FORM 2
THE PATENTS ACT, 1970
COMPLETE SPECIFICATION
(See Section 10)
TITLE
Process for manufacture of water soluble, cationic, UV-absorbing organosiloxanes
APPLICANT
Galaxy Surfactants Ltd.,
C-49/2, TTC Industrial Area, Pawne, Navi-Mumbai 400 703, Maharashtra, India.
A Public Limited Company Registered under Indian Company's Act - 1956
The following specification particularly describes the nature of the invention and the manner in which it is to be performed :-


Field of Invention :
This invention relates to a process for manufacture of water-soluble cationic'Organosiloxanes
containing cirmamidoalkylarnine moieties. This invention particularly relates to synthesis of non-
hydrolyzable, UV-absorbing silicone polymers that are substantive to skin, hair and fabric and
hence useful for personal care.
Background and Prior Art :
Skin damage due to solar radiation is well documented. It is advisable to have protection from sun rays all throughout the day. Obviously, the sunscreen molecules that are designed to provide protection from sun rays round the clock ought to be totally non-toxic and they should never get absorbed through skin. In view of these properties polymeric sunscreens are suitable especially the polysiloxanes for cosmetic applications.
Silicone polymer containing UV-absorbing units for cosmetic sunscreen preparations have been reported. For instance, US patent, 4,545,980 (1985) teaches the art of anchoring cinnamoyl units on to hydroxy terminated silicones through an ester linkage.
US patent, 5,403,944 (1995) describes organosiJoxanes containing diethyl benzal malonate as the UV-absorbing chromophore. In skin care applications macromolecules containing siloxanes that remain on the surface of skin are less likely to penetrate the skin and hence are very effective in skin protection.
In summary, silicone bound UV-absorbers not only offer UV-protection but they confer desirable silky feel and have excellent dermatotoxicological profile. It should be noted that organosilicones reported so far are water-insoluble. However, there is no prior art of making silicone bound cationic water-soluble UV-absorbers for rinse-off preparations such as transparent shampoos, bathing bars and face washes. Such multifunctional organosiloxanes can act as sunscreens as well as conditioners by imparting silky feel due to silicone backbone and the cationic centres. Both silicone backbone and the cationic centres confer significant substantivity to these macromolecules. Hence, there is a need to create substantive, water-soluble silicone based sunscreens for rinse-off preparations.
Object of the Invention :
The main object is to synthesise organosiloxanes with cinnamido moiety to provide UV-absorption, cationic centres to provide significant levels of substantivity, conditioning property, water solubility, all useful in functional cosmetics.
Summary of the Invention :
The present invention provides a process for synthesis of cationic organosiloxanes containing cinnamidoalkylamine as represented by Formula I in the accompanying drawing, wherein;

R1, is a substituent, selected from -H, -halo, -OH, -NH2, -NO2, -OCH3, -N(CH3)2, alkyl groups containing from 1 to 6 carbon atoms, alkoxy groups containing from 1 to 6 carbon atoms, alkylamino groups containing from 1 to 6 carbon atoms or N,N-dialkylamino groups containing from 1 to 6 carbon atoms;
R2 is selected from hydrogen and alkyl group containing from 1 to 6 carbon atoms,
R3 and R4 are independently selected from benzyl and alkyl group containing from 1 to 6 carbon
atoms;
z is an integer from 1 to 6;
the counter ion of quaternary ammonium centre is chloride;
comprising steps of
(i) reacting 1.0 mole of a compound of Formula II shown in the accompanying drawing, wherein, R1 is same as that in the compounds of said Formula I, that are being synthesized, and R6 is -OH, -Cl or -O(CH2)PCH3 (p = 0 to 3), with 1 to 3 moles of a compound of Formula III shown in the accompanying drawing, wherein, R2, R3, R4 and z are same as those for the compounds of said Formula I, that are being synthesized, with or without a basic catalyst, with or without a solvent, to obtain a compound of Formula IV, shown in the accompanying drawing, wherein, R1, R2, R3, R4 and z are same as those for the compounds of said Formula I, that are being synthesized, till all of the said compound of Formula II has been reacted; removing the unreacted compound of said Formula III, remaining after the reaction and the solvent to obtain said compound of Formula IV;
(ii) preparation of quaternary ammonium compound of Formula V, by reacting epichlorohydrin (1.0 mole) and cinnamidoalkylamine (1.0 mole) in a solvent such as THF, t-butanol, dioxane at 60 - 80°C under nitrogen till the reaction is complete;
(iii) reacting quaternary compound of Formula V and the commercially available water-soluble dimethicone copolyol of Formula VI in solvent such as /-butanol in the presence of catalyst at 140°C under positive pressure of 1 to 15 kg/cm2 until the quaternary compound is reacted completely.
Detailed Description of the Invention :
The preferred substituents in cationic polymers of Formula I containing cinnamidoalkylamine are as follows;
The ring substituent R1 is selected from H, halo, -OH, -NO2, -OCH3, -N(CH3)2. The substituent on para position is preferred and the most preferred group is -OCH3.

Referring again to Formula I, the amido nitrogen is preferably unsubstituted (R2 is hydrogen). However, the amido nitrogen may contain a substituent, depicted in Formula ,I as R2, which is selected from alkyl groups containing from 1 to 6 carbon atoms.
The quaternized nitrogens of the compounds in accordance with the present invention contains substituents, R3 and R4 that are independently selected from hydrogen, benzyl and alkyl groups
containing from 1 to 6 carbon atoms.

The cationic silicone polymers of the present invention containing cinnamidoalkylamines moiety as
shown in Formula I, in which z is an integer between 1 and 6, both inclusive. Preferred
compounds in accordance with the present invention are cationic silicone 'polymers containing
cinnamidoalkylamines in which z is 3.
The cationic silicone polymers of the present invention are formed by reacting any commercially available water-soluble dimethicone copolyol (Formula VI), copolymers of dimethyl siioxane and polyoxyalkylene ether, regardless of any value for x, y, m and n with the quaternary compound of Formula V. The quaternary ammonium compounds of Formula V are in turn synthesised by reacting cinnamidoalkylamines with epichlorohydrin in the presence of a solvent like THF and the counter anion of the quaternary ammonium centre is chloride. Upon reaction of the compound of Formula V and the copolyols of Formula VI, the final cationic siloxanes will have same counter anion of chloride.
The number and the nature of the substituents selected is such that the final cationic polysiloxane is not rendered water insoluble.
In another embodiment the process of the present invention relates to manufacture of cationic, UV absorbing, water-soluble polymers of Formula I, shown in the accompanying drawing, in which RI is selected from -H, -OH, -NOi, -NH2, -halogen, N,N-dialkylamino groups containing from 1 to 6 carbon atoms; R2 is selected from -H, R3 and RI are independently selected from alkyl groups containing from 1 to 6 carbon atoms; z can have values from 1 to 6, from the compounds of Formula II, III, IV, V and VI shown in the accompanying drawing, with respective substituents RI of Formula II, R2, R3, R4 and z of Formula III as defined for the polysiloxane of Formula I, in this embodiment and R6 of Formula II being -OH, -CI, -Br or -O(CH2)PCH3 (p = 0 to 3).
In another embodiment the process of the present invention relates to manufacture of cationic, UV absorbing, water-soluble, polysiloxanes of Formula I, shown in the accompanying drawing, in which R, = para -OCH3, R2 = -H, R3 = R4, = -CH3, and z = 3, from the compounds of Formula V (p-methoxy cinnnamidopropyldimethyl-2,3-epoxy propyl ammonium chloride, s R) = -OCH3, R2 = -H, R3, R4, = -CH3) and Formula VI (dimethicone copolyol of GE Silicones, SF-1188A); Formula. V is in turn obtained from Formula IV (p-methoxy cinnamidopropyldimethyl amine, R1 = -OCH3, R2 = -H, R3, R4 = -CH3) and epichlorohydrin; Formula IV is in turn obtained from Formula II (p-methoxy cinnamoyl chloride, RI = para -OCH3 and R6 = Cl) and Formula III (N,N-dimethylpropyldiamine, R2 = -H, R3 = R4 = -CH3, z = 3).

The synthesis of the functional silicone polymers represented by Formula I is carried out in three steps, (a) synthesis of cinnamidoalkylamines, (b) synthesis of quaternary ammonium-chloride of Formula V and (c) condensation of quaternary ammonium salts of Formula V and dimethicone copolyol of Formula VI.
(a) Synthesis of cinnamidoalkylamines :
In this process, the synthesis of cinnamidoalkylamines involves, the amidification reaction between a compound of the Formula IT when R6 = -OH or O-(CH2)pCH3 (p = 0 to 3), with that of Formula III. It is carried in one embodiment of the invention, under pressure from'about'lO psi to about 100 psi, in the presence of a basic catalyst such as sodium methoxide, sodium hydroxide from 0.25 % to 5.0 % by weight of the reaction mass at from about 120°C to about 200°C, to afford the intermediate compound of Formula IV. From about 0.5 % to 5.0 % w/w of the basic catalyst is preferred. The more preferred amount of such catalyst is 1.0 % w/w. The reaction is conveniently monitored by TLC using Merck's silica gel coated on either aluminium of plastic or reversed phase HPLC using UV detection. After the complete disappearance of Formula II, the excess diamine is distilled off under vacuum.
In another embodiment of the invention, the reaction is carried out under atmospheric pressure, under blanket of nitrogen, with an arrangement for continuous selective removal of lower alcohol formed in the reaction, in the presence of a basic catalyst such as sodium methoxide, sodium hydroxide from 0.25 % to 5.0 % by weight of the reaction mass. Thus, the condensation reaction of one mole of cinnamic acid ester is carried with 1.0 to 3 moles of diamine at 120 to 200°C, preferably at 180°C, for 12 to 36 hours. The amines themselves can catalyse the reaction, however, the rates are found to be slower as compared with the bases like sodium methoxide and the like.
The compounds of Formula IV are synthesised by reacting acid chlorides of Formula n (1.0 mole) when R6 is -Cl with the diamines of Formula III (1.0 to 1.2 mole) at 20 - 50°C in an inert solvent like dichloromethane, ethylene dichloride, tetrahydrofiiran and the like. The amidification reaction between a compound of Formula II when R6 = -Cl is carried out with that of Formula III at room temperature in the presence of solvent.
(b) Synthesis of quaternary ammonium chlorides of Formula V :
Cinnamidoalkyl, dialkyl, 2,3-epoxypropyl ammonium chloride of Formula V is prepared by N-alkylating the cinnamidoalkyl, dialkylamine with epichlorohydrin in suitable solvents ranging from weakly polar THF to highly polar f-butanol. The quaternary salt separates out if the reaction is carried in weakly polar solvent whereas the product remains in solution if the reaction is carried in polar protic solvents such as t-butanol and the like. The reaction is done under an inert atmosphere of either nitrogen or argoa The temperature at which the quaternisation is effected generally depends upon the solvent. Equimolar quantities of both the reactants are taken in a solvent and heated under stirring for 18 to 24 hours at just below the boiling point of the solvent. The progress of the reaction is monitored by estimating the liberated chloride anion.

(c) condensation of quaternary ammonium salts of Formula V and dimethicone copolyol of Formula VI:
This condensation involves opening of epoxide ring of quaternary ammonium salt of Formula V by commercially available, well defined silicone copolyols. The silicone copolyols with terminal hydroxy groups are available from General Electric, Dow Corning, Wacker Chemie, etc. Dimethicone copolyol is a copolymer of polydimethyl siloxane and polyalkylene ether that is soluble in water and lower alcohols (e.g. SF1188A and SF1288 of GE Silicones; details are given in experimental). It exhibits surfactant properties by virtue of having hydrophobic silicone and hydrophilic oxyethylene groups and hydroxyl group at the terminus,
The equivalence of quaternary ammonium salts of cinnamidoalkylamines for the condensation step is decided by estimating the 'hydroxyl group' content of silicone copolyols. This condensation can be conveniently effected by performing the reaction under positive pressure of an inert gas (1 - 10 kg / cm2) in a suitable solvent that doesn't react with compounds of an formula V such as DMF, t-butanol, etc., at temperature between 100 - 200°C, preferably at 140°C for it 3 - 8 hours. This condensation can be effected with or without a catalyst. The catalyst employed is a base such as ethoxide / methoxide or carbonate of alkali metals like sodium or potassium and are used at 0.1 - 0.5 % w/w of the total reactants. The condensation proceeds very slowly without a catalyst. The concentration of both the reactants (Formula V and Formula VI) in the reaction mixture can vary from 20 to 80 % w/w. The progress of the reaction is monitored by analysing the reaction mixture by HPLC using the technique of reverse phase ion-pair chromatography along with UV detection. This technique allows to estimate the residual unreacted quaternary ammonium compound.
At the end of the reaction the functionalised dimethicone copolyol is then isolated by removing the solvent under vacuum. This polysiloxane is then purified by redissolving it in water and heating its aqueous solution above its cloud point (at 60 - 80°C) and isolating the precipitated polymer. E1% tcm of the purified polysiloxane is around 80 indicating about 5 % loading of UV-absorbing molecule. The spectral data is in complete agreement with the incorporation of UV-B absorbing unit. The polymer thus obtained retains all its o'ther original properties This purified polymer is dissolved in water to afford 50 % pale yellow coloured aqueous solution. This aqueous solution containing cationic, UV-absorbing substantive porysiloxanes of the present invention can be easily incorporated in formulations for skin and hair care products.
Examples
The invention will now be illustrated with the help of examples. The examples are by way of illustrations only and in no way restrict the scope of invention.
Dimethicone copolyol SF-1188A or SF-1288 were obtained from General Electric Silicones, Bangalore, India. SF1188A silicon polyether has INCI name as PEG/PPG-20/15 Dimethicone and is a stable copolymer of a polydimethyl siloxane and a polyoxyalkylene ether. It is soluble in

cold water and shows inverse solubility above 48°C. Its other specifications given in manufacturers data sheet are as follows -

Property Value
Active content, % 100
Appearance Clear - Straw
Viscosity, cstks @ 25°C (77°F) 800-1400
Specific Gravity, 25°C (77°F) 1.04
Density, Ibs/gal avg. 8.62
Flash Point, closed cup, °C (°F) > 100 (> 212)
Surface Tension, dynes / cm 25°C (77°F). 1.0 % aqueous solution 20.5
Inverse Solubility Point, °C (°F), 1.0 % aqueous solution 48°C(118°F)
Refractive Index 1.4484
p-Methoxy cinnamic acid was obtained from Galaxy Surfactants Ltd., Mumbai, N,N-dimethyl propyl diamine from BASF, epichlorohydrin, DMF, t-butanol, methylene chloride and thionyl chloride were purchased from S. D. Fine Chem, Mumbai. All chemicals were of analytical grade and the solvents for spectroscopy and chromatography were of HPLC grade.
Example I
Process for preparation of cationic. organosiloxane of Formula I. wherein. R1 = para -OCH3 R2 =
-H, R2 = R4 = -CH3 and z =3 :
This polymer is synthesised by following three steps;
p-Methoxy cinnamoyl chloride required for step (a) was prepared as follows ;
To a stirred suspension ofp-methoxy cinnamic acid (178.0 g, 1.0 mole) in dichloromethane (500 ml), thionyl chloride (238.0 g, 2.0 moles) was added slowly and the reaction mass was heated at 45°C for 3 hours. The excess of thionyl chloride was removed under vacuum and the p-methoxy cinnamoyl chloride was distilled (145°C / 0.2 mm) in 85 % yield as colourless solid with m, p. 50°C (Literature m.p. 50°C, Dictionary of Organic Compounds, Chapmann and Hall, 1994).
fa) Preparation ofp-methoxy cinnamidopropyldimethvlamine :
To a stirred solution of N,N-dimethylpropyldiamine (102.0 g, 1.0 mole) in dichloromethane (500 ml), solution ofp-methoxy cinnamoyl chloride (196.0 g, 1.0 mole) in dichloromethane (200 ml) was slowly added and the reaction was continued at room temperature for 2 hours. The reaction mixture in dichloromethane was washed with aqueous sodium hydroxide (200 ml, 20.0 %). The organic layer was dried over anhydrous sodium sulphate. The removal of solvent using a rotary evaporator afforded the p-methoxy cinnamidopropyldimethylamine (235.0 g) as colourless solid, m.p. 80°C. Reversed phase HPLC showed it to be 98 % pure with amine value 217.

The excess amine was removed under vacuum. The golden yellow solid (263.0 g) thus obtained had amine value of 245. Molar extinction coefficient, E, in methanol was found to be 26,600 at 290 nm.
IR in dichloromethane showed carbonyl stretching of amide at 1660 cm" and NH stretching at 3300cm-1.
H NMR (300 MHz, CDCl3) : δ 1.73 (p, 2H, J = 6.6 Hz), 2.26 (s, 6H), 2.42 (t, 2H, J = 6.6 Hz), 3.45 (q, 2H, J - 6.0 Hz), 3.81 (s, 3H), 6.27 (d, 1H, J = 15.6 Hz), 6.86 (d, 2H, J - 8.7 Hz), 7.43 (d, 2H, J = 8.7 Hz), 7.53 (d, 1H, J = 15.6 Hz).
(b) Synthesis of p-methoxy cinnamidopropyldimethyl-23-epoxvpropyl ammonium chloride :
A mixture of p-methoxy cinnamidopropyldimethylamine (100 g, 0.38 mole) and epichlorohydrin (35.3 g, 0.38 mole) in t-butanol (40 ml) was stirred under nitrogen atmosphere for 6 hours at 80°C. During this period reaction was complete as was judged by the estimation of chloride content. The HPLC analysis by reverse phase ion-pair chromatography confirm the absence of unquaternised tertiary amine. The removal of solvent yielded 135.0 g of quaternary ammonium compound as white hygroscopic solid with chloride content of 2.91 % w/w and with molar extinction coefficient of 24,000 in water at λmax 298.0 nm (El%Icm in water at fonax 298.0 nm = 830).
The following are the conditions used for ion-pair chromatography;
Column : ChromSpher C8 - 5 µm.
Mobile phase : 0.1 % Octane sulphonic acid in 56 % v/v aqueous methanol.
Flow rate : 0.30 ml / min.
UV detection at: 280 nm.
'H NMR (300 MHz, D2O) : 5 1.96 - 2.01 (m, 2H), 3.35 - 3.56 (m, 9H), 3.27 (s, 6H), 3.76 and 3.84 (2s, 3H), 4.25 (d, 1H), 6.33 - 6.47 (m, 1H), 6.9 - 7.02 (m, dd, 2H), 7.42 - 7.58 (m, 3H).
(c) condensation of dimethicone copolvol and p-methoxy cinnamidopropyldimethyl-2.3-epoxy
propyl ammonium chloride :
A mixture of dimethicone copolyol (G. E. Silicones SF-1188A, hydroxyl value = 22) (200 g),p-methoxy cinnamidopropyldimethyl-2,3-epoxypropyl ammonium chloride (28.3 g, 0.08 mole), sodium methoxide (0.22 g) and /-butanol (690 ml) in an autoclave was purged with nitrogen. The reaction vessel was pressurised with nitrogen (5 kg/cm2) and the reaction mixture was stirred at 130 - 135°C for 16 hours. On completion of reaction (monitored by HPLC using conditions described in step b) the solvent was removed and the viscous pale yellow product was redissolved in water. It was reprecipitated by heating the aqueous solution to 70°C with addition of salt. The precipitated polymer (182.0 g) was separated and redissolved in water to get 50 % w/w pale yellow coloured aqueous solution.
Surface tension (0.5%) was found to be 36 dynes / cm.

UV : E1%,1cm in water = 80 at λmax 298 nm.
IR (neat): 3500, 2900 cm-1.

H NMR : 8 0.08 (broad signal for silica bound methyls), 1.15 (methyl of polypropyloxy), 3.6 -
3.7 (protons on carbon next to oxygens), 6.58, 6.98, 7.62 (vinylic and aromatic).
Advantages of the process of the present invention :
The process of the present invention gives cationic silicones containing cinnamidoalkylamines
having high water-solubility, substantivity to hair and skin, conditioning and sunscreening

properties useful in personal care compositions.
Compared to monomeric UV-absorbers, silicone bound sunscreen agents are extremely useful in personal care product because of extremely low toxicity and very low absorption through skin. Such polymers are useful in daily-use cosmetics. They are highly substantive due to silicone backbone as well as cationic centres. Although water-soluble, they can be emulsified and they can be easily incorporated in cosmetic preparations containing oily phases. Relative low loading of UV-absorbing units on cationic polysiloxanes is an ideal product for hair and skin protection everyday (life long) use in addition to imparting silken feel of silicones.

We claim
1. A process for synthesis of cationic organosiloxanes containing cinnamidoalkylamine as
represented by Formula I in the accompanying drawing, wherein;
R1 is a substituent, selected from -H, -halo, -OH, -NH2, -NO2, -OCH3, -N(CH3)2, alkyl groups
containing from 1 to 6 carbon atoms, alkoxy groups containing from 1 to 6 carbon atoms,
alkylamino groups containing from 1 to 6 carbon atoms or N,N-dialkyIamino groups containing
from 1 to 6 carbon atoms;
R2 is selected from hydrogen and alkyl group containing from 1 to 6 carbon atoms,

R3 and R4 are independently selected from benzyl and alkyl group containing from l to 6 carbon atoms;
z is an integer from 1 to 6;
the counter ion of quaternary ammonium centre is chloride;
comprising steps of
(i) reacting 1.0 mole of a compound of Formula II shown in the accompanying drawing, wherein, Ri is same as that in the compounds of said Formula I, that are being synthesized, and R6 is -OH, -Cl or -O(CH2)PCH3 (p = 0 to 3), with 1 to 3 moles of a compound of Formula III shown in the accompanying drawing, wherein, R2, R3, R4 and z are same as those for the compounds of said Formula I, that are being synthesized, with or without a basic catalyst, with or without a solvent, to obtain a compound of Formula IV, shown in the accompanying drawing, wherein, R1, R2, R3, R4 and z are same as those for the compounds of said Formula I, that are being synthesized, till all of the said compound of Formula II has been reacted; removing the unreacted compound of said Formula III, remaining after the reaction and the solvent to obtain said compound of Formula IV;
(ii) preparation of quaternary ammonium compound of Formula V, by reacting epichlorohydrin (1.0 mole) and cinnamidoalkylamine (1.0 mole) in a solvent such as THF, /-butanol, dioxane at 60 - 80°C under nitrogen till the reaction is complete;
(iii) reacting quaternary compound of Formula V and the commercially available water-soluble dimethicone copolyol of Formula VI in solvent such as t-butanol in the presence of catalyst at 140°C under positive pressure of 1 to 15 kg/cm2 until the quaternary compound is reacted completely.
2. A process as claimed in claim 1, wherein the compounds of Formula IV are synthesised by
reacting acid chlorides of Formula II (1.0 mole) when R6 is Cl with the diamines of Formula III
(1.0 to 1.2 mole) at 20 - 50°C in an inert solvent like dichloromethane, ethylene dichloride,
tetrahydrofuran and the like.
3. A process as claimed in claim 1, step (i) wherein, the said reaction of compound of said
Formula IT (1.0 mole) when R6 is O-(CH2)PCH3 (p - 0 to 3), with that of said Formula ITT (1.0

to 3.0 moles) is carried out at about 120°C to about 200°C, under pressure from about 10 psi to about 100 psi, in the presence of a basic catalyst such as sodium methoxide, sodium hydroxide, from 0.25 % to 5.0 % by weight of the reaction mass.
4. A process as claimed in claim 1, step (ii), wherein, cinnamidoalkyldialkylamines (Formula IV)
are quaternised by epichlorohydrin in a suitable any solvent in which both the starting materials .
are soluble such as weakly polar THF or polar t-butanol at temperatures close to their boiling
points.
5. A process as claimed in claim 1, step (iii), wherein, p-methoxy cinnnamidopropyldimethyl-2,3-
epoxy propyl ammonium chloride (Formula V) is reacted with commercially available,-well
defined water-soluble dimethicone copolyols in a suitable solvent like f-butanol under pressure
at 120 - 150°C, preferably at 140°C.
6. A process as claimed in claim 1-6, wherein are manufactured porysiloxanes of Formula I shown
in the accompanying drawing, in which RI is selected from -H, -OH, -NO2, -NH2, -halogen,
Af W-dialkylamino groups containing from 1 to 6 carbon atoms; R2 is selected from -H, R3 and
RI are independently selected from alkyl groups containing from 1 to 6 carbon atoms; z can
have values from 1 to 6, from the compounds of Formula II, in, IV, V and VI shown in the
accompanying drawing, with respective substituents RI of Formula II, R2, R3, RI and z of
Formula III as defined for the polysiloxane of Formula I, in this claim and R6 of Formula II
being -OH, -Cl, -Br or -O(CH2)pCH3 (p - 0 to 3).
7. A process as claimed in any claim 1-7, wherein, are manufactured silicone polymers of
Formula I, shown in the accompanying drawing, in which RI = para -OCH3, R2 = -H, R3 = Rt
= -CH3, and z - 3, from the compounds of Formula V (p-methoxy cinnnamidopropyldimethyl-
2,3-epoxy propyl ammonium chloride, RI = -OCH3, R2 - -H, R3, RI = -CH3) and Formula VI
(dimethicone copolyol of GE Silicones, SF-1188A); Formula V is in turn obtained from
Formula IV (p-methoxy cinnamidopropyldimethyl amine, RI = -OCH3, R2 = -H, R3, R4 = -
CH3) and epichlorohydrin; Formula IV is in turn obtained from Formula II (p-methoxy
cinnamoyl chloride, R1 = para -OCH3 and R6 = Cl) and Formula III (N,N-
dimethylpropyldiamine, R2 = -H, R3 = R4 = -CH3, z = 3).
8. A process for preparing novel, cationic silicone polymers containing cinnamidoalkylamines, of
general Formula I, shown in the accompanying drawing, substantially as herein described, in
the text and in the examples.

Dated 10th. this day of August, 2001.