CN1411493A - 使用阳离子染料的染发方法 - Google Patents
使用阳离子染料的染发方法 Download PDFInfo
- Publication number
- CN1411493A CN1411493A CN01806132.XA CN01806132A CN1411493A CN 1411493 A CN1411493 A CN 1411493A CN 01806132 A CN01806132 A CN 01806132A CN 1411493 A CN1411493 A CN 1411493A
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl
- hydrogen
- dyestuff
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims description 18
- 210000004209 hair Anatomy 0.000 title abstract description 20
- 125000002091 cationic group Chemical group 0.000 title abstract description 5
- 238000004040 coloring Methods 0.000 title abstract description 5
- 102000011782 Keratins Human genes 0.000 claims abstract description 11
- 108010076876 Keratins Proteins 0.000 claims abstract description 11
- 238000004043 dyeing Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- -1 ion imidazoles Chemical class 0.000 description 43
- 229910052799 carbon Inorganic materials 0.000 description 22
- 150000001721 carbon Chemical group 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
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- 150000002500 ions Chemical class 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000004061 bleaching Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
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- 229930195729 fatty acid Natural products 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- 238000001914 filtration Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 239000003581 cosmetic carrier Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000001048 orange dye Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003531 protein hydrolysate Substances 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 244000208060 Lawsonia inermis Species 0.000 description 2
- 241000123069 Ocyurus chrysurus Species 0.000 description 2
- 239000004218 Orcein Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- OEYQBKYISMRWQB-UHFFFAOYSA-N Santal Chemical compound C=1C(OC)=CC(O)=C(C2=O)C=1OC=C2C1=CC=C(O)C(O)=C1 OEYQBKYISMRWQB-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
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- ICVRBKCRXNVOJC-UHFFFAOYSA-N 1-amino-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2NC ICVRBKCRXNVOJC-UHFFFAOYSA-N 0.000 description 1
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- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
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- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical class NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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Abstract
权利要求1所限定的式(1)的阳离子染料特别适于对含角蛋白纤维进行染色,更特别适于对人发进行染色。
Description
本发明涉及使用阳离子咪唑染料对含角蛋白纤维进行染色的方法,涉及新型咪唑染料及其制备方法。
由EP-A-714 954已经知道一种适于染发的阳离子咪唑偶氮染料,它是通过重氮化4-烷氧基苯胺、与咪唑偶联、随后烷基化和季铵化、并最后与对苯二胺反应而得到的。但是该染料不能满足这类染发染料在实际中的所有要求,特别是其在水溶液中的稳定性不能令人满意。
现在已经发现可以通过酰化这种染料的游离芳香氨基或用烷氧基基团取代该基团来克服这一缺点。结果稳定性得到了适当改进并且该染料在较高pH值下,例如pH值为5-10时也具有足够的储存稳定性,这对染发配方是特别具有决定性优势的。
其中
Y1和Y2各自独立地为氢、未取代或取代的C1-C4烷基、或卤素,
R1和R2各自独立地为氢或未取代或取代的C1-C4烷基,
R3和R4各自独立地为氢、未取代或取代的C1-C4烷基、C1-C4烷氧基或卤素,
R5为氢、C1-C4烷基、C1-C4烷氧基或卤素,
X为C1-C12烷氧基或式-N(R6)-CO-R7的基团,其中R6为氢或C1-C4烷基而R7为氢、C1-C4烷基或-NH2,并且
A-为阴离子。
根据本发明,烷基基团一般理解为开链或支化的烷基基团,例如甲基、乙基、正和异丙基及正、仲和叔丁基。
烷基基团可以被例如羟基、羧基、卤素、氰基或C1-C4烷氧基单或多取代。
烷氧基基团可含有1-12个碳原子,优选1-4个碳原子。它们为例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基或正己氧基。烷氧基基团也可被例如所提到的用于取代烷基基团的可能取代基基团,特别是羟基或C1-C4烷氧基取代。
无机和有机阴离子均可考虑作为阴离子A-,例如卤化物如氯化物、溴化物或碘化物、硫酸盐、硫酸氢盐、甲基硫酸盐、四氟化硼、氨基磺酸盐、高氯酸盐、碳酸盐、碳酸氢盐、磷酸盐、硝酸盐、苯磺酸盐、甲酸盐、乙酸盐、丙酸盐、乳酸盐,以及复合阴离子,如氯化锌双盐阴离子。
阴离子一般是由制备过程控制的。优选存在氯化物、硫酸氢盐、硫酸盐、甲基硫酸盐、磷酸盐、甲酸盐、乳酸盐或乙酸盐。
卤素应理解为氟、氯、溴或碘,特别是氯。
Y1和Y2各优选为甲基并特别为氢。
R1和R2各优选为乙基、羟乙基或甲基。
R3和R4各优选为甲氧基、甲基、氢或氯。
R5优选为氢。
X优选为未取代的C1-C4烷氧基或-NH-CO-R7基团,其中R7特别为氢、甲基、乙基或-NH2。
其中
R1和R2各为甲基或乙基,
X为未取代的C1-C4烷氧基或-NH-CO-R7基团,其中R7为氢、甲基、乙基或-NH2,并且
A-为阴离子。
式(2)的染料是新型的并且本发明也涉及它。
式(1)和(2)的染料是例如通过本身已知的方式酰化式(3)化合物中的游离氨基基团而制备的,
其中Y1,Y2,R1,R2,R3,R4,R5和A-定义如式(1)。例如它是通过与适当的酸如甲酸或乙酸、酸酐如乙酸酐、或KOCN反应而进行的。
X为烷氧基的式(1)和(2)的化合物是例如通过使式(4)的化合物与对烷氧基苯胺在本身已知的反应条件下反应而获得的,其中Y1,Y2,R1,R2,R3和R4定义如式(1)而R8为C1-C4烷基。式(3)和(4)的化合物是已知的或者可以本身已知的方式获得。式(1)和(2)的染料适于对含角蛋白纤维进行染色。“含角蛋白纤维”应理解为羊毛、毛皮、羽毛,且特别是人发。
本发明还涉及包含这种用于对含角蛋白纤维进行染色的染料的组合物。
式(1)和(2)的化合物在根据本发明的组合物中优选以占总染色组合物0.001%-5%,特别是0.01%-1%的量存在。
根据本发明所用的式(1)和(2)染料的色调多样性和颜色牢度可以通过与染发组合物领域中所用的其它染料组合而得到提高。它们可以非常容易地与氧化染料及直接染料合用,后者可以是阳离子性的或者也可以是不带电荷的。只有在阴离子直接染料的情况下才要求一定程度的小心谨慎,因为在某些条件下配方中可能出现沉淀。
在所有的染色组合物中,还可以联合使用多种不同的染色物质;同样可以在显色剂和着色剂化合物组中联合使用多种不同的氧化染料前体,例如带有伯或仲氨基基团的芳香化合物、含氮的杂环化合物、芳羟基化合物或氨基酸,如德国专利申请19 717 224.5,特别是第3页31行至第5页8行所述。
根据本发明式(1)和(2)的染料在红紫色至紫色范围内产生颜色色调,并且牢度性能优异。值得注意的是其仍可使颜色已经很深的头发显著改变色调的性能。
对于染发,优选使用式(1)的染料与一种或多种另外的阳离子染料,特别是在WO 95/01772第11-27页中所述者混合。特别适宜的是包括式(1)染料以及根据WO 95/1772实施例1的黄色染料和/或实施例4的红色染料和/或实施例46的橙色染料的染料混和物。
在另一个实施方案中,出于进一步改进色调的目的,本发明的染色组合物除了包括本发明式(1)的染料外,还包括常规直接染料,例如硝基苯胺、硝基苯二胺、硝基氨基苯酚、蒽醌、靛酚、吩嗪、吩噻嗪、甲川或被称作Arianors的化合物,例如国际名称或商品名如下的化合物:HC Yellow 2,HC Yellow 4,HC Yellow 6,Basic Yellow 57,Basic Yellow 9,Disperse Orange 3,HC Red 3,HC Red BN,BasicRed 76,Basic Red 2,Basic Violet 14,Basic Blue 3,Basic Blue6,Basic Blue 7,Basic Blue 9,Basic Blue 12,Basic Blue 26,HC Blue 2,HC Blue 7,HC Blue 12,Disperse Blue 3,Basic Blue99,HC Violet 1,Disperse Violet 1,Disperse Violet 4,DisperseBlack 9,Basic Brown 16和Basic Brown 17,以及苦氨酸、2-氨基-6-氯-4-硝基苯酚、4-氨基-2-硝基二苯胺-2’-酸、6-硝基-1,2,3,4-四氢喹喔啉、4-N-乙基-1,4-二(2’-羟乙基氨基)-2-硝基苯盐酸盐和1-甲基-3-硝基-4-(2’-羟乙基)-氨基苯。
同样非常适于与本发明染料合用的是阳离子化硝基苯胺和蒽醌染料,例如下列专利说明书中者:US-5 298 029,特别是第2栏33行至第5栏38行;US-5 360 930,特别是第2栏38行至第5栏49行;US-5169 403,特别是第2栏30行至第5栏38行;US-5 256 823,特别是第4栏23行至第5栏15行;US-5 135 543,特别是第4栏24行至第5栏16行;EP-A-818 193,特别是第2页40行至第3页26行;US-5486 629,特别是第2栏34行至第5栏29行;及EP-A-758 547,特别是第7页48行至第8页19行。
阳离子偶氮染料,例如根据GB-A-2 319 776者以及DE-A-29 912327中所述的噁嗪染料及与其中提到的其它直接染料的混和物同样可以很容易地合用。
根据该实施方案本发明组合物优选包含占总染色组合物0.01-5wt%的染料。
除此之外,本发明的染色组合物还可包含天然存在的染料,例如指甲红、中性指甲红、指甲黑、甘菊花、檀香、黑茶、泻鼠李皮、鼠尾草、苏木、茜草、儿茶、sedre和朱草根。这些染色方法在例如EP-A-404 868,特别是第3页55行至第4页9行有述。
关于其它的常规染料组分,可特别参考系列丛书“皮肤病学”,Ch.Culnan,H.Maibach编,Verlag Marcel Dekker Inc.,纽约,巴塞尔,1986,第7卷,Ch.Zviak,护发科学,第7章,248-250页(直接染料)和第8章,264-267页(氧化染料);及“EuropischesInventar der Kosmetikrohstoffe”,1996,欧洲委员会出版,可从Bundesverband der deutschen Industrie-und Handelsunternehmenfür Arzneimittel,Reformwaren und Krperpflegemittele.V.,曼海姆以磁盘形式获得。
氧化染料前体不必一定存在或者染料不必每种都是单独的化合物,而是在本发明的染色组合物中可以另外存在较小量的与各染料制备过程有关的其它组分,只要这种组分对染色结果没有不良影响或者不必因为诸如有毒等原因而被排除即可。
本发明式(1)的染料也可很容易地与染发时所用的其它染料和/或助剂合用,例如与下列物质合用:
-氧化剂,以获得更亮的颜色,如WO 97/20545特别是第9页5-9行所述,
-永久波浪定影液形式的氧化剂,如DE-A-19 713 698特别是第4页52-55行或EP-A-1 062 940特别是第6页41-47行所述(及在等价的WO 99/40895中所述),
-氧化染色组合物,如EP-A-850 636特别是第5页41行至第7页52行,EP-A-850 637特别是第6页50行至第8页44行,EP-A-850638特别是第7页20行至第9页26行及EP-A-852 135特别是第4页54行至第6页53行所述,
-含有阳离子成色剂的氧化染色组合物,如WO 99/48856特别是第9页16行至第13页8行及WO 99/48875特别是第11页20行至第12页13行所述,
-在氧化还原酶存在下的氧化染料,如WO 99/17730特别是第4页11行至第13页28行及WO 99/36034特别是第3页至第15页所述,
-可自氧化的氧化染料,如WO 99/20234特别是第26页16行至第28页15行所述,或者
-硝基苯衍生物,如WO 99/20235特别是第26页7行至第30页15行所述,
-多元醇或聚醚,如EP-A-962 219特别是第27页14行至第38行所述,
-增稠聚合物,如EP-A-970 684特别是第48页16行至第51页4行所述,
-含糖聚合物,如EP-A-970 687特别是第28页17行至第29页23行所述,
-季铵盐,如WO 00/10517特别是第44页16行至第46页23行所述,
-阴离子表面活性剂,如WO 00/10518特别是第45页11行至第48页3行所述,
-非离子表面活性剂,如WO 00/10519特别是第45页11行至第50页12行所述,或者
-硅酮,如WO 00/12057特别是第45页9行至第55页2行所述。
本发明的染色组合物即使是在生理上可忍受的低于45℃的温度下也能强烈着色。因此它们特别适合对人发进行染色。用于人发时,染色组合物通常可加入到水性化妆品载体中。适宜的水性化妆品载体包括例如油膏、乳液、凝胶及含表面活性剂的发泡溶液,例如洗发液或其它适用于含角蛋白纤维的制剂。这些形式的应用详述于研究揭密(Research Disclosure)42448(1999年8月)中。如果有必要,还可以将染色组合物加入到无水载体中,如US-3 369 970特别是第1栏70行至第3栏55行所述。本发明的染色组合物也非常适用于DE-A-3829 870中所述的使用染色梳或染色刷的染色方法。
本发明的染色组合物可进一步包括任何该类制剂中已知的活性成分、添加剂或助剂。许多情况下染色组合物包括至少一种表面活性剂,原则上阴离子以及两性离子、两性的、非离子和阳离子表面活性剂均是适用的。但是在许多情况下,经证明从阴离子、两性离子和非离子表面活性剂中选择表面活性剂是有利的。
适用于本发明制剂中的阴离子表面活性剂包括所有适用于人体的阴离子表面活性物质。这类物质的特征在于可给出水溶性的阴离子基团,例如羧酸盐、硫酸盐、磺酸盐或磷酸盐基团,及含有约10-22个碳原子的亲脂性烷基基团。此外,分子中可存在乙二醇或聚乙二醇醚基团、酯、醚和酰胺基团以及羟基基团。下面是适宜阴离子表面活性剂的实例,每种均为钠、钾或铵盐或链烷醇基团中含有2或3个碳原子的单、二或三链烷醇铵盐形式的:
-含有10-22个碳原子的线性脂肪酸(肥皂),
-式R-O-(CH2-CH2-O)x-CH2-COOH的醚羧酸,其中R为含有10-22个碳原子的直链烷基基团,并且x=0或1-16,
-酰基基团中含有10-18个碳原子的酰基肌氨酸盐,
-酰基基团中含有10-18个碳原子的酰基牛磺酸盐,
-酰基基团中含有10-18个碳原子的酰基异硫代硫酸酸盐,
-烷基基团中含有8-18个碳原子的磺基琥珀酸一或二烷基酯及烷基基团中含有8-18个碳原子和1-6个氧醚基团的磺基琥珀酸一烷基聚乙氧基醚酯,
-含有12-18个碳原子的直链烷磺酸盐,
-含有12-18个碳原子的线性α-烯烃磺酸盐,
-含有12-18个碳原子的脂肪酸α-磺基脂肪酸甲酯,
-式R’-O(CH2CH2-O)x’-SO3H的烷基硫酸盐和烷基聚乙二醇醚硫酸盐,其中R’优选为含有10-18个碳原子的直链烷基基团,并且x’=0或1-12,
-根据DE-A-3 725 030特别是第3页40-55行的表面活性的羟基磺酸盐的混和物,
-根据DE-A-3 723 354特别是第4页42-62行的硫酸盐化羟基烷基聚乙二醇和/或羟基亚烷基丙二醇醚,
-根据DE-A-3 926 344特别是第2页36-54行的含有12-24个碳原子和1-6个双键的不饱和脂肪酸的磺酸盐,
-酒石酸和柠檬酸与醇的酯,为约2-15个分子的环氧乙烷和/或环氧丙烷与含有8-22个碳原子的脂肪醇的加成产物。
优选的阴离子表面活性剂为烷基基团中含有10-18个碳原子且分子中最多带有12个乙二醇醚基团的烷基硫酸盐、烷基聚乙二醇醚硫酸盐和醚羧酸,且特别是饱和及不饱和C8-C22羧酸,如油酸、硬脂酸、异硬脂酸和棕榈酸的盐。
分子中带有至少一个季铵盐基团和至少一个-COO(-)或-SO3 (-)基团的表面活性化合物被称作两性离子表面活性剂。特别适宜的两性离子表面活性剂为所谓的甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰基氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰基氨基丙基二甲基甘氨酸铵,和烷基或酰基基团中含有8-18个碳原子的2-烷基-3-羧甲基-3-羟乙基咪唑啉以及椰油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为CTFA名被称作椰油酰胺基丙基甜菜碱的脂肪酸酰胺衍生物。
两性表面活性剂应理解为是指分子中除C8-C18-烷基或酰基外还含有至少一个游离氨基基团和至少一个-COOH或-SO3H基团并且可以形成内盐的表面活性化合物。适宜两性表面活性剂的实例包括N-烷基氨基乙酸、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-烷基酰胺基丙基氨基乙酸、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,每种均在烷基基团中带有约8-18个碳原子。特别优选的两性表面活性剂为N-椰油烷基氨基丙酸盐、椰油酰氨基乙氨基丙酸盐和C12-C18酰基肌氨酸。
非离子表面活性剂包含例如多元醇基团、聚亚烷基二醇醚基团或多元醇与聚二醇醚基团的组合作为亲水基团。
这类化合物为例如:
-2-30mol环氧乙烷和/或0-5mol环氧丙烷与含有8-22个碳原子的线性脂肪醇、与含有12-22个碳原子的脂肪酸以及与烷基基团中含有8-15个碳原子的烷基苯酚的加成产物,
-1-30mol环氧乙烷与甘油的加成产物C12-C22-脂肪酸一和二酯,
-C8-C22-烷基一和低聚糖苷及其乙氧基化同系物,
-5-60mol环氧乙烷与蓖麻油及氢化蓖麻油的加成产物,
-环氧乙烷与山梨糖醇脂肪酸酯的加成产物,
-环氧乙烷与脂肪酸链烷醇酰胺的加成产物。
可用于本发明发处理组合物中的阳离子表面活性剂的实例特别为季铵盐化合物。优选卤化铵,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(十六基)甲基氯化铵。其它可用于本发明的阳离子表面活性剂为季铵化蛋白质水解产物。
同样适于本发明的是阳离子硅油,例如市售产品Q2-7224(制造商:Dow Corning;一种稳定化三甲基甲硅烷基amodimethicone)、DowCorning 929乳液(包括羟氨基改性的硅酮,也被称作amodimethicone)、SM-2059(制造商:General Electric)、SLM-55067(制造商:Wacker)以及Abil-Quat 3270和3272(制造商:Th.Goldschmidt;二季铵化的聚二甲基硅氧烷,季铵盐-80)。
烷基酰胺基胺,特别是脂肪酸酰胺基胺,如可以商品名TegoAmid18获得的硬脂基酰胺基丙基二甲基胺不仅以良好的调理作用而闻名,而且特别是以其良好的生物降解性而著称。
季铵化酯化合物,所谓的“esterquats”,如以商标Stepantex出售的甲基羟基烷基二烷氧基烷基铵N-甲硫酸酯也是非常容易生物降解的。
一个可用作阳离子表面活性剂的季铵化糖衍生物的实例为市售产品Glucquat100,根据CTFA命名法称作“月桂基甲基gluceth-10羟丙基二氯化monium”。
用作表面活性剂的含烷基基团化合物可以是单一物质,但在制备这类物质时使用植物或动物源的天然原材料一般是优选的,结果所得的物质混和物根据所用的特殊起始原料而含有不同的烷基链长。
作为环氧乙烷和/或丙烷与脂肪醇加成产物或这类加成产物衍生物的表面活性剂可以是具有“正常”同系物分布的产物或具有限制性同系物分布的产物。“正常”同系物分布应理解为是指在使用碱金属、碱金属氢氧化物或碱金属醇盐作催化剂的脂肪醇与环氧烷烃的反应中所获得的同系物混和物。另一方面,限制性同系物分布是在例如使用水滑石、醚羧酸的碱金属盐、碱金属氧化物、氢氧化物或醇盐作催化剂时获得的。可优选使用具有限制性同系物分布的产物。
其它活性组分、助剂和添加剂的实例如下:
-非离子聚合物,例如乙烯基吡咯烷酮/乙烯基丙烯酸酯共聚物、聚乙烯基吡咯烷酮和乙烯基吡咯烷酮/乙烯基乙酸酯共聚物及聚硅氧烷,
-阳离子聚合物,如季铵化纤维素醚、带有季铵基团的聚硅氧烷、二甲基二烯丙基氯化铵聚合物、二甲基二烯丙基氯化铵和丙烯酸的共聚物(以商品名MerquatR 280有售并且其在染发中的应用在例如DE-A-4 421 031特别是第2页20-49行或EP-A-953 334特别是第27页17行至第30页11行中有述)、丙烯酰胺/二甲基二烯丙基氯化铵共聚物、季铵化二乙基硫酸酯二甲氨基乙基甲基丙烯酸酯/乙烯基吡咯烷酮共聚物、乙烯基吡咯烷酮/咪唑啉鎓-N-甲氯化物共聚物,
-季铵化聚乙烯醇,
-两性离子和两性聚合物,例如丙烯酰胺基丙基-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/叔丁基氨基乙基甲基丙烯酸酯/2-羟丙基甲基丙烯酸酯共聚物,
-阴离子聚合物,例如聚丙烯酸、交联聚丙烯酸、乙酸乙烯酯/丁烯酸共聚物、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/异冰片基丙烯酸酯共聚物、甲基乙烯基醚/马来酸酐共聚物和丙烯酸/丙烯酸乙酯/N-叔丁基丙烯酰胺三聚物,
-增稠剂,如琼脂、瓜耳豆胶、海藻酸盐、黄原酸胶、阿拉伯树胶、刺梧桐树胶、洋槐豆粉、亚麻子胶、右旋糖苷、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、淀粉片段及衍生物,如直链淀粉、支链淀粉和糊精、粘土,如斑脱土或全合成水状胶体如聚乙烯醇,
-结构剂,如葡萄糖和马来酸,
-头发调理化合物,如磷脂,例如大豆磷脂、卵磷脂和脑磷脂、硅油、以及诸如DE-A-19 729 080特别是第2页20-49行、EP-A-834 303特别是第2页18行至第3页2行或EP-A-312 343特别是第2页59行至第3页11行中所述的调理化合物,
-蛋白质水解产物,特别是弹性蛋白、胶原质、角蛋白、乳蛋白、大豆蛋白质和小麦蛋白质水解产物、其与脂肪酸的缩合产物以及季铵化蛋白质水解产物,
-芳香油、二甲基异山梨糖醇和环糊精,
-增溶剂,如乙醇、异丙醇、乙二醇、丙二醇、甘油和二甘醇,
-抗头皮屑活性成分,如piroctones,olamines和锌万亩定,
-调节pH值的其它物质,
-活性成分如泛酰醇、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,
-光稳定剂和紫外吸收剂,例如在EP-A-819 422特别是第4页34-37行中所述,
-稠度调节剂,如糖酯、多元醇酯或多元醇烷基醚,
-脂肪和蜡,如鲸油、蜂蜡、褐煤蜡、石蜡、脂肪醇和脂肪酸酯,
-脂肪链烷醇酰胺,
-分子量为150-50 000的聚乙二醇和聚丙二醇,例如在EP-A-801942特别是第3页44-55行中所述,
-络合剂,如EDTA,NTA和膦酸,
-膨胀和渗透物质,如广泛列于例如EP-A-962 219特别是第27页18-38行中的多元醇和多元醇醚,例如甘油、丙二醇、丙二醇单乙基醚、丁二醇、苯甲醇、碳酸酯、碳酸氢酯、胍、脲以及伯、仲和叔磷酸酯、咪唑、丹宁酸、吡咯,
-遮光剂,如胶乳,
-光泽剂,如乙二醇单和二硬脂酸酯,
-气雾挥发剂,如丙烷-丁烷混和物、N2O、二甲醚、CO2和空气,以及
-抗氧剂。
在制备本发明的染色组合物时水性载体组分的用量为其常规用量;例如乳化剂以占总染色组合物0.5-30wt%的浓度而增稠剂以0.1-25wt%的浓度使用。
成品染色制剂的pH值通常为2-11,优选为5-10。
为了对含角蛋白纤维进行染色,特别是对人发进行染色,通常将50-100g水性化妆品载体形式的染色组合物施用在头发上,停留约30分钟并随后用市售洗发液漂洗或冲洗。
本发明所用染料及任选使用的氧化染料前体可同时或连续施用到含角蛋白纤维上,其使用顺序是无关紧要的。
本发明所用染料及本发明组合物中任选使用的氧化染料前体可分开或共同保存在液体至类似膏体制剂(水性或非水性)中或以干粉形式保存。当组分共同保存在液体制剂中时,制剂应该是基本无水的以降低各组分的反应。当它们分开保存时,反应性组分在马上要使用前彼此充分混合。在干燥储存的情况下,使用前通常加入一定量的热水(50-80℃)制备成均匀的混和物。
下列实施例用来说明本发明而非对其进行限制。除非特别指明,份和百分比是指重量的。
实施例1:
将16g下式的化合物:
加入到65g乙酸酐中并在约75℃的水浴中搅拌2小时,经过这一段时间所有起始原料均消失。冷却后,进行过滤并随后用乙酸酐冲洗。为了除去乙酸酐,将滤饼悬浮在200ml异丙醇中,并将悬浮液搅拌2小时,再次过滤并用异丙醇冲洗。得到17.8g非常纯的下式的化合物:
在水溶液中,该化合物将漂白的牦牛毛染成鲜艳的淡红紫色。
乙酰化反应也可在溶剂,例如水中进行:
将110g上述起始化合物悬浮在300ml水中,并在约70℃于1小时内将61.4g乙酸酐(过量100%)全部加入。搅拌下将反应混和物冷却,随后过滤并用水冲洗。干燥后,得到122.5g乙酰化化合物,其中只存在痕量起始原料。
实施例2:
搅拌下将15g下式化合物:
缓慢加入到30g甲酸(98%)中并在65℃下加热3小时。将100ml异丙醇滴加到热溶液中,随后搅拌直至冷却。过滤,然后用异丙醇彻底洗涤。首先在刚刚回流下将潮湿的滤饼搅拌到65ml甲醇中,然后在45℃过滤,随后用甲醇洗涤。然后将滤饼溶解在1.5升甲醇中,澄清溶液并使用旋转蒸发仪将母液浓缩至约85g,在此过程中已经有部分染料沉淀出来。冷却抽滤后,用少量甲醇洗涤并干燥。得到大约9g下式化合物:
在水溶液中,该染料将漂白的牦牛毛染成鲜艳的淡红紫色。
实施例3:
在冰浴装置中将10.3g下式化合物:
溶解在33ml 1N的盐酸中。将30g冰加入到反应溶液中,然后在半小时内分次加入2.4g氰酸钾。临近结束时形成蜂蜜状残留物,有时可能会堵塞搅拌器。在冰浴中放置1-2小时后,残留物变成可以很容易用玻璃棒粉碎的脆块。很容易再次搅拌的悬浮液仍含有相当量的起始原料,因此再加入9ml HCl(1N)和1.2g KOCN。然后移走冰浴并在室温进行过滤。将残留物再次悬浮在水中并在75℃搅拌2小时。冷却后,进行过滤并用水洗涤。
为了纯化,将残留物热溶在12升甲醇中并通过预热减压抽滤的方法澄清溶液。使用旋转蒸发仪将母液浓缩至约2升,沉淀出纯染料。冷却后,过滤并用甲醇洗涤,得到24g下式化合物:
在水溶液中,该染料将漂白的牦牛毛染成鲜艳的紫色,其色调比实施例2的甲酸基取代染料的色调更少地显浅红。
实施例4:
分次加入并将该混和物在氮气下于90℃的水浴中搅拌80小时。趁热再用50g二甲基甲酰胺将反应混和物稀释,稍微冷却后在约40℃过滤。再用50g DMF分次洗涤结晶滤饼,最后彻底抽滤干燥。
在水溶液中,该染料将漂白的牦牛毛染成鲜艳的浅红紫色。
实施例5:
用柠檬酸将10%的非离子表面活性剂(Plantaren2000[Henkel])溶液调节至pH9.5。将0.06%来自实施例1的染料溶解在其中。在室温用2g染料溶液处理一绺1g未损伤人发(“意大利白色新发”,ImhairLtd)20分钟并随后进行冲洗和洗涤。得到非常诱人的紫色,洗涤8次之后仍清晰可见。着色对光的牢度是优异的。
实施例6:
用柠檬酸将10%的非离子表面活性剂(Plantaren2000[Henkel])溶液调节至pH5.5。将下列染料溶解在100g该溶液中:
0.2g根据WO 95/01772实施例1的黄色染料
0.05g根据本发明申请实施例4的染料。
在室温用2g上述染料溶液处理一绺1g未损伤人发(“意大利白色新发”,Imhair Ltd)20分钟并随后进行冲洗和洗涤。得到非常诱人的紫铜色,具有优异的洗涤、摩擦和光照牢度。
实施例7:
用柠檬酸将10%的非离子表面活性剂(Plantaren2000[Henkel])溶液调节至pH5.5。将下列染料溶解在100g该溶液中:
0.25g根据WO 95/01772实施例1的黄色染料
0.08g根据WO 95/01772实施例46的橙色染料
0.06g根据本发明申请实施例2的染料
0.11g根据WO 95/01772实施例6的蓝色染料。
在室温用双倍量的上述染料溶液处理一绺漂白的人发20分钟并随后进行冲洗和洗涤一次。得到具有优异的洗涤和摩擦牢度的黑色。
实施例8:
制备下列阳离子乳液基体:
3.8g山嵛酸氯化三monium(Genamin KDM-P[Hoechest])
4.0g十六烷醇(Lanette 16[Henkel])
0.5g苯氧基乙醇(Uniphen P23[Induchem])
0.1g香水(PO Cinque 226482{drom})
水加至100
将0.06g根据本申请实施例4的染料溶解在上述基体中并用一乙醇胺将pH调节到6.5。在室温用2g上述染料乳液处理一绺1g未损伤中等棕色人发(新中等棕色头发,Imhair Ltd.)20分钟,并随后进行冲洗和洗涤一次。头发获得了具有优异牢度性能的非常诱人的浓郁紫红色。
实施例9:
用柠檬酸将10%的非离子表面活性剂(Plantaren2000[Henkel])溶液调节至pH5.5。将下列染料溶解在100g该溶液中:
0.06g根据WO 95/01772实施例1的黄色染料
0.09g根据WO 95/01772实施例46的橙色染料
0.03g根据本发明申请实施例4的染料
0.07g根据WO 95/01772实施例6的蓝色染料。
在室温用双倍量的上述染料溶液分别处理一绺漂白的人发和一绺未损伤的白色人发各20分钟,并随后进行冲洗和洗涤一次。在两种情况下结果均为带有明显的非常诱人的淡紫色的深棕色。
实施例10:
将下列染料溶解在100g实施例5所述的非离子表面活性剂溶液(pH9.5)中:
0.14g Basic Red 76(ArianorR Madder Red),
0.14g根据本发明实施例4的染料,
0.28g Basic Blue 99(ArianorR Steel Blue),
0.28g HC Yellow 2和
0.14g根据WO 95/01772实施例1的黄色染料。
在室温用上述溶液处理一绺白色未损伤的人发20分钟。结果为带有诱人淡紫铜色的浅棕色。
实施例11:
步骤同实施例10,但用下列染料代替所述染料:
0.14g根据WO 95/01772实施例3的红色染料和
0.1g根据本发明实施例4的染料。
对白发染色的结果为具有优异牢度性能的非常诱人的浓郁宝石红色。
Claims (9)
1.一种对含角蛋白纤维进行染色的方法,该方法包括用式(1)的染料处理纤维,
其中
Y1和Y2各自独立地为氢、未取代或取代的C1-C4烷基、或卤素,
R1和R2各自独立地为氢或未取代或取代的C1-C4烷基,
R3和R4各自独立地为氢、未取代或取代的C1-C4烷基、C1-C4烷氧基或卤素,
R5为氢、C1-C4烷基、C1-C4烷氧基或卤素,
X为C1-C12烷氧基或式-N(R6)-CO-R7的基团,其中R6为氢或C1-C4烷基而R7为氢、C1-C4烷基或-NH2,并且
A-为阴离子。
2.根据权利要求1的方法,其中Y1和Y2各自独立地为甲基或特别为氢。
3.根据权利要求1或权利要求2的方法,其中R1和R2各自独立地为乙基、羟乙基或甲基。
4.根据权利要求1-3任意一项的方法,其中R3和R4各自独立地为甲氧基、甲基、氢或氯。
5.根据权利要求1-4任意一项的方法,其中R5为氢。
6.根据权利要求1-5任意一项的方法,其中X为未取代的C1-C4烷氧基或-NH-CO-R7基团,其中R7为氢、甲基、乙基或-NH2。
7.一种式(2)的染料:
其中
R1和R2各为甲基或乙基,
X为未取代的C1-C4烷氧基或-NH-CO-R7基团,其中R7为氢、甲基、乙基或-NH2,并且
A-为阴离子。
9.一种用于含角蛋白纤维染色的组合物,其包括至少一种根据权利要求1式(1)的染料。
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FR3083100B1 (fr) | 2018-06-27 | 2021-01-15 | Oreal | Composition de coloration comprenant un colorant direct, un sel peroxygene et une cyclodextrine, et procede mettant en oeuvre cette composition |
FR3083106B1 (fr) | 2018-06-29 | 2020-10-02 | Oreal | Procede de coloration des fibres keratiniques mettant en oeuvre un monosaccharide, un polysaccharide a groupes amines et une matiere colorante |
FR3090345B1 (fr) | 2018-12-21 | 2021-06-25 | Oreal | Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel ammonium aliphatique et composition les comprenant |
FR3090349B1 (fr) | 2018-12-21 | 2020-12-18 | Oreal | Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel hétérocyclique saturé et composition les comprenant |
FR3090358B1 (fr) | 2018-12-21 | 2020-12-18 | Oreal | Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel hétérocyclique insaturé et composition les comprenant |
FR3097438B1 (fr) | 2019-06-24 | 2021-12-03 | Oreal | Composition anhydre comprenant au moins une silicone aminée, au moins un alcoxysilane et au moins un agent colorant |
FR3097752B1 (fr) | 2019-06-27 | 2023-10-13 | Oreal | Procédé de coloration des fibres kératiniques mettant en œuvre un polycarbonate cyclique particulier, un composé comprenant au moins un groupement amine et un agent colorant, composition et dispositif |
FR3097760B1 (fr) | 2019-06-28 | 2022-04-01 | Oreal | Procédé de coloration des fibres kératiniques comprenant l’application d’un mélange extemporané d’un colorant direct etd’une composition comprenant un corps gras liquide, un corps gras solide et un tensioactif. |
FR3097755B1 (fr) | 2019-06-28 | 2021-07-16 | Oreal | Procédé de coloration des fibres kératiniques comprenant une étape de traitement par plasma froid desdites fibres |
FR3098114B1 (fr) | 2019-07-05 | 2022-11-11 | Oreal | Composition comprenant un colorant naturel, un colorant direct synthétique cationique hydrazono et/ou azoïque et un composé aromatique |
FR3103090A1 (fr) | 2019-11-20 | 2021-05-21 | L'oreal | Procédé de coloration ou d’éclaircissement mettant en œuvre un appareil de coiffure à main et un substrat |
FR3104983B1 (fr) | 2019-12-20 | 2023-11-24 | Oreal | Composition de coloration capillaire comprenant un colorant direct, une gomme de scléroglucane et un polymère associatif non ionique. |
FR3104952B1 (fr) | 2019-12-20 | 2022-08-26 | Oreal | Procédé de traitement cosmétique des fibres kératiniques mettant en œuvre une composition de coloration et une composition à base de terres rares |
FR3109313B1 (fr) | 2020-04-15 | 2022-11-25 | Oreal | Procede de traitement de matieres keratiniques mettant en oeuvre un polymere acrylique d’anhydride en dispersion huileuse et d’un compose hydroxyle et/ou thiole |
FR3111553A1 (fr) | 2020-06-22 | 2021-12-24 | L'oreal | Procédé de coloration des fibres kératiniques mettant en œuvre un colorant direct et un sel de saccharinate et composition les comprenant |
FR3111552B1 (fr) | 2020-06-23 | 2024-04-05 | Oreal | Composition pour la décoloration et la coloration simultanées des fibres kératiniques comprenant un sel hétérocyclique particulier et procédé mettant en œuvre cette composition |
FR3111557B1 (fr) | 2020-06-23 | 2022-11-25 | Oreal | Composition cosmétique comprenant un copolymère polyhydroxyalcanoate comprenant au moins deux unités polymériques différentes à chaine hydrocarbonée (in)saturée dans un milieu gras |
FR3111812B1 (fr) | 2020-06-24 | 2023-02-10 | Oreal | Composition cosmétique comprenant un copolymère polyhydroxyalcanoate greffé dans un milieu gras |
FR3117809B1 (fr) | 2020-12-18 | 2024-02-16 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3117807B1 (fr) | 2020-12-18 | 2024-03-01 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
EP4262995A1 (en) | 2020-12-18 | 2023-10-25 | L'oreal | Process for lightening keratin fibres |
FR3117805B1 (fr) | 2020-12-18 | 2024-02-16 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3117806B1 (fr) | 2020-12-18 | 2024-03-01 | Oreal | Composition pour la décoloration et la coloration simultanées des fibres kératiniques et procédé mettant en œuvre cette composition |
FR3117808B1 (fr) | 2020-12-18 | 2024-03-01 | Oreal | Composition pour la décoloration et la coloration simultanées des fibres kératiniques et procédé mettant en œuvre cette composition |
FR3130570A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130567B1 (fr) | 2021-12-16 | 2024-02-16 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130569A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130572A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130568B1 (fr) | 2021-12-16 | 2024-02-16 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130571B1 (fr) | 2021-12-16 | 2024-02-16 | Oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3130610A1 (fr) | 2021-12-20 | 2023-06-23 | L'oreal | Composition comprenant un copolymère polyhydroxyalcanoate à longue chaine hydrocarbonnée à groupe(s) ionique(s), procédé de traitement des matières kératiniques mettant en œuvre la composition |
FR3136967A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3136972A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3136968A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3136966A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3136976A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3136975A1 (fr) | 2022-06-22 | 2023-12-29 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB885046A (en) * | 1958-06-25 | 1961-12-20 | Basf Ag | New cationic azo dyestuffs derived from imidazole and methods for their production and their use |
DE1137815B (de) * | 1958-09-30 | 1962-10-11 | Basf Ag | Verfahren zur Herstellung basischer Azofarbstoffe |
DE1157324B (de) | 1959-10-29 | 1963-11-14 | Basf Ag | Verfahren zur Herstellung basischer Azofarbstoffe |
EP0714954B1 (de) * | 1994-11-03 | 2002-09-25 | Ciba SC Holding AG | Kationische Imidazolazofarbstoffe |
ATE264891T1 (de) * | 2000-03-09 | 2004-05-15 | Ciba Sc Holding Ag | Verfahren zur färbung von haaren unter verwendung von kationischen farbstoffen |
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2001
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- 2001-03-01 CN CN01806132.XA patent/CN1217995C/zh not_active Expired - Fee Related
- 2001-03-01 DE DE60102904T patent/DE60102904T2/de not_active Expired - Lifetime
- 2001-03-01 BR BR0109060-7A patent/BR0109060A/pt not_active Application Discontinuation
- 2001-03-01 ES ES01919361T patent/ES2217131T3/es not_active Expired - Lifetime
- 2001-03-01 CA CA002400337A patent/CA2400337A1/en not_active Abandoned
- 2001-03-01 WO PCT/EP2001/002316 patent/WO2001066646A1/en active IP Right Grant
- 2001-03-01 MX MXPA02008645A patent/MXPA02008645A/es active IP Right Grant
- 2001-03-01 US US10/220,863 patent/US6843256B2/en not_active Expired - Fee Related
- 2001-03-01 EP EP01919361A patent/EP1261666B1/en not_active Expired - Lifetime
- 2001-03-01 JP JP2001565809A patent/JP2003525949A/ja active Pending
- 2001-03-01 AU AU46491/01A patent/AU781845B2/en not_active Ceased
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2004
- 2004-12-08 US US11/007,450 patent/US7060806B2/en not_active Expired - Fee Related
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ES2217131T3 (es) | 2004-11-01 |
CA2400337A1 (en) | 2001-09-13 |
AU781845B2 (en) | 2005-06-16 |
US20030066143A1 (en) | 2003-04-10 |
US6843256B2 (en) | 2005-01-18 |
US7060806B2 (en) | 2006-06-13 |
EP1261666A1 (en) | 2002-12-04 |
ATE264891T1 (de) | 2004-05-15 |
BR0109060A (pt) | 2003-06-03 |
JP2003525949A (ja) | 2003-09-02 |
MXPA02008645A (es) | 2003-02-24 |
US20050091764A1 (en) | 2005-05-05 |
DE60102904D1 (de) | 2004-05-27 |
DE60102904T2 (de) | 2005-03-31 |
CN1217995C (zh) | 2005-09-07 |
EP1261666B1 (en) | 2004-04-21 |
WO2001066646A1 (en) | 2001-09-13 |
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