Clairol Incorporated

The Procter Gamble Company

Other

Bristol-Myers Squibb Compnay

Noxell Corporation

James S Anderson

Yuh-Guo Pan

Mu-Ill Lim

Bryan Patrick Murphy

John Michael Gardlik

Guiru Zhang

Garry Steven Garrett

Robert Edward Shumate

Thomas M Schultz

Linas R Stasaitis

Hubert G Lovelady

Mu-III Lim

Michael Y Wong

Robert Edward Schumate

Disclosed is a method of making a 2-substituted-1,4-benzenediamine by nucleophilic aromatic substitution.

Methods of synthesizing 2-substituted-1,4-benzenediamine

Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula (1):where Rand Rare each individually selected from a hydrogen atom, a Cto Calkyl group, a Cto Cmono or dihydroxyalkyl group; phenyl or benzyl optionally substituted with an alkoxy group, or Rand Rtogether with the nitrogen atom to which they are attached form a piperazine, piperidine, imidazole, or morpholine ring.

Couplers for use in oxidative hair dyeing

Coupler for use in oxidative hair dyeing

An anthraquinone mixture comprising three 1,4-hydroxyalkylamino-anthraquinone derivatives, wherein two of the anthraquinone compounds in the mixture are symmetric and the other anthraquinone compound is asymmetric, and wherein each of the anthraquinone compounds has similar polarities. The anthraquinone mixtures are used in compositions and methods for the direct dyeing of keratinous fibers, particularly human hair on the head.

Direct hair dye compositions and methods containing novel anthraquinone

A 2-Substituted-1-naphthol of the formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl or monohydroxy C.sub.1 -C.sub.6 alkyl couples with a primary intermediate of the formula: ##STR2## wherein R is C.sub.1 -C.sub.6 alkyl or monohydroxy C.sub.1 -C.sub.6 alkyl to produce an oxidative dye.

Hair dye compositions containing 3-substituted-4-aminophenols and

The invention provides compositions and methods for the oxidative coloring of human hair. The compositions of the invention contain as a primary dye intermediate a 1-(4-aminophenyl) pyrrolidine, or a cosmetically acceptable salt thereof. The compositions may also contain at least one other primary intermediate and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations. Preferred dye intermediates in the compositions of the invention include 1-(4-aminophenyl) pyrrolidine and 1-(4-amino-3-methylphenyl) pyrrolidine, or cosmetically acceptable salts thereof, which produce intense neutral colors when used in admixture with a suitable coupling agents, such as 3-aminophenol, in conventional hair dye base formulations.

Oxidative hair dye compositions and methods containing

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

Portable anchor for boat docking

The novel hair dye compositions containing a compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be identical or different, are hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl, hydroxyalkoxyalkyl aminoalkyl and dialkylaminoalkyl, each alkyl group and each alkoxy group having from about 1 to about 6 carbons and R.sub.5 is hydrogen or alkyl containing from about 1 to about 6 carbon atoms are disclosed. More specifically, the present invention concerns the inclusion of such compounds of formula I in hair dye compositions as direct dyes, and especially the novel compound 4-(2-hydroxyethylamino)-3-nitrobenzamide. The compounds, some of which are novel, provide a yellow dye base for the hair dyeing compositions.

Compositions containing nitroaniline dyes having a carbamide substituent

4-nitroso anilines and cosmetically acceptable salts thereof are employed as direct dyes. Compositions for dyeing keratin fibers and containing said 4-nitroso anilines and an alkalizing agent are also disclosed.

Nitroso compounds as direct dyes

The novel hair dye compositions containing a compound of the formula: ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be identical or different, are hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl, hydroxyalkoxyalkyl aminoalkyl and dialkylaminoalkyl, each alkyl group and each alkoxy group having from about 1 to about 6 carbons and R.sub.5 is hydrogen or alkyl containing from about 1 to about 6 carbon atoms are disclosed. More specifically, the present invention concerns the inclusion of such compounds of formula I in hair dye compositions as direct dyes, and especially the novel compound 4-(2-hydroxyethylamino)-3-nitrobenzamide. The compounds, some of which are novel, provide a yellow dye base for the hair dyeing compositions.

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Bethel, CT, United States of America

James S Anderson