优选是甲基或乙基。
苯基可以进一步被合适的不带电荷的有机基团取代,所述有机基团优选分子量低于200。优选的基团包括-CH3、-C2H5和-OCH3。
烷基可以进一步被合适的不带电荷的有机基团取代,所述有机基团优选分子量低于200。优选的基团包括-CH3、-C2H5、-OH、-OCH3、-OC2H4OH。
最优选的杂环活性基团选自:
其中n=1或2,优选1。
优选地,活性染料含有不止一个的活性基团,优选两个或三个。
优选地,活性染料包含选自偶氮、蒽醌、酞菁、甲臜(formazan)和三苯二噁嗪的发色团。在染料是偶氮染料的情况下,优选偶氮染料不是偶氮-金属络合物染料。
优选地,肽和活性染料的反应是在碱性pH、优选pH=10至11.5、温度40-100℃的水中,在向溶液中添加所述染料之后进行0.5至3小时,形成染料肽。然后,将溶液在1至2小时内冷却至室温并且中和至pH=7。反应溶液中肽的总水平优选为2至50重量%,更优选5至20重量%。这些条件最小化了水解染料的产生。
活性染料的实例包括活性黑5、活性蓝19、活性红2、活性蓝171、活性蓝269、活性蓝11、活性黄17、活性、活性橙4、活性橙16、活性绿19、活性棕2、活性棕50。
活性蓝染料优选选自蒽醌、单偶氮、双-偶氮、三苯二噁嗪和酞菁,更优选蒽醌、双偶氮和三苯二噁嗪,最优选双-偶氮和三苯二噁嗪。
优选的蓝色双偶氮染料具有以下形式:
其中A和B环之一或二者被活性基团取代。A和B环可以进一步被磺酸盐基(SO3Na)取代。A和B环可以进一步被合适的不带电荷的有机基团取代,优选所述有机基团的分子量低于200。优选的不带电荷的有机基团为-CH3、-C2H5和-OCH3。
优选的蓝色蒽醌染料具有以下形式:
其中C环被活性基团取代。染料可以进一步被磺酸盐基(SO3Na)和合适的不带电荷的有机基团取代,优选所述有机基团的分子量低于200。优选的不带电荷的有机基团为-CH3、-C2H5和-OCH3。
优选的蓝色三苯二噁嗪染料具有以下形式:
其中D和E环被活性基团取代。优选D和E环被磺酸盐基(SO3Na)进一步取代。
活性蓝色染料的实例是活性蓝2、活性蓝4、活性蓝5、活性蓝7、活性蓝15、活性蓝19、活性蓝27、活性蓝29、活性蓝49、活性蓝50、活性蓝74、活性蓝94、活性蓝246、活性蓝247、活性蓝247、活性蓝166、活性蓝109、活性蓝187、活性蓝213、活性蓝225、活性蓝238、活性蓝256。以下举例说明了更多结构:
活性红染料优选选自单偶氮和双偶氮染料。
优选的活性红偶氮染料具有以下形式:
其中F环任选地扩展以来形成萘基并任选地被选自磺酸盐基(SO3Na)和活性基团的基团所取代。
G选自活性基团、H或烷基。活性基团必须存在于染料上。
活性红染料的实例是活性红2、活性红3、活性红4、活性红8、活性红9、活性红12、活性红13、活性红17、活性红22、活性红24、活性红29、活性红33、活性红139、活性红198和活性红141。
活性黄和活性橙染料优选选自单偶氮染料。活性黄和活性橙染料的实例是活性黄1、活性黄2、活性黄3、活性黄16、活性黄17、活性黄25、活性黄39、活性橙107、活性黄176和活性黄135。
可以使用活性染料的组合,以在使用有限数量的染料时得到一组宽广的颜色。优选地,三色体系由三种活性染料的混合物组成。优选地,三色体系含有活性蓝或活性黑染料、活性红和活性黄染料的组合。例如,活性黑5、活性黄176和活性红239;活性蓝176、活性黄176和活性红141。
优选地,每个肽分子应当与至少一个、优选多于两个染料分子共价键合。
为了避免在多种处理时积累差异,如果存在不止一种颜色时,例如活性红和活性蓝,优选将它们键合至同一肽骨架。
优选地,通过使肽与0.1至20重量%、最优选1至10重量%的活性染料反应,能够获得所述染料肽。
肽
肽包含用于与染料反应的游离-SH、-OH、-NH或-NH2基团。更优选地,肽含有至少一个-NH或-NH2基团。
本发明的肽优选具有5至50个、更优选10至25个氨基酸。
优选地,至少一个氨基酸选自精氨酸或赖氨酸,更优选赖氨酸。最优选地,所述肽含有2至3个赖氨酸基团。
当提及聚胺共价结合至活性染料时,本领域技术人员将理解,所述活性基团不再存在于染料肽中。下面对三个活性基团来举例说明这一情况:
通过将头发结合肽(HBP)与带负电荷的活性染料(D)偶联,能够获得本发明的基于肽的头发着色剂。
优选地,每个肽分子应当共价键合至一个染料分子。
可以使用任何肽。所述肽优选是头发结合肽。基于肽的头发着色剂的头发结合肽部分强有力地与头发结合,由此使着色剂保持粘附在头发上长的持续头发着色效果。优选的肽及其合成公开于WO2006/028503中。头发结合肽包括,但不限于通过WO2006/028503、WO2006/094093和WO2006/094094中所述的筛选方法选择的头发结合肽。优选地,肽具有选自WO2006/028503中公开的头发结合肽的至少80%、优选90%、最优选100%的氨基酸序列同源性。特别感兴趣的是WO2006/028503公开的那些SEQ ID NOs:5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40、41、42、43、44、45、46、47、48、49、50、51、52、53、54、55、56、57、58、59、64、66、69和70。对于漂白的头发,也可以使用如SEQ ID NO:60给出的手指甲结合肽。
组合物
除非另外具体说明,下文中引用的所有重量%值是基于头发处理组合物总重的重量百分比。
在组合物是头发调理组合物的情况下,其将优选进一步包含调理活性剂,如脂肪醇和/或脂肪酸和/或脂肪酯和/或脂肪酰胺,和/或阳离子表面活性剂和/或硅氧烷,来改善头发的感觉。
如果组合物在水性基中配制,则是优选的。
优选地,组合物具有2至11的pH,更优选3至9。
可以通过使用常用的缓冲剂和/或碱(如NaOH、NH4OH)和/或酸(如HCl)来控制所述pH。
产品形式
本发明的组合物被配制成可以采取各种形式的头发着色组合物,包括例如摩丝、凝胶、洗剂、霜剂、喷雾和养发剂(tonics)。这些产品形式是本领域公知的。
优选产品是洗剂、霜剂、喷雾、气溶胶摩丝或凝胶。
本发明特别适合于染人头发。
施用方法
施用方法是将组合物施用于头发,优选施用于湿发,在通过漂洗除去之前,组合物优选保留在头发上最多60分钟,更优选最多30分钟。
实施例
现在将通过以下非限制性实施例来说明本发明。
实施例1
根据WO2006/028503制备了具有以下序列的肽:
(a)Thr Asp Met Gln Ala Pro Thr Lys Ser Tyr Ser Asn
(b)Trp His Asp Lys Pro Gln Asn Ser Ser Lys Ser Thr
(c)Gly Pro His Asp Thr Ser Gly Gly Val Arg Pro Asn Leu His His ThrSer Lys Lys Glu Lys Arg Glu Asn Arg Lys Val Pro Phe Tyr Ser His Ser ValThr Ser Arg Gly Asn Val。
将肽(a)加入脱盐水中,使得肽:水的重量比为20:1。向此中加入具有以下结构的双偶氮染料:
肽:活性染料的摩尔比为2:1。将溶液加热至343K,并且混合45分钟,然后加入100g/L的苏打粉(soda ash)。将溶液在343K下再搅拌45分钟,接着冷却,并使用2M HCl将pH调节至7。优选地,组合物含有总组合物的0.2至10重量%的染料聚合物,更优选0.5至3重量%。
对肽(b)和(c)重复实验,除了使用以下染料的1:1混合物:
当施用于漂白的金发上时,获得了蓝/黑色。
Claims (10)
1.包含肽染料的染料组合物,所述肽染料包含共价键合至带负电荷的活性染料的肽;其中通过使含有伯胺、仲胺、OH、SH基团或混合的肽与带负电荷的活性染料反应,能够获得所述肽染料。
2.根据权利要求1的染料组合物,其中所述肽包含至少一个具有包含氨基的侧链的氨基酸。
3.根据前述权利要求任一项的染料组合物,其中所述肽包含至少一个选自精氨酸或赖氨酸的氨基酸,优选赖氨酸。
4.根据前述权利要求任一项的染料组合物,其中所述肽具有选自以下的至少80%、优选90%、最优选100%的氨基酸序列同源性:
(a)Thr Asp Met Gln Ala Pro Thr Lys Ser Tyr Ser Asn
(b)Trp His Asp Lys Pro Gln Asn Ser Ser Lys Ser Thr
(c)Gly Pro His Asp Thr Ser Ser Gly Gly Val Arg Pro Asn Leu His HisThr Ser Lys Lys Glu Lys Arg Glu Asn Arg Lys Val Pro Phe Tyr Ser His SerVal Thr Ser Arg Gly Asn Val。
5.根据权利要求1至4中任一项的染料组合物,其中所述头发结合肽是7至25个氨基酸并且对头发具有测量为MB50等于或小于10-5M的结合亲和性。
6.根据前述权利要求任一项的染发组合物,其中所述组合物包含低于100ppm水解活性染料/10000ppm染料肽。
7.根据前述权利要求任一项的染料组合物,其包含总组合物的0.2重量%至10重量%的头发染料肽。
8.根据前述权利要求任一项的染料组合物,其中所述活性染料包括选自如下的活性基团:二氯三嗪基、二氟氯嘧啶、单氟三嗪基、二氯喹喔啉、乙烯基砜、二氟三嗪、单氯三嗪基、溴代丙烯酰胺和三氯嘧啶。
9.根据前述权利要求任一项的组合物,其是头发染料组合物。
10.染发的方法,其包括向头发施用如前述利要求任一项中所述的组合物的步骤。
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EP11159379 | 2011-03-23 | ||
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EP11171289.9 | 2011-06-24 | ||
PCT/EP2012/055085 WO2012126987A1 (en) | 2011-03-23 | 2012-03-22 | Peptide-based hair colorants |
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AR (1) | AR085480A1 (zh) |
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CN106456489A (zh) * | 2014-04-14 | 2017-02-22 | 荷兰联合利华有限公司 | 皮肤护理组合物 |
CN106456490A (zh) * | 2014-04-14 | 2017-02-22 | 荷兰联合利华有限公司 | 皮肤护理组合物 |
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US10689801B2 (en) | 2014-04-22 | 2020-06-23 | Millikan & Company | Colored coatings and artificial leathers containing colorant complexes |
US20150299468A1 (en) | 2014-04-22 | 2015-10-22 | Milliken & Company | Organic Colorant Complexes from Reactive Dyes and Articles Containing the Same |
EP3015135B1 (en) | 2014-10-29 | 2020-09-09 | Noxell Corporation | Hair colouration with a cationic or anionic coloured polymer, method and kit thereof |
EP3015134B1 (en) | 2014-10-29 | 2020-08-26 | Noxell Corporation | Hair colouration with a cationic coloured polymer, method and kit thereof |
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FR1310583A (fr) * | 1961-10-06 | 1962-11-30 | Ciba Geigy | Colorants hautement polymérisés, leur procédé de préparation et leur emploi |
FR2361447A1 (fr) | 1976-08-12 | 1978-03-10 | Oreal | Composes colorants constitues de polymeres cationiques hydrosolubles et compositions tinctoriales les contenant |
FR2456764A2 (fr) | 1979-05-18 | 1980-12-12 | Oreal | Nouveaux polymeres colorants, leur preparation et leur utilisation |
US5192332A (en) * | 1983-10-14 | 1993-03-09 | L'oreal | Cosmetic temporary coloring compositions containing protein derivatives |
US7220405B2 (en) | 2003-09-08 | 2007-05-22 | E. I. Du Pont De Nemours And Company | Peptide-based conditioners and colorants for hair, skin, and nails |
US20060199206A1 (en) | 2005-03-01 | 2006-09-07 | Hong Wang | Method for identifying skin care composition-resistant skin-binding peptides |
US20070196305A1 (en) | 2005-03-01 | 2007-08-23 | Hong Wang | Method for identifying hair conditioner-resistant hair-binding peptides and hair benefit agents therefrom |
MX2008006914A (es) * | 2005-12-01 | 2008-11-28 | Basf Se | Moleculas efectoras que se unen a la queratina, que contienen tintes reactivos. |
KR101454698B1 (ko) | 2006-07-18 | 2014-10-27 | 시바 홀딩 인코포레이티드 | 중합체 모발 염료 |
WO2009090121A1 (en) | 2008-01-17 | 2009-07-23 | Basf Se | Polymeric hair dyes |
BRPI0906916B1 (pt) | 2008-01-17 | 2018-07-17 | Basf Se | método para tingir cabelo |
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CN106456489A (zh) * | 2014-04-14 | 2017-02-22 | 荷兰联合利华有限公司 | 皮肤护理组合物 |
CN106456490A (zh) * | 2014-04-14 | 2017-02-22 | 荷兰联合利华有限公司 | 皮肤护理组合物 |
CN106456490B (zh) * | 2014-04-14 | 2019-11-01 | 荷兰联合利华有限公司 | 皮肤护理组合物 |
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