DE102021207098A1 - Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, einer farbgebenden Verbindung, eines Versiegelungsreagenz und eines alkalischen Vorbehandlungsmittels - Google Patents

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Publication number

DE102021207098A1

DE102021207098A1 DE102021207098.1A DE102021207098A DE102021207098A1 DE 102021207098 A1 DE102021207098 A1 DE 102021207098A1 DE 102021207098 A DE102021207098 A DE 102021207098A DE 102021207098 A1 DE102021207098 A1 DE 102021207098A1

Authority

DE

Germany

Prior art keywords

agent

group

acid

pigments

organic silicon

Prior art date

2021-07-06

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.)

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• 239000000463 material Substances 0.000 title claims abstract description 248
• 238000000034 method Methods 0.000 title claims abstract description 149
• 150000001875 compounds Chemical class 0.000 title claims abstract description 116
• 238000007789 sealing Methods 0.000 title claims abstract description 88
• 238000004040 coloring Methods 0.000 title claims abstract description 80
• 230000008569 process Effects 0.000 title claims description 40
• 150000003961 organosilicon compounds Chemical class 0.000 title description 9
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 560
• 239000000049 pigment Substances 0.000 claims abstract description 181
• 150000003377 silicon compounds Chemical class 0.000 claims abstract description 143
• 102000011782 Keratins Human genes 0.000 claims abstract description 86
• 108010076876 Keratins Proteins 0.000 claims abstract description 86
• 239000000982 direct dye Substances 0.000 claims abstract description 61
• 210000004209 hair Anatomy 0.000 claims abstract description 61
• 230000003113 alkalizing effect Effects 0.000 claims abstract description 59
• 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 51
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 49
• 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 47
• 150000004756 silanes Chemical class 0.000 claims abstract description 44
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 95
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 94
• 229920000642 polymer Polymers 0.000 claims description 92
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 88
• 239000000203 mixture Substances 0.000 claims description 76
• 239000003153 chemical reaction reagent Substances 0.000 claims description 57
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 33
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 239000002535 acidifier Substances 0.000 claims description 14
• 238000004806 packaging method and process Methods 0.000 claims description 14
• 239000001023 inorganic pigment Substances 0.000 claims description 13
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 12
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
• SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 10
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 9
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
• LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 229960003493 octyltriethoxysilane Drugs 0.000 claims description 4
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 161
• 229920001577 copolymer Polymers 0.000 description 96
• 235000010215 titanium dioxide Nutrition 0.000 description 91
• 235000013980 iron oxide Nutrition 0.000 description 75
• 239000010445 mica Substances 0.000 description 68
• 229910052618 mica group Inorganic materials 0.000 description 68
• -1 alkali metal cation Chemical class 0.000 description 66
• 239000004408 titanium dioxide Substances 0.000 description 50
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 48
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
• 238000004043 dyeing Methods 0.000 description 38
• WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 37
• 229920001519 homopolymer Polymers 0.000 description 35
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 32
• 229910000077 silane Inorganic materials 0.000 description 31
• 239000000758 substrate Substances 0.000 description 31
• IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 30
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 28
• 229910044991 metal oxide Inorganic materials 0.000 description 28
• 150000003254 radicals Chemical class 0.000 description 28
• 239000002253 acid Substances 0.000 description 26
• CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 23
• 229910052751 metal Inorganic materials 0.000 description 23
• 239000002184 metal Substances 0.000 description 23
• XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 23
• 239000000377 silicon dioxide Substances 0.000 description 22
• LQJVOKWHGUAUHK-UHFFFAOYSA-L disodium 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(N)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 LQJVOKWHGUAUHK-UHFFFAOYSA-L 0.000 description 21
• FPAYXBWMYIMERV-UHFFFAOYSA-L disodium;5-methyl-2-[[4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O FPAYXBWMYIMERV-UHFFFAOYSA-L 0.000 description 21
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 21
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
• HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 description 20
• 125000000129 anionic group Chemical group 0.000 description 20
• 229920001477 hydrophilic polymer Polymers 0.000 description 20
• 150000004706 metal oxides Chemical class 0.000 description 20
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 20
• UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 20
• 239000000975 dye Substances 0.000 description 19
• FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 19
• NDDLLTAIKYHPOD-ISLYRVAYSA-N (2e)-6-chloro-2-(6-chloro-4-methyl-3-oxo-1-benzothiophen-2-ylidene)-4-methyl-1-benzothiophen-3-one Chemical compound S/1C2=CC(Cl)=CC(C)=C2C(=O)C\1=C1/SC(C=C(Cl)C=C2C)=C2C1=O NDDLLTAIKYHPOD-ISLYRVAYSA-N 0.000 description 18
• VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 18
• GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 18
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 18
• 229940048053 acrylate Drugs 0.000 description 17
• SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 17
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• MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 16
• LMULDSDQRQVZMW-UHFFFAOYSA-N N-(5-chloro-2,4-dimethoxyphenyl)-4-[[5-(diethylsulfamoyl)-2-methoxyphenyl]diazenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(N=NC=2C3=CC=CC=C3C=C(C=2O)C(=O)NC=2C(=CC(OC)=C(Cl)C=2)OC)=C1 LMULDSDQRQVZMW-UHFFFAOYSA-N 0.000 description 16
• RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 16
• XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 16
• FHRUGNCCGSEPPE-UHFFFAOYSA-L disodium;2-(4,5-dibromo-3,6-dioxido-9h-xanthen-9-yl)benzoate;hydron Chemical compound [H+].[Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1C2=CC=C([O-])C(Br)=C2OC2=C(Br)C([O-])=CC=C21 FHRUGNCCGSEPPE-UHFFFAOYSA-L 0.000 description 16
• 239000002245 particle Substances 0.000 description 16
• GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 15
• XLTMWFMRJZDFFD-UHFFFAOYSA-N 1-[(2-chloro-4-nitrophenyl)diazenyl]naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl XLTMWFMRJZDFFD-UHFFFAOYSA-N 0.000 description 15
• JFMYRCRXYIIGBB-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)diazenyl]-n-[4-[4-[[2-[(2,4-dichlorophenyl)diazenyl]-3-oxobutanoyl]amino]-3-methylphenyl]-2-methylphenyl]-3-oxobutanamide Chemical compound C=1C=C(C=2C=C(C)C(NC(=O)C(N=NC=3C(=CC(Cl)=CC=3)Cl)C(C)=O)=CC=2)C=C(C)C=1NC(=O)C(C(=O)C)N=NC1=CC=C(Cl)C=C1Cl JFMYRCRXYIIGBB-UHFFFAOYSA-N 0.000 description 15
• QTSNFLIDNYOATQ-UHFFFAOYSA-N 2-[(4-chloro-2-nitrophenyl)diazenyl]-n-(2-chlorophenyl)-3-oxobutanamide Chemical compound C=1C=CC=C(Cl)C=1NC(=O)C(C(=O)C)N=NC1=CC=C(Cl)C=C1[N+]([O-])=O QTSNFLIDNYOATQ-UHFFFAOYSA-N 0.000 description 15
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• IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 15
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• JQNJCQYNSLCFAC-UHFFFAOYSA-N 3-hydroxy-N-(2-methylphenyl)-4-[(2,4,5-trichlorophenyl)diazenyl]naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C(N=NC=2C(=CC(Cl)=C(Cl)C=2)Cl)=C1O JQNJCQYNSLCFAC-UHFFFAOYSA-N 0.000 description 15
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• KWORKYDIARWARF-UHFFFAOYSA-N N-(4-chloro-2-methylphenyl)-4-[(4-chloro-2-methylphenyl)diazenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound Cc1cc(Cl)ccc1NC(=O)c1cc2ccccc2c(N=Nc2ccc(Cl)cc2C)c1O KWORKYDIARWARF-UHFFFAOYSA-N 0.000 description 15
• QDORUQCHIMQWMJ-UHFFFAOYSA-J calcium disodium 4-carboxy-5-chloro-2-[(2-oxidonaphthalen-1-yl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].[Ca++].Oc1ccc2ccccc2c1N=Nc1cc(C([O-])=O)c(Cl)cc1S([O-])(=O)=O.Oc1ccc2ccccc2c1N=Nc1cc(C([O-])=O)c(Cl)cc1S([O-])(=O)=O QDORUQCHIMQWMJ-UHFFFAOYSA-J 0.000 description 15
• 235000012730 carminic acid Nutrition 0.000 description 15
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• ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 15
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• 239000012860 organic pigment Substances 0.000 description 15
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• 238000003756 stirring Methods 0.000 description 15
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• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
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• FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 14
• 150000001413 amino acids Chemical class 0.000 description 14
• DYYWTFWWAKPJGZ-UHFFFAOYSA-L barium(2+) 4-[(2-hydroxynaphthalen-1-yl)diazenyl]-2-methylbenzenesulfonate Chemical compound [Ba++].Cc1cc(ccc1S([O-])(=O)=O)N=Nc1c(O)ccc2ccccc12.Cc1cc(ccc1S([O-])(=O)=O)N=Nc1c(O)ccc2ccccc12 DYYWTFWWAKPJGZ-UHFFFAOYSA-L 0.000 description 14
• CYHOWEBNQPOWEI-UHFFFAOYSA-L calcium 3-carboxy-1-phenyldiazenylnaphthalen-2-olate Chemical compound OC=1C(=CC2=CC=CC=C2C1N=NC1=CC=CC=C1)C(=O)[O-].OC=1C(=CC2=CC=CC=C2C1N=NC1=CC=CC=C1)C(=O)[O-].[Ca+2] CYHOWEBNQPOWEI-UHFFFAOYSA-L 0.000 description 14
• OVHKKOQGPOYPLY-UHFFFAOYSA-L calcium 3-oxido-4-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalene-2-carboxylate Chemical compound [Ca+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC(=C3O)C([O-])=O)=CC=C21 OVHKKOQGPOYPLY-UHFFFAOYSA-L 0.000 description 14
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