Bristol-Myers Squibb Compnay

Clairol Incorporated

Other

Linas R Stasaitis

Yuh-Guo Pan

Mu-Ill Lim

John D O'Donoghue

Yuo-Guo Pan

Mu-III Lim

Gottfried Wenke

Alexander C Chan

James S Anderson

Michael Y Wong

Michael Y M Wong

Mu-lll Lim

Coupler for use in oxidative hair dyeing

1-(2,5-Diaminophenyl)ethanol useful as a primary intermediate for the oxidative dyeing of hair.

Primary intermediate for use in oxidative hair dyeing

5-Nitroisatin is reacted with sodium hydroxide to produce an &agr;-keto acid sodium salt that is reduced with borane-tetrahydrofuran complex and then hydrogenated to produce 1-(2,5-diaminophenyl)ethylene glycol, a novel compound useful as a primary intermediate in the production of oxidative hair dyes.

Primary intermediate in oxidative hair dyeing

Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula at least one coupler comprising a compound of the formula:

The invention provides compositions and methods for the oxidative coloring of human hair. The compositions of the invention contain as a primary intermediate at least one aminophenol of the formulas: ##STR1## or a cosmetically acceptable salt thereof, and at least one pyrazolone coupler of the formulas: ##STR2## or a cosmetically acceptable salt thereof. The compositions may also contain one or more other primary intermediates and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations.

Hair dyeing compositions containing 2-chloro-  and

Compounds of Formula II ##STR1## wherein R.sub.3 is --COOCH.sub.3, --COCH.sub.3 or --COCH.sub.2 CH.sub.3 and R.sub.4 is hydrogen or R.sub.3 is hydrogen and R.sub.4 is --OCH.sub.3, --OC.sub.2 CH.sub.3, --OCH.sub.2 CH.sub.2 OH or --OCH.sub.2 CH.sub.2 OCH.sub.3 are storage stable and can be used in oxidative hairdye systems in place of the storage unstable 2-methyl-1-naphthol. Advantageously, it has been found to produce the same colors as 2-methyl-1-naphthol.

Storage stable 2-methyl-1-naphthol couplers

The novel primary intermediate, 1-(5-amino-2-hydroxyphenyl)ethane-1,2-diol and a method for producing same, are disclosed. The novel intermediate can be employed as a replacement for p-aminophenol in oxidation dye formulations.

Substituted p-aminophenol, process of preparation and use in dyeing hair

Anthraquinone compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are methyl and R.sub.3 is propyl, or R.sub.1 and R.sub.2 are ethyl and R.sub.3 is methyl and A is a cosmetically acceptable anion, are combined neutral, with semipermanent direct dyes in hair dyeing compositions.

Hair dye compositions containing anthraquinone dyes having a quaternary

The invention provides compositions and methods containing novel bis-(2,4-diaminophenoxy)benzene coupling compounds, and cosmetically acceptable salts thereof, for use with conventional primary intermediate dye compounds and oxidizing agents for the oxidative coloring of human hair. The compositions of the invention may also contain other components typically used in oxidative hair dye preparations to impart intense and lasting coloration to hair.

BIS-(2-4-diaminophenoxy) benzenes and their use as coupling components

Compounds of Formula II ##STR1## wherein R.sub.3 is --COOCH.sub.3, --COCH.sub.3 or --COCH.sub.2 CH.sub.3 and R.sub.4 is hydrogen or R.sub.3 is hydrogen and R.sub.4 is --OCH.sub.3, --OCH.sub.2 CH.sub.3, --OCH.sub.2 CH.sub.2 OH or --OCH.sub.2 CH.sub.2 OCH.sub.3 are storage stable and can be used in oxidative hairdye systems in place of the storage unstable 2-methyl-1-naphthol. Advantageously, it has been found to produce the same colors as 2-methyl-1-naphthol.

A one pot process is provided in which a Mannich base of the formula 5 is reacted with acetic anhydride to produce a diacetate derivative. Without any intermediate isolation, the derivative is hydrogenated to produce a reaction mixture containing 1-acetoxy-2-methylnaphthalene which is readily precipitated from the reaction mixture by addition of water. ##STR1##

Synthesis of 1-acetoxy-2-methylnaphthalene

Compounds of Formula II ##STR1## wherein R.sub.3 is --COCH.sub.3, --COCH.sub.3 or --COCH.sub.2 CH.sub.3 and R.sub.4 is hydrogen or R.sub.3 is hydrogen and R.sub.4 is --OCH.sub.3, --OCH.sub.2 CH.sub.3, --OCH.sub.2 CH.sub.2 OH or --OCH.sub.2 CH.sub.2 OCH.sub.3 are storage stable and can be used in oxidative hairdye systems in place of the storage unstable 2-methyl-1-naphthol. Advantageously, it has been found to produce the same colors as 2-methyl-1-naphthol.

Anthraquinone compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are methyl and R.sub.3 is propyl, or R.sub.1 and R.sub.2 are ethyl and R.sub.3 is methyl and A.sup.- is a cosmetically acceptable anion, are useful for the dyeing of hair. Compounds of formula I may advantageously be employed with direct dyes. Compositions and a method of use employing same are disclosed.

Methods for dyeing hair with anthraquinone hair dyes having a quaternary

A method of producing and isolating 5,6-diacetoxyindole (DAI) in a single reaction vessel comprising the following steps:

Method of producing DAI from DOPA, using one reaction vessel

4-Halo-1-naphthol is reacted with a secondary amine and formaldehyde to produce a reaction mixture containing a Mannich base which is hydrogenated to produce 2-methyl-1-naphthol. Advantageously, the procedure can be carried out in one pot.

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Fairfield, CT, United States of America

Linas R Stasaitis