NO803288L - NEW CONNECTOR COMPONENTS FOR OXYDATION HAIR COLORS, THEIR MANUFACTURING AND USE, AND HAIR COLORING AGENTS CONTAINING THESE - Google Patents
NEW CONNECTOR COMPONENTS FOR OXYDATION HAIR COLORS, THEIR MANUFACTURING AND USE, AND HAIR COLORING AGENTS CONTAINING THESEInfo
- Publication number
- NO803288L NO803288L NO803288A NO803288A NO803288L NO 803288 L NO803288 L NO 803288L NO 803288 A NO803288 A NO 803288A NO 803288 A NO803288 A NO 803288A NO 803288 L NO803288 L NO 803288L
- Authority
- NO
- Norway
- Prior art keywords
- hair
- residue
- acetamido
- hydroxypropyl
- substituted
- Prior art date
Links
- 239000000118 hair dye Substances 0.000 title claims description 21
- 238000007254 oxidation reaction Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003086 colorant Substances 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 11
- MACQTEBZCXPXFX-UHFFFAOYSA-N n-[5-nitro-2-(oxiran-2-ylmethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1OCC1OC1 MACQTEBZCXPXFX-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 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 claims 1
- 238000002360 preparation method Methods 0.000 description 30
- 239000013078 crystal Substances 0.000 description 19
- 230000008018 melting Effects 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- -1 2,4-diaminophenol ethers Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 10
- 238000003776 cleavage reaction Methods 0.000 description 9
- 230000007017 scission Effects 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 2
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000037308 hair color Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- NXVHEHXRZVQDCR-UHFFFAOYSA-N 1-n,1-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1C NXVHEHXRZVQDCR-UHFFFAOYSA-N 0.000 description 1
- HQCHAOKWWKLXQH-UHFFFAOYSA-N 2,6-Dichloro-para-phenylenediamine Chemical compound NC1=CC(Cl)=C(N)C(Cl)=C1 HQCHAOKWWKLXQH-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- BKVGXVRTYYZVJL-UHFFFAOYSA-N 2-[2-(4-aminophenyl)hydrazinyl]ethanol Chemical compound OCCNNC1=CC=C(C=C1)N BKVGXVRTYYZVJL-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- MPUYRZSQOVOWER-UHFFFAOYSA-N 2-chloro-6-methylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(Cl)=C1N MPUYRZSQOVOWER-UHFFFAOYSA-N 0.000 description 1
- AJKKPMXOCLIQCH-UHFFFAOYSA-N 3-(2,4-diaminophenoxy)propane-1,2-diol;dihydrochloride Chemical compound Cl.Cl.NC1=CC=C(OCC(O)CO)C(N)=C1 AJKKPMXOCLIQCH-UHFFFAOYSA-N 0.000 description 1
- CSGNEKGWOJHKOI-UHFFFAOYSA-N 4-(4-azaniumyl-n-butylanilino)butane-1-sulfonate Chemical compound OS(=O)(=O)CCCCN(CCCC)C1=CC=C(N)C=C1 CSGNEKGWOJHKOI-UHFFFAOYSA-N 0.000 description 1
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 description 1
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 description 1
- 101100517284 Caenorhabditis elegans nsun-1 gene Proteins 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010043183 Teething Diseases 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Oppfinnelsens gjenstand er nye 1-substituerte 2-.hydroksyprpyl-r (2 , 4--diaminof enoleter ) med den generelle formel The object of the invention is new 1-substituted 2-hydroxypropyl-r(2,4-diaminophenol ethers) with the general formula
hvori R betyr en av restene -NHCjH^, -NHC^H^, -NHCHgC^H^, -N(C2H^)(C^H^), - OE, -0C2H^, morfolin- eller piperidinrest. wherein R means one of the residues -NHCjH^, -NHC^H^, -NHCHgC^H^, -N(C2H^)(C^H^), -OE, -OC2H^, morpholine or piperidine residue.
Fremstillingen av de nye 1 - substituerte 2-hydroksypropyl-(2,4-diaminofenoleter) foregår i. flere trinn etter kjente fremgangsmåter i organisk kjemi. I første rekke settes i første trinn 2-acetamido-4,-nitrofenol med epiklorhydrin til l(2-ace-tamido - /+ -nitr of enoksy )-2, 3-epoksypropan. Dertil innføres i annet trinn omsetning med et amin, vann eller alkohol under åpning av oksyranringene og- dannelse av en hydroksylgruppe i 2-stilling av propylrestene i 3-stilling av propylresten den ønskede rest R. Det tredje trinn avspaltes deretter den for maskering av aminogruppen tjenende acetylrest,,hvoretter i 4--trinn ved katalystisk hydroginéring overføres nitrogruppen i aminogruppen, og således fåes det ønskede nye produkt. Reak-sjonen forløper derved etter følgende skjema idet R. har overnevnte betydning: The production of the new 1-substituted 2-hydroxypropyl-(2,4-diaminophenol ethers) takes place in several steps according to known methods in organic chemistry. In the first place, in the first step, 2-acetamido-4,-nitrophenol is added with epichlorohydrin to 1(2-acetamido - /+ -nitr of enoxy )-2, 3-epoxypropane. In addition, reaction with an amine, water or alcohol is introduced in the second step, opening the oxirane rings and forming a hydroxyl group in the 2-position of the propyl residues in the 3-position of the propyl residue, the desired residue R. In the third step, it is then cleaved off to mask the amino group serving acetyl residue, after which in 4 steps by catalytic hydrogenation the nitro group is transferred to the amino group, and thus the desired new product is obtained. The reaction thereby proceeds according to the following scheme, with R. having the above-mentioned meaning:
Ytterligere gjenstander for oppfinnelsen er anvendelsen av de nye 1-substituerte 2-hydroksypropyl-(2,4 diaminofenoleter) som sådanne, eller i form av deres salter med uorganiske eller organiske syrer som koblerkomponenter i oksydasjonshårfarver, samt h.årfarvemidler som inneholder de nye 1-substituerte 2-hydroksypropyl- (2,4-diaminofenoleter) respektiv deres salter. Further objects of the invention are the use of the new 1-substituted 2-hydroxypropyl-(2,4 diaminophenol ethers) as such, or in the form of their salts with inorganic or organic acids as coupling components in oxidation hair dyes, as well as hair dyes containing the new 1 -substituted 2-hydroxypropyl-(2,4-diaminophenol ether) and their salts respectively.
For farving av hår, spiller de såkalte oksydasjonsfarver som oppstår ved oksydativ kobling av en frem-kallerkomponent med en koblerkomponent på grunn av deres intense farver og gode ekthetsegenskaper en foretrukket rolle. Som fremkaller stoffer anvendes vanligvis nitrogen-'baser som p-f enylendiaminderivater , diaminopyridin , 4 aminopyrazolonderivater, heterocykliske hydrazoner. Som såkalte koblerkomponenter nevnes m-fenylendiaminderivater, fenoler, naftoler, resorcinderivater og pyrazoloner. For dyeing hair, the so-called oxidation dyes which occur by oxidative coupling of a developer component with a coupling component, due to their intense colors and good authenticity properties, play a preferred role. Nitrogen bases such as p-phenylenediamine derivatives, diaminopyridine, 4-aminopyrazolone derivatives, heterocyclic hydrazones are usually used as developer substances. As so-called coupling components, m-phenylenediamine derivatives, phenols, naphthols, resorcin derivatives and pyrazolones are mentioned.
Godeoksydasjonshårfarvestoffkomponenter må i første rekke oppfylle følgende forutsetninger: De må ved den bksydative kobling med de eventuelle fremkaller- resp. koblerkomponenter danne de 'ønskede farvenyanser i tilstrekkelig intensitet. De må videre ha en ut- merket til meget god opptrekningsevne på menneskehår, og dé skal dessuten i toksikologisk og dermatologisk henseende være ufarlig. Good oxidation hair dye components must first of all fulfill the following conditions: They must by the boxydative coupling with the possible inducer- or connector components form the 'desired color shades in sufficient intensity. They must also have an out- marked for very good pulling power on human hair, and it must also be harmless from a toxicological and dermatological point of view.
Det besto, derfor søkning etter brukbare oksyda-sj onshårf arve stoff er den oppgave å finne egnede komponenter som oppfyller de overnevnte' forutsetninger på optimal måte. It was, therefore, the search for usable oxidation dyed materials, the task is to find suitable components that fulfill the above-mentioned prerequisites in an optimal way.
Det er nå funnet at man kommer til oksydasjonshårfarver som i spesiell høy gra.d oppfyller de. nevnte krav når man som koblerkomponenter anvender 1-substituerte 2-hydroksyprppyl-(2 , 4 diaminof enoleter ) med den generelle formel It has now been found that you arrive at oxidation hair colors which fulfill them to a particularly high degree. mentioned requirements when using 1-substituted 2-hydroxypropyl-(2,4 diaminophenol ethers) with the general formula as coupling components
hvori R betyr en av restene -NHC^, -NHC^,. -NHCHgCgH^ -N-(C2H5) (C6H5), -0H, -0C.2H5>morfolin eller piper idinre st, samt deres salter med uorganiske eller organiske syrer i kombinasjon med vanlige, fremkallerstoffer. wherein R means one of the residues -NHC^, -NHC^,. -NHCHgCgH^ -N-(C2H5) (C6H5), -0H, -0C.2H5>morpholine or piper idinre st, as well as their salts with inorganic or organic acids in combination with common developer substances.
Hårfarvemidler på basis av oksydasjonsfarverHair dyes based on oxidation dyes
med et innhold av 1-substituert 2-hydroksypropyl-(2,4-diaminofenoleter) med den generelle formel with a content of 1-substituted 2-hydroxypropyl-(2,4-diaminophenol ether) of the general formula
hvori R har overnevnte betydning, samt ders salter med uorganiske eller organiske syrer, som koblerkomponenter og de i oksydasjonshårfarver vanlige fremkallerstoffer er følgelig spesielt verdifulle sammensetninger på området oksydasjonshårfarver. in which R has the above meaning, as well as its salts with inorganic or organic acids, as coupling components and the developers common in oxidation hair dyes are consequently particularly valuable compositions in the field of oxidation hair dyes.
Ved deres anvendelse som koblerkomponenter, gir forbindelsen ifølge oppfinnelsen med de vanligvis for oksyda-sj onhårf arving anvendte f remkaller stof f er .meget intense, fra turkis til mørkblå rekkende farvetoner, og er således en vesentlig berikelse av de oksydative hårfarve muligheter. Dess-. uten utmerker de 1-substituerte 2-hydroksypropyl - (2 , 4--diamino - fenoleter). ifølge oppfinnelsen seg meget gode ekthetsegenskaper av de dermed oppnådde farvinger med en god oppløselig-het i vann, en god lagringsstabilitet, og toksykologisk, samt When used as coupling components, the compound according to the invention with the developer substances usually used for oxidative hair dyeing gives very intense color tones ranging from turquoise to dark blue, and is thus a significant enrichment of the oxidative hair dyeing possibilities. Its-. without, the 1-substituted 2-hydroxypropyl - (2, 4--diamino - phenol ethers) are distinguished. according to the invention, very good authenticity properties of the dyes thus obtained with a good solubility in water, a good storage stability, and toxicologically, as well
dermatologisk ufarlighet.dermatological harmlessness.
De ifølge, oppfinnelsen som koblerkomponenter anvendbare 1-substituerte 2-hydroksypropyl - (2 , 4--diamino-f enoleter)ka<!>n anvendes enten som sådanne eller i form av deres salter med uorganiske eller organsike syrer, som eksempelvis klorider, sulfater, fosfater, acetater, propionater, lactater, citrater. According to the invention, the 1-substituted 2-hydroxypropyl - (2, 4--diamino-phenol ether) usable as coupling components can be used either as such or in the form of their salts with inorganic or organic acids, such as chlorides, sulphates, phosphates, acetates, propionates, lactates, citrates.
Som koblerkomponenter som kan anvnendes ifølge oppfinnelsen, er det å nevné' 1 -(2,4-diaminofenoksy)-3-anilino-propanol-2, 1 -(2, 4-dia.minofenoksy) -3-bensylaniino-propanol.-2, 1- (2,4--diaminofenoksy)-3 - (N-etylanilino )-propanol-2, 1 -(2,4-diaminof enoksy) -3-etoksypropanol-2 , 1 - (2 , 4.-diaminof enoksy ) -3- etylamino -propanol-2, 1-(2,4.-diaminofenoksy)-3-morfolino-propa.nol-2, 1 - (2 , 4,-diaminof enoksy )-2, 3-propandiol, 1 - (2 , 4- - diaminofenoksy)-3-piperidino-propanol-2, samt deres salter med uorganiske eller organiske syrer. As coupling components which can be used according to the invention, it is worth mentioning '1-(2,4-diaminophenoxy)-3-anilino-propanol-2, 1-(2,4-dia.minophenoxy)-3-benzylaniino-propanol.- 2,1-(2,4-diaminophenoxy)-3- (N-ethylanilino)-propanol-2,1-(2,4-diaminophenoxy)-3-ethoxypropanol-2,1-(2,4- diaminophenoxy )-3- ethylamino -propanol-2, 1-(2,4.-diaminophenoxy)-3-morpholino-propa.nol-2, 1 - (2 , 4,-diaminophenoxy )-2, 3-propanediol , 1 - (2, 4- - diaminophenoxy)-3-piperidino-propanol-2, as well as their salts with inorganic or organic acids.
Som eksempler for fremkallerkomponenter som er anvendbare i hårfarvemidlene ifølge oppfinenlsen' er det å an-føre primære aromatiske aminer, med en ytterligere p-stilling befinnende funksjonell gruppe som p-fenylendiamin, p-toluylendiamin, p-aminofenol, n-metyl-p-fenylendiamin, N,N-dimetyl-p-fenylendiamin, N,N-dietyl-2-metyl-p-fenylendiamin, N-etyl-N-hydroksyetyl-p-fenylendiamin, klor-p-fenylendiamin,N,N-bi s hydroksyetylamino-p-fenylendiamin, metoksy-p-fenylendiamin, 2- klor-, 2,6 diklor-p-fenylendiamin, 2-klor-6-brom-p-fenylen-. diamin, 2-klor-6-metyl-p-fenylendiamin, 6-metoksy-p-fenylendiamin, andre forbindelser av nevnte type som videre har en eller flere funksjonelle grupper som OH-grupper, NR^-grupper, NHR-grupper, NRg-grupper, idet R betyr en alkyl- eller hydroksy-alkylrest med 1 til U karbonatomer, videre diaminopyridinderi-vater, heterocykli ske hydrazonderivater sorn 1-metyl-pyrroli-don-,(2)-hydrazon, 4-aminopyrazolonderivater som 4-amino-1-fenyl-3-karbarnoylpyrazolon-5, W-butyl-N-sulfobutyl-p-fenylendiamin, tetraaminopyrimidiner som 2,4>5>6-tetraaminopyrimi-din, i, 5 > -diamin o-2, 6-bismetylamiriopyrimidin, 2, 5-diamino-4-di etylamino - 6 - me tyl am inopyrimidin, 2, 4., 5.triamino-6-dimetyl- aminopyrimidin, 2,4.5-triamino-6-piperidino-pyrimidin, 2,4-,5-triamino-6-anilino-pyrimidin, 2, 4.» 5-triaraino-6-morf olino-pyrimidin, 2, 4» 5-triamino-6 -/)-hydroksy-etylamino-pyrimidin. Examples of developer components that can be used in the hair dyes according to the invention are primary aromatic amines with a further p-position functional group such as p-phenylenediamine, p-toluylenediamine, p-aminophenol, n-methyl-p- phenylenediamine, N,N-dimethyl-p-phenylenediamine, N,N-diethyl-2-methyl-p-phenylenediamine, N-ethyl-N-hydroxyethyl-p-phenylenediamine, chloro-p-phenylenediamine,N,N-bis hydroxyethylamino-p-phenylenediamine, methoxy-p-phenylenediamine, 2-chloro-, 2,6 dichloro-p-phenylenediamine, 2-chloro-6-bromo-p-phenylene-. diamine, 2-chloro-6-methyl-p-phenylenediamine, 6-methoxy-p-phenylenediamine, other compounds of the aforementioned type which further have one or more functional groups such as OH groups, NR^ groups, NHR groups, NRg -groups, where R means an alkyl or hydroxyalkyl residue with 1 to U carbon atoms, further diaminopyridine derivatives, heterocyclic hydrazone derivatives such as 1-methyl-pyrrolidone-,(2)-hydrazone, 4-aminopyrazolone derivatives such as 4-amino -1-phenyl-3-carbarnoylpyrazolone-5, N-butyl-N-sulfobutyl-p-phenylenediamine, tetraaminopyrimidines such as 2,4>5>6-tetraaminopyrimidine, i,5>-diamine o-2,6-bismethylamiriopyrimidine . ,5-triamino-6-anilino-pyrimidine, 2, 4.'' 5-triaraino-6-morph olino-pyrimidine, 2, 4» 5-triamino-6 -/)-hydroxy-ethylamino-pyrimidine.
Koblerkomponentene ifølge oppfinnelsen gir vedThe connector components according to the invention provide
siden av andre farvenyariser, med tilsvarende fremkallerstoffer også mørkeblått til svartblå, spesielt intense hår-farvinger som utmerker seg ved overordenelige lyseektheter. in addition to other color nuances, with corresponding developer substances also dark blue to black blue, especially intense hair dyes that are distinguished by extraordinary lightfastness.
De er derfor også spesielt viktige som nyanseringskomponenter foroppnåelse av mest mulig kraftig og til de naturlige hår-farvenyanser mest mulig svarende farvetoner, da det ved inn-stilling av naturlige farvenyanser ofte fremkommer vanskelig-heter under hjelp av blåkoblerkornponenter. They are therefore also particularly important as tinting components for achieving the strongest possible color tones and the closest possible match to the natural hair color shades, as difficulties often arise when setting natural color shades with the help of blue coupler grain components.
I hårfarvemidlene ifølge oppfinnelsen, anvendes koblerkomponentene vanligvis i omtrent molare mengder, In the hair dyes according to the invention, the coupling components are usually used in approximately molar amounts,
referert til de anvendte fremkallerstoffer. Men skjønt ogsåreferred to the developers used. But though also
den molare anvendelse har vist seg som hensiktsmessig, så er det imidlertid ikke uheldig når koblerkomponentene kommer til anvendelse i et visst overkudd, eller underskudd. the molar application has proven to be appropriate, so it is not unfortunate, however, when the coupler components are used in a certain surplus or deficit.
Det er videre ikke nødvendig at fremkallerkomponentene av kobl erstoffet er enhetlige produkter, men så vel fremkallerkomponentene kan være blandinger av de i følge oppfinnelsen anvendbare fremkallerforbindelser, som også kobler-stoffene være blandinger av de ifølge oppfinnelsen anvendbare 1-substituerte 2-hydroksypropyl-(2,4-diaminofenoleter). Furthermore, it is not necessary that the developer components of the coupling agent are uniform products, but the developer components can also be mixtures of the developer compounds that can be used according to the invention, as also the coupling substances can be mixtures of the 1-substituted 2-hydroxypropyl-(2 ,4-diaminophenol ether).
Dessuten kan hårfarvemiddelet ifølge oppfinnelsen inneholde eventuelt vanlige direkttrekkende farvestoffer i blanding, hvis dette er nødvendig for oppnåelse av visse farvenyanser. In addition, the hair dye according to the invention may optionally contain common direct dyes in the mixture, if this is necessary to achieve certain color shades.
Den oksydative kobling, d.v.s fremkallingen av farvingen, kan prinsippielt foregå som ved andre oksydasjons-hårf arve stof f er også ved hjelp av luftoksygen. Hensiktsmessig anvendes 'imidlertid kjemiske oksydasjonsmidler. Som sådanne kommer det speseilet i betraktning hydrogenperoksyd eller dets tillæringsprodukter til urinstoff, melamin og natriumborat, samt blandinger av slike hydrogenperoksyd-til-læringsforbindelser med kaliumperoksyddisulfat. The oxidative coupling, i.e. the development of the colouring, can in principle take place as with other oxidation-dyeing substances, also with the help of atmospheric oxygen. However, chemical oxidizing agents are used expediently. As such, hydrogen peroxide or its formation products for urea, melamine and sodium borate, as well as mixtures of such hydrogen peroxide formation compounds with potassium peroxide disulphate, come into particular consideration.
Hårfarvemidlene ifølge oppfinnelsen, innarbeides for anvendelse i tilsvarende kosmetiske tilberedninger som kremer, emulsjoner, geleer eller også enkle oppløsninger og blandes umiddelbart før anvendelsen på håret med et av de nevnte oksydasjonsmidler. Konsentrasjonen av slike farve-aktive tilberedninger av kobler- fremkallerkombinasjoner, utgjør 0,2 til 5 vekt%, fortrinnsvis 1 til 3 vekt%. For fremstilling av kremer, emulsjoner eller geleer, blandes farvestoffkomponentene med de for slike preparater vanlig ytterligere betanddeler. Som slike ekstra bestanddeler er eksempelvis å'nevne fukte- eller emulgeringsmidler av anio-niske eller ikke-ionogeniske typer som alkylbenzolsulfonater, f ettalkohol sulf at er, alkyl sulf onater , f ettsyrealkanolamider-, tillæringsprodukter av etylenoksyd til fettalkoholer, fortykning smidler som metylcellulose, stivelse, høyere'fettalkoholer, parafinolje, fettsyrer, videre parfymeolje og hårpleiemidler som pantotensyre og cholestrol. De nevnte tilsetning s stof f er innarbeides derved i for disse formål vanlige mengder, som eksempelvis fukte- emulgeringsmidler i konsen-trasjoner fra 0,5 til 30 vekt%, og fortykning smi dier i kon-sentrasjoner fra 0,1 til 25 vekt%, hver gang referert til den samlede tilberedning. The hair dyes according to the invention are incorporated for use in corresponding cosmetic preparations such as creams, emulsions, gels or also simple solutions and are mixed immediately before application to the hair with one of the aforementioned oxidizing agents. The concentration of such dye-active preparations of coupler-developer combinations amounts to 0.2 to 5% by weight, preferably 1 to 3% by weight. For the production of creams, emulsions or gels, the dye components are mixed with the additional teething parts common for such preparations. Such additional ingredients include, for example, wetting or emulsifying agents of anionic or non-ionic types such as alkyl benzene sulphonates, fatty alcohol sulphates, alkyl sulphonates, fatty acid alkanolamides, conversion products of ethylene oxide to fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, further perfume oil and hair care agents such as pantothenic acid and cholestrol. The aforementioned additives are thereby incorporated in amounts customary for these purposes, such as wetting emulsifiers in concentrations from 0.5 to 30% by weight, and thickening agents in concentrations from 0.1 to 25% by weight , each time referring to the overall preparation.
Anvendelsen av hårfa.rvemiddelet ifølge oppfinnelsen kan uavhengig.av om det dreier seg om oppløsninger , emulsjoner, kremer eller geleer, foregå i svakt surt, nøytralt eller spesielt alkalisk miljø, ved en pH-verdi fra 8 - 10 Anvendelsestemperaturene beveger seg derved i området fra 15 til 4.0°C. Etter en innvirkningstid på ca. 30 minutter, fjernes hårfarve middelet av håret som skal farves ved skylling. Heretter ettervaskes håret med e-n mild shampo, og tørkes. The application of the hair dye agent according to the invention can, regardless of whether it concerns solutions, emulsions, creams or gels, take place in a slightly acidic, neutral or particularly alkaline environment, at a pH value of 8 - 10. The application temperatures thereby move in the range from 15 to 4.0°C. After an impact time of approx. 30 minutes, the hair dye is removed from the hair to be dyed by rinsing. The hair is then washed with a mild shampoo and dried.
De med hårfarvemidlene ifølge oppfinnelsen oppnådde farvinger, spsielt også blåtonene, viser under anvende-Ise av forskjellige fremkaller- og koblekomponenter spesielt intense farvenyanser. De oppnådde farvinger har gode lys-vaske- og friksjonsekthetsegenskaper, og lar , seg lett igjen fjerne med reduksjonsmidler. The colors obtained with the hair dyes according to the invention, especially the blue tones, show particularly intense color shades during the use of various developer and coupling components. The dyes obtained have good light-washing and friction fastness properties, and can easily be removed again with reducing agents.
Oppfinnelsen skal forklares nærmere ved hjelp av noen ikke-begrensede eksempler. The invention will be explained in more detail by means of some non-limiting examples.
EksemplerExamples
I første rekke omtales nedenfor fremstillingen av 1- substituerte 2-hydroksypropyl-(2, 4-diamino-fenolester) ifølge oppfinnelsen. First of all, the preparation of 1-substituted 2-hydroxypropyl-(2,4-diamino-phenol esters) according to the invention is described below.
A. 1 -(2,4-diaminofenoksy)-3-etylamino-propanol - 2 - trihydroklorid - 1. trinn: Fremstilling■av 1- (2-acetamido-4-nitrofenoksy) A. 1 -(2,4-diaminophenoxy)-3-ethylamino-propanol - 2 - trihydrochloride - 1st step: Preparation of 1-(2-acetamido-4-nitrophenoxy)
-2,3-epoksypropan.-2,3-epoxypropane.
1-4-7f 5 g acetamido-4--nitrof enol ble omrørt med 600 ml epiklorhydrin og 750 ml 1,1 n-natronlut 1 4-8 timer ved ca. 20°C. : Oppløsningen ble filt-rert, og omrørt, noen timer ved ca. 20UC. Det utskilte produkt bel frasuget og tørket i vakuum. Det dannede 1 -(2-acetamido-4--nitr of enoksy)-2 , 3-epoksypropan smelter ved 14-1 - 143°C. 1-4-7f 5 g of acetamido-4-nitroph enol was stirred with 600 ml of epichlorohydrin and 750 ml of 1,1 n-sodium hydroxide for 1 4-8 hours at approx. 20°C. : The solution was filtered and stirred for a few hours at approx. 20UC. The separated product was sucked off and dried in vacuum. The formed 1 -(2-acetamido-4-nitr of enoxy)-2,3-epoxypropane melts at 14-1 - 143°C.
2. trinn: Fremstilling av 1 -(2-acetamido-4-nitrofenoksy) -3-e-tylamino-propnaol-2. 8 g (0,03 mol) 1-(2-acetamido-4-nitrofenoksy)-2, 3-epoksyprop.an ble omrørt emd 85 g (0,94- mol) etylamin ( 50%- ±g vandig oppløsning) i 5 timer ved ca. 20°C. Det utsilte pr.odukt ble frasugd og ettervasket med vann. Etter tørking får man 1-(2-acetamido-4--ni tr of enoksy )-3-etylamino-pr opa-nol-2-med et smeltepunkt på 168 - 170°C. 3. trinn: Fremstilling av 1 - (2-amino-4--nitrof enoksy )-3-etylaminopropanol -2-hydroklorid. 6,1 g 1-(2-acetamido-4-nitrofenoksy)-2,3-p^opanol-2 ble kokt med 80, ml 2n-sal.tsyre i 2,5 timer under tilbakeløp. Oppløsningen ble inndampet til tørr-het. Det dannede 1-(2-amino-4-nitrofenoksy)-3-etylaminopropanol-2^hydroklorid smelter ved 90 - 95°C. 4. trinn: Fremstilling av, 1 - (2, 4-diaminof enoksy )-3-e tyl amino-propanol-2-trihydroklorid. 2nd step: Preparation of 1-(2-acetamido-4-nitrophenoxy)-3-e-tylamino-propnaol-2. 8 g (0.03 mol) 1-(2-acetamido-4-nitrophenoxy)-2, 3-epoxypropane was stirred with 85 g (0.94 mol) ethylamine (50% ± g aqueous solution) in 5 hours at approx. 20°C. The precipitated product was sucked off and washed with water. After drying, 1-(2-acetamido-4-nitrofenoxy)-3-ethylamino-propanol-2- with a melting point of 168 - 170°C is obtained. 3rd step: Preparation of 1 - (2-amino-4-nitrophenoxy)-3-ethylaminopropanol -2-hydrochloride. 6.1 g of 1-(2-acetamido-4-nitrophenoxy)-2,3-propanol-2 was boiled with 80 ml of 2n-hydrochloric acid for 2.5 hours under reflux. The solution was evaporated to dryness. The formed 1-(2-amino-4-nitrophenoxy)-3-ethylaminopropanol-2^hydrochloride melts at 90 - 95°C. 4th step: Preparation of, 1 - (2, 4-diaminophenoxy)-3-ethylamino-propanol-2-trihydrochloride.
6,1 g 1-(2-amino-4-nitrofenoksy)-3-étyl-aminopro-panpl-2-hydroklorid ble hydroginert katalytisk i 50 ml etanoli .nærvær av 5% palladium på kull. 6.1 g of 1-(2-amino-4-nitrophenoxy)-3-ethyl-aminopropanpl-2-hydrochloride was hydrogenated catalytically in 50 ml of ethanol in the presence of 5% palladium on charcoal.
Etter avsluttet hydrogenopptak, ble det atskilt fra katalysatoren. Oppløsningen ble surgjort med konsentrert saltsyre og inndampet til tørrhet. Den ønskede forbindelse 1 -(2r4-diaminofenoksy)-3-etylamino-propanol-2-trihydroklorid ble dannet i form av hvite krystaller som smeltet ved 95°C under spalting. After completion of hydrogen uptake, it was separated from the catalyst. The solution was acidified with concentrated hydrochloric acid and evaporated to dryness. The desired compound 1-(2R4-diaminophenoxy)-3-ethylamino-propanol-2-trihydrochloride was formed in the form of white crystals which melted at 95°C with cleavage.
B. 1-(2,4 diaminofenoksy)-3-piperidino-propanol-2-trihydroklorid. 1 . trinn: I første trinn ble det tilsvarende første trinn av A fremstillet 1 - (2-acetamido-4-nitrofenoksy) 2,3-epoksypropan. 2. trinn: Fremstilling ;av 1 - (2-acetamido-4.-nitrof enoksy)-3-piperidino-propanol-2. 8 g (0,03 mol) 1 -(2-acetaraido-4-nitrofenoksy)-2, 3-epoksypropan'ble omsatt med' 38,3 g (0,45 mol) piperidin tilsvarende angivelser annet trinn A. Den dannede gule olje ble videre forarbeidet i tredj e.trinn. B. 1-(2,4-diaminophenoxy)-3-piperidino-propanol-2-trihydrochloride. 1. step: In the first step, the corresponding first step of A was prepared 1-(2-acetamido-4-nitrophenoxy) 2,3-epoxypropane. 2nd step: Preparation of 1 - (2-acetamido-4.-nitroenoxy)-3-piperidino-propanol-2. 8 g (0.03 mol) of 1-(2-acetaraido-4-nitrophenoxy)-2,3-epoxypropane was reacted with 38.3 g (0.45 mol) of piperidine corresponding to the instructions in second step A. The resulting yellow oil was further processed in the third stage.
3- ;- trinn : Fremstilling av 1 - (2-ami.no-4-nitrof enoksy)-3-pip-eridino-propanol-2-hydroklorid- 3- ;- step: Preparation of 1 - (2-ami.no-4-nitrophenoxy)-3-pipe-eridino-propanol-2-hydrochloride-
Avspalting av acetylresten ble gjennomført analogt trinn 3 i punkt A. Forbindelsen 1 -(2-amino-4-nitro-fenoksy)-3-piperidino-propanol-2-hydroklorid ble dannet i form av gule krystaller, som smelter ved 180°C under spalting. 4. trinn: Fremstilling av 1-(2,4-diaminofenoksy)-3-piperi-dino-propanol-2-trihydroklorid. Cleavage of the acetyl residue was carried out analogously to step 3 in point A. The compound 1 -(2-amino-4-nitro-phenoxy)-3-piperidino-propanol-2-hydrochloride was formed in the form of yellow crystals, which melt at 180°C during cleavage. 4th step: Preparation of 1-(2,4-diaminophenoxy)-3-piperidino-propanol-2-trihydrochloride.
Hydrogineringen foregikk analogt angivelser i trinn 4 i A, og av den ønskede forbindelse får man hvite krystaller med smeltepunkt 104 - 108°C. The hydrogenation proceeded analogously to the instructions in step 4 in A, and the desired compound gives white crystals with a melting point of 104 - 108°C.
C. 1 -(2,4-diaminofenoksy)-3-morfolino-propanol-2 - trihydroklorid. 1. trinn: Det ble igjen fremstillet 1 -(2-acetamido-4-nitro-fenoksy)-2,3-epoksypropan tilsvarende punkt A, for videre forarbeidelse. 2. trinn: Fremstilling av 1 -(2-acetamido-4-nitrofenoksy)-3-morfolino-propanol-2. C. 1-(2,4-Diaminophenoxy)-3-morpholino-propanol-2-trihydrochloride. 1st step: 1-(2-acetamido-4-nitro-phenoxy)-2,3-epoxypropane corresponding to point A was again produced for further processing. 2nd step: Preparation of 1-(2-acetamido-4-nitrophenoxy)-3-morpholino-propanol-2.
Fremstillingen foregikk analogt trinn 2, p.unkt A, av 8 g (0,03 mol) 1 -(2-acetamido-4-nitrofenoksy) 2,3 epoksypropan og 40 g (0,45 mol) morfolin, og førte det i forbindelsen iform av hvite krystaller med smeltepunkt 77 - 80°C. 3. trinn: Fremstilling av 1-(2-amino-4-nitrofenoksy)-3-morfolino-propanol-2-hydroklorid. The preparation proceeded analogously to step 2, point A, from 8 g (0.03 mol) 1 -(2-acetamido-4-nitrophenoxy) 2,3 epoxypropane and 40 g (0.45 mol) morpholine, and brought it into the compound in the form of white crystals with a melting point of 77 - 80°C. 3rd step: Preparation of 1-(2-amino-4-nitrophenoxy)-3-morpholino-propanol-2-hydrochloride.
Ved avspaltning av acetylresten tilsvarende angivelsen i punkt A, ble det ønskede produkt dannet i form av gule krystaller. 4. trinn: Fremstilling av- 1-(2-diaminofenoksy)-3-morfolino-propanol-2-trihydrokiorid. By cleavage of the acetyl residue corresponding to the indication in point A, the desired product was formed in the form of yellow crystals. 4th step: Preparation of 1-(2-diaminophenoxy)-3-morpholino-propanol-2-trihydrochloride.
Det i 3« trinn dannede produkt, ble hydroginert tilsvarende angivelsene ved punkt A, og av den ønskede forbindelse i form av hvite krystaller og smeltepunkt på 80°C. D.. 1 - (2 , 4-diaminof enoksy)-3-anilino-propanol-2-trihydroklorid . 1. trinn: Fremstilling av 1(2- acetamido-4-nitro-fenoksy)-2,3-epoksypropan ifølge punkt A. 2 . trinn : Fremstilling av 1- (2-a.cetamido-4-nitrof enoksy )-3-anilino-propanol-2 ifølge punkt A, av 8 g (0,03 mol) 1-(2-acetamido-4-nitrofenoksy)-2,3-epoksypropan og 40 g (0,45mol) anilin. Produktet ble dannet i form av hvite krystaller og smeltepunkt 249 - 152°C. 3. trinn: Fremstilling av 1-(2-amino-4-nitrofenoksy)-3-ani-1ino-propanol-2-hydrokiorid. The product formed in step 3 was hydrogenated corresponding to the indications at point A, and of the desired compound in the form of white crystals and a melting point of 80°C. D.. 1-(2,4-diaminophenoxy)-3-anilino-propanol-2-trihydrochloride. 1st step: Preparation of 1(2-acetamido-4-nitro-phenoxy)-2,3-epoxypropane according to point A. 2. step: Preparation of 1-(2-a.cetamido-4-nitrophenoxy)-3-anilino-propanol-2 according to point A, from 8 g (0.03 mol) 1-(2-acetamido-4-nitrophenoxy) -2,3-epoxypropane and 40 g (0.45 mol) aniline. The product was formed in the form of white crystals and melting point 249 - 152°C. 3rd step: Preparation of 1-(2-amino-4-nitrophenoxy)-3-ani-1ino-propanol-2-hydrochloride.
Produktet ble dannet tilsvarende angivelser iThe product was formed corresponding to the indications in
3-trinn av punkt A, i form av gule krystaller av smeltepunkt 115 - 120°C. 4. trinn: Fremstilling av 1- (2,4-diaminofenoksy)-3-ani-1ino-propanol-2-trihydroklorid. 3-stage of point A, in the form of yellow crystals of melting point 115 - 120°C. 4th step: Preparation of 1-(2,4-diaminophenoxy)-3-ani-1ino-propanol-2-trihydrochloride.
Ved hydrogineringen av det i 3- trinn dannede produkt analogt angivelsene ved punkt A, ble denønskede forbindelse dannet som hvite krystaller som smeltet ved 116°C under spalting. During the hydrogenation of the product formed in 3 steps analogously to the indications at point A, the desired compound was formed as white crystals which melted at 116°C during cleavage.
E. 1 -(2,4-diaminofenoksy)-3-(N-etylanilino)-propa-noi-2-trihydroklorid. E. 1-(2,4-Diaminophenoxy)-3-(N-ethylanilino)-propanoyl-2-trihydrochloride.
1, trinn: Fremstilling av 1 -(2-acetamido-4-nitrofenoksy) 1, step: Preparation of 1-(2-acetamido-4-nitrophenoxy)
2,3-epoksypropan ifølge A.2,3-epoxypropane according to A.
2. trinn: Fremstilling av 1 - (2-acetamido-4-nitrofenoksy)-3-(N-etylanilino)-propanol-2 foregikk ifølge angivelsen under A. av 8 g (0,03 mol) 1-(2-ace-tamido-4-nitrofenoksy)-2,3-epoksypropan og 54»5 g N-etylaniliri i 5 timer ved 60°C, og ga forbindelsen iform av orange krystaller og smeltepunkt på 80 - 84°C. 2nd step: Preparation of 1 - (2-acetamido-4-nitrophenoxy)-3-(N-ethylanilino)-propanol-2 took place according to the information under A. from 8 g (0.03 mol) 1-(2-ace -tamido-4-nitrophenoxy)-2,3-epoxypropane and 54.5 g of N-ethylaniliri for 5 hours at 60°C, and gave the compound in the form of orange crystals and a melting point of 80 - 84°C.
3- trinn: Avspalting av acetylresten tilsvarende angivelser i 3. trinn, punkt A, gav 1 -(2-amino-4-nitrofenoksy) --3-(N-etylanilino)-propanol-2-hydrokiorid som hygroskopisk gule krystaller av smeltepunkt 125 - 130°C. ■ 3rd step: Cleavage of the acetyl residue corresponding to indications in 3rd step, point A, gave 1-(2-amino-4-nitrophenoxy)-3-(N-ethylanilino)-propanol-2-hydrochloride as hygroscopic yellow crystals of melting point 125 - 130°C. ■
4, trinn: Fremstilling av 1-(2,4 diaminofenoksy)-3-(N-etylanilino)-propanol-2-trihydroklorid. 4, step: Preparation of 1-(2,4 diaminophenoxy)-3-(N-ethylanilino)-propanol-2-trihydrochloride.
Ved hydroginering av det i 3. trinn dannede produkt, ble denønskede forbidelsen dannet i On hydrogenation of the product formed in the 3rd step, the desired compound was formed in
form av hygroskopiske hvite ' krystaller av smeltepunkt 80 - 85°C. form of hygroscopic white crystals of melting point 80 - 85°C.
F. - 1-(2,4 diaminofenoksy)-3-bezylamino-propanol-2-trihydroklorid. F. - 1-(2,4 diaminophenoxy)-3-benzylamino-propanol-2-trihydrochloride.
1. trinn: Fremstilling av 1 -(2-acetamido-4-nitrofenoksy) 1st step: Preparation of 1-(2-acetamido-4-nitrophenoxy)
-2,3-epoksypropan i følge A.-2,3-epoxypropane according to A.
2. trinn: Tilsvarende angivelse punkt A, ble 1-(2-acetamido-4.-ni trof enoksy) -3-benz yl amino-propanol -2 dannet av 8 g (0.03mol) 1-(2-acetamido-4-nitrofenoksy)-2,3-eposkypropan ved omsetning med 48 g (0,45 mol) bezylamin i form av gulorange krystaller av smeltpunkt av 73 - 77°C. 3. trinn: Avspaltingen av acetylres.ten førte til 1- (2-amino-4.-nitrofenoksy)-3-benzylamino-propanol-2-hydro-klorid i form av lysegule krystaller av smeltepunkt 108 - 112°C. 4.. trinn: Ved hydroginering av de i 3-trinn dannede produkt, ble det dannet den ønskede forbindelse 1-(2,4-diaminofenoksy)-3-bezyl-aminopropanol-2-trihydroklorid i form av hygroksopiske lyse fiol-ette krystaller. 2nd step: Corresponding to point A, 1-(2-acetamido-4.-nitrophenoxy)-3-benzyl amino-propanol-2 was formed from 8 g (0.03 mol) 1-(2-acetamido-4 -nitrophenoxy)-2,3-epoxypropane by reaction with 48 g (0.45 mol) of bezylamine in the form of yellow-orange crystals with a melting point of 73 - 77°C. 3rd step: The cleavage of the acetyl residue led to 1-(2-amino-4.-nitrophenoxy)-3-benzylamino-propanol-2-hydrochloride in the form of pale yellow crystals of melting point 108 - 112°C. 4th step: By hydrogenation of the product formed in step 3, the desired compound 1-(2,4-diaminophenoxy)-3-benzyl-aminopropanol-2-trihydrochloride was formed in the form of hygroscopic light violet crystals .
G. 1-(2,4 diaminofenoksy)-3-etoksy-propanol-2-dihydroklorid. 1. trinn: Fremstilling av 1 - (2-acetamido-4-nitrofenoksy)-2,3-epoksypropan.ifølge A. 2. trinn: Analogt fremstillingen ved A ble 1-(2-acetamido-4-nitrofenoksy)-3-etoksypropan-2 blandet med om-setningen av 8 g (0,05 mol) 1 - (2-a.cetamido-4-nitro-fenoksy)-2,3-epoksypropan med 50 ml etanol i nærvær av 0,2 ml konsentrert svovelsyre under 8 timers koking under tilbakeløp. Forbindelsen ble etter inndampning dannet som gul olje. 3. trinn: Tilsvarende fremstillingsangivelsene ved A ble det dannet 1 - (2-amino-4-nitrofenoksy)-3-etoksy-propanol-2-hydroklorid i form av olivengrønne krystaller ved smeltepunkt 75°C. 4. trinn: Hydrogineringen tilsvarende A ga det ønskede 1-(2,4-diaminofenoksy)-3-etoksy-propanol-2-dihydroklorid som beige krystaller, smeltet under spalting ved 93°C. G. 1-(2,4-diaminophenoxy)-3-ethoxy-propanol-2-dihydrochloride. 1st step: Preparation of 1 - (2-acetamido-4-nitrophenoxy)-2,3-epoxypropane according to A. 2nd step: Analogous to the preparation at A, 1-(2-acetamido-4-nitrophenoxy)-3- ethoxypropane-2 mixed with the reaction of 8 g (0.05 mol) 1-(2-a.cetamido-4-nitro-phenoxy)-2,3-epoxypropane with 50 ml of ethanol in the presence of 0.2 ml of concentrated sulfuric acid during 8 hours of boiling under reflux. After evaporation, the compound was formed as a yellow oil. 3rd step: Corresponding to the preparation instructions at A, 1 - (2-amino-4-nitrophenoxy)-3-ethoxy-propanol-2-hydrochloride was formed in the form of olive green crystals at a melting point of 75°C. 4th step: The hydrogenation corresponding to A gave the desired 1-(2,4-diaminophenoxy)-3-ethoxy-propanol-2-dihydrochloride as beige crystals, melting under cleavage at 93°C.
H. 1 - (2, 4d.iaminof enoksy)-propandiol-2, 3-dihydroklorid. 1 . trinn: Fremstillingen av T-(2-acetamido-4 -nitro-f enoksy ) -2 , 3-epoksypropan ifølge .A, 2. trinn: Fremstillingen av.1- (2-acetamido-4-nitrofenoksyl) -2,3-propandiol foregikk ifølge A, ved koking av 5 g- (0,019 mol) 1-(2-acetamido-4-nitrofenoksy)-2,3-epoksypropan med $0 ml vann i nærvær av 0,05'g konsentrert svovelsyre under tilbakeløp i 8 timer. Det dannede seige produkt ble frasuget, og anvendt H. 1-(2,4diaminophenoxy)-propanediol-2,3-dihydrochloride. 1. step: The preparation of T-(2-acetamido-4-nitro-phenoxy)-2,3-epoxypropane according to .A, 2nd step: The preparation of .1-(2-acetamido-4-nitrophenoxy)-2,3 -propanediol was carried out according to A, by boiling 5 g-(0.019 mol) 1-(2-acetamido-4-nitrophenoxy)-2,3-epoxypropane with $0 ml of water in the presence of 0.05 g of concentrated sulfuric acid under reflux in 8 hours. The tough product formed was sucked off and used
i 3. trinn.in the 3rd step.
3. trinn: Avspaltingen av acetylresten i følge angivelsen ved A ga 1 -(2-amino-4~nitro-fenoksy)-2,3-propan-diolhydroklorid i form av gule krystaller og smeltepunkt 152 - 157°C. 3rd step: The cleavage of the acetyl residue according to the indication at A gave 1 -(2-amino-4~nitro-phenoxy)-2,3-propane-diol hydrochloride in the form of yellow crystals and melting point 152 - 157°C.
4- trinn: Ved hydroginering av produktet fra 3- trinn bleStep 4: When hydrogenating the product from step 3,
det dannet 1 -(2,4-diaminofenoksy)-2,3-propandiol-dihydroklorid;'. i form' av hvite krystaller av smeltepunkt 95°C.'it formed 1-(2,4-diaminophenoxy)-2,3-propanediol dihydrochloride;'. in the form of white crystals of melting point 95°C.
De overnevnte, deres fremstilling omtalte 1-substituerte 2-hydroksypropyl-(2,4-diaminofenoleter ) A til H The aforementioned, their preparation mentioned 1-substituted 2-hydroxypropyl-(2,4-diaminophenol ether) A to H
ble anvendt som koblerkomponenter i følgende eksempler.were used as coupler components in the following examples.
Som fremkallerkomponenter tjente følgende stoffer:The following substances served as developer components:
E 1: p-toluylendiaminE 1: p-toluylenediamine
E 2: 2,4.5»6-tetraaminopyrimidinE 2: 2,4,5»6-tetraaminopyrimidine
E 3- 2,5 diaminoanisolE 3- 2,5 diaminoanisole
E 4: N,N-bis-( £> -hydroksyety1)-p-fenylendiaminE 4: N,N-bis-(£>-hydroxyethyl)-p-phenylenediamine
E 5: 2-metylamino-4> 5» 6-triarninopyrimidinE 5: 2-methylamino-4>5»6-triarninopyrimidine
E 6: 2-klor-p-fenylendiaminE 6: 2-chloro-p-phenylenediamine
E 7: 1-fenyl-3-karbamoyl-4-amino-pyrazolon-5E 7: 1-phenyl-3-carbamoyl-4-amino-pyrazolone-5
E 8: p-aminofenolE 8: p-aminophenol
E 9: N,N-dimetyl-p-fenylendiaminE 9: N,N-dimethyl-p-phenylenediamine
E10: N-etyl -N j3-hydr oksy etyl -p-f enylendiamin . E10: N-ethyl -N j3-hydroxy ethyl -p-phenylenediamine.
Hårfarvemidlene ifølge oppfinnelsen, ble anvendtThe hair dyes according to the invention were used
i form av krememulsjoner. Derved ble i en emulsjon av 10. Vektdeler fettalkoholer av kjedelengde C-]2~C18'10.vektdeler fettalkoholsulfat (natriumsalt) av in the form of cream emulsions. Thereby, in an emulsion of 10 parts by weight of fatty alcohols of chain length C-]2~C18, 10 parts by weight of fatty alcohol sulphate (sodium salt) of
kj edelelengde C^-C^g og,kj noble length C^-C^g and,
75 vektdeler vann75 parts by weight water
hver gang innarbeidet 0,01 mol av de -i følgende tabell opp-førte fremkallerstoffer og koblerstoffer. Deretter ble emulsjonens pH-verdi innstillet med ammoniakk på .9.5, og emulsjonen oppfylt med vann til 100 vektdeler. Den oksydative kobling ble gjennomført med 1%-ig hydrogenperoksydopp--løsning.som oksydasjonsmiddel, idet det til 100 vektdeler av emulsjonen ble satt 10 vektdeler hydrogenperoksydopp-løsning. Farvekremene med tilsetning : av oksydasjonsmiddel ble påført på. 90% grånet ikke spesielt forbehandlet menneskehår, og etterlatt der i 30 minutter. Etter avslutning av farveprosessen ble håret utvasket med et vanlig hårvaskemiddel og deretter tørket. De derved dannede farvinger fremgår av følgende tabell 1. each time incorporated 0.01 mol of the developer substances and coupling substances listed in the following table. The emulsion's pH value was then adjusted with ammonia to .9.5, and the emulsion filled with water to 100 parts by weight. The oxidative coupling was carried out with a 1% hydrogen peroxide solution as oxidizing agent, with 10 parts by weight of the emulsion being added to 10 parts by weight of hydrogen peroxide solution. The color creams with the addition of oxidizing agent were applied to. 90% gray not specially pre-treated human hair, and left there for 30 minutes. After finishing the coloring process, the hair was washed out with a normal hair detergent and then dried. The resulting colors are shown in the following table 1.
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792948093 DE2948093A1 (en) | 1979-11-29 | 1979-11-29 | NEW COUPLER COMPONENTS FOR OXIDATION HAIR COLORS, THEIR PRODUCTION AND USE AND THEIR HAIR COLORING CONTAINERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO803288L true NO803288L (en) | 1981-06-01 |
Family
ID=6087191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO803288A NO803288L (en) | 1979-11-29 | 1980-11-03 | NEW CONNECTOR COMPONENTS FOR OXYDATION HAIR COLORS, THEIR MANUFACTURING AND USE, AND HAIR COLORING AGENTS CONTAINING THESE |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0029964A1 (en) |
| JP (1) | JPS5690043A (en) |
| DE (1) | DE2948093A1 (en) |
| DK (1) | DK465680A (en) |
| FI (1) | FI803435L (en) |
| NO (1) | NO803288L (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3016881A1 (en) * | 1980-05-02 | 1981-11-19 | Henkel KGaA, 4000 Düsseldorf | NEW COUPLER COMPONENTS FOR OXIDATION HAIR COLORS, THEIR PRODUCTION AND THEIR HAIR COLORING CONTAINERS |
| AT393219B (en) * | 1980-07-01 | 1991-09-10 | Oreal | Colorant for keratin fibres, in particular for hair, and method for colouring keratin fibres, in particular hair |
| CH661501A5 (en) * | 1982-01-26 | 1987-07-31 | Oreal | COMPOUNDS DERIVATIVE FROM AMINO-3 PROPANOL-2 FOR USE IN DYEING HAIR, PREPARATION METHOD THEREOF, DYE COMPOSITION CONTAINING THE SAME, AND HAIR DYEING METHOD THEREOF. |
| 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 |
| DE4003907A1 (en) * | 1990-02-09 | 1991-08-14 | Schwarzkopf Gmbh Hans | 5-Tri:fluoromethyl-1,3-di:aminobenzene(s) as hair colourant - have good stability to heat and light, and are compatible with other colourants for shade modification |
| FR2684296B1 (en) * | 1991-12-03 | 1995-04-21 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS WITH AN ACID PH ALCOXYMETAPHENYLENEDIAMINE AND COMPOSITIONS IMPLEMENTED. |
| EP1353637A4 (en) * | 2001-01-23 | 2008-12-03 | P & G Clairol Inc | Novel couplers for use in oxidative hair dyeing |
| WO2002058659A1 (en) * | 2001-01-23 | 2002-08-01 | P&G-Clairol, Inc. | Couplers for oxidative coloration of hair |
| EP1353638A4 (en) * | 2001-01-23 | 2008-12-03 | P & G Clairol Inc | Novel couplers for use in oxidative hair dyeing |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2362116A1 (en) * | 1976-08-20 | 1978-03-17 | Oreal | METAPHENYLENEDIAMINES AND TINCTORIAL COMPOSITIONS CONTAINING THEM |
| DE2758735A1 (en) * | 1977-10-06 | 1979-04-19 | Bristol Myers Co | OXIDIZING COMPOSITION FOR DYE KERATINOESE FIBERS, ESPECIALLY HUMAN HAIR |
-
1979
- 1979-11-29 DE DE19792948093 patent/DE2948093A1/en not_active Withdrawn
-
1980
- 1980-11-03 FI FI803435A patent/FI803435L/en not_active Application Discontinuation
- 1980-11-03 DK DK465680A patent/DK465680A/en not_active Application Discontinuation
- 1980-11-03 NO NO803288A patent/NO803288L/en unknown
- 1980-11-20 EP EP80107210A patent/EP0029964A1/en not_active Withdrawn
- 1980-11-28 JP JP16682480A patent/JPS5690043A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2948093A1 (en) | 1981-06-11 |
| EP0029964A1 (en) | 1981-06-10 |
| DK465680A (en) | 1981-05-30 |
| FI803435L (en) | 1981-05-30 |
| JPS5690043A (en) | 1981-07-21 |
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