US3558259A - Human hair dyeing with aminophenols - Google Patents
Human hair dyeing with aminophenols Download PDFInfo
- Publication number
- US3558259A US3558259A US645520A US3558259DA US3558259A US 3558259 A US3558259 A US 3558259A US 645520 A US645520 A US 645520A US 3558259D A US3558259D A US 3558259DA US 3558259 A US3558259 A US 3558259A
- Authority
- US
- United States
- Prior art keywords
- hair
- aminophenol
- hydroxy
- methoxy
- solution
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- 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
-
- 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
- D06P1/32—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 oxidation dyes
Definitions
- R is selected from the group consisting of hydrogen and alkyl
- R is selected from the group consisting of hydroxy and alkyl
- R, which can be in position or 6 on the ring is selected from the group consisting of hydrogen, halogen, hydroxy and alkyl.
- This invention relates to improvements in processes for the dyeing of hair and to new compositions suitable for one step keratin fiber and hair dyeing.
- a number of processes for dyeing keratinic fibers and notably hair are at present known, among the most commonly employed of these processes are those which are oxidation dyes whose coloration results from polymerization under oxidizing conditions.
- the oxidation dyes employed are almost exclusively mixtures of aromatic diamines and aromatic aminophenols, generally known as bases, in combination with substances, generally called modifiers, such as substituted or unsubstituted monoand polyphenols. It is thus possible, by using a relatively limited number of aromatic bases and phenols, to obtain a fairly wide range of colorations, the proportions of the various constituents which enter into the composition of the dye bath being emperically varied.
- the formation of haircoloring pigments from these mixtures results from a series of very complex chemical reactions which necessitate either the use of an oxidizing substance, hydrogen peroxide, or the presence of a substance having an alkaline reaction, which is generally ammonia. It is also known that by increasing the hydrogen peroxide and ammonia content there is obtained what is known as a decolorizing dye, there being simultaneously produced a decoloration of the hair to be dyed and a hair coloration in the desired shade.
- each of the selected bases employed develops its own shade. Consequently, an extensive range of commercially necessary shades may be made available merely by employing a number of these products, the final shade obtained being the component of the individual shades of the starting materials.
- the dyeing solution comprises no oxidizing agent and no modifier and its pH value is equal to or higher than 7, viz from 7 to 11, the necessary oxidation being induced by atmospheric oxygen.
- EXAMPLE 8 Preparation of 6-methy1-4-hydroxy-2-aminophenol 6-methyl-4-methoxy-2-aminophenol is refluxed with a concentrated hydrobromic acid solution. After cooling, the hydrobromide of 6-methyl-4-hydroxy-2-aminophenol is filtered and separated. M.P. 225-228 C. (dec.).
- a dyeing solution according to the invention is prepared by mixing:
- a human hair dye composition comprising water and an effective amount of 6-brom0-4-methoxy-2-aminophenol having a pH of about 7 to 11.
- a human hair dye composition comprising water and an efiective amount of 4-methyl-5-hydroxy-2-aminophenol having a pH of about 7 to 11.
- a human hair dye composition comprising water and an effective amount of 4-methyl-S-hydroxy-2-methylaminophenol having a pH of about 7 to 11.
- a human hair dye composition comprising water and an effective amount of 5-chloro-4-hydroxy-2-aminophenol having a pH of about 7 to 11.
- a human hair dye composition comprising water and an effective amount of 5-methyl-4-hydroxy-2-aminophenol having a pH of about 7 to 11.
- a human hair dye composition comprising water and an effective amount of 5-methoxy-4-hydroxy-2-aminophenol having a pH of about 7 to 11.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR903703A FR1374983A (fr) | 1962-07-11 | 1962-07-11 | Nouveau procédé de teinture des cheveux et nouvelles solutions tinctoriales utilisables à cet effet |
FR940212A FR84324E (fr) | 1963-07-03 | 1963-07-03 | Nouveau procédé de teinture des cheveux et nouvelles solutions tinctoriales utilisables à cet effet |
US6848870A | 1970-08-31 | 1970-08-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3558259A true US3558259A (en) | 1971-01-26 |
Family
ID=27246678
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US645519A Expired - Lifetime US3666812A (en) | 1962-07-11 | 1967-06-12 | Diamino phenol hair dyeing compounds |
US645520A Expired - Lifetime US3558259A (en) | 1962-07-11 | 1967-06-12 | Human hair dyeing with aminophenols |
US645522A Expired - Lifetime US3546293A (en) | 1962-07-11 | 1967-06-12 | Amino phenols |
US00068488A Expired - Lifetime US3738799A (en) | 1962-07-11 | 1970-08-31 | Dyeing human hair with 2-aminophenols |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US645519A Expired - Lifetime US3666812A (en) | 1962-07-11 | 1967-06-12 | Diamino phenol hair dyeing compounds |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US645522A Expired - Lifetime US3546293A (en) | 1962-07-11 | 1967-06-12 | Amino phenols |
US00068488A Expired - Lifetime US3738799A (en) | 1962-07-11 | 1970-08-31 | Dyeing human hair with 2-aminophenols |
Country Status (6)
Country | Link |
---|---|
US (4) | US3666812A (xx) |
BE (1) | BE634643A (xx) |
CH (1) | CH415965A (xx) |
DE (1) | DE1492064A1 (xx) |
GB (1) | GB987342A (xx) |
NL (1) | NL295194A (xx) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3899288A (en) * | 1971-12-02 | 1975-08-12 | Jean Galerne | Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid |
JPS5176377A (en) * | 1974-09-18 | 1976-07-01 | Goodrich Co B F | Jugotaifuchakuno haijohoho |
US4031160A (en) * | 1965-05-06 | 1977-06-21 | Societe Anonyme Dite: L'oreal | 2-Amino-4-hydroxy-5-chloro toluene and the hydrochloride thereof |
US4035422A (en) * | 1968-08-14 | 1977-07-12 | L'oreal | 2,6-Dimethyl-4-substituted amino phenol couplers |
US4129414A (en) * | 1975-03-03 | 1978-12-12 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers |
US4212645A (en) * | 1974-01-18 | 1980-07-15 | Lever Brothers Company | Hair dyeing composition containing an aryldiamine and a substituted catechol |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU56491A1 (xx) * | 1968-07-15 | 1970-01-15 | ||
US3953462A (en) * | 1973-10-29 | 1976-04-27 | Xeerox Corporation | Imaging process |
FR2362116A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
DE3027128A1 (de) * | 1979-07-18 | 1981-02-12 | Fuji Photo Film Co Ltd | O-aminophenolverbindungen |
DE3038284C2 (de) * | 1980-10-10 | 1985-08-22 | Wella Ag, 6100 Darmstadt | Mittel und Verfahren zur oxidativen Färbung von Haaren |
US4566876A (en) * | 1983-03-10 | 1986-01-28 | Clairol Incorporated | Meta-phenylenediamine coupler compounds and oxidative hair dye compositions and methods using same |
US5202487A (en) * | 1988-09-13 | 1993-04-13 | L'oreal | 2-substituted para-aminophenols and their use for dyeing keratinous fibres |
FR2637282B1 (fr) * | 1988-09-13 | 1990-12-07 | Oreal | Para-aminophenols 2-substitues et leur utilisation pour la teinture des fibres keratiniques |
FR2638453B1 (fr) * | 1988-10-28 | 1991-06-07 | Oreal | Ortho-aminophenols 5-substitues, procede pour les preparer et leur utilisation pour la teinture d'oxydation des fibres keratiniques |
US5409503A (en) * | 1990-05-31 | 1995-04-25 | Wella Aktiengesellschaft | Oxidation hair dye with a content of 5-aminophenyl derivatives, process for oxidative dyeing of hair and new 5-aminophenol derivatives |
US5041674A (en) * | 1990-06-14 | 1991-08-20 | Dowelanco | Process and intermediates for the preparation of 2,6-difluoroaniline |
DE4438129A1 (de) * | 1994-10-27 | 1996-05-02 | Schwarzkopf Gmbh Hans | Neue substituierte 2,4-Diaminophenole, Verfahren zu ihrer Herstellung und Haarfärbemittel |
DE19826456A1 (de) * | 1998-06-13 | 1999-12-16 | Schwarzkopf Gmbh Hans | Neue 3,4-Diaminophenolderivate und deren Verwendung |
ATE463229T1 (de) * | 2004-08-16 | 2010-04-15 | Procter & Gamble | Haarfärbemittel enthaltend 2-amino-3,5- substituierte phenolverbindungen und deren verwendung |
CA2576170A1 (en) * | 2004-08-16 | 2006-03-02 | The Procter & Gamble Company | 2-(amino or substituted amino)-5, 6-substituted phenol compounds, dyeing compositions containing them, and use thereof |
WO2016051799A1 (ja) * | 2014-10-01 | 2016-04-07 | 学校法人同志社 | 2-アミノヒドロキノン誘導体及びタウ凝集阻害剤 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB479865A (en) * | 1936-08-13 | 1938-02-14 | Wilfred William Groves | Manufacture of ortho-aminophenols |
DE1096552B (de) * | 1955-11-25 | 1961-01-05 | Monsavon L Oreal Soc | Mittel zum Faerben von lebenden Haaren |
US3184387A (en) * | 1955-11-25 | 1965-05-18 | Oreal | Process for dyeing hair with substituted 2, 4-diaminophenols |
FR1137922A (fr) * | 1955-11-25 | 1957-06-05 | Oreal | Procédé et composition pour teindre les cheveux vivants et fibres analogues |
NL102837C (xx) * | 1958-04-15 |
-
0
- BE BE634643D patent/BE634643A/xx unknown
- NL NL295194D patent/NL295194A/xx unknown
-
1963
- 1963-07-10 DE DE19631492064 patent/DE1492064A1/de not_active Ceased
- 1963-07-11 CH CH865463A patent/CH415965A/fr unknown
- 1963-07-11 GB GB27554/63A patent/GB987342A/en not_active Expired
-
1967
- 1967-06-12 US US645519A patent/US3666812A/en not_active Expired - Lifetime
- 1967-06-12 US US645520A patent/US3558259A/en not_active Expired - Lifetime
- 1967-06-12 US US645522A patent/US3546293A/en not_active Expired - Lifetime
-
1970
- 1970-08-31 US US00068488A patent/US3738799A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4031160A (en) * | 1965-05-06 | 1977-06-21 | Societe Anonyme Dite: L'oreal | 2-Amino-4-hydroxy-5-chloro toluene and the hydrochloride thereof |
US4035422A (en) * | 1968-08-14 | 1977-07-12 | L'oreal | 2,6-Dimethyl-4-substituted amino phenol couplers |
US3899288A (en) * | 1971-12-02 | 1975-08-12 | Jean Galerne | Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid |
US4212645A (en) * | 1974-01-18 | 1980-07-15 | Lever Brothers Company | Hair dyeing composition containing an aryldiamine and a substituted catechol |
JPS5176377A (en) * | 1974-09-18 | 1976-07-01 | Goodrich Co B F | Jugotaifuchakuno haijohoho |
JPS5916561B2 (ja) * | 1974-09-18 | 1984-04-16 | ザ ビ− エフ グツドリツチ カムパニ− | 重合体付着の排除方法 |
US4129414A (en) * | 1975-03-03 | 1978-12-12 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers |
Also Published As
Publication number | Publication date |
---|---|
US3546293A (en) | 1970-12-08 |
US3738799A (en) | 1973-06-12 |
US3666812A (en) | 1972-05-30 |
BE634643A (xx) | |
GB987342A (en) | 1965-03-24 |
CH415965A (fr) | 1966-06-30 |
NL295194A (xx) | |
DE1492064A1 (de) | 1969-12-11 |
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