Indoaniline of the formula ##STR1## wherein R.sub.1 represents hydrogen, halogen, alkyl or alkoxy; R.sub.2 and R.sub.3 represent alkyl; R.sub.4, R.sub.5 and R.sub.6 each independently represent hydrogen, halogen, alkyl, alkoxy, acylamino, ureido or carbalkoxyamino and R.sub.5 can also represent amino, alkylamino, hydroxyalkylamino or carbamylalkylamino, the alkyl and alkoxy groups above being able to contain 1 to 6 carbon atoms and the acyl group from 2 to 7 carbon atoms with the condition that R.sub.5 does not represent hydrogen, chlorine, methyl or methoxy and when R.sub.5 represents acetylamino, R.sub.6 does not represent hydrogen; it being understood that the above compounds can be present in the tautomeric form of that represented by formula (I). The indoaniline is usefully employed in dye compositions for keratinic fibers, especially living human hair.

The present invention relates to dialkylamine indoanilines of the formula 
##STR2## 
wherein R.sub.1 represents hydrogen, halogen, alkyl or alkoxy; R.sub.2 and 
R.sub.3 represent alkyl, R.sub.4, R.sub.5 and R.sub.6 each independently 
represents hydrogen, halogen, alkyl, alkoxy, acylamino, ureido or 
carbalkoxy amino, R.sub.5 can also represent amino, alkylamino, 
hydroxyalkylamino or carbamylalkylamino, with the proviso that R.sub.5 
cannot represent hydrogen, chlorine, methyl or methoxy and when R.sub.5 
represents acetylamino, R.sub.6 does not represent hydrogen (the above 
alkyl and alkoxy groups can contain from 1 to 6 carbon atoms and the acyl 
group can obtain from 2 to 7 carbom atoms). The present invention also 
relates to a process for preparing these compounds and to the preparation 
of dye compositions for keratinic fibers and in particular for living 
human hair containing said compounds. It will be appreciated that the 
above compounds can be present under tautomeric forms of that which is 
represented by formula (I). 
Among the tautomer forms possible, one can cite the formula 
##STR3## 
and when R.sub.5 designates an amino, alkylamino, hydroxyalkylamino, or 
carbamylalkylamino, the formula 
##STR4## 
wherein R.sub.1 to R.sub.6 have the meanings given above and R represents 
hydrogen, alkyl, hydroxyalkyl, or carbamylalkyl. 
The compounds of formula (I) can be prepared by condensing a compound of 
the formula 
##STR5## 
wherein Z represents NH.sub.2, or NO when R.sub.1 is in meta position 
relative to the -NR.sub.2 R.sub.3 group, on a phenolic compound of the 
formula 
##STR6## 
wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 have the 
meanings given above, or the meanings given on page 7. 
In a first method of preparation, when Z represents NH.sub.2, one condenses 
the phenolic compound of formula (III) on a paraphenylenediamine of the 
formula 
##STR7## 
wherein R.sub.1, R.sub.2 and R.sub.3 have the meanings given above in an 
aqueous alkaline medium, in a hydroalcoholic medium, preferably 
hydroethanolic or hydroisopropanolic or in a hydroacetonic medium having a 
pH greater than 8 in the presence of an oxidizing agent and at a 
temperature of about 0.degree. C. 
The ratio of the phenolic compound to the paraphenylenediamine is between 
about 1:1 and 1:2, this ratio generally being about 1:1. 
The oxidizing agent usefully employed in this condensation reaction can be, 
for example, H.sub.2 O.sub.2, an alkaline persulfate, for example, the 
persulfate of potassium or ammonium, an alkaline ferricyanide, for example 
potassium ferricyanide. The quantity of the oxidizing agent employed can 
vary from 1-5 times preferably 1-3 times the stoichiometric amount 
required for oxidizing the p-phenylenediamine to a quinone diimine. 
As phenols, one can use 2-methyl-5-ureido phenol, 2-methyl-5-acetylamino 
phenol, 2-methyl-5-amino phenol, 2-methyl-5-methylamino phenol, 3-ureido 
phenol, 2,6-dimethyl-5-acetylamino phenol, 2,6-dimethyl-3-amino phenol, 
2,6-xylenol, 2-acetylamino phenol, meta-aminophenol, 2,6-dimethyl-3-ureido 
phenol, 3-methoxy phenol, 3-acetylamino phenol, 
2-methyl-5-carbamylmethylaminophenol, 2,6-dimethylphenol, 
2-methyl-5-carbethoxyamino phenol, 2,6-dimethyl-5-amino phenol, 
2-methyl-5-(N-.beta.-hydroxyethylamino) phenol, 2,5-dimethyl phenol, 
2,3-xylenol, 2-ureido phenol, 2-chloro-5-amino phenol, 
2-chloro-5-acetylamino phenol and 3-chloro-6-acetylamino phenol. 
As the paraphenylenediamines one can use, for instance, N,N-dimethyl 
paraphenylenediamine, 2-methyl-4,-N,N-diethylamino aniline, 
4-N,N-diethylamino-2-chloroaniline, 3-methoxy-4-amino-N,N-dimethyl 
aniline, 3-chloro-4-amino-N,N-dimethyl aniline, 3-methyl-4-amino-dimethyl 
aniline, N,N-diethyl-p-phenylenediamine, 
4-N,N-diethylamino-3-chloroaniline, 4-N,N-dimethylamino-3-chloroaniline 
and N,N-dibutyl-p-phenylenediamine. 
The paraphenylenediamines can be replaced by one of their salts and in 
particular by the hydrochloride, hydrobromide, sulfate or phosphate 
thereof. 
In a second method of the present invention, when Z represents NO, one 
condenses the phenolic compound of formula (III) on a nitroso derivative 
of formula (V) 
##STR8## 
wherein R.sub.1, R.sub.2 and R.sub.3 have the meanings given above. This 
condensation reaction is effected in an aqueous or hydroalcoholic medium 
preferably a hydroethanolic or a hydroispropanolic medium at a temperature 
between about 30.degree. and 60.degree. C., and preferably between 
40.degree. and 55.degree. C. 
Representative nitroso compounds that can usefully be employed include, 
4-nitroso-N,N-dibutylaniline, 3-chloro-4-nitroso diethylaniline and 
3-methoxy-4-nitroso-N,N-dimethylaniline. 
The compounds wherein R.sub.1 is in a position ortho relative to the 
--NR.sub.2 R.sub.3 group and R.sub.5 is amino can be obtained by 
hydrolysis using a base such as NaOH on the corresponding 3-acetylated 
derivative. 
The indoanilines of formula (I), wherein R.sub.1 represents hydrogen, 
halogen, alkyl or alkoxy; R.sub.2 and R.sub.3 represent alkyl; R.sub.4, 
R.sub.5 and R.sub.6 each independently represents hydrogen, halogen, 
alkyl, alkoxy, acylamino, ureido, or carbalkoxyamino and R.sub.5 can also 
designate amino, alkylamino, hydroxyalkylamino or carbamylalkylamino (the 
above alkyl groups being able to contain 1 to 6 carbon atoms) with the 
proviso that R.sub.5 does not represent hydrogen, chlorine, methoxy or 
methyl and when R.sub.5 represents acetylamino, R.sub.6 does not represent 
hydrogen, are new compounds. 
Additionally, the following are new compounds: 
N-[(4'-diethylamino-2'-methyl)phenyl]-2,6-dimethyl benzoquinoneimine, 
N-[(4'-diethylamino-2'-chloro)phenyl]-2-acetamino benzoquinoneimine, 
N-[(4'-dimethylamino-2'-methyl)phenyl]-2,6-dimethyl benzoquinoneimine, 
N-[(4'-dimethylamino-2'-chloro)phenyl]-2,6-dimethyl benzoquinoneimine, 
N-[(4'-dimethylamino-2'-methoxy)phenyl]-2,6-dimethyl benzoquinoneimine, and 
N-[(4'-dimethylamino-3'-chloro)phenyl]-2,6-dimethylbenzoquinoneimine. 
The present invention also has for an object the dyes obtained by the 
condensation of a compound of formula (II) on a compound of formula (III), 
as well as dyes obtained by the hydrolysis of a compound acetylated in 
position 3 in the corresponding aminated dye. 
The dyes find an interesting application in the dyeing of keratinic fibers 
and in particular of living human hair. 
The present invention also has for an object a dye composition for 
keratinic fibers, in particular for living human hair, characterized by 
the fact that they include in an aqueous or hydroalcoholic solution, at 
least one compound of formula (I) 
##STR9## 
wherein R.sub.1 represents hydrogen, halogen, alkyl or alkoxy; R.sub.2 and 
R.sub.3 each independently represents alkyl; R.sub.4, R.sub.5 and R.sub.6 
each independently represent hydrogen, halogen, alkyl, alkoxy, acylamino, 
ureido, or carbalkoxyamino and R.sub.5 can also represent amino, 
alkylamino, hydroxyalkylamino or carbamylalkylamino; it being understood 
that the alkyl groups can contain from 1 to 6 carbon atoms and the acyl 
groups can contain from 2 to 7 carbon atoms. 
These dye compositions include from 0.0075 to 2% and preferably from 0.02 
to 0.5% of the compound of formula (I) of the total weight of the 
composition. 
The dye compositions according to the present invention can include only 
the indoanilines of formula (I). 
It is, however, possible to mix the dyes according to the invention with 
other dyes conventionally utilized for the dyeing of hair, for example 
nitro benzene dyes, azo dyes, anthraquinone dyes, indamines, indophenols 
and/or other indoanilines. 
The compositions according to the present invention are generally present 
in the form of an aqueous or hydroalcoholic solution containing one or 
more compounds of formula (I), in mixture or not with other dyes. They 
can, however, also include thickening agents and be present in the form of 
creams or gels. 
To illustrate thickening agents that can be incorporated in the dye 
compositions of the present invention, one can mention cellulose 
derivatives such a methylcellulose, hydroxyethylcellulose, 
carboxymethylcellulose or acrylic polymers such as the sodium salt of 
polyacrylic acid or carboxyvinyl polymers. 
The dye compositions can include as solvents, water, lower alkanols, such 
as ethanol or isopropanol, polyalcohols such as glycols, for example, 
ethyleneglycol, propyleneglycol, butylglycol, diethyleneglycol and the 
monomethylether of diethyleneglycol. 
The compositions according to the invention can also include various 
components conventionally utilized in cosmetic preparations, such as 
wetting agents, for example, oxyethylenated alkyl phenols, oxyethylenated 
fatty acids, oxyethylenated fatty alcohols, the sulfates and sulfonates of 
fatty alcohols optionally oxyethylenated, dispersing agents, swelling 
agents, penetrating agents, emollients, polymers and/or perfumes. They can 
also be packaged in aerosol containers under pressure in the presence of a 
gaseous propellent. 
One can use as the gaseous propellent, nitrogen, nitrous oxide, volatile 
hydrocarbons such as butane, isobutane, propane or preferably the 
fluoronated hydrocarbons sold under the name of FREON by Dupont, such a 
dichlorodifluoromethane, 1,1-difluoromethane, 
1,2-dichloro-(1,1,2,2-tetrafluoromethane) or 1-chloro-1,1-difluoromethane; 
a mixture of two or more hydrocarbons or fluoronated hydrocarbons can also 
be utilized. 
The pH of the compositions can vary to a large extent. It is generally 
between about 4 to 11 and preferably between 6.5 and 10.5 and 
advantageously between 7 and 9. 
One can adjust the pH of the composition with an alkalizing agent for 
example, ammonia, mono-, di- or triethanolamine, trisodium or disodium 
phosphate, sodium or potassium carbonate or with an acidifying agent for 
example, acetic acid, lactic acid, phosphoric acid, or citric acid. 
The dyeing of keratinic fibers, in particular, living human hair, with the 
dye compositions according to the present invention can be effected in a 
conventional manner by applying the composition to the fibers to be dyed, 
permitting said composition to remain in contact therewith for a period 
varying from 5 to 30 minutes, followed by rinsing and eventually washing 
and drying the fibers. 
The compositions according to the invention, when present in the form of a 
hydroalcoholic solution, can also include a cosmetic film-forming resin 
and thus constitute a colored hair setting lotion which can be applied to 
wet hair before the hair is set. 
Representative cosmetic resins that can be employed in these hair setting 
lotion compositions include polyvinyl pyrrolidone; copolymers of 
polyvinylpyrrolidone and vinyl acetate; copolymers of vinyl acetate and an 
unsaturated carboxylic acid, such as crotonic acid; copolymers resulting 
from the copolymerization of vinyl acetate, crotonic acid and an acrylic 
or methacrylic ester; copolymers resulting from the copolymerization of 
vinyl acetate and a vinyl alkyl ether; copolymers resulting from the 
copolymerization of vinyl acetate, crotonic acid and a vinyl ester of a 
long carbon chain acid or an acrylic or methacrylic ester of a long carbon 
chain acid; copolymers resulting from the copolymerization of an ester 
derived from an unsaturated alcohol and short carbon chain acid, from an 
unsaturated acid having a short carbon chain, and from at least one ester 
derived from an unsaturated short chain alcohol and an unsaturated acid; 
and copolymers resulting from the copolymerization of at least one 
unsaturated ester and at least one unsaturated acid. 
Representative preferred resins include polyvinylpyrrolidone having a 
molecular weight from 10,000 to 160,000; copolymers of 10% crotonic acid 
and 90% vinyl acetate having a molecular weight from 10,000 to 70,000; 
copolymers of polyvinylpyrrolidone (PVP) and vinyl acetate (VA) having a 
molecular weight of 30,000 to 200,000, the ratio of PVP to VA being 
between about 30:70 and 70:30; copolymers of maleic anhydride and 
methylvinyl ether having a molar ratio of 1:1 and a specific viscosity, 
measured at 25.degree. C. at a concentration of 1 gram in 100 cc of 
methylethyl ketone, between 0.1 and 3.5; the monoethyl ester, 
monoisopropyl ester and monobutyl ester of these copolymers of maleic 
anhydride and methylvinyl ether; the copolymer of maleic anhydride and of 
butylvinyl ether having a mole ratio of 1:1; the terpolymers of 
methylmethacrylate (15 to 25%) - stearylmethacrylate (18 to 28%) and 
dimethylmethacrylate (52 to 62%); and the terpolymers of vinyl acetate (75 
to 85%) - allylstearate (10 to 20%) and allyloxyacetic acid (3 to 10%). 
These resins are used generally in amounts between about 1 to 3% by weight 
of the total composition. 
The alcohols employed to produce the hair setting lotions according to the 
present invention are low molcular weight alcohols and preferably are 
ethanol or isopropanol. These alcohols are generally used in amounts of 
about 20 to 70% by weight of the total composition. 
The hair setting lotions according to the present invention can be employed 
in a conventional manner by applying the same to living human hair 
previously washed and rinsed, followed by rolling the same on rollers and 
then drying the hair. 
The invention is illustrated by the following examples:

EXAMPLE I 
Preparation of N-[(4'-dimethylamino)phenyl]-2-methyl-5-ureido 
benzoquinoneimine. 
##STR10## 
0.1 mole (16.6 grams) of 2-methyl-5-ureido phenol is dissolved in 400 cc of 
isopropyl alcohol to which have been added 400 cc of ammonia at 22.degree. 
Be. To this solution, there is added 0.1 mole (20.9 grams) of the 
dihydrochloride of N,N-dimethyl paraphenylenediamine in 650 cc of water. 
After adding to this mixture 800 g of crushed ice, there is introduced, 
little by little, with good agitation and while maintaining the 
temperature near 0.degree. C., 0.2 mole (45.6 g) of ammonium persulfate in 
150 cc of water. At the end of this addition, the above indoaniline which 
has precipitated is filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 275.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.18 N.sub.4 O.sub.2 
Found 
______________________________________ 
C% 64.41 64.29 64.44 
H% 6.37 6.31 6.26 
N% 18.78 19.01 18.93 
______________________________________ 
EXAMPLE II 
Preparation of N-[(4'-dimethylamino)phenyl]-2-methyl-5-acetylamino 
benzoquinoneimine. 
##STR11## 
0.16 mole (26.4 g) of 2-methyl-5-acetylamino phenol is dissolved in 700 cc 
of isopropanol to which have been added 800 cc of ammonia at 22.degree. 
Be. To this solution, there is added 0.176 mole (36.8 g) of the 
dihydrochloride of N,N-dimethylparaphenylenediamine in 100 cc of water and 
1.3 kg of crushed ice. There is then added to the resulting mixture, whose 
temperature is maintained at about 0.degree. C. little by little, and with 
agitation, 0.352 moles (80.25 g) of ammonium persulfate in 200 cc of 
water. At the end of this addition the above indoaniline which has 
precipitated is filtered, washed with water and recrystallized in a 
mixture of dimethylformamide and water. The above product exhibits a 
melting point of 180.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.19 O.sub.2 N.sub.3 
Found 
______________________________________ 
C% 68.72 68.59 
H% 6.39 6.59 
N% 14.14 13.96 
______________________________________ 
EXAMPLE III 
Preparation of N-[(4'-dimethylamino)phenyl]-2-methyl-5-amino 
benzoquinoneimine. 
##STR12## 
0.2 mole (24.6 g) of 2-methyl-5-amino phenol is dissolved in 500 cc of 
acetone to which have been added 200 cc of water and 500 cc of ammonia at 
22.degree.Be. There are then added 500 g of crushed ice. Little by little 
and with agitation, there are introduced into this reaction mixture, 
maintained at about 5.degree. C. simultaneously with the aid of a double 
funnel, 0.2 mole (41.8 g) of the dihydrochloride of N,N-dimethyl 
paraphenylenediamine in 320 cc of water and 0.2 mole (45.8 g) of ammonium 
persulfate in 200 cc of water. At the end of this addition, the above 
indoaniline, which has precipitated, is filtered, washed with water, 
recrystallized in a mixture of dimethylformamide and water and dried under 
a vacuum. It exhibits a melting point of 255.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.15 H.sub.17 ON.sub.3 
Found 
______________________________________ 
C% 70.58 70.45 
H% 6.66 6.82 
N% 16.47 16.34 
______________________________________ 
EXAMPLE IV 
Preparation of N-[(4'-dimethylamino)phenyl]-2-methyl-5-methylamino 
benzoquinoneimine. 
##STR13## 
0.025 mole (3.42 g) of 2-methyl-5-methylamino phenol is dissolved in 100 cc 
of water to which have been added 100 cc of ammonia at 22.degree.Be. 150 g 
of crushed ice are then added to this solution. The resulting reaction 
mixture is maintained at a temperature of about 5.degree. C. There are 
then introduced simultaneously, with good agitation and with the aid of a 
double funnel, 0.025 mole (5.23 g) of the dihydrochloride of N,N-dimethyl 
paraphenylenediamine in 50 cc of water and 0.025 mole (5.7 g) of ammonium 
persulfate in 50 cc of water. The above indoaniline which has precipitated 
is then filtered, washed with water and recrystallized in a mixture of 
dimethylformamide and water. After drying under a vacuum, it exhibits a 
melting point of 202.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.19 N.sub.3 O 
Found 
______________________________________ 
C% 71.34 71.23 71.19 
H% 7.11 7.01 7.01 
N% 15.60 15.61 15.73 
______________________________________ 
EXAMPLE V 
Preparation of N-[(4'-dimethylamino)phenyl]-3-ureido benzoquinoneimine. 
##STR14## 
0.03 mole (4.56 g) of 3-ureido phenol is dissolved in 100 cc of isopropyl 
alcohol to which have been added 100 cc of ammonia at 22.degree.Be. 350 g 
of crushed ice are then added to this solution. The resulting reaction 
mixture is maintained at about 0.degree. C., and there are introduced 
simultaneously, with good agitation and with the aid of a double funnel, 
0.03 mole (6.27 g) of the dihydrochloride of N,N-dimethyl 
paraphenylenediamine in 50 cc of water and 0.060 mole (13.7 g) of ammonium 
persulfate in 50 cc of water. At the end of this addition, the agitation 
is continued for 15 minutes and the above indoaniline is continued for 15 
minutes and the above indoaniline which has precipitated is then filtered, 
washed with water, recrystallized in a mixture of dimethylformamide in 
water and dried under a vacuum. It exhibits a melting point of 226.degree. 
C. 
______________________________________ 
Calculated For 
Analysis C.sub.15 H.sub.16 N.sub.4 O.sub.2 
Found 
______________________________________ 
C% 63.36 63.45 63.52 
H% 5.67 5.77 5.83 
N% 19.71 19.88 19.72 
______________________________________ 
EXAMPLE VI 
Preparation of N-[(4'-dimethylamino) phenyl]-2,6-dimethyl-3-acetylamino 
benzoquinoneimine. 
##STR15## 
0.3 mole (53.7 g) of 2,6-dimethyl-3-acetylamino phenol is dissolved in 400 
cc of acetone to which have been added 400 cc of ammonia at 22.degree.Be. 
The resulting mixture is maintained at a temperature of about 10.degree. 
C., and there are introduced therein simultaneously, with the aid of a 
double funnel, 0.3 mole (62.7 g) of the dihydrochloride of N,N-dimethyl 
paraphenylenediamine in 500 cc of water and 0.6 mole (137 g) of ammonium 
persulfate in 500 cc of water. The above indoaniline which precipitates is 
then filtered, washed with water, recrystallized in a mixture of 
dimethylformamide and water and dried under a vacuum. It exhibits a 
melting point of 111.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.21 O.sub.2 N.sub.3 
Found 
______________________________________ 
C% 69.43 69.13 69.25 
H% 6.80 6.64 6.74 
N% 13.50 13.72 13.60 
______________________________________ 
EXAMPLE VII 
Preparation of N-[(4'-dimethylamino) phenyl]-2,6-dimethyl-3-amino 
benzoquinoneimine. 
##STR16## 
0.4 mole (69.4 g) of 2,6-dimethyl-3-amino phenol is dissolved in 1 liter of 
acetone to which has been added 1 liter of ammonia at 22.degree.Be. 1 kg 
of crushed ice is then added to this solution and then with the aid of a 
double funnel, there are introduced simultaneously, with good agitation, 
0.4 mole (83.6 g) of the dihydrochloride of 
N,N-dimethylparaphenylenediamine in 1 liter of water and 0.44 mole (100 g) 
of ammonium persulfate in 800 cc of water. The temperature of the reaction 
mixture is maintained at about 0.degree. C. At the end of the addition, 
the raw product is filtered, washed with water and recrystallized in a 
mixture of dimethylformamide and water. After drying under a vacuum, the 
above indoaniline exhibits a melting point of 178.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.19 ON.sub.3 
Found 
______________________________________ 
C% 71.34 71.41 71.57 
H% 7.11 7.19 7.26 
N% 15.60 15.45 15.57 
______________________________________ 
EXAMPLE VIII 
Preparation of N-[(4'-diethylamino-2'-methyl) phenyl]-2,6-dimethyl 
benzoquinoneimine. 
##STR17## 
0.01 mole (2.51 g) of the dihydrochloride of 2-methyl-4-N,N-diethylamino 
aniline and 0.01 mole (1.22 g) of 2,6-xylenol are dissolved in 85 cc of 
normal sodium hydroxide solution to which have been added 20 cc of 
ethanol. Little by little, to this solution, with agiytation and while 
maintaining the temperature near about 0.degree. C., there is added 0.02 
mole (4.56 g) of ammonium persulfate in 46 cc of water. The raw 
indoaniline above is filtered, washed with water and recrystallized in a 
mixture of water and acetone. After drying under a vacuum, the product 
exhibits a melting point of 128.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.19 H.sub.24 N.sub.2 O 
Found 
______________________________________ 
C% 76.99 76.83 76.76 
H% 8.16 8.05 8.19 
N% 9.45 9.32 9.54 
______________________________________ 
EXAMPLE IX 
Preparation of N-[4'-diethylamino-2'-chloro) phenyl]-2-acetamino 
benzoquinoneimine. 
##STR18## 
0.01 mole (1.51 g) of 2-acetylamino phenol is dissolved in 25 cc of 
isopropyl alcohol to which have been added 25 cc of ammonia at 22 Be. 
There are then added 50 g of crushed ice. The resulting mixture is 
maintained at a temperature of about 0.degree. C., and there are then 
introduced simultaneously with agitiation, 0.01, mole (2.71 g) of the 
dihydrochloride of 2-chloro-4-N,N-diethylamino aniline in 20 cc of water 
and 0.02 mole (4.46 g) of ammonium persulfate in 25 cc of water. At the 
end of this addition, the above indoaniline which precipitates is 
filtered, washed with water, recrystallized in dimethylformamide, and 
dried under a vacuum. The product exhibits a melting point of 155.degree. 
C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.20 N.sub.3 ClO.sub.2 
Found 
______________________________________ 
C% 62.51 62.76 62.75 
H% 5.80 5.95 5.95 
N% 12.18 12.16 12.32 
______________________________________ 
EXAMPLE X 
Preparation of N-[(4'-dimethylamino) phenyl]-3-amino benzoquinoneimine. 
##STR19## 
0.01 mole (2.09 g) of the dihydrochloride of 
N,N-diemthylparaphenylenediamine and, 0.01 mole (1.09 g) of 
metaaminophenol are dissolved in 40 cc of water to which have been added 7 
cc of ammonia at 22.degree.Be. To this solution, cooled to 0.degree. C., 
there are added 20 cc of H.sub.2 O.sub.2 (20 volumes). The resulting 
reaction mixture is left to stand for 24 hours at ambient temperature. The 
raw product which has precipitated is then filtered, washed with water and 
dried under a vacuum. This raw product is then extracted 4 times with 100 
cc of ether, at 20.degree. C. The etherified extracts are then combined 
and concentrated under a vacuum to a volume of about 10 cc. After cooling, 
the above indoaniline which has crystallized is filtered, recrystallized 
in dimethylformamide and dried under a vacuum. The product exhibits a 
melting point of 171.degree. C., and is chromatographically pure. 
Molecular mass calculated for C.sub.14 H.sub.15 N.sub.3 O:241. Molecular 
mass found by potentiometric dosage effected in methylisobutylketone with 
perchloric acid:240. 
______________________________________ 
Calculated For 
Analysis C.sub.14 H.sub.15 N.sub.3 O 
Found 
______________________________________ 
C% 69.69 69.58 69.46 
H% 6.27 6.26 6.27 
N% 17.42 17.70 17.64 
______________________________________ 
EXAMPLE XI 
Preparation of N-[(4'-dimethylamino) phenyl]-2,6-diemthyl-5-ureido 
benzoquinoneimine. 
##STR20## 
0.2 mole (36 g) of 2,6-dimethyl-3-ureido phenol is dissolved in 1 liter of 
isopropyl alcohol to which have been added 800 cc of ammonia at 
22.degree.Be. There are then added 800 g of crushed ice to this reaction 
mixture. Then, little by little and with good agitation, there are 
introduced simultaneously, 0.2 mole (41 g) of the dihydrochloride of 
N,N-dimethylparaphenylenediamine in 500 cc of water and 0.4mole (92 g) of 
ammonium persulfate in 500 cc of water. During the time of these 
additions, the temperature of the reaction mixture is maintained at about 
0.degree. C. At the end of these additions, the above indoaniline is 
filtered, washed with water and dried under a vacuum. The product is 
chromatographically pure and melts at a temperature of 245.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.20 N.sub.4 O.sub.2 
Found 
______________________________________ 
C% 65.36 65.60 65.61 
H% 6.45 6.55 6.57 
N% 17.94 18.08 17.97 
______________________________________ 
EXAMPLE XII 
Preparation of N-[(4'-dibutylamino) phenyl]-2-methyl-5-carbamylmethylamino 
benzoquinoneimine. 
##STR21## 
0.01 mole (2.7 g) of the hydrochloride of 4-nitroso-N,N-dibutylaniline and 
0.01 mole (1.80 g) of 2-methyl-5-carbamylmethylamino phenol are dissolved 
in 30 cc of a 50% hydroethanolic solution. The resulting reaction mixture 
is stirred for a period of 1 hour at 40.degree. C. The above raw 
indoaniline which has precipitated is then filtered and dissolved in 10 cc 
of dimethylformamide at ambient temperature. After filtration, in order to 
eliminate secondary insoluble products formed in a minor quantity, there 
are added 10 ml of water to reprecipitate the indoaniline which is then 
filtered, washed with water and dried under a vacuum. The product is 
chromatographically pure and melts at 169.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.23 H.sub.32 N.sub.4 O.sub.2 
Found 
______________________________________ 
C% 69.66 69.80 69.68 
H% 8.13 8.23 8.26 
N% 14.13 14.04 13.98 
______________________________________ 
EXAMPLE XIII 
Preparation of N-[(4'-diethylamino-2'-chloro)phenyl]-2,6-dimethyl-3-amino 
benzoquinoneimine. 
##STR22## 
Into 30 cc of ethanol to which have been added 20 cc of a normal sodium 
hydroxide solution, there are introduced 0.01 mole (2.12 g) of 
3-chloro-4-nitroso diethylaniline and 0.011 mole (1.91 g) of the 
hydrochloride of 2,6-dimethyl-3-amino phenol. The mixture is maintained 
with agitation for 4 hours at 35.degree. C. The above indoaniline is then 
filtered, washed several times with water at 50.degree. C., and 
recrystallized in a mixture of dimethylformamide in water. The product 
exhibits a melting point of 160.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.22 N.sub.3 ClO 
Found 
______________________________________ 
C% 65.15 65.04 65.14 
H% 6.65 6.72 6.74 
N% 12.67 12.73 12.69 
Cl% 10.70 10.84 10.92 
______________________________________ 
EXAMPLE XIV 
Preparation of N-[(4'-dimethylamino) phenyl]-2-chloro-5-amino 
benzoquinoneimine. 
##STR23## 
0.01 mole (2.09 g) of the dihydrochloride of 
N,N-dimethylparaphenylenediamine and 0.01 mole (1.43 g) of 
2-chloro-5-amino phenol are dissolved in 150 cc of a 0.7 N sodium 
hydroxide solution. To this solution, cooled to 0.degree. C., there is 
added, little by little, with agitation, 0.02 mole (4.60 g) of ammonium 
persulfate in solution in 20 cc of water. At the end of this addition, the 
agitation of the mixture is continued for an additional 15 minutes. The 
above indoaniline which precipitates is filtered, washed with water and 
then with acetone. The raw product is dissolved in dimethylformamide at 
0.degree. C., (10 cc of dimethylformamide per gram of raw product). The 
resulting solution is then filtered to eliminate a slightly insoluble 
white product. After cooling the filtrate to 0.degree. C., the above 
indoaniline crystallizes in the form of reddish-brown flakes having golden 
glints. These flakes are filtered and dried under a vacuum. After drying, 
the product exhibits a melting point of 242.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.14 H.sub.14 N.sub.3 ClO 
Found 
______________________________________ 
C% 60.98 61.09 60.92 
H% 5.09 5.00 4.96 
N% 15.24 15.40 15.21 
Cl% 12.87 12.93 13.02 
______________________________________ 
EXAMPLE XV 
Preparation of N-[(4'-dimethylamino-2'-methyl)phenyl]-2,6-dimethyl 
benzoquinoneimine. 
##STR24## 
0.01 mole (1.22 g) of 2,6dimethyl phenol is dissolved in 20 cc of acetone, 
5 cc of water and 15 cc of ammonia (22.degree.Be). To this solution, 
maintained at a temperature of about +5.degree. C., there are added, 
little by little, with agitation, and simultaneously with the aid of a 
double funnel, 0.01 mole (2.23 g) of the dihydrochloride of 
3-methyl-4-amino-N,N-dimethylaniline dissolved in 15 cc of water and 0.02 
mole (4.6 g) of ammonium persulfate dissolved in 20 cc of water. At the 
end of these additions, the stirring of the reaction mixture is continued 
for one hour at ambient temperature. The above indoaniline which has 
precipitated is then filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 157.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.20 N.sub.2 O 
Found 
______________________________________ 
C% 76.08 75.95 
H% 7.51 7.51 
N% 10.44 10.46 
______________________________________ 
EXAMPLE XVI 
Preparation of N-[(4'-dimethylamino-2'-chloro)phenyl]-2,6-dimethyl 
benzoquinoneimine. 
##STR25## 
0.01 mole (1.22 g) of 2,6-dimethyl phenol and 0.01 mole (2.44 g) of the 
dihydrochloride of 3-chloro-4-amino-N,N-dimethylaniline are dissolved in 
20 cc of acetone, 15 cc of water and 15 cc of ammonia (22.degree.Be). To 
this resulting solution, cooled to about +5.degree. C., there is added, 
little by little, with agitiation, 0.02 mole of ammonium persulate 
dissolved in 20 cc of water. At the end of this addition, the stirring is 
continued for 30 minutes. The above indoaniline which has precipitated is 
filtered, washed with water and dried under a vacuum. It exhibits a 
melting point of 154.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.17 ClN.sub.2 O 
Found 
______________________________________ 
C% 66.19 66.04 
H% 5.58 5.80 
N% 9.70 9.74 
Cl% 12.27 12.14 
______________________________________ 
EXAMPLE XVII 
Preparation of N-[(4'-dimethylamino-2'-methoxy) pehnyl]-2,6-dimethyl 
benzoquinoneimine. 
##STR26## 
0.01 mole (2.64 g) of 3-methoxy-4-amino-N,N-dimethylaniline sulfate and 
0.01 mole (1.22 g) of 2,6-dimethyl phenol are dissolved in 20 cc of water, 
35 cc of acetone and 10 cc of ammonia (22.degree.Be). To the resulting 
solution, cooled in ice, there is added, little by little, with agitation, 
0.02 mole (4.6 g) of ammonium persulfate in 20 cc of water. At the end of 
this addition the stirring of the rection mixture is continued for one 
hour. The above indoaniline which has precipitated is then filtered, 
washed first with water and then with acetone and dried under a vacuum. It 
exhibits a melting point of 140.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.20 N.sub.2 O.sub.2 
Found 
______________________________________ 
C% 71.80 71.60 
H% 7.09 7.06 
N% 9.85 9.99 
______________________________________ 
EXAMPLE XVIII 
Preparation of N-[(4'-dimethylamino-2'-methyl) phenyl]-6-methyl-3-amino 
benzoquinoneimine. 
##STR27## 
0.02 mole (2.46 g) of 2-methyl-5-amino phenol is dissolved in 40 cc of 
acetone, 10 cc of ice and 30 cc of ammonia (22.degree. Be). To the 
resulting solution, maintained at a temperature of about +5.degree. C., 
there are added, little by little, with agitation and simultaneously with 
the aid of a double funnel, 0.02 mole (4.46 g) of the dihydrochloride of 
3-methyl-4-amino-N,N-dimethylaniline dissolved in 25 cc of water and 0.02 
mole (4.6 g) of ammonium persulfate dissolved in 10 cc of water. At the 
end of this addition, the stirring of the reaction mixture is combined for 
one hour at ambient temperature. The above indoaniline which has 
precipitated is then filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 200.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.19 N.sub.3 O 
Found 
______________________________________ 
C% 71.34 71.41 
H% 7.11 7.37 
N% 15.60 15.79 
______________________________________ 
EXAMPLE XIX 
Preparation of N-[(4'-dimethylamino-2'-methoxy-)phenyl]-6-methyl-3-amino 
benzoquinoneimine. 
##STR28## 
0.012 mole (3.2 g) of 3-methoxy-4-amino-N,N-dimethylaniline sulfate and 
0.02 mole (2.46 g) of 2-methyl-5-amino phenol are dissolved in 60 cc of a 
50% hydroacetonic solution to which have been added 20 cc of ammonia 
(22.degree. Be). To the resulting solution, maintained at a temperature of 
about 0.degree. C., there is added, little by little, with agitation, 0.02 
mole (4.6 g) of ammonium persulfate dissolved in 20 cc of water. At the 
end of this addition, stirring of the reaction mixture is continued for 
one hour at 0.degree. C. The above indoaniline which has precipitated is 
then filtered, washed first with water and then with a normal NaOH 
solution to eliminate the 2-methyl-5-amino phenol that it contains, and 
finally with water. After recrystallization in a mixture of 
dimethylformamide and water and drying under a vacuum, the product 
exhibits a melting point of 168.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.19 N.sub.3 O.sub.2 
Found 
______________________________________ 
C% 67.34 67.32 
H% 6.71 6.77 
N% 14.73 14.58 
______________________________________ 
EXAMPLE XX 
Preparation of N-[(4'-dimethylamino-2'-chloro) 
phenyl]-6-methyl-3-acetylamino benzo-quinoneimine. 
##STR29## 
0.01 mole (1.65 g) of 2-methyl-5-acetylamino phenol and 0.01 mole (2.44 g) 
of the dihydrochloride of 3-chloro-4-amino-N,N-dimethylaniline are 
dissolved in 20 cc of acetone to which have been added 15 cc of water and 
15 cc of ammonia (22.degree. Be). To the resulting solution, maintained at 
a temperature of about +5.degree. C., there is added, little by little, 
with agitation, 0.02 mole (4.6 g) of ammonium persulfate in 20 cc of 
water. At the end of this addition, the stirring of the reaction mixture 
is continued for 30 minutes. The above indoaniline which precipitates is 
then filtered, washed with water, recrystallized in a mixture of 
dimethylformamide and water and dried under a vacuum. It exhibits a 
melting point of 178.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.18 ClN.sub.3 O.sub.2 
Found 
______________________________________ 
C% 61.53 61.30 
H% 5.46 5.15 
N% 12.66 12.38 
Cl% 10.68 10.43 
______________________________________ 
EXAMPLE XXI 
Preparation of N-[(4'-dimethylamino-2'-chloro) phenyl]-6-methyl-3-amino 
benzoquinoneimine. 
##STR30## 
0.01 mole (1.23 g) of 2-methyl-5-amino phenol is dissolved in 10 cc of 
acetone to which have been added 5 cc of water and 15 cc of ammonia 
(22.degree. Be). To the resulting solution, cooled to about +5.degree. C., 
there are added, little by little, with agitation and simultaneously with 
the use of a double funnel, 0.01 mole (2.44 g) of the dihydrochloride of 
3-chloro-4-amino-N,N-dimethylaniline dissolved in 15 cc of water, and 0.01 
mole (2.3 g) of ammonium persulfate dissolved in 10 cc of water. At the 
end of this addition, the stirring of the reaction mixture is continued 
for 30 minutes. The above indoaniline which has precipitated in the form 
of crystals is then filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 203.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.15 H.sub.16 ClN.sub.3 O 
Found 
______________________________________ 
C% 62.16 62.33 
H% 5.56 5.42 
N% 14.50 14.40 
Cl% 12.23 12.32 
______________________________________ 
EXAMPLE XXII 
Preparation of N-[(4'-dimethylamino-2'-methyl) 
phenyl]-6-methyl-3-acetylamino benzoquinoneimine. 
##STR31## 
0.01 mole (1.65 g) of 2-methyl-5-acetylamino phenol is dissolved in 20 cc 
of acetone, 5 cc of water and 15 cc of ammonia (22.degree. Be). To the 
resulting solution, maintained at a temperature of about +5.degree. C., 
there are added, little by little, with agitation and simultaneously with 
the aid of a double funnel, 0.01 mole (2.23 g) of the dihydrochloride of 
3-methyl-4-amino-N,N-dimethyl aniline dissolved in 15 cc of water, and 
0.02 mole (4.6 g) of ammonium persulfate dissolved in 20 cc of water. At 
the end of this addition, the stirring of the reaction mixture is 
continued for one hour. The above indoaniline which has precipitated in 
the form of crystals, is filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 182.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.21 N.sub.3 O.sub.2 
Found 
______________________________________ 
C% 69.43 69.13 
H% 6.80 6.88 
N% 13.50 13.69 
______________________________________ 
EXAMPLE XXIII 
Preparation of N-[(4'-dimethylamino-2'-methoxy) 
phenyl]-6-methyl-3-acetylamino benzoquinoneimine. 
##STR32## 
0.01 mole (1.65 g) of 2-methyl-5-acetylamino phenol is dissolved in 50 cc 
of a 0.6 N NaOH solution. To the resulting solution, cooled to 0.degree. 
C., there are added, little by little, with agitation and simultaneously 
with the aid of a double funnel, 0.01 mole (2.64 g) of 
3-methoxy-4-amino-N,N-dimethylaniline sulfate dissolved in 20 cc of water, 
and 0.02 mole (4.6 g) of ammonium persulfate dissolved in 20 cc of water 
to which have been added 5 cc of ammonia (22.degree. Be). At the end of 
this addition, the stirring of the reaction mixture is continued for 15 
minutes. The above indoaniline which has precipitated is then filtered, 
washed with water, recrystallized in a mixture of dimethylformamide and 
water and dried under a vacuum at 80.degree. C. It exhibits a melting 
point of 184.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.21 N.sub.3 O.sub.3 
Found 
______________________________________ 
C% 66.03 65.82 
H% 6.47 6.60 
N% 12.84 13.02 
______________________________________ 
EXAMPLE XXIV 
Preparation of N-[(4'-dimethylamino-2'-methoxy) 
phenyl]-6-methyl-3-carbethoxyamino benzoquinoneimine. 
##STR33## 
0.02 mole (5.28 g) of 3-methoxy-4-amino-N,N-dimethylaniline sulfate and 
0.02 mole (3.9 g) of 2-methyl-5-carbethoxyamino phenol are dissolved in 25 
cc of acetone, 50 cc of water and 15 cc of ammonia (22.degree. Be). To the 
resulting solution, cooled to about 0.degree. C., there is added, little 
by little, with agitation, 0.04 mole (9.2 g) of ammonium persulfate 
dissolved in 40 cc of water. At the end of this addition, stirring of the 
reaction mixture is continued for 30 minutes. The above indoaniline which 
has precipitated in the form of crystals is filtered, washed with water, 
recrystallized in a mixture of dimethylformamide and water and dried under 
a vacuum at 100.degree. C. It exhibits a melting point of 182.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.19 H.sub.23 N.sub.3 O.sub.4 
Found 
______________________________________ 
C% 63.85 63.88 
H% 6.48 6.39 
N% 11.76 11.80 
______________________________________ 
EXAMPLE XXV 
Preparation of N-[(4'-dimethylamino-2'-methyl) phenyl]-2,6-dimethyl-3-amino 
benzoquinoneimine. 
##STR34## 
0.02 mole (3.47 g) of the hydrochloride of 2,6-dimethyl-5-amino phenol is 
dissolved in 40 cc of acetone, 10 cc of water and 30 cc of ammonia (22 
Be). To the resulting solution, maintained at a temperature of about 
+5.degree. C., there are added, little by little, with agitation and 
simultaneously with the aid of a double funnel, 0.02 mole (4.46 g) of the 
dihydrochloride of 3-methyl-4-amino-N,N-dimethylaniline dissolved in 25 cc 
of water, and 0.02 mole (4.60 g) of ammonium persulfate dissolved in 20 cc 
of water. At the end of these additions, stirring of the reaction mixture 
is continued for one hour at ambient temperature. The above indoaniline 
which has precipitated in the form of crystals is filtered, washed with 
water, recrystallized in a mixture of dimethylformamide and water and 
dried under a vacuum. It exhibits a melting point of 170.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.21 N.sub.3 O 
Found 
______________________________________ 
C% 72.05 71.85 
H% 7.47 7.22 
N% 14.83 14.90 
______________________________________ 
EXAMPLE XXVI 
Preparation of N-[(4'-dimethylamino-2'-chloro) phenyl]-2,6-dimethyl-3-amino 
benzoquinoneimine. 
##STR35## 
0.02 mole (3.5 g) of the hydrochloride of 2,6-dimethyl-5-amino phenol and 
0.022 mole (5.36 g ) of the dihydrochloride of 
3-chloro-4-amino-N,N-dimethylaniline are dissolved in 50 cc of acetone, 40 
cc of water and 40 cc of ammonia (22.degree. Be). To the resulting 
solution there are added 100 cc of H.sub.2 O.sub.2 (20 volumes) and the 
resulting mixture is left to stand for 6 hours at ambient temperature. The 
above indoaniline which has precipitated in the form of crystals is then 
filtered, washed with water and dried under a vacuum. It exhibits a 
melting point of 183.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.18 ClN.sub.3 O 
Found 
______________________________________ 
C% 63.25 63.16 
H% 5.97 6.00 
N% 13.83 13.98 
Cl% 11.67 11.79 
______________________________________ 
EXAMPLE XXVII 
Preparation of N-[(4'-dimethylamino-2'-methoxy) 
phenyl]-2,6-dimethyl-3-amino benzoquinoneimine. 
##STR36## 
Into 50 cc of a 0.6 N NaOH solution to which have been added 20 cc of 
ethanol, there are introduced 0.02 mole (3.6 g) of 
3-methoxy-4-nitroso-N,N-dimethylaniline and 0.022 mole (3.9 g) of the 
hydrochloride of 2,6-dimethyl-5-amino phenol. The resulting reaction 
mixture is stirred for one hour at 50.degree. C. The above indoaniline 
which precipitates is then filtered and washed several times with water at 
50.degree. C., and then with acetone. After recrystallization in ethyl 
acetate and drying under a vacuum, it exhibits a melting point of 
152.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.21 N.sub.3 O.sub.2 
Found 
______________________________________ 
C% 68.20 68.09 
H% 7.07 7.21 
N% 14.04 14.23 
______________________________________ 
EXAMPLE XXVIII 
Preparation of N-[(4'-dimethylamino-2'-methyl) 
phenyl]-2,6-dimethyl-3-acetylamino benzoquinoneimine. 
##STR37## 
0.01 mole (1.79 g) of 2,6-dimethyl-5-acetylamino phenol is dissolved in 20 
cc of acetone, 5 cc of water and 15 cc of ammonia (22.degree. Be). To the 
resulting solution, maintained at a temperature of about +5.degree. C., 
there are added, little by little, with agitation and simultaneously with 
the aid of a double funnel, 0.01 mole (2.23 g) of the dihydrochloride of 
3-methyl-4-amino-N,N-dimethylaniline dissolved in 15 cc of water, and 0.02 
mole (4.6 g) of ammonium persulfate dissolved in 20 cc of water. At the 
end of these additions, the stirring of the reaction mixture is continued 
for one hour at ambient temperature. The above indoaniline which has 
precipitated is then filtered, washed with water, recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 184.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.19 H.sub.23 N.sub.3 O.sub.2 
Found 
______________________________________ 
C% 70.13 70.00 
H% 7.12 7.42 
N% 12.91 13.01 
______________________________________ 
EXAMPLE XXIX 
Preparation of N-[(4'-dimethylamino-2'-chloro) 
phenyl]-2,6-dimethyl-3-acetylamino benzoquinoneimine. 
##STR38## 
0.01 mole (1.79 g) of 2,6-dimethyl-5-acetylamino phenol and 0.01 mole (2.44 
g) of the dihydrochloride of 3-chloro-4-amino-N,N-dimethylaniline are 
dissolved in 20 cc of acetone, 15 cc of water and 15 cc of ammonia 
(22.degree. Be). To the resulting solution, cooled to about +5.degree. C., 
there is added, little by little, with agitation, 0.02 mole (4.6 g) of 
ammonium persulfate dissolved in 20 cc of water. At the end of this 
addition, the stirring of the reaction mixture is continued for 30 
minutes. The above indoaniline which has precipitated is then filtered, 
washed with water, recrystallized in a mixture of dimethylformamide and 
water and dried under a vacuum at 100.degree. C. It exhibits a melting 
point of 182.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.20 ClN.sub.3 O.sub.2 
Found 
______________________________________ 
C% 62.52 62.58 
H% 5.83 6.00 
N% 12.15 12.33 
Cl% 10.25 10.00 
______________________________________ 
EXAMPLE XXX 
Preparation of N-[(4'-dimethylamino-2'-methoxy) 
phenyl]2,6-dimethyl-3-acetylamino benzoquinoneimine. 
##STR39## 
0.01 mole (2.64 g) of 3-methoxy-4-amino-N,N-dimethylaniline sulfate and 
0.01 mole (1.8 g) of 2,6-dimethyl-5-acetylamino phenol are dissolved in 25 
cc of acetone, 50 cc of water and 15 cc of ammonia (22.degree. Be). To the 
resulting solution, maintained at a temperature of about 0.degree. C., 
there is added, little by little, with agitation, 0.02 mole (4.6 g) of 
ammonium persulfate dissolved in 20 cc of water. At the end of this 
addition, the stirring of the reaction mixture is continued for 30 
minutes. The above indoaniline which has precipitated is then filtered, 
washed first with water, then with a little dimethylformamide and finally 
with water. After drying under a vacuum, the product exhibits a melting 
point of 186.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.19 H.sub.23 N.sub.3 O.sub.3 
Found 
______________________________________ 
C% 66.84 66.64 
H% 6.79 6.70 
N% 12.31 12.42 
______________________________________ 
EXAMPLE XXXI 
Preparation of N-](4'-dimethylamino-2'-chloro) 
phenyl]-6-methyl-3-(.beta.-hydroxyethylamino) benzoquinoneimine. 
##STR40## 
0.01 mole (1.67 g) of 2-methyl-5-(N-.beta.hydroxy-ethylamino) phenol is 
dissolved in 10 cc of acetone, 5 cc of water and 15 cc of ammonia 
(22.degree. Be). To the resulting solution, maintained at a temperature of 
about + 5.degree. C., there are added, little by little, with agitation 
and simultaneously with the aid of a double funnel, 0.01 mole (2.43 g) of 
the dihydrochloride of 3-chloro-4-amino-N,N-dimethylaniline dissolved in 
15 cc of water, and 0.01 mole (2.3 g) of ammonium persulfate dissolved in 
10 cc of water. At the end of these additions, the stirring of the 
reaction mixture is continued for 30 minutes. The above indoaniline which 
has precipitated in the form of crystals is then filtered, washed with 
water, recrystallized in a mixture of dimethylformamide and water and 
dried under a vacuum. It exhibits a melting point of 176.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.20 N.sub.3 O.sub.2 Cl 
Found 
______________________________________ 
C% 61.17 60.94 
H% 5.99 6.10 
N% 12.60 12.51 
Cl% 10.65 10.60 
______________________________________ 
EXAMPLE XXXII 
Preparation of N-[(4,'-diethylamino-3'-methyl) 
phenyl]-6-methyl-3-acetylamino benzoquinoneimine. 
##STR41## 
0.0064 mole (1.06 g) of 2-methyl-5-acetylamino phenol and 0.0064 (1.65 g) 
of 2-methyl-4-amino-N,N-diethyl aniline are dissolved in 80 cc of a 50% 
hydroacetonic solution to which have been added 20 cc of ammonia 
(22.degree. Be). To the resulting solution, cooled to 0.degree. C., there 
is added, little by little, with a little agitation, 0.0128 mole (2.9 g) 
of ammonium persulfate dissolved in b 20 cc of water. The resulting 
reaction mixture is left to stand overnight at 0.degree. C. The above 
indoaniline which forms first as an oil, crystallizes and the resulting 
crystals are filtered, washed with water and recrystallized in a mixture 
of dimethylformamide and water. After drying under a vacuum the product 
exhibits a melting point of 84.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.20 H.sub.25 N.sub.3 O.sub.2 . 0.5H.sub.2 O 
Found 
______________________________________ 
C% 68.94 68.97 
H% 7.52 7.42 
N% 12.06 11.98 
______________________________________ 
EXAMPLE XXXIII 
Preparation of N-[(4'-dimethylamino-3'-chloro) phenyl]-2,6-dimethyl 
benzoquinoneimine. 
##STR42## 
0.01 mole (1.22 g) of 2,6-dimethyl phenol and 0.01 mole (1.70 g) of 
2-chloro-4-amino-N,N-dimethyl aniline are dissolved in 30 cc of a 50% 
hydroacetonic solution to which have been added 15 cc of ammonia 
(22.degree.Be). To the resulting solution, maintained at a temperature of 
0.degree. C., there is added, little by little, with agitation 0.02 mole 
(4.6 g) of ammonium persulfate dissolved in 20 cc of water. At the end of 
this addition, the stirring of the reaction mixture is continued for 30 
minutes. The above indoaniline which has precipitated in the form of 
crystals is then filtered, washed with water and recrystallized in a 
mixture of dimethylformamide and water and dried under a vacuum. It 
exhibits a melting point of 62.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.17 ClN.sub.2 O 
Found 
______________________________________ 
C% 66.19 66.39 
H% 5.58 5.73 
N% 9.70 9.87 
Cl% 12.27 12.47 
______________________________________ 
EXAMPLE XXXIV 
Preparation of N-[(4'-dimethylamino-3'-chloro) phenyl]-6-methyl-3-amino 
benzoquinoneimine. 
##STR43## 
0.004 mole (1.33 g) of N-[(4'-dimethylamino-3'-chloro) 
phenyl]-6-methyl-3-acetylamino benzoquinoneimine is introduced into 32 cc 
of a 1N NaOH solution to which have been added 8 cc of ethyl alcohol 
(95.degree. titer). The resulting reaction mixture is agitated for a 
period of 24 hours while maintaining the temperature thereof at about 
25.degree. C. The above indoaniline which precipitates is then filtered 
and washed with water. The raw product contains only a trace of the 
initial reactant (measured by chromatography). After recrystallization of 
this raw product in a mixture of dimethylformamide and water and washing 
with acetone it is chromatographically pure. After drying under a vacuum, 
it exhibits a melting point of 152.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.15 H.sub.16 ClN.sub.3 O 
Found 
______________________________________ 
C% 62.16 62.38 
H% 5.56 5.36 
N% 14.50 14.57 
Cl% 12.23 12.13 
______________________________________ 
EXAMPLE XXXV 
Preparation of N-[(4'-dimethylamino-3'-chloro) phenyl]-6-chloro-3-amino 
benzoquinoneimine. 
##STR44## 
0.01 mole (1.70 g) of 2-chloro-4-amino-N,N-dimethylaniline and 0.01 mole 
(1.43 g) of 2-chloro-5-amino phenol are dissolved in 20 cc of water, 30 cc 
of ethyl alcohol (95.degree. titer) and 10 cc of ammonia (22.degree. Be). 
To the resulting solution, maintained at a temperature of about 0.degree. 
C., there is added, little by little, with agitation, 0.01 mole (2.3 g) of 
ammonium persulfate dissolved in 20 cc of water. At the end of this 
addition, the stirring of the reaction mixture is continued for 30 
minutes. The above indoaniline which has precipitated in the form of 
reddish brown flakes with golden glints is then filtered, washed with 
water and recrystallized in a mixture of dimethylformamide and water. 
After drying under a vacuum at 100.degree. C., the product exhibits a 
melting point of 182.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.14 H.sub.13 N.sub.3 Cl.sub.2 O 
Found 
______________________________________ 
C% 54.19 54.19 
H% 4.19 4.30 
N% 13.54 13.66 
Cl% 22.90 23.12 
______________________________________ 
EXAMPLE XXXVI 
Preparation of N-[(4'-dimethylamino-3'-chloro) phenyl]-2,6-dimethyl-3-amino 
benzoquinoneimine. 
##STR45## 
0.02 mole (3.47 g) of the hydrochloride of 2,6-dimethyl-5-amino phenol and 
0.02 mole (3.42 g) of 2-chloro-4-amino-N,N-dimethylaniline are dissolved 
in 120 cc of a 50% hydroacetonic solution to which have been added 30 cc 
of ammonia (22.degree. Be). To the resulting solution, maintained at a 
temperature of 0.degree. C., there is added, little by little, with 
agitation 0.04 mole (9.2 g) of ammonium persulfate dissolved in 40 cc of 
water. At the end of this addition, the stirring of the reaction mixture 
is continued for 30 minutes at 0.degree. C. The above indoaniline which 
precipitates is then filtered, washed with water and recrystallized in a 
mixture of dimethylformamide and water. After drying under a vacuum at 
60.degree. C., it exhibits a melting point of 137.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.16 H.sub.18 N.sub.3 OCl . 0.5H.sub.2 O 
Found 
______________________________________ 
C% 61.44 61.25 
H% 6.08 6.16 
N% 13.44 13.24 
Cl% 11.36 11.31 
______________________________________ 
EXAMPLE XXXVII 
Preparation of N-[(4'-dimethylamino-3'-chloro) 
phenyl]-6-methyl-3-acetylamino benzoquinoneimine. 
##STR46## 
0.01 mole (1.65 g) of 2-methyl-5-acetylamino phenol and 0.01 mole (1.71 g) 
of 2-chloro-4-amino-N,N-dimethylaniline are dissolved in 60 cc of a 50% 
hydroacetonic solution to which have been added 15 cc of ammonia 
(22.degree. Be). To the resulting solution, maintained at a temperature of 
about 0.degree. C., there is added, little by little, with agitation, 0.02 
mole (4.6 g) of ammonium persulate dissolved in 20 cc of water. At the end 
of this addition, the stirring of the reaction mixture is continued for 30 
minutes. The above indoaniline which has precipitated in the form of 
crystals is then filtered, washed with water, recrystallized in a mixture 
of dimethylformamide and water and dried under a vacuum. It exhibits a 
melting point of 156.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.17 H.sub.18 O.sub.2 N.sub.3 Cl . 0.5H.sub.2 O 
Found 
______________________________________ 
C% 59.91 59.87 
H% 5.62 5.60 
N% 12.33 12.58 
Cl% 10.40 10.52 
______________________________________ 
EXAMPLE XXXVIII 
Preparation of N-[(4'-dimethylamino-3'-chloro) 
phenyl]-2,6-dimethyl-3-acetylamino benzoquinoneimine. 
##STR47## 
0.2 mole (35.8 g) of 2,6-dimethyl-5-acetylamino phenol and 0.2 mole (34.0 
g) of 2-chloro-4-amino-N,N-dimethylaniline are dissolved in 600 cc of a 
50% hydroacetonic solution to which have been added 300 cc of ammonia 
(22.degree. Be). To the resulting solution, maintained at a temperature of 
about +5.degree. C., there is added, little by little, with agitation, 0.4 
mole (92 g) of ammonium persulfate dissolved in 400 cc of water. At the 
end of this addition, the stirring of the reaction mixture is continued 
for 30 minutes. The above indoaniline which has precipitated is then 
filtered, washed with water, recrystallized in a mixture of 
dimethylformamide and water and dried under a vacuum. It exhibits a 
melting point of 136.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.20 Cl N.sub.3 O.sub.2 
Found 
______________________________________ 
C% 62.52 62.54 
H% 5.82 5.95 
N% 12.15 12.24 
Cl% 10.25 10.42 
______________________________________ 
EXAMPLE XXXIX 
Preparation of N-[(4'-dimethylamino-3'-chloro) 
phenyl]-6-methyl-3-carbethoxyamino benzoquinoneimine. 
##STR48## 
0.1 mole (17 g) of 2-chloro-4-amino-N,N-dimethylaniline and 0.1 mole (19.5 
g) of 2-methyl-5-carbethoxyamino phenol are dissolved in 500 cc of ethyl 
alcohol (95.degree. titer), 250 cc of water and 150 cc of ammonia 
(22.degree. Be). To the resulting solution maintained at a temperature of 
about 0.degree. C., there is added, little by little, with agitation, 0.2 
mole (46 g) of ammonium persulfate dissolved in 200 cc of water. At the 
end of this addition, the stirring of the reaction mixture is continued 
for one hour. The above indoaniline which has precipitated in the form of 
crystals is then filtered and washed with a 50% hydroethanolic solution. 
After recrystallization in a mixture of dimethylformamide and water and 
drying under a vacuum at 100.degree. C., the product exhibits a melting 
point of 142.degree. C. 
______________________________________ 
Calculated For 
Analysis C.sub.18 H.sub.20 N.sub.3 O.sub.3 Cl 
Found 
______________________________________ 
C% 59.75 59.81 
H% 5.54 5.69 
N% 11.62 11.55 
Cl% 9.82 9.89 
______________________________________ 
EXAMPLES OF USE 
Section A - Examples of Hair Setting Lotions 
______________________________________ 
(a) Dye according to Example IV 
0.02 g 
Coploymer of vinyl acetate and 
crotonic acid 90/10; molecular 
weight 45,000 to 50,000 
1 g 
Isopropyl alcohol 20 g 
Triethanolamine q.s.p. pH 6.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a purple-ash shade. 
______________________________________ 
(b) Dye according to Example VI 
0.15 g 
Terpolymer of methylmethacrylate/ 
stearylmethacrylate/dimethylmethacrylate, 
20/23/57 (made in accordance with SN 287,845 
2.5 g 
filed 11-9-1972) 
Ethyl alcohol (96.degree.) 30 g 
Triethanolamine q.s.p. pH 7.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silvery, blue-gray coloration. 
______________________________________ 
(c) Dye according to Example VIII 
0.1 g 
Polyvinylpyrrolidone - M.W. 40,000 
2 g 
Isopropyl alcohol 35 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a chatoyant sea-green coloration. 
______________________________________ 
(d) Dye according to Example V 
0.15 g 
Copolymer of vinyl acetate/ 
crotonic acid 90/10, M.W. 45,000 
to 50,000 1.5 g 
Ethyl alcohol (96.degree.) 
30 g 
Triethanolamine q.s.p. pH 6.2 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a bright blue-green coloration. 
______________________________________ 
(e) Dye according to Example XI 
0.12 g 
Polyvinylpyrrolidone, M.W. 40,000 
1 g 
Ethyl alcohol (96.degree.) 
20 g 
Triethanolamine q.s.p. pH 10.2 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a Nordic ash-blond coloration. 
______________________________________ 
(f) N-[(4'-dimethylamino) phenyl]-3- 
acetylamino benzoquinoneimine 
0.2 g 
Polyvinylpyrrolidone/vinyl acetate, 
70/30, M.W. 40,000 3 g 
Ethyl alcohol (96.degree.) 
45 g 
Triethanolamine q.s.p. pH 7.8 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silvery Prussian blue coloration. 
______________________________________ 
(g) Dye according to Example X 
0.04 g 
Terpolymer of methylmethacrylate/ 
stearylmethacrylate/dimethyl- 
methacrylate, 20/23/57 (made in accordance 
3 g 
with SN 287,845 filed 11-9-1972) 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 8.2 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pale glycine coloration. 
______________________________________ 
(h) N-[(4'-dimethylamino) phenyl]- 
2,6-ditert. butyl benzoquinone- 
imine 0.05 g 
Polyvinylpyrrolidone, M.W. 40,000 
3 g 
Isopropyl alcohol 50 g 
Triethanolamine q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a mauve shade. 
______________________________________ 
(i) N-[(4'-dimethylamino) phenyl]- 
3-methoxy benzoquinoneimine 
0.1 g 
Polyvinylpyrrolidone, M.W. 40,000 
1.5 g 
Ethyl alcohol (96.degree.) 
30 g 
Triethanolamine q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light lavender-blue color. 
______________________________________ 
(j) Dye according to Example I 
0.08 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40 M.W. 80.000-120.000 
2 g 
Ethyl alcohol (96.degree.) 
25 g 
Triethanolamine q.s.p. pH 8.7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pale shade with golden lights. 
______________________________________ 
(k) N-[(4'-dimethylamino) phenyl] 
benzoquinoneimine 0.12 g 
Copolymer of polyvinylpyrridone/ 
vinyl acetate, 60/40, M.W. 80.000-120.000 
2.5 g 
Isopropyl alcohol 40 g 
Triethanolamine q.s.p. pH 7.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pale-green coloration with golden lights. 
______________________________________ 
(l) Dye according to Example IX 
0.05 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 70/30, M.W. 40,000 
1 g 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 6.8 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a bright sea-green coloration. 
______________________________________ 
(m) Dye according to Example VII 
0.05 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 70/30, M.W. 40,000 
2 g 
Isopropyl alcohol 45 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly, pale rose shade. 
______________________________________ 
(n) Dye according to Example II 
0.1 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, M.W. 160,000 
3 g 
Isopropyl alcohol 50 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a steel, blue-gray coloration. 
______________________________________ 
(o) N-[(4'-dimethylamino) phenyl]- 
2,5-dimethyl benzoquinoneimine 
0.15 g 
Copolymer of vinyl acetate/ 
crotonic acid 90/10, M.W. 45,000 
to 5,000 1 g 
Ethyl alcohol (96.degree.) 
40 g 
Triethanolamine q.s.p. pH 10 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a steel, blue-gray coloration. 
______________________________________ 
(p) Dye according to Exxample III 
0.08 g 
Copolymer of vinyl acetate/crotonic 
acid 90/10, M.W. 45,000-50,000 
1 g 
Ethyl alcohol 50 g 
Triethanolamine q.s.p.10 pH 9.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto an ash-gray coloration. 
______________________________________ 
(q) N-[(4'-dimethylamino) phenyl]- 
2,6-dimethyl benzoquinoneimine 
0.05 g 
Polyvinylpyrrolidone, M.W. 40,000 
3 g 
Isopropyl alcohol 40 g 
Triethanolamine q.s.p. pH 10.2 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silvery, blue-green coloration. 
______________________________________ 
(r) Dye according to Example XII 
0.08 g. 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, M.W. 160,000 
1.5 g 
Ethyl alcohol (96.degree.) 
25 g 
Triethanolamine q.s.p. pH 7.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly beige coloration. 
______________________________________ 
(s) Dye according to Example XIII 
0.09 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 70/30, M.W. 40,000 
1.5 g 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto, a rose-gray coloration. 
______________________________________ 
(t) Dye according to Example XIV 
0.52 g 
Copolymer of vinyl acetate/ 
crotonic acid 90/10, M.W. 45,000- 
50,000 2 g 
Ethanol (96.degree.) 50 g 
Water q.s.p. 100 g 
Triethanolamine q.s.p. pH 7 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto, a light silvery-gray coloration. 
______________________________________ 
(u) Dye according to Example XV 
0.04 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, M.W. 60,000 
2 g 
Ethyl alchohol (96.degree.) 
40 g 
Triethanolamine, q.s.p. pH 9 
Water q.s.p. 100 6 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light pearly blue coloration. 
______________________________________ 
(v) Dye according to Example XVI 
0.2 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, M.W. 60,000 
2 g 
Ethyl alcohol (96.degree.) 
40 g 
Triethanolamine, q.s.p. pH 7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a lightly violaceous blue coloration. 
______________________________________ 
(w) Dye according to Example XVII 
0.0075 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40, sold under 
the name of PVP/VA S630 
2 g 
Isopropanol 35 g 
Triethanolamine q.s.p. pH 7.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light pearly turquoise blue coloration. 
______________________________________ 
(x) Dye according to Example XVIII 
0.25 g 
Copolymer of vinyl acetate/ 
crontonic acid, 90/10, M.W. - 45,000 
to 50,000 2 g 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting location to bleached hair 
imparts thereto an intense violet coloration. 
______________________________________ 
(y) Dye according to Example XIX 
0.6 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 1 g 
Ethyl alcohol (96.degree.) 
36 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a vary luminous parme coloration. 
______________________________________ 
(z) Dye according to Example XX 
0.26 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 
50 g 
Lactic acid - 10% solution, 
q.s.p. pH 4.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a very silvery light violet coloration. 
______________________________________ 
(aa) Dye of Example XXI 0.1 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, sold under 
the name PVP/VAE E335 2 g 
Ethyl alcohol (96.degree.) 
40 g 
Ammonia (22.degree. Be), q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly rose beige coloration. 
______________________________________ 
(ab) Dye of Example XXII 0.15 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40, sold under 
the name PVP/VA S630 2 g 
Isopropanol 35 g 
Triethanolamine, q.s.p. pH 9.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly light blue coloration. 
______________________________________ 
(ac) Dye of Example XXIII 0.1 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40, sold under 
the name PVP/VA S630 2 g 
Isopropanol 35 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light blue coloration. 
______________________________________ 
(ad) Dye of Example XXIV 0.05 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, sold under 
the name PVP/VAE E335 2 g 
Ethyl alcohol (96.degree.) 
40 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silvery light blue-gray coloration. 
______________________________________ 
(ae) Dye of Example XXV 0.15 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 1 g 
Ethyl alcohol (96.degree.) 
36 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silvery glycine coloration. 
______________________________________ 
(af) Dye of Example XXVI 0.05 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a golden-rose coloration. 
______________________________________ 
(ag) Dye of Example XXVII 0.12 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, sold under 
the name PVP/VAE E335 2 g 
Ethyl alcohol (96.degree.) 
40 g 
Ammonia 22.degree. Be), q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a very luminous parme coloration. 
______________________________________ 
(ah) Dye of Example XXVIII 0.12 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40, sold under 
the name PVP/VA S630 2 g 
Isopropanol 35 g 
Ammonia (22.degree. Be), q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a myosotis cloration. 
______________________________________ 
(ai) Dye of Example XXIX 0.05 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 
50 g 
Ammonia (22.degree. Be) q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a silver-gray coloration with violet glints. 
______________________________________ 
(aj) Dye of Example XXX 0.2 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 60/40, sold under 
the name PVP/VA S630 2 g 
Isopropanol 35 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a intense French blue coloration. 
______________________________________ 
(ak) Dye of Example XXXI 0.05 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 
50 g 
Triethanolamine q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly dog-rose coloration. 
______________________________________ 
(al) Dye of Example XXXI 0.25 g 
N-[(4'-hydroxy-3'-chloro) phenyl]- 
2-methyl-5-.beta.-hydroxyethylamino 
benzoquinoneimine 0.25 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 
36 g 
Ammonia (22.degree. Be) q.s.p. pH 8 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a rose beige coloration with golden glints. 
______________________________________ 
(am) Dye of Example XIX 0.12 g 
Dye of Example XVII 0.05 g 
N-[(4'-hydroxy-3'-chloro) phenyl]-2, 
6-dimethyl-5-amino benzoquinoneimine 
0.35 
Nitroorthophenylenediamine 0.02 g 
Terpolymer of methylmethacrylate/ 
stearylmethacrylate/dimethyl- 
methacrylate, 20/23/57 (made in accordance 
1.25 
with SN 287,845 filed 11-9-1972) 
Ethyl alcohol (96.degree.) 15 g 
Ammonia (22.degree. Be) q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto an ash gray coloration. 
______________________________________ 
(an) Dye of Example XVIII 0.2 g 
N-[(4'-hydroxy) phenyl] -2-methyl- 
5-.beta.-hydroxyethylamino benzo- 
quinoneimine 0.30 g 
N-[(4'-hydroxy) phenyl] -2-methyl- 
5-carbethoxyamino benzoquinone- 
imine 0.20 g 
Polyvinylpyrrolidone, M.W. 160,000 
2 g 
Isopropanol 25 g 
Ammonia (22.degree. Be) q.s.p. pH 9.7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a mahogony coloration. 
______________________________________ 
(ao) Dye of Example XXXII 0.5 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 50 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a tamarisk rose coloration. 
______________________________________ 
(ap) Dye of Example XXXIII 0.025 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 50 g 
Triethanolamine q.s.p. pH 7.5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pink champagne coloration. 
______________________________________ 
(aq) Dye of Example XXXIV 0.040 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 50 g 
Triethanolamine q.s.p. pH 7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light yellow-orange coloration. 
______________________________________ 
(ar) Dye of Example XXXV 0.08 g 
Polyvinylpyrrolidone, M.W. 160,000 
1.5 g 
Ethyl alcohol (96.degree.) 50 g 
Ammonia (22.degree. Be) q.s.p. pH 10 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a pearly rose beige coloration. 
______________________________________ 
(as) Dye of Example XXXVI 0.2 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 1 g 
Ethyl alcohol (96.degree.) 36 g 
Ammonia (22.degree. Be) q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a light orange coloration. 
______________________________________ 
(at) Dye of Example XXXVII 0.1 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 50 g 
Triethanolamine q.s.p. pH 7 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a very luminous light salmon coloration. 
______________________________________ 
(au) Dye of Example XXXVIII 0.5 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, sold under 
the name PVP/VAE E335 2 g 
Ethyl alcohol (96.degree.) 40 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a salmon rose coloration. 
______________________________________ 
(av) Dye of Example XXXIX 0.075 g 
Copolymer of polyvinylpyrrolidone/ 
vinyl acetate, 30/70, sold under 
the name PVP/VAE E335 2 g 
Ethyl alcohol (96.degree.) 40 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto a golden sand coloration with light pink glints. 
______________________________________ 
(aw) Dye of Example XXXVII 0.10 g 
Dye of Example XXXVI 0.12 g 
N-[ (4'-amino-2'-methoxy-3',5'- 
dimethyl) phenyl]-2,6-dimethyl- 
3-acetylamino benzoquinoneimine 
0.05 g 
2-N,N-(methyl,.beta.-hydroxyethyl)amino-5- 
(4'-amino) anilino-1,4-benzoquinone 
0.08 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethyl alcohol (96.degree.) 50 g 
Ammonia (22.degree. Be) q.s.p. pH 10 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to bleached hair 
imparts thereto an ash beige coloration. 
______________________________________ 
(ax) Dye of Example XXXVI 0.20 g 
N-[ (4'-amino-2'-methoxy-3'-5'- 
dimethyl) phenyl]-2,6-dimethyl- 
3-acetylamino benzoquinoneimine 
0.04 g 
N-[ (4'-(ethyl,.beta.-mesylaminoethyl) 
amino-2'-methyl) phenyl]-2,3- 
dimethyl benzoquinoneimine 0.25 g 
Copolymer of vinyl acetate/ 
crotonic acid, 90/10, M.W. - 
45,000 to 50,000 2 g 
Ethanol (95.degree.) 50 g 
Triethanolamine q.s.p. pH 6 
Water q.s.p. 100 g 
______________________________________ 
This composition when applied as a hair setting lotion to 95% naturally 
white hair, imparts thereto a metallic gray coloration with violet glints. 
Section B - Examples of Dye Compositions 
______________________________________ 
(a) N-[(4'-dimethylamino) phenyl]-3- 
acetylamino benzoquinoneimine 
0.3 g 
Ammonium lauryl sulfate 20 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of thirty minutes to white 
hair at ambient temperature. The hair is then rinsed, shampooed, rinsed 
again and then dried. A pearly sea-green coloration is thus imparted to 
the hair. 
______________________________________ 
(b) Dye according to Example V 0.2 g 
Ammonium lauryl sulfate 20 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of thirty minutes to white 
hair at ambient temperature. The hair is then rinsed, shampooed, rinsed 
again and dried. The sea-green coloration is thus imparted to the hair. 
______________________________________ 
(c) Dye according to Example VI 0.3 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated with 
10.5 moles of ethylene oxide 
5 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, a lavender-blue coloration is imparted to the hair. 
______________________________________ 
(d) N-[(4'-dimethylamino) phenyl]-3- 
acetylamino benzoquinoneimine 
0.3 g 
Ethanol (96.degree.) 30 g 
Acetic acid q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for about thirty minutes to previously 
bleached hair. At the end of this period, the hair is rinsed and dried. A 
brilliant turquoise coloration is thus imparted to the hair. 
______________________________________ 
(e) Dye of Example XVII 0.15 g 
Diethanolamides of the fatty 
acids of coprah 10 g 
Phosphoric acid - 10% solution, 
q.s.p. pH 4 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at 
35.degree. C., to bleached hair and after rinsing, shampooing, and rinsing 
again imparts thereto a turquoise blue coloration. 
______________________________________ 
(f) Dye of Example XIX 2 g 
Diethanolamides of fatty 
acids of coprah 10 g 
Ammonia (22.degree. Be) q.s.p. pH 10 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes to 90% 
naturally white hair at 35.degree. C., and after rinsing, shampooing and 
rinsing again imparts thereto a blue gray coloration. 
______________________________________ 
(g) Dye of Example XX 0.3 g 
Sodium lauryl sulfate with 19% 
of the starting alcohol being 
oxyethylenated 20 g 
Ethylenediamine tetraacetic acid- 
"TRILON B" 0.2 g 
Ammonia (22.degree. Be) q.s.p. pH 11 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at 
30.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a light silver coloration with mauve glints. 
______________________________________ 
(h) Dye of Example XXI 0.2 g 
Monomethyl ester of diethylene 
glycol 10 g 
Ammonia (22.degree. Be) q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of thirty minutes at 
25.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again imparts thereto a golden rose coloration. 
______________________________________ 
(i) Dye of Example XXIII 0.1 g 
Ammonium lauryl sulfate 10 g 
acetic acid - 5% solution, 
q.s.p. pH 7 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes at 
35.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a pearly light turquoise coloration. 
______________________________________ 
(j) Dye of Example XXIV 0.25 g 
Carboxymethyl cellulose 5 g 
Ammonia (22.degree. Be) q.s.p. pH 11 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes at 
35.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a light silver coloration with bluish glints. 
______________________________________ 
(k) Dye of Example XXVII 0.3 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated 
with 10.5 moles of ethylene 
oxide 5 g 
Ammonia (22.degree. Be) q.s.p. ph 10 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes at 
35.degree. C., to 95% naturally white hair and after rinsing, shampooing 
and rinsing again, imparts theto a silver gray coloration with mauve 
glints. 
______________________________________ 
(1) Dye of Example XXX 0.20 g 
Carboxymethyl cellulose 5 g 
Ammonia (22.degree. Be) q.s.p. pH 8 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes at 
20.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a silvery light blue coloration. 
______________________________________ 
(m) Dye of Example XXVII 0.30 g 
N-[(4'-hydroxy-2'-chloro) phenyl]- 
2-methyl-5-amino benzoquinoneimine 
0.40 g 
Ethyl alcohol (96.degree.) 20 g 
Diethanolamides of fatty acids 
of coprah 8 g 
Ammonia (22.degree. Be) q.s.p. pH 9.3 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at ambient 
temperature to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a light golden blond coloration with pink glints. 
______________________________________ 
(n) Dye of Example XXXIII 0.75 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated 
with 10.5 moles of ethylene oxide 
5 g 
Ammonia (22.degree. Be) q.s.p. pH 10.5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at ambient 
temperature to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a pale golden pink coloration. 
______________________________________ 
(o) Dye of Example XXXVI 0.1 g 
Lauryl alcohol oxyethylenated 
with 10.5 moles of ethylene oxide 
5 g 
Ammonia (22.degree. Be) q.s.p. pH 10 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at 
35.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a very luminous orange coloration. 
______________________________________ 
(p) Dye of Example XXXVII 0.1 g 
Monomethyl ester of diethylene 
glycol 10 g 
Ammonia (22.degree. Be) q.s.p. pH 11 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty-five minutes at 
35.degree. C., to bleached hair and after rinsing, shampooing and rinsing 
again, imparts thereto a pink beige coloration. 
______________________________________ 
(q) Dye of Example XXXVIII 0.25 g 
Ethyl alcohol (96.degree.) 
20 g 
Carboxymethyl cellulose 
5 g 
Lactic acid - 10% solution, 
q.s.p. pH 5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of ten minutes at 35.degree. 
C., to bleached hair and after rinsing, shampooing and rinsing again, 
imparts thereto a tarmarisk-pink coloration. 
______________________________________ 
(r) Dye of Example XXXIV 0.425 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated 
with 10.5 moles of ethylene oxide 
5 g 
Ammonia (22.degree. Be) q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at ambient 
temperature to bleached hair and imparts thereto a pearly golden sand 
coloration. 
______________________________________ 
(s) Dye of example XXXIII 0.40 g 
Dye of example XXXIX 0,80 g 
N-[(4'-dimethylamino-2'-methoxy) 
phenyl]-2,6-dimethyl-3-acetyl- 
amino benzoquinoneimine 0,15 g 
Diethanolamides of fatty acids of coprah 
10 g 
Ammonia (22.degree. Be) q.s.p. pH 9,7 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied for a period of twenty minutes at ambient 
temperature to bleached hair and imparts thereto a dove gray coloration. 
Section C - Examples of Dye Compositions Containing the Indoanilines of 
Formula (I) and Other Dyes 
______________________________________ 
(a) N-[(4'-dimethylamino) phenyl]-3- 
acetylamino benzoquinoneimine 
0.2 g 
Dihydrochloride of 3-nitro-4-N-(methyl- 
.beta.-diethylaminoethyl) - amino 
aniline 0.1 g 
Ammonium lauryl sulfate 20 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a linden coloration with golden glints. 
______________________________________ 
(b) N- [(4'-dimethylamino) phenyl]-2,6- 
dimethyl benzoquinoneimine 
0.25 g 
2,4,6-trihydroxy-azo benzene 
0.2 g 
Ammonium lauryl sulfate 20 g 
Triethanolamine q.s.p. pH 8.2 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a canary yellow coloration. 
______________________________________ 
(c) N- [(4'-dimethylamino) phenyl]-2,5- 
dimethyl benzoquinoneimine 
0.3 g 
2-amino-4,4'-dihydroxy-azo 
benzene 0.2 g 
Ammonium lauryl sulfate 20 g 
Triethanolamine q.s.p. pH 8.8 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of about thirty 
minutes at ambient temperature . After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a yellow-green coloration. 
______________________________________ 
(d) N- [(4'-dimethylamino) phenyl] 
benzoquinoneimine 0.2 g 
1,4-di-(.beta.-morpholinoethyl) amino 
anthraquinone 0.3 g 
Butylglycol 5 g 
Lauryl alcohol, oxyethylenated 
with 10.5 moles of ethylene oxide 
5 g 
Triethanolamine q.s.p. pH 8.5 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a brilliant lavender-blue coloration. 
______________________________________ 
(e) N- [(4'-dimethylamino) phenyl]-2,6- 
dimethyl-3-amino benzoquinoneimine 
0.2 g 
N- [(4'-amino-2'-methoxy-5'-methyl) 
phenyl]-3-ureido benzoquinoneimine 
0.1 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated with 
10.5 moles of ethylene oxide 
5 g 
Triethanolamine q.s.p. pH 8.6 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of about thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a gray-green coloration. 
______________________________________ 
(f) Dye according to Example IX 
0.2 g 
N- [(4'-amino) phenyl]-2-6-dimethyl 
3-ureido benzoquinoneimine 
0.1 g 
N- [(4'-amino) phenyl]-2-methyl-5- 
ureido benzoquinoneimine 0.1 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated with 
10.5 moles of ethylene oxide 
5 g 
Triethanolamine q.s.p. pH 9 
Water q.s.p. 100 g 
______________________________________ 
This dye composition is applied to white hair for a period of about thirty 
minutes at ambient temperature. After rinsing, shampooing, rinsing again 
and drying, the hair exhibits a parme shade. 
______________________________________ 
(g) N- [(4'-dimethylamino) phenyl]-2,6- 
ditertbutyl benzoquinoneimine 
0.1 g 
N- [(4'-hydroxy-3'-chloro) phenyl]-2- 
chloro-5-amino benzoquinoneimine 
0.1 g 
N- [(4'-dimethylamino) phenyl]-3- 
acetylamino benzoquinoneimine-N',N'- 
dimethyl iminium chloride 0.1 g 
5,6-dihydroxy indole 0.05 g 
Butylglycol 5 g 
Lauryl alcohol oxyethylenated with 
10.5 moles of ethylene oxide 
5 g 
Ammonia q.s.p. pH 11 
Water q.s.p. 100 g 
______________________________________ 
This composition is applied to white hair for a period of about thirty 
minutes. At the end of this period, the hair is rinsed, washed with water 
rinsed again and dried. There is thus imparted to the hair a silvery-seal 
coloration.