SE460787B - METAPHENYLENE DIAMINES, PREPARED FOR PREPARATION THEREOF AND COMPOSITION - Google Patents
METAPHENYLENE DIAMINES, PREPARED FOR PREPARATION THEREOF AND COMPOSITIONInfo
- Publication number
- SE460787B SE460787B SE8104072A SE8104072A SE460787B SE 460787 B SE460787 B SE 460787B SE 8104072 A SE8104072 A SE 8104072A SE 8104072 A SE8104072 A SE 8104072A SE 460787 B SE460787 B SE 460787B
- Authority
- SE
- Sweden
- Prior art keywords
- composition
- carbon atoms
- methyl
- composition according
- alkyl chain
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 75
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000004985 diamines Chemical class 0.000 title description 2
- -1 alkali metal salt Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 4
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 4
- 108010076876 Keratins Proteins 0.000 claims description 4
- 102000011782 Keratins Human genes 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000982 direct dye Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 claims description 3
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- ANLILZBBUVRVRP-UHFFFAOYSA-N (3-hydroxy-4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1O ANLILZBBUVRVRP-UHFFFAOYSA-N 0.000 claims description 2
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 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 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000000969 carrier Substances 0.000 claims 1
- UMVWJRMJMOPKKM-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(O)=C1 UMVWJRMJMOPKKM-UHFFFAOYSA-N 0.000 claims 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 14
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000010186 staining Methods 0.000 description 12
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical class CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 9
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229960003330 pentetic acid Drugs 0.000 description 6
- 229960001755 resorcinol Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- GFHYFPARONGSCD-UHFFFAOYSA-N n-(2-hydroxy-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1O GFHYFPARONGSCD-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229960001484 edetic acid Drugs 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical class CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 2
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 238000010953 Ames test Methods 0.000 description 2
- 231100000039 Ames test Toxicity 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
- 241001070941 Castanea Species 0.000 description 2
- 235000014036 Castanea Nutrition 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 241000640882 Condea Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- OEAMJLAMHVYDDD-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC[Na] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC[Na] OEAMJLAMHVYDDD-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002352 nonmutagenic effect Effects 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229960005323 phenoxyethanol Drugs 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite 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
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 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
- GIGNQZIJYUEWTI-UHFFFAOYSA-N 2,3,5-trihydroxytoluene Chemical compound CC1=CC(O)=CC(O)=C1O GIGNQZIJYUEWTI-UHFFFAOYSA-N 0.000 description 1
- PFUWOPAGSMRZSD-UHFFFAOYSA-N 2,6-diaminobenzene-1,4-diol Chemical compound NC1=CC(O)=CC(N)=C1O PFUWOPAGSMRZSD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UTHUZYBSSBFPES-UHFFFAOYSA-N 2-(4-amino-3-nitrophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C=C1[N+]([O-])=O UTHUZYBSSBFPES-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- PUJVAXWQQGSUBF-UHFFFAOYSA-N 2-butoxyethanol;propane-1,2-diol Chemical compound CC(O)CO.CCCCOCCO PUJVAXWQQGSUBF-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- YXWXCSITLKQDLA-UHFFFAOYSA-N 2-nitro-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC([N+]([O-])=O)=C1N YXWXCSITLKQDLA-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- ANHZPHIPRWOGCD-UHFFFAOYSA-N 4-amino-2-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1O ANHZPHIPRWOGCD-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
- YGRFRBUGAPOJDU-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-2-methylphenol Chemical compound CC1=CC=C(NCCO)C=C1O YGRFRBUGAPOJDU-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000557626 Corvus corax Species 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920000084 Gum arabic Chemical class 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-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
- 241000607142 Salmonella Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- 239000000205 acacia gum Chemical class 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid 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
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MAWRVLAEEGMWEO-UHFFFAOYSA-N ethyl 3-amino-5-hydroxy-4-methylbenzoate Chemical compound CCOC(=O)C1=CC(N)=C(C)C(O)=C1 MAWRVLAEEGMWEO-UHFFFAOYSA-N 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000006083 mineral thickener Substances 0.000 description 1
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 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
- A61K8/40—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
Description
460 787 10 15 .2O 25 30 35 2 använda kopplarna vara helt oskadliga och isynnerhet praktiskt taget non-mutagena i Ames-testet på Salmonella Thyphimurium (TA 1538, TA 98, TA 100, TA 1537 och TA 1535, i frånvaro eller närvaro av "S9 MIX" aktiverad med "Arochlor l254"). 460 787 10 15 .2O 25 30 35 2 use the couplers to be completely harmless and in particular virtually non-mutagenic in the Ames test on Salmonella Thyphimurium (TA 1538, TA 98, TA 100, TA 1537 and TA 1535, in the absence or presence of "S9 MIX" activated with "Arochlor l254").
Föreliggande uppfinning har sålunda till uppgift att beskriva nya kemiska föreningar som är lämpliga att utgöra metafenylendiaminkopplare vilka är användbara i färgningskompositioner för keratinfibrer. Föreningarna enligt uppfinningen är särskilt användbara vid hårfärg- ning eftersom de ej blott har en god kopplares färg- ningsegenskaper utan också är fördelaktiga genom sin oskadlighet och vidare är non-mutagena i Ames-testet såsom ovan angivits. I den franska patentansökan 2362 116 har man redan föreslagit metafenylendiaminer som ger tillfredsställande resultat vid hårfärgning, och upp- finningen avser att beskriva andra metafenylendiaminer av samma typ samt deras användning.The present invention thus has for its object to describe new chemical compounds that are suitable for constitute metaphenylenediamine couplers which are useful in dyeing compositions for keratin fibers. The associations according to the invention are particularly useful in hair dye because they not only have the color of a good coupler properties but are also advantageous through their innocence and further are non-mutagenic in the Ames test as indicated above. In French patent application 2362 116 Metaphenylenediamines have already been proposed satisfactory results in hair coloring, and the invention intends to describe other metaphenylenediamines of the same type and their use.
Föreliggande uppfinning avser sålunda en kemisk förening med den allmänna formeln (I): OZ v (I) kännetecknad därav, att Z är en ulkylkedja, som är av- bruten av en eller tvâ syreatomer och har en eller två hydroxylgrupper, varvid alkylkedjan har 4-8 kolatomer, eller motsvarande syrasalter.The present invention thus relates to a chemical compound of the general formula (I): OZ v (IN) characterized in that Z is an alkyl chain which is broken by one or two oxygen atoms and has one or two hydroxyl groups, the alkyl chain having 4-8 carbon atoms, or corresponding acid salts.
Hydroxylgruppen eller -grupperna i alkylkedjan kan eventuellt befinna sig vid kedjans ände. 10 15 20 25 30 35 460 787 3 Uppfinningen hänför sig vidare till ett sätt att framställa föreningarna med den angivna formeln (I).The hydroxyl group or groups in the alkyl chain may possibly be at the end of the chain. 10 15 20 25 30 35 460 787 3 The invention further relates to a method of to prepare the compounds of formula (I).
Detta sätt kännetecknas därav att ett halogenderivat med formeln X-Z bringas att verka på ett alkalisalt av 2-acetylamino-4-nitrofenol, varvid X är en halogen och Z är en alkylkedja, som är avbruten av en eller två syreatomer och har en eller två hydroxylgrupper, varvid alkylkedjan har 4-8 kolatomer, så att radikalen Z konden- seras på kärnan under avlägsnande av en alkalihalogenid, att nitrogruppen i den erhållna produkten sedan reduceras och att slutligen produkten deacetyleras för erhållande av en förening med formeln (I), såsom angivits i kravet 1.This method is characterized in that a halogen derivative with the formula X-Z is brought to act on an alkali salt of 2-acetylamino-4-nitrophenol, wherein X is a halogen and Z is an alkyl chain interrupted by one or two oxygen atoms and has one or two hydroxyl groups, wherein the alkyl chain has 4-8 carbon atoms, so that the radical Z on the core while removing an alkali halide, that the nitro group in the product obtained is then reduced and finally the product is deacetylated to obtain of a compound of formula (I) as claimed in claim 1.
I en föredragen utföringsform är den använda halo- genen X klor och alkalimetallen är kalium, varvid reduk- tion av nitrogruppen sker i alkohollösning under åter- flöde medelst pulverformig zink i närvaro av ammonium- klorid.In a preferred embodiment, the halogen used is gene X is chlorine and the alkali metal is potassium, reducing of the nitro group takes place in alcoholic solution during flow by means of powdered zinc in the presence of ammonium chloride.
Föreliggande uppfinning hänför sig vidare till en komposition för färgning av keratinfibrer och i synner- het hár, varvid kompositionen i en kosmetiskt accetabel bärare innehåller minst en oxidationsbas, som väljes bland: A - parafenylendiaminer med den allmänna formeln (II): R Nq f» R4 Ri KP Rs (n) Rz NH2 eller motsvarande syrasalter, varvid Rl, R2 och R3 är samma eller olika och representerar en väteatom, en alkylradikal med l-4 kolatomer eller en alkoxiradikal med l-2 kolatomer, R4 och R5 är samma eller olika och representerar en väteatom, en alkylradikal, hydroxialkyl, alkoxialkyl, vari alkoxigruppen har 1-2 kolatomer, karbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureido- 460 787 10 15 20 25 30 35 4 alkyl, karbetoxiaminoa kyl, aminoalkyl, monoa kylamino- alkyl, dialkylaminoalkyl, piperidinoalkyl, morfolino- alkyl, varvid alkylgrupperna i R4 och R5 har 1-4 kol- atomer, eller R4 och R5 tillsammans med den kväveatom vartill de är bundna bildar en piperidinogrupp eller morfolinogrupp, under förutsättning att Rl och R3 repre- senterar en väteatom, då R4 och R5 inte representerar någon väteatom, B - paraaminofenoler med den allmänna formeln (III): (III) NH2 eller motsvarande syrasalter, varvid R6 representerar en väteatom, en alkylradikal med l-4 kolatomer eller en halogenatom, såsom klor eller brom, C - heterocykliska baser, kännetecknad därav, att kompositionen såsom kopplare innehåller mellan 0,001 och 2,85 vikt% i förhållande till kompositionens totalvikt av minst en förening med formeln (I) OZ NH2 NH2 där Z är en alkylkedja, som är avbruten av en eller två syreatomer och har en eller två hydroxylgrupper, Avarvid alkylkedjan har 4-8 kolatomer, eller motsvarande syrasalter. av --ïv__ï,_ _ __ _________ 10. 15 20 25 30 35 460 787 5 Man har konstaterat att användning av metafenylen- diaminerna enligt uppfinningen tillsammans med åtmin- stone en oxidationsbas, såsom angivits under A -, B - och C -, gör det möjligt att erhålla färgningskomposi- tioner vilka förlänar hår färgnyanser av god kvalitet, som väl motstâr särskilt tvättning.The present invention further relates to a composition for dyeing keratin fibers and in particular hot hair, the composition being in a cosmetically acceptable table carrier contains at least one oxidation base, which is selected among: A - paraphenylenediamines of the general formula (II): R Nq f » R4 Ri KP Rs (n) Rz NH2 or the corresponding acid salts, wherein R 1, R 2 and R 3 are the same or different and represents a hydrogen atom, a alkyl radical having 1-4 carbon atoms or an alkoxy radical with 1-2 carbon atoms, R4 and R5 are the same or different and represents a hydrogen atom, an alkyl radical, hydroxyalkyl, alkoxyalkyl, wherein the alkoxy group has 1-2 carbon atoms, carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureido- 460 787 10 15 20 25 30 35 4 alkyl, carbethoxyaminoalkyl, aminoalkyl, monoalkylamino- alkyl, dialkylaminoalkyl, piperidinoalkyl, morpholino- alkyl, the alkyl groups of R4 and R5 having 1-4 carbon atoms, or R4 and R5 together with the nitrogen atom to which they are attached form a piperidino group or morpholino group, provided that R1 and R3 centers a hydrogen atom, as R4 and R5 do not represent any hydrogen atom, B - paraaminophenols of the general formula (III): (III) NH2 or corresponding acid salts, wherein R6 represents a hydrogen atom, an alkyl radical having 1-4 carbon atoms or a halogen atom, such as chlorine or bromine, C - heterocyclic bases, characterized in that the composition acts as a coupler contains between 0.001 and 2.85% by weight in ratio to the total weight of the composition of at least one compound with formula (I) OZ NH2 NH2 wherein Z is an alkyl chain interrupted by one or two oxygen atoms and has one or two hydroxyl groups, Wherein the alkyl chain has 4-8 carbon atoms, or equivalent acid salts. av --ïv__ï, _ _ __ _________ 10. 15 20 25 30 35 460 787 5 It has been found that the use of metaphenylene the diamines of the invention together with at least an oxidation base, as specified under A -, B - and C -, makes it possible to obtain dyeing compositions which imparts good color shades to hair, which is particularly resistant to washing.
Allmänt gör kopplarna enligt uppfinningen det möj- ligt att med parafenylendiaminer erhålla blåfärgningar som är mer eller mindre rika på grönt eller purpur och med paraaminofenoler rödfärgningar. Färgningskomposi- tionerna enligt uppfinningen kan därför med fördel samtidigt innehålla parafenylendiaminer och paraamino- , fenoler.In general, the couplers according to the invention make it possible to obtain blue stains with paraphenylenediamines which are more or less rich in green or purple and with paraaminophenols red stains. Staining composition the ions of the invention may therefore be advantageous simultaneously contain paraphenylenediamines and paraamino-, phenols.
Man har konstaterat att särskilt intressanta resul- tat erhålles genom att bland samtliga föreningar med formeln (I) eller motsvarande syrasalter använda 2,4- -diaminofenyl,ß(ß'-hydroxietoxi)etyleter, särskilt i form av dihydroklorid..It has been found that particularly interesting results is obtained by including among all compounds with formula (I) or the corresponding acid salts use 2,4- -diaminophenyl, ß (ß'-hydroxyethoxy) ethyl ether, especially in form of dihydrochloride ..
Färgningskompositionerna enligt uppfinningen kan, förutom kopplaren eller kopplarna med formeln (I) och den med dem kombinerade oxidationsbasen eller -baserra, innehålla följande produkter ensamma eller i kombination med varandra: l) andra kända kopplare, såsom resorcin, 2-metylresorcin, metaaminofenol, 2-metyl-5-aminofenol, 2-metyl-5-N-(ß- -hydroxietyl)aminofenol, 6-hydroxibensomorfolin, 2,6-dimetyl-3-acetylaminofenol, 2-metyl-5-karbetoxi- aminofenol, 2-metoxi-5-karbetoxiaminofenol, 2-metyl-5- -ureidofenol och l-fenyl-3-metyl-5-pyrazolon; 2) ortofenylendiaminer och ortoaminofenoler, eventuellt med substituenter på ringen eller på aminfunktionerna, eller också ortodifenol, vilka produkter genom komplexa oxidationsmekanismer kan leda till nya färgade föreningar vare sig detta sker genom ringslutning på dem själva eller genom inverkan på parafenylendiaminerna; 3) prekursorer till färgämnen ibensenserien innehållande minst tre substituenter på kärnan, vilka valts ur den grupp som utgöres av hydroxi, metoxi eller amino, såsom , a... , ..._..,..,..-,._....»...-,-~.- 460 10 15 20 25 30 35 787 6 dihydrokloriden av 2,6-diamino-hydrokinon, trihydro- kloriden av 2,6-diamino-4-N,N-bis-(etyl)amino-fenol, dihydrokloriden av 2,4-diaminofenol, l,2,4-trihydroxi- bensen, 2,3,5-trihydroxitoluen eller 4-metoxi-2-amino-N- (B-hydroxietyl)-anilin; 4) färgämnesprekursorer i naftalenserien, såsom 2-hydr- oxi~l,4-naftokinon och 5-hydroxi-1,4-naftokinon. 5) leukoderivat av indoaniliner eller indofenoler, såsom 4,4'-áihydxoxi-2-amino-5-metyl-difenylamin, 4,4'-dihydroxi~2-N-(B-hydroxietyl)amino-5-metyl-2'-kloro- -difenylamin, 2,4'-diamino-4-hydroxi-5-metyl-difenyl- amin, 2,4-dihydroxi-4'-N-(B~metoxietyl)amino-difenylamin; 2,4-dihydroxi-5-metyl-4'-N-(B-metoxietyl)amino-difenyl- amin; 6) direkta färgämnen och t ex de som är valda ur klassen nitrerade färgämnen i bensenserien, såsom l-N,N-bis-(B- -hydroxietyl)amino-3-nitro-4-N'-metylaminobensen, l-N,N-(metyl,ß-hydroxietyl)amino-3-nitro-4-N'-(B-hydroxi- etyl)aminobensen, l-N,N-(metyl,ß-hydroxietyl)amino-3- -nitro-4-N'-metylamino-bensen, 3-nitro-4-N-(ß-hydroxi- etyl)amino-anisol, 3-nitro-4-N-(B-hydroxietyl)amino- -fenol, (3-nitro-4-amino)-fenoxietanol, (3-nitro-4-N- -metylamino)-fenoxietanol, 2-N-(B-hydroxietyl)amino- -5-nitro-anisol. pH för färgningskompositionerna enligt uppfinningen är basiskt, t ex mellan 8 och 11,5. Bland användbara alkaliseringsmedel kan nämnas ammoniak, alkylaminer, såsom etylamin eller trietylamin, alkanolaminer, såsom mono-, di- eller tri-etanolamin, alkyl-alkanolaminer, såsom metyl-dietanolamin, hydroxider av natrium eller kalium, karbonater av natrium, kalium eller ammonium.The coloring compositions of the invention may, in addition to the coupler or couplers of formula (I) and the oxidation base or base combined with them, contain the following products alone or in combination together: l) other known couplers, such as resorcin, 2-methylresorcin, methaminophenol, 2-methyl-5-aminophenol, 2-methyl-5-N- (β- -hydroxyethyl) aminophenol, 6-hydroxybenzomorpholine, 2,6-dimethyl-3-acetylaminophenol, 2-methyl-5-carbethoxy- aminophenol, 2-methoxy-5-carbethoxyaminophenol, 2-methyl-5- -ureidophenol and 1-phenyl-3-methyl-5-pyrazolone; 2) orthophenylenediamines and orthoaminophenols, optionally with substituents on the ring or on the amine functions, or orthodiphenol, which products through complex oxidation mechanisms can lead to new colored compounds whether this is done by ring closure on themselves or by action on the paraphenylenediamines; 3) precursors for dyes containing the bone series at least three substituents on the nucleus, which are selected from it group consisting of hydroxy, methoxy or amino, such as , a ..., ..._ .., .., ..-, ._.... »...-, - ~ .- 460 10 15 20 25 30 35 787 6 the dihydrochloride of 2,6-diamino-hydroquinone, trihydro- the chloride of 2,6-diamino-4-N, N-bis- (ethyl) amino-phenol, the dihydrochloride of 2,4-diaminophenol, 1,2,4-trihydroxy- benzene, 2,3,5-trihydroxytoluene or 4-methoxy-2-amino-N- (Β-hydroxyethyl) -aniline; 4) dye precursors in the naphthalene series, such as 2-hydride oxy-1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone. 5) leukode derivatives of indoanilines or indophenols, such as 4,4'-alkyloxy-2-amino-5-methyl-diphenylamine, 4,4'-dihydroxy-2-N- (B-hydroxyethyl) amino-5-methyl-2'-chloro- -diphenylamine, 2,4'-diamino-4-hydroxy-5-methyl-diphenyl- amine, 2,4-dihydroxy-4'-N- (β-methoxyethyl) aminodiphenylamine; 2,4-dihydroxy-5-methyl-4'-N- (β-methoxyethyl) amino-diphenyl- amine; 6) direct dyes and eg those selected from the class nitrated dyes in the benzene series, such as 1-N, N-bis- (B- -hydroxyethyl) amino-3-nitro-4-N'-methylaminobenzene, 1-N, N- (methyl, β-hydroxyethyl) amino-3-nitro-4-N '- (β-hydroxy- ethyl) aminobenzene, 1-N, N- (methyl, β-hydroxyethyl) amino-3- -nitro-4-N'-methylamino-benzene, 3-nitro-4-N- (β-hydroxy- ethyl) amino-anisole, 3-nitro-4-N- (β-hydroxyethyl) amino- -phenol, (3-nitro-4-amino) -phenoxyethanol, (3-nitro-4-N- -methylamino) -phenoxyethanol, 2-N- (β-hydroxyethyl) amino- -5-nitro-anisole. pH of the coloring compositions of the invention is basic, eg between 8 and 11.5. Among useful alkalizing agents include ammonia, alkylamines, such as ethylamine or triethylamine, alkanolamines, such as mono-, di- or tri-ethanolamine, alkyl-alkanolamines, such as methyl diethanolamine, hydroxides of sodium or potassium, carbonates of sodium, potassium or ammonium.
Bland användbara acidifieringsmedel kan nämnas mjölk- syra, ättiksyra, vinsyra och fosforsyra.Useful acidifying agents include milk acid, acetic acid, tartaric acid and phosphoric acid.
Den kosmetiskt acceptabla bäraren som är kombinerad med basen eller baserna, kopplaren eller kopplarna och eventuellt det direkta färgämnet eller färgämnena l.i kompositionen kan, förutom vatten, utgöras av yt- 10 15 20 25 30 35 460 787 7 aktiva medel, organiska lösningsmedel, förtjocknings- medel, antioxidanter, genomträngningsmedel, skummedel, sekvestreringsmedel, filmbildande produkter, behand- lingsmedel och parfymer.The cosmetically acceptable carrier that is combined with the base or bases, the coupler or couplers and optionally the direct dye or dyes l.in the composition may, in addition to water, consist of surface 10 15 20 25 30 35 460 787 7 active agents, organic solvents, thickeners agents, antioxidants, penetrants, foaming agents, sequestrants, film-forming products, and perfumes.
Man kan försätta kompositionen enligt uppfinningen med anjoniska, katjoniska, nonjoniska eller amfotära ytaktiva medel eller blandningar därav. Av de ytaktiva medel som är särskilt användbara kan nämnas alkyl- bensen-sulfonater, alkylnaftalensulfonater, sulfater, eter-sulfater och sulfonater av fettalkoholer, kvar- tära ammoniumsalter, såsom trimetyl-cetylammoniumbromid, cetyl-pyridiniumbromid, dietanolamider av fettsyror, polyoxietylen- eller polyglycerol-alkoholer och -syror samt polyoxietylen- eller polyglycerol-alkylfenoler.The composition according to the invention can be added with anionic, cationic, nonionic or amphoteric surfactants or mixtures thereof. Of the surfactants agents which are particularly useful may be mentioned alkyl- benzene sulfonates, alkylnaphthalene sulfonates, sulfates, ether sulphates and sulphonates of fatty alcohols, ammonium salts, such as trimethylcetylammonium bromide, cetyl pyridinium bromide, diethanolamides of fatty acids, polyoxyethylene or polyglycerol alcohols and acids and polyoxyethylene or polyglycerol alkylphenols.
De ytaktiva medlen förefinnes lämpligen i kompositionen enligt uppfinningen i en mängd av mellan 0,5 och 55 vikt%, företrädesvis mellan 4 och 40 vikt%, räknat på komposi- tionens totalvikt.The surfactants are suitably present in the composition according to the invention in an amount of between 0.5 and 55% by weight, preferably between 4 and 40% by weight, based on the composition total weight of the tion.
Man kan även försätta kompositionen enligt upp- finningen med organiska lösningsmedel för att solubi- lisera föreningar som inte är tillräckligt lösliga i vatten. Bland lösningsmedel som med fördel kan användas, kan exempelvis nämnas etanol, isopropanol, glycerol, glykoler och deras etrar, såsom 2-butoxi-etanol, etylen-glykol, propylenglykol, monoetyleter och mono- metyleter av dietylenglykol och analoga lösningsmedel.You can also set the composition according to with organic solvents to solubilize lyse compounds that are not sufficiently soluble in water. Among solvents that can be used to advantage, may be mentioned for example ethanol, isopropanol, glycerol, glycols and their ethers, such as 2-butoxyethanol, ethylene glycol, propylene glycol, monoethyl ether and monoethyl methyl ether of diethylene glycol and analogous solvents.
Lösningsmedlen kan företrädesvis förekomma i komposi- tionen i en mängd av l-40 vikt%, företrädesvis S-30 vikt%, räknat på kompositionens totalvikt.The solvents may preferably be present in the composition. in an amount of 1-40% by weight, preferably S-30% by weight, calculated on the total weight of the composition.
De förtjockningsmedel, som kan sättas till kompo- sitionen enligt uppfinningen, kan med fördel väljas ur den grupp som innefattar natriumalginat, gummi arabikum, cellulosaderivat, såsom metylcellulosa, hydroxietyl- cellulosa, hydroxipropylmetylcellulosa, natriumsaltet av karboximetylcellulosa och polymerer av akrylsyra.The thickeners that can be added to the position according to the invention, can advantageously be selected from the group comprising sodium alginate, gum arabic, cellulose derivatives such as methylcellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose, the sodium salt of carboxymethylcellulose and polymers of acrylic acid.
Man kan likaledes använda mineraliska förtjockningsmedel, såsom bentonit. Förtjockningsmedlen föreligger lämpligen ¿ 460 787 10 15 20 25 8 i en mängd av 0,5-5 vikt%, räknat på kompositionens totalvikt, företrädesvis 0,5-3 vikt%.Mineral thickeners can also be used, such as bentonite. The thickeners are suitably present ¿ 460 787 10 15 20 25 8 in an amount of 0.5-5% by weight, based on the composition total weight, preferably 0.5-3% by weight.
De anti-oxidanter som kan sättas till kompositionen enligt uppfinningen, kan med fördel väljas ur den grupp som innefattar natriumsulfit, tioglykolsyra, merkapto- bärnstenssyra, natriumvätesulfit, askorbinsyra och hydrokinon. Anti-oxidanterna kan förekomma i komposi- tionen i en mängd av 0,05-1,5 vikt%, räknat på komposi- tionens totalvikt.The antioxidants that can be added to the composition according to the invention, can advantageously be selected from that group which includes sodium sulfite, thioglycolic acid, mercapto- succinic acid, sodium hydrogen sulphite, ascorbic acid and hydroquinone. The antioxidants may be present in the composition. in an amount of 0.05-1.5% by weight, based on the composition total weight of the tion.
Färgningskompositionen enligt uppfinningen inne- håller vid användningstillfället oxidationsmedel, såsom väteperoxid, ureaperoxid eller persalter, såsom ammo- niumpersulfat.The dyeing composition according to the invention comprises hold oxidizing agents at the time of use, such as hydrogen peroxide, urea peroxide or persalts, such as nium persulfate.
Färgningskompositionen enligt uppfinningen kan föreligga i form av en vätska, en kräm, en gel, en aerosol eller i varje annan lämplig form för att förläna keratinfibrerna färg.The dyeing composition according to the invention can present in the form of a liquid, a cream, a gel, a aerosol or in any other suitable form to impart keratin fibers color.
Vid färgning av här med kompositionen enligt före- liggande uppfinning blandar man en komposition enligt uppfinningen med ett oxidationsmedel, applicerar nämnda blandning pá håret, låter blandningen verka pà háret kunder en tidrymd av 5-45 min, sköljer, och tvättar och sköljer eventuellt åter samt torkar därefter håret.When dyeing here with the composition according to According to the present invention, a composition according to the invention with an oxidizing agent, applies said mixture on the hair, lets the mixture act on the hair customers a period of 5-45 min, rinsing, and washing and possibly rinse again and then dry the hair.
För att underlätta förståelsen av uppfinningen skall i belysande och ej begränsande syfte flera ut- föringsexempel beskrivas i det följande. æ-fiü-mw ~_ 460 787 EXEMPEL l Framställning av dihydrokloriden av (2,4-diamino)-fenyl- B-(B'-hydroxietoxi)etyleter Den framställda föreningen har följande formel: O-CH2~CH2-O-CH2-CH2-OH NH 2 , 2HCl Första fasen OH \ NHcocH3 -----> NO OK NHCOCH3 N02 460 787 lO Nfaëra = OK NHCOCH3 + Cl-CH2-CH2-O-CH2-CH2-OH N02 O-CH2-CH2-O-CH2-CH2-OH NHCOCH3 N02 Tredje fasen : O-CH2-CH2-O-CH2-CH2-OH ' NHCOCH3 N02 0-CH2-CH2-O-CH2-CH2-OH NHCOCH3 , HCI _NH 10 20 25 30 35 460 787 ll _Fjärde fasen o-CH -cfl -0-ca -CH -on 2 2 2 2 \\ NHcocH3 I , Hcl “""“ä / NH2 O-CH2-CH2~O-CH2-CH2'OH NH 2 , 2Hc1 NH Första steget: Framställning av kaliumsaltet av 2-acetylamino-4-nitro-fenol 2150 ml etanol som i lösning innehöll 1,89 mol (133 g) so s kaliumxarbonac, kylaes till -1o°c. narefcer tillsattes så småningom, under omröring och vid en temperatur under 5°C, 1,89 mol (371 g) 2-acetylamino- -4-nitro-fenol. Kaliumsaltet utfälldes. Produkten tor- kades, tvättades i etanol och torkades under vakuum vid so°c.To facilitate the understanding of the invention for illustrative and non-limiting purposes, several examples are described below. æ- fi ü-mw ~ _ 460 787 EXAMPLE 1 Preparation of the dihydrochloride of (2,4-diamino) -phenyl- B- (B'-hydroxyethoxy) ethyl ether The prepared compound has the following formula: O-CH2 ~ CH2-O-CH2-CH2-OH NH 2 , 2HCl The first phase OH \ NHcocH3 -----> NO OK NHCOCH3 N02 460 787 lO Nfaëra = OK NHCOCH3 + C1-CH2-CH2-O-CH2-CH2-OH N02 O-CH2-CH2-O-CH2-CH2-OH NHCOCH3 N02 Third phase: O-CH2-CH2-O-CH2-CH2-OH ' NHCOCH3 N02 0-CH2-CH2-O-CH2-CH2-OH NHCOCH3 , HCl _NH 10 20 25 30 35 460 787 ll _FOURTH PHASE o-CH -c fl -0-ca -CH -on 2 2 2 2 \\ NHcocH3 I, Hcl “" "“ ä / NH2 O-CH2-CH2 ~ O-CH2-CH2'OH NH 2, 2Hc1 NH First step: Preparation of the potassium salt of 2-acetylamino-4-nitro-phenol 2150 ml of ethanol which in solution contained 1.89 mol (133 g) so s potassium xarbonac, cooled to -1 ° C. narefcer was added gradually, with stirring and at a temperature below 5 ° C, 1.89 mol (371 g) 2-acetylamino- -4-nitro-phenol. The potassium salt precipitated. The product is dry was washed, washed in ethanol and dried under vacuum at so ° c.
Andra steget: Framställning av (2-acetylamino-4-nitro)- fenyl-B-(B'-hydroxietoxi)etvleter Man införde 0,5 mol (117 g) av kaliumsaltet av 2-acetylamino-4-nitrofenol 1 500 ml dimetylformamid.Second step: Preparation of (2-acetylamino-4-nitro) - phenyl-B- (B'-hydroxyethoxy) ethyl ethers 0.5 mol (117 g) of the potassium salt was removed 2-acetylamino-4-nitrophenol 1,500 ml of dimethylformamide.
Därefter tillsatte man under omröring 0,6 mol (64 ml) av monoklorhydrinen av dietylenglykol. Blandningen hölls i 8 h under omröring vid en temperatur nära lOO°C och hälldes sedan 1 2 liter isvatten. Råprodukten torkades, tvättades i vatten, därefter med en kyld normal soda- 460 lO 15 20 25 30 787 12 lösning och slutligen i vatten. Efter torkning under vakuum och omkristallisering i etanol erhöll man den förväntade produkten som smälte vid l52°C.Then 0.6 mol (64 ml) was added with stirring. of the monochlorohydrin of diethylene glycol. The mixture was kept for 8 hours with stirring at a temperature close to 100 ° C and was then poured 1 2 liters of ice water. The crude product was dried, was washed in water, then with a cooled normal soda 460 lO 15 20 25 30 787 12 solution and finally in water. After drying during vacuum and recrystallization from ethanol were obtained the expected product melting at 125 ° C.
En analys av den erhållna produkten gav följande resultat: Analys Beräknat för Cl2§l6§2Q6 funnet C % 50,70 50,88 - H % 5,67 5,64 N % 9,86 9,74 O % 33,77 33,90 Tredje steget: Framställning av monohydrokloriden av (2-acetylamino-4-amino)-fenyl-ß-(B'-hydroxietoxi)etyleter 400 ml etanol (96%) med tillsatts av 75 ml vatten, lO g ammoniumklorid och 200 g pulverformig zink bragtes under omröring till återflöde. Därefter tillsattes så småningom under fortsatt omröring 0,32 mol (91 g) (2-acetylamino-4-nitro)fenyl-B-(ß'-hydroxietoxi)etyleter.An analysis of the product obtained gave the following results: Analysis Calculated for Cl2§l6§2Q6 found C% 50.70 50.88 - H% 5.67 5.64 N% 9.86 9.74 O% 33.77 33.90 Third step: Preparation of the monohydrochloride from (2-acetylamino-4-amino) -phenyl-β- (β'-hydroxyethoxy) ethyl ether 400 ml of ethanol (96%) with the addition of 75 ml of water, 10 g of ammonium chloride and 200 g of powdered zinc were charged while stirring to reflux. Then it was added so gradually with continued stirring 0.32 mol (91 g) (2-acetylamino-4-nitro) phenyl-β- (β'-hydroxyethoxy) ethyl ether.
Efter varje tillsats avfäqfides reaktionsmiljön mycket snabbt. Efter avslutad tillsats av det kvävehaltiga derivatet upprätthöll man upphettningen under ett 10-tal minuter,filtrerade reaktionsmiljön och samlade upp filtratet i 35 ml etanol (96%) som försatts med 34 ml 36 %-ig klorvätesyra som dessförinnan kylts medelst en torris-etanolblandning. Den förväntade produkten utkristalliserades i form av hydroklorid. Produkten tor- kades, tvättades med en liten mängd absolut etanol som dessförinnan kylts till -lO°C, och torkades sedan under vakuum vid 55°C.After each addition, the reaction environment was greatly degraded Quickly. After completion of the addition of the nitrogenous the derivative, the heating was maintained as a whole About 10 minutes, filtered the reaction medium and collected up the filtrate in 35 ml of ethanol (96%) added with 34 ml of 36% hydrochloric acid previously cooled by a dry ice-ethanol mixture. The expected product crystallized out as hydrochloride. The product is dry was washed with a small amount of absolute ethanol which previously cooled to -10 ° C, and then dried under vacuum at 55 ° C.
En analys av den erhållna produkten gav följande resultat: 10 15 20 460 787 13 Analys Beräknat för Cl2§l8§2Q4, HCl Funnet C % 49,57 49,56 H % 6,58 6,50 N % 9,63 9,48 O % 22,01 21,83 Cl % 12,19 12,30 Fjärde steget: Framställning av dihydrokloriden av (2,4-diamino)-fenyl-ß-(B'-hydroxietoxi)etyleter Man upphettade under âterflöde och omröring 0,25 mol (70,9 g) av monohydrokloriden av (2-acetylamino-4-amino)- fenyl-ß-(B'-hydroxietoxi)etyleter i 210 ml absolut etanol mättad med klorvätegas. Efter 10 min upphettningxmnrupp- lösningen total och sedan börjadeden förväntade dihydro- kloriden att utfällas efter ungefär 0,5 h. Man vidmakt- höll upphettningen inalles l h och kylde sedan reaktions- miljön till OOC. Man torkade dihydrokloriden, tvättade den med en liten mängd absolut etanol vid OOC och tor- kade den sedan under vakuum vid 5500. Den smälte under sönderdelning mellan 180 och l85°C.An analysis of the product obtained gave the following results: 10 15 20 460 787 13 Analysis Calculated for Cl2§l8§2Q4, HCl Found C% 49.57 49.56 H% 6.58 6.50 N% 9.63 9.48 O% 22.01 21.83 Cl% 12.19 12.30 Fourth step: Preparation of the dihydrochloride of (2,4-diamino) -phenyl-β- (β'-hydroxyethoxy) ethyl ether 0.25 mol was heated under reflux and stirring (70.9 g) of the monohydrochloride of (2-acetylamino-4-amino) - phenyl-β- (β'-hydroxyethoxy) ethyl ether in 210 ml of absolute ethanol saturated with hydrogen chloride gas. After 10 minutes of heating solution total and since the beginning of the expected dihydrogen the chloride to precipitate after about 0.5 h. kept the heating for a total of 1 h and then cooled the reaction the environment to OOC. The dihydrochloride was dried, washed with a small amount of absolute ethanol at 0 ° C and dry it was then vacuumed at 5500. It melted during decomposition between 180 and 185 ° C.
En analys av den erhållna produkten gav följande resultat.An analysis of the product obtained gave the following results.
Analys L % H % N % O % Cl % Beräknat för Clog 42,12 6,36 9,82 16,83 24,87 2HCl Funnet 163293' 42,24 6,39 9,73 17,07 24,90-24,94 460 10 15 20 25 787 14 ßxßmrrb 2 Man framställde följande färgningskomposition: Föreningen enligt exempel l 2,85 g Parafenylendiamin 1,08 g Oxietylinerad nonylfenol med fyra mol etylen- oxid, som säljes under benämningen "CEMULSOL NP4" av firma "RHONE POULENC" 21 g Oxietylinerad nonylfenol med nio mol etylen- oxid, som säljes under benämningen "CEMULSOL NP9" av firma "RHONE POULENC" 24 g Oljesyra 4 g 2-butoxietanol 3 g Etanol (96 %) l0 9 Pentanatriumsaltet av dietylen-triamin- penta-ättiksyra, som säljs under be- nämningen "MASQUOL DTPA" 2,5 g Tioglykolsyra 0,6 g Alnmoniak (22°ßë> 1o g Vatten till l00 g Kompositionens pH var 9,7.Analysis L% HRS % N% O% Cl% Intended for Clog 42.12 6.36 9.82 16.83 24.87 2HCl Found 163293 ' 42.24 6.39 9.73 17.07 24.90-24.94 460 10 15 20 25 787 14 ßxßmrrb 2 The following dyeing composition was prepared: The compound of Example 1 is 2.85 g Paraphenylenediamine 1.08 g Oxyethylated nonylphenol with four moles of ethylene oxide, which is sold under the name "CEMULSOL NP4" from the company "RHONE POULENC" 21 g Oxyethylated nonylphenol with nine moles of ethylene oxide, which is sold under the name "CEMULSOL NP9" from the company "RHONE POULENC" 24 g Oleic acid 4 g 2-butoxyethanol 3 g Ethanol (96%) 10 9 The pentasodium salt of diethylene triamine pentaacetic acid, which is sold under the name "MASQUOL DTPA" 2.5 g Thioglycolic acid 0.6 g Alnmonia (22 ° ßë> 1o g Water to l00 g The pH of the composition was 9.7.
Vid användningstillfället tillsattes 100 q väte- poroxid, som alstrar 20 volymer.At the time of use, 100 q of hydrogen was added. poroxide, which produces 20 volumes.
Blandningen applicerades under 25 min vid 28°C på till 90 % naturligt vitt hår och gav håret efter skölj- ning och shamponering en blåsvart färgning. 10 15 20 460 787 l O 8 8 2 5 15 EXEMPEL 3 _Följande färgningskomposition framställdes: Föreningen enligt exempel l Paraaminofenol 2-butoxietanol Propylenglykol Karboximetylcellulosa Ammoniumlaurylsulfat Pentanatriumsaltet av dietylen-triaminpenta- ättiksyra, som säljs under benämningen "MASQUOL DTPA" 2 Tioglykolsyra 0,4 Anunøniak (22°Bë> lo Vatten till 100 Kompositionens pH var 10.The mixture was applied for 25 minutes at 28 ° C to 90% natural white hair and gave the hair after rinsing and shampooing a bluish black coloration. 10 15 20 460 787 l O 8 8 2 5 15 EXAMPLE 3 The following dyeing composition was prepared: The compound of Example 1 Paraaminophenol 2-butoxyethanol Propylene glycol Carboxymethylcellulose Ammonium lauryl sulfate The pentasodium salt of diethylene-triaminepenta- acetic acid, which is sold under the name "MASQUOL DTPA" 2 Thioglycolic acid 0.4 Anunøniak (22 ° Bë> lo Water to 100 The pH of the composition was 10.
Vid användningstillfället tillsattes 100 g väteperoxid, som alstrar 20 volymer.At the time of use, 100 g were added hydrogen peroxide, which produces 20 volumes.
Blandningen applicerades under 30 min vid 25°C på till 90 % naturligt vitt hår och gav håret efter sköljning och shamponering en röd kopparfärg.The mixture was applied for 30 minutes at 25 ° C on to 90% natural white hair and gave the hair after rinsing and shampooing a red copper color.
Q LO Q \n Q ~n Q u:«Q m 10 15 20 25 30 7237 16 EXEMPEL 4 Följande färgningskomposition framställdes: Föreningen enligt exempel l 0,285 g Dihydrokloriden av 2,6-dimetyl-parafenylen- diamin 0,209 g Oxietylinerad oleylalkohol med två mol etylen- oxid 4,5 g Oxietylinerad oleylakolhol med fyra mol etylenoxid 4,5 g Oxietylinerad oleylamin med tolv mol etylenoxid, som försäljs under benämningen “ETHOMEEN TOl2" av firma "ARMOUR HESS" 4,5 g Dietanolamider av fettsyror från kopra 9 g Propylenglykol 4 g 2-butoxietanol 8 g Etanol (96%) 6 g Pentanatriumsaltet av dietylen-triaminpenta- ättiksyra, som säljs under benämningen "MASQUOL DTPA" 2 g Hydrokinon 0,15 g Natriumbisulfitlösning (3s°Bë) 1,3 g ammoniak (22°së> 5 g Vatten till 100 g Kompositionens pH var 10.Q LO Q \ n Q ~ n Q u: «Q m 10 15 20 25 30 7237 16 EXAMPLE 4 The following staining composition was prepared: The compound of Example 1 is 0.285 g The dihydrochloride of 2,6-dimethyl-paraphenylene- diamine 0.209 g Oxiethylated oleyl alcohol with two moles of ethylene oxide 4.5 g Oxiethylated oleyla alcohol with four moles ethylene oxide 4.5 g Oxiethylated oleylamine with twelve moles ethylene oxide, sold under the name "ETHOMEEN TOl2" by company "ARMOR HESS" 4.5 g Diethanolamides of fatty acids from copra 9 g Propylene glycol 4 g 2-butoxyethanol 8 g Ethanol (96%) 6 g The pentasodium salt of diethylene-triaminepenta- acetic acid, which is sold under the name "MASQUOL DTPA" 2 g Hydroquinone 0.15 g Sodium bisulfite solution (3s ° Bë) 1.3 g ammonia (22 °> 5 g Water to 100 g The pH of the composition was 10.
Vid användningstillfället tillsättes 100 9 vätß- peroxid, som alstrar 20 volymer.At the time of use, 100 g of hydrogen are added. peroxide, which produces 20 volumes.
Blandningen applicerades under 30 min vid 28°C på här som dessförinnan avfärgats till vitt, och gav håret efter sköljning och shamponering en lätt purpurfärgad intensiv blå färgning. 460 787 10 155 20 25 30 17 EXEMPEL 5 Följande färgningskomposition framställdes: Föreningen enligt exempel l 0,012 g Parafenylendiamin 0,108 g Dihydrokloriden av 2,6-dimetyl-parafenylen- diamin 0,0502 g Paraaminofenol 0,155 g 2-metylresorcin 0,19 g Metaaminofenol 0,12 g 1-fenyl-3-metyl-5-pyrazolon 0,09 g (3-N-metylamino-4-nitro)fenoxietanol 0,2 g Oxietylinerad nonylfenol med fyra mol etylen- oxid, som säljs under benämningen "CEMULSOL NP4" av firma "RHONE POULENC" 12 g Oxietylinerad nonylfenol med nio mol etylen- oxid, som sälj under benämningen "CEMULSOL NP9" av firma "RHONE POULENC" 15 g Oxietylinerad oleylalkohol med två mol etylenoxid 1,5 g Oxietylinerad oleylalkohol med fyra mol etylenoxid 1,5 g Propylenglykol g Etylen-diamin-tetraättiksyra, som säljs under benämningen "TRILON B" 0,12 g Ammoniak (22°ße> 11 g Merkaptobärnstenssyra 0,2 g Vatten till 100 g Kompositionens pH var 10,4.The mixture was applied for 30 minutes at 28 ° C here which had previously been discolored to white, and gave the hair after rinsing and shampooing a light purple intense blue staining. 460 787 10 155 20 25 30 17 EXAMPLE 5 The following staining composition was prepared: The compound of Example 1 is 0.012 g Paraphenylenediamine 0.108 g The dihydrochloride of 2,6-dimethyl-paraphenylene- diamine 0.0502 g Paraaminophenol 0.155 g 2-methylresorcin 0.19 g Methaminophenol 0.12 g 1-phenyl-3-methyl-5-pyrazolone 0.09 g (3-N-methylamino-4-nitro) phenoxyethanol 0.2 g Oxyethylated nonylphenol with four moles of ethylene oxide, which is sold under the name "CEMULSOL NP4" from the company "RHONE POULENC" 12 g Oxyethylated nonylphenol with nine moles of ethylene oxide, which is sold under the name "CEMULSOL NP9" from the company "RHONE POULENC" 15 g Oxiethylated oleyl alcohol with two moles ethylene oxide 1.5 g Oxiethylated oleyl alcohol with four moles ethylene oxide 1.5 g Propylene glycol g Ethylene diamine tetraacetic acid sold under the name "TRILON B" 0.12 g Ammonia (22 ° ße> 11 g Mercapto succinic acid 0.2 g Water to 100 g The pH of the composition was 10.4.
Vid användningstillfället tillsattes 75 g väteper- oxid, som alstrar 20 volymer.At the time of use, 75 g of hydrogen peroxide was added. oxide, which produces 20 volumes.
Blandningen applicerades under 25 min vid 30°C på här som dessförinnan avfärgats till vitt, och gav håret efter sköljning och shamponering en guldsands- färgning. 460 787 10 15 20 25 30 l 8 EXEMPEL 6 Följande färgningskomposition framställdes: Föreningen enligt exempel l 0,52 g Parafenylendiamin 0,6 g Paraaminofenol 0,8 g Dihydrokloriden av 4-N,N-di-ß-hydroxietyl- aminoanilin l g Metaaminofenol 0,5 g Resorcin 1,54 g 3-nitro-4-aminofenol 0,6 g Oxietylinerad oleylalkohol med två mol etylenoxid 4,5 9 Oxietylinerad oleylalkohol med fyra mol etylenoxid 4,5 9 Oxietylinerad oleylamin med tolv mol etylenoxid, som säljs under benämningen "sTHozuzu-:N Tou" av firma "ARMouR mass" 4,5 g Dietanolamider av fettsyror från kopra 9 9 Propylenglykol 4 9 2-butoxietanol 8 9 Etanol (96%) 6 9 Pentanatriumsaltet av dietylen-triamin- -pentaättiksyra, som säljs under be- nämningen "MASQUOL DTPA" 2 9 Tioglykolsyra 0,5 9 ammoniak (22°ßë) 10 g Vatten till 100 9 Kompositionens pH var 10,3.The mixture was applied for 25 minutes at 30 ° C on here previously discolored to white, and gave hair after rinsing and shampooing a golden sand dyeing. 460 787 10 15 20 25 30 l 8 EXAMPLE 6 The following staining composition was prepared: The compound of Example 1 is 0.52 g Paraphenylenediamine 0.6 g Paraaminophenol 0.8 g The dihydrochloride of 4-N, N-di-β-hydroxyethyl- aminoaniline l g Methaminophenol 0.5 g Resorcin 1.54 g 3-nitro-4-aminophenol 0.6 g Oxiethylated oleyl alcohol with two moles ethylene oxide 4.5 9 Oxiethylated oleyl alcohol with four moles ethylene oxide 4.5 9 Oxiethylated oleylamine with twelve moles ethylene oxide, which is sold under the name "sTHozuzu-: N Tou" by firm "ARMouR mass" 4.5 g Diethanolamides of fatty acids from copra 9 9 Propylene glycol 4 9 2-butoxyethanol 8 9 Ethanol (96%) 6 9 The pentasodium salt of diethylene triamine -pentaacetic acid, which is sold under the name "MASQUOL DTPA" 2 9 Thioglycolic acid 0.5 9 ammonia (22 ° C) 10 g Water to 100 9 The pH of the composition was 10.3.
Vid användningstillfället tillsattes l00 9 väteper- oxid, som alstrar 20 volymer.At the time of use, 100 g of hydrogen peroxide were added. oxide, which produces 20 volumes.
Blandningen applicerades under 30 min vid 28°C på här som avfärgats till mörkblont, och gav håret efter sköljning och shamponering en brun färgning. 10 15 20 25 30 19 EXEMPEL 7 460 787 Följande färgningskomposition framställdes: Föreningen enligt exempel l Parafenylendiamin Paraaminofenol 4-N-metylaminofenolsulfat Resorcin Metaaminofenol 2-metyl-5-N-B-hydroxietylaminofenol 2-isopropyl-6-nitroanilin Cetyl-stearylalkohol som säljs under be- nämningen "ALFOL C16/18 E" av firman "CONDEA" Cetyl-stearylnatriumsulfat, som säljs under benämningen "CIRE DE LANETTE E" av firman "HENKEL " Btoxylerad ricinolja, som säljs under be- nämningen “CEMULSOL B" av firman "RHONE POULENC" Oleyldietanolamid Pentanatriumsaltet av dietylen-triamin- -pentaättiksyra, som säljs under be- nämningen "MASQUOL DTPA" Tioglykolsyra Hydrokinon Amoniax <2z°ae> Vatten till Kompositionens pH var 10,4.The mixture was applied for 30 minutes at 28 ° C on here discolored to dark blonde, and gave the hair after rinsing and shampooing a brown stain. 10 15 20 25 30 19 EXAMPLE 7 460 787 The following staining composition was prepared: The compound of Example 1 Paraphenylenediamine Paraaminophenol 4-N-methylaminophenol sulfate Resorcin Methaminophenol 2-methyl-5-N-β-hydroxyethylaminophenol 2-isopropyl-6-nitroaniline Cetyl stearyl alcohol sold under the the name "ALFOL C16 / 18 E" by the company "CONDEA" Cetyl stearyl sodium sulfate, sold below the name "CIRE DE LANETTE E" by the company "HENKEL" Btoxylated castor oil, which is sold under the name "CEMULSOL B" by the company "RHONE POULENC" Oil diethanolamide The pentasodium salt of diethylene triamine -pentaacetic acid, which is sold under the name "MASQUOL DTPA" Thioglycolic acid Hydroquinone Amoniax <2z ° ae> Water to The pH of the composition was 10.4.
Vid användningstillfället tillsattes 100 g väteper- oxid, som alstrar 20 volymer. 0,l 0,31 0,4 0,4 0,5 0,3 0,41 0,81 0,5 2,5 0,5 0,15 ll 100 LQLQSQQLQQLQLQ I! LQQLQQQ Blandningen applicerades under 30 min vid 30°C på hår, som avfärgats till vitt, och gav håret efter skölj- ning och shamponering en kopparfärgad mellankastanje- brun färgning.At the time of use, 100 g of hydrogen peroxide was added. oxide, which produces 20 volumes. 0, l 0.31 0.4 0.4 0.5 0.3 0.41 0.81 0.5 2.5 0.5 0.15 ll 100 LQLQSQQLQQLQLQ IN! LQQLQQQ The mixture was applied for 30 minutes at 30 ° C hair, which was bleached to white, and gave the hair after rinsing shampooing a copper-colored intermediate chestnut brown staining.
Q ----~_______i_ 4650 10 15 20 25 30 1¿¿35 e»»§TflnsMcoPALz334" av f1rm¿n=vsERLANn“ 7237 20 EXEMPEL 8 Följande färgningslösning framställdes: Föreningen enligt exempel l 0,0143 g Dihydrokloriden av 4-N-B-metoxietylamino- anilin 0,0120 9 Akrylsyrapolymer med en molekylvikt av 2-3 miljoner, som säljs under benämningen "CARBOPOL 934" av firman "GOODRICH CHEMICAL CO" 1,5 g Etanol (96%) 11 g 2-butoxietanol 5 g Trimetylcetylammoniumbromid 1 g Ety1en-diamin-tetraättiksyra, som säljs under benämningen "TRILON B" 0,1 g ammoniak (22°ßé) 1o g Tioglykolsyra 0,2 g Vatten till 100 g Kompositionens pH var 10,2.Q ---- ~ _______ i_ 4650 10 15 20 25 30 1¿¿35 e »» §T fl nsMcoPALz334 "av f1rm¿n = vsERLANn“ 7237 20 EXAMPLE 8 The following staining solution was prepared: The compound of Example 1 0.0143 g The dihydrochloride of 4-N-β-methoxyethylamino- aniline 0.0120 9 Acrylic acid polymer with a molecular weight of 2-3 million, which are sold under the name "CARBOPOL 934" by the company "GOODRICH CHEMICAL CO "1.5 g Ethanol (96%) 11 g 2-butoxyethanol 5 g Trimethylcetylammonium bromide 1 g Ethylene-diamine-tetraacetic acid sold under the name "TRILON B" 0.1 g ammonia (22 ° C) 1o g Thioglycolic acid 0.2 g Water to 100 g The pH of the composition was 10.2.
Vid användningstillfället tillsattes 20 g väteper- oxid, som alstrar 20 volymer.At the time of use, 20 g of hydrogen peroxide were added. oxide, which produces 20 volumes.
Blandningen applicerades under 30 min vid 30°C på hår, som avfärgats till vitt, och gav håret efter sköljning och shamponering en ljust silverfärgad turkosblá färgning.The mixture was applied for 30 minutes at 30 ° C on hair, which was dyed to white, and gave the hair after rinsing and shampooing a light silver colored turquoise coloring.
EXEMPEL 9' Följande färgningskomposition framställdes: Föreningen enligt exempel 1 0,055 g Parafenylendiamin 0,058 g Paraaminofenol 0,5 g Resorcin 0,4 g Metaaminofenol 0,103 g 2-metyl-5-N-B-hydroxietylaminofenol 0,05 g _ 3ënitro~4-N-metylamino-N,N-di-ß-hydroxi- 'f“"etylanilin"" ' I g ¿ V 0,31 g fíoxíëfišlidešáa nonylfénei med fyra moi _ 'f$§etylenoxid,Jsom säljs under benämningen 12 » g' 10 15 20 25 30 35 .,_;;_:¿f^_:gs t;no1_,. (ess). i, A, , 1o i 21 Oxietylinerad nonylfenol med nio mol etylenoxid, som säljs under benämningen "REMCOPAL 349" av firman "GERLAND" 15 g Oxietylinerad oleylalkohol med tvâ mol etylenoxid 1,5 g Oxietylinerad oleylalkohol med fyra mol etylenoxid 1,5 g Propylenglykol 6 g Natriumbisulfidlösning (35°Bé) 1,2 g Etylen-diamin-tetraättiksyra, som säljs under benämningen "TRILON B" 0,12 g Trietanolamin pH 8,5 Vatten till 100 g Vid användningstillfället tillsattes 70 g väteper- oxid, som alstrar 20 volymer.EXAMPLE 9 ' The following staining composition was prepared: The compound of Example 1 is 0.055 g Paraphenylenediamine 0.058 g Paraaminophenol 0.5 g Resorcin 0.4 g Methaminophenol 0.103 g 2-methyl-5-N-β-hydroxyethylaminophenol 0.05 g 3-Nitro-4-N-methylamino-N, N-di-β-hydroxy- 'f "" ethylaniline ""' I g ¿V 0.31 g fíoxíë fi šlidešáa nonylfénei med four moi _ 'f $ §ethylene oxide, Js sold under the name 12 »g ' 10 15 20 25 30 35 ., _ ;; _: ¿f ^ _: gs t; no1_ ,. (ace). i, A,, 1o i 21 Oxiethylated nonylphenol with nine moles ethylene oxide, which is sold under the name "REMCOPAL 349" by the company "GERLAND" 15 g Oxiethylated oleyl alcohol with two moles ethylene oxide 1.5 g Oxiethylated oleyl alcohol with four moles ethylene oxide 1.5 g Propylene glycol 6 g Sodium bisulfide solution (35 ° B) 1.2 g Ethylene diamine tetraacetic acid sold under the name "TRILON B" 0.12 g Triethanolamine pH 8.5 Water to 100 g At the time of use, 70 g of hydrogen peroxide were added. oxide, which produces 20 volumes.
Blandningen applicerades under 25 min vid 28°C på hår, som avfårgats till vitt, och gav håret efter sköljning och shamponering en nötbrun färgning. sxsMPEL 10 _ Följande färgningskomposition framställdes: Föreningen enligt exempel l 1,3 g Parafenylendiamin 1,81 g Paraaminofenol 0,8 9 Dihydrokloriden av (2,4~diamino)fenoxi- etanol 0,2 9 2-metyl-5-N-B~hydroxietyldminofenol 0,803 g Resorcin 0,81 g Metaaminofenol 0,9 g Oxietylinerad nonylfenol med fyra mol etylenoxid, som säljs under benämningen "CEMULSOL NP4“ av firman "RHONE POULENC" 21 g Oxietylinerad nonylfenol med nio mol "»etylenoxid, som säljs under benämningen ' "CEMULSOL NP9" av firman "RHONE POULENC" 24 g Oljesyra g 0 A Å q 4 g ';2-ngtoxietanol. “ ' 3 g 9, 4650 10 15 20 25 30 das» 7237 22 Pentanatriumsaltet av dietylen-triamin- -pentaättiksyra, som säljs under be- nämningen "MASQUOL DTPA" 2,5 Tioglykolsyra 0,5 Anunoniak (22°ßë) 10 Vatten till 100 Kompositionens pH var 9,5.The mixture was applied for 25 minutes at 28 ° C on hair, which was bleached to white, and gave the hair after rinsing and shampooing a nut brown coloration. sxsMPEL 10 _ The following staining composition was prepared: The compound of Example 1 1.3 g Paraphenylenediamine 1.81 g Paraaminophenol 0.8 9 The dihydrochloride of (2,4-diamino) phenoxy- ethanol 0.2 9 2-methyl-5-N-B-hydroxyethylldminophenol 0.803 g Resorcin 0.81 g Methaminophenol 0.9 g Oxiethylated nonylphenol with four moles ethylene oxide, which is sold under the name "CEMULSOL NP4" by the company "RHONE POULENC" 21 g Oxiethylated nonylphenol with nine moles "'Ethylene oxide, sold under the name' "CEMULSOL NP9" by the company "RHONE POULENC" 24 g Oleic acid g 0 A Å q 4 g 2-ntoxyethanol. '' 3 g 9, 4650 10 15 20 25 30 das » 7237 22 The pentasodium salt of diethylene triamine -pentaacetic acid, which is sold under the name "MASQUOL DTPA" 2.5 Thioglycolic acid 0.5 Anunoniak (22 ° ßë) 10 Water to 100 The pH of the composition was 9.5.
Vid användningstillfället tillsattes 120 g väteper- oxid, som alstrar 20 volymer.At the time of use, 120 g of hydrogen peroxide was added. oxide, which produces 20 volumes.
Blandningen applicerades under 25 min vid 28°C på hår, som avfärgats till halmgult, och gav håret efter sköljning och shamponering en korpsvart färgning.The mixture was applied for 25 minutes at 28 ° C hair, which was discolored to straw yellow, and gave the hair after rinsing and shampooing a raven black stain.
EXEMPEL ll Följande färgningskomposition framställdes: Föreningen enligt exempel l 0,252 Dihydrokloriden av 4-N-ß-metoxietylamino- anilin 0,6 Dihydrokloriden av 2,6-dimetyl-parafenylen- diamin 0,2 Paraaminofenol 0,6 Resorcin á 0,905 Metaaminofenol 0,435 2-metyl-5-N-Bëhydroxietylaminofenol 0,2 6-hydroxi-bensomorfolin 0,435 2-metyl-4-am1no-5-nitrofenol 0,703 Oxietylinerad nonylfenol med fyra mol etylen- oxid, som säljs under benämningen "CEMULSOL _ NP4" av firman "RHONE POULENC" 12 Oxietylinerad nonylfenol med nio mol etylen- «oxid, som säljs under benämningen "CEMULSOL NP9" av firman "RHONE POULENC" 15 Oleylalkohol med.tvâ mol etylenoxid 1,5 . Oleylalkohol med fyra mol etylenoxid 1,5 Propylenglykol A ~ 6 Etylenëdiamin-tetraättiksyra, som säljs j_under benämningen "TRILON B"“ J . ' 0,12 [ammoniak <22°ße) ~ fi- e de 4 0 11 LQKQLQLQ m Q uzwn Q Q u:«n m u:~n Q KJ 10 15 20 25 ao ~3s 460 787 23 Tioglykolsyra 0,5 Vatten till 100 Kompositionens pH var 9,9.EXAMPLE ll The following staining composition was prepared: The compound of Example 1 is 0.252 The dihydrochloride of 4-N-β-methoxyethylamino- aniline 0.6 The dihydrochloride of 2,6-dimethyl-paraphenylene- diamine 0.2 Paraaminophenol 0.6 Resorcin at 0.905 Methaminophenol 0.435 2-methyl-5-N-Behydroxyethylaminophenol 0.2 6-hydroxy-benzomorpholine 0.435 2-methyl-4-amino-5-nitrophenol 0.703 Oxyethylated nonylphenol with four moles of ethylene oxide, sold under the name "CEMULSOL _ NP4 "by the company" RHONE POULENC "12 Oxyethylated nonylphenol with nine moles of ethylene «Oxide, sold under the name" CEMULSOL NP9 "by the company" RHONE POULENC "15 Oleyl alcohol with two moles of ethylene oxide 1.5 . Oleyl alcohol with four moles of ethylene oxide 1.5 Propylene glycol A ~ 6 Ethyleneediamine tetraacetic acid sold j_under the name "TRILON B" "J. 0.12 [ammonia <22 ° ße) ~ fi- e de 4 0 11 LQKQLQLQ m Q uzwn Q Q u: «n m u: ~ n Q KJ 10 15 20 25 ao ~ 3s 460 787 23 Thioglycolic acid 0.5 Water to 100 The pH of the composition was 9.9.
Vid användningstillfället tillsattes 100 g väteper- oxid, som alstrar 20 volymer.At the time of use, 100 g of hydrogen peroxide was added. oxide, which produces 20 volumes.
Blandningen applicerades under 30 min vid 30°C på till 90 % naturligt blont hår och gav håret efter sköljning och shamponering en kopparfärgad ljus kastanjebrun färgning.The mixture was applied for 30 minutes at 30 ° C on to 90% natural blonde hair and gave the hair after rinsing and shampooing a copper colored candle chestnut staining.
EXEMPEL l 2 Följande färgningskomposition framställdes: Föreningen enligt exempel 1 0,306 Parafenylendiamin 0,307 Dihydrokloriden av 4-N-ß-metoxietylamino- anilin 0,15 2-metylresorcin 0,405 2-metyl-5-N-B-hydroxietylaminofenol 0,115 Dihydrokloriden av (2,4-diamino)fenoxi- etanol 0,106 2-amino-3-nitrofenol 0,203 Cetyl-stearylalkohol, som säljs under be- nämningen "ALFOL C16/18 E" av firman "CONDEA" 8 Cetyl-stearyl-natriumsulfat, som säljs under benämningen "CIRE DE LANETTE E" av firman "RBNKEL" 0,5 Etoxilerad ricinolja, som säljs under benämningen "CEMULSQL B" av firman "RHONE POULENC" 1 .øleyldietanolamid 1,5 =Pentanatriumsaltet"avjdietylentriamin- pentaättiksyra, som säljs under be- i nämningen "MASQUOL DTPA" ' 2,5 ”,Tioglykolsyra 0,5 _UHydrokinon« ~, V _ 0,15 1¿Ammonl¿k«<22°së> - _ Å. ' 1 '11 í° ¿v¿c:en,t111H, ,_ _ “ . > ¿ ., v,_,, ioo 9 9 l-Q lQQI-QW-QQ ,-_.. 10 24 Kompositionens pH var 10,3 Vid användningstillfället tillsattes 90 g väte- peroxid, som alstrar 20 volymer.EXAMPLE 1 2 The following staining composition was prepared: The compound of Example 1 0.306 Paraphenylenediamine 0.307 The dihydrochloride of 4-N-β-methoxyethylamino- aniline 0.15 2-methylresorcin 0.405 2-methyl-5-N-β-hydroxyethylaminophenol 0.115 The dihydrochloride of (2,4-diamino) phenoxy- ethanol 0.106 2-amino-3-nitrophenol 0.203 Cetyl stearyl alcohol sold under the the name "ALFOL C16 / 18 E" by the company "CONDEA" 8 Cetyl stearyl sodium sulfate sold under the name "CIRE DE LANETTE E" by the company "RBNKEL" 0.5 Ethoxylated castor oil, sold below the name "CEMULSQL B" by the company "RHONE POULENC" 1 .øleyldietanolamide 1.5 The pentasodium salt "avdiethylenetriamine- pentaacetic acid, which is sold under in the name "MASQUOL DTPA" '2.5 ", Thioglycolic acid 0.5 _UHydroquinone «~, V _ 0,15 1¿Ammonl¿k «<22 ° së> - _ Å. '1 '11 í ° ¿v¿c: en, t111H,, _ _ “. > ¿., V, _ ,, ioo 9 9 l-Q lQQI-QW-QQ , -_ .. 10 24 The pH of the composition was 10.3 At the time of use, 90 g of hydrogen was added. peroxide, which produces 20 volumes.
Blandningen applicerades under 25 min vid 25°C på till 90 % naturligt vitt hår och gav håret efter sköljning och shamponering en antracitgrå färgning.The mixture was applied for 25 minutes at 25 ° C on to 90% natural white hair and gave the hair after rinsing and shampooing an anthracite gray stain.
Det är uppenbart att ovan angivna utföringsexempel på intet sätt är begränsande och att de kan föranleda alla önskvärda ändringar utan att ramen för uppfin- ningen därvid överskrides.It is obvious that the above-mentioned embodiments in no way restrictive and that they may cause all desirable changes without prejudice to the is thereby exceeded.
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| FR8014661A FR2486075A1 (en) | 1980-07-01 | 1980-07-01 | METHAPHENYLENEDIAMINES AND METHOD FOR THE PRODUCTION THEREOF, TINCTORIAL COMPOSITIONS CONTAINING SAME, AND METHOD FOR DYING THE SAME |
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| SE460787B true SE460787B (en) | 1989-11-20 |
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| JP (1) | JPS5744669A (en) |
| AR (1) | AR227050A1 (en) |
| AT (1) | AT380683B (en) |
| AU (1) | AU543206B2 (en) |
| BE (1) | BE889449A (en) |
| BR (1) | BR8104162A (en) |
| CA (1) | CA1168266A (en) |
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| DE (1) | DE3125705A1 (en) |
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| FR (1) | FR2486075A1 (en) |
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| FR2519251B1 (en) * | 1982-01-05 | 1985-11-22 | Oreal | TINCTORIAL COMPOSITION BASED ON PRECURSORS OF OXIDATION DYES AND N-SUBSTITUTED ORTHONITRANILINES COMPRISING AN ALCANOLAMINE AND SODIUM BISULFITE AND THEIR USE IN DYEING KERATIN FIBERS |
| FR2547300B1 (en) * | 1983-06-13 | 1986-04-18 | Oreal | NOVEL SUBSTITUTED METAAMINOPHENOLS, PROCESS FOR THEIR PREPARATION, TINCTORIAL COMPOSITIONS FOR HAIR CONTAINING THEM AND METHOD FOR DYEING HAIR |
| JPH0825858B2 (en) * | 1991-06-04 | 1996-03-13 | ホーユー株式会社 | Hair dye composition |
| FR2707487B1 (en) † | 1993-07-13 | 1995-09-08 | Oreal | A keratin fiber oxidation dye composition comprising a para-aminophenol, a meta-aminophenol and a metaphenylenediamine, and a dyeing process using such a composition. |
| FR2715296B1 (en) * | 1994-01-24 | 1996-04-12 | Oreal | Keratin fiber oxidation dyeing composition comprising a paraphenylenediamine, a metalphenylenediamine and a para-aminophenol or a meta-aminophenol, and dyeing process using such a composition. |
| FR2720275B1 (en) * | 1994-05-26 | 1996-07-05 | Oreal | Keratin fiber oxidation dyeing composition comprising a paraphenylenediamine derivative and a 6-hydroxy 1,4-benzoxazine, and dyeing process using such a composition. |
| FR2729564B1 (en) * | 1995-01-19 | 1997-02-28 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS AND DYE PROCESS USING THIS COMPOSITION |
| DE19826456A1 (en) * | 1998-06-13 | 1999-12-16 | Schwarzkopf Gmbh Hans | Novel 3,4-diaminophenol derivatives and their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1670969A (en) * | 1926-12-13 | 1928-05-22 | Firm Chemical Works Formerly S | 2-amino-4-nitrophenoxypropandiol and process of producing same |
| FR2362116A1 (en) * | 1976-08-20 | 1978-03-17 | Oreal | METAPHENYLENEDIAMINES AND TINCTORIAL COMPOSITIONS CONTAINING THEM |
-
1980
- 1980-07-01 FR FR8014661A patent/FR2486075A1/en active Granted
-
1981
- 1981-06-22 AT AT0274181A patent/AT380683B/en not_active IP Right Cessation
- 1981-06-26 PT PT73269A patent/PT73269B/en not_active IP Right Cessation
- 1981-06-29 DK DK287681A patent/DK150540C/en not_active IP Right Cessation
- 1981-06-29 AR AR285896A patent/AR227050A1/en active
- 1981-06-29 ES ES503491A patent/ES503491A0/en active Granted
- 1981-06-29 CH CH4277/81A patent/CH650246A5/en not_active IP Right Cessation
- 1981-06-30 AU AU72363/81A patent/AU543206B2/en not_active Expired
- 1981-06-30 SE SE8104072A patent/SE460787B/en not_active IP Right Cessation
- 1981-06-30 MX MX188102A patent/MX155064A/en unknown
- 1981-06-30 IT IT67905/81A patent/IT1144738B/en active
- 1981-06-30 CA CA000380936A patent/CA1168266A/en not_active Expired
- 1981-06-30 BR BR8104162A patent/BR8104162A/en unknown
- 1981-06-30 GB GB8120127A patent/GB2078747B/en not_active Expired
- 1981-06-30 DE DE3125705A patent/DE3125705A1/en not_active Withdrawn
- 1981-06-30 NL NL8103150A patent/NL8103150A/en not_active Application Discontinuation
- 1981-06-30 BE BE0/205266A patent/BE889449A/en not_active IP Right Cessation
- 1981-07-01 JP JP56101396A patent/JPS5744669A/en active Pending
- 1981-10-28 ES ES506626A patent/ES506626A0/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8104072L (en) | 1982-01-02 |
| BR8104162A (en) | 1982-03-16 |
| ES8301889A1 (en) | 1982-12-16 |
| BE889449A (en) | 1981-12-30 |
| PT73269B (en) | 1982-09-23 |
| JPS5744669A (en) | 1982-03-13 |
| AT380683B (en) | 1986-06-25 |
| DE3125705A1 (en) | 1982-03-18 |
| CH650246A5 (en) | 1985-07-15 |
| NL8103150A (en) | 1982-02-01 |
| ATA274181A (en) | 1985-11-15 |
| PT73269A (en) | 1981-07-01 |
| DK150540C (en) | 1988-01-11 |
| GB2078747B (en) | 1986-01-22 |
| GB2078747A (en) | 1982-01-13 |
| ES8205393A1 (en) | 1982-06-01 |
| AU7236381A (en) | 1982-09-16 |
| IT1144738B (en) | 1986-10-29 |
| AU543206B2 (en) | 1985-04-04 |
| ES503491A0 (en) | 1982-06-01 |
| DK287681A (en) | 1982-01-02 |
| DK150540B (en) | 1987-03-23 |
| FR2486075B1 (en) | 1983-03-11 |
| AR227050A1 (en) | 1982-09-15 |
| IT8167905A0 (en) | 1981-06-30 |
| CA1168266A (en) | 1984-05-29 |
| MX155064A (en) | 1988-01-22 |
| FR2486075A1 (en) | 1982-01-08 |
| ES506626A0 (en) | 1982-12-16 |
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