CN1437578A - (对氨基羟基苯基)丙烯酰胺衍生物和含有这些化合物的染色剂 - Google Patents

(对氨基羟基苯基)丙烯酰胺衍生物和含有这些化合物的染色剂 Download PDF

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CN1437578A
CN1437578A CN01811523A CN01811523A CN1437578A CN 1437578 A CN1437578 A CN 1437578A CN 01811523 A CN01811523 A CN 01811523A CN 01811523 A CN01811523 A CN 01811523A CN 1437578 A CN1437578 A CN 1437578A
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amino
diamino
hydroxyethyl
alkyl
group
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CN1205179C (zh
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L·查索特
H－J·布朗
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Procter and Gamble Deutschland GmbH
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Wella GmbH
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
  • Pyrane Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Furan Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

本发明涉及通式(I)的(对氨基羟基苯基)丙烯酰胺衍生物或其生理耐受的水溶性盐以及含有这些化合物的用于氧化染色角蛋白纤维的染色剂。

Description

(对氨基羟基苯基)丙烯酰胺衍生物和 含有这些化合物的染色剂
本发明涉及新的(对氨基羟基苯基)丙烯酰胺衍生物和含有这些化合物的用于染色角蛋白纤维，特别是人发的染色剂。
在角蛋白纤维染色，特别是染发领域，氧化染料已发挥很大重要性。在这种情况下，在有适宜氧化剂的情况下通过某些显色剂与某些成色剂产生色彩。适宜的显色剂尤其是2，5-二氨基甲苯、2，5-二氨基苯基乙醇、对氨基苯酚、1，4-二氨基苯和4，5-二氨基吡唑-1-(2-羟基乙基)，而适宜的成色剂例如有间苯二酚、2-甲基间苯二酚、1-萘酚、3-氨基苯酚、间苯二胺、2-氨基-4-(2’-羟基乙基)氨基茴香醚、1，3-二氨基-4-(2’-羟基乙氧基(苯)和2，4-二氨基-5-氟甲苯。
除了能够产生所需强度的色彩之外，用于人头发染色的氧化染料必需满足许多要求。例如，从毒理学和皮肤病理学角度这些染料必需无害，并且获得的头发色彩必需具有良好的耐晒牢度、烫发耐性、耐酸性和耐擦性。然而，在任何情况下，在没有暴露于光、摩擦和化学物质作用的情况下，这些色彩必需稳定保持至少4-6周。而且，通过将适当的显色剂和成色剂混合，必需可以产生广泛的不同色泽。
为了在红色区域获得天然，特别是流行色泽，尤其将对氨基苯酚，与其它显色剂混合或单独，与适宜的成色剂混合使用。已经尝试了通过引入取代基提高对氨基苯酚的性能。在这一点上，读者参考DE-OS196 07 751，它描述了含有特定取代的对氨基苯酚衍生物，例如5-氨基-2-羟基肉桂酸作为显色剂的染色剂。
然而就目前已知的染色剂而言，不能在所有方面满足对染色剂提出的要求。因此，一直特别需要能够满足前述要求的新的显色剂。
在这方面我们已出人意料地发现，通式(I)的新的(对氨基羟基苯基)丙烯酰胺衍生物很大程度上满足了对显色剂提出的要求。事实上，当这些显色剂与大多数已知成色剂一起使用时，它们呈现异常耐晒且耐洗的强的色泽。
因此本发明的目的是通式(I)的(对氨基羟基苯基)丙烯酰胺衍生物或其生理耐受的水溶性盐
Figure A0181152300091
R1代表氢、卤原子(F、Cl、Br、I)、C1-C4-烷基、C1-C4-羟基烷基或C1-C4-烷氧基；
R2和R3各自独立地代表氢或C1-C6-烷基；
R4和R5各自独立地代表氢、C1-C2-烷氧基、C1-C6-烷基、不饱和C3-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、C2-C4-氨基烷基、C2-C4-二甲基氨基烷基、C2-C4-乙酰基氨基烷基、C2-C4-甲氧基烷基、C2-C4-乙氧基烷基、C1-C4-氰基烷基、C1-C4-羧基烷基、C1-C4-氨基羰基烷基、吡啶基甲基、糠基、噻吩基甲基、氢化糠基、取代的吡啶基、式(II)的基团
式(III)的基团
或式(IV)的基团
或者R4和R5与氮原子一起形成下式的环
R6代表氢、羧基或氨基羰基；
R7和R8各自单独地代表氢、羟基、氨基羰基、甲硫基甲基、苯基取代的或羟基取代的苯基或下式的基团
Figure A0181152300103
R9、R10、R11、R12和R13各自独立地代表氢、卤原子(F、Cl、Br、I)、氰基、羟基、C1-C4-烷氧基、C1-C4-羟基烷氧基、C1-C6-烷基、C1-C4-烷基硫醚基、巯基、硝基、氨基、烷基氨基、C1-C4-羟基烷基氨基、二烷基氨基、二(C1-C4-羟基烷基)氨基、(C3-C4-二羟基烷基)氨基、(C1-C4-羟基烷基)-C1-C4-烷基氨基、三氟甲基、-C(O)H基团、-C(O)CH3-基团、-C(O)CF3基团、-Si(CH3)3基团、C1-C4-羟基烷基或C3-C4-二羟基烷基、或者两个相邻的R9-R13基团形成-O-CH2-O-桥；
R14代表C1-C4-烷基、苄基或C2-C4-羟基烷基；
R15代表氢或C1-C6-烷基；
R16代表氢、羟基、羧基、氨基羰基或羟基甲基；和
R17代表氢或C1-C6-烷基。
式(I)的适宜化合物例如是以下的：3-(5-氨基-2-羟基苯基)-N-环丙基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-丙基丙烯酰胺、3-(5-氨基-2-羟基苯基)-1-吡咯烷-1-基丙烯酮、3-(5-氨基-2-羟基苯基)-N-(2-甲氧基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-1-吗啉-4-基丙烯酮、3-(5-氨基-2-羟基苯基)-N-(1-羟基甲基丙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-呋喃-2-基甲基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-甲氧基-N-甲基丙烯酰胺、3-(5-氨基-2-羟基苯基)-1-(4-甲基哌嗪-1-基)-丙烯酮、3-(5-氨基-2-羟基苯基)-1-(4-羟基哌啶-1-基)-丙烯酮、N-(2-乙酰基氨基乙基)-3-(5-氨基-2-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(2-吗啉-4-基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-[3-(2-氧代吡咯烷-1-基)丙基]丙烯酰胺、N-烯丙基-3-(5-氨基-2-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(2-羟基-1-甲基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-[2-(5-硝基吡啶-2-基-氨基)乙基]丙烯酰胺、N-(2-氨基乙基)-3-(5-氨基-2-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(3-咪唑-1-基丙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(四氢呋喃-2-基甲基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-氨基苯基)丙烯酰胺、N-[4-氨基-2(3)-(2-羟基乙基)苯基]-3-(5-氨基-2-羟基苯基)-丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-{4-[二-(2-羟基乙基)氨基]苯基}丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(3-氨基苯基)丙烯酰胺、N-[5-氨基-2(4)-(2-羟基乙氧基)苯基]-3-(5-氨基-2-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-[2-氯-4-(2-羟基乙基氨基)-5-硝基苯基]丙烯酰胺、N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(5-氨基-2-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-苯并[1，3]间二氧杂环戊烯-5-基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(2-羟基乙基)-N-甲基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-乙基-N-(2-羟基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-1-(2-羟基甲基吡咯烷-1-基)丙烯酮、1-[3-(5-氨基-2-羟基苯基)丙烯酰基]吡咯烷-2-羧酰胺、3-(5-氨基-2-羟基苯基)-1-(3-羟基哌啶-1-基)丙烯酮、3-(5-氨基-2-羟基苯基)-N-(2-羟基-1-羟基甲基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-乙基丙烯酰胺、2-[3-(5-氨基-2-羟基苯基)丙烯酰基氨基]-3-甲基丁酸、3-(5-氨基-2-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(1-氨基甲酰基-2-羟基乙基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-氨基-2(3)-甲基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(3-羟基-4-甲基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(2-羟基-5-硝基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)丙烯酸、3-(2-氨基-5-羟基苯基)-N-环丙基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-丙基丙烯酰胺、3-(2-氨基-5-羟基苯基)-1-吡咯烷-1-基丙烯酮、3-(2-氨基-5-羟基苯基)-N-(2-甲氧基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-1-吗啉-4-基丙烯酮、3-(2-氨基-5-羟基苯基)-N-(1-羟基甲基丙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-呋喃-2-基甲基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-甲氧基-N-甲基丙烯酰胺、3-(2-氨基-5-羟基苯基)-1-(4-甲基哌嗪-1-基)-丙烯酮、3-(2-氨基-5-羟基苯基)-1-(4-羟基哌啶-1-基)-丙烯酮、N-(2-乙酰基氨基乙基)-3-(2-氨基-5-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(2-吗啉-4-基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-[3-(2-氧代吡咯烷-1-基)丙基]丙烯酰胺、N-烯丙基-3-(2-氨基-5-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(2-羟基-1-甲基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-[2-(5-硝基吡啶-2-基-氨基)乙基]丙烯酰胺、N-(2-氨基乙基)-3-(2-氨基-5-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(3-咪唑-1-基丙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(四氢呋喃-2-基甲基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-氨基苯基)丙烯酰胺、N-[4-氨基-2(3)-(2-羟基乙基)苯基]-3-(2-氨基-5-羟基苯基)-丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-{4-[二-(2-羟基乙基)氨基]苯基}丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(3-氨基苯基)丙烯酰胺、N-[5-氨基-2(4)-(2-羟基乙氧基)苯基]-3-(2-氨基-5-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-[2-氯-4-(2-羟基乙基氨基)-5-硝基苯基]丙烯酰胺、N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(2-氨基-5-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-苯并[1，3]间二氧杂环戊烯-5-基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(2-羟基乙基)-N-甲基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-乙基-N-(2-羟基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-1-(2-羟基甲基吡咯烷-1-基)丙烯酮、1-[3-(2-氨基-5-羟基苯基)丙烯酰基]吡咯烷-2-羧酰胺、3-(2-氨基-5-羟基苯基)-1-(3-羟基哌啶-1-基)丙烯酮、3-(2-氨基-5-羟基苯基)-N-(2-羟基-1-羟基甲基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-乙基丙烯酰胺、2-[3-(2-氨基-5-羟基苯基)丙烯酰基氨基]-3-甲基丁酸、3-(2-氨基-5-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(1-氨基甲酰基-2-羟基乙基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(4-氨基-2(3)-甲基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(3-羟基-4-甲基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(2-羟基-5-硝基苯基)丙烯酰胺和3-(2-氨基-5-羟基苯基)丙烯酸及其生理耐受盐。
式(I)的优选化合物是其中如下的那些：(i)R1、R2和R3基团中一个、几个或所有代表氢和/或(ii)R4代表C1-C2-烷基、甲氧基或C2-C4-羟基烷基，并且R5代表C2-C4-羟基烷基和/或(iii)R4和R5各自独立地代表氢、C1-C4-烷基、不饱和C1-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、糠基、式(III)的经取代的苯基或式(IV)的经取代的吡唑基和/或(iv)R4代表氢并且R5代表C1-C4烷基、不饱和C3-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、糠基、式(III)的经取代的苯基或式(IV)的经取代的吡唑基。
特别优选以下的式(I)化合物：3-(5-氨基-2-羟基苯基)-N-乙基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-乙基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-氨基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(4-氨基苯基)丙烯酰胺、N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(5-氨基-2-羟基苯基)丙烯酰胺和N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(2-氨基-5-羟基苯基)丙烯酰胺及其生理耐受盐。
式(I)化合物可以是游离碱或者以其与无机或有机酸的生理耐受盐的形式使用，所述酸例如有盐酸、硫酸、磷酸、乙酸、丙酸、乳酸或柠檬酸。
本发明的式(I)的氨基苯酚衍生物可以通过文献已知的合成方法制备。例如，本发明的这些化合物的合成可以如下进行：
用式NHR4R5的胺来氨解式(V)的经取代的苯
接着去除保护基团和/或还原硝基，
其中Ra代表例如下面文章中所述的适宜的保护基团：OrganicSynthesis，Chapter 3，″Protection for Phenols″，143以下页，Wiley Interscience，1991；Rb代表NHRa或NO2，R18代表羧酸基团，羧酰氯基团、羧酸酯基团或羧酸酐基团，并且R1、R2、R3、R4和R5基团具有与式(I)中相同的含义。
本发明的式(I)的化合物尤其可用作角蛋白纤维的氧化染色剂中的显色剂。它们可以产生广泛的不同色泽，从金黄色经棕色、红紫色，一直到紫色。
因此本发明的另一目的是以显色剂-成色剂组合为基础氧化染色角蛋白纤维，例如头发、毛皮、羽毛或羊毛，特别是人发的试剂，其中作为显色剂含有至少一种式(I)的(对氨基羟基苯基)丙烯酰胺衍生物。
本发明的染色剂含有式(I)的氨基苯酚衍生物，其量为约0.005-20重量％，优选约0.01-5.0重量％，特别优选0.1-2.5重量％。
优选的成色剂是N-(3-二甲基氨基苯基)脲、2，6-二氨基吡啶、2-氨基-4-[(2-羟基乙基)氨基]茴香醚、2，4-二氨基-1-氟-5-甲基苯、2，4-二氨基-1-甲氧基-5-甲基苯、2，4-二氨基-1-乙氧基-5-甲基苯、2，4-二氨基-1-(2-羟基乙氧基)-5-甲基苯、2，4-二[(2-羟基乙基)氨基]-1，5-二甲氧基苯、2，3-二氨基-6-甲氧基吡啶、3-氨基-6-甲氧基-2-(甲基氨基)吡啶、2，6-二氨基-3，5-二甲氧基吡啶、3，5-二氨基-2，6-二甲氧基吡啶、1，3-二氨基苯、2，4-二氨基-1-(2-羟基乙氧基)苯、1，3-二氨基-4-(2，3-二羟基丙氧基)苯、1，3-二氨基-4-(3-羟基丙氧基)苯、1，3-二氨基-4-(2-甲氧基乙氧基)苯、2，4-二氨基-1，5-二(2-羟基乙氧基)苯、1-(2-氨基乙氧基)-2，4-二氨基苯、2-氨基-1-(2-羟基乙氧基)-4-甲基氨基苯、2，4-二氨基苯氧基乙酸、3-[二(2-羟基乙基)氨基]苯胺、4-氨基-2-二[(2-羟基乙基)氨基]-1-乙氧基苯、5-甲基-2-(1-甲基乙基)苯酚、3-[(2-羟基乙基)氨基]苯胺、3-[(2-氨基乙基)氨基]苯胺、1，3-二(2，4-二氨基苯氧基)丙烷、二(2，4-二氨基苯氧基)甲烷、1，3-二氨基-2，4-二甲氧基苯、2，6-二-(2-羟基乙基)氨基甲苯、4-羟基吲哚、3-二甲基氨基苯酚、3-二乙基氨基苯酚、5-氨基-2-甲基苯酚、5-氨基-4-氟-2-甲基苯酚、5-氨基-4-甲氧基-2-甲基苯酚、5-氨基-4-乙氧基-2-甲基苯酚、3-氨基-2，4-二氯苯酚、5-氨基-2，4-二氯苯酚、3-氨基-2-甲基苯酚、3-氨基-2-氯-6-甲基苯酚、3-氨基苯酚、2-[(3-羟基苯基)氨基]乙酰胺、5-[(2-羟基乙基)氨基]-4-甲氧基-2-甲基苯酚、5-[(2-羟基乙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]苯酚、3-[(2-甲氧基乙基)氨基]苯酚、5-氨基-2-乙基苯酚、5-氨基-2-甲氧基苯酚、2-(4-氨基-2-羟基苯氧基)乙醇、5-[(3-羟基丙基)氨基]-2-甲基苯酚、3-[(2，3-二羟基丙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]-2-甲基苯酚、2-氨基-3-羟基吡啶、2，6-二羟基-3，4-二甲基吡啶、5-氨基-4-氯-2-甲基苯酚、1-萘酚、2-甲基-1-萘酚、1，5-二羟基萘、1，7-二羟基萘、2，3-二羟基萘、2，7-二羟基萘、乙酸2-甲基-1-萘酯、1，3-二羟基苯、1-氯-2，4-二羟基苯、2-氯-1，3-二羟基苯、1，2-二氯-3，5-二羟基-4-甲基苯、1，5-二氯-2，4-二羟基苯、1，3-二羟基-2-甲基苯、3，4-亚甲基二氧基苯酚、3，4-亚甲基二氧基苯胺、5-[(2-羟基乙基)氨基]-1，3-苯并间二氧杂环戊烯、6-溴-1-羟基-3，4-亚甲基二氧基苯、3，4-二氨基苯甲酸、3，4-二氢-6-羟基-1，4(2H)苯并噁嗪、6-氨基-3，4-二氢-1，4(2H)苯并噁嗪、3-甲基-1-苯基-5-吡唑啉酮、5，6-二羟基吲哚、5，6-二羟基二氢吲哚、5-羟基吲哚、6-羟基吲哚、7-羟基吲哚和2，3-二氢吲哚二酮。
尽管本文所述的式(I)的氨基苯酚衍生物的有益性表明它们可单独用作显色剂，但是自然也可以将式(I)的对氨基苯酚衍生物与其它已知的显色剂一起使用，例如与1，4-二氨基苯、2，5-二氨基甲苯、2-(2，5-二氨基苯基)乙醇、1-(2，5-二氨基苯基)乙醇、N，N-二-(2’-羟基乙基)-1，4-二氨基苯、4-氨基苯酚及其衍生物，例如4-氨基-3-甲基苯酚、吡唑衍生物，例如4，5-二氨基-1-(2-羟基乙基)吡唑、4，5-二氨基-1-苄基吡唑和4，5-二氨基-1-(4-甲基苄基)吡唑、或四氨基嘧啶。
这些成色剂和显色剂可以单独或者以彼此的混合物存在于本发明染色剂中，所述成色剂和显色剂在本发明染色剂中的总量分别为约0.005-20重量％，优选约0.01-5重量％，特别优选0.1-2.5重量％(以染色剂的总量为基础)。
本文所述的染色剂中所含的显色剂-成色剂组合的总量优选为约0.01-20重量％，特别是约0.02-10重量％，特别优选0.2-6.0重量％。一般说来，这些显色剂和成色剂以大致等摩尔量使用。在这一点上，如果显色剂以某一过量或不足量存在，那么也不是不利的。
而且，本发明的染色剂也可以含有其它染料成分，例如6-氨基-2-甲基苯酚和2-氨基-5-甲基苯酚，以及常规直接染料，例如三苯基甲烷染料如4-[(4’-氨基苯基)-(4’-亚氨基-2″，5″-环己二烯-1″-亚基)甲基]-2-甲基氨基苯单盐酸盐(C.I.42 510)和4-[(4’-氨基-3’-甲基苯基)-(4″-亚氨基-3″-甲基-2″，5″-环己二烯-1″-亚基)甲基]-2-甲基氨基苯单盐酸盐(C.I.42 520)、芳香硝基染料如4-(2’-羟基乙基)氨基硝基甲苯、2-氨基-4，6-二硝基苯酚、2-氨基-5-(2’-羟基乙基)氨基硝基苯、2-氯-6-(乙基氨基)-4-硝基苯酚、4-氯-N-(2-羟基乙基)-2-硝基苯胺、5-氯-2-羟基-4-硝基苯胺、2-氨基-4-氯-6-硝基苯酚和1-[(2’-脲基乙基)氨基-4-硝基苯、偶氮染料如6-[(4’-氨基苯基)偶氮]-5-羟基萘-1-磺酸钠(C.I.14 805)和分散染料，例如1，4-二氨基蒽醌和1，4，5，8-四氨基蒽醌。本发明的这些染色剂可以含有约0.1-4重量％的量的前述染料成分。
这些成色剂和显色剂以及其它染料成分，只要它们是碱，当然它们也可以以其与有机或无机酸如盐酸或硫酸的生理耐受盐的形式使用，或者如果它们含有芳香OH基，可以以其与碱的盐的形式，例如碱金属酚盐使用。
而且，如果这些染色剂将用于头发染色，它们还可以含有其它常规化妆添加剂，例如抗氧化剂如抗坏血酸、巯基乙酸或亚硫酸钠，以及芳香油，络合剂、湿润剂、乳化剂、增稠剂和护理剂。
本发明的染色剂可以是例如溶液的形式，特别是含水或含水-醇的溶液。然而，特别优选的制品形式是膏、凝胶或乳剂。这些组合物由染料组分和用于这些组合物的常规添加剂的混合物组成。
溶液、膏、乳剂或凝胶的常规添加剂例如有，溶剂如水，低级脂族醇，例如乙醇、丙醇或异丙醇，甘油或二醇如1，2-丙二醇，以及湿润剂或来自阴离子、阳离子、两性或非离子表面活性剂类的乳化剂，例如脂肪醇硫酸酯、乙氧基化脂肪醇硫酸酯、烷基磺酸盐、烷基苯磺酸盐、烷基三甲基铵盐、烷基甜菜碱、乙氧基化脂肪醇、乙氧基化壬基苯酚、脂肪酸链烷醇酰胺和乙氧基化脂肪酸酯，以及增稠剂如高级脂肪醇、淀粉、纤维素衍生物、矿脂、石蜡油和脂肪酸，还有护理剂如阳离子树脂、羊毛脂衍生物、胆固醇、泛酸和甜菜碱。所述成分以常用于这些目的的量使用，例如湿润剂和乳化剂以约0.5-30重量％的浓度，增稠剂以约0.1-30重量％的量，护理剂以约0.1-5重量％的浓度。
根据其组成，本发明的染色剂可以为弱酸性、中性或碱性。具体地说，它可以具有约6.5-11.5的pH值。优选用氨水调整至碱性pH，但是它也可以用有机胺调整，例如用一乙醇胺和三乙醇胺，或者用无机碱如氢氧化钠和氢氧化钾。可以用无机或有机酸，例如磷酸、乙酸、柠檬酸或酒石酸调整至酸性pH。
就氧化头发染色而言，就在使用前将前述的染色剂与氧化剂混合，而且根据头发密度，将足够头发处理的量，通常为约60-200克的该混合物涂敷到头发上。
使头发染色显色的适宜氧化剂主要是过氧化氢或其与脲、蜜胺、硼酸钠或碳酸钠的加合产物，以3-12％，优选6％水溶液的形式，空气氧也是适宜的。当使用6％过氧化氢溶液作为氧化剂时，头发染色剂与氧化剂的重量比是5∶1-1∶2，优选1∶1。尤其当头发染色剂中染料浓度较高或者同时想要较强地漂洗头发时，使用较高量的氧化剂。在15-50℃下使混合物在头发上作用约10-45分钟，优选30分钟。然后用水将头发冲洗并干燥。任选，在冲洗之后，头发用香波洗涤，任选用弱有机酸如柠檬酸或酒石酸再冲洗。然后将头发干燥。
含有式(I)的对氨基苯酚衍生物作为显色剂的本发明染色剂具有头发染色的优异色彩耐牢度，特别是耐晒性、耐洗性和耐擦性。至于染色性能，本发明的头发染色剂赋予了广泛的不同色泽，从金黄色经棕色、红色、紫色直至蓝色和黑色，这取决于所用染料组分的种类和组成。这些色泽突出在于其不寻常的色彩强度以及在损坏和未损坏头发之间的良好的色彩平衡。本专利申请的头发染色剂的非常好的染色性能此外还在于，这些染色剂可以毫无问题地染花白的，先前没有被化学损坏的头发，并且具有良好覆盖力。
以下实施例非限制性地详细描述了本发明的主题。
                      实施例实施例1 合成式(I)的(对氨基羟基苯基)丙烯酰胺衍生物(一般合成方法)A. 合成N-(3-溴-4-羟基苯基)氨基甲酸叔丁酯
在0℃下2小时内将9.4g(52.8mmol)N-溴琥珀酰亚胺的450mL氯仿溶液滴加到10g(47.8mmol)N-(4-羟基苯基)氨基甲酸叔丁酯的100mL氯仿悬液中。将该反应混合物再搅拌15分钟，之后用水洗2次(首先用400mL，然后用200mL)，用硫酸镁干燥并过滤，将滤液部分蒸发。然后边搅拌边向该残余物中加入己烷，形成沉淀。过滤出沉淀物并用己烷洗涤。
这样得到9.7g(理论值的70％)的N-(3-溴-4-羟基苯基)氨基甲酸叔丁酯。B. 合成N-(3-溴-4-乙氧基甲氧基苯基)氨基甲酸叔丁酯
在0℃下将0.76g(17.4mmol)氢化钠分散液(55％的油中)一份一份地加入到5g(17.4mmol)N-(3-溴-4-羟基苯基)氨基甲酸叔丁酯的60mL四氢呋喃溶液中。将该混合物于0℃下搅拌50分钟，之后加入1.83g(19.4mmol)氯甲基乙基醚。将该混合物于0℃下搅拌另一小时。然后将其倒在冰上并用乙酸乙酯萃取，有机相用饱和氯化钠水溶液洗涤，在Na2SO4上干燥并过滤，将滤液蒸发。残余物在硅胶上用石油醚/乙酸乙酯(9∶1)提纯。
这样得到4.8g(理论值的80％)的N-(3-溴-4-乙氧基甲氧基苯基)氨基甲酸叔丁酯。1 H-NMR(300MHz，CDCl3)： δ＝7,67(d，1H)；7,16(dd，1H)；7,07(d，1H)；7,21 6,40(br，1H)；5,23(s，2H)；3,77(q，2H)；1,51(s，9H)；1,22(t，3H)C. 合成N-(4-乙氧基甲氧基-3-甲酰基苯基)氨基甲酸叔丁酯
在氩气下将3.3g(0.01mol)步骤A的(3-溴-4-叔丁氧基羰基氨基苯基)氨基甲酸叔丁酯溶于100mL无水四氢呋喃中。然后，逐步加入17mL(＝0.03mol)1.6M甲基锂乙醚溶液。将反应混合物冷却至-20℃，并逐步加入7ml(＝0.01mol)的1.5M的叔丁基锂，加入结束时，在所述温度下将溶液搅拌另外30分钟。然后，加入1.2g(0.02mol)二甲基甲酰胺，在-20℃下将该反应混合物搅拌1小时。然后慢慢加热至0℃并用10％磷酸盐缓冲液水解并倒在乙酸乙酯上。水相用乙酸乙酯萃取，有机相用硫酸镁干燥。在旋转蒸发器中将溶剂蒸发掉，并向残余物中加入己烷。然后过滤出最终的黄色沉淀，用己烷洗涤并干燥。
这样得到2.0g(理论值的70％)的N-(4-乙氧基甲氧基-3-甲酰基苯基)氨基甲酸叔丁酯。1H-NMR(300MHz，CDCl3)：δ＝10,43(s，1H)；7,73(d，1H)；7,61(d，1H)；7,20(d，1H)；6,45(br，1H)；5,31(s，2H)；3,75(q，2H)；1,51(s，9H)；1,23(t，3H)D. 合成3-(5-叔丁氧基羰基氨基-2-乙氧基甲氧基苯基)丙烯酸甲酯
将8.9g(0.03mol)步骤C的N-(乙氧基甲氧基-2-甲酰基苯基)氨基甲酸叔丁酯溶于70mL四氢呋喃中，并向所得溶液中加入11.9g(0.036mol)甲氧基羰基亚甲基三苯基正膦。在室温下将反应混合物搅拌3小时。然后将混合物倒入水中并用乙酸乙酯萃取，有机相用饱和氯化钠水溶液洗涤，在硫酸钠上干燥并过滤，并将滤液蒸发。
在硅胶上用己烷/乙酸乙酯将该粗产物快速色谱纯化得到10.5g(理论值的95％)的产品。将该产品悬浮于己烷/二乙醚(10∶1)中，并随后从乙酸乙酯/己烷中结晶获得其纯E-异构体。1 H-NMR(300MHz，CDCl3)： δ＝7,99(d，1H)；7,60(br s，1H)；7,26(dd，1H)；7,12(d，1H)；6,50(d，1H)；6,42(brs，1H)；5,25(s，2H)；3,79(s，-3H)；3,73(q，2H)；1,51(s，9H)；1,21(t，3H)E. 合成3-(5-叔丁氧基羰基氨基-2-乙氧基甲氧基苯基)丙烯酸
在0℃下将2.53g(0.06mol)氢氧化锂一水合物加入到6.3g(0.018mol)步骤D的3-(5-叔丁氧基羰基氨基-2-乙氧基甲氧基苯基)丙烯酸甲酯的50mL四氢呋喃、15mL甲醇和30mL水的溶液中。在60℃下将混合物搅拌24小时。然后将该反应混合物倒在磷酸盐缓冲液(pH7.0)上并用乙酸乙酯萃取，有机相用饱和氯化钠水溶液洗涤，然后在硫酸钠上干燥。将该有机相部分蒸发至开始形成沉淀，然后加入己烷。过滤掉沉淀物并用50mL己烷洗涤。这样得到5.4g(理论值的89％)的3-(5-叔丁氧基羰基氨基-2-乙氧基甲氧基苯基)丙烯酸。1 H NMR(300MHz，DMSO-D6)： δ＝12,4(br，1H)；9,22(br s，1H)；7,81(d，1H)；7,73(d，1H)；7,42(dd，1H)；7,10(d，1H)；6,33(d，1H)；5,27(s，2H)；3,67(q，2H)；1,48(s，9H)；1,13(t，3H)F. 合成3-(5-氨基-2-羟基苯基)丙烯酰胺衍生物
向反应器中倒入0.07g(0.185mmol)3-(5-叔丁氧基羰基氨基-2-乙氧基甲氧基苯基)丙烯酸、0.037g(0.24mmol)N-羟基苯并三唑水合物和0.043g(0.22mmol)N-(3-二甲基氨基丙基)-N’-乙基碳二亚胺盐酸盐的二氯甲烷的混合物。向其中加入相应的胺(0.22mmol)和0.047g N-乙基二异丙基胺，在室温下将该混合物摇动12小时。反应结束时，将反应混合物倒入10mL乙酸乙酯。其有机相然后用碳酸氢钠萃取并用硫酸镁干燥。在旋转蒸发器中将溶剂蒸馏掉并且残余物在硅胶上用适宜洗脱剂(例如，石油醚/乙酸乙酯或二氯甲烷/甲醇)提纯。将所得产物在4mL乙醇中加热到50℃。为了制备其盐酸盐，滴加1.5mL 2.9M盐酸乙醇溶液。将溶液蒸发，并将残余物干燥。a. 3-(5-氨基-2-羟基苯基)-N-乙基丙烯酰胺盐酸盐
所用胺：乙胺
质谱：MH+207(100)b. 3-(5-氨基-2-羟基苯基)-N-(4-羟基苯基)丙烯酰胺盐酸盐所用胺：4-羟基苯甲醛
质谱：MH+ 271(100)c. 3-(5-氨基-2-羟基苯基)-N-(4-氨基苯基)丙烯酰胺盐酸盐
所用胺：4-氨基苯基氨基甲酸叔丁酯
质谱：MH+ 270(100)d. N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(5-氨基-2-羟基苯 基)丙烯酰胺盐酸盐
所用胺：4，5-二氨基-1-(2-羟基乙基)吡唑
质谱：MH+ 269(100)e. N-烯丙基-3-(5-氨基-2-羟基苯基)丙烯酰胺盐酸盐
所用胺：烯丙基胺
质谱：MH+ 304(100)f. 3-(5-氨基-2-羟基苯基)-N-环丙基丙烯酰胺盐酸盐
所用胺：环丙基胺
质谱：MH+ 219(100)g. N-(2-氨基乙基)-3-(5-氨基-2-羟基苯基)丙烯酰胺盐酸盐
所用胺：乙二胺
质谱：MH+ 222(100)h. 3-(5-氨基-2-羟基苯基)-N-[4-氨基-2(3)-甲基苯基]丙烯酰胺盐 酸盐
所用胺：(4-氨基-2-甲基苯基)氨基甲酸叔丁酯和(4-氨基-3-甲基苯基)氨基甲酸叔丁酯
质谱：MH+ 284(100)i. 3-(5-氨基-2-羟基苯基)-N-异丙基丙烯酰胺盐酸盐
所用胺：异丙基胺
质谱：MH+ 221(100)j. 3-(5-氨基-2-羟基苯基)-N-丙基丙烯酰胺盐酸盐
所用胺：丙基胺
质谱：MH+ 221(100)k. 3-(5-氨基-2-羟基苯基)-1-吡咯烷-1-基丙烯酮盐酸盐
所用胺：吡咯烷
质谱：MH+ 233(100)1. 3-(5-氨基-2-羟基苯基)-N-(2-甲氧基乙基)丙烯酰胺盐酸盐
所用胺：2-甲氧基乙基胺
质谱：MH+ 237(100)m. 3-(5-氨基-2-羟基苯基)-1-吗啉-4-基丙烯酮盐酸盐
所用胺：吗啉
质谱：MH+ 249(100)n. 3-(5-氨基-2-羟基苯基)-N-(1-羟基甲基丙基)丙烯酰胺盐酸盐
所用胺：2-氨基-1-丁醇
质谱：MH+ 251(100)o. 3-(5-氨基-2-羟基苯基)-N-呋喃-2-基甲基丙烯酰胺盐酸盐
所用胺：糠基胺
质谱：MH+ 259(100)p. 3-(5-氨基-2-羟基苯基)-N-甲氧基-N-甲基丙烯酰胺盐酸盐
所用胺：N，O-二甲基羟基胺盐酸盐
质谱：MH+ 223(100)q. 3-(5-氨基-2-羟基苯基)-1-(4-甲基哌嗪-1-基)丙烯酮盐酸盐
所用胺：4-甲基哌嗪
质谱：MH+ 262(100)r. 3-(5-氨基-2-羟基苯基)-1-(4-羟基哌啶-1-剂)丙烯酮盐酸盐
所用胺：4-羟基哌啶
质谱：MH+ 263(100)s. N-(2-乙酰基氨基乙基)-3-(5-氨基-2-羟基苯基)丙烯酰胺盐酸盐
所用胺：N-乙酰基乙二胺
质谱：MH+ 264(100)t. 3-(5-氨基-2-羟基苯基)-N-(2-吗啉-4-基乙基)丙烯酰胺盐酸盐
所用胺：4-(2-乙基氨基)吗啉
质谱：MH+ 292(100)u. 3-(5-氨基-2-羟基苯基)-N-[3-(2-氧代吡咯烷-1-基)丙基]丙烯酰 胺盐酸盐
所用胺：1-(3-氨基丙基)-2-吡咯烷酮
质谱：MH+ 304(100)v. 3-(5-氨基-2-羟基苯基)-N-(2-羟基-1-甲基乙基)丙烯酰胺盐酸盐
所用胺：2-氨基丙醇
质谱：MH+ 237(100)w. 3-(5-氨基-2-羟基苯基)-N-[2-(5-硝基吡啶-2-基氨基)乙基]丙烯 酰胺盐酸盐
所用胺：2-氨基-5-硝基吡啶
质谱：MH+ 344(100)x. 3-(5-氨基-2-羟基苯基)-N-(3-咪唑-1-基丙基)丙烯酰胺盐酸盐
所用胺：1-(3-氨基丙基)咪唑
质谱：MH+ 287(100)y. 3-(5-氨基-2-羟基苯基)-N-(四氢呋喃-2-基甲基)丙烯酰胺盐酸盐
所用胺：四氢糠基胺
质谱：MH+ 263(100)z. N-[4-氨基-2(3)-(2-羟基乙基)苯基]-3-(5-氨基-2-羟基苯基)丙 烯酰胺盐酸盐
所用胺：[4-氨基-2-(2-羟基乙基)苯基]氨基甲酸叔丁酯和[4-氨基-3-(2-羟基乙基)苯基]氨基甲酸叔丁酯
质谱：MH+ 314(100)aa. 3-(5-氨基-2-羟基苯基)-N-{4-[二-(2-羟基乙基)氨基]苯基}丙 烯酰胺盐酸盐
所用胺：4-二-(2-羟基乙基)氨基苯胺
质谱：MH+ 358(100)ab. 3-(5-氨基-2-羟基苯基)-N-(3-氨基苯基)丙烯酰胺盐酸盐
所用胺：(3-氨基苯基)氨基甲酸叔丁酯
质谱：MH+ 270(100)ac. N-[5-氨基-2(4)-(2-羟基乙氧基)苯基]-3-(5-氨基-2-羟基苯基) 丙烯酰胺盐酸盐
所用胺：[3-氨基-4-(2-羟基乙氧基)苯基]氨基甲酸叔丁酯和[3-氨基-6-(2-羟基乙氧基)苯基]氨基甲酸叔丁酯
质谱：MH+ 330(100)ad. 3-(5-氨基-2-羟基苯基)-N-[2-氯-4-(2-羟基乙基氨基)-5-硝基 苯基]丙烯酰胺盐酸盐
所用胺：2-氯-4-(2-羟基乙基)氨基-5-硝基苯胺
质谱：MH+ 393(100)ae. 3-(5-氨基-2-羟基苯基)-N-苯并[1，3]间二氧杂环戊烯-5-基丙烯 酰胺盐酸盐
所用胺：苯并[1，3]间二氧杂环戊烯-5-基胺
质谱：MH+ 299(100)af. 3-(5-氨基-2-羟基苯基)-N-(2-羟基乙基)-N-甲基丙烯酰胺盐酸 盐
所用胺：2-甲基氨基乙醇
质谱：MH+ 237(100)ag. 3-(5-氨基-2-羟基苯基)-N-乙基-N-(2-羟基乙基)丙烯酰胺盐酸 盐
所用胺：2-乙基氨基乙醇
质谱：MH+ 251(80)ah. 3-(5-氨基-2-羟基苯基)-1-(2-羟基甲基吡咯烷-1-基)丙烯酮盐 酸盐
所用：脯氨醇(prolinol)
质谱：MH+ 263(100)ai. 1-[3-(5-氨基-2-羟基苯基)丙烯酰基]吡咯烷-2-羧酰胺盐酸盐
所用胺：脯氨酰胺
质谱：MH+ 276(100)aj. 3-(5-氨基-2-羟基苯基)-1-(3-羟基哌啶-1-基)丙烯酮盐酸盐
所用胺：3-羟基哌啶
质谱：MH+ 263(100)ak. 3-(5-氨基-2-羟基苯基)-N-(2-羟基-1-羟基甲基乙基)丙烯酰胺 盐酸盐
所用胺：3-氨基-1，2-丙二醇
质谱：MH+ 253(100)al. 2-[3-(5-氨基-2-羟基苯基)丙烯酰基氨基]-3-甲基丁酸盐酸盐
所用胺：α-氨基异戊酸
质谱：MH+ 279(100)am. 3-(5-氨基-2-羟基苯基)-N-(1-氨基甲酰基-2-羟基乙基)丙烯酰 胺盐酸盐
所用胺：2-氨基-3-羟基丙酰胺
质谱：MH+ 266(100)an. 3-(5-氨基-2-羟基苯基)-N-(3-羟基-4-甲基苯基)丙烯酰胺盐酸 盐
所用胺：5-氨基-2-甲基苯酚
质谱：MH+ 285(100)ao. 3-(5-氨基-2-羟基苯基)-N-(2-羟基-5-硝基苯基)丙烯酰胺盐酸 盐
所用胺：2-氨基-4-硝基苯酚
质谱：MH+ 316(100)实施例2-39头发染色剂
制备具有以下组成的头发染色溶液：1.25mmol            按照表1的式(I)的显色剂1.25mmol            按照表1的成色剂1.0g                油酸钾(8％水溶液)1.0g                氨水(22％水溶液)1.0g                乙醇0.3g                抗坏血酸至100.0g            水
就在使用之前，将30g前面的染色溶液与30g的6％过氧化氢水溶液混合。然后将该混合物涂敷到漂洗过的头发上。在40℃下作用30分钟之后，头发用水冲洗，用商购香波洗涤并干燥。所得色泽呈现于表1中。
                                 表1
实施例号   式(I)的显色剂                       成色剂
      II.      III.     IV
硫酸1，3-二氨基-4-(2-羟基乙氧基)苯酯  5-氨基-2-甲基苯酚   1-萘酚
  2   按照实施例1a     棕红色     橙红色   紫色
  3   按照实施例1b     棕红色     橙红色   紫色
  4   按照实施例1c     棕红色     橙红色   紫色
  5   按照实施例1d     棕红色     橙红色   亮紫色
  6   按照实施例1e     棕红色     橙红色   亮紫色
  7   按照实施例1f     棕红色     橙红色   亮紫色
  8   按照实施例1g     棕红色     橙红色   亮紫色
  9   按照实施例1h     棕红色     橙红色   亮紫色
  10   按照实施例1i     棕红色     橙红色   亮紫色
  11   按照实施例1j     棕红色     橙红色   亮紫色
  12   按照实施例1k     棕红色     橙红色   亮紫色
  13   按照实施例1l     棕红色     橙红色   亮紫色
  14   按照实施例1m     棕红色     橙红色   亮紫色
  15   按照实施例1n     棕红色     橙红色   亮紫色
  16   按照实施例1o     棕红色     橙红色   亮紫色
  17   按照实施例1p     棕红色     橙红色   亮紫色
  18   按照实施例1q     棕红色     橙红色   亮紫色
  19   按照实施例1r     棕红色     棕色   亮紫色
  20   按照实施例1s     棕红色     棕红色   亮紫色
  21   按照实施例1t     棕红色     橙红色   亮紫色
  22   按照实施例1u     棕红色     橙红色   亮紫色
  23   按照实施例1v     棕红色     橙红色   亮紫色
  24   按照实施例1x     棕红色     亮橙红色   亮紫色
  25   按照实施例1y     棕红色     亮橙红色   亮紫色
  26   按照实施例1z     棕红色     亮橙红色   亮紫色
  27   按照实施例1aa     棕红色     红色   亮紫色
  28   按照实施例1ab     棕红色     亮橙红色   亮紫色
  29   按照实施例1ac     棕红色     亮橙红色   亮紫色
  30   按照实施例1ae     棕红色     亮橙红色   亮紫色
  31   按照实施例1af     棕红色     亮橙红色   亮紫色
  32   按照实施例1ag     棕红色     亮橙红色   亮紫色
  33   按照实施例1ah     棕红色     亮橙红色   亮紫色
  34   按照实施例1ai     棕红色     亮橙红色   亮紫色
  35   按照实施例1aj     棕红色     亮橙红色   亮紫色
  36   按照实施例1ak     棕红色     亮橙红色   亮紫色
  37   按照实施例1al     棕红色     亮橙红色   亮紫色
  38   按照实施例1am     棕红色     亮橙红色   亮紫色
  39   按照实施例1an     棕红色     亮橙红色   亮紫色
实施例40-71头发染色剂
制备具有以下组成的头发染色溶液：Xg                  按照表3的式(I)的显色剂E1或E2Ug                  按照表3的显色剂E3-E10Yg                  按照表4的成色剂K11-K36Zg                  按照表2的直接染料D1-D310.0g               油酸钾(8％水溶液)10.0g               氨水(22％水溶液)10.0g               乙醇0.3g                抗坏血酸至100.0g            水
就在使用之前，将30g前面的染色溶液与30g的6％过氧化氢水溶液混合。然后将该混合物涂敷到漂洗过的头发上。在40℃下作用30分钟之后，头发用水冲洗，用商购香波洗涤并干燥。表5显示了染色结果。实施例72-77头发染色剂
制备膏状且具有以下组成的染色载体配制物：Xg                  按照表3的式(I)的显色剂E1Ug                  按照表3的显色剂E3-E10Yg                  按照表4的成色剂K11-K36Zg                  按照表2的直接染料D1-D315.0g               十六烷醇0.3g                抗坏血酸3.5g                月桂醇二甘醇醚硫酸钠，28％水溶液3.0g                氨水，22％水溶液0.3g                硫酸钠，无水至100g              水
就在使用之前，将30g前面的染色膏与30g的6％过氧化氢溶液混合。然后将该混合物涂敷到漂洗过的头发上。在作用30分钟之后，头发用水冲洗，用商购香波洗涤并干燥。染色结果示于下表6。
           表2-直接染料
D1  2，6-二氨基-3-((吡啶-3-基)偶氮)吡啶
D2  6-氯-2-乙基氨基-4-硝基苯酚
D3  2-氨基-6-氯-4-硝基苯酚
                  表3-显色剂
E1 3-(5-氨基-2-羟基苯基)-N-乙基丙烯酰胺盐酸盐
E2 3-(5-氨基-2-羟基苯基)-N-(4-氨基苯基)丙烯酰胺盐酸盐
E3 硫酸2，5-二氨基苯基乙酯
E4 3-甲基-4-氨基苯酚
E5 4-氨基-2-氨基甲基苯酚二盐酸盐
E6 4-氨基苯酚
E7 N，N-二-(2’-羟基乙基)-对苯二胺硫酸盐
E8 4，5-二氨基-1-(2’-羟基乙基)吡唑硫酸盐
E9 2，5-二氨基甲苯硫酸盐
E10 1，4-二氨基苯
               表4-成色剂
K11  1，3-二氨基苯
K12  2-氨基-4-(2’-羟基乙基)氨基茴香醚硫酸盐
K13  1，3-二氨基-4-(2’-羟基乙氧基)苯硫酸盐
K14  2，4-二氨基-5-氟甲苯硫酸盐
K16  3，5-二氨基-2，6-二甲氧基吡啶二盐酸盐
K17  2，4-二氨基-5-乙氧基甲苯硫酸盐
K18  N-(3-二甲基氨基)苯基脲
K19  1，3-二-(2，4-二氨基苯氧基)丙烷四盐酸盐
K21  3-氨基苯酚
K22  5-氨基-2-甲基苯酚
K23  3-氨基-2-氯-6-甲基苯酚
K24  5-氨基-4-氟-2-甲基苯酚硫酸盐
K25  1-萘酚
K26  1-乙酰氧基-2-甲基萘
K31  1，3-二羟基苯
K32  2-甲基-1，3-二羟基苯
K33  1-氯-2，4-二羟基苯
K34  4-(2’-羟基乙基)氨基-1，2-亚甲二氧基苯盐酸盐
K35  3，4-亚甲二氧基苯酚
K36  2-氨基-5-甲基苯酚
                          表5-头发染色剂
实施例  40  41  42  43  44  45
 染料                           (染料量，克)
 E1  0.096  0.24  0.30  0.04  0.01  0.70
 E9  0.096  1.80
 E10  0.90
 K11  0.05
 K12  0.01
 K18  0.03
 K21  0.02  0.06
 K22  0.08  0.20  0.25  0.056  0.42
 K24  0.05  0.11
 K25  0.03
 K31  0.20  0.80
 K32  0.03  0.05  0.316
 K35  0.018
 K36  0.03  0.05  0.01
 K26
 D1  0.01
 D3  0.04  0.06  0.025
 色泽  亮金色至金铜色  金铜色  亮铜色  紫褐色  金银色  暗红棕色
                            表5-续
实施例  46  47  48  49  50  51
染料                    (染料量，克)
 E1  0.01  0.60  1.00  0.20  0.80  0.60
 E10  2.00  1.90
 E3  0.05
 E7  0.06
 E8  1.00
 E9  1.00  0.70
 K12  1.10
 K13  0.07  0.80
 K16  1.00
 K17  1.10
 K18  1.25
 K21  0.40  0.28
 K22  0.08  0.40
 K24  0.10
 K25  0.80
 K31  0.80
 K32  0.03
 K33  0.75
 K36  0.03
 D1  0.25
 D3  0.15
 色泽  黑褐色  橙色  蓝紫色  蓝红色  粉红色  枣红色
                 表5-续
实施例  52  53  54  55
染料           (染料量，克)
 E1  0.01  0.01  0.05  0.60
 E3  1.40  4.50
 E5  0.25
 E6  0.10
 E8  0.80  0.50  0.01
 E9  2.50
 K12  0.60
 K13  0.20  0.80
 K14  0.25
 K16  0.01
 K18  1.25
 K19  0.80
 K21  0.30  0.28
 K22  5.00
 K25  0.40
 K23  0.60
 K31  1.10
 K32  0.33
 K36  0.19
 D2  0.50
 色泽  黑色  紫红色  橙红色  暖黄色
                              表5-续
实施例  56  57  58  59  60  61
染料                       (染料量，克)
 E2  0.096  0.24  0.30  0.04  0.01  0.70
 E10  0.90
 E9  0.096  1.80
 K12  0.01
 K18  0.03
 K21  0.02  0.06
 K22  0.08  0.20  0.25  0.056  0.58
 K25  0.03
 K31  0.20  0.80
 K32  0.03  0.05  0.316
 K35  0.018
 K36  0.03  0.05  0.01
 K26
 D1  0.01
 D3  0.04  0.06  0.025
 色泽  亮金色至金铜色  金铜色  亮铜色  紫褐色  金银色  暗红棕色
                       表5-续
实施例  62  63  64  65  66  67
染料                   (染料量，克)
 E2  0.01  0.60  1.00  0.20  0.80  0.60
 E10  2.00  1.90
 E3  0.05
 E8  1.00
 E9  1.00  0.70
 K12  1.10
 K13  0.07  0.80
 K16  1.00
 K17  1.10
 K18  1.25
 K21  0.40  0.28
 K22  0.08  0.50
 K25  0.80
 K31  0.80
 K32  0.03
 K33  0.75
 K36  0.03
 D1  0.25
 D3  0.15
 色泽  黑褐色  橙色  蓝紫色  蓝红色  粉红色  枣红色
                      表5-续
实施例  68  69  70  71
染料                   (染料量，克)
 E2  0.01  0.01  0.05  0.06
 E3  1.40  4.50
 E5  0.25
 E6  0.10
 E8  0.80  0.50  0.01
 E9  2.70
 K12  0.60
 K13  0.20  0.80
 K14  0.25
 K16  0.01
 K18  1.25
 K19  0.80
 K21  0.30  0.28
 K22  5.00
 K25  0.40
 K23  0.60
 K31  1.10
 K32  0.33
 K34  0.20
 K36  0.19
 D2  0.50
 色泽  黑色  紫红色  橙红色  暖黄色
                         表6-头发染色剂
实施例  72  73  74  75  76  77
染料                     (染料量，克)
 E1  0.10  0.20  0.01  2.00  0.50  0.70
 E4  1.60
 E8  0.25  0.80  0.20
 E9  3.20  1.71  0.02  1.80
 K13  0.23  0.10  1.30
 K14  0.20
 K16  0.015
 K21  0.40  0.80  0.02
 K22  0.08  0.25  1.80  4.50
 K23  0.20  0.03
 K31  1.05  0.135  0.02  0.25  0.80
 K25  0.55
 K26  0.03
 K19  1.70
 K36  0.27
 D2  0.01
 色泽  暗褐色  巧克力褐色  金银色  橙色  蓝紫色  紫红色
除非另有说明，本专利申请中的所有百分比都以重量计。

Claims (13)

1、通式(I)的(对氨基羟基苯基)丙烯酰胺衍生物或其生理耐受的水溶性盐
Figure A0181152300021
其中
R1代表氢、卤原子、C1-C4-烷基、C1-C4-羟基烷基或C1-C4-烷氧基；
R2和R3各自独立地代表氢或C1-C6-烷基；
R4和R5各自独立地代表氢、C1-C2-烷氧基、C1-C6-烷基、不饱和C3-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、C2-C4-氨基烷基、C2-C4-二甲基氨基烷基、C2-C4-乙酰基氨基烷基、C2-C4-甲氧基烷基、C2-C4-乙氧基烷基、C1-C4-氰基烷基、C1-C4-羧基烷基、C1-C4-氨基羰基烷基、吡啶基甲基、糠基、噻吩基甲基、氢化糠基、取代的吡啶基、式(II)的基团
Figure A0181152300022
式(III)的基团
或式(IV)的基团
Figure A0181152300024
或者R4和R5与氮原子一起形成下式的环
Figure A0181152300031
R6代表氢、羧基或氨基羰基；
R7和R8各自单独地代表氢、羟基、氨基羰基、甲硫基甲基、苯基取代的或羟基取代的苯基或下式的基团
Figure A0181152300032
R9、R10、R11、R12和R13各自独立地代表氢、卤原子、氰基、羟基、C1-C4-烷氧基、C1-C4-羟基烷氧基、C1-C6-烷基、C1-C4-烷基硫醚基、巯基、硝基、氨基、烷基氨基、C1-C4-羟基烷基氨基、二烷基氨基、二(C1-C4-羟基烷基)氨基、(C3-C4-二羟基烷基)氨基、(C1-C4-羟基烷基)-C1-C4-烷基氨基、三氟甲基、-C(O)H基团、-C(O)CH3-基团、-C(O)CF3基团、-Si(CH3)3基团、C1-C4-羟基烷基或C3-C4-二羟基烷基、或者两个相邻的R9-R13基团形成-O-CH2-O-桥；
R14代表C1-C4-烷基、苄基或C2-C4-羟基烷基；
R15代表氢或C1-C6-烷基；
R16代表氢、羟基、羧基、氨基羰基或羟基甲基；和
R17代表氢或C1-C6-烷基。
2、如权利要求1的对氨基苯酚衍生物，其特征在于式(I)中R1、R2和R3基团中的一个、几个或所有代表氢。
3、如权利要求1或2的对氨基苯酚衍生物，其特征在于式(I)中R4代表C1-C2-烷基、甲氧基或C2-C4-羟基烷基，并且R5代表C2-C4-羟基烷基。
4、如权利要求1或2的对氨基苯酚衍生物，其特征在于式(I)中R4和R5各自独立地代表氢、C1-C4-烷基、不饱和C1-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、糠基、式(III)的经取代的苯基或式(IV)的经取代的吡唑基。
5、如权利要求1、2或4的对氨基苯酚衍生物，其特征在于式(I)中R4代表氢并且R5代表C1-C4-烷基、不饱和C3-C6-烷基、C2-C4-羟基烷基、C3-C4-二羟基烷基、糠基、式(III)的经取代的苯基或式(IV)的经取代的吡唑基。
6、如权利要求1-5任一的对氨基苯酚衍生物，其特征在于，它选自3-(5-氨基-2-羟基苯基)-N-乙基丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-乙基丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(4-羟基苯基)丙烯酰胺、3-(5-氨基-2-羟基苯基)-N-(4-氨基苯基)丙烯酰胺、3-(2-氨基-5-羟基苯基)-N-(4-氨基苯基)丙烯酰胺、N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(5-氨基-2-羟基苯基)丙烯酰胺和N-[4-氨基-2-(2-羟基乙基)-2H-吡唑-3-基]-3-(2-氨基-5-羟基苯基)丙烯酰胺及其生理耐受盐。
7、以显色剂-成色剂组合为基础用于氧化染色角蛋白纤维的试剂，其特征在于它含有至少一种如权利要求1-6之一项的式(I)对氨基苯酚衍生物作为显色剂。
8、如权利要求7的试剂，其特征在于它含有量为0.005-20重量％的式(I)对氨基苯酚衍生物。
9、如权利要求7或8的试剂，其特征在于所述成色剂选自N-(3-二甲基氨基苯基)脲、2，6-二氨基吡啶、2-氨基-4-[(2-羟基乙基)氨基]茴香醚、2，4-二氨基-1-氟-5-甲基苯、2，4-二氨基-1-甲氧基-5-甲基苯、2，4-二氨基-1-乙氧基-5-甲基苯、2，4-二氨基-1-(2-羟基乙氧基)-5-甲基苯、2，4-二[(2-羟基乙基)氨基]-1，5-二甲氧基苯、2，3-二氨基-6-甲氧基吡啶、3-氨基-6-甲氧基-2-(甲基氨基)吡啶、2，6-二氨基-3，5-二甲氧基吡啶、3，5-二氨基-2，6-二甲氧基吡啶、1，3-二氨基苯、2，4-二氨基-1-(2-羟基乙氧基)苯、1，3-二氨基-4-(2，3-二羟基丙氧基)苯、1，3-二氨基-4-(3-羟基丙氧基)苯、1，3-二氨基-4-(2-甲氧基乙氧基)苯、2，4-二氨基-1，5-二(2-羟基乙氧基)苯、1-(2-氨基乙氧基)-2，4-二氨基苯、2-氨基-1-(2-羟基乙氧基)-4-甲基氨基苯、2，4-二氨基苯氧基乙酸、3-[二(2-羟基乙基)氨基]苯胺、4-氨基-2-二[(2-羟基乙基)氨基]-1-乙氧基苯、5-甲基-2-(1-甲基乙基)苯酚、3-[(2-羟基乙基)氨基]苯胺、3-[(2-氨基乙基)氨基]苯胺、1，3-二(2，4-二氨基苯氧基)丙烷、二(2，4-二氨基苯氧基)甲烷、1，3-二氨基-2，4-二甲氧基苯、2，6-二-(2-羟基乙基)氨基甲苯、4-羟基吲哚、3-二甲基氨基苯酚、3-二乙基氨基苯酚、5-氨基-2-甲基苯酚、5-氨基-4-氟-2-甲基苯酚、5-氨基-4-甲氧基-2-甲基苯酚、5-氨基-4-乙氧基-2-甲基苯酚、3-氨基-2，4-二氯苯酚、5-氨基-2，4-二氯苯酚、3-氨基-2-甲基苯酚、3-氨基-2-氯-6-甲基苯酚、3-氨基苯酚、2-[(3-羟基苯基)氨基]乙酰胺、5-[(2-羟基乙基)氨基]-4-甲氧基-2-甲基苯酚、5-[(2-羟基乙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]苯酚、3-[(2-甲氧基乙基)氨基]苯酚、5-氨基-2-乙基苯酚、5-氨基-2-甲氧基苯酚、2-(4-氨基-2-羟基苯氧基)乙醇、5-[(3-羟基丙基)氨基]-2-甲基苯酚、3-[(2，3-二羟基丙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]-2-甲基苯酚、2-氨基-3-羟基吡啶、2，6-二羟基-3，4-二甲基吡啶、5-氨基-4-氯-2-甲基苯酚、1-萘酚、2-甲基-1-萘酚、1，5-二羟基萘、1，7-二羟基萘、2，3-二羟基萘、2，7-二羟基萘、乙酸2-甲基-1-萘酯、1，3-二羟基苯、1-氯-2，4-二羟基苯、2-氯-1，3-二羟基苯、1，2-二氯-3，5-二羟基-4-甲基苯、1，5-二氯-2，4-二羟基苯、1，3-二羟基-2-甲基苯、3，4-亚甲基二氧基苯酚、3，4-亚甲基二氧基苯胺、5-[(2-羟基乙基)氨基]-1，3-苯并间二氧杂环戊烯、6-溴-1-羟基-3，4-亚甲基二氧基苯、3，4-二氨基苯甲酸、3，4-二氢-6-羟基-1，4(2H)苯并噁嗪、6-氨基-3，4-二氢-1，4(2H)苯并噁嗪、3-甲基-1-苯基-5-吡唑啉酮、5，6-二羟基吲哚、5，6-二羟基二氢吲哚、5-羟基吲哚、6-羟基吲哚、7-羟基吲哚和2，3-二氢吲哚二酮。
10、如权利要求7-9之一的试剂，其特征在于除了式(I)的化合物之外，它含有选自以下的其它已知化合物：1，4-二氨基苯、1，4-二氨基-2-甲基苯、1，4-二氨基-2，6-二甲基苯、1，4-二氨基-3，5-二乙基苯、1，4-二氨基-2，5-二甲基苯、1，4-二氨基-2，3-二甲基苯、2-氯-1，4-二氨基苯、1，4-二氨基-2-(噻吩-2-基)苯、1，4-二氨基-2-(噻吩-3-基)苯、1，4-二氨基-2-(吡啶-3-基)苯、2，5-二氨基联苯、1，4-二氨基-2-甲氧基甲基苯、1，4-二氨基-2-氨基甲基苯、1，4-二氨基-2-羟基甲基苯、1，4-二氨基-2-(2-羟基乙氧基)苯、2-[2-(乙酰基氨基)乙氧基]-1，4-二氨基苯、4-苯基氨基苯胺、4-二甲基氨基苯胺、4-二乙基氨基苯胺、4-二丙基氨基苯胺、4-[乙基(2-羟基乙基)氨基]苯胺、4-[二(2-羟基乙基)氨基]苯胺、4-[二(2-羟基乙基)氨基]-2-甲基苯胺、4-[(2-甲氧基乙基)氨基]苯胺、4-[(3-羟基丙基)氨基]苯胺、4-[(2，3-二羟基丙基)氨基]苯胺、1，4-二氨基-2-(1-羟基乙基)苯、1，4-二氨基-2-(2-羟基乙基)苯、1，4-二氨基-2-(1-甲基乙基)苯、1，3-二-[(4-氨基苯基)(2-羟基乙基)氨基]-2-丙醇、1，4-二[(4-氨基苯基)氨基]丁烷、1，8-二-(2，5-二氨基苯氧基)-3，6-二氧杂辛烷、4-氨基苯酚、4-氨基-3-甲基苯酚、4-氨基-3-(羟基甲基)苯酚、4-氨基-3-氟苯酚、4-甲基氨基苯酚、4-氨基-2-(氨基甲基)苯酚、4-氨基-2-(羟基甲基)苯酚、4-氨基-2-氟苯酚、4-氨基-2-[(2-羟基乙基)氨基]-甲基苯酚、4-氨基-2-甲基苯酚、4-氨基-2-(甲氧基甲基)苯酚、4-氨基-2-(2-羟基乙基)苯酚、5-氨基水杨酸、2，5-二氨基吡啶、2，4，5，6-四氨基嘧啶、2，5，6-三氨基-4-(1H)-嘧啶酮、4，5-二氨基-1-(2-羟基乙基)-1H-吡唑、4，5-二氨基-1-(1-甲基乙基)-1H-吡唑、4，5-二氨基-1-[(4-甲基苯基)甲基]-1H-吡唑、1-[(4-氯苯基)甲基]-4，5-二氨基-1H-吡唑、4，5-二氨基-1-甲基-1H-吡啶、2-氨基苯酚、2-氨基-6-甲基苯酚、2-氨基-5-甲基苯酚和1，2，4-三羟基苯。
11、如权利要求7-10之一的试剂，其特征在于以染色剂的总量为基础，它含有的显色剂和成色剂的量各自为0.005-20重量％。
12、如权利要求7-11之一的试剂，其特征在于它另外含有至少一种直接染料。
13、如权利要求7-12之一的试剂，其特征在于它是头发染色剂。
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CN1205179C (zh) 2005-06-08
DE10115994A1 (de) 2002-10-10
ES2215111T3 (es) 2004-10-01
EP1286953B1 (de) 2004-02-18
BR0111197A (pt) 2003-04-08
ATE259780T1 (de) 2004-03-15
US7070626B2 (en) 2006-07-04
JP2004518765A (ja) 2004-06-24
CA2443304A1 (en) 2002-10-10
MXPA03008736A (es) 2003-12-12
HK1054738A1 (en) 2003-12-12
WO2002079144A1 (de) 2002-10-10
DE50101515D1 (de) 2004-03-25
AU2002221707B2 (en) 2006-04-27
EP1286953A1 (de) 2003-03-05

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