Alkyl N-(hydroxyalkyl) carbamates and their application in cosmetics, more particularly in hair compositions

New compounds of formula (I): ##STR1## in which: R.sub.1 represents a C.sub.4 -C.sub.18 alkyl or alkylene radical, R.sub.2 represents a C.sub.2 -C.sub.16 alkyl or alkylene radical, R.sub.3 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl radical, and A represents a non-ionic hydrophilic group, as well as a cosmetic composition containing these compounds and the use of such a cosmetic composition in hair treatment.

The present invention is directed to new alkyl N-(hydroxyalkyl)carbamates 
and their process of preparation. The present invention is also directed 
to cosmetic compositions containing these compounds. More particularly, 
the present invention is directed to the use of such compositions in hair 
treatment. 
The subject of the present invention is therefore compounds of the formula 
(I): 
##STR2## 
in which: R.sub.1 represents an alkyl or alkylene radical having from 4 to 
18 carbon atoms; 
R.sub.2 represents an alkyl or alkylene radical having from 2 to 16 carbon 
atoms; 
R.sub.3 represents a hydrogen atom or an alkyl radical having from 1 to 6 
carbon atoms; and 
A represents a non-ionic hydrophilic group. 
Preferably, R.sub.1 represents an alkyl radical having from 4 to 14 carbon 
atoms; R.sub.2 represents an alkyl radical having from 2 to 12 carbon 
atoms; and R.sub.3 represents a hydrogen atom or a methyl radical. 
Preferably, A represents a radical of the formula: 
EQU --(CH.sub.2).sub.n --(CHOH).sub.m --Z 
in which: n represents an integer equal to 0 or 1; m represents an integer 
ranging from 0 to 5; and Z is a monohydroxylated or polyhydroxylated alkyl 
radical having from 1 to 4 carbon atoms. 
Preferably, Z is chosen from the group comprising the radicals: 
##STR3## 
More preferably, Z is chosen from the group comprising the radicals: 
--CH.sub.2 OH and --C(CH.sub.2 OH).sub.3. 
Mention may particularly be made, among the preferred compounds 
corresponding to formula (I), of: 
N-2-ethylhexyloxycarbonyl-N-methyl-D-glucamine; 
N-2-hexyldecyloxycarbonyl-N-methyl-D-glucamine; 
N-2-butyloctyloxycarbonyl-N-methyl-D-glucamine; 
N-2-decyltetradecyloxycarbonyl-N-methyl-D-glucamine; 
N-2-dodecylhexadecyloxycarbonyl-N-methyl-D-glucamine; 
N-2-decyltetradecyloxycarbonyl-D-glucamine; 
N-2-hexyldecyloxycarbonyl-D-glucamine; 
3-N-(2-decyltetradecyloxycarbonyl)amino!-1,2-propanediol; 
2-N-(2-decyltetradecyloxycarbonyl)amino!-2-hydroxymethyl-1,3-propanediol; 
2-N-(2-hexyldecyloxycarbonyl)amino!-1-ethanol; and 
2-N-(2-decyltetradecyloxycarbonyl)amino!-1-ethanol. 
The present invention is also directed to a process for the preparation of 
compounds of formula (I). This process comprises reacting, in a solvent, 
an aminoalcohol of formula R.sub.3 --NH--A with a compound of formula 
(II): 
##STR4## 
R.sub.1, R.sub.2, R.sub.3 and A having the same definitions as those 
provided above, and X representing a halogen atom, preferably a chlorine 
atom, or a radical derived from an azole, preferably a radical arising 
from an imidazole such as that of formula (III): 
##STR5## 
Any compatible solvent can be used in accordance with the present 
invention. Preferably the solvent is an inert solvent, meaning the solvent 
does not react with the aminoalcohol or with the compound of formula (II). 
It is possible to use, as an inert solvent, dichloromethane, 
1,2-dichloroethane, 1,1,1-trichloroethane, chloroform, acetonitrile, 
toluene, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, cyclohexane, water 
or a mixture of these solvents. 
The reaction is preferably carried out at a temperature which ranges from 
-5.degree. C. to 50.degree. C. and more preferably is less than 10.degree. 
C. 
The reaction can be carried out in the presence of a base. The base can be 
chosen from alkali metal or alkaline-earth metal hydroxides, sodium 
hydrogencarbonate, alkali metal alkoxides, alkali metal hydrides or 
tertiary amines such as pyridine or triethylamine. Sodium 
hydrogencarbonate is preferably used. 
Another subject of the present invention is a cosmetic composition 
comprising, in a cosmetically acceptable vehicle, at least one compound of 
formula (I) as defined above. More preferably, but not exclusively, the 
cosmetic composition is a hair composition. 
It is well-known that hair is sensitized or weakened to various degrees by 
the effect of atmospheric agents as well as by the repeated effect of 
various hair treatments such as permanent waves, hair straightening, 
dyeing or bleaching. The hair resultantly becomes rough to the touch and 
loses its shiny appearance. The hair is also difficult to disentangle and 
to style. It is therefore necessary, in the field of hair treatment, to 
use treatment agents in hair products with the aim of repairing the damage 
to which the hair has been subjected. These treatment agents have to 
contribute excellent properties to the hair such as disentangling, sheen, 
liveliness and a pleasant feel. 
It has now been unexpectedly and surprisingly discovered that the compounds 
of formula (I), as defined above, have excellent properties, such as, when 
used in hair compositions, they confer styling, smoothing and coating 
effects to the hair and facilitate its disentangling. The compounds of 
formula (I), as defined above, are therefore very advantageous in hair 
treatment. 
In the compositions according to the invention, the compounds of formula 
(I) are preferably present at a concentration which ranges from 0.001 to 
15% by weight, and more preferably from 0.1 to 10% by weight, with respect 
to the total weight of the composition. 
The compositions can be provided in the form of a monophase or polyphase 
aqueous or aqueous/alcoholic lotion, a monophase or polyphase gel, an 
emulsion, a cream, a vesicular dispersion, a foam, or a spray. 
The hair compositions can be provided in the form of a shampoo, a 
conditioner which is or is not to be rinsed, compositions for permanent 
waving, hair straightening, dyeing or bleaching, compositions to be 
rinsed, compositions to be applied before or after a dyeing, a permanent 
waving or a hair straightening or alternatively compositions to be applied 
between the two stages of a permanent waving or a hair straightening. 
The compositions can moreover contain conventional cosmetic additives 
chosen from fatty substances, organic solvents, silicones, thickeners, 
emollients, surface-active agents, anionic, cationic, non-ionic or 
amphoteric polymers, anti-foaming agents, hair conditioning agents such as 
proteins or vitamins, treating agents (anti-hair-loss or anti-dandruff 
agents), dyes, fragrances, preserving agents and propellants. 
More preferably, as fatty substance, use can be made of an oil, a wax or a 
mixture thereof, fatty acids, fatty alcohols, fatty acid esters such as 
C.sub.6 to C.sub.18 fatty acid triglycerides, petroleum jelly, paraffin, 
lanolin, and hydrogenated and acetylated lanolin. 
Mention may be made, among oils, of mineral, animal or vegetable oils, 
synthetic oils, and especially liquid paraffin, castor oil, jojoba oil and 
sesame oil, as well as silicon oils and gums and isoparaffins. 
Mention may be made, among waxes, of animal, vegetable, inorganic or 
synthetic waxes, and especially beeswax, candelilla wax, ozocerites, 
microcrystalline waxes and silicone waxes and resins. 
Mention may more preferably be made, among the organic solvents ordinarily 
used in cosmetic compositions, of lower C.sub.1 to C.sub.6 monoalcohols or 
polyalcohols such as ethanol, isopropanol, ethylene glycol, diethylene 
glycol, propylene glycol and glycerol. 
The thickening agents can preferably be chosen from sodium alginate, gum 
arabic, cellulose derivatives such as methyl cellulose, hydroxymethyl 
cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose and 
hydroxypropylmethyl cellulose, guar gum or its derivatives, xanthan gum, 
scleroglucans and crosslinked polyacrylic acids. 
It is possible to use, as surface-active agents and as polymers, all those 
which are well-known in the state of the art, particularly for their use 
in hair compositions. 
The compositions can be provided in the form of a vesicular dispersion of 
ionic or non-ionic amphiphilic lipids. These may preferably be prepared by 
swelling the lipids in an aqueous solution in order to form spherules 
dispersed in the aqueous medium as described in Standish & Watkins, J. 
Mol. Biol., 13, 238 (1965) and in French Patent Nos. FR-A-2,315,991 and 
FR-A-2,416,008, the disclosures of all of which are incorporated herein by 
reference. The various types of preparation processes are described in 
"Les liposomes en biologie cellulaire et pharmacologie" Liposomes in cell 
biology and pharmacology!, published by INSERM/John Libery Eurotext, 1987, 
pages 6 to 18, the disclosure of which is also incorporated herein by 
reference. 
The pH of the compositions according to the invention generally ranges from 
4 to 8 and preferably ranges from 5 to 7. 
Another subject of the invention is the use of a composition as defined 
above in hair treatment and a process for hair treatment which comprises 
applying a composition as defined above to the hair.

A number of examples demonstrating the preparation of compounds according 
to the invention and cosmetic compositions containing them will now be 
given by way of illustration and without any limiting nature. 
EXAMPLE 1 
Preparation of N-2-ethylhexyloxy-carbonyl-N-methyl-D-glucamine 
117 g (0.6 mol) of N-methyl-D-glucamine were dissolved in a reactor in a 
mixture of 800 ml of water and 400 ml of tetrahydrofuran and then 201.6 g 
(2.4 mol) of sodium hydrogencarbonate were dispersed. 
115.6 g (0.6 mol) of 2-ethylhexyl chloroformate were added dropwise, while 
maintaining the temperature of the reaction mixture at 5.degree. C., and 
then the reaction mixture was allowed to react for 3 hours with stirring 
at 5.degree. C. and overnight at rest at room temperature. 
The reaction mixture was then filtered and concentrated; the pasty residue 
obtained was dissolved in 2 liters of acetone and then filtered after 
cooling to 5.degree. C. The crystalline product collected was dried. 
105 g (yield 50%) of N-2-ethylhexyloxycarbonyl-N-methyl-D-glucamine were 
obtained. 
Melting point: 74.2.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 54.68 9.46 31.87 
3.99 
Found 54.73 9.48 31.95 
3.92 
______________________________________ 
EXAMPLE 2 
Preparation of N-2-hexyldecyloxycarbonyl-N-methyl-D-glucamine 
The compound was prepared according to the same procedure as Example 1, by 
using: 
70.2 g (0.36 mol) of N-methyl-D-glucamine dissolved in a mixture of 60 ml 
of water and 80 ml of tetrahydrofuran; 
20.96 g (1.44 mol) of sodium hydrogen-carbonate; and 
109.62 g (0.36 mol) of 2-hexyldecyl chloroformate. 
The solid residue resulting from the reaction mixture was recrystallized 
from one liter of acetone and then recrystallized a second time from 0.5 
liter of acetone. After cooling at 0.degree. C. for 12 hours, the 
crystalline product was recovered and dried. 
100 g (yield 60%) of N-2-hexyldecyloxycarbonyl-N-methyl-D-glucamine were 
obtained. 
Melting point: 70.6.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 62.17 10.65 24.16 
3.02 
Found 62.27 10.56 24.26 
3.10 
______________________________________ 
EXAMPLE 3 
Preparation of N-2-butyloctyloxycarbonyl-N-methyl-D-glucamine 
The compound was prepared according to the same procedure as Example 1, by 
using: 
78 g (0.4 mol) of N-methyl-D-glucamine; 
134.4 g (1.6 mol) of sodium bicarbonate; and 
99.4 g (0.4 mol) of 2-butyloctyl chloroformate. 
62 g of N-2-butyloctyloxycarbonyl-N-methyl-D-glucamine were obtained in the 
form of a white powder whose melting point was 77.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 58.94 10.24 3.44 27.48 
Found 59.57 10.30 3.44 27.34 
______________________________________ 
EXAMPLE 4 
Preparation of N-2-decyltetradecyloxycarbonyl-N-methyl-D-glucamine 
The compound was prepared according to the same procedure as Example 1, by 
using: 
39 g (0.2 mol) of N-methyl-D-glucamine; 
67.2 g (0.8 mol) of sodium bicarbonate; and 
83.3 g (0.2 mol) of 2-decyltetradecyl chloroformate. 
58 g of N-2-decyltetradecyloxycarbonyl-N-methyl-D-glucamine were obtained 
in the form of a white powder whose melting point was 63.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 66.74 11.38 2.43 19.45 
Found 66.49 11.41 2.65 19.67 
______________________________________ 
EXAMPLE 5 
Preparation of N-2-dodecylhexadecyloxycarbonyl-N-methyl-D-glucamine 
The compound was prepared according to the same procedure as Example 1, by 
using: 
78 g (0.4 mol) of N-methyl-D-glucamine; 
134.4 g (1.6 mol) of sodium bicarbonate; and 
189 g (0.4 mol) of 2-dodecylhexadecyl chloroformate. 
163 g of N-2-dodecylhexadecyloxycarbonyl-N-methyl-D-glucamine were obtained 
in the form of a white powder whose melting point was 54.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 68.55 11.74 2.38 17.54 
Found 68.42 11.64 2.22 17.72 
______________________________________ 
EXAMPLE 6 
Preparation of N-2-decyltetradecyloxycarbonyl-D-glucamine 
36.2 g (0.2 mol) of D-glucamine were dissolved in 100 ml of water in a 1000 
ml reactor. 135 ml of tetrahydrofuran and then 67.2 g (0.8 mol) of sodium 
bicarbonate were added. The mixture was brought to -2.degree. C. with 
stirring and then 83.3 g (0.2 mol) of 2-decyltetradecyl chloroformate were 
added dropwise over 150 minutes. At the end of the addition, the mixture 
was left for 2 hours at 0.degree. C. and was then left to progressively 
return, also over 2 hours, to 25.degree. C. The insoluble material was 
removed on sintered glass and concentration to dryness was then carried 
out with a rotary evaporator. 
The residue was recrystallized from one liter of acetone and this operation 
was repeated once from one liter of acetone and once from one liter of 
ethyl acetate/acetone mixture (1/1 vol/vol). 
61 g of N-2-decyltetradecyloxycarbonyl-D-glucamine were obtained in the 
form of a white powder whose melting point was 82.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 66.27 11.30 2.49 19.93 
Found 66.41 11.34 2.44 20.01 
______________________________________ 
EXAMPLE 7 
Preparation of N-2-hexyldecyloxycarbonyl-D-glucamine 
The compound was prepared according to the same procedure as Example 6, by 
using: 
46.8 g (0.24 mol) of D-glucamine; 
80.6 g (0.96 mol) of sodium bicarbonate; and 
73.08 g (0.24 mol) of 2-hexyldecyl chloroformate. 
70 g of N-2-hexyldecyloxycarbonyl-D-glucamine were obtained in the form of 
white powder whose melting point was 81.degree. C. 
EXAMPLE 8 
Preparation of 3-N-(2-decyltetradecyloxycarbonyl)amino!-1,2-propanediol 
The compound was prepared according to the same procedure as Example 6, by 
using: 
18.2 g (0.2 mol) of 3-amino-1,2-propanediol; 
67.2 g (0.8 mol) of sodium bicarbonate; and 
83.3 g (0.2 mol) of 2-decyltetradecyl chloroformate. 
95 g of an amber oil were obtained, which oil was purified on silica using 
dichloromethane/methanol mixtures (from 10/0 to 9/1 vol/vol). 
80 g of a white wax were obtained, the purity of which was monitored by 
thin layer chromatography (dichloromethane/methanol eluent: 95/5 vol/vol, 
R.sub.f =0.34). 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 71.29 12.18 2.97 13.57 
Found 70.88 12.29 2.87 14.07 
______________________________________ 
EXAMPLE 9 
Preparation of 
2-N-(2-decyltetradecyloxycarbonyl)amino!-2-hydroxymethyl-1,3-propanediol 
The compound was prepared according to the same procedure as Example 6, by 
using: 
24.2 g (0.2 mol) of tris(hydroxymethyl) aminomethane; 
67.2 g (0.8 mol) of sodium bicarbonate; and 
83.3 g (0.2 mol) of 2-decyltetradecyl chloroformate. 
After reaction and purification on silica (heptane/ethyl acetate eluent: 
7/3 then 6/4 vol/vol), 40 g of a white wax were obtained, the melting 
point of which was 51.degree. C. and the purity of which was verified by 
thin layer chromatography (dichloromethane/methanol: 29/1 vol/vol; R.sub.f 
=0.45) 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 69.46 11.78 2.78 15.97 
Found 69.42 11.81 2.75 15.87 
______________________________________ 
EXAMPLE 10 
Preparation of 2-N-(2-hexyldecyloxycarbonyl) amino!-1-ethanol 
1st Stage: 
105.3 g of carbonyldiimidazole (0.65 mol) were dissolved in 1200 ml of 
dichloromethane in a two liter reactor. 
133.38 g (0.55 mol) of 2-hexyldecanol were then added dropwise over 1 hour 
at 20.degree. C. The reaction mixture was left stirring for 4 hours at 
20.degree. C. The reaction mixture was poured into a separating funnel and 
washed 4 times with 200 ml of water. The organic phase was dried over 
sodium sulphate and then concentrated to dryness. 
173 g of 2-hexyldecyloxycarbonylimidazole were obtained in the form of a 
yellow oil. 
2nd Stage: 
12.2 g (0.2 mol) of aminoethanol were dissolved in 400 ml of anhydrous 
tetrahydrofuran in a 1 liter reactor. A solution of 73.9 g (0.22 mol) of 
2-hexyldecyloxy carbonylimidazole (prepared in the 1st stage) in 300 ml of 
tetrahydrofuran were added at a temperature of 20.degree. C. over 90 
minutes. 
Stirring was continued for 24 hours at 20.degree. C. and evaporation was 
then carried out to dryness. 88 g of an oil were obtained, which oil was 
dissolved in 500 ml of ethyl acetate and then washed with three times 100 
ml of water. The organic phases were combined, dried over sodium sulphate 
and evaporated to dryness. 
71 g of an amber oil were obtained, which oil was purified on silica (9/1 
then 8/2 vol/vol heptane/ethyl acetate eluent) to result in 35 g of a 
colourless oil whose purity was monitored by thin layer chromatography 
(5/5 vol/vol ethyl acetate/heptane eluent; R.sub.f =0.55). 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 69.30 11.85 4.25 14.58 
Found 69.25 11.93 4.25 14.57 
______________________________________ 
EXAMPLE 11 
Preparation of 2-(N-(2-decyltetradecyloxycarbonyl)amino!-1-ethanol 
1st Stage: 
The preparation was carried out under the same conditions as in the first 
stage of Example 10, by using: 
177 g (0.5 mol) of 2-decyltetradecanol; 
89.1 g (0.55 mol) of carbonyldiimidazole; and 
1200 ml of dichloromethane. 
230 g of 2-decyltetradecyloxycarbonylimidazole were obtained in the form of 
an amber oil. 
2nd Stage: 
The preparation was carried out under the same conditions as in the second 
stage of Example 10, by using: 
89.2 g (0.2 mol) of 2-decyltetradecyloxycarbonylimidazole; 
13.42 g (0.22 mol) of aminoethanol; and 
500 ml of tetrahydrofuran. 
73 g of a white wax were obtained, the melting point of which was 
48.degree. C. 
______________________________________ 
ELEMENTAL ANALYSIS: 
% C % H % O % N 
______________________________________ 
Calculated 73.46 12.47 3.17 10.88 
Found 72.94 12.49 3.32 10.92 
______________________________________ 
EXAMPLE 12 
Shampoo 
______________________________________ 
Alkyl (C.sub.9 /C.sub.10 /C.sub.11 -20/40/40) 
15 g AM 
poly(1-4)glucoside sold under the 
name "APG 300" by the Company Henkel 
containing 50 g % of active material 
Compound of Example 2 0.1 g 
Preserving agents q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 7 with hydrochloric acid. A clear fluid solution was 
obtained. 
EXAMPLE 13 
Shampoo 
______________________________________ 
Sodium lauryl ether carboxylate 
7.7 g AM 
(C.sub.12 /C.sub.14 70/30) oxyethylenated with 
4.5 mol of ethylene oxide as a 22% 
by weight aqueous solution sold 
under the name "Akyposoft 45 NV" by 
the Company Chemy 
Sodium lauryl ether sulphate 
8.5 g AM 
(C.sub.12 /C.sub.14 70/30) oxyethylenated with 
2.2 mol of ethylene oxide as an 82% 
by weight aqueous solution sold under 
the name "Empicol ESB/3FL" by the 
company Albright & Wilson Saint-Mihiel 
Coconut acid monoisopropanolamide 
3 g 
Ether of myristyl glycol and tallow 
0.5 g 
oxyethylenated with 60 mol of ethylene 
oxide sold under the name 
"Elfacos GT 2825" by the company Akzo 
Compound of Example 8 0.8 g 
Preserving agent q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 7 with sodium hydroxide. A clear thickened liquid 
was obtained. 
EXAMPLE 14 
Shampoo 
______________________________________ 
Sodium lauryl ether carboxylate 
15 g AM 
(C.sub.12 /C.sub.14 70/30) oxyethylenated with 
4.5 mol of ethylene oxide as a 22% 
by weight aqueous solution sold under 
the name "Akyposoft 45 NV" by the 
Company Chemy 
Sodium lauryl ether sulphate 
8 g AM 
(C.sub.12 /C.sub.14 70/30) oxyethylenated with 
2.2 mol of ethylene oxide as an 82% 
by weight aqueous solution sold under 
the name "Empicol ESB/3FL" by the 
Company Albright & Wilson Saint-Mihiel 
Coconut acid monoisopropanolamide 
2 g 
Ether of myristyl glycol and tallow 
1 g 
oxyethylenated with 60 mol of ethylene 
oxide sold under the name 
"Elfacos GT 2825" by the Company Akzo 
Compound of Example 11 0.4 g 
Preserving agent 100 g 
______________________________________ 
The pH was adjusted to 7 with sodium hydroxide. A transparent fluid gel was 
obtained. 
EXAMPLE 15 
Shampoo 
______________________________________ 
Sodium lauryl ether carboxylate 
15 g AM 
Mixture of cocoylaminopropyl betaine 
4 g AM 
and of glyceryl monolaurate (25/5) as 
a 30% by weight aqueous solution sold 
under the name "Tegobetaine HS" by the 
Company Goldschmidt 
Water/propylene glycol and polyethylene 
1.2 g AM 
glycol (containing 55 mol of ethylene oxide) 
dioleate (20/40/40) sold under the name 
"Antil 141 liquid" by the Company 
Goldschmidt 
Compound of Example 3 0.3 g 
Preserving agent q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 6.8 with sodium hydroxide. A clear thickened liquid 
was obtained. 
Hair can be shampooed with the compositions of Examples 12 to 15. After 
drying, it is believed that the hair will be smooth, shiny and easy to 
disentangle. 
EXAMPLE 16 
Conditioner 
______________________________________ 
Behenyltrimethylammonium chloride at 80% 
2 g AM 
by weight in a water/isopropanol (15/85) 
mixture sold under the name 
"Catinal DC 80" by the Company 
Toho 
Compound according to Example 4 
0.5 g 
Preserving agents q.s. 
Water q.s. for 100 g 
______________________________________ 
An opaque fluid solution was obtained. 
EXAMPLE 17 
Conditioner 
______________________________________ 
Cetyltrimethylammonium chloride as a 25% 
0.5 g AM 
by weight aqueous solution sold under 
the name "Dehyquart A" by the Company 
Henkel 
Compound of Example 5 0.5 g 
Preserving agents q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 5.5 with sodium hydroxide. 
EXAMPLE 18 
Conditioner 
______________________________________ 
Behenyltrimethylammonium chloride at 80% 
5 g AM 
by weight in a water/isopropanol (15/85) 
mixture sold under the name "Catinal DC 80" 
by the Company Toho 
Compound of Example 7 0.25 g 
Preserving agents q.s. 
Water q.s. for 100 g 
______________________________________ 
A fluid milky solution was obtained. 
The conditioners of Examples 16 to 18 can be applied to wet hair after a 
simple shampooing. After rinsing with water and then drying, it is 
believed that the hair will be smooth, lively and covered. It is also 
believed that the styling will have excellent form retention. 
EXAMPLE 19 
Non-rinsed Lotion 
______________________________________ 
Sorbitan monolaurate oxyethylenated with 
0.5 g 
20 mol of ethylene oxide 
Compound of Example 6 0.001 g 
Preserving agents q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 7 with sodium hydroxide. A clear fluid lotion was 
obtained. 
EXAMPLE 20 
Non-rinsed Lotion 
______________________________________ 
1-Methyl-2-tallow-3- 0.2 g AM 
(tallowamidoethyl) imidazolinium 
methylsulphate as a 75% by weight 
solution in propylene glycol sold under 
the name "Rewoquat W 75 PG" by the 
Company Rewo 
Compound according to Example 9 
0.005 g 
Preserving agent q.s. 
Water q.s. for 100 g 
______________________________________ 
The pH was adjusted to 5 with sodium hydroxide. An opalescent fluid lotion 
was obtained. 
The lotions of Examples 19 and 20 can be applied to wet hair after a simple 
shampooing. Without rinsing the hair, it can be dried and then styled. It 
is believed that the hair will be uniformly smooth, lively, covered and 
easy to disentangle.