GB2057019A - Process for dyeing human hair and composition for carrying out this process - Google Patents
Process for dyeing human hair and composition for carrying out this process Download PDFInfo
- Publication number
- GB2057019A GB2057019A GB8024090A GB8024090A GB2057019A GB 2057019 A GB2057019 A GB 2057019A GB 8024090 A GB8024090 A GB 8024090A GB 8024090 A GB8024090 A GB 8024090A GB 2057019 A GB2057019 A GB 2057019A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- methoxy
- group
- benzaldehyde
- hair
- 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
- 238000004043 dyeing Methods 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 239000002243 precursor Substances 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000982 direct dye Substances 0.000 claims abstract description 7
- 239000000118 hair dye Substances 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 6
- 239000007800 oxidant agent Substances 0.000 claims description 21
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 29
- 239000000975 dye Substances 0.000 description 26
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 20
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 20
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 10
- -1 p-toluylenediamine Chemical compound 0.000 description 8
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 8
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 8
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 229960003371 protocatechualdehyde Drugs 0.000 description 5
- 229940018563 3-aminophenol Drugs 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RFQSMLBZXQOMKK-UHFFFAOYSA-N [3-[(4,8-diamino-6-bromo-1,5-dioxonaphthalen-2-yl)amino]phenyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC(NC=2C(C3=C(N)C=C(Br)C(=O)C3=C(N)C=2)=O)=C1 RFQSMLBZXQOMKK-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 4
- 229940043349 potassium metabisulfite Drugs 0.000 description 4
- 235000010263 potassium metabisulphite Nutrition 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- VPBQEWYEJDAYKP-UHFFFAOYSA-N (2-chloro-4,5-difluorophenyl)methanol Chemical compound OCC1=CC(F)=C(F)C=C1Cl VPBQEWYEJDAYKP-UHFFFAOYSA-N 0.000 description 2
- ZRVPOURSNDQODC-UHFFFAOYSA-M 4-[(2,4-dimethyl-1,2,4-triazol-4-ium-3-yl)diazenyl]-n,n-dimethylaniline;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=NN1C ZRVPOURSNDQODC-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 239000011697 sodium iodate Substances 0.000 description 2
- 229940032753 sodium iodate Drugs 0.000 description 2
- 235000015281 sodium iodate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 2
- ANLILZBBUVRVRP-UHFFFAOYSA-N (3-hydroxy-4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1O ANLILZBBUVRVRP-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- VPMMJSPGZSFEAH-UHFFFAOYSA-N 2,4-diaminophenol;hydrochloride Chemical compound [Cl-].NC1=CC=C(O)C([NH3+])=C1 VPMMJSPGZSFEAH-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 1
- KZTWOUOZKZQDMN-UHFFFAOYSA-N 2,5-diaminotoluene sulfate Chemical compound OS(O)(=O)=O.CC1=CC(N)=CC=C1N KZTWOUOZKZQDMN-UHFFFAOYSA-N 0.000 description 1
- 229940075147 2,5-diaminotoluene sulfate Drugs 0.000 description 1
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- VOLCMGPDRGNUGR-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)-3-nitroanilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1[N+]([O-])=O VOLCMGPDRGNUGR-UHFFFAOYSA-N 0.000 description 1
- DXHCRGRTXVYEKC-UHFFFAOYSA-N 2-[anilino(ethyl)amino]acetamide Chemical compound C(C)N(CC(N)=O)NC1=CC=CC=C1 DXHCRGRTXVYEKC-UHFFFAOYSA-N 0.000 description 1
- ADCWDMYESTYBBN-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-3-methyl-4-[(4-nitrophenyl)diazenyl]anilino]ethanol Chemical compound CC1=CC(N(CCO)CCO)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 ADCWDMYESTYBBN-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- UBYRKVOEXRNDCV-UHFFFAOYSA-N 2-hydroxy-3-methoxybenzaldehyde 2-methylbenzene-1,4-diamine sulfuric acid Chemical compound S(=O)(=O)(O)O.NC1=C(C=C(C=C1)N)C.OC1=C(C=O)C=CC=C1OC UBYRKVOEXRNDCV-UHFFFAOYSA-N 0.000 description 1
- BVWOHFHLLLPJLH-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine Chemical compound COC1=C(C)C(N)=C(C)C=C1N BVWOHFHLLLPJLH-UHFFFAOYSA-N 0.000 description 1
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- WHJNKCNHEVCICH-UHFFFAOYSA-N 2-nitro-1-n-phenylbenzene-1,4-diamine Chemical compound [O-][N+](=O)C1=CC(N)=CC=C1NC1=CC=CC=C1 WHJNKCNHEVCICH-UHFFFAOYSA-N 0.000 description 1
- VWLLPPSBBHDXHK-UHFFFAOYSA-N 3,4-diaminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1N VWLLPPSBBHDXHK-UHFFFAOYSA-N 0.000 description 1
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 description 1
- BCPQALWAROJVLE-UHFFFAOYSA-N 4-(2,4-dinitroanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O BCPQALWAROJVLE-UHFFFAOYSA-N 0.000 description 1
- YRUPBAWWCPVHFT-UHFFFAOYSA-N 4-(4-hydroxyanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(O)C=C1 YRUPBAWWCPVHFT-UHFFFAOYSA-N 0.000 description 1
- UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 1
- WHODQVWERNSQEO-UHFFFAOYSA-N 4-Amino-2-nitrophenol Chemical compound NC1=CC=C(O)C([N+]([O-])=O)=C1 WHODQVWERNSQEO-UHFFFAOYSA-N 0.000 description 1
- IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
- XCJRRZLPXALCIP-UHFFFAOYSA-N 4-n-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCNC1=CC=C(N)C=C1 XCJRRZLPXALCIP-UHFFFAOYSA-N 0.000 description 1
- XSHZMHVULBOPDY-UHFFFAOYSA-N 4-n-methyl-2-nitrobenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C([N+]([O-])=O)=C1 XSHZMHVULBOPDY-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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- 206010019049 Hair texture abnormal Diseases 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Chemical class 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- URGYLQKORWLZAQ-UHFFFAOYSA-N azanium;periodate Chemical compound [NH4+].[O-]I(=O)(=O)=O URGYLQKORWLZAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- UFZOLVFGAOAEHD-UHFFFAOYSA-N benzaldehyde;phenol Chemical compound OC1=CC=CC=C1.O=CC1=CC=CC=C1 UFZOLVFGAOAEHD-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- QFCGWLMVBQWKLP-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methoxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)C(O)=C1 QFCGWLMVBQWKLP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000006083 mineral thickener Substances 0.000 description 1
- ODVQLBCSJIDHJL-UHFFFAOYSA-N n-(3-hydroxy-2,4-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(O)=C1C ODVQLBCSJIDHJL-UHFFFAOYSA-N 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
Abstract
An agent for dyeing human hair, comprising a) a hydroxybenzaldehyde, in solution, b) if appropriate, a known precursor for hair dyes, c) if appropriate, a direct dye and d) if appropriate, conventional additives, wherein the hydroxybenzaldehyde employed is a compound of the formula <IMAGE> where R1 represents a hydrogen atom or the OH group, R2 represents an OCH3 group or a hydrogen atom, R3 represents an OCH3 group, an OH group or a hydrogen atom and R4 represents an OCH3 group or a hydrogen atom, with the proviso that only one of R1 and R3 can be an OH group.
Description
SPECIFICATION
Process for dyeing human hair and composition for carrying out this process
This invention provides a process for dyeing human hair and an agent (i.e. a composition) for carrying out this process.
Agents for changing the color of hair by bleaching (to produce a blond effect) and dyeing are known, and are described, for example, in Ullmanns Encyklopädie der technischen Chemie, 4th Edition,
Volume 12, pages 435-441.
The present invention arose from the problem of providing a versatile process, and agents, for dyeing human hair, by which human hair can be dyed in colors from pale yellow to yellow and from brown to reddish brown, the agents being intended to possess particularly good physiological toleration and toxicological safety. Desired hair dyeings should be obtainable by combination with direct dyes or by combination with dye precursors and oxidizing agents.
More particularly, hair-dyeing agents were sought which have the following propertiest 1. They should make it possible to dye human hair directly in yellow to brown colors without requiring oxidizing agents and/or dye precursors, it being moreover desirable that such hair dyeing can be carried out both in an alkaline medium, up to pH 11, and in an acid medium, up to pH 5. Further it is desirable, in order to provide further dyeing capabilities, that the agents should be combinable with direct hair dyes, to allow any desired hair dyeings to be obtained.
2. The agents should be combinable with the conventional oxidizing agents based on hydrogen peroxide, for the purpose of obtaining brown hair dyeings.
3. The agents should be combinable with dye precursors and hydrogen peroxide in order to allow any desired dyeings to be produced, including both darker hues and lighter hues than the initial hue of the hair.
The invention provides a process for dyeing human hair, which employs a) a hydroxybenzaldehyde in solution, b) if appropriate, an oxidizing agent, c) if appropriate, a known precursor for hair dyes, d) if appropriate, a direct dye and e) if appropriate, conventional additives, wherein the hydroxybenzaldehyde employed is a compound of the formula (I)
where R, represents a hydrogen atom or the OH group, R2 represents an OCH3 group or a hydrogen atom, R3 represents an OCH3 group, an OH group or a hydrogen atom and R4 represents an OCH3 group or a hydrogen atom, with the proviso that only one of R1 and R3 can be an OH group.
The invention further provides an agent for dyeing human hair, for carrying out the above process, comprising a) a hydroxy benzaldehyde in solution, b) if appropriate, a known precursor tor hair dyes, c) if appropriate, a direct dye and d) if appropriate, conventional additives, wherein the hydroxybenzaldehyde employed is a compound of the formula
where R1 represents a hydrogen atom or the OH group, R2 represents an OCH3 group or a hydrogen atom, R3 represents an OCH3 group, an OH group or a hydrogen atom and R4 represents an OCH3 group or a hydrogen atom, with the proviso that only one of R1 and R3 can be an OH group.
Dye precursors known for hair dyes are aromatic difunctional or polyfunctional amines containing at least one primary amino group as well as a further functional group in the m-, of or p-position, or heterocyclic amino compounds, or difunctional or polyfunctional phenols, for example a pphenylenediamine of the general formula Il
and/or one or more acid addition salts of the above compounds.In formula (II), R1, R2 and R3 are
identical or different and each represents a hydrogen atom or an alkyl or alkoxy radical having 1 or 2
carbon atoms, and R4 and R5 are identical or different and each represents a hydrogen atom or an alkyl,
hydroxyalkyl, alkoxyalkyl (the alkoxy radical having 1 or 2 carbon atoms), carbamylalkyl,
mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl or carbethoxyaminoalkyl radical (the alkyl radicals in R4
and R5 having 1 to 3 carbon atoms), with the proviso that R1 or R3 is a hydrogen atom if R4 and R5 are
not hydrogen atoms.
As such p-phenylenediamines there may be mentioned:
p-phenylenediamine, p-toluylenediamine, 2-methyl-5-methoxy-p-phenylenediamine, 2,6-dimethyl-p
phenylenediamine, 2,6-dimethyl-3-methoxy-p-phenylenediamine, 4-(N-methoxyethylamino)-aniline, 4
(N-ethyl-N-carbamylmethylamino)-aniline and/or 4-N,N-di-p-hydroxyethylamino)-aniline.
A preferred embodiment of the agent contains 2-aminophenol and/or 2,5-diaminotoluene as the dye precursors
Further specific dye precursors and compounds are of the type of 4-hydroxy4'aminodiphenylamine and/or 4,4'-dihydroxydiphenylamine and/or their derivatives, especially 2 acetamido-3,5-dimethyl-4,4'-dihydroxydiphenylamine, 2-acetamido-3,5-dimethyl-4,4'-dihydroxy-2chlorodiphenylamine, 2-acetamido-5-methyl-4;;4'-dihydroxy-2'-chlorodiphenylamine, 2-ureido-3,5 dimethyl-4,4'-dihydroxy-2'-chlorodiphenylamine, 2-ureido4-hydroxy-4'-aminodiphenylamine, 2acetamido-4-hydroxy-4'-aminodiphenylamine, 2,5-dihydroxy-4,4'-di-[bis-(2-hydroxyethyl)-amino]- diphenylamine, 2-methoxy-4-amino-2' ,5'-dihydroxy-4'-(2-hydroxyethyl)-aminodiphenylamine, 2 acetamido-4-hydroxy-5,3',5'-trimethyi-4'-aminodiphenylamine, 2-acetamido-4,4'-dihydroxy-5methoxy-2'-chlorodiphenylamine, 2-ureido-4,4'-dihydroxy-5-methoxy-2'-chlorodiphenylamine, 2 ureido-4,4'-dihydroxy-5-methoxy-2'-chlorodiphenylamine, 2-ureido-4-hydroxy-5-methyl-4'-chloro-3'methylaminodiphenylamine and 2-ureido-4-hydroxy-5-methyl-4'-N-ethyl-Nureidoaminodiphenylamine.
The following may furthermore be mentioned as dye precursors: resorcinol, m-aminophenol, 2methyl-5-aminophenol, methyl-5-(N-p-hydroxyethylamino)-phenol, 6-hydroxybenzomorpholine, 2,6dimethyl-5-acetylaminophenol, 2-methyl-5-carboxyaminophenol, 2-methoxy-5carbethoxyaminophenol and/or 2-methyl-5-ureidophenol.
A polyaminophenol, monoaminodiphenol, diaminodiphenol and/or polyphenol, preferably trihydroxybenzene, can also be employed as the dye precursor.
As direct dyes, the hair-dyeing agent may contain nitro dyes, for example the disodium salt of 2,4dinitronapth-1 -ol-7-sulfonic acid, 2,4-dinitro-4'-hydroxydiphenylamine, 4-nitro-4'-aminoazobenzene, the Na salt of 2,4-dinitro-3'-sulfo-4'-phenylaminodiphenylamine, 2-methyl-4-bis-(2-hydroxyethyl)amino-4'-nitroazobenzene, 2-hydroxy-5-nitrophenyl- l-azo3-butan-2-on-l -oic acid anilide, 1,2-diamino 4-nitrobenzene,-1,4-diamino-2-nitrobenzene, 1 -hydroxy-2-amino-4-nitrobenzene, 1-hydroxy-2-amino- 5-nitrobenzene, 1 -hydroxy-2-amino-4,6-dinitrobenzene, 1 -hydroxy-2-nitro-4-aminobenzene, 1-amino 2-nitro-4-[bis-(2-hydroxyethyl)-amino]-benzene, 1-amino-2-nitro-4-methylaminobenzene, 2-nitro-4aminodiphenylamine and 1 -hydroxy-3-nitro-4-aminobenzene.
In certain embodiments the agent contains at least one additive from the group comprising penetrating agents, foaming agents, thickeners, antioxidants, alkalis or acids (for adjusting the pH), perfumes, sequestering agents and film-forming agents.
In a specific embodiment of the agent, the pH value is in the range from 8 to 1 1.5, preferably from 9 to 10.
The alkali used can be one or more compounds from the group consisting of ammonia, the alkylamines, alkanolamines and ammonium derivatives, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate.
In addition, water-soluble anionic, cationic, non-ionic or amphoteric surface-active substances can be incorporated into the agent according to the invention. Examples of particularly suitable surfaceactive substances are compounds selected from the group consisting of alkylbenzenesulfonates, alkylnaphthalenesulfonates, fatty alcohol-sulfates, fatty alcohol-ether-sulfates, alkylsulfonates, quaternary ammonium salts, preferably trimethylcetylammonium bromide, cetylpyridinium chloride or cetylpyridinium bromide, fatty acid diethanolamides, polyoxyethylated acids and alcohols, and polyoxyethylated alkylphenols. The surface-active substances are preferably present in the agent according to the invention in a proportion of from 0.5 to 30% by weight, especially from 4 to 25% by weight.
Furthermore, organic solvents can be added to the agent according to the invention in order to solubilise the insufficiently water-soluble compounds. Examples of advantageous solvents are ethanol, isopropanol, glycerol, glycols such as butylglycol, ethylene glycol or propylene glycol, diethylene glycol monoethyl ether and monomethyl ether, and analogous compounds. Advantageously, the dyeing agent according to the invention can contain the solvents in an amount of from 1 to 40% by weight, preferably from 5 to 30% by weight.
Examples of advantageous thickeners which can be incorporated into the dyeing agents according to the invention are sodium alginate, gum arabic, cellulose derivatives, such as methylcellulose or the sodium salt of carboxymethylcellulose, and acrylic acid polymers; mineral thickeners, such as bentonite, can be used equally well. The proportion of the thickeners is preferably 0.5 to 5% by weight, especially 0.5 to 3% by weight, based on the total dyeing agent.
Examples of anitoxidants are potassium metabisulfite, sodium dithionite, sodium sulfite, thioglycollic acid, sodium bisulfite and ascorbic acid. The proportion of the antioxidants can be 0.05 to 1% by weight, relative to the total weight of the dyeing agent.
Oxidizing agents, such as hydrogen peroxide, urea peroxide or per-salts, for example ammonium persulfate, are used in the dyeing process according to the invention. Advantageously, the oxidizing agent used is an aqueous solution in general containing 310% by weight of H202, or urea-peroxide or sodium perborate.
The compounds of the formula (I) are in general present in the dyeing agent according to the invention in a proportion of 0.01 to 5.0% by weight, relative to the total weight of the dyeing agent.
Compounds of the formula (I) include 4-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-5-methoxy benza Idehyde, 2-hydroxy-4-methoxy-benzaldehyde and 2-hydroxy-3-methoxy-benzaldehyde.
The dyeing agent of the invention can be in the form of a solution, paste, cream or jelly or in any other formulation which is suitable for dyeing human hair and is commercially available as, for example, a hair dyeing agent, hair toner, toning fixer and hair rinse.
In order to show that dilute solutions of the compounds of the formula (I) make it possible to dye human hair even in the absence of oxidizing agents, the following tests were carried out, it being particularly noteworthy that the dyeings can be carried out in a pH range of about 5 to about 11 (with the exception of when 2-hydroxy-4-methoxy-benzaldehyde and 4-hydroxy-3-methoxy-benzaldehyde are used).
Test 1 for dyeing strands of human hair with 2-hydroxy-s-methoxy-benzaldehyde 2-Hydroxy-3-methoxy-benzaldehyde was dissolved, at various concentratons, in a solution consisting of 47% by weight of water, 47% by weight of 2-propanol and 6% by weight of 25% strength
NH3, and the strands of human hair were in each case treated with the solution for 30 minutes at room temperature.The results are shown in Table I:
Table I
Concentration of 2-hydroxy- Result of dyeing (in the
3-methoxy-benzaldehyde absence of an oxidizing
agent)
0.1% by weight pale yellow
0.2% by weight somewhat more pronounced
pale yellow
0.5% by weight stronger yellow
1.0% by weight good yellow
2.0% by weight - yellow
5.0% by weight yellow (as for the 2%
strength by weight solution)
At 2% by weight of 2-hydroxy-3-methoxy-benzaldehyde in the solution used, the optimum saturation limit of the dyeing is reached. Similar results were obtained on using 2-hydroxy4-methoxybenzaldehyde or 2-hydroxy-5-methoxy-benzaldehyde.
The tests which follow show that dilute solutions of 4-hydroxy-3-methoxy-benzaldehyde, 2hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-5-methoxy-benzaldehyde or 2-hydroxy4-methoxybenzaldehyde can also be used in combination with oxidizing agents for dyeing human hair.
Test 2 for dyeing strands of human hair with 2-hydroxy-3-methoxy-benzaldehyde and hydrogen peroxide:
The procedure followed was as described for Test 1, but the solution additionally contained 3% by weight of hydrogen peroxide.
The results obtained are shown in Table II below:
Table II Concentration of 2-hydroxy- Result of dyeing (in the
3-methoxy-benzaldehyde presence of an oxidizing
agent) 0.1% by weight delicate brown
0.2% by weight stronger brown
0.5% by weight stronger brown
1.0% by weight light brown
2.0% by weight light-medium brown
5.0% by weight medium brown
If, in Test 2, the 2-hydroxy-3-methoxy-benzaldehyde was replaced by 4-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-4-methoxy-benzaldehye or 2-hydroxy-5-methoxy-benzaldehyde, similar dyeing results were obtained.
Test 3 for dyeing strands of human hair with 2-hydroxy3-methoxy-benzaldehyde, 2-aminophenol and hydrogen pernxiff'e: The procedure followed was as described for Test 1, but the solution additionally contained the amount of 2-aminophenol shown in Table Ill, as well as 3% by weight of hydrogen peroxide.
The results obtained are shown in Table Ill below:
TABLE Ill
Concentration of Concentration Dyeing result
2-hydroxy-3-methoxy of 2-amino (using an
benzaldehyde phenol oxidizing agent)
1% 1% coppery golden
brown
In order to demonstrate that 2-hydroxy-3-methoxy-benzaldehyde can be used, together with other dye precursors, in the presence of oxidizing agents, to dye human hair, Test 4 was carried out.
Test 4 for dyeing strands of human hair with 2-hydroxy-3-methoxy-benzaldebyde and various dye precursors in the presence of oxidizing agents:
The procedure followed was as described for Test 1, but the 2-hydroxy-3-methoxy-benzaldehyde concentration was 1.0% by weight. The hydrogen peroxide content was 3% by weight.
The results obtained are shown in Table IV below:
Table IV
Dye precursor + hydrogen Result of dyeing
peroxide + 2-hydroxy-3
methoxy-benzaldehyde
2,5-Diaminotoluene sulfate yellowish grey
2,4-Diaminophenol hydrochloride light brown
2,4-Diaminoanisole sulfate yellow
1 2,4-Triamino... dihydro- greenish grey
chloride
2-Hydroxy-1 ,4-naphthoquinone light brown
2-Aminoresorcinol hydrochloride golden brown
8-Aminoquinoline reddish brown
4-Amino-diphenylamine medium blond
2-Aminophenol light brown
3-Aminophenol medium brown
4-Aminophenol reddish brown
Pyrogallol medium brown
Test 5 for dyeing strands of human hair with 4-hydroxy-3-methoxy-benzaldehyde and various dye precursors in the presence of an oxidizing agent:
The procedure followed was as described in Test 4.The results obtained are summarised in
Table V:
Table V
Dye precursor + 4-hydroxy- Result of dyeing
3-methoxy-benzaldehyde +
hydrogen peroxide
2,5-Diaminotoluene sulfate grey
2-Aminophenol light brown
3-Aminophenol light brown
4-Aminophenol reddish brown
4-Aminodiphenylamine medium blond
Test 6 for dyeing strands of human hair with 2-hydroxy-4-methoxy-benzaldehyde and various dye precursors in the presence of an oxidizing agent:
The procedure followed was as described in Test 4, but the 2-hydroxy-4-methoxy-benzaldehyde concentration was 1.0% by weight. The concentration of the additional dye precursor was 1.0% by weight in each case.
The results obtained are shown in Table VI below:
Table VI
Dye precursor + hydrogen Result of dyeing
peroxide + 2-hydroxy4- methoxy-benzaldehyde
2,5-Diaminotoluene sulfate grey
2,4-Diaminotoluene light brown 2,4-Diaminoanisole sulfate medium brown
2-Aminophenol light brown
3-Aminophenol light brown
4-Aminophenol medium brown
Pyrocatechol light brown
Resorcinol light brown
Pyrogallol yellowish brown
4-Aminodiphenylamine medium blond
Test 7 for dyeing strands human hair with 2-hydroxy-3-methoxy-benzaldehyde or 2-hydroxy-5methoxy-benzaldehyde in an acid medium::
In each case, a 2-hydroxy-methoxy-benzaldehyde of the above type was dissolved, at 1% strength, in a mixture of 50% by weight of water, 49% by weight of 2-propanol and 1% by weight of 100% strength acetic acid, and the strands of human hair were in each case treated with the solution for 30
minutes at room temperature. In each case, hair strands dyed yellow were obtained.
The effects achievable according to the invention having been demonstrated by the above tests,
the invention will now be further illustrated by the following examples.
EXAMPLE 1
A. A hair-dyeing cream is prepared. A mixture consisting of
cetyl/stearyl alcohol mixture 27.00 g sodium lauryl-sulfate 11 AO g water 11.60g is emulsified, and homogenized to give a cream.
B. The following are incorporated into the cream obtained: 4-hydroxy-3-methoxy-benzaldehyde 1.0 g 2-aminophenol 1.0 g 2,5aiaminotoluene sulfate 1.5 g
2-propanol 15.00 9 water 13.80 g
C. In the next steps of the preparation, the following are incorporated into the mix obtained above
potassium metabisulfite 0.50 g water 5.00 g
D. The following is then incorporated
ammonium hydroxide (25% strength) 6.00 g
E. The whole is made up to 100.00 g with water and the pH is adjusted to 10.5-11.0.
The hair-dyeing cream obtained is filled into tubes.
F. The hair-dyeing cream is mixed with 6% strength aqueous hydrogen peroxide solution in the weight
ratio of 1:1, and the mixture is applied to hair which is 95% grey.
Period of action at 20 C : 30 minutes.
The hair is then rinsed, shampooed and dried. The hair is found to be dark brown.
EXAMPLE 2
The procedure followed is as described in Example 1, except that the materials used are:
A. cetyl/stearyl alcohol mixture 27.00 g
sodium lauryl-sulfate 11.40g water 11.60 g B. 2-hydroxy-3-methoxy-benzaldehyde 1.00 g
2-aminophenol 1.009 2,5-diaminotoluene sulfate 1.50 g
2-propanol 15.00 g water 11.50 g
C. potassium metabisulfite 0.50 g water 5.00 g D. ammonium hydroxide (25% strength) 6.00 g
E. made up with water to 100.00g The pH value is adjusted to 10.5-11.0. After the treatment, the hair is dark brown. Initially, the hair was 95% grey.
EXAMPLE 3
A. cetyl/stearyi alcohol mixture 27.00 g
sodium lauryl-sulfate 11.40g water 11.60g B. 2-hydroxy-3-methoxy-benzaldehyde 1.0 g
2-aminophenol 1.0g
2-propanol 15.00 g water 14.50 g
Example 3 - Continued
C. potassium metabisulfite 0.50 9
water 5.00 9
D. ammonium hydroxide (25% strength) 6.00 9
made up with water to 100.00 9
The pH value is adjusted to 10.5-11.0. After the treatment, the hair is a coppery golden color.
Initially, the hair was light blond.
EXAMPLE 4
A toning-fixer is prepared, as a liquid formulation, in accordance with the following recipe:
Isopropyl alcohol 30.000 9
Copolymer of vinylpyrrolidone and
vinyl acetate 2.000 9
Polyethylene glycol, molecular weight
1.400-1,600 0,200 g
Laurylpyridinium chloride 0.200 9
Perfume 0.300 g
Desalinated water 67.165 9
Basic Blue 99 (Color Index 56059) 0.025 9
Basic Red 22 (Color Index 11055) 0.010 9 2-Hydroxy-3-methoxy-benzaldehyde 0.100 9
100.000 9
The pH value is adjusted to 5.5.
After shampooing and rinsing the hair, 1 5 to 20 ml of the toning fixer are applied to the towel-dry hair. The hair is then, depending on the desired hairstyle, wound on setting rollers. The hair is dried for 30 minutes under a hood and is then combed out.
The hair is found to have been toned medium brown.
EXAMPLE 5
A toner is prepared from the following recipe: 2-Hydroxy-5-methoxy-benzaldehyde 0.70 9
Basic Blue 99 (Color Index 56059) 0.20 9
Basic Brown 16 (Color Index 12250) 0.50 9
Basic Red 22 (Color Index 11055) 0.10 9 2-Propanol 10.00 9
Hydroxyethylcellulose 1.00 9
Glycerol, German Pharmacopoeia 7 3.00 9
Monoethanolamine 1.00 9
Potassium hydroxide solution (51% strength) 2.00 9
Perfume 0.30 9
Desalinated water 81.20 g 100.00g The pH value is adjusted to 8.0-8.5.
The above toner can be packaged in a known manner in aerosol cans, using a propellant. For use,
the toner is sprayed on to the hair, thereby giving these a reddish brown tone.
EXAMPLE 6
A toner is prepared from the following recipe: 2-Hydroxy-4-methoxy-benzaldehyde 0.70 g
Basic Blue 99 (Color Index 56059) 0.20 g
2-Propanol 10.00g Hydroxyethylcellulose 1.00 g Glycerol, German Pharmacopoeia 7 3.00 g
Monoethanolamine 1.00 g
Potassium hydroxide solution (51% strength) 2.00 g
Perfume 0.30 g Desalinated water 81.80 g
100.00 g
The pH value is adjusted to 8.0-8.5.
The toner can be packaged and used as described in Example 5. This gives the hair a greenish
blond tone, so that the toner has an anti-red effect.
EXAMPLE 7
A toner is prepared from the following recipe: 2-Hydroxy-5-methoxy-benzaldehyde 0.70 g
Basic Brown 16 (Color Index 12250) 0.50 g
Basic Blue 99 (Color Index 56059) 0.10 9 2-Propanol 10.00g Hydroxyethylcellulose 1.00 g Glycerol, German Pharmacopoeia 7 3.00 g
Monoethanolamine 1.00 g Potassium hydroxide solution (51% strength) 2.00 g
Perfume 0.30 g Desalinated water 81.40g 100.00 g
The pH value is adjusted to 8.0-8.5.
The toner can be packaged and used as described in Example 5. This gives the hair a light blond tone.
German Auslegeschrift 1,106,925 describes a process for dyeing human hair, using an agent in which the active ingredient is an ortho-dihydroxybenzene compound, protocatechualdehyde being the preferred active ingredient (compare loc. cit., column 2, lines 49-52, column 5 and Example 6) and the dyeing being effected by using an alkali metal periodate and/or ammonium periodate and/or ammonium persulfate as the oxidizing agent.German Auslegeschrift 1,106,925 does not give a prior description of, or even make obvious, the possible use of 2-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-4-methoxy benzaldehyde or 2-hydroxy-5-methoxy-benzaldehyde by themselves, or of 4-hydroxy-3-methoxy benzaldehyde, 2-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-4-methoxy-benza Idehyde or 2hydroxy 5-methoxy-benzaldehyde in combination with an oxidizing agent for the purpose of producing dyeings on human hair.
It is surprising that, in the present invention, a yellow dyeing can be produced on human hair by means of 2-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-4-methoxy-benzaldehyde and 2-hydroxy-5methoxy-benzaldehyde without using an oxidizing agent, whilst protocatechualdehyde does not produce a dyeing under these conditions. It is even more surprising that in the presence of oxidizing agents protocatechualdehyde gives reddish-brown or medium brown hair dyeing only under quite specific conditions (in respect of oxidizing agent and pH value); however, under the conditions required for protocatechualdehyde, brown hair dyeings cannot be achieved with 4-hydroxy-3-methoxy benzaldehyde, 2-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-4-methoxy-benzaldehyde or 2-hydroxy5-methoxy-benzaldehyde.
The table which follows is intended to make clear the surprising results of the comparative investigations.
Comparative investigations by dyeing experiments on human hair, to demonstrate the technlcal advance achleved in relation to German Auslegeschrift 1,106,925.
Active lngredient Active Ingredient
according to the according to German
Concentration invention Ausiegeschriff
of the solution Added oxidizing pH 2-hydroxy-3-methoxy- 1,106,925
No. in% agent value benzaldehyde protocatechualdehyde 1) 1 none 4 yellow no dyeing 2) 0.5 3% of sodium iodate 4 yellow reddish brown 3) 1 none 10 yellow no dyelny 4) 0.5 3% of sodium iodate 10 yellow no dyelng 5) 0.5 3% of ammonium 4 pale yellow or light no dyelng
peroxydisulfate yellow 6) 0.6 3% of ammonium 10 dark yellow medium brown
peroxydisulfate 7) 0.5 3% of H2O2 4 yellow no dyeing 8) 0.5 3% of H2O2 10 light brown no dyeing
Claims (2)
1. A process for dyeing human hair, which employs a) a hydroxybenzaldehyde in solution, b) if appropriate, an oxidizing agent, c) if appropriate, a known precursor for hair dyes, d) if appropriate, a direct dye and e) if appropriate, conventional additives, wherein the hydroxybenzaldehyde employed is a compound of the formula (I)
where R1 represents a hydrogen atom or the OH group, R2 represents an OCH3 group or a hydrogen atom, R3 represents an OCH3 group, an OH group or a hydrogen atom and R4 represents an OCH3 group or a hydrogen atom, with the proviso that only one of R, and R3 can be an OH group.
2. An agent for dyeing human hair, comprising a) a hydroxy benzaldehyde in solution, b) if appropriate, a known precursor for hair dyes, c) if appropriate, a direct dye and d) if appropriate, conventional additives, wherein the hydroxybenzaldehyde employed is a compound of the formula
where R represents a hydrogen atom or the OH group, R2 represents an OCH3 group or a hydrogen atom, R3 represents an OCH3 group, an OH group or a hydrogen atom and R4 represents an OCH3 group or a hydrogen atom, with the proviso that only one of R1 and R3 can be an OH group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2932489A DE2932489B1 (en) | 1979-08-10 | 1979-08-10 | Process for dyeing human hair and means for carrying it out |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2057019A true GB2057019A (en) | 1981-03-25 |
| GB2057019B GB2057019B (en) | 1983-04-07 |
Family
ID=6078159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8024090A Expired GB2057019B (en) | 1979-08-10 | 1980-07-23 | Process for dyeing human hair and composition for carrying out this process |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5629515A (en) |
| AT (1) | ATA405480A (en) |
| BE (1) | BE884696A (en) |
| CH (1) | CH644014A5 (en) |
| DE (1) | DE2932489B1 (en) |
| FR (1) | FR2462907A1 (en) |
| GB (1) | GB2057019B (en) |
| IT (1) | IT1132375B (en) |
| NL (1) | NL8003851A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034014A (en) * | 1990-06-18 | 1991-07-23 | Clairol, Inc. | Hair dye composition and method |
| FR2788432A1 (en) * | 1999-01-19 | 2000-07-21 | Oreal | Combination of cationic dyes is used in compositions for direct dyeing of keratinic fibers, especially human hair |
| WO2012146529A1 (en) * | 2011-04-29 | 2012-11-01 | L'oreal | Dye composition using a particular phenolic coupler in a medium rich in fatty substances, processes and devices |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2480599A1 (en) * | 1980-04-17 | 1981-10-23 | Oreal | USE OF HYDROXYL DERIVATIVES OF BENZALDEHYDE FOR THE COLORING OF KERATIN FIBERS, PROCESS AND COMPOSITION IMPLEMENTING THEM |
| LU82860A1 (en) * | 1980-10-16 | 1982-05-10 | Oreal | TINCTORIAL COMPOSITIONS BASED ON PRECURSORS OF OXIDATION DYES AND NITER BENZENIC DYES STABLE IN AN ALKALINE REDUCING MEDIUM AND THEIR USE FOR DYEING KERATIN FIBERS |
| DE19618595A1 (en) * | 1996-05-09 | 1997-11-13 | Wella Ag | dye |
| FR2787706B1 (en) * | 1998-12-23 | 2002-06-14 | Oreal | DYEING PROCESS USING A CATIONIC HETEROCYCLIC AMINE AND A SELECTED COMPOUND AMONG AN ALDEHYDE, A KETONE, A QUINONE AND A DERIVATIVE OF DI-IMINO-ISOINDOLINE OR 3-AMINO-ISOINDOLONE |
| FR2787707B1 (en) * | 1998-12-23 | 2002-09-20 | Oreal | DYEING PROCESS USING A CATIONIC DERIVATIVE AND A SELECTED COMPOUND AMONG AN ALDEHYDE, A KETONE, A QUINONE AND A DERIVATIVE OF DI-IMINO-ISOINDOLINE OR 3-AMINO-ISOINDOLONE |
| DE19859809A1 (en) * | 1998-12-23 | 2000-06-29 | Henkel Kgaa | Agent for dyeing keratin fibers |
| FR2787705B1 (en) * | 1998-12-23 | 2002-06-14 | Oreal | DYEING PROCESS USING AN ALIPHATIC CATIONIC AMINE AND A SELECTED COMPOUND AMONG AN ALDEHYDE, A KETONE, A QUINONE AND A DERIVATIVE OF DI-IMINO-ISOINDOLINE OR 3-AMINO-ISOINDOLONE |
| FR2787708B1 (en) * | 1998-12-23 | 2002-09-13 | Oreal | DYEING PROCESS USING AN ACTIVE METHYLENE COMPOUND AND A COMPOUND CHOSEN FROM AN ALDEHYDE, A KETONE, A QUINONE AND A DERIVATIVE OF DI-IMINO-ISOINDOLINE OR 3-AMINO-ISOINDOLONE |
| WO2012084472A1 (en) * | 2010-12-20 | 2012-06-28 | L'oreal | Process for dyeing keratin fibres using hydroxybenzaldehyde derivatives, oxidizing agents and alkalinizing agents in the presence of heat |
| FR2969923B1 (en) * | 2011-01-05 | 2012-12-21 | Oreal | PROCESS FOR COLORING KERATIN FIBERS FROM HYDROXYBENZALDEHYDE DERIVATIVES, OXIDIZING AGENTS, ALKALINIZING AGENTS IN THE PRESENCE OF HEAT |
| FR2968949B1 (en) * | 2010-12-20 | 2012-12-14 | Oreal | PROCESS FOR COLORING KERATIN FIBERS FROM HYDROXYBENZALDEHYDE DERIVATIVES, OXIDIZING AGENTS, ALKALINIZING AGENTS IN THE PRESENCE OF HEAT |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE272737C (en) * | ||||
| FR1164951A (en) * | 1957-01-21 | 1958-10-16 | Oreal | Process for dyeing the hair and other keratin substances, and new products thus obtained |
| IT1013014B (en) * | 1970-11-09 | 1977-03-30 | Procter & Gamble | SOLUTION FOR DYING HAIR AND COMPOSITION USED IN IT |
| CA986019A (en) * | 1971-03-30 | 1976-03-23 | Edward J. Milbrada | Oxidation hair dyes and process |
-
1979
- 1979-08-10 DE DE2932489A patent/DE2932489B1/en not_active Ceased
-
1980
- 1980-07-03 NL NL8003851A patent/NL8003851A/en not_active Application Discontinuation
- 1980-07-18 FR FR8015961A patent/FR2462907A1/en active Pending
- 1980-07-23 GB GB8024090A patent/GB2057019B/en not_active Expired
- 1980-07-24 CH CH567280A patent/CH644014A5/en not_active IP Right Cessation
- 1980-08-06 AT AT0405480A patent/ATA405480A/en not_active Application Discontinuation
- 1980-08-08 IT IT24086/80A patent/IT1132375B/en active
- 1980-08-08 BE BE0/201688A patent/BE884696A/en not_active IP Right Cessation
- 1980-08-11 JP JP10934280A patent/JPS5629515A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034014A (en) * | 1990-06-18 | 1991-07-23 | Clairol, Inc. | Hair dye composition and method |
| FR2788432A1 (en) * | 1999-01-19 | 2000-07-21 | Oreal | Combination of cationic dyes is used in compositions for direct dyeing of keratinic fibers, especially human hair |
| EP1025834A1 (en) * | 1999-01-19 | 2000-08-09 | L'oreal | Use for direct hair dye a combination of two cationic dyes |
| US6432146B1 (en) | 1999-01-19 | 2002-08-13 | L'oreal S.A. | Use of a combination of two cationic dyes for the direct dyeing of keratin fibers |
| WO2012146529A1 (en) * | 2011-04-29 | 2012-11-01 | L'oreal | Dye composition using a particular phenolic coupler in a medium rich in fatty substances, processes and devices |
| FR2974509A1 (en) * | 2011-04-29 | 2012-11-02 | Oreal | COLORING COMPOSITION USING A PARTICULAR PHENOLIC COUPLER IN BODY-RICH MEDIA, METHODS AND DEVICE |
| US9241886B2 (en) | 2011-04-29 | 2016-01-26 | L'oreal | Dye composition using a particular phenolic coupler in a medium rich in fatty substances, processes and devices |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA405480A (en) | 1983-05-15 |
| FR2462907A1 (en) | 1981-02-20 |
| CH644014A5 (en) | 1984-07-13 |
| BE884696A (en) | 1980-12-01 |
| IT8024086A0 (en) | 1980-08-08 |
| JPS5629515A (en) | 1981-03-24 |
| DE2932489B1 (en) | 1980-06-04 |
| IT1132375B (en) | 1986-07-02 |
| NL8003851A (en) | 1981-02-12 |
| GB2057019B (en) | 1983-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |