US2934396A - Process of dyeing hair with 5, 6-dihydroxyindole - Google Patents
Process of dyeing hair with 5, 6-dihydroxyindole Download PDFInfo
- Publication number
- US2934396A US2934396A US711180A US71118058A US2934396A US 2934396 A US2934396 A US 2934396A US 711180 A US711180 A US 711180A US 71118058 A US71118058 A US 71118058A US 2934396 A US2934396 A US 2934396A
- Authority
- US
- United States
- Prior art keywords
- solution
- hair
- minutes
- contact
- rinsed
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- 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
- D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
Definitions
- an oxidizing agent such assodium bromate, a persalt such as sodium perborate or ammonium persulphate, or simply hydrogen peroxide.
- an oxidizing agent such assodium bromate, a persalt such as sodium perborate or ammonium persulphate, or simply hydrogen peroxide.
- A'ccordingto the present invention a process for dyeing live hair and like materials consists essentially in impregnating the hair or like material at room temperature.
- the pH-value of the aqueous 5:6-dihydroxy-indole solution to be applied in a first step for carrying out the invention maybe obtained in various ways.
- the sequestering agent may be, for
- any other reactant the pH-vaiue of such a solution being of course slightly acid. It is also possible to acidity this aqueous solution more or less strongly, for example by means of an inorganc acid, an organic acid, e.g. formic, acetic or monochloroacetic acid, or any compound containing at least one acid hydrogen atom.
- the concentration of 5:6-dihydroxy-indole in the solution as applied to the hair or other material may vary within fairly wide limits. Generally it will be between 0.1% and 10% and preferably between 1% and 2% by weight of the solution.
- aqueous solution as employed here means any solution the principal solvent. of which is water. It is of course possible, without departing from the scope of the invention, to use inthe preparation of such a solution Water alone or in admixture with water-rniscilzrle solvents, notably mixtures of,
- aqueous solu-' tion aqueous solu-' tion
- a reducing agent such as, for example, an alkali metal sulphite, bisulphite or hydrosulphite
- this addition prefer ably being made first, i.e. before the 5:6-dihydroxy-indole is added.
- the stability of aqueous solutions of 5:6-dihydroxy-indole may also be enhanced by adding thereto a small quantity, preferably 0.2% to 0.5%, of a sequestering agent, i.e.
- a compound capable of forming complexes with ions of alkadne-earth metals or of heavy metals often existing example, ethylenediaminc-tetracetic acid or one of its salts, such as that known under the trade mark Trilon B.
- the shade is then developed in situ by applying to the hair or other material an aqueous solution capable of inducing oxidation and/orpolymerization of the 5:6-di-" hydroxy-indole. s
- this oxidizing agent as also the lengthof time during which it should be maintained in contact with the hair or the material to be dyed, depends to some extent upon the final shade which it is desired to obtain.
- the oxygen of theambient air if desired ozonized.
- the development of the shade which amounts to the rapid fixing of the atmospheric oxygen bythe hair or similar material impregnated with 5:6-dihyclroxy-indole, is effected by applying in a second step as" a developing medium an aqueous solution containing an alkalizing agent consisting preferably of ammonia, a basic ammo nium salt such as ammonium carbonate or triamrnoniumcontact with the hair or similar material for 10 to 60 minutes as necessary for the penetration of the reactants. The hair is then rinsed clear with water and dried.
- the development of the shade which is initiated by the alkalization, may proceed for some time, this process thenconstituting a progressive dyeing process.
- an aqueous solution of an oxidizing agent such as, for example, hydrogen peroxide, or an alkali metal or ammonium iodate, periodate or persulphate or an alkali metal salt of an N-chlorinated derivative of a sulphonamide.
- an oxidizing agent such as, for example, hydrogen peroxide, or an alkali metal or ammonium iodate, periodate or persulphate or an alkali metal salt of an N-chlorinated derivative of a sulphonamide.
- the pH of this aqueous oxidizing solution, applied in the second place, may be adjusted to any desired value, either acid, neutral or alkaline, by the addition of any appropriate reactant, for example an inorganic or organic acid, a salt having an acid reaction, a buffer, a salt having a basic reaction or a base such as ammonia or an organic amine.
- any appropriate reactant for example an inorganic or organic acid, a salt having an acid reaction, a buffer, a salt having a basic reaction or a base such as ammonia or an organic amine.
- the choice of the most suitable value depends mainly, but not solely, upon thenature of the oxidizing agent employed.
- the latter is hydrogen peroxide, an alkali metal or ammonium iodate or periodate or an alkali metal salt of an N-chlorinated derivative of a sulphonamide
- it is generally preferable to operate in a basic medium, whereas the operation is preferably carried out in an acid medium if the oxidizing agent is an alkali metal or ammonium persulphate.
- the oxidizing agent employed is an iodate or a periodate, it is preferable not to operate at a pH-value lower than 3 and to avoid the use of a strong inorganic acid for adjusting the pH to the desired value.
- the concentration of the oxidizing agent in the aqueous solution may be chosen between fairly wide limits, depending upon the desired shade and upon the own solubility of the specific oxidizing agent which is to be used.
- the quantity of oxidizing agent to be employed corresponds to 0.5 to g. per 100 cc. of solution, the volume of oxidizing solution to be employed being substantially the same as the quantity of dihydroxyindole solution.
- the oxidizing solution employed in the second step is acid or neutral, i.e. free from ammonia and organic amines, it is probable that the pigment formed results from the formation of the quinone corresponding to 5,6-dihydroxyindole.
- analytical data has shown that if the oxidizing solutions are rendered alkaline by means of ammonia or an amine, the molecule of the pigment obtained contains nitrogen issuing from the ammonia or the amine employed. The same holds true when the oxidation is effected through the intermediary of ambient air and in the presence of ammonia or an amine, according to the first embodiment of the invention.
- a quantity of a neutral, strongly ionized inexpensive electrolyte such as, for example, sodium chloride or sodium sulphate.
- the dyeing process according to the invention may be carried out, not only by means of aqueous solutions as referred to above, but also by means of creams, pastes or jellies, the adjustment to the required consistency being efiected by any method usual in hair dyeing.
- 5,6-dihydroxy-indole under the abovedefined conditions, constituting the object of the present invention may be combined with that of dior triphenols capable of dyeing hair and other keratinous fibres at room temperature under analogous conditions such as those defined, for example, in our applications Nos. 709,479 and 709,602, both filed January 17, 1958.
- Example I illustrates the case where the development is effected in a basic medium and by oxidation in the ambient air, while the other examples illustrate cases where the development is effected by means of an oxidizing solution.
- Example I An impregnating solution having the following composition is prepared:
- Naturally white or nearly white live hair is impregnated with this solution. After contact for 20 minutes, the excess solution is blotted off, for example by means of a towel, and an aqueous solution having the following composition is then applied:
- Example II An impregnating solution as set forth in Example I is applied to naturally white live hair.
- Example III Sodium chloride g 4 Water 100 20% ammonia cc 17 Hydrogen peroxide (20 vol.) (6% of H 0 cc 0.3
- This second solution isleft in contact with the hair for 30 minutes, and the hair is then rinsed, shampooed, rinsed again and dried.
- the hair is dyed jet-black.
- Example IV Almost white live hair is impregnated with an impregnating solution as set forth in Example I.
- This solution is left in contact with the hair for 20 minutes, and the hair is then rinsed, shampooed, rinsed again and dried.
- the hair is dyed medium ash-blond.
- Example V Nearly white live hair is impregnated with an impregnating solution as defined in Example I. After a period of contact of 20, minutes, the excess solution is blotted deep black.
- Example VI Naturally white or nearly white hair is impregnated with an impregnating solution as defined in Example I.
- Example VII Naturally white live hair is treated with an impregnating solution as defined in Example I.
- This solution is left in contact with the hair for 30 minutes, whereafter the excess solution is blotted off and an aqueous solution having the following composition is applied to the hair.
- Example VIII Almost white live hair is impregnated with an impregnating solution as defined in Example I, which is left in contact therewith for 20 minutes. After blotting off the excess solution, the following solution is applied:
- Chloramine T sodium N-chloro-p-toluene-sulphonamide
- Example IX Naturally white live hair is impregnated with the following impregnating solution: 5,6-dihydroxy-indole g 1 Acetic acid cc 0.5 Water to make 100 cc.
- This solution is 3.3. This solution is left in contact with the hair for 15 minutes. The excess solution is then blotted off and an aqueous 4% sodium iodate solution is then applied to hair. After 15 minutes, the hair is rinsed, shampooed, rinsed again and dried. A dark grey shade is obtained.
- Example X A solution having the following composition is prepared:
- the pH-value of such a solution is 6.2. This solution.
- Example IX is aqueous 4% sodium iodate solution applied to the hair. After this solution has been allowed to act for 15 minutes, the hair is rinsed, shampooed, rinsed again and dried. The hair is dyed a dark grey, which is not, however, as dark as the shade obtained in Example IX.
- Example XI Naturally white live hair is treated with an impregnating solution as defined in Example IX.
- the hair is dyed in a greyshade which is a little lighter than that obtained in Example X.
- Example XII A solution having the following composition is prepared: 5,6-dihydroxy-indole g.. 1 Water cc solution is applied thereto. After 15 minutes, the hair is rinsed, shampooed, rinsed again and dried. A medium grey is obtained.
- Example XIV An aqueous solution containing 1% by weight of 5,6- dihydroxy-indole is applied to naturally white live hair. This solution is left in contact with the hair for 15 minutes. The excess solution is then blotted off and an aqueous 5% sodium persulphate solution is applied. After 15 minutes, the hair is rinsed, shampooed, rinsed again and dried. The shade obtained is medium grey.
- Example XV Naturally white live hair is impregnated with an impregnating solution as defined in Example I.
- Example XVI Almost white live hair is impregnated with an impregnating solution as defined in Example I which is left incontact therewith for 20 minutes. The excess solution is then blotted 0E and a solution having the following composition is applied thereto:
- This solution is left in contact with the hair for 20 minutes. drying, the hair is dyed a fine deep black.
- Example XVIII A solution having the following composition is employed to impregnate almost white live hair:
- a process for dyeing live human hair -'and;keratinous fibers at room temperature by means of 5,6-dihydroxyindole which comprises impregnating said materials in a first step with an aqueous solution of said dihydroxyindole adjusted to a pH value of less than 7 and, after having allowed impregnation to proceed for 5 to 60 minutes and having blotted off the excess solution, applying in a second step onto the impregnated material an aqueous solution containing a.
- nitrogenous base selected from the roup consisting of ammonia, basic ammonium salts and organic amines and further containing an oxidizing agent selectedrfr'om the group consisting of hydrogen peroxide, alkali metal and ammonium bromates, iodates, periodates, perborates and persulphates and alkali metal salts of N-chlorinated ,sulphonamides.
- an oxidizing agent selectedrfr'om the group consisting of hydrogen peroxide, alkali metal and ammonium bromates, iodates, periodates, perborates and persulphates and alkali metal salts of N-chlorinated ,sulphonamides.
- a process for dyeing live human hairandlkeratinous fibers at room temperature by means of 5,6-dihydr0xyindole which comprises impregnating said materials .in a first step with an aqueous solution containing from 0.1% to 10% by weight of 5,6dihydroxyindole and adjusted to a pH-value of less than 7 and, after having allowed impregnation to proceed for 5 to 60 minutes and blotted ofi the excess solution, applying in a second step onto the impregnated material an aqueous solution containing a nitrogenous base selected from the group consisting of ammonia, basic ammonium salts and organic amines and further containing an oxidizing agent selected from the group consisting of hydrogen peroxide, alkali metal and ammonium bromates, iodates, periodates, perborates and persulphates and alkali metal salts of IN-chlorinated sulphonamides.
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- 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)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1097086X | 1957-02-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2934396A true US2934396A (en) | 1960-04-26 |
Family
ID=9618478
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US711180A Expired - Lifetime US2934396A (en) | 1957-02-02 | 1958-01-27 | Process of dyeing hair with 5, 6-dihydroxyindole |
Country Status (7)
Country | Link |
---|---|
US (1) | US2934396A (de) |
BE (1) | BE564450A (de) |
CH (1) | CH347814A (de) |
DE (1) | DE1097086B (de) |
FR (1) | FR1166172A (de) |
GB (1) | GB823503A (de) |
NL (2) | NL107681C (de) |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3124412A (en) * | 1964-03-10 | Continuous- dyeing method for fibrous | ||
US3215605A (en) * | 1962-04-25 | 1965-11-02 | Revlon | Method for coloring hair and other keratinaceous fibers with metal salts |
US3337411A (en) * | 1961-10-26 | 1967-08-22 | Interpal S A | Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair |
US3993436A (en) * | 1973-12-01 | 1976-11-23 | Shiseido Co., Ltd. | Dyeing live hair with melanin precursors |
DE3530270A1 (de) * | 1985-08-24 | 1987-02-26 | Goldwell Gmbh | Verfahren zum oxidativen faerben von menschlichen oder tierischen haaren sowie haarfaerbemittel zur durchfuehrung des verfahrens |
DE3720143A1 (de) * | 1986-06-16 | 1987-12-17 | Oreal | Faerbemittel fuer menschliche keratinfasern in form eines schaumes auf der grundlage von 5,6-dihydroxyindol |
US4776857A (en) * | 1986-11-21 | 1988-10-11 | Repligen Corporation | Use of hydroxylated indoles as dye precursors |
US4804385A (en) * | 1986-01-20 | 1989-02-14 | L'oreal | Process for dyeing keratinous fibres with 5,6-dihydroxy-indole combined with an iodide and dyeing composition employed |
US4885006A (en) * | 1986-11-17 | 1989-12-05 | L'oreal | Process for dyeing keratinous fibres with indole derivatives combined with an iodide |
WO1990001919A1 (en) * | 1988-08-19 | 1990-03-08 | The Gillette Company | Polymeric skin colorant |
US4992077A (en) * | 1986-08-21 | 1991-02-12 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
US5006127A (en) * | 1986-08-21 | 1991-04-09 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
US5096455A (en) * | 1989-07-21 | 1992-03-17 | L'oreal | Process for dyeing keratinous fibres employing an indole dye and at least one para-phenylenediamine containing a secondary amino group absent an oxidant other than air |
US5173085A (en) * | 1982-12-07 | 1992-12-22 | Clairol Incorporated | Hair dyeing process and compositons package |
US5207798A (en) * | 1990-03-08 | 1993-05-04 | L'oreal | Process for dyeing keratinous fibres, at acid ph using 6- or 7-monohydroxyindoles and the compositions employed |
US5273550A (en) * | 1991-09-26 | 1993-12-28 | Clairol Incorporated | Process and kit for dyeing hair |
US5279618A (en) * | 1991-09-26 | 1994-01-18 | Clairol Incorporated | Process and kit for dyeing hair |
US5346509A (en) * | 1988-05-12 | 1994-09-13 | Clairol Incorporated | Process for dyeing hair by the sequential treatment of hair with metal ion-containing composition and with a dye composition containing 5,6-dihydroxyindole-2-carboxylic acid and certain derivatives thereof |
US5350424A (en) * | 1992-10-13 | 1994-09-27 | Combe Incorporated | Dyestuff composition for the gradual dyeing of hair by atmospheric oxidation and process using the same |
US5368610A (en) * | 1993-04-20 | 1994-11-29 | Clairol Incorporated | Use of metal salts and chelates together with chlorites as oxidants in hair coloring |
US5413612A (en) * | 1992-04-29 | 1995-05-09 | Clairol Incorporated | Composition and method for dyeing hair with indolic compounds in the presence of a chlorite oxidant |
US5518505A (en) * | 1991-01-21 | 1996-05-21 | L'oreal | Compositions and methods for the dyeing of keratinous fibers with oxidation dye precursors, indole derivative couplers and oxidizing agents |
US5792220A (en) * | 1997-05-16 | 1998-08-11 | Bristol-Myers Squibb Company | Dyeing hair with melanin procursors in the presence of iodate and peroxide |
US6160127A (en) * | 1998-07-15 | 2000-12-12 | Bristol-Myers Squibb Company | Process for the preparation of substituted indoles |
US6238439B1 (en) | 1990-06-21 | 2001-05-29 | L'oreal | Method for dyeing keratinous fibers with indole compounds, compositions and devices for implementation |
US6537330B1 (en) | 1998-06-23 | 2003-03-25 | Henkel Kommanditgesellschaft Auf Aktien | Colorants |
US6569211B2 (en) | 1991-11-19 | 2003-05-27 | Henkel Kommanditgesellschaft Auf Aktien | 5,6-dihydroxyindolines as additives for hair dyeing preparations |
US6719811B1 (en) * | 1990-05-19 | 2004-04-13 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation colorants for keratin fibers |
US6743264B2 (en) | 2002-02-14 | 2004-06-01 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Two step permanent coloring of hair |
US20050000035A1 (en) * | 2003-07-03 | 2005-01-06 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Method of providing more vibrant, natural and long-lasting color to hair |
US20050000036A1 (en) * | 2003-07-03 | 2005-01-06 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Hair dyeing method including an aligning step |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE593306A (de) * | 1959-07-24 | |||
FR2390158A1 (fr) * | 1977-05-10 | 1978-12-08 | Oreal | Compositions liquides de colorants de la famille des indoles destinees a la teinture des cheveux |
FR2421607A1 (fr) * | 1978-04-06 | 1979-11-02 | Oreal | Procede de teinture des fibres keratiniques en deux temps par variation de ph |
CA1201067A (en) * | 1982-12-07 | 1986-02-25 | Keith Brown | Hair dyeing process and composition |
LU86314A1 (fr) * | 1986-02-20 | 1987-09-10 | Oreal | Procede de teinture des fibres keratiniques humaines avec le 5,6-dihydroxyindole et un anion metallique |
LU86346A1 (fr) * | 1986-03-06 | 1987-11-11 | Oreal | Compositions tinctoriales pour fibres keratiniques a base de derives d'indole et composes nouveaux |
LU86833A1 (fr) * | 1987-04-02 | 1988-12-13 | Oreal | Procede de teinture des fibres keratiniques avec le 5,6-dihydroxyindole associe a un iodure et une composition de peroxyde d'hydrogene a ph alcalin |
LU86947A1 (fr) * | 1987-07-17 | 1989-03-08 | Oreal | Procede de teinture des fibres keratiniques,en particulier humaines,avec le 5-(hydroxy ou-methoxy)6-hydroxyindole |
LU87097A1 (fr) * | 1987-12-30 | 1989-07-07 | Oreal | Procede de teinture des fibres keratiniques et composition de teinture mettant en oeuvre du 5,6-dihydroxyindole,un colorant direct nitre et un iodure |
LU87113A1 (fr) * | 1988-01-26 | 1989-08-30 | Oreal | Procede de teinture des fibres keratiniques et composition de teinture mettant en oeuvre du 5,6-dihydroxyindole,un colorant quinonique et iodure |
LU87128A1 (fr) * | 1988-02-08 | 1989-09-20 | Oreal | Composition de teinture des fibres keratiniques mettant en oeuvre du 5,6-dihydroxyindole et au moins une paraphenylenediamine disubstituee sur l'un des groupements amino et procede de mise en oeuvre |
DE3935128A1 (de) * | 1989-10-21 | 1991-04-25 | Henkel Kgaa | Oxidationsfaerbemittel, dessen herstellung und anwendung |
FR2663651B1 (fr) * | 1990-06-21 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec des composes indoliques, compositions et dispositifs de mises en óoeuvre. |
FR2722686B1 (fr) | 1994-07-22 | 1996-08-30 | Oreal | Set, procede, dispositif et composition de teinture des fibres keratiniques |
FR2915882A1 (fr) * | 2007-05-09 | 2008-11-14 | Oreal | Composition tinctoriale comprenant une base d'oxydation aminopyrazolopyridine et un colorant particulier |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1133594A (en) * | 1914-10-24 | 1915-03-30 | Halkyard Mfg Company | Lacing-stud-setting machine. |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB745531A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
GB745532A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
BE593306A (de) * | 1959-07-24 |
-
0
- NL NL224577D patent/NL224577A/xx unknown
- BE BE564450D patent/BE564450A/xx unknown
- NL NL107681D patent/NL107681C/xx active
-
1957
- 1957-02-02 FR FR1166172D patent/FR1166172A/fr not_active Expired
-
1958
- 1958-01-27 GB GB2702/58A patent/GB823503A/en not_active Expired
- 1958-01-27 US US711180A patent/US2934396A/en not_active Expired - Lifetime
- 1958-01-30 DE DES56768A patent/DE1097086B/de active Pending
- 1958-01-31 CH CH347814D patent/CH347814A/fr unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1133594A (en) * | 1914-10-24 | 1915-03-30 | Halkyard Mfg Company | Lacing-stud-setting machine. |
Cited By (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3124412A (en) * | 1964-03-10 | Continuous- dyeing method for fibrous | ||
US3337411A (en) * | 1961-10-26 | 1967-08-22 | Interpal S A | Oxidation dyestuffs with ascorbic acid or salts thereof for dyeing living human hair |
US3215605A (en) * | 1962-04-25 | 1965-11-02 | Revlon | Method for coloring hair and other keratinaceous fibers with metal salts |
US3993436A (en) * | 1973-12-01 | 1976-11-23 | Shiseido Co., Ltd. | Dyeing live hair with melanin precursors |
US5173085A (en) * | 1982-12-07 | 1992-12-22 | Clairol Incorporated | Hair dyeing process and compositons package |
DE3530270A1 (de) * | 1985-08-24 | 1987-02-26 | Goldwell Gmbh | Verfahren zum oxidativen faerben von menschlichen oder tierischen haaren sowie haarfaerbemittel zur durchfuehrung des verfahrens |
US4808190A (en) * | 1986-01-20 | 1989-02-28 | L'oreal | Process for dyeing keratinous fibres with 5,6-dihydroxy-indole and hydrogen peroxide, preceded or followed by a treatment with an iodide |
US4804385A (en) * | 1986-01-20 | 1989-02-14 | L'oreal | Process for dyeing keratinous fibres with 5,6-dihydroxy-indole combined with an iodide and dyeing composition employed |
DE3720143A1 (de) * | 1986-06-16 | 1987-12-17 | Oreal | Faerbemittel fuer menschliche keratinfasern in form eines schaumes auf der grundlage von 5,6-dihydroxyindol |
US4900326A (en) * | 1986-06-16 | 1990-02-13 | L'oreal | Dye composition for human keratinous fibres in the form of foam, based on 5,6-dihydroxyindole |
DE3720143C2 (de) * | 1986-06-16 | 1998-09-24 | Oreal | Färbemittel für menschliche Keratinfasern in Form eines Schaumes auf der Grundlage von 5,6-Dihydroxyindol |
US4992077A (en) * | 1986-08-21 | 1991-02-12 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
US5006127A (en) * | 1986-08-21 | 1991-04-09 | Goldwell Gmbh | Agent for the oxidative dyeing of hair, method for the preparation of the agent and use of the agent |
US4885006A (en) * | 1986-11-17 | 1989-12-05 | L'oreal | Process for dyeing keratinous fibres with indole derivatives combined with an iodide |
US4776857A (en) * | 1986-11-21 | 1988-10-11 | Repligen Corporation | Use of hydroxylated indoles as dye precursors |
US5346509A (en) * | 1988-05-12 | 1994-09-13 | Clairol Incorporated | Process for dyeing hair by the sequential treatment of hair with metal ion-containing composition and with a dye composition containing 5,6-dihydroxyindole-2-carboxylic acid and certain derivatives thereof |
WO1990001919A1 (en) * | 1988-08-19 | 1990-03-08 | The Gillette Company | Polymeric skin colorant |
US5096455A (en) * | 1989-07-21 | 1992-03-17 | L'oreal | Process for dyeing keratinous fibres employing an indole dye and at least one para-phenylenediamine containing a secondary amino group absent an oxidant other than air |
US5207798A (en) * | 1990-03-08 | 1993-05-04 | L'oreal | Process for dyeing keratinous fibres, at acid ph using 6- or 7-monohydroxyindoles and the compositions employed |
US6719811B1 (en) * | 1990-05-19 | 2004-04-13 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation colorants for keratin fibers |
US6238439B1 (en) | 1990-06-21 | 2001-05-29 | L'oreal | Method for dyeing keratinous fibers with indole compounds, compositions and devices for implementation |
US5518505A (en) * | 1991-01-21 | 1996-05-21 | L'oreal | Compositions and methods for the dyeing of keratinous fibers with oxidation dye precursors, indole derivative couplers and oxidizing agents |
US5279618A (en) * | 1991-09-26 | 1994-01-18 | Clairol Incorporated | Process and kit for dyeing hair |
US5273550A (en) * | 1991-09-26 | 1993-12-28 | Clairol Incorporated | Process and kit for dyeing hair |
US5279617A (en) * | 1991-09-26 | 1994-01-18 | Clairol Incorporated | Process and kit for dyeing hair |
US6569211B2 (en) | 1991-11-19 | 2003-05-27 | Henkel Kommanditgesellschaft Auf Aktien | 5,6-dihydroxyindolines as additives for hair dyeing preparations |
US5413612A (en) * | 1992-04-29 | 1995-05-09 | Clairol Incorporated | Composition and method for dyeing hair with indolic compounds in the presence of a chlorite oxidant |
US5350424A (en) * | 1992-10-13 | 1994-09-27 | Combe Incorporated | Dyestuff composition for the gradual dyeing of hair by atmospheric oxidation and process using the same |
US5368610A (en) * | 1993-04-20 | 1994-11-29 | Clairol Incorporated | Use of metal salts and chelates together with chlorites as oxidants in hair coloring |
WO1998051269A1 (en) * | 1997-05-16 | 1998-11-19 | Bristol-Myers Squibb Company | Dyeing hair with melanin precursors in the presence of iodate and peroxide |
US5792220A (en) * | 1997-05-16 | 1998-08-11 | Bristol-Myers Squibb Company | Dyeing hair with melanin procursors in the presence of iodate and peroxide |
US6537330B1 (en) | 1998-06-23 | 2003-03-25 | Henkel Kommanditgesellschaft Auf Aktien | Colorants |
US6160127A (en) * | 1998-07-15 | 2000-12-12 | Bristol-Myers Squibb Company | Process for the preparation of substituted indoles |
US6743264B2 (en) | 2002-02-14 | 2004-06-01 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Two step permanent coloring of hair |
US20050000035A1 (en) * | 2003-07-03 | 2005-01-06 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Method of providing more vibrant, natural and long-lasting color to hair |
US20050000036A1 (en) * | 2003-07-03 | 2005-01-06 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Hair dyeing method including an aligning step |
US7060111B2 (en) | 2003-07-03 | 2006-06-13 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Method for providing more vibrant, natural and long-lasting color to hair |
US7074244B2 (en) | 2003-07-03 | 2006-07-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Hair dyeing method including an aligning step |
Also Published As
Publication number | Publication date |
---|---|
DE1097086B (de) | 1961-01-12 |
CH347814A (fr) | 1960-07-31 |
GB823503A (en) | 1959-11-11 |
NL224577A (de) | |
FR1166172A (fr) | 1958-11-04 |
BE564450A (de) | |
NL107681C (de) |
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