AU2733399A - Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition - Google Patents
Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition Download PDFInfo
- Publication number
- AU2733399A AU2733399A AU27333/99A AU2733399A AU2733399A AU 2733399 A AU2733399 A AU 2733399A AU 27333/99 A AU27333/99 A AU 27333/99A AU 2733399 A AU2733399 A AU 2733399A AU 2733399 A AU2733399 A AU 2733399A
- Authority
- AU
- Australia
- Prior art keywords
- formula
- para
- amino
- radical
- phenylenediamine
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 238000004043 dyeing Methods 0.000 title claims abstract description 37
- 230000003647 oxidation Effects 0.000 title claims abstract description 25
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 11
- 102000011782 Keratins Human genes 0.000 title claims description 23
- 108010076876 Keratins Proteins 0.000 title claims description 23
- 210000004209 hair Anatomy 0.000 claims abstract description 17
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims abstract description 14
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003929 3-aminopyridines Chemical class 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 52
- -1 alkoxy radical Chemical class 0.000 claims description 40
- 150000003254 radicals Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000002585 base Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical class NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000982 direct dye Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 claims description 3
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 claims description 3
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 3
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 3
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- NKNCGBHPGCHYCQ-UHFFFAOYSA-N (2,5-diaminophenyl)methanol Chemical compound NC1=CC=C(N)C(CO)=C1 NKNCGBHPGCHYCQ-UHFFFAOYSA-N 0.000 claims description 2
- KQGOJGSMIRVVJL-UHFFFAOYSA-N 1-n-methyl-4-n-[4-[4-(methylamino)anilino]butyl]benzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NCCCCNC1=CC=C(NC)C=C1 KQGOJGSMIRVVJL-UHFFFAOYSA-N 0.000 claims description 2
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 2
- ZXZZHWVJHLHSNF-UHFFFAOYSA-N 2-(4-aminoanilino)oxyethanol Chemical compound NC1=CC=C(NOCCO)C=C1 ZXZZHWVJHLHSNF-UHFFFAOYSA-N 0.000 claims description 2
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 claims description 2
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 claims description 2
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 claims description 2
- FXFTWEVIIHVHDS-UHFFFAOYSA-N 2-fluorobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(F)=C1 FXFTWEVIIHVHDS-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 claims description 2
- RGKJLNMYCNSVKZ-UHFFFAOYSA-N 4-amino-2-(methoxymethyl)phenol Chemical compound COCC1=CC(N)=CC=C1O RGKJLNMYCNSVKZ-UHFFFAOYSA-N 0.000 claims description 2
- MXJQJURZHQZLNN-UHFFFAOYSA-N 4-amino-2-fluorophenol Chemical compound NC1=CC=C(O)C(F)=C1 MXJQJURZHQZLNN-UHFFFAOYSA-N 0.000 claims description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 claims description 2
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 2
- POKISONDDBRXBK-UHFFFAOYSA-N 4-n,4-n,2-trimethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N)C(C)=C1 POKISONDDBRXBK-UHFFFAOYSA-N 0.000 claims description 2
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 claims description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims description 2
- UOWYGPTYSRURDP-UHFFFAOYSA-N 4-n,4-n-dipropylbenzene-1,4-diamine Chemical compound CCCN(CCC)C1=CC=C(N)C=C1 UOWYGPTYSRURDP-UHFFFAOYSA-N 0.000 claims description 2
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 claims description 2
- CQPLGGXOAHSQBD-UHFFFAOYSA-N 5-amino-2,4-dimethoxyphenol Chemical compound COC1=CC(OC)=C(O)C=C1N CQPLGGXOAHSQBD-UHFFFAOYSA-N 0.000 claims description 2
- JSCNCRWPXOTDDZ-UHFFFAOYSA-N 5-amino-2-chlorophenol Chemical compound NC1=CC=C(Cl)C(O)=C1 JSCNCRWPXOTDDZ-UHFFFAOYSA-N 0.000 claims description 2
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MUHQJMUYRYHUIW-UHFFFAOYSA-N 5-amino-4-methoxy-2-methylphenol Chemical compound COC1=CC(C)=C(O)C=C1N MUHQJMUYRYHUIW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- BKEFUBHXUTWQED-UHFFFAOYSA-N n-(4-amino-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(O)=C1 BKEFUBHXUTWQED-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- CBWPAXKVACVBLU-UHFFFAOYSA-N 1,3-bis[4-amino-n-(2-hydroxyethyl)anilino]propan-1-ol Chemical compound C1=CC(N)=CC=C1N(CCO)CCC(O)N(CCO)C1=CC=C(N)C=C1 CBWPAXKVACVBLU-UHFFFAOYSA-N 0.000 claims 1
- GYWDRJNSLRPYBQ-UHFFFAOYSA-N 2-[3-[2-(2,5-diaminophenoxy)ethoxymethoxy]propoxy]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(OCCCOCOCCOC=2C(=CC=C(N)C=2)N)=C1 GYWDRJNSLRPYBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- MZQGZBUNWFAKAC-UHFFFAOYSA-N 3-(4-aminoanilino)propan-1-ol Chemical compound NC1=CC=C(NCCCO)C=C1 MZQGZBUNWFAKAC-UHFFFAOYSA-N 0.000 claims 1
- DSGHWUWQVNMCKK-UHFFFAOYSA-N 3-amino-4-methoxy-2-methylphenol Chemical compound COC1=CC=C(O)C(C)=C1N DSGHWUWQVNMCKK-UHFFFAOYSA-N 0.000 claims 1
- MNPLTKHJEAFOCA-UHFFFAOYSA-N 4-amino-3-fluorophenol Chemical compound NC1=CC=C(O)C=C1F MNPLTKHJEAFOCA-UHFFFAOYSA-N 0.000 claims 1
- OOPWJBCZQDTTNE-UHFFFAOYSA-N 4-n-[4-(4-aminoanilino)butyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCCCNC1=CC=C(N)C=C1 OOPWJBCZQDTTNE-UHFFFAOYSA-N 0.000 claims 1
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 1
- 101001056473 Homo sapiens Keratin, type II cytoskeletal 5 Proteins 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000003927 aminopyridines Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 102000057575 human KRT5 Human genes 0.000 claims 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000004040 coloring Methods 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000007792 addition Methods 0.000 description 20
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002535 acidifier Substances 0.000 description 3
- 239000002610 basifying agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 description 2
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000004986 phenylenediamines Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- WCKJRVKJTUIAFW-UHFFFAOYSA-N (1-methylpyrazol-3-yl)methanol Chemical compound CN1C=CC(CO)=N1 WCKJRVKJTUIAFW-UHFFFAOYSA-N 0.000 description 1
- RQKQKYICHBSFNX-UHFFFAOYSA-N (4,5-diamino-1-ethylpyrazol-3-yl)methanol Chemical compound CCN1N=C(CO)C(N)=C1N RQKQKYICHBSFNX-UHFFFAOYSA-N 0.000 description 1
- DPTWQNJCRFZYPL-UHFFFAOYSA-N (4,5-diamino-1-propan-2-ylpyrazol-3-yl)methanol Chemical compound CC(C)N1N=C(CO)C(N)=C1N DPTWQNJCRFZYPL-UHFFFAOYSA-N 0.000 description 1
- RZICEOJUAFHYFO-UHFFFAOYSA-N 1-hydroperoxyhexane Chemical compound CCCCCCOO RZICEOJUAFHYFO-UHFFFAOYSA-N 0.000 description 1
- MOGQNVSKBCVIPW-UHFFFAOYSA-N 1-methylpyrazol-3-amine Chemical compound CN1C=CC(N)=N1 MOGQNVSKBCVIPW-UHFFFAOYSA-N 0.000 description 1
- YMRBWWVXSSYSGH-UHFFFAOYSA-N 1-methylpyrazole-3,4,5-triamine Chemical compound CN1N=C(N)C(N)=C1N YMRBWWVXSSYSGH-UHFFFAOYSA-N 0.000 description 1
- WXFKWEVAPSWLOI-UHFFFAOYSA-N 1h-pyrazole-3,4,5-triamine Chemical compound NC1=NNC(N)=C1N WXFKWEVAPSWLOI-UHFFFAOYSA-N 0.000 description 1
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical compound NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 description 1
- BRMHZFZMBVIHMO-UHFFFAOYSA-N 2,5-dimethylpyrazole-3,4-diamine Chemical compound CC1=NN(C)C(N)=C1N BRMHZFZMBVIHMO-UHFFFAOYSA-N 0.000 description 1
- MRQOOXQWSNRMAM-UHFFFAOYSA-N 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC(C)=NC2=C(N)C(C)=NN21 MRQOOXQWSNRMAM-UHFFFAOYSA-N 0.000 description 1
- VFFKUMJVZWLOQM-UHFFFAOYSA-N 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=C(C)C=NC2=C(N)C(C)=NN21 VFFKUMJVZWLOQM-UHFFFAOYSA-N 0.000 description 1
- LGZOJZFHAJJLCF-UHFFFAOYSA-N 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound CC1=CC(N)=NC2=C(N)C(C)=NN21 LGZOJZFHAJJLCF-UHFFFAOYSA-N 0.000 description 1
- RHIPXPBQVGXJNL-UHFFFAOYSA-N 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound OCCNC1=CC=NC2=C(N)C=NN21 RHIPXPBQVGXJNL-UHFFFAOYSA-N 0.000 description 1
- ZQLZWNDBBQUIEY-UHFFFAOYSA-N 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol Chemical compound NC1=CC=NC2=C(N(CCO)CCO)C=NN12 ZQLZWNDBBQUIEY-UHFFFAOYSA-N 0.000 description 1
- HARBPHQCTIDSBX-UHFFFAOYSA-N 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)amino]ethanol Chemical compound NC1=CC=NC2=C(NCCO)C=NN12 HARBPHQCTIDSBX-UHFFFAOYSA-N 0.000 description 1
- MLXCINPNVUJSHY-UHFFFAOYSA-N 2-[2-hydroxyethyl-(2-methylanilino)amino]ethanol Chemical compound CC1=CC=CC=C1NN(CCO)CCO MLXCINPNVUJSHY-UHFFFAOYSA-N 0.000 description 1
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 1
- AOJAOISKDDBFNM-UHFFFAOYSA-N 2-amino-4H-pyrazolo[1,5-a]pyrimidin-5-one Chemical compound NC1=NN2C(N=C(C=C2)O)=C1 AOJAOISKDDBFNM-UHFFFAOYSA-N 0.000 description 1
- AJZRIOLJTXDFDY-UHFFFAOYSA-N 2-benzyl-5-methylpyrazole-3,4-diamine Chemical compound NC1=C(N)C(C)=NN1CC1=CC=CC=C1 AJZRIOLJTXDFDY-UHFFFAOYSA-N 0.000 description 1
- LRFYRWUMJLXTJH-UHFFFAOYSA-N 2-ethyl-5-(4-methoxyphenyl)pyrazole-3,4-diamine Chemical compound NC1=C(N)N(CC)N=C1C1=CC=C(OC)C=C1 LRFYRWUMJLXTJH-UHFFFAOYSA-N 0.000 description 1
- MEKRUGGNBTYVRV-UHFFFAOYSA-N 2-ethyl-5-methylpyrazole-3,4-diamine Chemical compound CCN1N=C(C)C(N)=C1N MEKRUGGNBTYVRV-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- LYEBIHUMFJCIMG-UHFFFAOYSA-N 2-methyl-5-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)N(C)N=C1C1=CC=CC=C1 LYEBIHUMFJCIMG-UHFFFAOYSA-N 0.000 description 1
- CTGVWWNOCSCKKI-UHFFFAOYSA-N 2-tert-butyl-5-methylpyrazole-3,4-diamine Chemical compound CC1=NN(C(C)(C)C)C(N)=C1N CTGVWWNOCSCKKI-UHFFFAOYSA-N 0.000 description 1
- ISWQUCOYLGAJSI-UHFFFAOYSA-N 3-(4-aminoanilino)-1-[[4-amino-4-(2-hydroxyethyl)cyclohexa-1,5-dien-1-yl]amino]propan-1-ol Chemical compound OCCC1(CC=C(C=C1)NC(CCNC1=CC=C(C=C1)N)O)N ISWQUCOYLGAJSI-UHFFFAOYSA-N 0.000 description 1
- RCXJYACRSIUCGP-UHFFFAOYSA-N 3-n-(2-aminoethyl)-2,5-dimethylpyrazole-3,4-diamine Chemical compound CC1=NN(C)C(NCCN)=C1N RCXJYACRSIUCGP-UHFFFAOYSA-N 0.000 description 1
- ZQBHGSSAKLGUBH-UHFFFAOYSA-N 4,5,6-triamino-1h-pyrimidin-2-one Chemical compound NC1=NC(=O)NC(N)=C1N ZQBHGSSAKLGUBH-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- GMIOEEOCQXVIAM-UHFFFAOYSA-N 4-amino-2-(dodecylamino)-4-oxobutanoic acid Chemical compound CCCCCCCCCCCCNC(C(O)=O)CC(N)=O GMIOEEOCQXVIAM-UHFFFAOYSA-N 0.000 description 1
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 description 1
- VGNTUDBFWCGMGV-UHFFFAOYSA-N 4-n,1-dimethylpyrazole-3,4,5-triamine Chemical compound CNC=1C(N)=NN(C)C=1N VGNTUDBFWCGMGV-UHFFFAOYSA-N 0.000 description 1
- OAQDBKQAJRFJIY-UHFFFAOYSA-N 4-n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]-4-n-ethyl-2-methylbenzene-1,4-diamine Chemical compound C=1C=C(N)C(C)=CC=1N(CC)CCN(CC)C1=CC=C(N)C(C)=C1 OAQDBKQAJRFJIY-UHFFFAOYSA-N 0.000 description 1
- DMBUAGDHNUPLRA-UHFFFAOYSA-N 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=C(C)C(C)=NC2=C(N)C=NN21 DMBUAGDHNUPLRA-UHFFFAOYSA-N 0.000 description 1
- CMYXTZPTHYRATM-UHFFFAOYSA-N 5-hydrazinyl-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(NN)=C1N CMYXTZPTHYRATM-UHFFFAOYSA-N 0.000 description 1
- JSVCLRZBHIRDNZ-UHFFFAOYSA-N 5-methyl-2-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)C(C)=NN1C1=CC=CC=C1 JSVCLRZBHIRDNZ-UHFFFAOYSA-N 0.000 description 1
- CGTQMHXEGLHVFE-UHFFFAOYSA-N 5-methyl-2-propan-2-ylpyrazole-3,4-diamine Chemical compound CC(C)N1N=C(C)C(N)=C1N CGTQMHXEGLHVFE-UHFFFAOYSA-N 0.000 description 1
- WEPOCTWSRWLQLL-UHFFFAOYSA-N 6-methoxypyridine-2,3-diamine Chemical compound COC1=CC=C(N)C(N)=N1 WEPOCTWSRWLQLL-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZWJGDIYLCVZUMF-UHFFFAOYSA-N NC1=NN2C(N=CC=C2O)=C1 Chemical compound NC1=NN2C(N=CC=C2O)=C1 ZWJGDIYLCVZUMF-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 description 1
- 229960004012 amifampridine Drugs 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 102000005936 beta-Galactosidase Human genes 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- BXTQPQKBKVCRPT-UHFFFAOYSA-N n-[2-(4-aminoanilino)oxyethyl]acetamide Chemical compound CC(=O)NCCONC1=CC=C(N)C=C1 BXTQPQKBKVCRPT-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- FFNJDUZBKSGSIV-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound C1=CC(N)=NC2=C(N)C=NN21 FFNJDUZBKSGSIV-UHFFFAOYSA-N 0.000 description 1
- PNFZIEOWPDFJBH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C=NN21 PNFZIEOWPDFJBH-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention concerns an oxidation dyeing composition for keratinous fibres, and in particular human keratinous fibres such as hair comprising, in a suitable dyeing medium, at least an oxidation base, at least a 3-aminopyridine derivative as direct colouring agent, and at least a substituted meta-aminophenol as coupling agent, as well as a dyeing method using said composition.
Description
1 COMPOSITION FOR THE OXIDATION DYEING OF KERATIN FIBRES AND DYEING PROCESS USING THIS COMPOSITION The invention relates to a composition for 5 the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing, at least one oxidation base, at least one 3-aminopyridine derivative as direct dye, and at least 10 one substituted meta-aminophenol as coupler, as well as to the dyeing process using this composition. It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular 15 ortho- or para-phenylenediamines, ortho- or para aminophenols and heterocyclic bases, which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with 20 oxidizing products, can give rise to coloured compounds and dyes by a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or colour modifiers, the latter 25 being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
2 The variety of molecules used as regards the oxidation bases and couplers allows a wide range of colours to be obtained. It is also known that, in order to vary the 5 shades obtained even more and to give them glints, it is possible to use, in combination with the oxidation dye precursors and couplers, direct dyes, i.e. coloured substances which provide a coloration in the absence of an oxidizing agent. 10 The great majority of these direct dyes belong to the family of nitrobenzene compounds and have the drawback, when they are incorporated into dye compositions, of leading to colorations that are not sufficiently fast, in particular with respect to 15 shampoos. The so-called "permanent" coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must be able to give shades of the desired intensity and it must be 20 able to withstand external agents (light, bad weather, washing, permanent-waving, perspiration and rubbing). The dyes must also make it possible to cover white hair, and, finally, they must be as unselective as possible, i.e. they must give the smallest possible 25 differences in colour all the way along the same keratin fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
3 Compositions for the oxidation dyeing of keratin fibres containing a combination of a benzenic oxidation base, a direct dye of the 3-aminopyridine family and an unsubstituted meta-aminophenol as coupler 5 have already been proposed, in particular in patent application FR-A-2,285,851. However, the colorations obtained using such compositions are not entirely satisfactory, in particular from the point of view of their chromaticity and their fastness. 10 The Applicant has now discovered that it is possible to obtain novel dyes which are capable of giving intense and chromatic colorations, which show little selectivity and which satisfactorily withstand the various attacking factors to which the fibres may 15 be subjected, by combining at least one oxidation base, at least one suitably selected 3-aminopyridine derivative as direct dye, and at least one suitably selected meta-aminophenol derivative. This discovery forms the basis of the present 20 invention. A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, characterized in that it comprises, in a medium 25 which is suitable for dyeing: - at least one oxidation base, 144 4 - as direct dye, at least one 3-aminopyridine derivative chosen from the compounds of formula (I) below:
R
2 NN / -A (I) RR B43 5 in which: - B represents a group of formula (Ia) or (Ib) below: NN | (1a) X (ib) 0~ R - R represents a Ci-C 4 alkyl radical; - R 1 represents a hydrogen or halogen atom such as 10 chlorine, bromine or fluorine, or a Ci-C 4 alkyl or
C
1
-C
4 alkoxy radical; - R 2 represents a hydrogen atom or a Ci-C 4 alkyl or Ci-C 4 alkoxy radical; - R 4 represents a hydrogen or halogen atom such as 15 chlorine, bromine or fluorine, or a C 1
-C
4 alkyl, nitro, amino or (Ci-C 4 )acylamino radical; - R 3 represents a hydrogen atom or else R 4 and R 3 together form a 6-membered unsaturated ring bearing a hydroxyl substituent chelated with one of the 20 nitrogen atoms of the azo double bond; 5 - A represents a residue -NR 5
R
6 in which R 5 represents a hydrogen atom or a Ci-C 4 alkyl, Ci-C 4 monohydroxyalkyl or C 2
-C
4 polyhydroxyalkyl radical; R 6 represents a hydrogen atom, a Ci-C 4 alkyl, Ci-C 4 monohydroxyalkyl or 5 C 2
-C
4 polyhydroxyalkyl radical, a phenyl ring or a
-CH
2
-SO
3 Na radical; - X- represents a monovalent or divalent anion and is preferably chosen from a halogen atom such as chlorine, bromine, fluorine or iodine, a hydroxide, a 10 hydrogen sulphate or a (Ci-C 6 )alkyl sulphate such as, for example, a methyl sulphate or an ethyl sulphate, and - at least one coupler chosen from the meta-aminophenol derivatives of formula (II) below, and the addition 15 salts thereof with an acid: OH
NHR
7 Ra in which: - R 7 represents a hydrogen atom or a Ci-C 4 alkyl, CI-C 4 monohydroxyalkyl, C 2
-C
4 polyhydroxyalkyl or C 1
-C
4 20 monoaminoalkyl radical; - R 8 represents a hydrogen atom, a Ci-C 4 alkyl or Ci-C 4 alkoxy radical or a halogen atom chosen from chlorine, bromine and fluorine, 6 - R 9 and R' 9 , which may be identical or different, represent a hydrogen or halogen atom or a C 1
-C
4 alkyl,
C
1
-C
4 alkoxy,
C
1 -C4 monohydroxyalkyl,
C
2
-C
4 polyhydroxyalkyl,
C
1
-C
4 monohydroxyalkoxy or C 2
-C
4 5 polyhydroxyalkoxy radical; it being understood that at least one of the radicals
R
7 , R 8 , R 9 and R' 9 is other than a hydrogen atom. The dye composition in accordance with the invention gives intense, chromatic colorations which 10 show little selectivity and excellent properties of resistance both with respect to atmospheric agents such as light and bad weather, and with respect to perspiration and the various treatments to which the hair may be subjected. These properties are 15 particularly noteworthy as regards the chromaticity. A subject of the invention is also a process for the oxidation dyeing of keratin fibres using this dye composition. The nature of the oxidation base(s) used in 20 the ready-to-use dye composition is not critical. They can be chosen, in particular, from para phenylenediamines, double bases, para-aminophenols, ortho-aminophenols and heterocyclic oxidation bases. Among the para-phenylenediamines which can be 25 used as oxidation base in the dye compositions in accordance with the invention, mention may be made in particular of the compounds of formula (III) below, and the addition salts thereof with an acid: 7
NR
0
R
1 . R1
NH
2 in which: - Rio represents a hydrogen atom or a Ci-C 4 alkyl radical,
C
1
-C
4 monohydroxyalkyl radical,
C
2
-C
4 5 polyhydroxyalkyl radical, (Ci-C 4 )alkoxy(Ci-C 4 )alkyl radical, Ci-C 4 alkyl radical substituted with a nitrogenous group, phenyl or 4'-aminophenyl; - R 11 represents a hydrogen atom or a Ci-C 4 alkyl radical, Ci-C 4 monohydroxyalkyl radical,
C
2
-C
4 10 polyhydroxyalkyl radical, (Ci-C 4 )alkoxy(C 1
-C
4 )alkyl radical or Ci-C 4 alkyl radical substituted with a nitrogenous group; - R 12 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, or a 15 Ci-C 4 alkyl radical,
C
1
-C
4 monohydroxyalkyl radical,
C
1
-C
4 hydroxyalkoxy radical, acetylamino (Ci-C 4 ) alkoxy, mesylamino (C 1
-C
4 ) alkoxy or carbamoylamino (Ci - C 4 ) alkoxy radical, - R 13 represents a hydrogen or halogen atom or a C 1
-C
4 20 alkyl radical. Among the nitrogenous groups of formula (III) above, mention may be made in particular of amino, mono(Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, 8 tri (C 1
-C
4 )alkylamino, monohydroxy(Ci-C 4 ) alkylamino, imidazolinium and ammonium radicals. Among the para-phenylenediamines of formula (III) above, mention may be made more particularly of 5 para-phenylenediamine, para-tolylenediamine, 2-chloro para-phenylenediamine, 2,3-dimethyl-para phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para phenylenediamine, N,N-dimethyl-para-phenylenediamine, 10 N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para phenylenediamine, 4 -amino-N,N-diethyl-3-methylaniline, N,N-bis(-hydroxyethyl)-para-phenylenediamine, 4-N,N bis( -hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(p hydroxyethyl)amino-2-chloroaniline, 2-0-hydroxyethyl 15 para-phenylenediamine, 2 -fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(P-hydroxypropyl) para-phenylenediamine, 2-hydroxymethyl-para phenylenediamine, N,N-dimethyl-3-methyl-para phenylenediamine, N-ethyl-N-($-hydroxyethyl)-para 20 phenylenediamine, N- (P,7-dihydroxypropyl) -para phenylenediamine, N-(4'-aminophenyl)-para phenylenediamine, N-phenyl-para-phenylenediamine, 2-p hydroxyethyloxy-para-phenylenediamine, 2-p acetylaminoethyloxy-para-phenylenediamine and N-(1 25 methoxyethyl)-para-phenylenediamine, and the addition salts thereof with an acid. Among the para-phenylenediamines of formula (III) above, the ones most particularly preferred are 9 para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2--hydroxyethyl para-phenylenediamine, 2-p-hydroxyethyloxy-para phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 5 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para phenylenediamine, N,N-bis(P-hydroxyethyl)-para phenylenediamine, 2 -chloro-para-phenylenediamine and 2-p-acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid. 10 According to the invention, the term "double bases" means compounds comprising at least two aromatic nuclei on which amino and/or hydroxyl groups are borne. Among the double bases which can be used as oxidation bases in the dye compositions in accordance 15 with the invention, mention may be made in particular of the compounds corresponding to the formula (IV) below, and the addition salts thereof with an acid: Zz R16 R1 R R 1 7 14 Y|R (i R -- y
-
I (II)
NR
1 8
R
1 9 NRmR 21 in which: 20 - Z, and Z 2 , which may be identical or different, represent a hydroxyl or -NH 2 radical which can be substituted with a C 1
-C
4 alkyl radical or with a linker arm Y; 10 - the linker arm Y represents a linear or branched alkylene chain comprising from 1 to 14 carbon atoms, which can be interrupted or terminated with one or more nitrogenous groups and/or with one or more 5 hetero atoms such as oxygen, sulphur or nitrogen atom , and optionally substituted with one or more hydroxyl or C1-C 6 alkoxy radicals; - R 1 4 and R 15 represent a hydrogen or halogen atom, a
C
1
-C
4 alkyl radical, Ci-C 4 monohydroxyalkyl radical, 10 C 2
-C
4 polyhydroxyalkyl radical or C 1
-C
4 aminoalkyl radical or a linker arm Y; - R 16 , R17, R 18 , R 19 , R 2 0 and R 2 1 , which may be identical or different, represent a hydrogen atom, a linker arm Y or a Ci-C 4 alkyl radical; 15 it beir g understood that the compounds of formula (IV) comprise only one linker arm Y per molecule. Among the nitrogenous groups of formula (IV) above, mention may be made in particular of amino, mono (Ci - C 4 ) alkylamino, di (Ci-C 4 )alkylamino, 20 tri (Ci- 4 )alkylamino, monohydroxy (Ci - C 4 ) alkylamino, imidazolinium and ammonium radicals. Among the double bases of formula (IV) above, mention may be made more particularly of N,N'-bis(p hydroxy thyl)-N,N'-bis(4'-aminophenyl)-1,3 25 diamino;ropanol, N,N'-bis( -hydroxyethyl)-N,N'-bis(4' aminoph nyl)ethylenediamine, N,N'-bis(4 aminoph nyl) tetramethylenediamine, N,N' -bis (3 K , hydroxy thyl) -N,N' -bis (4-aminophenyl) C 4 11 tetramethylenediamine, N,N' -bis (4 methylaminophenyl) tetramethylenediamine, N,N' bis (ethyl) -N,N' -bis (4' -amino-3' methylphenyl) ethylenediamine and 1, 8-bis (2,5 5 diaminophenoxy)-3,5-dioxaoctane, and the addition salts thereof with an acid. Among these double bases of formula (IV), N,N' -bis (p-hydroxyethyl) -N,N' -bis (4' -aminophenyl) -1,3 diaminopropanol and 1,8-bis(2,5-diaminophenoxy) -3,5 10 dioxaoctane, or one of the addition salts thereof with an acid, are particularly preferred. Among the para-aminophenols which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made in 15 particular of the compounds of formula (V) below, and the addition salts thereof with an acid: OH R23
NH
2 in which: 20 - R 2 2 represents a hydrogen or halogen atom or a Ci-C 4 alkyl, C 1
-C
4 monohydroxyalkyl, (Ci-C4)alkoxy(C 1
-C
4 )alkyl, Ci-C 4 aminoalkyl or hydroxy(C1-C 4 )alkylamino(C 1
-C
4 )alkyl radical, 12 - R 2 3 represents a hydrogen or halogen atom or a Ci-C 4 alkyl, Ci-C 4 monohydroxyalkyl,
C
2
-C
4 polyhydroxyalkyl,
C
1
-C
4 aminoalkyl, cyano(Ci-C 4 )alkyl or (Ci-C 4 )alkoxy(Ci-C 4 )alkyl radical, 5 it being understood that at least one of the radicals
R
2 2 and R 2 3 represents a hydrogen atom. Among the para-aminophenols of formula (V) above, mention may be made more particularly of para aminophenol, 4 -amino-3-methylphenol, 4-amino-3 10 fluorophenol, 4 -amino-3-hydroxymethylphenol, 4-amino-2 methylphenol, 4 -amino-2-hydroxymethylphenol, 4-amino-2 methoxymethylphenol, 4 -amino-2-aminomethylphenol, 4 amino-2-(p-hydroxyethylaminomethyl)phenol and 4-amino 2-fluorophenol, and the addition salts thereof with an 15 acid. Among the ortho-aminophenols which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of 2-aminophenol, 2 -amino-5-methylphenol, 20 2 -amino-6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid. Among the heterocylic bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more 25 particularly of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives, and the addition salts thereof with an acid.
13 Among the pyridine derivatives, mention may be made more particularly of the compounds described, for example, in GB patents 1,026,978 and 1,153,196, such as 2-5-diaminopyridine, 2-(4-methoxyphenyl)amino 5 3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(p methoxyethyl)amino-3-amino-6-methoxypyridine and 3,4 diaminopyridine, and the addition salts thereof with an acid. Among the pyrimidine derivatives, mention may 10 be made more particularly of the compounds described, for example, in German patent DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-333,495 or patent applications WO 96/15765, such as 2,4,5,6 tetraaminopyrimidine, 4-hydroxy-2,5,6 15 triaminopyrimidine, 2-hydroxy-4,5,6--triaminopyrimidine, 2
,
4 -dihydroxy-5,6-diaminopyrimidine and 2,5,6 traminopyrimidine, and pyrazolopyrimidine derivatives, such as those mentioned in patent application FR-A-2,750,048 and among which mention may be made of 20 pyrazolo[1,5-a]pyrimidine-3,7-diamine; 2,5 dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; pyrazolo[1,5-a]pyrimidine-3,5-diamine; 2,7 dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; 3 aminopyrazolo[1,5-a]pyrimidin-7-ol; 3 25 aminopyrazolo[1,5-a]pyrimidin-5-ol; 2-(3 aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7 aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3 aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2 &44 14 hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5 a]pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol, 5,6 dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6 dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and 2,5, 5 N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists, and the addition salts thereof with an acid. Among the pyrazole derivatives, mention may 10 be made more particularly of the compounds described in patents DE 3,843,892 and DE 4,133,957 and patent applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988, such as 4,5-diamino-l methylpyrazole, 3,4-diaminopyrazole, 4,5-diamino-l-(4' 15 chlorobenzyl)pyrazole, 4,5-diamino-1,3 dimethylpyrazole, 4,5-diamino-3-methyl-1 phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5 diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-l 20 methylpyrazole, 4,5-diamino-l-tert-butyl-3 methylpyrazole, 4,5-diamino-l-(p-hydroxyethyl)-3 methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5 diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3 25 hydroxymethyl-1-methylpyrazole, 4,5-diamino-3 hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3 methyl-1-isopropylpyrazole, 4-amino-5-(2' aminoethyl)amino-1,3-dimethylpyrazole, 15 3,4,5-triaminopyrazole, 1-methyl-3,4,5 triaminopyrazole, 3, 5-diamino-l-methyl-4 methylaminopyrazole and 3,5-diamino-4-(3 hydroxyethyl) amino-1-methylpyrazole, and the addition 5 salts thereof with an acid. The oxidation base(s) preferably represent(s) from 0.0005 to 12% by weight approximately relative to the total weight of the dye composition in accordance with the invention, and even more preferably from 0.005 10 to 6% by weight approximately relative to this weight. The 3-aminopyridine derivative(s) of formula (I) in accordance with the invention is (are) preferably chosen from: - 4'-dimethylaminobenzene-1'-azo-l-methyl-3-pyridinium 15 methosulphate of formula: CH3
CH
3
,CH
3 S0 4 ' N N N
CH
3 - 4'-bis( -hydroxyethyl)aminobenzene-1'-azo-1-methyl-3 pyridinium methosulphate of formula: 16
CH
2
CH
2 OH
CH
2
CH
2 OH
,CH
3
SO
4
I
CH
3 - 4' -amino-8' -hydroxynaphthalene-l' -azo-l-methyl-3 pyridinium methosulphate of formula:
NH
2 N
,CH
3 S0 4 N HO
CH
3 5 - 4' -dimethylamino-2' -nitrobenzene-1' -azo-l-methyl-3 pyridinium methosulphate of formula: CH3
CH
3 ,CH 3
SO
4 N IN N. -NO2
CH
3 - 4' -dimethylaminobenzene-l' -azo-1, 6-dimethyl-3 pyridinium methosulphate of formula: 17
CH
3 N NCH3 CH3SO4 N
H
3 C N
CH
3
-
4 1 -aminobenzeie-1'-azo-3-pyridine N-oxide of formula:
NH
2 N N 0~ - 4' -dimethylaminobenzene -1' -azo-3-pyridine N-oxide of 5 formula:
CH
3 CrH N
-
4 '-N,N-bis(-hydroxyethyl)aminobenzene -l'-azo-3 pyridine N-oxide of formula: 44/ 18
CH
2
CH
2 OH N
CH
2
CH
2 OH ( N N - 4' -dimethylamino-2' -methylbenzene-l' -azo-1-ethyl-3 pyridinium ethosulphate of formula: CH3 NI ~CH 3 , C 2
H
5
S
4 NN OH NN
C
2
H
5 5 - 4' -dimethylamino-2' -methylbenzene-l' -azo-1-butyl-3 pyridinium bromide of formula:
CH
3 N C3 ,Br' N C4H9 - 4' -dimethylamino-2' -chlorobenzene-l' -azo-1-methyl-3 pyridinium methosulphate of formula: 19
CH
3 ~1
CH
3 ,CH 3 S0 4 N NCI N CH3 - 2' 1,4' -diamino-5' -methylbenzene-' -azo-1-methyl-3 pyridinium methosulphate of formula: CHa
NH
2
CH
3 SO4' N NH + 2 N
CH
3 5 - 4' -phenylaminobenzene-l' -azo-l-methyl-3-pyridinium methosulphate of formula: H N N , CH 3
SO
4 N. N N
CH
3 - 2' -acetylamino-4' -dimethylaminobenzene-l' -azo-l ethyl-3-pyridinium ethosulphate of formula: 20
CH
3 N Na , C 2 H S0 4 N
NHCOCH
3 N - 2',4'-diamino-5'-methoxybenzene-1'-azo-l-methyl-3 pyridinium methosulphate of formula:
OCH
3
NH
2 , CH 3
SO
4 N + -
NH
2 N
CH
3 5 and - 2'-amino-4'-dimethylaminobenzene-1'-azo-l-methyl-3 pyridinium methosulphate of formula:
CH
3 N
SNH
2 N NN
CH
3 The 3-aminopyridine derivative(s) of formula (eRAI) u -0 (1) used according to the invention preferably 21 represent(s) from 0.001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.01 to 5% by weight approximately relative to this weight. 5 Among the meta-aminophenols of formula (II) above, mention may be made more particularly of 5 amino-2-methoxyphenol, 5-amino-2-(p hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-($ hydroxyethyl)amino-2-methylphenol, 5-N-($ 10 hydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino-4 methoxy-2-methylphenol, 5-amino-4-chloro-2 methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(y hydroxypropylamino)-2-methylphenol, 3-amino-2-chloro-6 methylphenol, 3-amino-6-chlorophenol and 3-(P 15 aminoethyl)amino-6-chlorophenol, and the addition salts thereof with an acid. The meta-aminophenol derivative(s) of formula (II) in accordance with the invention preferably represent(s) from 0.0001 to 10% by weight approximately 20 relative to the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately relative to this weight. The dye composition in accordance with the invention can also contain one or more couplers other 25 than the meta-aminophenol derivatives of formula (II) and/or one or more direct dyes other than the 3-aminopyridine derivatives of formula (I), in 3~ 22 particular to modify the shades or to enrich them with glints. Among the couplers which may also be present in the dye composition in accordance with the 5 invention, mention may be made in particular of meta phenylenediamines, meta-diphenols and heterocyclic couplers, and the addition salts thereof with an acid. When they are present, these additional couplers preferably represent from 0.0001 to 10% by 10 weight approximately relative to the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately relative to this weight. In general, the addition salts with an acid which can be used in the context of the dye 15 compositions of the invention (oxidation bases and couplers) are chosen in particular from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates. The medium which is suitable for dyeing (or 20 support) for the dye composition in accordance with the invention generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which would not be sufficiently soluble in water. Organic solvents which may be mentioned, for 25 example, are C 1
-C
4 alkanols, such as ethanol and isopropanol. The solvents can be present in proportions preferably of between 1 and 40% by weight approximately 7 1
>'.
23 relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately. The pH of the dye composition in accordance 5 with the invention is generally between 3 and 12 approximately, and preferably between 5 and 12 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used for dyeing keratin fibres. 10 Among the acidifying agents which may be mentioned, for example, are inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric aci-d or lactic acid, and 15 sulphonic acids. Among the basifying agents which may be mentioned, for example, are aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine, 2 -methyl-2-aminopropanol and 20 derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (VI) below: R24
R
2 6 N-W-N (VI)
R
2 5 F in which W is a propylene residue optionally substituted with a hydroxyl group or a C 1
-C
4 alkyl 25 radical;
R
2 4 , R 25 , R 26 and R 2 7 , which may be identical or AT O 24 different, represent a hydrogen atom or a C 1
-C
4 alkyl or
C
1
-C
4 hydroxyalkyl radical. The dye composition in accordance with the invention can also contain various adjuvants 5 conventionally used in compositions for dyeing the hair. Needless to say, a person skilled in the art will take care to select this or these optional additional compounds such that the advantageous 10 properties intrinsically associated with the dye composition in accordance with the invention are not, or are not substantially, adversely affected by the addition or additions envisaged. The dye composition in accordance with the 15 invention can be in various forms, such as in the form of liquids, creams or gels, which are optionally pressurized, or in any other form which is suitable for dyeing keratin fibres, and in particular human hair. A subject of the invention is also a process 20 for dyeing keratin fibres, and in particular human keratin fibres such as the hair, using the dye composition as defined above. According to this process, the dye composition as defined above is applied to the fibres, 25 the colour being developed at acidic, neutral or alkaline pH with the aid of an oxidizing agent which is added to the dye composition only at the time of use, or which is present in an oxidizing composition that is 25 applied simultaneously or sequentially in a separate manner. According to a particularly preferred embodiment of the dyeing process according to the 5 invention, the dye composition described above is mixed, at the time of use, with an oxidizing composition containing, in a medium which is suitable for dyeing, at least one oxidizing agent present in an amount which is sufficient to develop a coloration. The 10 mixture obtained is then applied to the keratin fibres and is left on them for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which the fibres are rinsed, washed with shampoo, rinsed again and dried. 15 The oxidizing agent present in the oxidizing composition as defined above can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibres, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali 20 metal bromates, persalts such as perborates, percarbonates and persulphates, peracids, enzymes such as 2-electron oxidoreductases, peroxidases and lactases. Hydrogen peroxide is particularly preferred. The pH of the oxidizing composition 25 containing the oxidizing agent as defined above is such that, after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between 3 and 12 approximately and 26 even more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used for dyeing keratin fibres and are as defined above. 5 The oxidizing composition as defined above can also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above. The composition which is finally applied to 10 the keratin fibres can be in various forms, such as in the form of liquids, creams or gels or in any other form which is suitable for dyeing keratin fibres, and in particular human hair. Another subject of the invention is a multi 15 compartment dyeing device or multi-compartment dyeing "kit", or any other multi-compartment packaging system, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition as defined 20 above. These devices may be equipped with a means for applying the desired mixture to the hair, such as the devices described in patent FR-2,586,913 in the name of the Applicant. The examples which follow are intended to 25 illustrate the invention without thereby limiting its scope. -7 'Ar 27 EXAMPLES COMPARATIVE DYEING EXAMPLES 1 TO 4 The dye compositions below were prepared 5 (contents in grams): EXAMPLE 1 2(*) 3 4(*) 4'-Dimethylaminobenzene-1'- 0.5 0.5 azo-3-pyridine N-oxide (compound of formula (I)) 2'-Acetylamino-4'-dimethyl- - - 0.6 0.6 aminobenzene-1'-azo-1-ethyl 3-pyridinium ethosulphate (compound of formula (I)) para--Phenylenediamine 0.324 0.324 0.324 0.324 (oxidation base) 5-Amino-2-methylphenol 0.369 - 0.369 (coupler of formula (II)) meta-Aminophenol (coupler) - 0.327 - 0.327 Common dye support (**) (**) (** Demineralized water qs 100 g 100 g 100 g 100 g (*): Comparative example not forming part of the invention 10 (**) Common dye support: "441 28 -Oleyl alcohol polyglycerolated with 2 mol of glycerol 4.0 g -Oleyl alcohol polyglycerolated with 4 mol of glycerol, containing 78% active material (A.M.) 5.69 g A.M. -Oleic acid 3.0 g -Oleylamine containing 2 mol of ethylene oxide, sold under the trade name Ethomeen 012* by the company Akzo 7.0 g -Diethylaminopropyl laurylaminosuccinamate, sodium salt, containing 55% A.M. 3.0 g A.M. -Oleyl alcohol 5.0 g -Oleic acid diethanolamide 12.0 g -Propylene glycol 3.5 g -Ethyl alcohol 7.0 g -Dipropylene glycol 0.5 g -Propylene glycol monomethyl ether 9.0 g -Sodium metabisulphite as an aqueous solution containing 35% A.M. 0.455 g A.M. -Ammonium acetate 0.8 g -Antioxidant, sequestering agent qs -Fragrance, preserving agent qs -Aqueous ammonia containing 20% NH 3 10.0 g Each of the dye compositions described above was mixed, at the time of use, with an equivalent 44/)4) 29 weight-amount of 2 0-volumes hydrogen peroxide (6% by weight) having a pH of about 3. Each resulting mixture had a pH of about 10+0.2 and was applied for 30 minutes to locks of 5 permanent-waved grey hair containing 90% white hairs. The hair was then rinsed with water, washed with a standard shampoo, rinsed again and then dried. The colour of the locks was evaluated before and after dyeing, in the Munsell system, using a 10 Minolta CM 2002* spectrophotometer. According to the Munsell notation, a colour is defined by the formula: HV / C in which the three parameters denote, respectively, the 15 "Hue" or shade (H), the "Value" or intensity (V) and the "Chroma" or saturation (C), the oblique line simply being a convention and not denoting a ratio. The increase in the coloration AE can be calculated by applying the Nickerson equation: 20 AE = 0.4CodH + 6dV + 3dC as described, for example, in "Journal of the Optical Society of America", vol. 34, No. 9, Sept 1944, pages 25 550-570. In this equation, AE represents the difference in colour between two locks (in the present co case the increase in the coloration), dH, dV and dC 4)4j 30 represent the variation in absolute value of the three parameters H, V and C, Co representing the saturation of the lock relative to which it is desired to evaluate the difference in colour. 5 The greater the value of AE, the greater the difference in colour between the two locks, and, in the present case, the greater the increase in the coloration (or intensity of the coloration). The results are given in the table below: 10 Example Colour of the Colour of Increase in lock the lock coloration before dyeing after dyeing dH dV dC AE 1 3 Y 5.8/1.6 6.5 R 2.7/3.8 16.8 3.1 2.2 36.0 2(*) 3.3 Y 5.8/1.6 1.2 YR 2.4/2.1 12.1 3.4 0.5 29.6 3 3.3 Y 5.8/1.6 5.1 R 2.5/3.0 18.2 3.3 1.4 35.6 4 (*) 3.3 Y 5.8/1.6 8.7 R 2.2/1.5 14.6 3.6 0.1 31.2 (*) Comparative example not forming part of the invention 15 It is found that the dye compositions of Examples 1 and 3 in accordance with the invention, i.e. compositions containing a combination of a direct dye of formula (I), an oxidation base and a coupler of formula (II), lead to more intense colorations than the 1 0 dye compositions of Examples 2 and 4 not forming part 4) N' - 31 of the invention since they contain an unsubstituted coupler of meta-aminophenol type and as described, for example, in patent application FR-A-2,285,851.
Claims (25)
1. Composition for the oxidation dyeing of keratin fibres, and in particular of human keratin 5 fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing: - at least one oxidation base, - as direct dye, at least one 3 -aminopyridine derivative chosen from the compounds of formula (I) 10 below: R2 N=N / A (I) R 1 B R, B R4 Ra in which: - B represents a group of formula (Ia) or (Ib) below: N I . (I) N X (1b) R 15 - R represents a C 1 -C 4 alkyl radical; - R 1 represents a hydrogen or halogen atom such as chlorine, bromine or fluorine, or a C 1 -C 4 alkyl or C 1 -C 4 alkoxy radical; - R 2 represents a hydrogen atom or a C 1 -C 4 alkyl or C 1 -C 4 20 alkoxy radical; C) 33 - R 4 represents a hydrogen or halogen atom such as chlorine, bromine or fluorine, or a C 1 -C 4 alkyl, nitro, amino or (Ci-C 4 )acylamino radical; - R 3 represents a hydrogen atom or else R 4 and R 3 5 together form a 6-membered unsaturated ring bearing a hydroxyl substituent chelated with one of the nitrogen atoms of the azo double bond; - A represents a residue -NR 5 R 6 in which R 5 represents a hydrogen atom or a C 1 -C 4 alkyl, C 1 -C 4 monohydroxyalkyl 10 or C 2 -C 4 polyhydroxyalkyl radical; R 6 represents a hydrogen atom, a Ci-C 4 alkyl, C 1 -C4 monohydroxyalkyl or C 2 -C 4 polyhydroxyalkyl radical, a phenyl ring or a -CH 2 -SO 3 Na radical; - X~ represents a monovalent or divalent anion and is 15 preferably chosen from a halogen atom such as chlorine, bromine, fluorine or iodine, a hydroxide, a hydrogen sulphate or a (C 1 -C 6 )alkyl sulphate such as, for example, a methyl sulphate or an ethyl sulphate, and 20 - at least one coupler chosen from the meta-aminophenol derivatives of formula (II) below, and the addition salts thereof with an acid: OH R9 R1 NHR 7 in which: RA4) 34 - R 7 represents a hydrogen atom or a Ci-C 4 alkyl, C 1 -C 4 monohydroxyalkyl, C 2 -C4 polyhydroxyalkyl or C 1 -C 4 monoaminoalkyl radical; - R 8 represents a hydrogen atom, a C 1 -C 4 alkyl or Ci-C 4 5 alkoxy radical or a halogen atom chosen from chlorine, bromine and fluorine, - R 9 and R' 9 , which may be identical or different, represent a hydrogen or halogen atom or a C 1 -C 4 alkyl, C 1 -C 4 alkoxy, Ci-C 4 monohydroxyalkyl, C 2 -C 4 10 polyhydroxyalkyl, C 1 -C 4 monohydroxyalkoxy or C 2 -C 4 polyhydroxyalkoxy radical; it being understood that at least one of the radicals R 7 , R 8 , R 9 and R' 9 is other than a hydrogen atom.
2. Composition according to Claim 1, 15 characterized in that the oxidation base(s) is (are) chosen from para-phenylenediamines, double bases, para aminophenols, ortho-aminophenols and heterocyclic oxidation bases.
3. Composition according to Claim 2, 20 characterized in that the para-phenylenediamines are chosen from the compounds of formula (III) below, and the addition salts thereof with an acid: NR 1 R F 13 () NH 2 in which: 35 - R 10 represents a hydrogen atom or a C 1 -C 4 alkyl radical, C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl radical, (Ci-C 4 )alkoxy(Ci-C 4 )alkyl radical, Ci-C 4 alkyl radical substituted with a 5 nitrogenous group, phenyl or 4'-aminophenyl; - R 11 represents a hydrogen atom or a C 1 -C 4 alkyl radical, C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl radical, (Ci-C 4 )alkoxy(Ci-C 4 )alkyl radical or Ci-C 4 alkyl radical substituted with a 10 nitrogenous group; - R 12 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, or a C 1 -C 4 alkyl radical, Ci-C 4 monohydroxyalkyl radical, C 1 -C 4 hydroxyalkoxy radical, acetylamino (Ci-C 4 ) alkoxy, 15 mesylamino(Ci-C 4 )alkoxy or carbamoylamino (Ci-C 4 ) alkoxy radical, - R 13 represents a hydrogen or halogen atom or a Ci-C 4 alky radical.
4. Composition according to Claim 3, 20 characterized in that the para-phenylenediamines of formula (III) are chosen from para-phenylenediamine, para-tolylenediamine, 2 -chloro-para-phenylenediamine, 2, 3 -dimethyl-para-phenylenediamine, 2,6-dimethyl-para phenylenediamine, 2, 6 -diethyl-para-phenylenediamine, 25 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N diethyl-3-methylaniline, N,N-bis(f-hydroxyethyl)-para 0 36 phenylenediamine, 4-N,N-bis( -hydroxyethyl)amino-2 methylaniline, 4-N,N-bis(P-hydroxyethyl)amino-2 chloroaniline, 2-p-hydrotyethyl-para-phenylenediamine, 2 -fluoro-para-phenylenediamine, 2-isopropyl-para 5 phenylenediamine, N- (-hydroxypropyl) -para phenylenediamine, 2-hydroxymethyl-para phenylenediamine, N,N-dimethyl-3-methyl-para phenylenediamine, N-ethyl-N- ($-hydroxyethyl) -para phenylenediamine, N- (,y-dihydroxypropyl) -para 10 phenylenediamine, N-(4'-aminophenyl)-para phenylenediamine, N-phenyl-para-phenylenediamine, 2- -hydroxyethyloxy-para-phenylenediamine, 2-p -acetylaminoethyloxy-para-phenylenediamine and N- (0 methoxyethyl)-para-phenylenediamine, and the addition 15 salts thereof with an acid.
5. Composition according to Claim 2, characterized in that the double bases are chosen from the compounds of formula (IV) below, and the addition salts thereof with an acid: Zi 7 R 16 R 17 R-R Y R (II) NR 18 R 1 s NR4R 21 20 in which: - Zi and Z 2 , which may be identical or different, represent a hydroxyl or -NH 2 radical which can be 37 substituted with a CI-C 4 alkyl radical or with a linker arm Y; - the linker arm Y represents a linear or branched alkylene chain comprising from 1 to 14 carbon atoms, 5 which can be interrupted or terminated with one or more nitrogenous groups and/or with one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals; 10 - R 1 4 and R 15 represent a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl radical or Ci-C 4 aminoalkyl radical or a linker arm Y; - RI 1 R 17 , R 18 , R 1 9 , R 2 0 and R 2 1 , which may be identical 15 or different, represent a hydrogen atom, a linker arm Y or a C 1 -C 4 alkyl radical; it being understood that the compounds of formula (IV) comprise only one linker arm Y per molecule.
6. Composition according to Claim 5, 20 characterized in that the double bases of formula (IV) are chosen from N,N'-bis( -hydroxyethyl)-N,N'-bis(4' aminophenyl)-1,3-diaminopropanol, N,N'-bis(p hydroxyethyl)-N,N' -bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N' 25 bis(P-hydroxyethyl)-N,N'-bis(4-aminophenyl) tetramethylenediamine, N,N'-bis(4 methylaminophenyl)tetramethylenediamine, N,N' bis (ethyl) -N, N'-bis (4' -amino-3' 4R1 38 methylphenyl) ethylenediamine and 1, 8-bis (2,5 diaminophenoxy) -3, 5-dioxaoctane, and the addition salts thereof with an acid.
7. Composition according to Claim 2, 5 characterized in that para-aminophenols are chosen from the compounds of formula (V) below, and the addition salts thereof with an acid: OH (V) NH 2 in which: 10 - R 2 2 represents a hydrogen or halogen atom or a Ci-C 4 alkyl, Ci-C 4 monohydroxyalkyl, (C1-C 4 )alkoxy(C 1 -C 4 )alkyl, Ci-C 4 aminoalkyl or hydroxy (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl radical, - R 2 3 represents a hydrogen or halogen atom or a C 1 -C 4 15 alkyl, C 1 -C 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, C 1 -C 4 aminoalkyl, cyano (C 1 -C 4 ) alkyl or (Ci-C 4 ) alkoxy (C 1 -C 4 ) alkyl radical, it being understood that at least one of the radicals R 2 2 and R 2 3 represents a hydrogen atom. 20
8. Composition according to Claim 7, characterized in that the para-aminophenols of formula (V) are chosen from para-aminophenol, 4-amino-3 methylphenol, 4 -amino-3-fluorophenol, 4-amino-3 hydroxymethylphenol, 4 -amino-2-methylphenol, 4-amino-2 5 hydroxymethylphenol, 4 -amino-2-methoxymethylphenol, P- 39 4 -amino-2-aminomethylphenol, 4-amino-2-(p hydroxyethylaminomethyl)phenol and 4-amino-2 fluorophenol, and the addition salts thereof with an acid. 5
9. Composition according to Claim 2, characterized in that the ortho-aminophenols are chosen from 2-aminophenol, 2 -amino-5-methylphenol, 2-amino-6 methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid. 10
10. Composition according to Claim 2, characterized in that the heterocyclic oxidation bases are chosen from pyridine derivatives, pyrimidine derivatives and pyrazole derivatives, and the addition salts thereof with an acid. 15
11. Composition according to any one of the preceding claims, characterized in that the oxidation base(s) represent(s) from 0.0005 to 12% by weight relative to the total weight of the dye composition.
12. Composition according to Claim 11, 20 characterized in that the oxidation base(s) represent(s) from 0.005 to 6% by weight relative to the total weight of the dye composition.
13. Composition according to any one of the preceding claims, characterized in that the 3 25 aminopyridine derivative(s) of formula (I) is (are) chosen from: - 4'-dimethylaminobenzene-l'-azo-l-methyl-3-pyridinium methosulphate of formula: 40 CH 3 N N ~CH 3 , CH 3 SO 4 N IN CH 3 - 4' -bis(P-hydroxyethyl)aminobenzene-1' -azo-1-methyl-3 pyridinium methosulphate of formula: CH 2 CH 2 OH NN CH 2 CH 2 OH ,CH 3 SO 4 N N N CH 3 5 - 4'-amino-8'-hydroxynaphthalene-l'-azo-1-methyl-3 pyridinium methosulphate of formula: NH 2 N N ,CH 3 SO 4 ~ N HO CH 3 - 4' -dimethylamino-2' -nitrobenzene-l' -azo-l-methyl-3 10 pyridinium methosulphate of formula: -T ,14 41 CHa N CH 3 ,CH 3 S0 4 ~ N NO 2 N C'a - 4' -dimethylaminobenzene-1' -azo-1, 6-dimethyl-3 pyridinium methosulphate of formula: CH 3 CH , CH 3 SO4 NN H 3 C N CH 3 5 - 4'-aminobenzene-1'-azo-3-pyridine N-oxide of formula: NH 2 N N - 4' -dimethylaminobenzene-l' -azo-3-pyridine N-oxide of formula: 'P 1> 42 CH 3 CH 3 NN N 0 - 4'-N,N-bis (f-hydroxyethyl)aminobenzene-1'-azo-3 pyridine N-oxide of formula: CH 2 CH 2 OH CH 2 CH 2 OH N N 0 5 - 4' -dimethylamino-2' -methylbenzene-1' -azo-1-ethyl-3 pyridinium ethosulphate of formula: CH j3 N 3 2 H 5 SO 4 N. N . CH 3 C 2 H 5 - 4' -dimethylamino-2' -methylbenzene-1' -azo-l-butyl-3 pyridinium bromide of formula: RA1, 1-)C 43 CH 3 N CH 3 , Br N N N C4HH 3 - 4'-dimethylamino-2'-chlorobenzene-1'-azo-l-methyl-3 pyridinium methosulphate of formula: CHa H 3 ,CH 3 S0 4 N I~CI N OH 3 5 - 2',4'-diamino-5'-methylbenzene-1'-azo-l-methyl-3 pyridinium methosulphate of formula: CH 3 NNH 2 I, CH 3 SO 4 N NN N. NH 2 OH 3 - 4'-phenylaminobenzene-1'-azo-l-methyl-3-pyridinium methosulphate of formula: 44 H N N N ,CHaSO N 3 N CH 3 - 2' -acetylamino-4' -dimethylaminobenzene-1' -azo-l ethyl-3-pyridinium ethosulphate of formula: CH 3 N CH 3 ,C 2 HSS0 4 N IN N NHCOCH 3 C 2 H 5 5 - 2' ,4' -diamino-5' -methoxybenzene-1' -azo-l-methyl-3 pyridinium methosulphate of formula: OCH 3 NH 2 , CH 3 SO 4 N NH NH 2 N CH 3 and - 2' -amino-4' -dimethylaminobenzene-1' -azo-l-methyl-3 pyridinium methosulphate of formula: 770 45 CH 3 N 3CH , CH 3 SO 4 NN NH2 CH 3
14. Composition according to any one of the preceding claims, characterized in that the 3-amino pyridine derivative(s) of formula (I) represent(s) from 5 0.001 to 10% by weight relative to the total weight of the dye composition.
15. Composition according to Claim 14, characterized in that the 3-aminopyridine derivative(s) of formula (I) represent(s) from 0.01 to 5% by weight 10 relative to the total weight of the dye composition.
16. Composition according to any one of the preceding claims, characterized in that the meta aminophenol derivatives of formula (II) are chosen from 5-amino-2-methoxyphenol, 5-amino-2- ( p 15 hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N- (P hydroxyethyl)amino-2-methylphenol, 5-N-(P hydroxyethyl) amino-4-methoxy-2-methylphenol, 5-amino-4 methoxy-2-methylphenol, 5-amino-4-chloro-2 methylphenol, 5-amino-2, 4-dimethoxyphenol, 5- (y 20 hydroxypropylamino) -2-methylphenol, 3-amino-2-chloro-6 methylphenol, 3-amino-6-chlorophenol and 3-($ -Tj 46 aminoethyl)amino-6-chlorophenol, and the addition salts thereof with an acid.
17. Composition according to any one of the preceding claims, characterized in that the meta 5 aminophenol derivative(s) of formula (II) represent(s) from 0.0001 to 10% by weight relative to the total weight of the dye composition.
18. Composition according to Claim 17, characterized in that the meta-aminophenol derivative(s) 10 of formula (II) represent(s) from 0.005 to 5% by weight relative to the total weight of the dye composition.
19. Composition according to any one of the preceding claims, characterized in that it contains one or more couplers other than the meta-aminophenol 15 derivatives of formula (II) as defined in Claim 1 and/or one or more direct dyes other than the 3-aminopyridine derivatives of formula (I) as defined in Claim 1.
20. Composition according to any one of the 20 preceding claims, characterized in that the addition salts with an acid are chosen from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
21. Composition according to any one of the 25 preceding claims, characterized in that the medium which is suitable for dyeing consists of water or of a mixture of water and at least one organic solvent. RA 47
22. Composition according to any one of the preceding claims, characterized in that it has a pH of between 3 and 12.
23. Process for dyeing keratin fibres, and 5 in particular human keratin fibres such as the hair, characterized in that at least one dye composition as defined in any one of Claims 1 to 22 is applied to the said fibres, the colour being developed at acidic, neutral or alkaline pH with the aid of an oxidizing 10 agent which is added to the dye composition only at the time of use, or which is present in an oxidizing composition that is applied simultaneously or sequentially.
24. Process according to Claim 23, 15 characterized in that the oxidizing agent present in the oxidizing composition is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates, percarbonates and persulphates, peracids and enzymes. 20
25. Multi-compartment dyeing device or multi-compartment dyeing "kit", a first compartment of which contains a dye composition as defined in any one of Claims 1 to 22 and a second compartment of which contains an oxidizing composition.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9803453A FR2776185B1 (en) | 1998-03-20 | 1998-03-20 | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| FR98/03453 | 1998-03-20 | ||
| PCT/FR1999/000542 WO1999048466A1 (en) | 1998-03-20 | 1999-03-11 | Oxidation dyeing composition for keratinous fibres containing a 3-aminopyridine azo derivative and dyeing method using said composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2733399A true AU2733399A (en) | 1999-10-18 |
| AU730779B2 AU730779B2 (en) | 2001-03-15 |
Family
ID=9524288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU27333/99A Ceased AU730779B2 (en) | 1998-03-20 | 1999-03-11 | Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0998261B1 (en) |
| JP (1) | JP2000512317A (en) |
| KR (1) | KR20010012428A (en) |
| CN (1) | CN1258213A (en) |
| AT (1) | ATE238028T1 (en) |
| AU (1) | AU730779B2 (en) |
| BR (1) | BR9904903A (en) |
| CA (1) | CA2288995A1 (en) |
| DE (1) | DE69907113T2 (en) |
| FR (1) | FR2776185B1 (en) |
| HU (1) | HUP0002535A3 (en) |
| PL (1) | PL336892A1 (en) |
| RU (1) | RU2185812C2 (en) |
| WO (1) | WO1999048466A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3090358B1 (en) * | 2018-12-21 | 2020-12-18 | Oreal | Process for dyeing keratin materials using a direct dye and an unsaturated heterocyclic salt and composition comprising them |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU71015A1 (en) * | 1974-09-27 | 1976-08-19 | ||
| DE4241173A1 (en) * | 1992-12-07 | 1994-06-09 | Wella Ag | Hair colorants containing 3-pyridine azo dyes and new 3-pyridineazo dyes |
| DE19515903C2 (en) * | 1995-04-29 | 1998-04-16 | Wella Ag | Means and methods for oxidative coloring of hair |
| KR100296169B1 (en) * | 1996-04-25 | 2001-08-07 | 조지안느 플로 | Method for dyeing keratin fibres with oxidation dye precursors and direct powder dies |
-
1998
- 1998-03-20 FR FR9803453A patent/FR2776185B1/en not_active Expired - Fee Related
-
1999
- 1999-03-11 BR BR9904903-1A patent/BR9904903A/en not_active IP Right Cessation
- 1999-03-11 HU HU0002535A patent/HUP0002535A3/en unknown
- 1999-03-11 KR KR1019997010381A patent/KR20010012428A/en active IP Right Grant
- 1999-03-11 WO PCT/FR1999/000542 patent/WO1999048466A1/en not_active Application Discontinuation
- 1999-03-11 AU AU27333/99A patent/AU730779B2/en not_active Ceased
- 1999-03-11 JP JP11547836A patent/JP2000512317A/en active Pending
- 1999-03-11 DE DE69907113T patent/DE69907113T2/en not_active Expired - Lifetime
- 1999-03-11 CA CA002288995A patent/CA2288995A1/en not_active Abandoned
- 1999-03-11 RU RU99127303/14A patent/RU2185812C2/en not_active IP Right Cessation
- 1999-03-11 AT AT99907685T patent/ATE238028T1/en not_active IP Right Cessation
- 1999-03-11 EP EP99907685A patent/EP0998261B1/en not_active Expired - Lifetime
- 1999-03-11 CN CN99800308.5A patent/CN1258213A/en active Pending
- 1999-03-11 PL PL99336892A patent/PL336892A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0998261B1 (en) | 2003-04-23 |
| HUP0002535A3 (en) | 2003-02-28 |
| CA2288995A1 (en) | 1999-09-30 |
| HUP0002535A2 (en) | 2000-12-28 |
| CN1258213A (en) | 2000-06-28 |
| EP0998261A1 (en) | 2000-05-10 |
| JP2000512317A (en) | 2000-09-19 |
| DE69907113T2 (en) | 2004-01-29 |
| RU2185812C2 (en) | 2002-07-27 |
| ATE238028T1 (en) | 2003-05-15 |
| FR2776185B1 (en) | 2001-01-26 |
| DE69907113D1 (en) | 2003-05-28 |
| FR2776185A1 (en) | 1999-09-24 |
| PL336892A1 (en) | 2000-07-17 |
| AU730779B2 (en) | 2001-03-15 |
| WO1999048466A1 (en) | 1999-09-30 |
| BR9904903A (en) | 2000-07-04 |
| KR20010012428A (en) | 2001-02-15 |
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