US3836326A - Dyeing hair with nitro-substituted phenylene compounds - Google Patents
Dyeing hair with nitro-substituted phenylene compounds Download PDFInfo
- Publication number
- US3836326A US3836326A US00090825A US9082570A US3836326A US 3836326 A US3836326 A US 3836326A US 00090825 A US00090825 A US 00090825A US 9082570 A US9082570 A US 9082570A US 3836326 A US3836326 A US 3836326A
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- United States
- Prior art keywords
- hair
- formula
- composition
- compound
- nitro
- Prior art date
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- Expired - Lifetime
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- 238000004043 dyeing Methods 0.000 title claims abstract description 9
- 210000004209 hair Anatomy 0.000 title claims description 30
- -1 nitro-substituted phenylene compounds Chemical class 0.000 title abstract description 12
- 239000000203 mixture Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000000118 hair dye Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 230000003113 alkalizing effect Effects 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000008365 aqueous carrier Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000007970 homogeneous dispersion Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 210000004761 scalp Anatomy 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- DPLJNTWBXCKJOL-UHFFFAOYSA-N 3-bromo-4,5-diethoxybenzonitrile Chemical compound CCOC1=CC(C#N)=CC(Br)=C1OCC DPLJNTWBXCKJOL-UHFFFAOYSA-N 0.000 description 2
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 2
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000003128 head Anatomy 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- IENQDRALNOEFHD-UHFFFAOYSA-N methyl 3-(2,4-dinitroanilino)propanoate Chemical compound COC(=O)CCNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O IENQDRALNOEFHD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- ZZNDQCACFUJAKJ-UHFFFAOYSA-N 1-phenyltridecan-1-one Chemical compound CCCCCCCCCCCCC(=O)C1=CC=CC=C1 ZZNDQCACFUJAKJ-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QJDSLDWVMCWWCO-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)hexanoic acid Chemical compound C1=CC=C2C(=O)N(CCCCCC(=O)O)C(=O)C2=C1 QJDSLDWVMCWWCO-UHFFFAOYSA-N 0.000 description 1
- KOQCISGPATVUJH-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)hexanoyl chloride Chemical compound C1=CC=C2C(=O)N(CCCCCC(=O)Cl)C(=O)C2=C1 KOQCISGPATVUJH-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229950010286 diolamine Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 210000004919 hair shaft Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229950005425 sodium myristyl sulfate Drugs 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- A61K8/418—Amines containing nitro groups
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- R and R is each independently selected from the group consisting of a hydrogen atom and lower alkyl, R and R is each independently C C hydroxyalkyl, and n is an integer from one to six.
- lower alkyl comprehends both straight-chain and branched-chain alkyl groups containing from one to six carbon atoms, e.g. methyl, ethyl, isopropyl, n-butyl, n-hexyl and the like.
- R and R each represent a methyl group.
- C -C hydroxyalkyl comprehends hydroxyalkyl groups containing from two to three carbon atoms, e.g., hydroxyethyl, hydroxypropyl and and hydroxyisopropyl.
- R and R each represents a hydroxyethyl group.
- n represents an integer from one to six.
- n is two to five; most satisfactory products are those in which n represents 2.
- Exemplary compounds of Formula I include, for example, N -[2-(N,N-dimethylcarboxamido)ethyl1-2- nitro-N,N"bis-(2-hydroxyethyl)-p-phenylenediamine; N-[2-(N-methylcarboxamido)ethyl]-2-nitro- N,N"-bis-(2-hydroxyethyl)-p-phenylenediamine; N- (Z-carboxamidoethyl )-2-nitro-N,N-bis-( Z-hydroxyethyl)-p-phenylenediamine; N-(5-carboxamidopentyl)- 2 2-nitro-N,N -bis-(2-hydroxyethyl)-pphenylenediamine.
- nitro-substituted phenylene compounds of Formula I are most useful as dyes for dyeing human hair, they can also be most useful as dyes for dyeing keratinaceous material such as furs, natural protein fibers (e.g., wool, silk, etc.) and synthetic polyamide fibers such as nylon.
- the compounds of Formula I exhibit strong affinity to hair and other keratinaceous fibers, bond well to such fibers, and are compatible with other known hair dyes so that when used in combination they produce compositions of varying shades.
- Still other advantages of the present invention are the provisions of hair dye compositions which can color human hair in a relatively short time at room temperatures and without injury or damage to the hair shaft, skin or scalp.
- the compounds encompassed by Formula I can be produced by reacting a compound of the formula 0 R NH(CHa),,- i J-N Formula II wherein R,R and n are as above defined, with a compound selected from the group consisting of ethylene oxide and propylene oxide.
- the reaction of a compound of Formula II with ethylene oxide or propylene oxide is conveniently carried out in a reaction medium inert to the reactants such as an inert solvent.
- the inert solvent can be a lower alkanol (e.g., methanol, ethanol, etc.) or the like.
- the reaction is suitably carried out at the reflux temperature of the mixture.
- the materials of Formula II, employed in the above reaction can be prepared by any one of several methods.
- the compounds can be: produced by reacting l-chloro-2,4-dinitrobenzene with a compound of Formula VI nxrim cn,),,co cn Formula Vl wherein X is a halogen atom, and n is as above defined, to produce a compound of Formula IV N 0 3 Formula IV wherein n is as above defined, reacting this product with an amine of Formula V Formula V wherein R and R are as above defined, to produce a compound of Formula III mula ⁇ ? wherein R and R and n are as above defined, and
- the starting materials of Formula VI are known and have already been described in the literature.
- the material can be I-ICI.NH (CH;) CO CH
- the reaction of 1-chloro-2,4-dinitrobenzene with the salt of Formula VI is conveniently carried out in the presence of an acid binding agent.
- Suitable acid binding agents include alkali metal carbonates, alkali metal bicarbonates, tertiary amines and the like.
- the acid binding agent can be sodium carbonate, sodium bicarbonate or triethyl amine; preferably sodium bicarbonate is utilized.
- This reaction can be carried out in an inert organic solvent such as alcohol which is inert to the reactants at the reflux temperature of the mixture.
- the reaction of a compound of Formula IV with an amine of Formula V is also suitably conducted in an inert solvent such as alcohol at the reflux temperature of the reaction mixture.
- some of the materials of Formula II can be prepared by reacting l-chloro-2,4-dinitrobenzene with a compound of Formula VIa 2( 2)7l E Formula VIa wherein n is as above defined, to produce a compound of Formula [Va HIIUCHDUCEN N Formula IVa wherein n is as above defined, hydrolyzing the product to produce a compound of Formula Illa Formula IIIa wherein n is as above defined, and hydrogenating the product obtained therefrom.
- Hydrolysis of the compound of Formula [Va is conveniently carried out using an aqueous acid such as, for example, aqueous hydrochloric acid.
- aqueous acid such as, for example, aqueous hydrochloric acid.
- the procedure whereby a compound of Formula [11a is hydrogenated is carried out in a similar manner to that for the hydro genation of Formula III.
- a tinctorially effective amount of a compound of Formula I can be incorporated into any of several carriers to produce hair dye compositions such as hair dyes, toners, lotions, shampoos and the like.
- hair dye compositions can be in liquid form comprising neutral or alkaline aqueous solutions of the compound of Formula I.
- dye compositions can include conventional ingredients found in hair dye compositions such as organic solvents for the dye, thickeners, detergents, gums and the like.
- the term carrier comprises a material, preferably a liquid, into which the compo d of Formula I is mixed and which dissolves or dispe s the compound without impairing the effectiveness f the dye and which does not injure or damage the keratinaceous material on which it is used, e.g., hair.
- Water or organic solvents such as alcohol can be used as a carrier, and mixtures of water with water miscible organic solvents can also be utilized, the organic solvent serving to facilitate solution of the dye. If desired, the dye can be first dissolved in the solvent and then diluted with water.
- Suitable organic solvents include, for example, lower alkyl monohydric alcohols (e.g., ethanol, isopropanol, etc.), lower aliphatic dihydric alcohols (e.g., ethylene glycol, propylene glycol), and certain polyhydric alcohols, ketones, esters and the like.
- the dispersion of the various ingredients can be accelerated by the addition of a detergent or dispersing agent such as sodium lauryl sulfate or sodium myristyl sulfate, triethanolamine lauryl sulfate, etc.
- the water miscible organic solvents utilized to facilitate solution of the dye can vary from about 1 percent to about 30 percent by weight of the composition; preferably from about 2 to about 10 percent.
- the detergent or dispersing agent can likewise vary from about 1 to about 30 percent by weight of the composition; preferably about 15 percent.
- an alkalizing agent can be added to the hair dye composition to enhance its effectiveness.
- Suitable alkalizing agents are those which are non-toxic and which do not precipitate the dye or injure the scalp.
- Sufficient alkalizing agent can be used to produce a composition having a pH of from about 7 to about 12; preferably from 7.5 to 1 1.
- Suitable alkalizing agents include ammonia derivative alkalizing agents, alkali metal hydroxides, alkaline earth hydroxides and the like.
- the alkalizing agent can be ammonium hydroxide, a lower alkanolamine (e.g., mono-, di or tri-ethanolamine), lower alkyl amines (e.g., mono or diethyl amine), lower alkylene-diamines (e.g., propylene diamine) or a heterocyclic amine (e.g., morpholine).
- a lower alkanolamine e.g., mono-, di or tri-ethanolamine
- lower alkyl amines e.g., mono or diethyl amine
- lower alkylene-diamines e.g., propylene diamine
- a heterocyclic amine e.g., morpholine
- the alkalizing agent is an alkaline earth hydroxide
- such hydroxides include calcium hydroxide, magnesium hydroxide, and the like.
- the alkalizing agent is diethanolamine.
- the hair dye composition of the present invention can be applied to hair using any conventional method of application such as brushing, sponging, dipping, spraying, etc.
- the concentration of the active dye ingredient (i.e., compound of Formula I) required in the composition for tinctorial effectiveness varies with the particular kind of hair dye composition and the color desired. Desirably it may range from 0.01 to 1 percent, preferably from 0.05 to percent; in the case of aqueous dye compositions to be applied to human hair on the head, the range is still more preferably from 0.5 to 2 percent.
- the temperature of the hair dye composition can vary over temperatures conventional to the art.
- the temperature of the hair dye composition when applied to the human hair on the head can be from room temperature (i.e. about C) to about 45C.
- EXAMPLE 1 A solution of 50 g. (0.56 mole) of B-alanine in 300 m1 of methanol was heated to reflux. Hydrogen chloride gas was then introduced into the mixture for 4 hours. The solvent was then removed under vacuum and the resultant syrupy residue dissolved in 50 ml chloroform. Precipitation by addition of diethyl ether to the chloroform solution yielded: methyl-3- aminopropionate hydrochloride.
- N-(2-carbomethoxyethyl)- 2,4-dinitroaniline 11.3 g. (0.042 mole) of N-(2-carbomethoxyethyl)- 2,4-dinitroaniline was dissolved in 150 ml of methanol and 31.6 g. (0.7 mole) of dimethylamine was then added. The mixture was heated to reflux for 10 hours, cooled and filtered yielding: N-[ 2- (N',N'dimethylcarboxamido)ethyl]-2.4-dinitroaniline. m.p. -143C.
- EXAMPLE 2 A flask containing a mixture of 13.1 g. of 6-amino-nhexanoic acid (0.1 mole) and 14.8 g. (0.1 mole) of phthalic anhydride was heated in an oil bath at C until frothing of the mixture stopped (about 20 minutes). The solid resulting upon cooling was recrystallized from an ethanol/water mixture yielding: 6- phthalimido-n-hexanoic acid. m.p. 8182C.
- the ingredients were mixed together in the order listed above to provide a homogeneous dispersion, and the composition was applied to unbleached natural blonde and unbleached 50 percent gray hair for 30 minutes at a bath to hair ratio of 2.511 by weight at room temperature, producing in each case a light violet tone which did not wash out.
- EXAMPLE 8 A silver blue toning dye having a light intensity and suitable for gray hair was prepared having the following composition:
- composition was prepared and tested as described in Example 7, producing the same results. When applied to the hair for 60 minutes instead of 30, a medium violet tone was produced in each case.
- a silve blue toning dye having a light intensity and suitable for gray hair is prepared having the following composition:
- composition was prepared and tested as described in Example 7, producing a medium violet tone which did not wash out.
- a hair grooming lotion suitable for gray hair was prepared having the following composition:
- the ingredients were mixed together in the order named to form a homogeneous dispersion, and the composition was applied to unbleached natural blonde and unbleached 50 percent gray hair atroom temperature. permitted to remain for minutes and rinsed out, producing a light silver shade in each case.
- a hair dye composition comprising an aqueous carrier and as an active ingredient thereof a tinctorially effective amount of a compound of the formula 5.
- a method of dyeing hair which method comprises applying to the hair an effective amount of a hair dye composition comprising an aqueous carrier and as an active ingredient thereof a tinctorially effective amount of a compound of the formula wherein R and R is each independently lower alkyl,
- R and R is each independently C -C hydroxyalkyl, and n is an integer from one to six. 7. The method of claim 6 wherein the composition further includes an alkalizing agent.
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Abstract
WHEREIN R1 and R2 is each independently a hydrogen atom or lower alkyl, R3 and R4 is each independently C2-C3 hydroxyalkyl, and n is an integer from one to six, are used as dyes for dyeing keratinaceous material.
Nitro-substituted phenylene compounds of the formula
Nitro-substituted phenylene compounds of the formula
Description
Sohol et a1,
tes
[ Sept. 17, 1974 1 DYIEIING HAIR WIITH NIITRO-SUBSTTTUTED PHENYLENE COMPOUNDS [75] Inventors: Phillip Edward Sokol, Chicago;
Hui-Clio Tsai, Evanston, both of I11.
[73] Assignee: The Gillette Company, Boston,
Mass.
[22] Filed: Nov. 18, 11970 {21] Appl. No.: 90,825
[52] US. Cl 8/110.1, 8/10, 8/178, 260/326, 260/465 E, 260/471 C, 260/558 A, 260/559 A, 421/70 Primary Examiner-Albert T. Meyers Assistant ExaminerVera C. Clarke [5 7] ABSTRACT Nitro-substituted phenylene compounds of the formule wherein R and R is each independently a hydrogen atom or lower alkyl, R and R is each independently C -C hydroxyalkyl, and n is an integer from one to six, are used as dyes for dyeing keratinaceous material.
9 Claims, N0 Drawings DYEING HAIR WITH-I NITRO-SUBSTITUTED PlllllENYLlENE COMPOUNDS BACKGROUND OF THE INVENTION 'and time which can be used are limited to those which can be tolerated by humans and the dye must produce the desired color in the hair with minimal coloring of the skin and scalp. In general, the temperature of the dye composition used on hair can be from room temperature (20 C) up to 45 C and the time for achieving the desired color can be from as little as or minutes to a maximum of about 45 minutes, preferably no more than 30 minutes. The dyeing of textile fibers and fabrics, on the other hand, is frequently carried out at temperatures as high as 100 C for a period of many minutes.
The unique compounds of the present invention are represented by the formula Formula I wherein R and R is each independently selected from the group consisting of a hydrogen atom and lower alkyl, R and R is each independently C C hydroxyalkyl, and n is an integer from one to six.
As used herein, lower alkyl comprehends both straight-chain and branched-chain alkyl groups containing from one to six carbon atoms, e.g. methyl, ethyl, isopropyl, n-butyl, n-hexyl and the like. In a preferred embodiment, R and R each represent a methyl group. Likewise, it will be understood that the term C -C hydroxyalkyl comprehends hydroxyalkyl groups containing from two to three carbon atoms, e.g., hydroxyethyl, hydroxypropyl and and hydroxyisopropyl. In a preferred embodiment, R and R each represents a hydroxyethyl group.
As noted, n represents an integer from one to six. Suitably, n is two to five; most satisfactory products are those in which n represents 2.
Exemplary compounds of Formula I include, for example, N -[2-(N,N-dimethylcarboxamido)ethyl1-2- nitro-N,N"bis-(2-hydroxyethyl)-p-phenylenediamine; N-[2-(N-methylcarboxamido)ethyl]-2-nitro- N,N"-bis-(2-hydroxyethyl)-p-phenylenediamine; N- (Z-carboxamidoethyl )-2-nitro-N,N-bis-( Z-hydroxyethyl)-p-phenylenediamine; N-(5-carboxamidopentyl)- 2 2-nitro-N,N -bis-(2-hydroxyethyl)-pphenylenediamine.
While the nitro-substituted phenylene compounds of Formula I are most useful as dyes for dyeing human hair, they can also be most useful as dyes for dyeing keratinaceous material such as furs, natural protein fibers (e.g., wool, silk, etc.) and synthetic polyamide fibers such as nylon. The compounds of Formula I exhibit strong affinity to hair and other keratinaceous fibers, bond well to such fibers, and are compatible with other known hair dyes so that when used in combination they produce compositions of varying shades.
Still other advantages of the present invention are the provisions of hair dye compositions which can color human hair in a relatively short time at room temperatures and without injury or damage to the hair shaft, skin or scalp.
The compounds encompassed by Formula I can be produced by reacting a compound of the formula 0 R NH(CHa),,- i J-N Formula II wherein R,R and n are as above defined, with a compound selected from the group consisting of ethylene oxide and propylene oxide.
The reaction of a compound of Formula II with ethylene oxide or propylene oxide is conveniently carried out in a reaction medium inert to the reactants such as an inert solvent. The inert solvent can be a lower alkanol (e.g., methanol, ethanol, etc.) or the like. The reaction is suitably carried out at the reflux temperature of the mixture.
The materials of Formula II, employed in the above reaction, can be prepared by any one of several methods. Firstly, the compounds can be: produced by reacting l-chloro-2,4-dinitrobenzene with a compound of Formula VI nxrim cn,),,co cn Formula Vl wherein X is a halogen atom, and n is as above defined, to produce a compound of Formula IV N 0 3 Formula IV wherein n is as above defined, reacting this product with an amine of Formula V Formula V wherein R and R are as above defined, to produce a compound of Formula III mula}? wherein R and R and n are as above defined, and
hydrogenating the product obtained therefrom.
The starting materials of Formula VI are known and have already been described in the literature. For example, the material can be I-ICI.NH (CH;) CO CH The reaction of 1-chloro-2,4-dinitrobenzene with the salt of Formula VI is conveniently carried out in the presence of an acid binding agent. Suitable acid binding agents include alkali metal carbonates, alkali metal bicarbonates, tertiary amines and the like. For example, the acid binding agent can be sodium carbonate, sodium bicarbonate or triethyl amine; preferably sodium bicarbonate is utilized. This reaction can be carried out in an inert organic solvent such as alcohol which is inert to the reactants at the reflux temperature of the mixture. The reaction of a compound of Formula IV with an amine of Formula V is also suitably conducted in an inert solvent such as alcohol at the reflux temperature of the reaction mixture.
Hydrogenation of the product of Formula Ill can be effected using hydrogen in the presence of a noble metal catalyst (e.g., platinum/charcoal, palladium/- charcoal, etc.). The reaction suitably proceeds in the presence of a strong acid (e.g., hydrochloric, sulfuric, etc.) and a lower alkanol (e.g., methanol, ethanol, etc.). In a preferred embodiment, the hydrogenation is effected using platinum/charcoal in the presence of hydrochloric acid and ethanol.
Alternately, some of the materials of Formula II can be prepared by reacting l-chloro-2,4-dinitrobenzene with a compound of Formula VIa 2( 2)7l E Formula VIa wherein n is as above defined, to produce a compound of Formula [Va HIIUCHDUCEN N Formula IVa wherein n is as above defined, hydrolyzing the product to produce a compound of Formula Illa Formula IIIa wherein n is as above defined, and hydrogenating the product obtained therefrom.
The reaction of l-chloro-2,4-dinitrobenzene with a compound of Formula VIa is carried out under the same conditions as the reaction of Formula VI above described.
Hydrolysis of the compound of Formula [Va is conveniently carried out using an aqueous acid such as, for example, aqueous hydrochloric acid. The procedure whereby a compound of Formula [11a is hydrogenated is carried out in a similar manner to that for the hydro genation of Formula III.
For practical use of the compounds of Formula I as hair dyes, it is desirable to formulate them as hair dye compositions comprising as an active ingredient, a tinctorially effective amount of a compound of Formula I in a carrier. For example, a tinctorially effective amount of a compound of Formula I can be incorporated into any of several carriers to produce hair dye compositions such as hair dyes, toners, lotions, shampoos and the like. Such formulations can be in liquid form comprising neutral or alkaline aqueous solutions of the compound of Formula I. Additionally, dye compositions can include conventional ingredients found in hair dye compositions such as organic solvents for the dye, thickeners, detergents, gums and the like.
As used herein, the term carrier comprises a material, preferably a liquid, into which the compo d of Formula I is mixed and which dissolves or dispe s the compound without impairing the effectiveness f the dye and which does not injure or damage the keratinaceous material on which it is used, e.g., hair. Water or organic solvents such as alcohol can be used as a carrier, and mixtures of water with water miscible organic solvents can also be utilized, the organic solvent serving to facilitate solution of the dye. If desired, the dye can be first dissolved in the solvent and then diluted with water. Suitable organic solvents include, for example, lower alkyl monohydric alcohols (e.g., ethanol, isopropanol, etc.), lower aliphatic dihydric alcohols (e.g., ethylene glycol, propylene glycol), and certain polyhydric alcohols, ketones, esters and the like. The dispersion of the various ingredients can be accelerated by the addition of a detergent or dispersing agent such as sodium lauryl sulfate or sodium myristyl sulfate, triethanolamine lauryl sulfate, etc. The water miscible organic solvents utilized to facilitate solution of the dye can vary from about 1 percent to about 30 percent by weight of the composition; preferably from about 2 to about 10 percent. The detergent or dispersing agent can likewise vary from about 1 to about 30 percent by weight of the composition; preferably about 15 percent.
If desired, an alkalizing agent can be added to the hair dye composition to enhance its effectiveness. Suitable alkalizing agents are those which are non-toxic and which do not precipitate the dye or injure the scalp. Sufficient alkalizing agent can be used to produce a composition having a pH of from about 7 to about 12; preferably from 7.5 to 1 1. Suitable alkalizing agents include ammonia derivative alkalizing agents, alkali metal hydroxides, alkaline earth hydroxides and the like. For example, the alkalizing agent can be ammonium hydroxide, a lower alkanolamine (e.g., mono-, di or tri-ethanolamine), lower alkyl amines (e.g., mono or diethyl amine), lower alkylene-diamines (e.g., propylene diamine) or a heterocyclic amine (e.g., morpholine). Where the alkalizing agent is an alkaline earth hydroxide, such hydroxides include calcium hydroxide, magnesium hydroxide, and the like. In a preferred embodiment, the alkalizing agent is diethanolamine.
The hair dye composition of the present invention can be applied to hair using any conventional method of application such as brushing, sponging, dipping, spraying, etc.
The concentration of the active dye ingredient (i.e., compound of Formula I) required in the composition for tinctorial effectiveness varies with the particular kind of hair dye composition and the color desired. Desirably it may range from 0.01 to 1 percent, preferably from 0.05 to percent; in the case of aqueous dye compositions to be applied to human hair on the head, the range is still more preferably from 0.5 to 2 percent.
Although the time of contact of the hair dye composition with the hair is not critical, good results are achieved over a period of time from about 15 minutes to about 45 minutes; preferably about 30 minutes. The temperature of the hair dye composition can vary over temperatures conventional to the art. For example, the temperature of the hair dye composition when applied to the human hair on the head can be from room temperature (i.e. about C) to about 45C.
The following examples are given in further illustration of the invention.
EXAMPLE 1 A solution of 50 g. (0.56 mole) of B-alanine in 300 m1 of methanol was heated to reflux. Hydrogen chloride gas was then introduced into the mixture for 4 hours. The solvent was then removed under vacuum and the resultant syrupy residue dissolved in 50 ml chloroform. Precipitation by addition of diethyl ether to the chloroform solution yielded: methyl-3- aminopropionate hydrochloride.
20.2 g. (0.1 mole) of 1-chloro-2,4-dinitrobenzene and 16.8 g (0.2 mole) sodium bicarbonate was dissolved in 200 m1 of ethanol and 30 ml of water and heated to reflux. 18 g. (0.13 mole) of methyl 3-aminopropionate hydrochloride was then added into the solution while refluxing. After refluxing for 2% hours, the mixture was cooled and filtered. Recrystallization of the precipitate from water methanol yielded: N-(2- carbomethoxyethyl)-2,4-dinitroaniline. m.p. 9296C.
11.3 g. (0.042 mole) of N-(2-carbomethoxyethyl)- 2,4-dinitroaniline was dissolved in 150 ml of methanol and 31.6 g. (0.7 mole) of dimethylamine was then added. The mixture was heated to reflux for 10 hours, cooled and filtered yielding: N-[ 2- (N',N'dimethylcarboxamido)ethyl]-2.4-dinitroaniline. m.p. -143C.
10.2 g. (0.033 mole) of N-[2-(N,N'- dimethylcarboxamido)ethyl]-2,4-dinitroaniline was added to 200 ml of ethanol, 20 ml conc. hydrochloric acid and 0.75 g. of 5 percent platinum on charcoal. The mixture was hydrogenated in a Parr hydrogenator at an actual pressure of 9 psi. at room temperature for 40 minutes. The platinum catalyst was then recovered by filtration. The filtrate was alkalized with concentrated ammonium hydroxide and evaporated to dryness under vacuum. Recrystallization yielded: N'-[2-(N,N- dimethyl carboxamiido)ethyl]-2-nitro-pphenylenediamine. 1.4 g. of N -[2-(N,N-
EXAMPLE 2 A flask containing a mixture of 13.1 g. of 6-amino-nhexanoic acid (0.1 mole) and 14.8 g. (0.1 mole) of phthalic anhydride was heated in an oil bath at C until frothing of the mixture stopped (about 20 minutes). The solid resulting upon cooling was recrystallized from an ethanol/water mixture yielding: 6- phthalimido-n-hexanoic acid. m.p. 8182C.
18.4 g. (0.07 mole) of -phthalimido-n-hexanoic acid was suspended in 250 ml. of benzene and heated to reflux for one hour with a Dean-Stark condenser to remove water in the mixture. 14.65 g. (0.07 mole) of phosphorus pentachloride was then added and the mixture was heated at 60C (water bath) for 30 minutes. The benzene was then removed under vacuum. Recrystallization of the residue from benzene/petroleum ether (b.p. 3060C) yielded: 6-phthalimido-nhexanoyl chloride. m.p. 6468C.
18.1 g. (0.067 mole) of 6-phthalimido-n-hexanoyl chloride was dissolved in 100 ml of dry benzene and added slowly to 30 ml of dimethylamine and the mixture refluxed for 2 hours. The solvent was then removed under vacuum and the residual oil washed with water and dried with anhydrous calcium sulfate. The oil was then heated to reflux for 1 hour with 3.2 g. (0.1 mole) of hydrazine in 250 ml ethanol. After evaporation of the solvent, the dry residue was warmed to 50C for 10 minutes with 200 ml. of 2 N HCL. The mixture was then cooled to room temperature and filtered. Evaporation of the filtrate to dryness and recrystallization from ethanol/water yielded 6-amino-N,N- dimethyl-n-hexamide. m.p. 86-89C.
Using the procedure described in Example 1, N-[S- (N,N'-dimethylcarboxamido)pentyl]-2,4- dinitroaniline was prepared from 2,4-dinitrochloroben= zene and o-amino-N,N-dimethyl-n-hexamide. m.p. 121122C.
EXAMPLE 3 Using the procedure described in Example 1, N -[2- (N,N-dimethylcarboxamido)ethyl]-2-nitro-N, N -bis- (2-hydroxypropyl)-p-phenylenediamine was prepared from N-[2-(N,N-dimethylcarboxamido )ethyl]-2-nitrop-phenylenediamine and propylene oxide in place of ethylene oxide. A max. 520 nm.
EXAMPLE 4 Using the procedure described in Example 1, N -[2- (N-methylcarboxamido)ethyl]-2-nitro-N,N -bis-(2- hydroxyethyl)-p-phenylenediamine was prepared by using monomethylamine in place of dimethylamine. A max. 527 nm.
EXAMPLE 5 Using the procedure described in Example 1, N-[2- (carboxamido)ethyl]-2-nitro-N,N-bis-(2-hydroxyethyl-p-phenylenediamine was prepared by using ammonia'in place of dimethylamine. m.p. l36-l38C. max. 530 nm.
EXAMPLE 6 Using the procedure described in Example 2, N -[5- (carboxamido)pentyl]-2-nitro-N ,N-bis-(2-hydroxyethyl)-p-phenylenediamine was prepared by using ammonia in place of dimethylamine. A max. 535 nm.
EXAMPLE 7 A silver blue toning hair dye composition of medium intensity and suitable for gray hair was prepared containing the following ingredients:
Ingredients Amount Product of Example 1 2 g. Laurie diethanolamide 2 g. Propylene glycol 2 g. Water q.s. 100 g.
The ingredients were mixed together in the order listed above to provide a homogeneous dispersion, and the composition was applied to unbleached natural blonde and unbleached 50 percent gray hair for 30 minutes at a bath to hair ratio of 2.511 by weight at room temperature, producing in each case a light violet tone which did not wash out.
EXAMPLE 8 A silver blue toning dye having a light intensity and suitable for gray hair was prepared having the following composition:
ingredients Amount Product of Example 1 0.5 g. Laurie diethanolamide 2 g. Propylene glycol 2 g. Conc. ammonium hydroxide (28%) 3 g. Water q.s. g.
The composition was prepared and tested as described in Example 7, producing the same results. When applied to the hair for 60 minutes instead of 30, a medium violet tone was produced in each case.
EXAMPLE 9 A silve blue toning dye having a light intensity and suitable for gray hair is prepared having the following composition:
ingredients Amount Product of Example I 2 g. Lauric diethanolamide 2 g. Propylene glycol 2 g. Conc. ammonium hydroxide (28%) 3 g. Water q.s. 100 g.
The composition was prepared and tested as described in Example 7, producing a medium violet tone which did not wash out.
A similar composition in which the amount of active ingredient was 2.5 g. instead of 2 g. produced similar results.
EXAMPLE 10 A hair grooming lotion suitable for gray hair was prepared having the following composition:
Ingredients Amount Product of Example 1 2 g.
Commercial hair setting gel (no color imparted to hair) 98 g.
The ingredients were mixed together to form a homogeneous dispersion, and the composition was applied to unbleached natural blonde and unbleached 50 percent gray hair at room temperature and allowed to remain for 30 minutes, whereupon the composition was rinsed out, leaving a medium violet tone in each case.
EXAMPLE 1 l A silver blue shampoo toner suitable for gray hair was prepared having the following composition:
Ingredients Amount Product of Example l 5 g. Triethanolamine lauryl sulfate (40%) 35 g. Hydroxyethylcellulose 2.5 g. Water 61.5 g.
The ingredients were mixed together in the order named to form a homogeneous dispersion, and the composition was applied to unbleached natural blonde and unbleached 50 percent gray hair atroom temperature. permitted to remain for minutes and rinsed out, producing a light silver shade in each case.
We claim:
l. A hair dye composition comprising an aqueous carrier and as an active ingredient thereof a tinctorially effective amount of a compound of the formula 5. The composition of claim 3 wherein the alkalizing agent is diethanolamine.
6. A method of dyeing hair which method comprises applying to the hair an effective amount of a hair dye composition comprising an aqueous carrier and as an active ingredient thereof a tinctorially effective amount of a compound of the formula wherein R and R is each independently lower alkyl,
R and R is each independently C -C hydroxyalkyl, and n is an integer from one to six. 7. The method of claim 6 wherein the composition further includes an alkalizing agent.
8. The method of claim 7 wherein the alkalizing agent is diethanolamine.
9. The method of claim 6 wherein the tinctorially effective amount of the compound is from about 0.05 to about 5 percent of the weight of said composition.
Claims (8)
- 2. The composition of claim 1 wherein the compound is N1-(2-(N,N-dimethylcarboxamido)ethyl)-2-nitro-N4,N4-bis-(2-hydroxyethyl)-p -phenylenediamine.
- 3. The composition of claim 1 further including an alkalizing agent.
- 4. The composition of claim 1 wherein the tinctorially Effective amount of the compound is from about 0.05 to about 5 percent of the weight of said hair dye composition.
- 5. The composition of claim 3 wherein the alkalizing agent is diethanolamine.
- 6. A method of dyeing hair which method comprises applying to the hair an effective amount of a hair dye composition comprising an aqueous carrier and as an active ingredient thereof a tinctorially effective amount of a compound of the formula
- 7. The method of claim 6 wherein the composition further includes an alkalizing agent.
- 8. The method of claim 7 wherein the alkalizing agent is diethanolamine.
- 9. The method of claim 6 wherein the tinctorially effective amount of the compound is from about 0.05 to about 5 percent of the weight of said composition.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00090825A US3836326A (en) | 1970-11-18 | 1970-11-18 | Dyeing hair with nitro-substituted phenylene compounds |
GB5194371A GB1363937A (en) | 1970-11-18 | 1971-11-09 | Nitrosubstituted phenylene diamine compounds and compositions containing them |
CA127,266A CA1020952A (en) | 1970-11-18 | 1971-11-09 | Nitro-substituted phenylene compounds and compositions containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00090825A US3836326A (en) | 1970-11-18 | 1970-11-18 | Dyeing hair with nitro-substituted phenylene compounds |
Publications (1)
Publication Number | Publication Date |
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US3836326A true US3836326A (en) | 1974-09-17 |
Family
ID=22224501
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US00090825A Expired - Lifetime US3836326A (en) | 1970-11-18 | 1970-11-18 | Dyeing hair with nitro-substituted phenylene compounds |
Country Status (3)
Country | Link |
---|---|
US (1) | US3836326A (en) |
CA (1) | CA1020952A (en) |
GB (1) | GB1363937A (en) |
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US20040200011A1 (en) * | 2002-12-06 | 2004-10-14 | Luc Nicolas-Morgantini | Composition for the oxidation dyeing of keratin fibers, comprising at least one oxidation dye, at least one fatty alcohol, at least one associative polymer, and at least one C14-C30 alkyl sulphate |
US20140127824A1 (en) * | 2011-06-28 | 2014-05-08 | Mistral Detection Ltd. | Reagent method and kit for the detection of nitro aliphatic compounds |
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US5171889A (en) * | 1990-10-31 | 1992-12-15 | Clairol Incorporated | Compositions containing nitroaniline dyes having a carbamide substituent group |
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1970
- 1970-11-18 US US00090825A patent/US3836326A/en not_active Expired - Lifetime
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- 1971-11-09 GB GB5194371A patent/GB1363937A/en not_active Expired
- 1971-11-09 CA CA127,266A patent/CA1020952A/en not_active Expired
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US3121116A (en) * | 1961-03-31 | 1964-02-11 | Dow Chemical Co | Propynyl p-phenylene diamines |
US3420883A (en) * | 1963-11-26 | 1969-01-07 | Lever Brothers Ltd | N-alkyl-n-carbamylalkyl isopicramic acids |
US3168442A (en) * | 1964-06-12 | 1965-02-02 | Clairol Inc | Compositions and methods of dyeing human hair with nitro-p-phenylenediamines |
US3532743A (en) * | 1965-04-23 | 1970-10-06 | Oreal | Novel carboxymethylamino benzenes used in hair dyes |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040200011A1 (en) * | 2002-12-06 | 2004-10-14 | Luc Nicolas-Morgantini | Composition for the oxidation dyeing of keratin fibers, comprising at least one oxidation dye, at least one fatty alcohol, at least one associative polymer, and at least one C14-C30 alkyl sulphate |
US20080168609A1 (en) * | 2002-12-06 | 2008-07-17 | L'oreal S.A. | Composition for the oxidation dyeing of keratin fibers, comprising, at least one oxidation dye, at least one fatty alcohol, at least one associative polymer, and at least one C14-C30 alkyl sulphate |
US7695526B2 (en) * | 2002-12-06 | 2010-04-13 | L'oreal S.A. | Composition for the oxidation dyeing of keratin fibers, comprising, at least one oxidation dye, at least one fatty alcohol, at least one associative polymer, and at least one C14-C30 alkyl sulphate |
US20140127824A1 (en) * | 2011-06-28 | 2014-05-08 | Mistral Detection Ltd. | Reagent method and kit for the detection of nitro aliphatic compounds |
US9417226B2 (en) * | 2011-06-28 | 2016-08-16 | Mistral Detection Ltd | Reagent, method and kit for the detection of nitro aliphatic compounds |
Also Published As
Publication number | Publication date |
---|---|
CA1020952A (en) | 1977-11-15 |
GB1363937A (en) | 1974-08-21 |
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