Cosmetic compositions containing polymers produced in the presence of cerium ions

A cosmetic composition for application to the hair or skin comprises in an appropriate cosmetic vehicle at least one polymer produced by polymerizing an unsaturated monomer and a compound having at least one OH function, the said polymerization being carried out in an aqueous medium and in the presence of cerium ions.

The present invention relates to a cosmetic composition containing a 
particular type of polymer. These cosmetic compositions comprise, in an 
appropriate cosmetic vehicle, at least one polymer resulting from the 
polymerization of an unsaturated monomer and a compound having at least 
one OH function, the said polymerization being carried out in an aqueous 
medium in the presence of cerium ions. 
Various tests have established that the cosmetic compositions containing 
these polymers, when applied to the hair, in the form of a hair setting 
lotion or in the form of a hair lacquer, provide excellent holding power 
and render the hair soft and shiny. 
Moreover, it has been established tht these polymers, when present in other 
cosmetic formulations such as shampoos, hair rinses or conditioners or 
hair dye compositions, render the hair easy to untangle and impart thereto 
excellent brightness characteristics. 
Moreover, these polymers can be employed as a primary or secondary 
component, in milks, creams, lotions or dye foundations, for application 
to the skin or the face. Their presence in these compositions provides 
excellent cosmetic characteristics. 
These same polymers which can also advantageously replace conventional 
cosmetic resins presently employed in nail polish compositions impart 
thereto good adhesion characteristics, long lasting properties and 
excellent brightness qualities. 
In accordance with the present invention, the compound or prepolymer having 
at least one OH function can be a natural compound, modified or not, or a 
polymeric or non-polymeric synthetic compound. 
Representative natural compounds include, for instance, gelatin, cellulose, 
starch, modified starch, collagen, chitosans, nitro-cellulose, cellulose 
ethers and cellulose carrying cationic functions. 
Representative synthetic compounds include, for instance: 
(i) polymers having a polymeric hydrocarbon chain such as: polyvinyl 
alcohols; partially hydrolyzed polyvinyl acetates; copolymers of N-vinyl 
pyrrolidone and vinyl acetate, totally or partially hydrolyzed; copolymers 
of crotonic acid and vinyl acetate, totally or partially hydrolyzed; 
polyvinyl pyrrolidone (di-OH); polyacrylamide (di-OH); N-N-dimethyl 
amino-2-ethyl methacrylate quaternized with ethyl bromide (di-OH); poly 
butadiene having OH end groups, such as those known under the trade names 
of "Hycar HTB", sold by Goodrich, "NISSO PBG 2000" sold by Nippon Soda, 
"R15" sold by Sinclair Koppers, "Butarez HT" sold by Phillips Petroleum, 
and "Telagen HT" sold by General Tire; polyisobutylene having OH end 
groups such as those known under the trade name "HTPIB" sold by Enjay 
Polymer; and copolymers of N-methacryloyl D-glucosamine, such as the 
copolymers of N-vinyl pyrrolidone/N-methacryloyl D-glucosamine (di-OH or 
not); and 
(ii) polymeric compounds having a hydrocarbon chain containing heteroatoms 
such as, polyethylene glycol, polypropylene glycol, copolymer of 
polyethylene oxidepolypropylene oxide; copolymer of polyethylene 
oxidepolysiloxane or polyoxyethylenated nonyl phenols. 
Representative non-polymeric compounds include, particularly, 
pentaerythritol. 
Representative unsaturated monomers which are polymerized with the compound 
having at least one OH function include, for instance: 
(a) acrylic or methacrylic acid; 
(b) acrylic or methacrylic esters of the formula: 
##STR1## 
wherein R represents hydrogen or methyl and R.sub.1 represents linear or 
branched alkyl having from 1 to 18 carbon atoms. Representative esters 
include the acrylate or methacrylate of methyl, ethyl, propyl tert-butyl, 
octyl, dodecyl an octadecyl; 
(c) N,N-dialkylamino ethyl acrylic or methacrylic esters of the formula: 
##STR2## 
wherein R hs the same meaning given above and r' and r" each independently 
represent alkyl having from 1-5 carbon atoms. Included among these 
compounds are the acrylates or methacrylates of N,N-dimethylamino-2-ethyl 
acrylates or methacrylates or N,N-diethylamino-2-ethyl acrylates or 
methacrylates; 
(d) hydroxyalkyl acrylic or methacrylic esters of the formula: 
##STR3## 
wherein R has the same meaning given above and n is 2 or 3. Included 
among these compounds are 2-hydroxy ethyl or 3-hydroxypropyl acrylates or 
methacrylates; 
(e) acrylamide or methacrylamide; 
(f) hydroxy alkylacrylamides of the formula: 
##STR4## 
wherein R has the same meaning given above and n is 1-3. Included among 
these compounds are hydroxyethylacrylamide and hydroxypropylacrylamide; 
(g) N-alkylacrylamides and methacrylamides of the formula: 
##STR5## 
wherein R has the same meaning given above and R.sub.2 represents linear 
or branched alkyl having from 1-5 carbon atoms. Included among these 
compounds are N-methylacrylamide and N-tert-butylacrylamide; and 
(h) N,N-diallyl,N,N-dialkylammonium chlorides or bromides of the formula: 
##STR6## 
wherein R.sub.3 and R.sub.4 each independently represent linear or 
branched alkyl having from 1-16 carbon atoms and X is Cl or Br. Included 
among these compounds are N,N-diallyl-N-methyl, N-dodecylammonium chloride 
or bromide; N,N-diallyl-N-methyl-N-butylammonium chloride or bromide; 
N,N-diallyl-N-methyl-N-octylammonium chloride or bromide; and 
N,N-diallyl-N-methyl-N-decylammonium chloride or bromide. 
If the compound or prepolymer having at least one OH function is a 
homopolymer and possesses at one of its ends a single OH function, the 
polymerization in the presence of an unsaturated monomer such as those 
listed above produces a sequenced polymer and, more particularly, a 
bi-sequenced polymer. 
On the other hand, if the homopolymer possesses two OH functions, one at 
each end thereof, a tri-sequenced polymer is obtained. 
Thus, when, as the homopolymer having at least two OH functions, polyvinyl 
pyrrolidone (di-OH) is employed, polymerization of the same with methyl 
methacrylate (MAM) provides a tri-sequenced polymer which can be 
schematically represented as follows: 
##STR7## 
On the other hand, when as the compound having at least one OH function 
there is employed a copolymer having at least on one of its ends an OH 
function and also at least one lateral OH function, the polymerization in 
the presence of an unsaturated monomer provides a polymer which is both 
sequenced and graft. 
Thus, the use of a compound having OH functions of the type indicated 
above, i.e. a copolymer of N-vinyl pyrrolidone/N-methacryloyl 
D-glucosamine (di-OH) of the following formula: 
##STR8## 
provides on copolymerization with, for example, methyl methacrylate, a 
compound having on the one hand polymethylmethacrylate (PMAM) sequences at 
each end of the polymer chain and additionally PMAM grafts on one or more 
of the OH functions of the glucosamine molecule. 
In another embodiment of the present invention, the compound having at 
least one OH function can be a copolymer free of terminal OH groups, but 
having, on the contrary, at least one lateral OH function so that the 
presence of an unsaturated monomer, the polymerization provides a graft 
polymer only. 
Thus, the use of a copolymer having at least one lateral OH function, i.e. 
a polymer having the following formula formula: 
##STR9## 
provides on copolymerization with methylmethacrylate a copolymer having 
PMAM grafts on one or more of the glucosamine OH functions. 
Further, in another embodiment of the present invention, the compound 
having at least one OH function can be a non-polymeric compound, such as, 
for example, pentaerythritol, a compound which has four OH functions. The 
polymerization of this compound with an unsaturated monomer, such as 
methyl methacrylate, provides a compound having PMAM grafts on one or more 
of the OH functions. Polymers of this type are called "starred polymers". 
As will be seen from the Examples below, the proportions of reactants used 
to form the polymers in accordance with invention can vary widely, that 
is, the compound having at least one OH function may constitute from about 
15 to 95% by weight of reactants and the unsaturated monomer may comprise 
from 5 to about 85% by weight of the reactants. 
The molecular weight of the polymer utilized in the cosmetic composition of 
this invention can vary significantly, and the choice of any particular 
molecular weight can be dictated by the particular type of cosmetic 
formulation in which it is incorporated. Further, the molecular weight of 
the polymer can be dependent on the choice of the particular reactants 
employed to produce the same such as the polymeric or non-polymeric 
content of the prepolymer or compound and on the number of sequences or of 
the degree or amount of grafting desired. 
The polymers employed in accordance with the present invention, be they 
sequenced, sequenced and grafted, grafted, or starred, are prepared simply 
by reacting in an aqueous solution the compound or prepolymer having at 
least one oh function with an unsaturated monomer in the presence of an 
effective amount of cerium salt such as, for example, cerium ammonium 
nitrate [(NH.sub.4).sub.2 Ce(NO.sub.3).sub.6 ]. 
The operating conditions for this process which are known, see L. J. 
Guilbault et al, J. Macro, Sci. Chem. A7(8), P. 1.581 (1973) are as 
follows: 
The prepolymer or compound and the unsaturated monomer or monomers to be 
polymerized are placed in an aqueous solution (distilled water) in a 
reactor fitted with a stirrer and a nitrogen lead-in tube. To this 
mixture, there is introduced an amount of cerium ammonium nitrate 
sufficient to form the desired number of sequences and/or the amount or 
degree of grafting. Obviously, then the quantity of catalyst can be 
significantly varied, depending on the ultimate polymer desired for 
inclusion in a particular type cosmetic formulation. In a preferred 
manner, the cerium ammonium nitrate is introduced in solution in normal 
nitric acid. 
The resulting reaction mixture is then stirred for a time varying from 2 to 
48 hours, either at ambient temperature or at a temperature between 
40.degree. and 80.degree. C. 
After the termination of the polymerization reaction, the resulting polymer 
is then precipitated with an organic material such as, for example, ether, 
isopropyl alcohol, acetonitrile, acetone or a mixture thereof. 
Importantly, the preparation of certain prepolymers must be carried out 
under special conditions, that is, in an aqueous solution in the presence 
of H.sub.2 O.sub.2 which serves as an initiator, and with a compound such 
as borax so as to provide on the polymeric chain some terminal OH groups. 
Such is the case, for example, in the preparation of polyvinyl pyrrolidone 
(di-OH) or polyacrylamide (di-OH) or the copolymer of 
N-vinylpyrrolidone/N-methacryloyl D-glucosamine (di-OH). 
The exact structure of the desired polymers of the present invention has 
not yet been determined with exacitude since the radical formed by the 
reduction of Ce.sup.IV to Ce.sup.III in the presence of at least one OH 
function can be situated either on the oxygen of the OH or on the adjacent 
carbon. 
The cosmetic compositions of the present invention can contain the polymers 
defined above either as the principal active component, or as an additive. 
These cosmetic compositions can be provided in the form of aqueous, 
alcoholic or hydroalcoholic solutions, the alcohol being principally a 
lower alkanol such as ethanol or isopropanol, or in the form of creams, 
gels, emulsions, milks or in the form of an aerosol also containing a 
propellant, or even in the form of a nail polish. 
The adjuvants generally included in the cosmetic compositions of the 
present invention are, for example, perfumes, dyes, preservatives, 
sequesterants, thickening agents and the like. 
The cosmetic compositions of the present invention can be the ready-to-use 
type compositions or they can be concentrates which require dilution 
before use. Thus, the cosmetic compositions of the present invention need 
not be limited to any particular polymer concentration. 
Generally, however, in the cosmetic compositions of the present invention, 
the polymer is present in an amount between 0.1 and 15 weight percent 
thereof and preferably between 0.5 and 10 weight percent. 
These cosmetic compositions exhibit significantly interesting cosmetic 
properties when they are applied to the hair. Thus when they are applied 
to the hair, they substantially improve the qualities of the hair and 
facilitate untangling wet or moist hair. 
Thus, in one embodiments of the present invention, the cosmetic 
compositions are principally cosmetic compositions for the living human 
hair containing at least one polymer as described above. Further, these 
cosmetic compositions for the hair generally include at least one adjuvant 
conventionally employed in such type compositions. 
These cosmetic compositions for the hair can be provided in the form of an 
aqueous, alcoholic or hydroalcoholic solution (the alcohol being a lower 
alkanol such as ethanol or isopropanol), or in the form of a cream, a gel 
or an emulsion or even in the form of a spray. They can also be packaged 
under pressure in an aerosol container so as to form an aerosol which also 
contains a propellant, such as for example, nitrogen, nitrogen pentoxide 
or chlorofluoronated hydrocarbons of the Freon type, such as Freon 11 and 
Freon 12, or a mixture of these propellants. 
The adjuvants generally provided in the cosmetic compositions for the hair 
in accordance with the present invention can be, for example, perfumes, 
dyes, preservatives, sequesterants, thickening agents and emulsifying 
agents. 
The polymers can be provided, in the cosmetic compositions for the hair of 
this invention, either as an additive, or as the principal active 
component in hair setting lotions, in hair treating lotions, in hair 
styling creams or gels, or as an additive in shampoos, hair setting 
lotions, permanent waving formulations, hair restructuring agents, hair 
treating lotions or hair lacquer compositions. 
The cosmetic compositions for the hair of the present invention are then 
principally: 
(a) hair treating or lotion compositions comprising, as the active 
component, at least one polymer according to the invention in an aqueous 
or hydroalcoholic solution. The amount of polymer can vary between 0.1 to 
10% by weight and preferably between 0.1 and 5% by weight. 
The pH of these lotions is close to neutral and can vary for example from 6 
to 8. If necessary, the pH can be adjusted to the desired value, by adding 
either an acid such as citric acid or a base, principally an alkanolamine 
such as monoethanolamine or triethanolamine. 
To treat the hair with such a lotion, the same is applied to damp hair and 
is permitted to remain in contact therewith for 3 to 15 minutes. 
Thereafter the hair is thoroughly rinsed, and if desired, set in a 
conventional manner; 
(b) a shampoo composition comprising at least one polymer according to the 
invention and a cationic, non-ionic or anionic detergent. 
Representative cationic detergents include, principally, long chain 
quaternary ammoniums, esters of fatty acids and amino alcohols or amine 
polyethers. 
Representative non-ionic detergents include, principally, esters of polyols 
and sugars, the condensation products of ethylene oxide on fatty bodies, 
on long chain alkyl phenols, on long chain mercaptans or on long chain 
amides and the polyhydroxylated polyethers or fatty alcohols. 
Representative anionic detergents include, principally, alkaline salts, 
ammonium salts or salts of amines or of amino alcohols with fatty acids 
such as oleic acid, ricinoleic acid, copra oil acid, hydrogenated copra 
oil acid, alkaline salts, ammonium salts or salts of amino alcohols and 
the sulfates of fatty alcohols, principally C.sub.12 -C.sub.14 and 
C.sub.16 fatty alcohols; alkaline salts, magnesium salts, ammonium salts 
or amino alcohol salts of the sulfates of oxyethylenated fatty alcohols; 
the condensation products of fatty acids with isethionates, taurine, 
methyl taurine, or sarcosine etc; the alkylbenzenesulfonates, notably 
those wherein the alkyl moiety has 12 carbon atoms; the alkylarylpolyether 
sulfates and monoglyceride sulfates. All these anionic detergents, as well 
as numerous others not cited here, are well kwown and are described in the 
literature. 
The shampoo composition of the present invention can also contain various 
adjuvants, for example, perfumes, dyes, preservatives, thickening agents, 
foam stabilizers, softening agents or other cosmetic resins. In these 
shampoo compositions, the concentration of the detergent is generally 
between 5 and 50 percent by weight and the polymer concentration is 
between 0.1 and 10 weight percent and preferably between 0.1 and 5 weight 
percent of said composition; 
(c) a hair setting lotion, notably for sensitized hair, comprising at least 
one polymer of this invention, in aqueous, alcoholic or hydroalcoholic 
solution. These compositions can also contain other cosmetic resins. The 
polymer concentration in these hair setting lotions can vary generally 
between 0.1 and 5 weight percent and, preferably, between 0.2 to 3 weight 
percent thereof. The pH of these hair setting lotions can range generally 
between 3 and 9 and preferably between 4.5 and 7.5. The pH, if desired, 
can be adjusted for example by adding an alkanolamine such as 
monoethanolamine or triethanolamine; 
(d) hair dye compositions comprising at least one polymer according to the 
invention, a dye agent and an appropriate vehicle. Preferably, the vehicle 
chosen is one which provides the composition in cream form. The 
concentration of the polymer in these hair dye compositions can vary 
between 0.5 and 15 weight percent, and preferably between 0.5 and 10 
weight percent thereof. 
When an oxidation dye is employed, the dye composition can be packaged in 
two parts, one part containing H.sub.2 O.sub.2 and the other part the 
remaining components. The two parts are admixed at the time of use; and 
(e) hair lacquer compositions comprising an alcoholic or hydroalcoholic 
solution of at least one polymer of the present invention, this solution 
being packaged in an aerosol container under pressure together with a 
conventional aerosol propellant. 
The aerosol lacquer according to the present invention can be prepared by 
adding the polymer of the invention to a mixture of an anhydrous aliphatic 
alcohol such as ethanol or isopropanol and a propellant or a mixture of 
liquified propellants such as halogenated hydrocarbons, of the 
trichlorofluoromethane or dichlorodifluoromethane type or their mixtures. 
In these hair lacquer compositions, the polymer concentration generally 
ranges between 0.1 and 3 weight percent thereof. It is also permissible to 
add to these hair lacquer compositions such adjuvants as dyes, 
plasticizers or any other conventional adjuvant. 
The polymers of the present invention also exhibit interesting cosmetic 
characteristics when they are applied to the skin. Principally they favor 
the hydration of the skin, and thus avoid its drying out. Further, they 
impart to the skin a significant softness to the touch characteristic. 
Thus, the cosmetic compositions of the present invention can be cosmetic 
compositions for the skin which include at least one polymer according to 
the invention. Further, these compositions can contain at least one 
adjuvant conventionally employed in cosmetic compositions for the skin and 
can be provided, for example, in the form of creams, gels, emulsions or as 
an aqueous, alcoholic or hydroalcoholic solution. 
The polymer concentration in these compositions for the skin can vary 
generally between 0.1 and 10 weight percent thereof. 
The adjuvants generally present in these cosmetic compositions are for 
example perfumes, dyes, preservatives, thickening agents, sequesterants, 
emulsifying agents and the like. 
These compositions for the skin constitute, principally, creams or treating 
lotions for the hands or face, anti-solar creams, dye foundation creams 
and make-up remover milks and can be prepared in accordance with 
conventional procedures. 
For example, to obtain a cream, an aqueous phase containing in solution the 
polymer of the present invention and optionally other components or 
adjuvants is emulsified with an oily phase. 
Representative oily phases can include, for instance, paraffin oil, 
petrolatum oil, sweet almond oil, avocado oil, olive oil, esters of fatty 
acids such as glyceryl monostearate, ethyl or isopropyl palmitate and 
alkyl myristates such as propyl, butyl or cetyl myristate. Further fatty 
alcohols such as cetyl alcohol or waxes such as beeswax can also be 
included. 
The compositions according to the present invention can also be provided in 
the form of nail polish and contain preferably from 3 to 15 percent by 
weight of the polymer of the present invention in combination with a 
plasticizing agent, a film forming agent and a solvent system, i.e. 
conventional solvents and/or diluents for this type of composition. The 
solvent system comprises from 60 to 80 weight percent of the nail polish 
composition. In certain cases these nail polish compositions can also 
contain a dye in an amount ranging from 0.05 to 6 percent by weight 
relative to the total weight of the nail polish composition. 
The nail polish composition of the present invention provides excellent 
brightness and durability.

The following non-limiting examples illustrate the preparation of the 
polymers and the cosmetic compositions of the present invention. 
EXAMPLES OF PREPOLYMER PREATION 
EXAMPLE 1 
Preparation of polyvinylpyrrolidone prepolymer containing an OH function at 
each end of the chain thereof 
Into a 1 liter round bottom flask, 100 g of freshly distilled 
N-vinyl-pyrrolidone, 500 g of distilled water and 1.5 g of borax (Na.sub.2 
B.sub.4 O.sub.7.10H.sub.2 O).sub.n are introduced. The resulting reaction 
mixture is heated with stirring to 40.degree. C. under a current of 
nitrogen. 
After dissolution of the borax, 1 ml of H.sub.2 O.sub.2 (110 volumes) is 
added to the reaction mixture and the temperature thereof is maintained at 
40.degree. C. for 7 hours. The resulting polymer is precipitated in 
acetone and dried under reduced pressure, yielding 99 g of pure polymer 
having a viscosity of 4.5 cpo at 34.6.degree. C. in a 5% solution in 
water. 
EXAMPLE 2 
Preparation of N-vinylpyrrolidone/N-methacryloyl D-glucosamine prepolymer 
Into a 500 ml round bottom flask fitted with a stirrer and a nitrogen 
lead-in tube, 100 g of ethanol, 95 g of distilled N-vinylpyrrolidone, 5 g 
of N-methacryloyl D-glucosamine and 1 g of azo-bisisobutyronitrile are 
introduced. 
The resulting mixture is heated to 80.degree. C. for 16 hours and the 
resulting polymer which is precipitated in acetone for a 60% yield, has a 
viscosity of 1.8 cpo at 34.6.degree. C. in a 5% solution in water. 
EXAMPLE 3 
Preparation of partially hydrolyzed N-vinylpyrrolidone/vinyl acetate 
prepolymer 
Into a 2 liter round bottom flask 800 ml of ethanol, 12.8 g of sodium 
hydroxide pellets and 80 g of a copolymer composed of 70% 
N-vinylpyrrolidone and 30% vinyl acetate are introduced. The resulting 
reaction mixture is maintained with stirring at 30.degree. C. for 2 hours 
and is then poured into 8 liters of diethyl ether to precipitate the 
desired polymer. After filtration the polymer is dried under reduced 
pressure. Yield: 95%. 
EXAMPLE 4 
Preparation of a partially hydrolyzed crotonic acid/vinyl acetate 
prepolymer 
The procedures of Example 3 are repeated except that there is employed a 
90% vinyl acetate-10% crotonic acid copolymer. Yield: 95%. 
EXAMPLES 5-12 
Table I below illustrates the preparation of other prepolymers prepared in 
accordance with the method of Examples 1 or 2 above. 
TABLE I 
__________________________________________________________________________ 
Ex- A- H.sub.2 O.sub.2 
Borax Temperature 
Duration Viscosity 
ample mount 
AIBN 
110 vol 
(g) Water 
Eth- 
of Reaction 
of Reaction Yield 
(cPo) 
No. Monomer (g) [a] (ml) 
[b] [c] 
(ml) 
anol 
(C..degree.) 
(hours) 
Precipitant 
(%) [d] 
__________________________________________________________________________ 
5 N-vinyl 100 5 2.5 100 40 7 acetone 
99 1.9 
pyrrolidone 
(di-OH) 
6 N-vinyl 100 20 2 80 40 6 acetone 
98 2.07 
pyrrolidone 
(di-OH) 
7 N-vinyl 1000 50 10 1000 40 7 acetone 
90 1.42 
pyrrolidone 
(di-OH) 
8 N-vinyl 100 2 1 100 40 6 acetone 
95 2.28 
pyrrolidone 
(di-OH) 
9 N-vinyl 100 10 4 500 40 24 acetone 
80 3.95 
pyrrolidone 
(di-OH) 
10 N,N-dimethyl 
100 10 4 500 40 24 ethanol 
70 2.0 
2-amino-ethyl 
methacrylate 
(di-OH), 
quaternized 
with ethyl 
bromide 
11 N-vinyl 90 
pyrrolidone/ 
1 100 
80 16 acetone 
70 1.85 
N-methacryloyl 
10 
D-glucosamine 
12 N-vinyl 80 
pyrrolidone/ 
N-methacryloyl 
1 500 40 16 acetone 
60 
D-glucosamine 
(di-OH) 20 
__________________________________________________________________________ 
[a] Azobisisobutyronitrile 
[b] Na.sub.2 B.sub.4 O.sub.7 . 10H.sub.2 O 
[c] The pH is maintained greater than 9 during the polymerization by the 
supplemental additions of borax. 
[d] In a 5% solution in water at 34.6.degree. C. 
Preparation of Polymers--all the initial reactants employed are purified. 
Preparation of the Catalyst 
The solution of cerium ammonium nitrate (CAN) is prepared by dissolving 
58.5 g of cerium ammonium nitrate in a 1 N nitric acid solution and adding 
a sufficient amount of said nitric acid solution to make 1 liter. 
EXAMPLE 13 
Preparation of a trisequenced copolymer of polymethyl methacrylate/poly 
N-vinylpyrrolidone/polymethyl methacrylate (PMAM-PVP-PMAM) 
Into a 2 liter round bottom flask fitted with a stirrer and a nitrogen 
lead-in tube, 1250 ml of distilled water and 95 g of polyvinylpyrrolidone 
(di-OH) prepared in accordance with Example 1 are introduced. There are 
then introduced 5 g of distilled methyl methacrylate and 50 ml of a 
solution of cerium ammonium nitrate in nitric acid. The reaction mixture 
is maintained with stirring for 4 hours at ambient temperature after which 
it is poured into an ethyl ether-isopropanol mixture. The resulting 
polymer which precipitates is recovered, dissolved in dimethyl formamide 
and reprecipitated in sulfuric ether. Yield: 70%. 
EXAMPLE 14 
Preparation of a sequenced and graft 50:50 copolymer of polyvinyl 
alcohol--N,N-dimethyl-2-aminoethyl polymethacrylate quaternized with 
dimethyl sulfate 
Into a 2 liter round bottom flask fitted with a stirrer and a nitrogen 
lead-in tube, 670 ml of water and 50 g of polyvinyl alcohol sold by 
Prolabo under the trade name Rhodovial A/125P are introduced. The 
resulting mixture is heated with stirring to 80.degree. C. until the 
polyvinyl alcohol is completely dissolved. The reaction mixture is then 
cooled to 20.degree. C. and there are introduced therein 50 g of 
N,N-dimethyl 2-amino ethyl methacrylate quaternized with dimethyl sulfate 
and 50 ml of a solution of cerium ammonium nitrate in nitric acid. 
The reaction mixture is maintained with stirring for 16 hours at ambient 
temperature after which the polymer is precipitated in a 3:2 mixture of 
acetone and isopropanol. The resulting polymer is then filtered and dried 
under reduced pressure. Yield: 98%. 
EXAMPLE 15 
Preparation of a sequenced and graft, 50/50 copolymer of polyvinyl alcohol 
and N-vinyl pyrrolidone 
The procedures of Example 14 are repeated except that 50 g of distilled 
N-vinylpyrrolidone are polymerized with 50 g of polyvinyl alcohol over a 
16 hour period. The resulting polymer is precipitated in a 3/2 
acetone/isopropanol mixture. 
EXAMPLE 16 
Preparation of a trisequenced copolymer by cyclopolymerization of 
N,N-diallyl-N,N-dimethyl ammonium bromide with poly-N-vinylpyrrolidone 
(di-OH) 
Into a 500 ml round bottom flask fitted with a stirrer and a nitrogen 
lead-in tube, 500 ml of distilled water and 25 g of polyvinylpyrrolidone 
(di-OH) prepared according to Example 1 are introduced. To the resulting 
mixture there are added 25 g of N,N-diallyl, N,N-dimethyl ammonium bromide 
and 25 ml of a solution of cerium ammonium nitrate in nitric acid. The 
resulting mixture which is maintained with stirring at 40.degree. C. for 
48 hours is then poured into acetonitrile. The precipitated polymer is 
recovered and dried under reduced pressure, providing 15 g of pure 
polymer. Yield: 30%. 
EXAMPLE 17 
Preparation of a trisequenced copolymer by cyclopolymerization of 
N,N-diallyl-N-dodecyl-N-methyl ammonium bromide with poly 
N-vinylpyrrolidone (di-OH) 
The procedures of Example 16 are repeated except that 25 g of N,N-diallyl 
N-dodecyl N-methyl ammonium bromide are polymerized with 25 g of poly 
N-vinylpyrrolidone (di-OH). The resulting polymer is precipitated in 
acetonitrile and recovered therefrom, providing 10 g of pure polymer. 
Yield: 20%. 
EXAMPLES 18 to 52 (see Table II below) 
TABLE II 
__________________________________________________________________________ 
Ex- Form of 
Nature of the 
A- Temperature 
Duration 
ample 
the Polymer 
Prepolymers 
mount 
H.sub.2 O 
NAC of Reaction 
of Reaction 
Yield of the 
No. Obtained 
and the Monomers 
(g) (ml) 
(ml) 
(C..degree.) 
(hours) 
Polymerization 
Precipitant 
__________________________________________________________________________ 
Prepolymer 9 
18 sequence 
of Example 8 125 5 30 31/2 acetonitrile 
Methyl methacrylate 
1 
Prepolymer 5 
19 sequence 
of Example 6 125 5 30 24 ethyl ether 
N,N-dimethylamino- 
5 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Prepolymer 9 
20 sequence 
of Example 6 125 5 30 24 ethyl ether 
N,N-dimethylamino- 
1 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Prepolymer 9 1/1 mixture of 
21 sequence 
of Example 8 125 5 30 16 ethyl ether/ 
Acrylic acid 
1 isopropanol 
Prepolymer 5 
22 sequence 
of Example 6 125 5 30 16 ethyl ether 
Acrylamide 5 
Prepolymer 8 1/1 mixture of 
23 sequence 
of Example 8 125 5 30 24 ethyl ether/ 
Acrylamide 2 isopropanol 
Prepolymer 150 
24 sequence 
of Example 8 2700 
150 40 48 45 acetonitrile 
N,N-diallyl 
150 
N,N-dimethyl 
ammonium bromide 
Prepolymer 50 
25 sequence 
of Example 7 900 50 40 18 75 acetone 
Lauryl methacrylate 
50 
Prepolymer 50 
26 sequence 
of Example 9 1100 
50 40 24 90 acetone 
N,N-dimethylamino- 
50 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Prepolymer 9 
27 sequence 
of Example 10 125 5 30 4 acetone 
Methyl methacrylate 
1 
Prepolymer 8 
28 sequence 
of Example 2 125 5 30 24 80 acetone 
Methyl methacrylate 
2 
Prepolymer 9 
29 sequence 
of Example 11 125 5 30 24 85 acetone 
Acrylamide 1 
Prepolymer 8 
30 sequence 
of Example 12 125 5 30 60 80 acetone 
and graft 
Methyl methacrylate 
2 
Polyvinyl alcohol 
20 3/2 mixture 
31 sequence 
(Rhodoviol 4/125 P) 
670 50 25 16 98 of acetone/ 
and graft 
N,N-dimethylamino- 
80 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Polyvinyl alcohol 
20 3/2 mixture 
32 sequence 
(Rhodoviol 4/125 P) 
670 50 25 16 70 of acetone/ 
and graft 
N,N-dimethylamino- 
80 isopropanol 
2-ethyl methacrylate 
quaternized with 
dimethyl sulfate 
Polyvinyl alcohol 
15 
33 sequence 
(Rhodoviol 4/125 P) 
200 12 25 4 60 acetone 
and graft 
Acrylamide 15 
Polyethylene glycol 
50 
34 sequence 
(MW = 20,000) 900 50 30 48 20 acetone 
N,N-dimethylamino- 
50 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Pentacrythritol 
14 
35 starred 
N,N-dimethylamino- 
900 10 30 48 45 acetone 
2-ethyl methacrylate 
80 
quaternized with 
ethyl bromide 
Methyl cellulose 
35 
36 sequence 
(Methocel A-15) 
900 30 30 24 40 heptane/ 
and graft 
N,N-dimethylamino- 
115 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Methylhydroxy- 
35 
propylcellulose 
37 sequence 
(Pharmacoat 603) 
900 30 30 24 40 heptane/ 
and graft 
N,N-dimethylamino- 
115 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Hydroxyethyl- 
35 
cellulose 
38 sequence 
(Cellosize WP-09) 
900 30 30 24 40 heptane/ 
and graft 
N,N-dimethylamino- 
115 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Methylhydroxy- 
35 
butylcellulose 
39 sequence 
(Methocel HB) 900 30 30 24 40 heptane/ 
and graft 
N,N-dimethylamino- 
115 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Methylhydroxy- 
80 
propylcellulose 
40 sequence 
(Pharmacoat 603) 
750 37.5 
30 24 40 ethyl ether/ 
and graft 
Acrylamide 70 isopropanol 
Methylcellulose 
80 
41 sequence 
(Methocel A-15) 
1150 
37.5 
30 24 65 ethyl ether/ 
and graft 
Acrylamide 70 isopropanol 
Methylhydroxy- 
13 
butylcellulose 
42 sequence 
(Methocel HB) 350 6.25 
30 24 20 ethyl ether/ 
and graft 
Acrylamide 12 isopropanol 
Carboxymethyl 
80 
cellulose 
43 sequence 
(Finn Fix 300) 750 37.5 
30 24 95 ethyl ether/ 
and graft 
Acrylamide 70 isopropanol 
Hydroxyethyl- 
80 
cellulose 
44 sequence 
(Cellosize WP-09) 
1150 
37.5 
30 24 90 ethyl ether/ 
and graft 
Acrylamide 70 isopropanol 
Collagen 1 
45 sequence 
(C-1633 type IV) 
10 0.5 30 24 40 acetone 
and graft 
N,N-dimethylamino- 
1 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
46 sequence 
Gelatin (ASF) 
5 125 5 40 24 50 ethyl ether/ 
and graft 
N,N-dimethylamino- 
5 +25 isopropanol 
2-ethyl methacrylate 
ml 
quaternized with 
EtOH 
ethyl bromide 
Prepolymer 29 
47 sequence 
of Example 3 450 30 30 24 30 acetone/ 
and graft 
N,N-dimethylamino- 
30 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
Prepolymer 30 
48 sequence 
of Example 4 450 30 30 48 35 ethyl ether/ 
and graft 
N,N-dimethylamino- 
30 isopropanol 
2-ethyl methacrylate 
quaternized with 
ethyl bromide 
49 sequence 
Gelatin (ASF) 
30 450 30 30 48 35 acetone 
and graft 
Methyl methacrylate 
30 
Methylhydroxy- 
70 
butylcellulose 
50 sequence 
(Methocel HB) 850 25 30 24 30 acetone 
and graft 
Hexyl methacrylate 
30 
Methylhydroxy- 
9 
butylcellulose 
51 sequence 
(Methocel HB) 350 6.25 
30 48 25 ethyl ether/ 
and graft 
N-tertiobutyl 
1 isopropanol 
acrylamide 
Prepolymer 9 
52 sequence 
of Example 4 125 5 30 48 20 ethyl ether 
N-tertiobutyl 
1 
acrylamide 
__________________________________________________________________________ 
In the polymerizations of the foregoing Examples, the amount of the 
compound having at least one OH function which was polymerized with the 
unsaturated monomer ranged from about 15 to 95 percent by weight based on 
the combined weight of the compound having at least one OH function and 
the unsaturated monomer. The amount of unsaturated monomer in the 
foregoing polymerization was from 5 to about 85% by weight, based on the 
combined weight of unsaturated monomer and the compound having at least 
one OH function. 
EXAMPLES OF PREING COSMETIC COMPOSITIONS 
EXAMPLE A 
A hair setting lotion is prepared by admixing the following components: 
Polymer of Example 13: 2 g 
Perfume: 0.1 g 
Ethyl Alcohol: 50 g 
Water, q.s.p.: 100 g 
This hair setting lotion when applied in a conventional manner to the hair 
imparts thereto a shiny appearance. The resulting hair set exhibits 
excellent holding characteristics. 
This example is repeated except that the polymer of Example 13 is replaced 
by the same amount of any one of the polymers of Examples 14-16 and 25-30. 
EXAMPLE B 
A hair setting lotion is prepared by admixing the following components: 
Polymer of Example 32: 3.5 g 
Perfume: 0.1 g 
Dye, sufficient to color the lotion: 0.2 g 
Isopropyl alcohol: 50 g 
Water, q.s.p.: 100 g 
After impregnating the hair with lotion of this example, the hair is rolled 
up on hair setting rollers, having a diameter of 15-30 mm, and then dried 
by an external source of heat. After removing the rollers, an excellent 
setting with very good holding properties is obtained. 
This example is repeated except that the polymer of Example 32 is replaced 
with the same amount of any one of the polymers of Examples 15 and 33-43. 
Equally favorable results are achieved in each instance. 
EXAMPLE C 
A hair setting lotion is prepared by admixing the following components: 
Polymer of Example 28: 3 g 
Ethyl alcohol: 50 g 
Perfume: 0.2 g 
Water, q.s.p.: 100 g 
This example is repeated except that the 3 g of the polymer of Example 28 
is replaced by the same amount of one of the copolymers of Example 16, 17 
and 43-52. 
EXAMPLE D 
An aerosol hair lacquer composition is prepared by admixing the following 
components: 
Polymer of Example 13: 8 g 
Perfume: 0.2 g 
Absolute ethyl alcohol, q.s.p.: 100 g 
25 g of this solution are then packaged in an aerosol container under 
pressure together with 47 g of trichlorofluoromethane and 28 g of 
dichlorodifluoromethane. 
After spraying the resulting lacquer on the hair, the hair is shiny, soft 
to the touch and the resin is easily removed by brushing. 
This example is repeated except that the polymer of Example 13 is replaced 
by the same amount of one of the polymers of Examples 18, 22 and 23. 
Equally favorable results are achieved. 
EXAMPLE E 
An aerosol hair lacquer composition is prepared by admixing the following 
components: 
Polymer of Example 28: 7.2 g 
Perfume: 0.3 g 
Isopropyl alcohol, q.s.p.: 100 g 
25 g of this solution are packaged in an aerosol container under pressure 
together with 47 g of trichlorofluoromethane and 28 g of 
dichlorodifluoromethane. 
After spraying the above composition on the hair, the hair is shiny and 
soft to the touch. 
This example is repeated except that the polymer of Example 28 is replaced 
by the same amount of one of the polymers of Examples 22, 23 and 24. 
Equally favorable results are achieved. 
EXAMPLE F 
A film forming body milk is prepared by admixing the following components: 
Di-ethyl hexyl adipate: 4.8 g 
Stearic acid: 2.9 g 
Lanolin alcohol oxyethylenated with 5 moles of ethylene oxide: 0.5 g 
Cetyl alcohol: 0.4 g 
Glycerol stearate: 1.0 g 
Triethanolamine: 0.95 g 
Propylene glycol: 4.8 g 
Polymer of Example 14: 0.5 g 
Preservative, an effective amount 
Perfume, an effective amount 
Sterile, demineralized water, q.s.p.: 100 g 
This example is repeated except that the polymer of Example 14 is replaced 
by the same amount of any one of the polymers of Examples 15-20 and 33-43. 
EXAMPLE G 
A film-forming skin cream is prepared by admixing the following components: 
Paraffin oil: 30.0 g 
Stearic acid: 8.0 g 
Triethanolamine: 1.0 g 
Polymer of Example 32: 0.5 g 
Preservative, an effective amount 
Perfume, an effective amount 
Sterile demineralized water, q.s.p. 100 g 
This example is repeated except that the polymer of Example 32 is replaced 
by the same amount of any one of the polymers of Examples 44-52 or 
Examples 13-20. 
EXAMPLE H 
A lotion for the skin is prepared by admixing the following components: 
Polymer of Example 32: 1.0 g 
Propylene glycol: 2.0 g 
Ethanol: 10.0 g 
Methyl parahydroxybenzoate: 0.2 g 
Perfume, an effective amount 
Dye, an effective amount to color the lotion 
Sterile, demineralized water, q.s.p. 100 g 
Initially the polymer of Example 32 is dissolved in an aqueous solution of 
the preservative (all of the water and the preservative) at 60.degree. C. 
Thereafter the solution is cooled and the remaining components are added 
thereto with moderate stirring. 
This example is repeated except that the polymer of Example 32 is replaced 
by the same amount of any one of the polymers of Examples 13, 18-24, 26-31 
and 33-48. 
EXAMPLE I 
A beauty mask composition is prepared by admixing the following components: 
Polymer of Example 14: 20.0 g 
Propylene glycol: 5.0 g 
Methyl parahydroxybenzoate: 0.2 g 
Ethanol: 15.0 g 
Kaolin: 10.0 g 
Titanium oxide: 0.5 g 
Triethanolamine lauryl sulfate: 6.0 g 
Perfume, an effective amount 
Sterile, demineralized water: 100 g 
Initially the polymer of Example 14 is dissolved in an aqueous solution of 
the preservative (all of the water and the preservative) at 60.degree. C. 
Thereafter the solution is cooled and the remaining components are added 
thereto with moderate stirring. 
This example is repeated except that the polymer of Example 14 is replaced 
by the same amount of any one of the polymers of Examples 15-20 and 44-52. 
EXAMPLE J 
A dye foundation composition is prepared by admixing the following 
components: 
______________________________________ 
Partial glyceride of 
fatty acid 9.00 g 
Cetyl stearyl alcohol 
ethoxylated with 10 moles 
of ethylene oxide 4.00 g 
Paraffin oil 18.00 g 
Polymer of Example 14 1.00 g 
Magnesium and aluminum 
silicates 0.75 g 
Rhodorsil (anti-foaming 
agent) 0.20 g 
Alkyl parahydroxybenzoate 
0.20 g 
Water, permuted 66.85 g 
Dyes, mineral 5.00 g 
105.00 g 
______________________________________ 
This example is repeated except that the polymer of Example 14 is replaced 
by the same amount of any one of the polymers of Examples 27-37 and 43-52. 
EXAMPLE K 
A dye foundation composition is prepared by admixing the following 
components: 
______________________________________ 
Partial glyceride of 
fatty acid 9.00 g 
Cetylstearyl alcohol 
ethoxylated with 10 moles 
of ethylene oxide 4.00 g 
Paraffin oil 18.00 g 
Polymer of Example 32 1.00 g 
Magnesium and aluminum 
silicates 0.75 g 
Propyl parahydroxybenzoate 
0.20 g 
Water, permuted 66.85 g 
Mineral dyes 5.00 g 
105.00 g 
______________________________________ 
This example is repeated except that the polymer of Example 32 is replaced 
by the same amount of any one of the polymers of Examples 18-26 and 38-42. 
EXAMPLE L 
A hair rinse or conditioner composition in the form of a fluid emulsion is 
prepared by admixing the following components: 
Petrolatum oil: 9.5 g 
C.sub.16 -C.sub.18 fatty alcohols polyglycerolated with 2-6 moles of 
glycerol: 6.5 g 
Polymer of Example 18: 1.5 g 
Water, q.s.p.: 100 g 
This product is applied to previously washed and dried hair by carefully 
distributing it on all of the hair and slightly massaging it therethrough. 
The composition is then permitted to remain in contact with the hair for 
about 2 minutes. Thereafter the hair is carefully rinsed and it exhibits a 
shiny luster and is easily untangled. 
This example is repeated except that the polymer of Example 18 is replaced 
by the same quantity of any one of the polymers of Examples 28-35 and 
38-43. Equally favorable results are achieved. 
EXAMPLE M 
A hair rinse composition in the form of a gel is prepared by admixing the 
following components: 
Hydroxyethyl cellulose: 0.9 g 
Polymer of Example 36: 0.8 g 
Cetyl pyridinium chloride: 3 g 
Dye, sufficient to color the gel: 0.1 g 
Water, q.s.p.: 100 g 
This gel composition is applied to washed and dried hair by slightly 
massaging it therethrough. The composition is permitted to remain in 
contact with the hair for about 1-2 minutes. Thereafter the hair is 
carefully rinsed and the hair thus treated is shiny and is easily 
untangled. 
This example is repeated except that the polymer of Example 36 is replaced 
by the same amount of any one of the polymers of Examples 45-52. Equally 
advantageous results are achieved. 
EXAMPLE N 
An anionic shampoo composition is prepared by admixing the following 
components: 
Triethanolamine lauryl myristyl sulfate: 12 g 
Copra diethanolamide: 2 g 
Dimethylamine myristyl oxide: 1.5 g 
Polymer of Example 20: 1.5 g 
Lactic acid, q.s.p. pH=6.5 
Water, q.s.p.: 100 g 
This shampoo exhibits excellent cosmetic properties. After its application 
to the hair and removal by rinsing, the wet hair untangles very easily and 
the hair, after drying, it shiny, soft and flexible. 
This example is repeated except that the polymer of Example 20 is replaced 
by the same amount of any one of the polymers of Examples 21, 22, 24, 30, 
41, 43 and 44. Equally favorable results are achieved. 
EXAMPLE O 
A cationic shampoo composition is prepared by admixing the following 
components: 
Cetyl trimethyl ammonium bromide: 2 g 
Lauryl alcohol polyglycerolated with 4 moles of glycerol: 12 g 
Polymer of Example 16: 1 g 
Perfume: 0.2 g 
Lactic acid, q.s.p. pH=4.5 
Water, q.s.p.: 100 ml 
This shampoo when applied to the hair provides a soft and aerated foam and 
provides very easy untangling of wet hair. After drying, the hair is soft, 
very bright and exhibits a light appearance. 
This example is repeated except that the polymer of Example 16 is replaced 
by the same amount of any one of the polymers of Examples 21-25 and 32-36. 
EXAMPLE P 
A non-ionic shampoo composition is prepared by admixing the following 
components: 
C.sub.11 -C.sub.14 diol polyglycerolated with 3-4 moles of glycerol: 17 g 
Polymer of Example 40: 2 g 
Cetyl pyridinium chloride: 0.8 g 
Lauryl diethanolamine: 2.5 g 
Perfume: 0.2 g 
Lactic acid, q.s.p. pH=5.5 
Water, q.s.p.: 100 ml 
This clear shampoo composition provides a sufficiently soft abundant foam 
and provides for easy untangling of wet hair, dyed or bleached. After 
drying the hair is soft, light and shiny. 
This example is repeated except that the polymer of Example 40 is replaced 
by the same amount of any one of the polymers of Examples 41, 43 and 44. 
EXAMPLE Q 
A hair dye composition in the form of a gellable liquid is prepared as 
follows: 
A hair dye base is prepared by admixing the following components: 
Oleyl alcohol glycerolated with 2 moles of glycerol: 20 g 
Oleyl alcohol glycerolated with 4 moles of glycerol: 20 g 
Butyl glycol: 8 g 
Propylene glycol: 12 g 
Ammonia (22.degree. Be): 10 ml 
Para-aminophenol base: 0.08 g 
Meta-diaminoanisol sulfate: 0.025 g 
Resorcin: 0.3 g 
Meta-aminophenol base: 0.06 g 
Nitro paraphenylene diamine: 0.003 g 
Paratoluylene diamine: 1.05 g 
Hydroquinone: 0.17 g 
Ethylene diamine tetraacetic acid: 3 g 
Sodium bisulfite (d=1.32): 0.8 g 
Water, q.s.p.: 100 g 
To 50 g of the above hair dye base there are mixed at the moment of use 5 g 
of a 35% solution of the polymer of Example 29 and 50 g of H.sub.2 O.sub.2 
(20 volumes). 
The resulting composition is then applied to the hair with the aid of a 
brush and is permitted to remain in contact therewith for 30 minutes. 
Thereafter, the hair is thoroughly rinsed. The wet hair is easily 
untangled and when dried it has a soft feel or touch, is shiny and has 
body. On deep chestnut hair, a light chestnut coloration is achieved. 
This example is repeated except that the polymer of Example 29 is replaced 
by an equivalent amount of any one of the polymers of Examples 16, 19-21, 
23, 24, 26 and 35. 
EXAMPLE R 
An essentially colorless nail lacquer composition is prepared by admixing 
the following components: 
______________________________________ 
Nitrocellulose, RS 1/2 
second viscosity 16 g 
Polymer of Example 50 6 g 
Ethyl alcohol 4 g 
Butyl alcohol 4 g 
Camphor 2 g 
Butyl phthalate 4 g 
Toluene 20 g 
Ethyl acetate 10 g 
Butyl acetate 34 g 
100 g 
______________________________________ 
This nail lacquer or enamel when applied to the nails exhibits very good 
adhesion and excellent brightness for a prolonged period of time. 
This example is repeated except that the polymer of Example 50 is replaced 
without inconvenience by any one of the polymers of Examples 40-44, 49 and 
51. 
EXAMPLE S 
A colored nail lacquer or enamel is prepared by admixing the following 
components: 
______________________________________ 
The colorless nail lacquer 
of Example R 96.88 g 
Benzyl-dodecyl dimethyl- 
ammonium montmorillonite, 
Bentone 27 1 g 
Phosphoric acid 0.02 g 
Titanium oxide 1 g 
D and C Red No. 7 0.4 g 
D and C Red No. 11 0.2 g 
D and C Red No. 5 0.3 g 
Red iron oxide 0.2 g 
100 g 
______________________________________ 
This nail lacquer exhibits excellent brightness and very good adhesion.