Title of Invention	PROCESS TO PREPARE MULTI-FUNCTIONAL ACTIVES
Abstract	This invention relates to novel concept of preparation and usage of multifunctional active molecules, better known as "Actives" using quaternary nitrogen chemistry. This invention provides solution for delivering more than one functional properties at once in formulations.

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FORM 2 THE PATENTS ACT, 1970 COMPLETE SPECIFICATION (See Section 10) TITLE PROCESS TO PREPARE MULTI-FUNCTIONAL ACTIVES APPLICANT Galaxy Surfactants Limited C-49/2, TTC Industrial Area, Pawne, Navi-Mumbai 400 703, Maharashtra, India. A Public Limited Company Registered under Indian Company"s Act-1966 The following specification particularly describes the nature of the invention and the manner in which it is to be performed :- Field of invention The present invention provides a novel to make multi-functional actives "Actives" are molecules having specific functional attributes. These multifunctional actives will be referred as "Actives" hence forth in this patent. This novel approach in converting these functional actives into cationic surfactants by employing quaternisation process of tertiary nitrogen by epoxidation in aqueous media. The resultant quaternary ammonium base is neutralized with another active. There may be one or more such nitrogen ions present in the active molecule or can be introduced by reacting with suitable amines as mentioned in this invention later. Most of the actives used in various applications are water insoluble. Hence, they are delivered in emulsion form with the aid of surfactants. Some of the actives even if water soluble still requires surfactants for better spreading. Some time even help of solvent is also required to solubalise the actives. This invention provides approach to make these actives water soluble at the same time make them behave as surfactants by them selves. This novel approach also make it possible to combine more than one actives in the same molecule. Quaternary compounds are known for their antibacterial properties as well as their substantive nature. This invention provides, usage of these properties along with functional actives . This invention also provides an approach / process to make such multifunctional molecule . Epoxydation is a known process for quaternisation with this approach epoxidation can also be used to make tertiary nitrogen, which can be further converted to quaternary compound by further epoxydation in aqueous conditions . Attributes of these actives include but not limited to UV rays absorption properties, anti microbial properties, anti fungal property, anti dandruff, emulsifying property, fiber conditioning property, surface wetting property, film forming property, cleaning & detersive property, emulsifying and dispersing property, herbicidal, pesticidal, biocidal, weedicidal. These properties can be designed to the requirement & needs of the any formulations including cosmetics, medicinal, personal care, detergent & cleaning, sun care, pesticidal, fiber care, pains , polymers and plastics are some of the examples of applications where in the concept presented in this patent cab be used. The basic process is represented as follows. R1 + Amines Esters or amides or imidazolines Process with epoxidation in aqueous media using EO or PO or other epoxydatton agents in aqueous media Base with quaternary nitrogen Neutralisation with actives R1 or R2 or R3 as defined below Multifunctional novel molecule Where in R1 is a molecule aliphatic, aromatic, heterocyclic, substituted or un-substituted, saturated or unsaturated entities attached to functional groups like acid chloride or carboxyl or phenyl or any other functional group capable of giving amide or ester bonding. R2, R3 etc molecule aliphatic, aromatic, heterocyclic, substituted or un-substituted, saturated or unsaturated entities attached to functional group capable of providing acidity such as carboxylate, Hydroxide, phosphoric, sulphonic, thip etc. In typical examples, but not limited to, R1 can be taken from Para methoxy cinnamic acid , fatty acids C6 to C24 , Undecylenic acid, Para amino benzoic acid, Salicylic acid, antharanilic acid, Benzophenones, Triclosan, Phenolic or para chloro meta xylenol or pentachlorophenol, or N-(phosphonomethyl) glycerin, (Glyphosate) any such active, functional molecule etc The amine back bone can be sourced from following amines. Dimethyl amino propyl amine (DMAPA), Amino ethyl ethanol amine (AEEA), Diethyl tri amine(DETA), tri ethanol amine (TEA), methyl diethanol amine (MDEA), Di methyl amine (DMA), Tri methyl amine (TMA). and other like wise amines or poly amines. 2 The R1 to R4 is as illustrated in type 1. This relates & not limited to usage for multi functional compound especially quaternary ammonium compounds having unique combination of more than one functional properties. This also provide surfactant properties entailing ease of formulation. The formulations include very wide range of application. Biocides, Fungicides, anti-bacterial, skin care, hair care, lip care, dental care, and surface-cleaning formulations, paints, polymers, plastics & fabric care. Many of them have potential therapeutic value. Background of the invention Surfactant is a group of chemicals used in variety of fields for different reasons. They are also known as emulsifier. Their roll in application is varied & multi tasking. This includes foaming, wetting, solubilization, dispersing, spreading, coating, cleaning, wiping and so on. There use is so varied, it is difficult to envisage any formulation without usage of surfactant. Typical but not complete list of application include detergent powders. Drug formulation where in they are used to deliver drugs or disintegrate solid drug particles in to the metabolic system. Cosmetic formulation included shampoo to liquids cleaning milks to creams. Agriculture usage include crop protection solutions, which can be insecticide, herbicide, pesticides or fungicides. Oil soluble as well as water-soluble paint emulsions for wall care application. Each of the above application always intended to maximize benefits by delivering optimum dosages of actives at targeted spots. Many times a same formulation is intended for multiple functions. A cosmetic cream is used not only to protect the skin from ill effects of exposure to sun light but also to provide moisturizing effect to the skin as well as to deliver bactericide to protect the skin from environ mental bacterial contamination. Several such example can be given to point out multiple roll the formulation is expected to do. 4 The functional entity, which is expected to do these specific functions, are known as actives. In most of the cases these actives are oil soluble. They need auxiliary help to deliver the results. This includes solubilisers or emulsifiers, solvents, anti-oxidants, Colour stabilizers etc. Multi-functionality Of the formulations may also require more than one actives in the given formulation. The intention and object of this invention is to have such molecule, which will help us to reduce or nullify the requirement of this auxiliary help for wide array of formulation. Many molecules used in trade do provide this opportunity, as availability of chemically potential group in the molecule. For example, a surfactant molecule used in hair care formulation can be modified to give in conditioning as well as sunscreen protection. A bactericidal molecule having free OH group can be esterified or neutralized or amidised to impart it surface active properties. One can also make a water soluble active by this modification. In case of suitable available nitrogen atom in many molecules can be quatemised and the molecule is made substantive. This sight is also exploited to attach other active entities to impart sunscreen properties or surfactant properties or anti microbial properties as well. As will be shown later, this results in reducing requirement of actives, decreasing need for additional auxiliary in-puts and many other benefits. Thus a long felt need of multifunctional molecule is conceptualized in this invention. Prior art and Summery of the Invention: The present invention provides water soluble & or water dispersible functional compound, which is generally known as "Active" with one or more functional usages / attributes. The attributes can be one or more at the same time in the molecule. They include UV rays absorption properties, anti microbial properties, anti fungal property, emulsifying property, fiber conditioning property, surface wetting property, film forming property, cleaning & detersive property, emulsifying and dispersing property. These properties can be designed to the requirement & needs of the any formulations. Cosmetics, medicinal, personal care, detergent & cleaning, fire fighting, sun care, winter care are some of the examples of formulation where in the concept presented in this patent cab be used. Many of the above mentioned formulations contains compound which are intend to function & known as actives. They are delivered to do the function by way of suitable formulation. These formulation contains other in puts to augment the action of actives. 5 For example Octyl methoxy cinnamate is a compound used In sunscreen lotions meant to protect the body from harmful effects of sun rays. The Octyl methoxy cinnamate being oil, water insoluble compound requires emulsifiers for delivering the same on the skin surface. The additives include film forming compounds, moisturizers. Since OMC is only effective on certain wave length range known as UVA (280 to 320 nm) range additional sunscreen compound is used to enhance the effective ness through 320 to 400 nm. Compound like Benzophenon - 3 are used for this purpose. The results also accompanied by „ oily feeling, over dose requirement of actives and ill effect of certain surfactants such as harsh ness etc. The invention presented here can be applied to ensure that the same molecule gives sunscreen protection over the entire range by design. It can be made water soluble reducing or not requiring any surfactant. This also reduces the oily feeling. By its nature these compound are quaternary and thus substantive to the skin. This in turn reduces the dosage form required. For a formulation requiring to provide sunscreen protection as well as emolliency / conditioning giving property can be incorporated in the molecule by introducing the fatty alkyl group. Thus making the sunscreen molecule duel functional. It is widely reported that the hair become fragile due to effects of sun rays as well as become dry due to exposure to atmosphere. Although the US patent 5601811 refers to water soluble sunscreen compound it does not give scope of enlarging the functionality or duel usage compound. In another application in skin care formulation a sunscreen protection is provided along with microbial protection to skin. Present invention allow us to design a molecule as per requirement. In a conventional art this can be done by using sunscreen compounds like p-amino benzoic acid (PABAJ, p-methoxy cinnamate in combination with anti bacterial agents such as trichlosan Both actives are water insoluble demanding skill & complicated system for delivery. In present invention the compound such as p-methoxy cinnamido propyl 2-hydroxy ethyl dimethyl ammonium salt of 5-chloro -2 (2,4 dichloro phenoxy) phenol can be prepared & used in skin care formulation to provide double protection to the user. In agriculture pesticide formulation forms an important crop protection tools. Many of the actives used here are water insoluble. To be effective the active needs to be spread on contact surfaces of the plant such as leaves. Solubility in water do help them in there function. They should remain there for longer time for continued protection. In addition to this the residual quantities should not pose a threat to environment & user. This entails usage of solvents, surfactants, hydro topes in them. 6 Quaternary ammonium compound have been used since long. The positive Nitrogen also imparts many useful properties to the compound. Few of them are substantives on skin, cloth, hair etc. Antibacterial & anti fungal properties. These quaternary compounds are manufactured by different chemical routes well evaluated in prior art. An ethoxylation in aqueous media is one of such route used since many years. Surprisingly we have invented a method to modify these molecule further which will impart more useful properties in addition to the conventional properties of quatemary compounds. Present invention pertains to salts of quatemary ammonium compounds with various acids, aromatic as well as short chain & long chain fatty acids. This imparts the molecule duel functionality . The molecule will have at least one linear fatty chain or an aromatic chain This chain may be attached to the quatemary nitrogen covalently or ionically, thus imparting many more important properties to the molecule. The basic quatemary ammonium nitrogen can be ionically attached with another fatty acids or aliphatic or aromatic acid or mineral acid group by neutralization process using corresponding carboxylic a acid. This salt can be used suitably for different applications such as sun protection cosmetic formulations, cleaning, disinfecting formulations. The corresponding molecule can be introduced prior to quartemisation or after the quaternisation depending up on the application /intended use of the molecule. Rutzeb Horst & others in WO 8909204 A 1 1989, used the ethoxylation process to make a quaternary compound with one or two long chain alkyl residues covalently bonded with nitrogen atom of quaternary compound. The invention relates its usage only as fabric softener. The similar compound preparation have been reported earlier for use in softening textiles ( CA: 111/19996704 K), but not for usage indicated in this invention nor for incorporating multi functionality. This patent also do not visualize application other than fabric softening. Objects of the invention: « The inventors of the present patent further formulating art by introducing, anion with active attributes in the molecule. For this highly basic hydroxyl ion generated in unique quaternisation process is utilized. Thus enhancing and multiplying the functional attributes of original active molecule several time over. Thus the 7 present invention pertains to" usage of quaternary ammonium base salts in wide range of applications" as illustrated in examples. The application include usage of compounds of invention in formulations having multi-functionality. Present invention make this delivery, an easier job by making them water soluble or dispersible. The compound also have surfactant and substantive properties. This also reduce or eliminate requirement of solvent as well as surfactant in the formulations. Thus effectively open up opportunity of more efficient delivery at reduced dosages of toxic chemicals. Thus the present invention demonstrate & provides solution for long felt need of having unique combination of more than one property in a given compound. This opens up very wide range of formulating options in far wider range of applications. The opportunity includes lower, efficient dosage, lower actives thus more environment friendly ness and more safety to the user. Details of experiments:" Preparation of p-methoxy cinnamidopropyl dimethyiamine:- Para methoxy cinnamidopropyl dimethyl amine was synthesized as per procedure given in U. S. Patent No 6,426,435 B1 Similarly, preparation of coco fatty dimethyl amido propyl amine was made by conventional method Preparation of quaternary ammonium compounds from respective amides. Experiment no 1> Preparation of P-methoxy-cinnamidopropyl-di methyl, 2-hydroxyl ethyl, ammonium hydroxide A 5000 ml autoclave was charged 1070 gm (1.0 mole) , Water 1900 gm (25.84 mole). Stirring was started. Nlfrogen was "purged for 15 min to remove dissolve oxygen from reaction mass. Then three times Nitrogen pressure was taken & released. Finally 0.5kg/cm2 pressure was taken. 179.6gm (1.0 mole) Ethyleneoxide was added by maintaining reaction temperature 10-60 degree C. After ethylene oxide addition, reaction mass was digested for two hrs at same temperature. Then reaction mass was cooled to 30 degree C. The final quaternary ammonium compound was yellow color low viscous clear liquid. Product has purity of 40%. Examples : 2 Preparation of cocoamido propyl 2-hydroxy ethyl dimethyl ammonium hydroxide 800 grams of coco (C8 to C 18) amido propyl amine is mixed with 3099 grams of water. Nitrogen gas is purged through it for 5 minutes to drive off air. Initial 8 pressure of 0.5 kg of nitrogen was given. 175 grams of EO was added to this mass by maintaining the temperature between 10 to 60 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Preparation of neutralized salts of quaternary ammonium salts: The uniqueness of the invention is to introduce multi functionality. This is achieved in this step of process. Here suitable / desired second active functionality is introduced in the molecule. For this one can use any active compound, which can provide reactive acid group such as carboxylate, phenolic hydroxyl, phosphoric, acid chloride, and sulphonic or thio functional group. Typical but not limited to, molecules such as p-methoxy cinamic acid, fatty acids, benzophenon-3, glyphosic acid, Salicylic acid, ketakonazole, p-amino benzoic acid, undecylenic acid and several such others active molecule can be used. After preparing a quaternary compounds with one alkyl chain the compounds were treated with many mineral adds, long chain alkyl fatty acids or aromatic acids, so as to enhance there properties for different end use. Experiment no 3: Preparation of p-methoxv clnnamldo propyl 2-hvdroxvethvl dimethyl ammonium salt of cocofattv acld(Cinnamate-CFA):- A 2000 ml four neck round bottom flask was charged with 835 gm 40% (1.0 mole) Para methoxy cinnamidopropyl hydroxyethyl dimethyl ammonium hydroxide, Coco fatty acid C12-18 230 gm (1.0 mole) & water 150 gm (7^97 mole). Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30 degree C. The final product was yellow color low viscous mass. Product is completely water soluble. Product has purity of 46.9% & pH 8.6. Experiment no 4 ; Preparation of p-methoxv cinamido propyl 2-hvdroxvethvl dlmethvl ammonium salt of stearic acid (Clnnamate-StearateV: - A 1000 ml four neck round bottom flask was charged with 400 gm 40% (1.0 mole) Para methoxy cinnamidopropyl Hydroxyethyl dimethyl ammonium hydroxide, Stearic acid hystric grade C16-18 130 gm (1.0 mole) & water 150 gm (28.6 mole). Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30 degree C. The final product was yellow color low viscous mass. Product is completely water soluble. Product has purity of 37.2% & pH 9.4. Experiment no S: Preparation of p-methoxv cinamido proovi 2-hvdroxvethvl dlmethvl ammonium salt of Benzophenone 4 (Clnnamate-Benzophenone-4):- A 500 ml four neck round bottom flask was charged with 120.6 gm 40% (1.0 mole) Para methoxy cinnamidopropyl Hydroxyethyl 9 dimethyl ammonium hydroxide .Benzophenone -4 23.07 gm (0.5 mole) .Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30 degree C. The final product was yellow color low viscous mass. Product is completely water soluble. Product has solid content 48.37% & pH 10.8. Experiment no 6 : Preparation of p-methoxv clnnamido propyl 2-hvdroxvethvl dimethyl ammonium salt of Benzophenone 3fClnnamate-Benzophenone-31:- A 500 ml four neck round bottom flask was charged with 115.6 gm 40% (1.0 mole) Para methoxy cinnamidopropyl Hydroxyethyl dimethyl ammonium hydroxide , Benzophenone -3 35.6 gm (1.0 mole) .Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30 degree C. The final product was dark yellow color low viscous mass. Product shows milkyness in dilute solution. Product has solid content 53.8% & pH 11.05. Experiment no 7: Preparation of p-methoxv clnnamido propyl 2-hvdroxv ethvl dimethyl ammonium salt of Acrvlic acid (Cinnamate-Acrylate);- A 1000 ml four neck round bottom flask was charged with 590gm40% (1.0 mole) Para methoxy cinnamidopropyl Hydroxyethyl dimethyl ammonium hydroxide, Acrylic acid 52.4 gm (1.0 mole) .Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30 degree C. The final product was yellow color low viscous mass. Product has solid content 42.8% . Experiment no 8 : Preparation of p- methoxy clnnamido propyl 2-hvdroxv ethvl dimethyl ammonium salt of Undecvlenic acld(Cinnamate-Undecylenate):-A 1000 ml four neck round bottom flask was charged with 590gm40% (1.0 mole) Para methoxy cinnamidopropyl Hydroxyethyl dimethyl ammonium hydroxide, Undecylenic acid 118.9 gm (1.0 mole) & 271 gm water. Stirring was started & reaction temperature was maintained between 30-70 degree C for two hrs . Then reaction mass was cooled to 30. degree C. The final product was dark yellow color low viscous mass. Product has solid content 35% Example 9: Preparation of Coco amldo propyl 2-hvdroxvethvl dimethyl ammonium salt of palm fattv acid (CFA-PFA);- 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 70 grams of water and 36 Grams of distilled palm fatty acid (C16 & C18 fatty with iodine value of 38 ) were added to it under mixing. The mass was digested at 50 degree centigrade for 30 minutes. The neutralization is controlled by pH. At the constant pH of 8.8 is, the mixing is stopped. Example 10 : Preparation of Cocoamido propyl 2-hvdroxvethvl dimethyl ammonium salt of coco fattv acid ( CFA-CFA) 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 28 Grams of CFA (C8 to C18 ) were added to it under mixing. The mass was digested at 50 degree centigrade for 30 minutes. The neutralization is controlled by pH . At the constant pH of 8.2 is , the mixing is stopped. Example 11 : Preparation of Cocoamido propyl 2-hvdroxvethvl dimethyl ammonium salt of o-methoxv cinnamic acid (CFA-Clnnamatel 604 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 72.5 grams of p-methoxy cinnamic acid and 196 grams of water were added to it under mixing. The mass was digested at 50 degree centigrade for 30 minutes. The neutralization is controlled by pH . At the constant pH of 7.53, the mixing is stopped. Example 12: Preparation of Cocoamido propyl 2-hvdroxvethvl dimethyl ammonium salt of hydrochloride (CFA-HCL) 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 12.5 Grams of hydrochloric acid were added to it under mixing. The mass was digested at 30 degree centigrade for 30 minutes. The neutralization is controlled by pH . At the constant pH of 7.60 is , the mixing is stopped. Example 13 : Preparation of Cocoamido propyl 2-hvdroxvethvl dimethyl ammonium salt of Triclosan (CFA-Trlclosan) 2000 ml four neck round bottom flask was charged with 1000 gm 24% (1.0 mole) cocoamidopropyl Hydroxyethyl dimethyl ammonium hydroxide . Triclosan 190 gm (1.0 mole). Stirring was started & reaction temperature was maintained between 50-60 degree C for 30 minute . Then added slowly additional 250 gm 24% (0.25 mole) cocoamidopropyl Hydroxyethyl dimethyl ammonium hydroxide to get final mass clear liquid . Reaction mass was cooled to 30 degree C. The final product was yellow color low viscous mass. Product is giving milky solution in water. Product has purity of 34% & pH 9.7. Type 2, 3 & 4 molecules. Performance of Sunscreen functional molecule: Molar extinction coefficient were studied for these compounds along with other UV absorbing compounds. 11 Following are the molar extinction coefficients in methanol: Compound €E Molar extinction coefficient K Value Benzophenone-3 14500 72.6 Cinnamic-Benzophenone-3 salt 35600 63.79 Benzophenone-4 12500 45.30 Cinnamic- Benzophenone-4 salt 48000 65.78 Cinnamic-Anthranilic salt 26297 - Octyl methoxy cinnamate 27048 93.27 DEA Cinamate salt 22313 84.20 Cinnamic-cinnamic salt 42000 96.67 CFA - Cinamate 25099 47.90 Parasol-1789 26339 101.68 Cinnamate- Stearate 22930 39.40 Cinnamate - cinnamate 47561 96.67 Microbiology data:- Product P- methoxy ammonium cinnamate cinnamic APDM p- methoxy Cinnamic - CFA salt E. coli >8700 >4493 Staph. Aureus 8000-9600 4132-4770 Ps. aeruginosa >9500 >7776 From above data shows that these products show antimicrobial activity against Gram + ve bacteria. Thus for example, it can be seen that these molecules have UV absorption as well as antibacterial properties. Preparation of formulations : Hard surface cleaning formulations; A formulation is made containing 5.5% of active solution of example 12. No other surfactants was used in this test formulation. Trie diluted solutions were tested for effect on different strains of bacteria and it was seen that the compound 19 is more effective than the commercial disinfectant formulations used for the comparison. It is also needs to be noted that the test formulation does not contain any other ingredient unlike commercial market sample taken for experiments. 12 Thus it can be seen that in liquid surfactant blends like shampoo, floor cleaners, the compound of invention gives enhancement in more than one properties unlike the conventional chemicals used in trade. Dilution of the formulation / Name Bacteria used Inoculumn Growth after 5 minutes Growth after 10 minutes Growth after 15 minutes 2% test formulations Pseudomonas aeruginosa 0.1 ml + - - 2% Lyzol As above 0.1 ml + + + 2% Pinho sol As above 0.1 ml + + + After increasing the inoculumn Dilution of the formulation / Name Bacteria used Inoculumn Growth after 5 minutes Growth after 7.5 minutes Growth after 10 minutes 3% test formulations Pseudomonas aeruginosa 0.4 ml + - - 3% Lyzol As above 0.4 ml + + + 3% Pinho sol As above 0.4 ml + + + Thus even after increase in inoculumn the test compound was found to be more effective. Thus it also function as cleaning as well as antimicrobial agent. The molecule CFA- HCI has been analysed for foam by Ross Mile column & found to give 176 ml of foam indicating good foaming properties. The Minimum Inhibitory Concentration (MIC) is 40 & 12 for Escherichia coli and Staphylococcus aureus respectively. This gives us a molecule with surfactants base & antibacterial properties together. Performance of the invention in hair care : Compounds of inventions have been used for skin care formulations (Soaps) & hair care formulations. The data as given below shows the superior multifunctional properties of the compound of invention when compared to conventional products used in trade for skin / hair care formulations. The basic shampoo formulations has been made with 15% active anion surfactants such as Sodium lauryl sulphate, Sodium lauryl ether sulphate and alpha olefin sulphonate with 2% foam / viscosity booster (Cocomonoethanol amide ). The pH of the formulation was adjusted to 6.5 and then Sodium chloride was used as viscosity built up aid in the formulation. The performance was tested in terms of foaming power, salt required to built up certain viscosity and irritancy factor in terms of Zein value in a given surfactants system. For illustration compound of example 10 was used Formulation no. 1 2 3 Primary surfactant Sodium Lauryl sulphate Sodium Lauryl ether sulphate Alpha olefin sulphate Active matter of primary surfactant in aq. Solution. 15 15 15 Foaming on Ross Mile column , ml of foam volume Primary surfactant without foam booster 192 168 190 Primary surfactant with conventional foam booster CMEA at 2% W/W 192 190 200 Primary surfactant with invented molecule at 2% level 197 217 222 Irritancy test (Zein value, milligrams of zein per gram of 100 % solid of the formulation) Primary surfactant without any foam booster 465 278 328 Primary surfactant with foam booster CMEA at 2% w/w 465 279 326 Primary surfactant with invented molecule at 2% w/w 123 133 106 Viscosity response to Sodium Chloride to achieve 2500 cps of viscosity at temperature of28°c Primary surfactant without any foam booster 2.3 3.0 4.0 Primary surfactant with foam booster CMEA at 2% w/w 0.92 1.5 2.5 Primary surfactant with invented molecule at 2% w/w 0.75 1.0 1.8 Conclusion of data : More foam boosting of the formulation as against conventional foam boosters. The usage also reduces Zein value, indicating the formulation become more skin friendlier & thus more safer. Lower salt usage reduces a non contributing compound like sodium chloride in the formulation. Thus it can be seen that the compound of the invention can be very useful as Surfactant for cleaning, foam boosting as well as thickening agent in hair care preparation. 14 Sun care properties of the invented molecules: The sunscreens used in trade are mostly water insoluble compounds. Hence the novel way is provided by this invention to introduce these sunscreen activity in a surfactant molecule by making them substantive as well. The fatty group here gives conditioning properties as well. Compound (At 400 ppm dosage, in water system) Hair substantivity in mg of substance per 100 grams of hair ST. at 28 0C, 0.5% solution in D.W. OMC 41.04 Insoluble Cin-Benzophenon 3 139.92 - Cin -Benzo 4 98.87 - Cin-Stearic 120.01 - DEA-cinamate 9.67 - Stearic-Cin 18.41 - * Cin-CFA 122.68 38.2 CFA- Cin 36.89 29.2 Cin -Cin 51.38 38.2 MIC of actives introduced in the surfactant molecule: Tnchlosan is well known water insoluble antibacterial. Introduction of this actives into the compounds of invention make them water soluble . Thus the new molecule provide anti bacterial as well as surfactant properties. This multi-functionality results in efficient delivery of the compound. Sample MIC, In PPM ST. Dyne/cm2 Trochlosan E-coli - 2 Stap.cocus - 2 Psedo. Aero. > 300 plus Cand. Albican 10 Water insoluble CFA- tnchlosan E-coli-2 Stap.cocus - 2 Psedo. Aero 300 plus Cand. Albican 192 Asp. Niger .> 130 31.3 CFA:HCI E-coli = 38 34.8 Stap.cocus =12 Psedo. Aero. = 358 Cand. Albican =125 Asp. Niger = 650 15 Antidandruff properties on M. furfur % concen. Zone of inhibinition Effectivity against M. Furfur. ZPTO 0.5 10 mm Effective Water insoluble Unde-Unde 0.5 10 mm Effective Water soluble UNDE betaine 1.0 0 mm Not effective Watersoluble UndMEA 1.0 2 mm Not effective Water soluble Und MEASS 10 0mm Not effective Watersoluble Thus the new invention cab be used to make antidandruff agent which are water soluble 7 as effective as ZPTO. It is far more effective at far lower concentrations as compared to conventional Unde. Derivatives used as anti dandruff formulations. Methods of analysis: Foaming : Foaming is done using Ross Miles column as prescribed irr BIS 5785:1970 pH : pH of 5% solution is measured using pH meter. The solution is made in distilled water Viscosity : Viscosity was measured using Brook Field Viscometer modef LVT. Zein value: A known weight of Zein is shaken with an aqueous solution of surfactant system, The amount of Zein solubilised is determined gravimetrically. Anti Bacterial action: • Prepare solution of the formulation as per the dilution required for the test. • Inoculate the sample with required volume of the inoculum (as per the test planned) • Sub- culture after 2.5 min, 5 min, 7.5 min and 10 minute.( Initial experiments we had sub- cultured after 5,10 and 15 minute) in 5 ml Letheen broth. • After 48 hrs of incubation at 37 +7 - 2deg. Cent. Check for the growth of the organism. i • Test procedure for hain- The sustantivity of the compound to hair is tested in the following manner. The compound is dissolve in 100ml water to provide 0.08% by weight, aqueous solution. 5 gm hair is immersed in the aqueous solution., stirred for 10 minute then washed three times with water. Then hair are immersed in 200 ml Isopropyl alcohol. Heated to 60 degree C. for 30 minute. Then cool & dilute to 250 ml . Measure the absorbance & from absorbance reading concentration of sunscreen absorbed by hair is found out. Advantages of invention: The biggest advantage of the present invention is that they are substantive to hair when compared with water soluble, cationic , UV-B absorbers when they are applied through rinse-off preparation like shampoo. The other advantage of the present invention is that it has very good water solubility and hence it can be blended with anionic, cationic, nonionic and amphoteric surfactants. Present invention has both antimicrobial and sunscreen properties in one molecule and hence it is better for its use in various skin care, hair care formulations. Water insoluble compound like Triclosan can be effectively delivered through the present invention in various oral care formulation. We Claim, 1. Novel process to prepare a multifunctional actives type-1 surfactant of the formula, for use as surfactant in Skin care, hair care, fabric care formulation, Type 1: Where in R1 is a molecule aliphatic, aromatic, hetrocyclic, substituted or unsubstituted, saturated or unsaturated entities attached to functional groups like acid chloride or carboxyl or group capable of giving amide or ester bonding, etc. R2, R3 are molecules of aliphatic, aromatic, hetrocyclic, substituted or unsubstituted, saturated or unsaturated entities attached to functional group capable of providing acidity such as carboxylate, Hydroxide, phosphoric, sulphonic, thio etc. the amine back bone is selected from DMAPA, AEEA, DETA , TEA, MDEA , DMA , TMA and the like , comprising an epoxidation of R1 plus amine and ester or amides or imidazolines in aqueous media using EO or PO or other epoxidation agents in aqueous media, followed by quaternization using base and followed to neutraliz with actives of R1 or R2 or R3 such as here in defined , will give multifunctional molecule. 2.Novel process to prepare a multifunctional actives as claimed in claim -1 , wherein R1 is selected from the group consisting of paramethoxy cinnamic acid , fatty acids C6 to C24 , Undecylenic acid , paraamino benzoic acid , salycyclic acid, anthranilic acid, Benzophenones, Triclosan, phenolic or GIphosic acid or para chloro meta xylenol, 18 Claims of theiraeerffions: 1. Process to prepare multifunctional actives type-1 of the formula, for use as surfactant in Skin care, hair care, fabric care formulation. Where in R1 is a molecule aliphatic, aromatic, hetrocyclic, substituted or unsubstituted, saturated or unsaturated entities attached to functional groups like acid r\ chloride or carboxyl or group capable of giving amide or ester bonding. Aj R2, R3 etcinolecule aliphatic, aromatic, hetrocyclic, substituted or unsubstituted, " saturated or unsaturated entities attached to functional group capable of providing acidity such as carboxylate, Hydroxide, phosphoric, sulphonic, thio. The amine back bone is selected from DMAPA, AEEA, DETA , TEA, MDEA , DMA.TMA. Cov>vp-Y56>^> s^pJ *f/ Step-1:- Fatty acid is reacted with amine at140-200°C & pressure of 0.5-6 kg/cm2 to give amide.; Fatty acid + Amine - Amide Step-2:- Amide of step-1 was reacted with ethylene oxide & water at 10 -60°C & pressure of 0.5 - 5 kg/cm2 to give quaternary ammonium hydroxide. Amide + EO + WATER = Quaternary ammonium hydroxide. Step-3- Quaternary ammonium hydroxide of step-2 was neutralized with R1/R2/R3 type of acid to get required compound. This reaction is earned out at 30 - 70°C at atmospheric condition. This will give multifunctional molecule. x Quaternary ammonium hydroxide + R1/R2/R3 (Acid compound) = Quaternary ammonium compound 2. Process to prepare a multifunctional actives as claimed in claim -1 , wherein R1 is selected from paramethoxy cinnamic acid , fatty acids C6 to C24 , Undecylenic acid , paraamino benzoic acid , salycyclic acid, anthranilic acid, Benzophenones, Triclosan, phenolic or Glphosic acid or parachloro meta xylenol. 3. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 - paramethoxy cinnamic acid , R2 and R3 = CH3. 4. Process to prepare a multifunctional actives as claimed in claim A , wherein the said active type 1 is such that R1 = Cocofatty acid , R2 and R3 = CH3. 5. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = Undecylenic acid , R2 and R3 = CH3. 6. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = Cocofatty acid hydrochloric acid, R2and R3 = CH3. 7. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = Acrylic acid , R2 and R3 = CH3. 8. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = Cocofatty acid , para methoxy cinnamic acid, R2 and R3 = CH3. 9. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = cocofatty acid , Triclosan, R2and R3 - CH3. 10. Process to prepare a multifunctional actives as claimed in claim -1 , wherein the said active type 1 is such that R1 = Benzophenone, para methoxy cinnamic acid, R2and R3 = CH3. 19 11. Process to prepare a multifunctional actives type-1 surfactant such as here in described with reference to foregoing examples. Dated 22/10/2004 For Galaxy Surfactants Li Authorised Signatory. Name: Dilip Mhatre Designation: Manager Quality assurance (one of the inventor) 20 (Applicant)

Documents:

847-mum-2003-abstract(27-09-2005).doc

847-mum-2003-abstract(27-09-2005).pdf

847-mum-2003-claim(granted)-(27-09-2005).doc

847-mum-2003-claim(granted)-(27-09-2005).pdf

847-mum-2003-correspondence(02-06-2005).pdf

847-mum-2003-correspondence(ipo)-(10-06-2005).pdf

847-mum-2003-form 1(22-10-2004).pdf

847-mum-2003-form 1(26-08-2003).pdf

847-mum-2003-form 19(22-10-2004).pdf

847-mum-2003-form 2(granted)-(27-09-2005).doc

847-mum-2003-form 2(granted)-(27-09-2005).pdf

847-mum-2003-form 3(22-10-2004).pdf

847-mum-2003-form 3(26-08-2003).pdf

847-mum-2003-form 4(22-10-2004).pdf

847-mum-2003-form 5(22-10-2004).pdf