DE102016205616A1

DE102016205616A1 - 4,5-Diaminoimidazole als neue Oxidationsfarbstoffvorprodukte vom Entwicklertyp

4,5-Diaminoimidazole als neue Oxidationsfarbstoffvorprodukte vom Entwicklertyp Download PDF

Info

Publication number: DE102016205616A1
Authority: DE; Germany
Prior art keywords: amino; alkyl group; diamine; imidazole; group
Prior art date: 2016-04-05
Legal status : Withdrawn

Application number

DE102016205616.6A

Other languages

German (de)

English (en)

Inventor

Antje Gebert-Schwarzwälder

Helmut Giesa

Jan-Michael Schönebeck

Current Assignee

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

Priority date

2016-04-05

Filing date

2016-04-05

Publication date

2017-10-05

2016-04-05 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

2016-04-05 Priority to DE102016205616.6A priority Critical patent/DE102016205616A1/de

2017-03-29 Priority to FR1752607A priority patent/FR3049603A1/fr

2017-04-04 Priority to GB1705402.4A priority patent/GB2553171A/en

2017-04-04 Priority to US15/479,136 priority patent/US20170281501A1/en

2017-10-05 Publication of DE102016205616A1 publication Critical patent/DE102016205616A1/de

Status Withdrawn legal-status Critical Current

Links

239000002243 precursor Substances 0.000 title claims abstract description 45
230000003647 oxidation Effects 0.000 title claims abstract description 43
238000007254 oxidation reaction Methods 0.000 title claims abstract description 43
SNICMBLBGTVRFJ-UHFFFAOYSA-N 1h-imidazole-4,5-diamine Chemical class NC=1N=CNC=1N SNICMBLBGTVRFJ-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 84
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
239000001257 hydrogen Substances 0.000 claims abstract description 62
239000000203 mixture Substances 0.000 claims abstract description 60
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 43
150000002431 hydrogen Chemical class 0.000 claims abstract description 37
210000004209 hair Anatomy 0.000 claims abstract description 35
230000001590 oxidative effect Effects 0.000 claims abstract description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
239000000835 fiber Substances 0.000 claims abstract description 25
125000003118 aryl group Chemical group 0.000 claims abstract description 19
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
239000003581 cosmetic carrier Substances 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
-1 1-ethyl-4-N-methyl-1H-imidazole-4,5-diamine 4-N-ethyl-1H-imidazole-4,5-diamine 4-N-ethyl-1-methyl-1H-imidazole-4,5-diamine 1,4-N-diethyl-1H-imidazole-4,5-diamine Chemical compound 0.000 claims description 86
239000003795 chemical substances by application Substances 0.000 claims description 67
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 38
WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 claims description 23
BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 claims description 23
ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 23
BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 22
XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 claims description 22
MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 claims description 22
ATCBPVDYYNJHSG-UHFFFAOYSA-N 6-methoxy-2-n-methylpyridine-2,3-diamine Chemical compound CNC1=NC(OC)=CC=C1N ATCBPVDYYNJHSG-UHFFFAOYSA-N 0.000 claims description 22
DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims description 22
SYRZWFBWUASJJI-UHFFFAOYSA-N 3-amino-2,4-dichlorophenol Chemical compound NC1=C(Cl)C=CC(O)=C1Cl SYRZWFBWUASJJI-UHFFFAOYSA-N 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 12
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ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 8
OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 claims description 7
KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 4
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ORVPXPKEZLTMNW-UHFFFAOYSA-N 1h-indol-7-ol Chemical compound OC1=CC=CC2=C1NC=C2 ORVPXPKEZLTMNW-UHFFFAOYSA-N 0.000 claims description 4
OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 claims description 4
JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 claims description 4
UBTQTHRBXZXHAD-UHFFFAOYSA-N 2,3-dihydro-1h-indol-7-ol Chemical compound OC1=CC=CC2=C1NCC2 UBTQTHRBXZXHAD-UHFFFAOYSA-N 0.000 claims description 4
BXBOXUNPNIJELB-UHFFFAOYSA-N 2,6-dimethoxypyridine-3,5-diamine Chemical compound COC1=NC(OC)=C(N)C=C1N BXBOXUNPNIJELB-UHFFFAOYSA-N 0.000 claims description 4
FZQCIWKUHYZRGY-UHFFFAOYSA-N 4-(2-methoxyethoxy)-5-methylbenzene-1,3-diamine Chemical compound COCCOC1=C(C)C=C(N)C=C1N FZQCIWKUHYZRGY-UHFFFAOYSA-N 0.000 claims description 4
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 4
YGRFRBUGAPOJDU-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-2-methylphenol Chemical compound CC1=CC=C(NCCO)C=C1O YGRFRBUGAPOJDU-UHFFFAOYSA-N 0.000 claims description 4
KIEGFAYDOKCBOK-UHFFFAOYSA-N 6-hydroxy-4,5-dimethyl-1h-pyridin-2-one Chemical compound CC1=CC(=O)NC(O)=C1C KIEGFAYDOKCBOK-UHFFFAOYSA-N 0.000 claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 claims description 4
SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 claims description 3
WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 claims description 3
239000001294 propane Substances 0.000 claims description 3
SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 claims 1
DCBCSMXGLXAXDM-UHFFFAOYSA-N 3-aminophenol;hydrochloride Chemical compound [Cl-].[NH3+]C1=CC=CC(O)=C1 DCBCSMXGLXAXDM-UHFFFAOYSA-N 0.000 claims 1
MNOIKXJFUJLVNO-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O.CC1=CC=C(N)C=C1O MNOIKXJFUJLVNO-UHFFFAOYSA-N 0.000 claims 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
PSIPDGUBFJOSGE-UHFFFAOYSA-N n-(2-methoxyethoxy)-3-methylaniline Chemical compound COCCONC1=CC=CC(C)=C1 PSIPDGUBFJOSGE-UHFFFAOYSA-N 0.000 claims 1
125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
239000000975 dye Substances 0.000 description 45
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229960001755 resorcinol Drugs 0.000 description 23
DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 22
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
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238000000034 method Methods 0.000 description 6
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150000001412 amines Chemical class 0.000 description 5
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MHANKXPPKNGTID-UHFFFAOYSA-N 1,3-bis(2,5-diaminophenoxy)propan-2-ol Chemical compound NC1=CC=C(N)C(OCC(O)COC=2C(=CC=C(N)C=2)N)=C1 MHANKXPPKNGTID-UHFFFAOYSA-N 0.000 description 4
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