US3368942A - Water soluble aminoanthraquinone hair dyes - Google Patents

Water soluble aminoanthraquinone hair dyes Download PDF

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Publication number
US3368942A
US3368942A US392586A US39258664A US3368942A US 3368942 A US3368942 A US 3368942A US 392586 A US392586 A US 392586A US 39258664 A US39258664 A US 39258664A US 3368942 A US3368942 A US 3368942A
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US
United States
Prior art keywords
hair
agents
parts
cream
dyeing
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
Application number
US392586A
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English (en)
Inventor
Kaiser Wilhelm Jakob
Sturm Alfons
Boosen Karl-Josef
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Therachemie Chemische Therapeutische GmbH
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Therachemie Chemische Therapeutische GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE1963T0024643 external-priority patent/DE1248865C2/de
Application filed by Therachemie Chemische Therapeutische GmbH filed Critical Therachemie Chemische Therapeutische GmbH
Application granted granted Critical
Publication of US3368942A publication Critical patent/US3368942A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 dyeing agents based on anthraquinone of a constitution which permits their application substantially at room temperature.
  • oxidation dyes which contain aromatic diamines or polyphenols for dyeing of human hair are known. These dyes have the disadvantage that they must be developed with the aid of oxidizers, such as H 0 or perborates.
  • hair dyes containing directly acting dyes e.g., anthraquinone derivatives which are substituted in the nucleus by amino-, hydroxyl-, carboxylor sulfo groups.
  • anthraquinone compounds known for dyeing of human hair dyeing at temperatures ranging from 40 to 60 C. is required. It therefore becomes necessary to use heating caps and similar devices on the human head to attain the required temperatures.
  • the hitherto known anthraquinone hair dyes are difficultly soluble so that they had been employed solely as dispersion. dyes.
  • amino-anthraquinone dyes are employed having the generic Formulae 1 and/or 2;
  • R is hydrogen or an alkyl group having 1-3 carbon atoms
  • X is an aliphatic group having 1-6 carbon atoms or else a phenyl group containing a further group rendering the compound water-soluble.
  • anthraquinone dyestuifs to be considered for the purpose those are especially suited which contain 3,368,942 Patented Feb. 13, 1968 a water-soluble group such as SO H, -OH or COOH. It is understood that the corresponding alkalior ammonium salts and also the monoand diethanolamino salts can be employed equally well.
  • the dyes can be mixed with any desired wetting, dispersing and washing agents, especially those of anionic or nonionic character. Particularly to be considered are alkylbenzene sulfonates, fatty alcohol sulfates, alkyl sulfonates, fatty acid ethanolamides, ethylene adducts on fatty acids and fatty alcohols.
  • the dyeability of the dyeing agents named above remains good even in mixture with the wetting or washing agents. This facilitates the production of the hair dyeing agents in the form of shampoos, especially of cream shampoos. The latter often are desired in practice.
  • thickeners may be added to the agents according to the invention e.g., methylcellulose, starch, higher fatty alcohols, Vaseline, parafiin oil, fatty acids; also essential oils and hair grooming agents, such as pantothenic acid or cholesterol.
  • the additives named are admixed in the commonly used quantities. Wetting or dispersing agents are present in qantities of 0.5-30 percent by weight, thickeners in amounts of 0.1-25 percent by weight, calculated on the total composition. The concentration of the dyes them selves amounts to up to 5 percent by weight, but preferably 0.1 to 2 percent, of the total composition.
  • permanent waving agents may be added to the novel hair dyeing agents.
  • These waving agents are based on compounds containing mercapto groups, e.g., thioglycolic acid, thiolactic acid, mercaptopropaneor mercaptobutanesulfonic acid.
  • the hair dyeing agents may be produced containing these additives since the dyestuffs are stable in their presence.
  • the new hair dyeing agents allow dyeing of human hair without resorting to heating caps or similar devices since they are applied at temperatures below 40 C., and preferably at room temperature. Their pH may range from 7 to 10, preferably from 8.5 to 9.5.
  • the agents may I serve for coloring gray hair or for applying a new color to any color hair.
  • the hair thus dyed is extremely resistant to fading due to washing or friction, e.g., rubbing.
  • a permanent wave is applied to hair thus dyed, a change in the color or hue does not occur.
  • the dyes fix well on human hair and, in any of the mixtures described above, can be stored practically indefinitely.
  • Example 1 11.4 parts 1,4-diamino-S-nitroanthraquinone, 11 parts N-methyltaurine and 0.8 part powdered NaOH were mixed into 60 parts nitrobenzene and the temperature held at 50 C. for one-half hour. After that, the mixture was heated at C. for 12 hours. The reaction mixture then was refined by separating the nitrobenzene and alkali.
  • the dye thus obtained had the Formula 3 and imparted to gray hair a strong blue color with a purplish hue when applied for 20 minutes at 25 C. in an ammonia solution of a pH of 9.5.
  • Example 2 8 parts of a fatty alcohol mixture (C -C and 10 parts fatty alcohol sulfate (C -C were heated to 90 C. and emulsified with 60 parts water. Into this emulsion the dye obtained as described in Example 1, together with 1 part NH OH and 8 parts water, were stirred. A cream thus was obtained having a pH of substantially 9.5. This cream, applied to naturally gray hair, dyed the same purple-blue at room temperature. The hair had a strong hue and did not discolor upon washing.
  • Example 3 Hair of red color is obtained when the cream described in Example 2, in lieu of the dye used therein, contains an anthraquinone dye of Formula 4:
  • Example 5 1 part anthraquinone dye of Formula 7 was incorporated in a shampoo cream. The latter had been produced by heating a mixture of 4.5 parts cetyl alcohol, 4.5 parts stearyl alcohol, 1.5 parts fatty alcohol mixture (C -C and 10 parts fatty alcohol sulfate (C -C to 98 C., addition of the dye and emulsification with 78 parts water. The pH of the cream was adjusted to 9.5 with ammonia.
  • Example 6 Hair of red color is obtained when the cream described in Example 5, in lieu of the dye used therein, contains an anthraquinone dye of Formula 8:
  • This dye is produced by reacting 2-chloro-l,4-diaminoanthraquinone with (omega)-amino-heptylic acid. The reaction is carried out in the presence of solid potassium hydroxide and in solvents such as xylene.
  • Example 7 1 part of anthraquinone dye of formula ([JaHr IIIII: El) lTI-OHz-CHa-S 03H was mixed into a hair cream as described in Example 5, except that the pH was adjusted to 8.5. This cream dyed naturally grey hair blue at room temperature within a treatment of 15 minutes. The dye is produced by reacting l,4-diamino-5-nitroanthraquinone with N-propyl-taurin in presence of solid NaOH and nitrobenzene as solvent.
  • Example 8 14.1 parts of 1,4-diamino-5-nitr0anthraquinone and 50 parts monoethanolamine were mixed and the temperature held at 70 C. for 15 hours under stirring. After that, the surplus of monoethanolamine was distilled in vacuo, thereafter 50 parts water were added and the reaction mixture neutralized with aqueous HCl, filtered and the residue was dried at C. in vacuo.
  • the dye thus obtained had the Formula 10 IIHI: O IIQHCIDCIIZQH wherein R is selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms; and X is selected from the group consisting of alkylene of 1 to 6 carbon atoms and phenyl, said alkylene and phenyl having an end group selected from sulfo-, hydroxyland carboxyl, and their alkali metal, ammonium, monoand diethanolamine salts.
  • agents as defined in claim 1 wherein X is (CH SO H 3.
  • said compounds are incorporated in amounts from 0.1 to 5 percent by weight, calculated on the total composition, in a cream composed of substances selected from the group consisting of nonionic and anionic surfactants, thickeners, essential oils, hair grooming agents, permanent Waving agents, and mixtures thereof.
  • a process for the dyeing of human hair which comprises applying to said hair for approximately 15 to 30 minutes and substantially at room temperature a cream having as active dyeing ingredient an efiYective amount of a compound selected from the group consisting of NH2 0 I ll and I OI NH2 wherein R is selected from the group consisting of hydrogen and alkyl having 1-3 carbon atoms, and X is selected from the group consisting of alkylene of 1 to 6 carbon atoms and phenyl, said alkylene and phenyl having an end group selected from sulfo, hydroxyl and carboxyl, and their alkali metal, ammonium, monoand diethanolamine salts.
  • a process for the dyeing of human hair which comprises applying to said hair for approximately 15 to 30 minutes and substantially at room temperature a cream having as active dyeing ingredient 0.1 to 5 percent by weight, calculated on total composition, of a compound selected from the group consisting of r t" t w I'QX and I Y Y 1 NH2 0 IIIX O NHz References Cited UNITED STATES PATENTS 2,730,534 1/1956 Hoefle et al. 260374 X 3,168,441 2/1965 Bil et al. 167-88 3,253,876 5/1966 Wilcox et a1 839 X ALBERT T. MEYERS, Primary Examiner.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US392586A 1963-09-04 1964-08-27 Water soluble aminoanthraquinone hair dyes Expired - Lifetime US3368942A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DET24640A DE1203915B (de) 1963-09-04 1963-09-04 Haarfaerbemittel
DE1963T0024643 DE1248865C2 (de) 1963-09-04 1963-09-04 Mittel zum faerben von haaren

Publications (1)

Publication Number Publication Date
US3368942A true US3368942A (en) 1968-02-13

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Family Applications (2)

Application Number Title Priority Date Filing Date
US392586A Expired - Lifetime US3368942A (en) 1963-09-04 1964-08-27 Water soluble aminoanthraquinone hair dyes
US392607A Expired - Lifetime US3401003A (en) 1963-09-04 1964-08-27 Diaminoanthraquinones and their use as human hair dyes

Family Applications After (1)

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

Country Status (11)

Country Link
US (2) US3368942A (de)
BE (1) BE652619A (de)
CH (1) CH486245A (de)
DE (1) DE1203915B (de)
DK (1) DK112755B (de)
FI (2) FI42859B (de)
GB (2) GB1005913A (de)
LU (1) LU46884A1 (de)
NL (2) NL144831B (de)
NO (1) NO116772B (de)
SE (2) SE324429B (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531502A (en) * 1964-02-05 1970-09-29 Oreal Anthraquinone dyes
US5314505A (en) * 1991-11-01 1994-05-24 Clairol, Inc. Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain
US5961664A (en) * 1997-07-10 1999-10-05 Bristol-Myers Squibb Company Direct hair dye compositions and methods containing novel anthraquinone mixtures

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4051155A (en) * 1975-12-15 1977-09-27 Allied Chemical Corporation Anthraquinone dyes
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
EP1820826A1 (de) * 2006-02-09 2007-08-22 DyStar Textilfarben GmbH & Co. Deutschland KG Farbstoffe und Haarfaerbezusammensetzungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2730534A (en) * 1952-12-31 1956-01-10 Gen Aniline & Film Corp Anthraquinone dyestuffs
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

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1150652B (de) * 1955-08-30 1963-06-27 Bayer Ag Faerben von Polyacrylnitrilfasern
BE553139A (de) * 1955-12-10
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
US3125586A (en) * 1960-01-08 1964-03-17 Quaternary ammonium salts of z-amino-
US3123605A (en) * 1960-01-08 1964-03-03 Basic anthraquinone dyestuffs
NL275142A (de) * 1961-02-23

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2730534A (en) * 1952-12-31 1956-01-10 Gen Aniline & Film Corp Anthraquinone dyestuffs
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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531502A (en) * 1964-02-05 1970-09-29 Oreal Anthraquinone dyes
US5314505A (en) * 1991-11-01 1994-05-24 Clairol, Inc. Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain
US5961664A (en) * 1997-07-10 1999-10-05 Bristol-Myers Squibb Company Direct hair dye compositions and methods containing novel anthraquinone mixtures

Also Published As

Publication number Publication date
NL6410275A (de) 1965-03-05
NO116772B (de) 1969-05-19
GB1005913A (en) 1965-09-29
DK112755B (da) 1969-01-13
GB1005915A (en) 1965-09-29
CH486245A (de) 1970-02-28
LU46884A1 (de) 1965-03-04
NL6407966A (de) 1965-03-05
SE324429B (de) 1970-06-01
SE320766B (de) 1970-02-16
DE1203915B (de) 1965-10-28
US3401003A (en) 1968-09-10
NL144831B (nl) 1975-02-17
BE652619A (de) 1965-03-03
FI42859B (de) 1970-08-03
FI42989B (de) 1970-09-02

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