CN1282317A - 新型对氨基苯酚衍生物及其用途 - Google Patents
新型对氨基苯酚衍生物及其用途 Download PDFInfo
- Publication number
- CN1282317A CN1282317A CN98812299.5A CN98812299A CN1282317A CN 1282317 A CN1282317 A CN 1282317A CN 98812299 A CN98812299 A CN 98812299A CN 1282317 A CN1282317 A CN 1282317A
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- China
- Prior art keywords
- amino
- methyl
- phenol
- aminophenyl
- reagent composition
- Prior art date
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- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title description 5
- -1 sulfoxy Chemical group 0.000 claims abstract description 61
- 230000003647 oxidation Effects 0.000 claims abstract description 27
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 27
- 239000003086 colorant Substances 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005864 Sulphur Substances 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 37
- 239000003153 chemical reaction reagent Substances 0.000 claims description 33
- 239000000975 dye Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 20
- 238000004043 dyeing Methods 0.000 claims description 14
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000004782 1-naphthols Chemical class 0.000 claims description 6
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 6
- XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 claims description 6
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 claims description 6
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 claims description 6
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 6
- WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 claims description 6
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 claims description 5
- XWZVTZRAADNQRT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C(OCO2)C2=C1 XWZVTZRAADNQRT-UHFFFAOYSA-N 0.000 claims description 5
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 claims description 5
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- RYXPCUFPAXUVMV-UHFFFAOYSA-N OCCC1=NNC=C1.NC1=CC=C(C=C1N)C=CC1=CC=CC=C1 Chemical class OCCC1=NNC=C1.NC1=CC=C(C=C1N)C=CC1=CC=CC=C1 RYXPCUFPAXUVMV-UHFFFAOYSA-N 0.000 claims description 5
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- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 claims description 4
- 239000008365 aqueous carrier Substances 0.000 claims description 4
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
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- CHLOVPDKABYEDC-UHFFFAOYSA-N [6-(decylamino)-1h-indol-4-yl]methanol Chemical compound CCCCCCCCCCNC1=CC(CO)=C2C=CNC2=C1 CHLOVPDKABYEDC-UHFFFAOYSA-N 0.000 description 5
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- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 4
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
本发明涉及通式(Ⅰ)的化合物和其生理上可接受的盐,其中A、B、C和D相互独立地是-OH或-NHR基团,R是氢原子或C1-4-烷基,其附加条件是A或B和C或D是羟基,X是氧、硫、亚硫酰基或硫酰基和R1和R2相互独立地代表氢、氟、氯、C1-4-烷基或羟烷基或C2-4-二羟烷基,优选C2-二羟烷基。它们特别适合用作氧化着色剂中的显色剂组分。
Description
本发明涉及新的对氨基苯酚衍生物、它们在染色角蛋白纤维中的应用以及含有这些化合物的着色剂。
由于它们有鲜明的色彩和高的牢固度性质,所谓的氧化着色剂在角蛋白纤维的染色中起着重要的作用,特别是对人类头发的染色。氧化着色剂含氧化染料前体,即所谓显色剂组分和成色剂组分(kupplekomponente)。显色剂组分在氧化剂或大气氧的存在下互相形成真正的染料,或与一种或多种成色剂组分进行偶合形成真正的染料。
好的氧化染料前体首先应能满足下列要求:在氧化偶合反应中它们必须形成有足够强度和牢固度要求的色调;另外,它们必须易于被纤维吸收,尤其在人类头发的情况下在损坏和新生的毛发间没有明显的差别(匀染行为);它们必须是耐光、热和化学还原剂(例如,电烫液)的作用的;最后,如用于染头发,它们不应过度玷污头皮,并且首先应在毒理学和皮肤学上是安全的。
通常所用的显色剂组分是在邻或对位上含另一取代或未取代的羟基或氨基的芳香族伯胺、二氨基吡啶衍生物、杂环腙、4-氨基吡唑啉酮衍生物和2,4,5,6-四氨基嘧啶以及它们的衍生物。
特别有代表性的是例如对苯二胺、对甲苯二胺、2,4,5,6-四氨基嘧啶、对氨基苯酚、N,N-双(2-羟乙基)对苯二胺、2-(2,5-二氨基苯基)乙醇、2-(2,5-二氨基苯氧基)乙醇、1-苯基-3-羧酰氨基-4-氨基-5-吡唑啉酮、4-氨基-3-甲基苯酚、2-氨基甲基-4-氨基苯酚、2-羟基-4,5,6-三氨基-4-嘧啶、2,4-二羟基-5,6-二氨基嘧啶、2,5,6-三氨基-4-羟基嘧啶和1,3-N,N’-双(2’-羟基乙基)-N,N’-双(4’-氨基苯基)-二氨基-2-丙醇。
成色剂组分一般是间苯二胺衍生物、萘酚、间苯二酚和间苯二酚衍生物、吡唑啉酮和间氨基苯酚。特别适合的成色剂组分是1-萘酚、1,5-、2,7-和1,7-二羟萘、5-氨基-2-甲基苯酚、间氨基苯酚、间苯二酚、间苯二酚单甲醚、间苯二胺、1-苯基-3-甲基-5-吡唑啉酮、2,4-二氯-3-氨基苯酚、1,3-双(2,4-二氨基苯氧基)丙烷、2-氯间苯二酚、4-氯间苯二酚、2-氯-6-甲基-3-氨基苯酚、2-氨基-4-羟基吡啶、2-甲基间苯二酚、5-甲基间苯二酚和2-甲基-4-氯-5-氨基苯酚。
一般说来,单独使用显色剂组分或使用特别的成色剂组分/显色剂组分的组合是不能在头发上得到天然色调的。因此,在实践中通常使用各种显色剂组分和成色剂组分的组合。因此对新改进的染料组分存在着不断的需求。
所以,本发明的任务是提供能够符合对氧化染料前体的要求至一特殊程度的新的显色剂组分。
现已发现,某些至今未知的对氨基苯酚衍生物能满足显色剂组分所希望满足的要求至一特别高的程度。因此,使用这些显色剂组分和大部分已知的成色剂组分得到了具有极好耐光和耐洗涤牢度的鲜艳色调,更特别是在棕色和红色范围的色调。
-A、B、C和D相互独立地是-OH或-NHR基团,R是氢原子或C1 -4-烷基,其附加条件是A或B和C或D是羟基,
-X是氧、硫、亚硫酰基(Sulfoxy)或硫酰基(Sulfoxyl)和
-R1和R2相互独立地代表氢、氟、氯、C1-4-烷基或羟烷基或C2-4-二羟烷基,优选C2-二羟烷基。
这些化合物可用已知的有机合成方法来制备。其细节可见于下列的合成实施例中。
因为所有的本发明化合物是氨基化合物,所以可以常规方式由它们来制备已知的酸加成盐。因此,本说明书陈述的并因此要求保护的范围涉及游离形式的式(Ⅰ)的对氨基苯酚衍生物和其水溶性、生理上可接受盐。这些盐的实例是盐酸盐、氢溴酸盐、硫酸盐、磷酸盐、乙酸盐、丙酸盐、柠檬酸盐和乳酸盐。
本发明特别适合的是其中基团X是氧原子或硫原子的式(Ⅰ)的对氨基苯酚衍生物。特别有利的是基团X是氧。
同样根据本发明优选其中不表示-OH基团的那些基团A、B、C和D是-NH2-基团的式(Ⅰ)的对氨基苯酚衍生物。
此外,证明在式(Ⅰ)的对氨基苯酚衍生物中特别适合的基团R1和R2是氢。
最后特别适合本发明的是那些其中取代基R1和R2相同、A和C相同以及B和D是相同的式(Ⅰ)的对氨基苯酚衍生物。
本发明中特别适合的化合物是4-氨基-2-(((5-氨基-2-羟基苯基)甲氧基)甲基)苯酚。
本发明的第二方面涉及前述对氨基苯酚衍生物作为氧化着色剂中显色剂组分的应用。
最后,本发明的第三方面涉及在含水载体中含有成色剂组分和显色剂组分的染色角蛋白纤维的氧化着色剂,其包含上述的对氨基苯酚衍生物之一作为显色剂组分。
在本发明上下文中,角蛋白纤维包括毛皮、羊毛、羽毛以及特别是人类的头发。虽然本发明的氧化着色剂特别适合于角蛋白纤维的染色,但这并不限制它们在其它领域中的应用,特别是在彩色照相术中的应用。
本发明的氧化着色剂含式(Ⅰ)的显色剂组分以及成色剂组分,需要时可含其它显色剂组分和成色剂组分。
本发明优选的其它显色剂组分是对苯二胺、对甲苯二胺、对氨基苯酚、2-(2,5-二氨基苯基)乙醇、N,N-双-(2-羟乙基)-对-苯二胺、1-苯基-3-羧酰氨基-4-氨基-5-吡唑啉酮、4-氨基-3-甲基苯酚、4-氨基-3-氟苯酚、2-氨甲基-4-氨基苯酚、2,4,5,6-四氨基嘧啶、2-羟基-4,5,6-三氨基嘧啶、4-羟基-2,5,6-三氨基嘧啶、2,4-二羟基-5,6-二氨基嘧啶、2-二甲氨基-4,5,6-三氨基嘧啶、2-羟乙基氨甲基-4-氨基苯酚以及4,4’-二氨基二苯胺。2-羟甲基-4-氨基苯酚、双(2-羟基-5-氨苯基)甲烷、1,4-双(4-氨苯基)二氮杂环庚烷、1,3-N,N'-双(2'-羟乙基)-N,N'-双(4'-氨基苯基)-二氨基-1,3-丙烷-2-醇、以及根据EP 0 740 931或WO 94/08970的4,5-二氨基吡唑衍生物,诸如4,5-二氨基-1-(2’-羟乙基)吡唑是优选与本发明显色剂组分组合的显色剂组分。
最特别优选的其它的显色剂组分是对苯二胺、2,4,5,6-四氨基嘧啶、4,5-二氨基-1-(2’-羟乙基)吡唑、N,N-双-(2-羟乙基)-对苯二胺、双(2-羟基-5-氨苯基)甲烷、2-(2,5-二氨基苯基)乙醇、3-甲基-4-氨基苯酚、4-羟基-2,5,6-三氨基嘧啶、2-氨甲基-4-氨基苯酚和对甲苯二胺。
本发明优选的成色剂组分是1-萘酚、1,2,3-苯三酚、1,5-、2,7-、1,7-二羟基萘、邻氨基苯酚、5-氨基-2-甲基苯酚、间氨基苯酚、间苯二酚、间苯二酚单甲醚、1-苯基-3-甲基-5-吡唑啉酮、2,4-二氯-3-氨基苯酚、1,3-双(2,4-二氨基苯氧基)丙烷、4-氯间苯二酚、2-氯-6-甲基-3-氨基苯酚、2-甲基间苯二酚、5-甲基间苯二酚、2,5-二甲基间苯二酚、2,6-二羟基吡啶、2,6-二氨基吡啶、2-氨基-3-羟基吡啶、2,6-二羟基-3,4-二氨基吡啶、2-甲基-4-氯-5-氨基苯酚、6-甲基-1,2,3,4-四氢喹喔啉、3-氨基-2-甲氨基-6-甲氧基吡啶、4-氨基-2-羟基甲苯、2,6-双(2-羟乙基氨基)甲苯、3,4-亚甲基二氧基苯酚、3,4-亚甲基二氧基苯胺、2,4-二氨基苯氧基乙醇、2-氨基-4-(2-羟乙基氨基)苯甲醚和2,6-二甲基-3-氨基苯酚。
特别优选的成色剂组分是1-萘酚、间氨基苯酚、5-氨基-2-甲基苯酚、3-甲基磺酰基氨基-2-甲基苯胺、3-氨基-2-甲氨基-6-甲氧基吡啶、2,6-二甲基-3-氨基苯酚、2,4-二氨基苯氧基乙醇、2,7-二羟基萘、6-甲基-1,2,3,4-四氢喹喔啉、1,7-二羟基萘、2-甲基-4-氯-5-氨基苯酚、3,4-亚甲基二氧基苯胺、2-甲基间苯二酚、4-氯-间苯二酚、3,4-亚甲基二氧基苯酚、2-氨基-3-羟基吡啶和2-氯-6-甲基-3-氨基苯酚。
这些其它的显色剂组分和成色剂组分常以其游离形式使用。但若它们含氨基,可优选使用其盐的形式,特别是盐酸盐和硫酸盐形式。
本发明的毛发着色剂含显色剂组分和成色剂组分的量优选各为0.005-20wt%、更优选0.1-5wt%,分别基于氧化着色剂总量计算。显色剂组分和成色剂组分一般以基本上相互等摩尔的量使用。虽然使用等摩尔比的显色剂组分和成色剂组分被证明是有利的,但使用某一过量的氧化染料前体组分是无害处的,这样显色剂组分和成色剂组分的摩尔比可以为1∶0.5-1∶3,更特别是1∶1-1∶2。
在优选的实施方案中,为了进一步改善色调,本发明的染发剂除氧化染料前体外还包括常规的直接染料。直接染料通常是硝基苯二胺、硝基氨基苯酚、偶氮染料、蒽醌或靛酚。优选的直接染料是国际名或商品名如下的化合物:HC黄2、HC黄4、HC黄6、碱性黄57、分散橙3、HC红3、HC红BN、碱性红76、HC兰2、分散兰3、碱性兰99、HC紫1、分散紫1、分散紫4、分散黑9、碱性棕16和碱性棕17,以及4-氨基-2-硝基二苯胺-2’-羧酸、6-硝基-1,2,3,4-四氢喹喔啉、羟乙基-2-硝基甲苯胺、苦氨酸、2-氨基-6-氯-4-硝基苯酚和4-N-乙基-1,4-双(2’-羟乙基氨基)-2-硝基苯盐酸盐。根据这一实施方案的本发明着色剂含直接染料的量最好是0.01-20wt%,基于着色剂总量计算。
本发明的着色剂也可含天然染料,诸如散沫花红、散沫花灰、散沫花黑、春黄菊花、檀香木、黑茶、黑桤木皮、鼠尾草、苏木、茜草根、儿茶、sedre和紫草根。
可在本发明着色剂中使用的其他染料组分是吲哚和二氢吲哚和其生理上可接受盐。优选的例子是5,6-二羟吲哚、N-甲基-5,6-二羟吲哚、N-乙基-5,6-二羟吲哚、N-丙基-5,6-二羟吲哚、N-丁基-5,6-二羟吲哚、6-羟基吲哚、6-氨基吲哚、4-氨基吲哚。优选的还有5,6-二羟基二氢吲哚、N-甲基-5,6-二羟基二氢吲哚、N-乙基-5,6-二羟基二氢吲哚、N-丙基-5,6-二羟基二氢吲哚、N-丁基-5,6-二羟基二氢吲哚、6-羟基二氢吲哚、6-氨基二氢吲哚和4-氨基二氢吲哚。
氧化染料前体或直接染料不必分别是单一的化合物。相反,由于生产单个染料的方法而在本发明的毛发着色剂中可存在少量的其他组分,只要这些其他组分对染色结果不起负作用,或因其他原因而必须被排除,例如有毒性。
就本发明的毛发着色剂和染色配方中适合使用的染料而言,也请参考Ch.Zviak的著作,头发护理科学(The Science of Hair Care),Chap.7(pp248-250;直接染料)和Chap.8(pp264-267;氧化染料前体),刊登在“皮肤学”(“Dermatology”)第7卷(Ed.:Ch.Culnan和H.Maibach),Marcel Dekker Inc_New York/Basel,1986,并参考“欧洲化妆品原料目录”(“Europaeische Inventar der Kosmetik-Rohstoffe”),由Europaeischen Gemeinschaft出版,Bundesverband DeutscherIndustrie-und Handelsunternehmen fuer Arzneimittel,Reformwarenund Koerperpflegemittel e.V_Mannheim供应光盘。
在生产本发明的着色剂时,是把氧化染料前体掺入适合的含水载体中。用于染发目的这种载体是,例如乳膏、乳状液、凝胶体或者甚至是含表面活性剂的发泡溶液,例如香波,泡沫气溶胶,或适合于用在头发上的其它配方。
本发明的着色剂也可含这类配方中任何已知的活性物质,添加剂和助剂。在许多情况中,着色剂至少含一种表面活性剂,阴离子和两性离子的、两性的、非离子的和阳离子表面活性剂在原则上都是适合的。但在许多情况中,发现从阴离子、两性离子或非离子表面活性剂中选择表面活性剂是有利的。
适合于本发明的配方的阴离子表面活性剂是适合用于人体上的任何阴离子表面活性物质。这类物质的特征是有赋予水溶性的阴离子基团,诸如羧酸根、磺酸根、硫酸根或磷酸根基团,和一个含约10-22个碳原子的亲油烷基。另外,在分子中也可存在乙二醇或聚乙二醇醚基、酯、醚和酰胺基团以及羟基。下面是适合的阴离子表面活性剂的实例,在每种情况下是钠、钾和铵盐形式和在烷醇基中含2或3个碳原子的一、二和三烷醇铵盐形式:
-含10-22个碳原子的直链脂肪酸(皂),
-相应于式R-O-(CH2-CH2O)x-CH2-COOH(其中R是含10-22个碳原子的直链烷基,X=0或1-16)的醚羧酸,
-酰基中含10-18个碳原子的酰基肌氨酸化合物,
-酰基中含10-18个碳原子的酰基牛磺酸化合物,
-酰基中含10-18个碳原子的酰基羟乙磺酸盐,
-烷基中含8-18个碳原子的磺基琥珀酸的单-和二烷基酯和烷基中含8-18个碳原子和含1-6个氧乙基的磺基琥珀酸单烷基聚氧乙基酯,
-含12-18个碳原子的直链烷磺酸盐,
-含12-18个碳原子的直链α-烯烃磺酸盐,
-含12-18个碳原子的脂肪酸的α-磺基脂肪酸甲酯,
-相应于式R-O-(CH2-CH2O)x-SO3H(其中R最好是含10-18个碳原子的直链烷基;X=0或1-12)的烷基硫酸盐和烷基聚乙二醇醚硫酸盐,
-根据DE-A-37 25 030的表面活性羟基磺酸盐混合物,
-根据DE-A-37 23 354的硫酸化羟烷基聚乙烯-和/或羟基亚烷基丙二醇醚,
-根据DE-A-39 26 344的含12-24个碳原子和1-6个双键的不饱和脂肪酸的磺酸盐,
-醇为2-15个左右环氧乙烷和/或环氧丙烷分子与含8-22个碳原子的脂肪醇的加合产物的酒石酸和柠檬酸的酯。
优选的阴离子表面活性剂是烷基中含10-18个碳原子和分子中最多含12个乙二醇醚基的烷基硫酸盐、烷基聚乙二醇醚硫酸盐和醚羧酸,特别是饱和的、更特别是不饱和的C8-C22羧酸(诸如油酸、硬脂酸、异硬脂酸和棕榈酸)的盐。
两性离子表面活性剂是分子中含至少一个季铵基和至少一个-COO-或-SO3 -基团的表面活性剂。特别适合的两性离子表面活性剂是所谓的甜菜碱型表面活性剂,诸如N-烷基-N,N-二甲基铵甘氨酸盐,例如椰子烷基二甲基铵甘氨酸盐,N-酰基氨基丙基-N,N-二甲基铵甘氨酸盐,例如椰子酰基氨基丙基二甲基铵甘氨酸盐,以及烷基或酰基中分别含8-18个碳原子的2-烷基-3-羧甲基-3-羟乙基咪唑啉以及椰子酰基氨基乙基羟乙基羧甲基甘氨酸盐。一个优选的两性离子表面活性剂是CTFA名为Cocamidopropyl Betaine的脂肪酸酰胺衍生物。
两性表面活性物质是分子中除C8-18烷基或酰基外还含有至少一个游离氨基和至少一个-COOH或-SO3H基并能形成内盐的表面活性化合物。适合的两性表面活性剂的实例是在烷基中分别含8-18个左右碳原子的N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸。特别优选的两性表面活性剂是N-椰子烷基氨基丙酸盐、椰子酰基氨基乙基氨基丙酸盐和C12-18酰基肌氨酸。
非离子表面活性剂含有,例如多元醇基,聚亚烷基二醇醚基或多元醇基和聚乙二醇醚基的组合作为亲水基团。这样的化合物的实例是:
-2-30摩尔环氧乙烷和/或0-5摩尔环氧丙烷在含8-22个碳原子的直链脂肪醇、含12-22个碳原子的脂肪酸和在烷基上含8-15个碳原子的烷基苯酚上的加合产物,
-1-30摩尔的环氧乙烷在甘油上的加合产物的C12-22脂肪酸单酯和二酯,
-C8-22烷基单-和低聚糖苷和它们的乙氧基化同类物,
-5-60摩尔环氧乙烷在蓖麻油和氢化蓖麻油上的加合产物,
-环氧乙烷在脱水山梨醇脂肪酸酯上的加合产物,
-环氧乙烷在脂肪酸烷醇酰胺上的加合产物。
适合于在本发明毛发处理配方中使用的阳离子表面活性剂的实例特别是季铵化合物。优选的季铵化合物是卤化铵类,诸如烷基三甲基氯化铵、二烷基二甲基氯化铵和三烷基甲基氯化铵,例如十六烷基三甲基氯化铵、硬脂基三甲基氯化铵、二硬脂基二甲基氯化铵、月桂基二甲基氯化铵、月桂基二甲基苄基氯化铵和三鲸蜡基甲基氯化铵。适合本发明使用的其它阳离子表面活性剂是季铵化的蛋白质水解产物。
按本发明适合使用的还有阳离子硅油,诸如市场供应产品Q2-7224(生产厂商:Dow Corning,一种稳定化的三甲基甲硅烷基amodimethicon),Dow Corning 929 Emulsion(含一羟氨基改性的聚硅氧烷,也称作Amodimethicone),SM-2059(生产厂商:General Electric),SLM-55067(生产厂商:Wacker)和Abil_-Quat 3270和3272(生产厂商:TH.Goldschmidt;二季化聚二甲基硅氧烷,Quaternium-80)。
烷基酰氨基胺,特别是脂肪酸酰氨基胺,诸如作为Tego Amid_S 18得到的硬脂酰氨基丙基二甲基胺,不仅由于它们的调节效果好,而且特别由于它们能良好生物降解而表现突出。
季铵酯化合物,即所谓的“Esterquats”,诸如以商名Stepantex_销售的甲基羟烷基二烷酰氧基烷基铵甲硫酸盐以及以商品名Dehyquart_销售的产品如Dehyquart AU-46,也是可迅速生物降解的。
适合于用作阳离子表面活性剂的季糖衍生物的一个实例是市场供应的产品Glucquat_100(INCI名:Lauryl Methyl Gluceth-10Hydroxypropyl Dimonium Chloride)。
用作表面活性剂的含烷基的化合物可以是单一的化合物。但一般优选这些化合物是从天然植物或动物原料生产的,所以得到的是根据特定的原料而有不同烷基链长的混合物。
在表面活性剂是环氧乙烷和/或环氧丙烷与脂肪醇的加合产物或这些加合产物的衍生物的情况下,可以是具有“正常”同系物分布的产物和具有窄同系物分布的产物。具有“正常”同系物分布的产物是用碱金属、碱金属氢氧化物或碱金属醇盐作为催化剂在脂肪醇和烯化氧的反应中得到的同系物混合物。对比之下,窄同系物分布是当例如用水滑石、醚羧酸的碱土金属盐、碱土金属的氧化物、氢氧化物或醇盐作为催化剂得到的。使用具有窄同系物分布的产物是有利的。
其它的活性物质、助剂和添加剂是,例如,
-非离子聚合物,诸如乙烯基吡咯烷酮/丙烯酸乙烯酯共聚物、聚乙烯吡咯烷酮和乙烯基吡咯烷酮/乙酸乙烯酯共聚物、以及聚硅氧烷,
-阳离子聚合物,诸如季铵化纤维素醚、含季基的聚硅氧烷、二甲基二烯丙基氯化铵聚合物、丙烯酰胺/二甲基二烯丙基氯化铵共聚合物、用硫酸二乙酯季铵化的二甲基氨乙基甲基丙烯酸酯/乙烯基吡咯烷酮共聚物,乙烯基吡咯烷酮/咪唑啉鎓甲氯化物共聚物和季铵化聚乙烯醇,
-两性离子和两性聚合物,诸如丙烯酰氨基丙基三甲基氯化铵/丙烯酸酯共聚物和辛基丙烯酰胺/甲基丙烯酸甲酯/甲基丙烯酸叔丁基氨乙基酯/甲基丙烯酸(2-羟丙基)酯共聚物,
-阴离子聚合物,诸如聚丙烯酸、交联聚丙烯酸、乙酸乙烯酯/巴豆酸共聚物、乙烯基吡咯烷酮/丙烯酸乙烯酯共聚物、乙酸乙烯酯/马来酸丁酯/丙烯酸异冰片酯共聚物、甲基乙烯基醚/马来酸酐共聚物和丙烯酸/丙烯酸乙酯/N-叔丁基丙烯酰胺三元共聚物,
-增稠剂,诸如琼脂。瓜耳胶、藻酸盐、黄原胶、阿拉伯胶、刺梧桐树胶、角豆粉、亚麻子胶、葡聚糖、纤维素衍生物,例如甲基纤维素、羟烷基纤维素和羧甲基纤维素、淀粉组分和衍生物,诸如直链淀粉、支链淀粉和糊精、粘土,诸如膨润土或全合成水胶体,诸如聚乙烯醇,
-结构剂,诸如葡萄糖和马来酸,
-毛发调节化合物,诸如磷脂,例如大豆卵磷脂、鸡蛋卵磷脂和脑磷脂,以及硅油,
-蛋白质水解产物,更特别是弹性蛋白、胶原蛋白、角蛋白、乳蛋白、大豆蛋白和小麦蛋白的水解产物、它们与脂肪酸的缩合产物和季铵化蛋白质的水解产物,
-芳香油,二甲基异山梨糖醇酐和环糊精,
-增溶剂,诸如乙醇、异丙醇、乙二醇、丙二醇、甘油和二甘醇,
-去头屑剂,诸如Piroctone Olamine和Zink Omadine,
-调节pH值的其它物质,
-活性物质,诸如泛酰醇、泛酸、尿囊素、吡咯烷酮羧酸及其盐、植物提取物和维生素,
-胆固醇,
-UV吸收剂,
-稠度提供剂,诸如糖酯、多元醇酯或多元醇烷基醚,
-脂肪和蜡,诸如鲸蜡、蜂蜡、褐煤蜡、石蜡、脂肪醇和脂肪酸酯,
-脂肪酸烷醇酰胺,
-配位剂,诸如EDTA、NTA和磷酸,
-溶胀和渗透剂,诸如甘油、丙二醇单乙醚、碳酸盐、碳酸氢盐、胍、脲以及一代、二代和三代磷酸盐,
-遮光剂,诸如乳胶,
-珠光剂,诸如单-和二硬脂酸乙二醇酯,
-推进剂,诸如丙烷/丁烷混合物、N2O、二甲醚、CO2和空气,以及
-抗氧化剂。
在生产本发明的着色剂时,所用的含水载体的组分的量是为此目的的常用量。例如所用的乳化剂的浓度是0.5-30wt%、增稠剂的浓度是0.1-25wt%,基于着色剂总量计算。
原则上,颜色的氧化显色可以用大气氧来进行。但最好使用化学氧化剂,特别是在人的头发不仅需要着色而且需要有光泽时尤为如此。适合的氧化剂是过硫酸盐、亚氯酸盐,以及特别是过氧化氢或其与脲的加成产物、三聚氰胺或硼酸钠。氧化也可用酶来进行。在这种情况下,可利用酶将大气氧传送给显色剂组分或提高少量存在的氧化剂的作用。酶催方法的一个实例是这样一个过程,其中少量(例如1%和1%以下,基于配方总量计算)过氧化氢的效果被过氧化酶提高了。
氧化剂制剂最好是直接在毛发染色之前与氧化染料前体制剂混合。所形成的现用染发制剂最好应有6-10的pH值范围。在一优选的具体实施方案中,毛发着色剂是在一弱碱性介质中使用的。其应用温度可在15-40℃范围。在接触约30分钟后,漂洗被染的毛发,除去毛发着色剂。当使用高含量表面活性剂的载体,例如染色香波时,无需再用香波洗涤毛发。
下面以实施例对本发明进行说明。
实施例
1.合成实施例
4-氨基-2-(((5-氨基-2-羟基苯基)甲氧基)-甲基)苯酚合成
重氮溶液(A溶液):
在+5℃下在由26克(0.15摩尔)磺胺酸和75毫升(0.15摩尔)2N苛性钠溶液组成的溶液中加入10.35克(0.15摩尔)于125毫升水中的亚硝酸钠。在冷却(+5℃)下,在30分钟内滴加131毫升(0.38摩尔)10%盐酸。
将溶液A滴加到由17.25克(0.075摩尔)双-(2-羟基苄基)-醚于120毫升(0.3摩尔)10%苛性钠溶液中形成的冰冷却的溶液中。在加入结束之后,在20℃下搅拌1.5小时。
之后在2分钟内加入69克(0.4摩尔)连二亚硫酸钠。在75℃下20分钟之后,吸滤出产物,并用水洗涤。获得的产物是无色晶体,熔点175℃(分解)。
2.染色
首先制备具有下列组成的膏基料(除非另外指明,所有的量均以克表示):
牛油脂肪醇 17.0
Lorol_techn.1 4.0
Texapon_N 28 2 40.0
Dehyton_K 3 25.0
Eumulgin_B 24 1.5
蒸馏水 12.5
1 C12-18脂肪醇(HENKEL)
2 十二烷基醚硫酸钠(约28%活性物质;INCI名Sodium LaurethSulfate)(HENKEL)
3 有甜菜碱结构的脂肪酸酰胺衍生物,相应于下列的化学式:
R-CONH(CH2)3N+(CH3)2CH2COO-(约30%活性物质;INCI名:
Cocoamidopropyl Betaine)(HENKEL)
4 含约20摩尔EO的鲸蜡基十八烷醇(INCI名:Ceteareth-20)(HENKEL)
以此膏基料为基础制备了下列的毛发染色膏乳剂:
膏基料 50.0
显色剂组分 7.5毫摩尔*
成色剂组分 7.5毫摩尔*
Na2SO3(抑制剂) 1.0
(NH4)2SO4 1.0
浓氨溶液加至 pH 10
水加至 100
*除非另外指明
各组分按所列次序混合。任选地在相应降低水含量的情况下还可加入直接染料。在加入氧化染料前体和抑制剂后,先将乳液用浓氨水调至pH10,然后再用水配制到100克。
用3%双氧水溶液作为氧化剂进行氧化显色。为此,向100克的乳液加入50克过氧化氢溶液(9%)并混合。
将染色乳膏涂在标准的90%灰白但未经特别处理的5厘米长的一束人发上,在32℃下让其在头发上保留30分钟。完成染色过程后,漂洗头发,再用常规洗发剂洗涤,然后干燥。用于染色的显色剂组分和成色剂组分和直接染料如下:
显色剂组分
·4-氨基-2-(((5-氨基-2-羟基苯基)甲氧基)-甲基)苯酚(E1)
·2,4,5,6-四氨基嘧啶(E2)
·4,5-二氨基-1-(2-羟基乙基)吡唑(E3)
·对苯二胺(E4)
·N,N-双(2-羟乙基)对苯二胺(E5)
·4-羟基-2,5,6-三氨基嘧啶(E6)
·对甲苯二胺(E7)
·2-(2,5-二氨基苯基)乙醇(E8)
·2-氨甲基-4-氨基苯酚(E9)
·4-氨基-3-甲基苯酚(E10)
·双-(2-羟基-5-氨基苯基)甲烷(E11)成色剂组分
·1-萘酚(K1)
·2-甲基-5-氨基苯酚(K2)
·2-氯-6-甲基-3-氨基苯酚(K3)
·2-氨基-3-羟基吡啶(K4)
·2,6-二甲基-3-氨基苯酚(K5)
·间氨基苯酚(K6)
·2,7-二羟基萘(K7)
·4-氯间苯二酚(K8)
·2-甲基-4-氯-5-氨基苯酚(K9)
·6-甲基-1,2,3,4-四氢喹喔啉(K10)
·2-甲基间苯二酚(K11)
·3-氨基-2-甲氨基-6-甲氧基吡啶(K12)
·2,4-二氨基苯氧基乙醇(K13)
·3-甲基磺酰基氨基-2-甲基苯胺(K14)
·1,7-二羟基萘(K15)
·3,4-亚甲基二氧基苯酚(K16)
·3,4-亚甲基二氧基苯胺(K17)
·间苯二胺(K18)
直接染料
·6-硝基-1,2,3,4-四氢喹喔啉(D1)
·2-硝基-4-氨基-二苯胺-2'-羧酸(D2)
·2-氨基-6-氯-4-硝基苯酚(D3)
·2-硝基-1-氨基-4-双-(2-羟基乙基)氨基苯(D4)
·2-硝基-1-(2-羟基乙基)-氨基-4-甲基苯(D5)
·2-(2'-羟基乙基氨基)-4,6-二硝基苯(D6)
·1-(2'-羟基乙基)-氨基-2-硝基-4-双-(2-羟基乙基)-氨基苯(D7)
·1-(2-羟基乙基)-氨基-2-硝基-4-氨基苯(D8)
·4-(2-硝基苯基)-氨基苯酚(D9)
得到的染色如下:
显色剂 | 成色剂 | 直接染料 | 染色头发的色调 |
E1 | K1 | - | 灰红 |
E1 | - | - | 灰桔黄色 |
E1 | - | - | 棕红 |
E1 | K4 | - | 浅桔黄色 |
E1 | - | - | 灰红 |
E1 | K6 | - | 黄玉黄 |
E1+E32 | K1+K32 | - | 暗玫瑰色 |
E1+E22 | K2+K72 | - | 暗紫色 |
E1+E62 | K8+K92 | - | 灰红 |
E1+E72 | K10+K112 | - | 香槟酒色 |
E1+E42 | K12 | - | 黑色 |
E1+E52 | K5+K132 | - | 深蓝 |
E1+E82 | K12+K142 | - | 蓝灰 |
E1+E92 | K15+K162 | 0,1重量-%D1 | 棕黄色 |
E1+E102 | K17 | 0,3重量-%D2 | 暗红 |
E1+E112 | K18 | 0,1重量-%D3 | 发棕色 |
E1 | - | 0,1重量-%D4+0,1重量-%D5 | 铜色 |
E1 | K3 | 0,1重量-%D6+0,1重量-%D7 | 番茄红 |
E1 | K9 | 0,1重量-%D8+0,1重量-%D9 | 色淀红 |
a各0.375毫摩尔
Claims (13)
2.权利要求1所述的对氨基苯酚衍生物,其特征在于基团X为氧或硫原子,特别是氧原子。
3.权利要求1或2所述的对氨基苯酚衍生物,其特征在于不代表-OH的基团A、B、C和D是-NH2基团。
4.权利要求1-3之任一项所述的对氨基苯酚衍生物,其特征在于R1和R2代表氢。
5.权利要求1-4之任一项所述的对氨基苯酚衍生物,其特征在于基团
-R1和R2是相同的以及
-A和C是相同的和
-B和D是相同的。
6.4-氨基-2-(((5-氨基-2-羟基苯基)甲氧基)-甲基)苯酚。
7.权利要求1-6之任一项所述的对氨基苯酚衍生物和其生理上可接受的盐在氧化着色剂中作为显色剂组分的应用。
8.一种用于角蛋白纤维染色的氧化着色剂,它在含水载体中含成色剂组分和显色剂组分,其特征在于它含有权利要求1-6之任一项的对氨基苯酚衍生物作为显色剂组分。
9.权利要求8所述的氧化着色剂,其特征在于它含有选自1-萘酚、间氨基苯酚、5-氨基-2-甲基苯酚、3-甲基磺酰基氨基-2-甲基苯胺、3-氨基-2-甲氨基-6-甲氧基吡啶、2,6-二甲基-3-氨基苯酚、2,4-二氨基苯氧基乙醇、2,7-二羟基萘、6-甲基-1,2,3,4-四氢喹喔啉、1,7-二羟基萘、2-甲基-4-氯-5-氨基苯酚、3,4-亚甲基二氧基苯胺、2-甲基间苯二酚、4-氯间苯二酚、3,4-亚甲基二氧基苯酚、2-氨基-3-羟基吡啶和2-氯-6-甲基-3-氨基苯酚的至少一种成色剂组分。
10.权利要求8或9所述的氧化着色剂,其特征在于除了权利要求1至6之任一项的对氨基苯酚衍生物外,它还含至少一种其它的显色剂组分。
11.权利要求10所述的氧化着色剂,其特征在于所述其它的显色剂组分选自2,4,5,6-四氨基嘧啶、4-羟基-2,5,6-三氨基嘧啶、4,5-二氨基-1-(2-羟乙基)吡唑、对甲苯二胺、2-氨甲基-4-氨基苯酚、N,N-双-(2-羟乙基)-对苯二胺、对苯二胺、2-(2,5-二氨基苯基)乙醇、3-甲基-对-氨基苯酚和双-(2-羟基-5-氨基苯基)甲烷。
12.权利要求8-11之任一项所述的氧化着色剂,其特征在于显色剂组分的存在量为0.005-20wt%、优选0.1-5wt%;成色剂组分的存在量为0.005-20wt%、优选0.1-5wt%,分别基于氧化着色剂总量计算。
13.权利要求8-11之任一项所述的氧化着色剂,其特征在于还包含至少一种直接染料。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19756137A DE19756137A1 (de) | 1997-12-17 | 1997-12-17 | Neue p-Aminophenol-Derivate und deren Verwendung |
DE19756137.3 | 1997-12-17 |
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CN1282317A true CN1282317A (zh) | 2001-01-31 |
Family
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CN98812299.5A Pending CN1282317A (zh) | 1997-12-17 | 1998-12-08 | 新型对氨基苯酚衍生物及其用途 |
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EP (1) | EP1044185A2 (zh) |
JP (1) | JP2002508351A (zh) |
CN (1) | CN1282317A (zh) |
AU (1) | AU3248499A (zh) |
BR (1) | BR9813819A (zh) |
CA (1) | CA2315197A1 (zh) |
DE (1) | DE19756137A1 (zh) |
HU (1) | HUP0004392A2 (zh) |
NO (1) | NO20003128L (zh) |
PL (1) | PL341599A1 (zh) |
SK (1) | SK9152000A3 (zh) |
WO (1) | WO1999031054A2 (zh) |
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CN103764111A (zh) * | 2011-09-15 | 2014-04-30 | 莱雅公司 | 包含阳离子对氨基苯酚氧化显色碱的染料组合物 |
Families Citing this family (5)
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FR2767688B1 (fr) * | 1997-09-01 | 1999-10-01 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant un diamino pyrazole ou un triamino pyrazole et un meta-aminophenol halogene, et procede de teinture |
DE19936442A1 (de) | 1999-08-03 | 2001-02-08 | Henkel Kgaa | Neue Entwickler-Kuppler-Kombinationen |
DE19962871A1 (de) * | 1999-12-24 | 2001-06-28 | Henkel Kgaa | Neue Farbstoffkombination |
FR2848436A1 (fr) * | 2002-12-13 | 2004-06-18 | Oreal | Composition tinctoriale comprenant une paraphenylenediamine tertiaire cationique et un paraaminophenol, procedes et utilisations |
WO2022230090A1 (ja) * | 2021-04-28 | 2022-11-03 | ホーユー株式会社 | 染毛剤組成物 |
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FR2637282B1 (fr) * | 1988-09-13 | 1990-12-07 | Oreal | Para-aminophenols 2-substitues et leur utilisation pour la teinture des fibres keratiniques |
DE3914253A1 (de) * | 1989-04-29 | 1990-10-31 | Wella Ag | Oxidationshaarfaerbemittel auf der basis von 4-aminophenol-derivaten sowie neue 4-aminophenol-derivate |
KR100276113B1 (ko) * | 1992-05-15 | 2000-12-15 | 죤엠.산드레 | 가속 초임계 유체 추출법 |
-
1997
- 1997-12-17 DE DE19756137A patent/DE19756137A1/de not_active Withdrawn
-
1998
- 1998-12-08 BR BR9813819-7A patent/BR9813819A/pt not_active Application Discontinuation
- 1998-12-08 SK SK915-2000A patent/SK9152000A3/sk unknown
- 1998-12-08 JP JP2000538982A patent/JP2002508351A/ja active Pending
- 1998-12-08 CA CA002315197A patent/CA2315197A1/en not_active Abandoned
- 1998-12-08 CN CN98812299.5A patent/CN1282317A/zh active Pending
- 1998-12-08 PL PL98341599A patent/PL341599A1/xx unknown
- 1998-12-08 EP EP98967098A patent/EP1044185A2/de not_active Ceased
- 1998-12-08 WO PCT/EP1998/007961 patent/WO1999031054A2/de not_active Application Discontinuation
- 1998-12-08 HU HU0004392A patent/HUP0004392A2/hu unknown
- 1998-12-08 AU AU32484/99A patent/AU3248499A/en not_active Abandoned
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103764111A (zh) * | 2011-09-15 | 2014-04-30 | 莱雅公司 | 包含阳离子对氨基苯酚氧化显色碱的染料组合物 |
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DE19756137A1 (de) | 1999-06-24 |
BR9813819A (pt) | 2000-10-10 |
CA2315197A1 (en) | 1999-06-24 |
WO1999031054A3 (de) | 1999-09-10 |
PL341599A1 (en) | 2001-04-23 |
SK9152000A3 (en) | 2000-11-07 |
WO1999031054A2 (de) | 1999-06-24 |
HUP0004392A2 (hu) | 2001-04-28 |
NO20003128D0 (no) | 2000-06-16 |
EP1044185A2 (de) | 2000-10-18 |
AU3248499A (en) | 1999-07-05 |
JP2002508351A (ja) | 2002-03-19 |
NO20003128L (no) | 2000-06-16 |
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