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
  • A61K8/42—Amides
• • 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
• • 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
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
  • D06P1/642—Compounds containing nitrogen
  • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
  • D06P1/6491—(Thio)urea or (cyclic) derivatives
• • 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
• • 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
  • D06P3/3058—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts using metallisable or mordant dyes

Definitions

• This invention can be employed for dyeing either natural or synthetic polyamide fibers such as wool, silk, nylon or animal bristles, and particularly hair attached to the skin such as living human hair, furs, pelts, etc.
• R is a (lower) alkyl and each of R R and R, is hydrogen or a (lower) alkyl and wherein said urea derivatives have a melting point below 40 C.
• the term lower as used herein to modify alkyl refers to an alkyl having from 1 to 5 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert. butyl, amyl, and the like.
• the water solubility of the urea derivative is less than about at 25 C.
• the solvent must be a liquid so it can perform the function of a carrier for the 3,206,363 Patented Sept. 14, 1965 "ice dye.
• the maximum allowable temperature for dyeing hair on the human head is 40 C. and therefore the solvents must be liquid below this temperature.
• the prior art has disclosed some alkyl derivatives of urea to be incorporated in dyebaths for human hair none of the disclosed ureas is a liquid and none has a melting point below 40 C.
• those ureas disclosed by the prior art have been used in a process for coloring human hair that has nothing to do with the presently contemplated solvent dyeing process.
• urea itself is a salt-like, very polar compound; as a matter of fact urea and thiourea have the character of Zwitter Ions" (cf. H. Lecher and C. Heuck, Ann. 438, 176 (1924).
• Zwitter Ions cf. H. Lecher and C. Heuck, Ann. 438, 176 (1924).
• alkyl derivatives of urea the polar character is gradually diminished, the melting point decreases and the tetra-lower-alkyl-ureas are distillable liquids.
• Recent papers by T. Gaumann et al., Helv. Chim. Acta 41 1956, 1971 (1958) disclose dielectric constants and dipole moments of alkyl substituted ureas.
• urea itself has a dipole moment ,u -4.56 while tetramethylurea, tetraethylurea, tetrabutylurea and l,l-dimethyl-3,3-diethylurea have dipole moments a around 3.45 only and are liquids.
• the dyes used in the process of our invention are soluble in the urea derivative solvent and have a higher solubility in the urea solvents of this invention than in water. Generally such dyes have a low solubility in water such as less than about 0.5% and preferably less than 0.1% at 25 C.
• the preferred dyes used in this invention are the disperse dyes and the neutral premetallized dyes.
• Disperse dyes are well-known to the textile art and are used for dyeing cellulose acetate and other polyester fibers, and nylon. They are structurally characterized by the absence of solubilizing sulfonic acid groups. Aside from this requirement, they may belong to various chromphoric classes, such as to nitrodiphenylamines, as for example, Disperse Orange 15 (CI. 10350), to azo dyes, as for example, C.1. Disperse Orange 5 (CI. 11100), and to anthraquinones, as for example, Disperse Violet 4 (CI. 61105). The disperse dyes are well described in the textile literature.
• the neutral premetallized dyes also referred to herein as neutral dyeing metallized azo dyes, comprise particularly chromium and cobalt complexes of azo dyes with appropriate chelating groups, the ratio of metal: azo dye being 1:2. They are further characterized by the absence of solubilizing sulfonic acid groups.
• Such dyes are sold under a variety of tradenames, such as Cibalans, Irgalans, Irgacets, Capracyls, Lanasyns and others. Irgalans have been described in an article by G. Schetty, J. Soc. Dyers 8: Colourists 71, 705 (1955).
• lrgalan Orange RL which is the sodium-ammonium salt of the chromim complex of the azo dye obtained from diamtized 3-amino-4-hydroxyphenyl-methylsulfone coupled on 3'-chloro-l-phenyl-3-methyl-pyrazolone-5
• Irgalan Gray BL described in Example 13 of the same patent uses the same diazo component but the coupling component is the methylurethane of 1-amino-7-hydroxynaphthalene.
• Cibalans are dealt with in an article by C. Weidmaun, Am. Dyestuffs Reporter 43, 167 (1954).
• Cibalan Orange RI which is a chromium complex of 2-aminophenol-4-sulfonamide coupled on 1-p-tolyl-3-methyl-pyrazolone-5.
• the dyeing process of this invention can be employed over a wide pH range such as that of about 2 to 9, the preferred pH depending on the class of dye employed.
• an acid pH in the range of about 3-6 is preferred.
• the pH can be adjusted to the preferred value by the addition to the dyeing composition of various inorganic or organic acids or acid-salts, as for example, hydrochloric acid, sulfuric acid, ammonium sulfate, acetic acid, formic acid, citric acid, lactic acid or tartaric acid.
• urea derivatives employed in this invention which have a melting point less than 40 C.
• tetrapropylurea tetraethylurea
• 1,1- dipropyl 3,3 diethylurea 1,1 dibutyl-3 ethylurea
• tetrabutylurea tetrabutylurea
• the urea derivative is a tetraalkyl urea having from 2 to 3 carbon atoms in each alkyl chain, tetraethyl urea being preferred.
• the dyeing compositions of this invention contain a dye of low water solubility which also has some solubility in the solvent (such as a dye from the various classes of dyes mentioned hereinabove which are suitable for this invention), water and the alkyl urea solvent. Additionally the compositions can contain conventional dye additives such as thickeners, detergents, etc.
• the quantity of the various ingredients in the dyeing composition can vary over a wide range.
• the quantity of the urea derivative can preferably vary from about 0.1% to about 10% and particularly from about 1% to about 5% by weight of the dyeing composition.
• the dye can vary over a wide range such as that from about 0.001% to 5% and preferably from about 0.01% to about 2% by weight of the composition.
• the compositions are aqueous since they contain some water.
• the quantity of water is not critical and can vary over a wide range such as that from about 30%-99%, and particularly from 75% to 99% based on the weight of the composition.
• water is the major ingredient of the composition e.g., the composition contains at least 50% of water.
• the dyeing compositions of this invention can be formulated in conventional forms such as solutions, gels, pastes, emulsions, dispersions, and the like, and can be prepared by the conventional methods used in the dyeing art. Thus they can be prepared by dissolving or dispersing the dye in the urea derivative and adding this mixture to the water. Also, all the ingredients can be mixed simultaneously. A conventional blender or dispersing apparatus can be employed in order to facilitate solution or dispersion.
• the dyeing compositions can be applied to polyamide fibers by the conventional techniques known in the art. Illustratively when applied to living hair on the human head, they can be applied to the hair with a brush, sponge, or other means of contact until the hair is properly dyed.
• the reaction time or time of contact of the dyeing composition with the polyamide fibers is not critical and can vary over the wide range used in the dyeing art such as periods of about 5 minutes to two hours or more, and preferably from about to 60 minutes when used for dyeing living human hair.
• the dyeing on live hair is preferably effected at temperatures below 40 C. such as those from C. to 40 C. and preferably at ambient room temperatures such as those of about C. to C.
• Example I A homogeneous paste is prepared containing 0.2 g. of the dye, C.I. Disperse Violet 4 (Cl. 61105) which is lamino-4-methylamino-anthraquinone, 3 g. tetraethylurea, 0.1 g. citric acid, and 4 g. carboxymethylcellulose, as a thickening agent, in ml. water.
• the pH is adjusted to 3.5 with an additional small quantity of citric acid.
• the paste is poured on living normal gray hair on the human head and dyeing is allowed to proceed for 20 minutes at room temperature. The hair is then shampooed, rinsed and dried. The hair shows a strong, level violet color which is fast to rubbing and shampooing.
• the hair shows no uptake of dye.
• the above procedure and composition can be used with bleached hair and permanent-waved hair in place of normal gray hair, and the effect of adding tetraethylurea (as against the blank control) is even more pronounced with respect to the strength of dyeing observed.
• Example 2 The procedure of Example 1 is followed, except that in place of the dye of that example, there is used 0.2 g. of the ammonium salt of the 2:1, dye-to-metal, chromium complex, of the dye obtained by coupling 3-amino-4-hydroxyphenyl methyl sulfone diazo to N-carbomethoxy- S-amino-Z-naphthol.
• Normal gray hair, permanentwavcd hair and bleached hair are all dyed a uniform medium silver shade when the dyeing is performed in the presence of tetraethylurea. In the absence of tetraethylurea, there is obtained only a faint tint to a very weak dyeing.
• Example 3 A paste is prepared from 0.1 g. of the dye which is the mixed sodium-ammonium salt of the 2:1 chromium complex of the am compound obtained by coupling Z-aminophenol-4-sulfonamide diazo to p-cresol, and containing 2.5 g. tetraethylurea, 4 g. methylcellulose, enough water to bring the volume to 100 ml., and enough tartaric acid to bring the pH to 3.
• this dyeing composition is applied to normal gray hair, permanent-waved hair, or bleached hair, and allowed to impregnate the hair for 20 minutes at room temperature, all of the hair is dyed in strong level shades of brown, fast to rubbing and shampooing.
• a similar experiment with the omission of the tetraethylurea shows no dyeing of the normal gray hair, and weak tints on the other hair.
• Example 4 A paste consisting of 0.2 g. of the dye, C.I. Disperse Orange 5 (CI. 11100), which is the azo dye obtained by coupling diazotized 2,6 dichloro 4 nitroaniline onto N-phenyl-N-methy1ethano1amine, 3 g. tetraethylurea and 4 g. methylcellulose, made up to 100 ml. with water, and
• C.I. Disperse Orange 5 CI. 11100
• CI. 11100 the azo dye obtained by coupling diazotized 2,6 dichloro 4 nitroaniline onto N-phenyl-N-methy1ethano1amine, 3 g. tetraethylurea and 4 g. methylcellulose, made up to 100 ml. with water, and
• An aqueous dyeing composition containing: (a) from about 0.1% to of a urea derivative having a melting point less than 40 C. and having the formula:
• R R R and R are alkyl having from 1 to 5 carbon atoms; and (b) from about 0.001% to about 5% of an organic dye of low water solubility selected from the group consisting of a disperse dye, and neutral dyeing metallized azo dye.
• each of R R R and R is alkyl having from 2 to 3 carbon atoms.
• a method for dyeing living human hair on the head which comprises applying thereto an aqueous dyeing com position containing: (a) a urea derivative having a melting point less than 40 C. and having the formula:
• R R R and R are alkyl having from 1 to 5 carbon atoms; and (b) an organic dye of low water solubility selected from the group consisting of a disperse dye, and a neutral dyeing metallized azo dye.
• a method for dyeing living human hair on the head which comprises applying thereto at a temperature below 40 C. an aqueous dyeing composition containing: (a) a urea derivative having a melting point less than 40 C. and having the formula:
• R R R and R are alkyl having from 1 to 5 carbon atoms; and (b) an organic dye of low water solubility selected from the group consisting of a disperse dye, and a neutral dyeing metallized azo dye, said urea derivative being a solvent for said dye.
• a method for dyeing living human hair on the head which comprises applying thereto at a temperature below 40 C. an aqueous dyeing composition containing: (a) a urea derivative having a melting point less than 40 C. and having the formula:
• R R R and R are alkyl having from 1 to 5 carbon atoms; and (b) a low water-soluble disperse dye; said composition containing at least 50% of water and said urea derivative being a solvent for said dye.
• each of R R R and R, of the urea derivative is alkyl having from 2 to 3 carbon atoms.
• a method for dyeing living human hair on the head which comprises applying thereto at a temperature below 40 C. an aqueous dyeing composition containing: (a) a urea derivative having a melting point less than 40 C. and having the formula:
• R R R and R are alkyl having from 1 to 5 carbon atoms; and (b) a low water-soluble neutral dyeing metallizecl azo dye; said composition containing at least 50% of water and said urea derivative being a solvent for said dye.
• each of R R R and R of the urea derivative is alkyl having from 2 to 3 carbon atoms and the composition has a pH of about 3 to 6.
• An aqueous dyeing composition containing (a) from 0.1% to 10% of a tetraalkylurea derivative having a melting point less than 40 C. and a water solubility of less than about 10% at 25 C. and having the formula:
• R is alkyl having from 1 to 5 carbon atoms and (b) from 001% to 5% of a low water soluble organic dye having a solubility in water of less than about 5% at 25 C. and selected from the group consisting of disperse dyes and neutral dyeing metallized azo dye, said tetraalkylurea derivative being a solvent for said dye.
• a method for dyeing living human hair on the head which comprises applying thereto an aqueous dyeing composition containing (a) a tetraalkylurea derivative having 7 8 a melting point less than 40 C. end a water solubility of References Cited by the Examiner less than 10% at 25 C. and having the formula: UNITED STATES PATENTS 2,163,043 6/39 Kritchevsky 16788 5 2,551,056 5/51 Schetty 260149 R 3,098,013 7/63 Austin et a1. 167-88 :C o /R OTHER REFERENCES N Colour Index, 2nd Ed., vol.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (4)

Cited By (5)

• 1962
  • 1962-08-29 US US220143A patent/US3206363A/en not_active Expired - Lifetime
• 1963
  • 1963-08-06 GB GB30922/63A patent/GB979405A/en not_active Expired
  • 1963-08-19 DE DE19631444215 patent/DE1444215A1/de active Pending
  • 1963-08-23 CH CH43065A patent/CH465772A/de unknown

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