US3401003A - Diaminoanthraquinones and their use as human hair dyes - Google Patents
Diaminoanthraquinones and their use as human hair dyes Download PDFInfo
- Publication number
- US3401003A US3401003A US392607A US39260764A US3401003A US 3401003 A US3401003 A US 3401003A US 392607 A US392607 A US 392607A US 39260764 A US39260764 A US 39260764A US 3401003 A US3401003 A US 3401003A
- Authority
- US
- United States
- Prior art keywords
- parts
- hair
- agents
- cream
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000118 hair dye Substances 0.000 title description 5
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 title 1
- 210000004209 hair Anatomy 0.000 description 29
- 239000006071 cream Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 amino- Chemical class 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 238000009736 wetting 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
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 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 2
- 238000001035 drying Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- NNXSVNHFDAUPRN-UHFFFAOYSA-N 1,4-diamino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Cl)C=C2N NNXSVNHFDAUPRN-UHFFFAOYSA-N 0.000 description 1
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- GBAXGHVGQJHFQL-UHFFFAOYSA-N 1-(2-hydroxyethylamino)propan-2-ol Chemical compound CC(O)CNCCO GBAXGHVGQJHFQL-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- AGDJYJUPTJISCC-UHFFFAOYSA-N 1-sulfanylbutane-1-sulfonic acid Chemical compound CCCC(S)S(O)(=O)=O AGDJYJUPTJISCC-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000000341 volatile oil Substances 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
- A61K8/355—Quinones
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/264—Dyes with amino groups substituted by hydrocarbon radicals sulfonated
- C09B1/268—Dyes with amino groups substituted by hydrocarbon radicals sulfonated only sulfonated in a substituent
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
Definitions
- the invention relates to agents for dyeing of human hair and, more particularly, to certain substituted anthraquinone dyes, as hereinafter will become more apparent. These dyes have the advantage that they can be employed substantially at room temperature.
- anthraquinone derivatives for the dyeing of human hair is known. These derivatives contain, e.g., amino-, hydroxyl-, carboxylor sulfo groups in the nucleus.
- novel hair dyes are characterized by a content of anthraquinone compounds which are free of acid groups in the nucleus and which contain a side chain consisting of a hydrocarbon radical connected to the nucleus by way of an oxygen or nitrogen atom, this hydrocarbon radical further containing a secondary or, preferably, tertiary nitrogen atom in an aliphatic chain or else in a heterocyclic ring.
- anthraquinone dyes especially those are suited which contain a hydrocarbon group of the formula wherein n equals 14, and X denotes one of the following groups: C H N; a)2; 2)a aZ
- These anthraquinone derivatives can be manufactured by reacting aminoanthraquinones which contain a reactive halogen atom, an N02 or OH group, with compounds which contain in an aliphatic chain or in a heterocyclic ring at least a secondary, but preferably a tertiary, nitrogen group.
- these compounds must contain a group capable of reacting with the substituted anthraquinone, e.g., an OH group, an NH group or a halogen atom.
- pyridine-Z-carbinol pyridine-2- 3,401,003 Patented Sept. 10, 1968 ethanol
- 4-pico1ylamine 2-picolylchloride; dimethylaminoethanol; N-beta-oxethylpropanediamine-( 1,3); ethanolisopropanolamine; diethylenetriamine; triethylenetetramine; beta-oxethylurea; beta-oxethylthiourea; 3-allyloxy 2 oxypropylamine (l); N-beta-aminoethylmorpholine; and N-beta-oxethylmorpholine.
- the aminoanthraquinone radical must be free from acid groups in the nucleus, such as hydroxyl-, carboxylor sulfo-groups. However, it may contain other substituents, such as halogen or nitro groups.
- the hair dyes can be mixed with any desired wetting, dispersing and washing agents, preferably however with those which are anionic or nonionic. Suitable wetting, dispersing and Wash ing agents are, e.g., alkylbenzenesulfates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethan-olamides, ethylene adducts on fatty acids and fatty alcohols.
- the fixing quality of the dyes according to the invention remains good on the hair when admixed with the agents named above and does not diminish to any practical extent. Therefore, these dyes can be manufactured in the form of shampoos, particularly cream shampoos, which frequently are desirable in practice.
- thickeners such as methylcellulose, starch, higher fatty alcohols, Vaseline, paraffin oil, fatty acids; also essential oils and hair grooming agents, e.g., pantothenic acid and cholesterol, can be admixed.
- the additives are employed in the customary quantities.
- permanent waving agents also can be admixed to the novel hair dyeing agents.
- These permanent waving materials are based on compounds containing mercapto groups, e.g., thioglycolic acid, thiolactic acid, mercaptopropaneor mercaptobutanesulfonic acid.
- the novel hair dyes can be produced with these additives since the dyes have the advantage of stability even in the presence of the materials named so that storage presents no problem, even over prolonged periods of time.
- Human hair can be dyed with these novel hair dyeing agents without the aid of heating caps or similar devices since temperatures below 40 C., and preferably room temperature, are required for the dyeing process.
- the pH of the agents may range from 7 to 10, preferably from 8.5 to 9.5.
- the agents can be used for dyeing naturally grey hair or for redyeing dyed hair from one color to another. The hair thus dyed. is not affected by repeated washing nor -by rubbing or other friction.
- a permanent wave treatment is imparted to hair dyed with the agents according to this invention, a change in color or hue does not occur. Finally, the fixing of the color on the hair is very good.
- EXAMPLE 4 34 parts 1,4-diamino-S-nitroanthraquinone and 135 parts N-beta-oxethylpropanediamine-( 1,3) were reacted at 30 for 15 hours, and were allowed to stand for another 48 hours at room temperature. In contrast to the preceding example, no additon of NaOH was made. Thereafter, the reaction mixture was poured into 500 parts ice water, suction-filtered and dried. 33 parts of blue powder of Formula 4 thus were obtained:
- EXAMPLE 6 14.2 parts 1,4 diamino S-nitroanthraquinone were reacted with 100 parts diethylenetriamine at for 15 hours. The reaction mixture was poured into 1000 parts water and suction-filtered. After drying at 60 in vacuo, 15 parts of a dark blue powder were obtained having the Formula 6:
- EXAMPLE 7 14.2 pants 1,4 diamino S-nitroanthraquinone were reacted wtih 7.1 parts ;3oxethylthiourea (respectively 6.8 parts ,B-oxethylurea) and 2.4 parts powdered NaOH in 100 parts benzene at for 10 hours. Benzene was: removed in vacuo, the residue was treated with diluted HCl and suction-filtered. 15 parts of a blue powder were obtained having the following constitution as shown in Formula 7 respectively 8:
- n is a Whole number from 1 to 4 and X is selected from the group consisting of -C H N; -N(CH -NHCO-NH and NI-I-CSNH 5.
- a process for the dyeing of human hair which comprises applying to said hair for approximately 15 to 30 mintues and substantially at room temperature a cream having as the active ingredient 0.1 to 5 percent by weight, calculated on total composition, of 1,4-diaminoanthnaquinone free of hydroxyl-, carboxyland su1fo-groups in the anthraquinone ring; a hydrogen in said ring being replaced by an atom selected from the group consisting of oxygen and nitrogen; said atom being linked to a group wherein n is a whole number from 1 to 4 and X is selected from the group consisting of -C H N; -N(CH -NH-CONH and -NHCS-NH References Cited UNITED STATES PATENTS 3,123,605 3/1964 Turetzky et
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1963T0024643 DE1248865C2 (de) | 1963-09-04 | 1963-09-04 | Mittel zum faerben von haaren |
| DET24640A DE1203915B (de) | 1963-09-04 | 1963-09-04 | Haarfaerbemittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3401003A true US3401003A (en) | 1968-09-10 |
Family
ID=25999757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US392607A Expired - Lifetime US3401003A (en) | 1963-09-04 | 1964-08-27 | Diaminoanthraquinones and their use as human hair dyes |
| US392586A Expired - Lifetime US3368942A (en) | 1963-09-04 | 1964-08-27 | Water soluble aminoanthraquinone hair dyes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US392586A Expired - Lifetime US3368942A (en) | 1963-09-04 | 1964-08-27 | Water soluble aminoanthraquinone hair dyes |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US3401003A (de) |
| BE (1) | BE652619A (de) |
| CH (1) | CH486245A (de) |
| DE (1) | DE1203915B (de) |
| DK (1) | DK112755B (de) |
| FI (2) | FI42859B (de) |
| GB (2) | GB1005915A (de) |
| LU (1) | LU46884A1 (de) |
| NL (2) | NL144831B (de) |
| NO (1) | NO116772B (de) |
| SE (2) | SE324429B (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051155A (en) * | 1975-12-15 | 1977-09-27 | Allied Chemical Corporation | Anthraquinone dyes |
| US5314505A (en) * | 1991-11-01 | 1994-05-24 | Clairol, Inc. | Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1050863A (de) * | 1964-02-05 | |||
| SE7609628L (sv) * | 1976-08-31 | 1978-03-01 | Danielsson Karl Victor | Komposition for fergning av har |
| US5112359A (en) * | 1990-06-04 | 1992-05-12 | Clairol, Inc. | Hair colorants |
| US5961664A (en) * | 1997-07-10 | 1999-10-05 | Bristol-Myers Squibb Company | Direct hair dye compositions and methods containing novel anthraquinone mixtures |
| EP1820826A1 (de) * | 2006-02-09 | 2007-08-22 | DyStar Textilfarben GmbH & Co. Deutschland KG | Farbstoffe und Haarfaerbezusammensetzungen |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB807241A (en) * | 1955-08-30 | 1959-01-14 | Bayer Ag | Anthraquinone dyestuffs |
| US3123605A (en) * | 1960-01-08 | 1964-03-03 | Basic anthraquinone dyestuffs | |
| US3125586A (en) * | 1960-01-08 | 1964-03-17 | Quaternary ammonium salts of z-amino- | |
| US3192117A (en) * | 1961-02-23 | 1965-06-29 | Therachemie Chem Therapeut | Hair dye comprising substituted anthraquinones in shampoo base |
| US3232934A (en) * | 1959-06-25 | 1966-02-01 | Allied Chem | Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2730534A (en) * | 1952-12-31 | 1956-01-10 | Gen Aniline & Film Corp | Anthraquinone dyestuffs |
| BE553139A (de) * | 1955-12-10 | |||
| US3168441A (en) * | 1961-07-31 | 1965-02-02 | Clairol Inc | Blue anthraquinone dye |
| US3253876A (en) * | 1963-04-12 | 1966-05-31 | Eastman Kodak Co | Textile dyeing using disazo dyes |
-
1963
- 1963-09-04 DE DET24640A patent/DE1203915B/de active Pending
-
1964
- 1964-07-13 NL NL646407966A patent/NL144831B/xx not_active IP Right Cessation
- 1964-08-27 US US392607A patent/US3401003A/en not_active Expired - Lifetime
- 1964-08-27 US US392586A patent/US3368942A/en not_active Expired - Lifetime
- 1964-09-02 GB GB35863/64A patent/GB1005915A/en not_active Expired
- 1964-09-02 GB GB35859/64A patent/GB1005913A/en not_active Expired
- 1964-09-03 NO NO154628A patent/NO116772B/no unknown
- 1964-09-03 DK DK434864AA patent/DK112755B/da unknown
- 1964-09-03 BE BE652619D patent/BE652619A/xx unknown
- 1964-09-03 NL NL6410275A patent/NL6410275A/xx unknown
- 1964-09-04 CH CH1157864A patent/CH486245A/de not_active IP Right Cessation
- 1964-09-04 FI FI1882/64A patent/FI42859B/fi active
- 1964-09-04 SE SE10636/64A patent/SE324429B/xx unknown
- 1964-09-04 LU LU46884D patent/LU46884A1/xx unknown
- 1964-09-04 FI FI1883/64A patent/FI42989B/fi active
- 1964-09-04 SE SE10635/64A patent/SE320766B/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB807241A (en) * | 1955-08-30 | 1959-01-14 | Bayer Ag | Anthraquinone dyestuffs |
| US3232934A (en) * | 1959-06-25 | 1966-02-01 | Allied Chem | Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms |
| US3123605A (en) * | 1960-01-08 | 1964-03-03 | Basic anthraquinone dyestuffs | |
| US3125586A (en) * | 1960-01-08 | 1964-03-17 | Quaternary ammonium salts of z-amino- | |
| US3192117A (en) * | 1961-02-23 | 1965-06-29 | Therachemie Chem Therapeut | Hair dye comprising substituted anthraquinones in shampoo base |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051155A (en) * | 1975-12-15 | 1977-09-27 | Allied Chemical Corporation | Anthraquinone dyes |
| US5314505A (en) * | 1991-11-01 | 1994-05-24 | Clairol, Inc. | Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain |
Also Published As
| Publication number | Publication date |
|---|---|
| SE324429B (de) | 1970-06-01 |
| LU46884A1 (de) | 1965-03-04 |
| NO116772B (de) | 1969-05-19 |
| SE320766B (de) | 1970-02-16 |
| NL6407966A (de) | 1965-03-05 |
| BE652619A (de) | 1965-03-03 |
| DE1203915B (de) | 1965-10-28 |
| GB1005915A (en) | 1965-09-29 |
| CH486245A (de) | 1970-02-28 |
| DK112755B (da) | 1969-01-13 |
| FI42859B (de) | 1970-08-03 |
| GB1005913A (en) | 1965-09-29 |
| NL6410275A (de) | 1965-03-05 |
| NL144831B (nl) | 1975-02-17 |
| FI42989B (de) | 1970-09-02 |
| US3368942A (en) | 1968-02-13 |
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