Title of Invention

AMIDOBETAINES FOR ORAL CARE APPLICATIONS

Abstract

An aqueous composition for oral care application comprising solution of an amidobetaine of the following general Formula 1 is disclosed; in which R is an alkyl of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture group which, on the average, corresponds to account fatty acids, wherein the solution has a solids content of 36 % by weight, a pH of 4.5 to 6, an alkylamidopropyldimethyl amine content of not more than 0.1% by weight, and a free fatty acid content less than 0.5% by weight, sodium chloride content of 6.0% max and dimethylaminopropylamino betaine (from N,N-dimethyl amino propyl 1,3-diamine (DMAPA) and monochloroacetic acid) content of 150 ppm max, free sodium monochloroacetic acid content of 5 ppm max and free N,N-dimethylamino propyl 1,3- diamine content of 5.0 ppm max. Amidobetaine composition of higher active matter content (total solids 45%)for oral care application is also disclosed.

Full Text

FORM 2 THE PATENTS ACT, 1970 (39 of 1970) COMPLETE SPECIFICATION (See Section 10: Rule 13) TITLE Amidobetaines for oral care applications 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 this invention and the manner in which it is to be performed: - 1 FIELD OF INVENTION The present invention relates to a composition of cocoamidopropyl betaine suitable for oral care applications such as mouth washes and tooth paste containing quaternary ammonium type of antimicrobials for control of oral bacteria. The present invention also relates to a process of manufacture of amidobetaine composition for personal / oral care application. The present invention further relates to a process for the preparation of aqueous amidobetaine composition for oral care application comprising a betaine of the general Formula I, which is superior to commercially available CAPB in terms of impurities. Formula I The present invention also relates to a process of manufacture of alkylamidopropylbetaines, which control the generation of impurities and the byproducts. BACKGROUND OF INVENTION Alkylamidopropyl betaines in general and cocoamidopropyl betaine (CAPB, CAS 61789-. 40-0) in particular are known for their mildness and hence are very widely used in personal care and consumer products ["Encyclopedia of conditioning rinse ingredients" ed. A. L. L. Hunting, Micelle Press, London (1987), p.125]. As a result of their superior performance, biodegradability and low toxicology profile, they are used on huge scale in cosmetic industry [X. Domingo, "Amphoteric 2 Surfactants" ed. E. G. Lomax, Surfactant Science Series, Marcel Dekker Inc., New York, (1996), Vol. 59, p. 75 and J. G. Weers, J. F. Rathman, F. U. Axe, C. A. Crichlow, L. D. Foland, D. R. Scheuing, R. J. Wiersema and A. G. Zielske, Langmuir, 7, 854-867, (1991)]. A conventional commercial amidobetaine (CAPB) composition for personal care applications typically has the following composition: Water 64 % by weight Betaine (Formula I) 28 - 29 % by weight NaCI 5 - 6 % by weight Glycerin 0.3 % by weight Fatty acid 0.5 % by weight Amidoamine (Formulall) ca. 0.3 % by weight Total solids content ca. 36 % by weight The solids content represents the sum of the components other than water. The synthesis of betaine involves a two-step process. In the first step, fatty acid (or methyl or glyceryl ester of fatty acid) is reacted with N, A/-dimethylaminopropyl diamine (DMAPA) as depicted in eq-1 to yield alkylamidopropyldimethyl amine of Formula II. In the second step, alkylamidopropyldimethyl amine of step one is quaternized using sodium monochloroacetate (SMCA) in aqueous medium as shown in eq-2 to yield amidobetaine of Formula I. The proportions of amidobetaine and sodium chloride arise out of the stoichiometry of the reaction of the fatty amide (Formula II) with the tertiary amino group and sodium chloroacetate according to the equations given below. 3 The free amidoamine content (Formula II) in the final amidobetaine arises from the incomplete quaternization and can be further reduced by an adapted stoichiometry and reaction procedure. It is usually present at around 0.3 to 0.5% in commercial betaine compositions. Small amounts of fatty acids (0.5 %) in the amidobetaine composition results from synthesis of the amidoamine from the corresponding fatty acid and 3-N,N-dimethylaminopropyl amine (DMAPA). Further, a typical amidobetaine composition will contain glycerin if the amidoamine (Formula II) is synthesized from triglycerides (coconut or palm oil) and 3-/V, N-dimethylaminopropyl amine. Anionic surfactants like sodium lauryl sulphate (SLS), sodium cocoyl glycinate or sodium lauroyl sarcosinate are used in dentifrice applications. Sodium lauryl sulphate is the most commonly used anionic surfactant in the toothpaste formulation. A typical toothpaste formulation contains 0.5 to 1.5 % of SLS for its foaming and surfactant action. However, these anionic surfactants are incompatible with the cationic ingredients of the formulation, especially with the quaternary ammonium type of antimicrobial molecules. Due to this incompatibility, one is compelled to use non-cationic antimicrobial agents that are either phenolic or halogenated molecules, e.g. triclosan or chlorhexidine. It is also pertinent to mention here that the most popular anionic surfactant for oral care applications, SLS, is actually a skin irritant and is generally not used in leave-on skin care preparations. SLS is also reported to cause significantly higher mucosal desquamation compared to amphoteric surfactants. (B. B. Herlofson 4 and P. Barkvoll, Err. J. Oral. Sci., 104, 21:6 (1996). However, despite these drawbacks the anionic surfactants are still being used since there are no other suitable alternatives. The cationic surfactants have incompatibility problem with other anionic ingredients. The nonionic surfactants are compatible with ionic ingredients but they do not foam. The amphoteric surfactants are free of this ionic incompatibility problem and hence they can be used with a cationic active in a formulation. PCT application WO 97/46217, EP 0910333 and EP 0966256 describe a mouthwash composition comprising cationic antimicrobial cetyl pyridinium chloride and amphoteric cocoamidopropyl betaine. According to the patents EP 0764015, US 5,256,823, and US 5,135,543 quaternary ammonium compounds are found to be extremely useful in reducing oral bacteria and quite effective in preventing plaque and related periodontal diseases like gingivitis. An amphoteric surfactant like CAPB has all the desired properties of being mild, biodegradable and foaming. It can replace anionic surfactants. It is also well known that combination of CAPB with an anionic like SLS results in foam boosting as well as reduces the latter's irritation potential. Hence an irritant like SLS can be fully or partially replaced by CAPB. There have been a number of instances in the prior art (WO 0226203 (1992), JP 04134025 (1992), EP 658340 (1993), EP 692246 (1994), WO 9746217 (1997), JP 0912437 (1997), JP 0912175965 (1997). WO 0170183 (2001) and WO 0226203 are dentifrice compositions and are based on the amphoteric betaines and not on any anionic surfactant. However, CAPB suffers from a major disadvantage of being bitter in taste. The bitter taste can be overcome to some extent by adding more sweeteners. EP 658430 (1993) describes dentifrice compositions containing significant quantitities of amidobetaines wherein bitter after taste is significantly reduced using sweetening agents like thaumatin or sterioside in addition to sodium saccharine. This limits its use in oral care formulations and thus there is a great need for a suitable 5 amphoteric surfactant in oral care formulations. The inventors of the present invention have discovered that the inherent bitterness of CAPB composition stems from the original amidobetaine molecule (Formula I) as well as the impurities present in the composition. The impurities of the composition are several times more bitter that the actual amidobetaine molecule and the bitterness of a typical composition can be reduced significantly, almost 80 %, by overall reducing the impurities and byproducts, in particular the betaine formed from N, A/-dimethylpropyl 1,3-diamine and monochloroacetic acid (Formula III) eq -3. This impurity has been identified as the bitterest of all the impurities and the by-products. In commercially available amidobetaine compositions for personal care the betaine of Formula III was found to be significantly high and there is no mention of its presence or its analysis in the prior art on this amphoteric surfactant. Formula III OBJECT OF INVENTION It is an object of the present invention to provide an amidobetaine, which contains fewer impurities as compared to commercially available amidobetaine. It is further object of the present invention to provide an amidobetaine for oral care applications which is less bitter. It is further object of the present invention to provide a process for preparing aqueous amidobetaine composition for oral care application comprising a betaine of the general Formula I. Yet another object of the present invention to provide an amidobetaine 6 which will partly or fully replace the anionic surfactants like sodium lauryl sulphate Yet another objective is to provide an amidobetaine composition that is far superior to the regular commercial CAPB for personal care applications (hand wash, body wash, shampoo, and bathing bar). SUMMARY OF INVENTION According to one aspect of the present invention there is provided an amidobetaine composition comprising a betaine of the general Formula I, Formula I In which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture, which, on the average, corresponds to coconut fatty acids, An amidoamine of not more than 0.1 % by weight, a free fatty acid less than 0.5 % by weight, 0 to 4 % by weight of glycerin, based on composition, less than 5 ppm of free sodium monochloroacetate and, less than 150 ppm of aminopropyl dimethylamino betaine ( Formula 111), Formula III 7 less than 5 ppm of free DMAPA wherein the composition has a solids content of at least 36 % by weight and a pH of 4.5 to 6. According to another aspect of the present invention the said amidobetaine of formula I is prepared by a two step procedure that controls the generation of impurities and the byproducts comprising quatemization of amidoamine of Formula II that contains less than 400 ppm of free N, A/-dimethyl propyl diamine (DMAPA), Formula II wherein, R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture which, on the average, corresponds to coconut fatty acids alkyl group, with sodium salt of monochloroacetic acid at 80 - 85°C while maintaining the pH between 7.5 to 8.5 by adding concentrated solution of sodium hydroxide till amidoamine content of the reaction mass has been brought down to 0.1% or less; raising the pH to between 10 to 10.5 and reaction is continued at a temperature of between 90 - 98°C for a period of 4 - 8 hours and thereafter adjusting the pH to 4.5 to 6.0 with phosphoric acid or citric acid. DETAILED DESCRIPTION Alkylamidopropyl betaines of the present invention for oral care have been achieved by a two step procedure that controls the generation of impurities and the byproducts. The amidobetaines of the present invention are produced by quaternizing the alkylamidopropyldimethylamine of Formula II with stoichiometric quantity of sodium 8 monochloro acetate in aqueous medium. Thus, the first step in the synthesis of alkylamidopropyl betaine of the present invention is the synthesis of alkylamidopropyldimethyl amine. Preparation of alkylamidopropyldimethyl amine of Formula II: The alkylamidopropyl amine can be obtained by reacting stoichiometric amounts of fatty acids with 3-/V,/V-dimethylaminopropylamine or aminolysis of triglycerides with the same amine. Either route works very well and the amidification is normally done at 130 — 140°C. (eq-1) Formula II Depending upon the fatty raw material used the amidoamine of Formula II may contain small amounts of unreacted triglyceride or fatty acids usually around 1 % by weight. The progress of the reaction is monitored by estimating the free fatty acid. The amidoamine generated from triglyceride obviously has stoichiometric quantities of glycerin liberated. At the end of the reaction (free fatty acid content of less than 1.0 %) the unreacted DMAPA is removed by washing the reaction mass by either water or even better, by brine solution. Another effective way of removing this small chain amine is by steam distillation. This is conveniently affected by passing steam in hot reaction mass at 120- 170°C, preferably at 170°C. This operation is continued till the residual DMAPA content is brought down to less than 350 ppm in the reaction mass of amidoamine of Formula II (eq-1). Reaching of desired levels of free DMAPA is confirmed by ion chromatographic analysis using cation exchange column. The low levels of free DMAPA in the alkylamidopropyl amine (Formula II) ensures that the corresponding betaine (Formula III) that gets formed in the second step always remains at levels less than 150 ppm in the final amidobetaine composition. 9 Preparation of alkylamidopropyl betaine of Formula I: In the present invention the quaternization of amidoamine of Formula II is done by reacting 1.0 mole of amidoamine with 1.01 to 1.05 mole of sodium monochloroacetate at the temperature of 80 - 85°C while maintaining pH between 7.5 - 8.0 by adding sodium hydroxide solution (45 %). The amount of water that is usually taken in this step is to keep the solids content of the reaction mass around 38 to 40 % by weight. The progress of the quaternization reaction is monitored by estimating the chloride ion liberated during the reaction as well as by estimating the unreacted amidoamine. (eq-2). Both analytical parameters are used to ensure the completion of quaternization with free amidoamine around 0.1 % by weight. Formula I Determination of free alkylamidopropyl amine from aqueous betaine composition is done by extracting and then titrating it against standard acid using potentiometry. Once the free alkylamidopropyl amine content of the reaction mass is confirmed to be less than 0.1 % then the temperature of the reaction mass (with the solids content 36 % or above by weight) is raised from 85°C to 95°C and the pH is raised to 10 - 10.5 and the whole mass is stirred for four additional hours. This step is essential for the destruction of unreacted sodium monochloroacetate and to ensure that free sodium monochloroacetate is less than 5.0 ppm. This can also be conveniently done at higher temperature (100 to 140°C) under pressure for quicker destruction of trace levels of sodium monochloroacetate. Free sodium monochloroacetate content is determined by ion chromatography of the 'solid phase extracted' betaine composition using anion exchange column. The two other impurities e.g. free DMAPA and the betaine arising out of DMAPA (Formula III, eq-3) are again conveniently analyzed by ion chromatography using cation exchange column. Finally, the pH of the reaction mass is adjusted to 4.5 to 10 6.5 by phosphoric acid or citric acid and is then cooled while stirring. Adjustment of solids content to at least 36 % gives clear, colorless, flowable amidobetaine composition. ,ONa TTVT. ^ ^ ^ eq-3 O NH2 + CI ]f ► H2N The CAPB samples made from the above mentioned procedure were tested for taste on a scale of 0 to 5, zero being the tasteless, without any bitterness and the score of 5 being the bitterest. The samples (0.25 % active matter in water) were tested by a panel of 10 experts (with sensitive taste buds and high olfactory sense) that were specially trained for this 'tasting exercise'. The commercial amidobetaines from various suppliers world over for personal care applications were found to have score of 4 to 5. The samples of CAPB from ten different experiments generated as per the process and specifications described herein in the present application had an average score of 1.0. This also established the repeatability and consistency of the improved process of the present invention (see Example I, Tables I and II). The tooth paste formulation made from CAPB of the present invention was found to be of much superior taste compared to tooth paste formulation made from commercial CAPB for personal care (skin and hair) applications. The tooth paste formulations for the comparison purposes were made without any sweetener to enhance the effect of CAPB on the 'taste' of the formulation (see Example I, Table III) The amidobetaines can replace the irritant, expensive anionic surfactants like SLS partially or completely in an oral care formulation. It is also possible to create high active compositions of the amidobetaine of Formula I wherein the taste is considerably improved due to the lowering of the bitter tasting li impurities. The high active amidobetaine compositions suitable for oral care applications are prepared by extending above-mentioned methodology to high active amidobetaine procedures reported in the literature (US Pat 5,354,906). The details of the invention, its objects and advantages are explained hereunder in greater details in relation to non-limiting exemplary illustrations. The examples are merely illustrative and do not limit the teaching of this invention and it would be obvious that various modifications or changes in the procedural steps by those skilled in the art without departing from the scope of the invention and shall be consequently encompassed within the ambit and spirit of this approach and scope thereof. EXAMPLES Coco fatty acid amidoamine was prepared from coco fatty acid and 3-N, N-dimethylaminopropylamine. 3-A/,A/-Dimethylaminopropylamine is procured from BASF and sodium monochloroacetate is purchased from Clariant. Example I: Process for making cocoamidopropvl betaine composition containing 29 % of active matter of Formula I and total solids of 36 %.) ( Example 1 of Table I) The amidobetaine composition is synthesized by the following two steps. Step I- Synthesis of cocoalkvlamido propyl dimethyl amine Hydrogenated coco fatty acid (1980g, 9.16 mol) is heated with dimethylaminopropyl amine (DMAPA, 971 g, 9.52 mol) in the presence of butylated hydroxy toluene (14 g, 0.063 mol) at 170°C with continuous removal of water that is generated during the course of the reaction. The progress of the reaction is monitored by measuring the free 12 fatty acid content of the reaction mass and is continued till fatty acid level reaches less than 1.0 %. Steam is passed through this reaction mass at 170X for about 2 -3 hours during which time free DMAPA level is reduced to 332ppm. Free DMAPA content is determined by ion chromatography (the details are given below). Reaction mass is then cooled to room temperature and taken further for the second step of quaternization. Step II- Synthesis of coco alkyl amidopropyl betaine To a stirred mixture of coco fatty acid amidoamine from step I (300 g, 1.0 mole, tertiary nitrogen content of 4.61 %, acid value 2.5, free DMAPA 332 ppm), and water (320 ml) under nitrogen at 65°C, an aqueous solution of sodium monochloroacetate (311.6 g, 40 %, 1.07 moles) is added over a period of half an hour. The reaction mixture is stirred for 8 hours at 80 - 85°C by maintaining the pH between 7.5 to 8.2 with sodium hydroxide (45 % aqueous solution) and stirring is continued for 8 hours at 95°C while maintaining pH between 10 - 10.5. The reaction mass is then cooled and the pH is adjusted to 4.5 to 5.5 with phosphoric acid to give a clear product (982 g). The composition of this amidobetaine solution is as given below. Solids 35.5 % Amidobetaine (active matter) 29.03 % NaCI 5.35 % Fatty acid 0.30 % Amidoamine 0.09 % Sodium monochloroacetate Free DMAPA Aminopropyl dimethylamino betaine PH 5.2 The ion exchange chromatography is performed on Dionex DX-500 ion chromatograph equipped with quaternary gradient pump and a conductivity detector. Background conductivity suppression is achieved by self-regenerating suppressors CSRS and ASRS-Ultra. The sodium monochloroacetate is analyzed by anion exchange 13 chromatography (anion exchange column lonPac AS-12A with AG-12A guard column, mobile phase 10mN NaOH, 1.5 ml/ min) and free DMAPA and aminopropyl dimethlamino betaine are analyzed by cation exchange chromatography (cation exchange column lonPac CS-12A with CG-12A guard column, mobile phase 20mN sulphuric acid, 1.0 ml/ min). Amidobetaine samples are suitably diluted and solid phase extracted using octadecyl silane cartridges (Accubond from J & W) before injecting them on the ion exchange column. For chromatographic analysis of compound of Formula III, the standard pure Formula III was synthesized and characterized. This experiment is listed as example 1 in Table I. Nine other experiments have been performed and the results are given in Table I. The CAPB samples made from the above mentioned procedure are tested for taste on a scale of 0 to 5, zero being the tasteless, without any bitterness and five being the bitterest. The samples (0.25 % active matter in water) are tested by a panel of 10 experts (with sensitive taste buds and high olfactory sense) that are specially trained for this 'tasting exercise'. The analysis and the taste score are given in the following table. TABLE I Analysis of amidobetaine samples of the present invention. Experiment No. TotalSolids% ActiveMatter% Amidoamineof Formula IIppm Impurity ofFormula 111ppm DMAPA ppm SMCA ppm Taste score 1 35.5 29.03 0.09 139 1.3 1.5 1 2 36.03 29.1 0.08 120 Nil 1.5 1 3 35.9 29.10 0.06 100 1.3 2.4 1 4 35.9 29.00 0.09 125 3.0 3.0 1 5 36.1 29.06 0.06 124 1 1.0 1 6 36.0 29.1 0.09 118 2.1 2.0 1 14 7 36.06 29.1 0.06 129 1.2 3.0 1 8 35.90 29.01 0.06 98 1.3 nil 1 9 36.00 28.92 0.05 130 1.3 1.4 1 10 35.90 29.01 0.06 111 nil 1.3 1 On analysis of commercially available CAPB samples from global manufacturers ( 28-29 % active ) for personal care applications, the impurity of Formula III, aminopropyl dimethylamino betaine, is found to be in range of 500 to 3000 ppm whereas alkylamidoamine of Formula II is found to be in the range of 2000 to 5000 ppm (Table II). TABLE II Analysis of commercially available amidobetaine samples (CAPB) Sample Code Total Solids % Active Matter % Amidoamine of Formula II ppm Impurity ofFormula III ppm DMAPA Ppm SMCA ppm Taste score A 35.5 29.4 0.40 4000 1.3 2.4 5 B 36.03 29.4 0.30 3500 2.8 4.4 4 C 35.9 29.14 0.46 800 1.3 3.0 4 D 35.9 29.23 0.32 1025 3.0 4.0 5 E 36.1 29.30 0.36 3050 3.0 6.0 5 The commercial samples of cocoamidopropyl betaine (global manufacturers) for personal care have been rated with a score of 4 to 5 uniformly since all of them have been found to be significantly bitter. As against this the cocoamidopropyl betaine samples of the present invention have been rated with a score of 1 uniformly. A toothpaste formulation was made using amidobetaine of the present invention and compared with the toothpaste formulation made from commercially available 15 amidobetaine for hair care and skin care. Both toothpastes were used by a panel of seven individuals. The taste scores were recorded on a scale of 1 to 10. Taste while brushing as well as after brushing was taken into consideration. The tooth pastes were made using the following formulation. Glycerin 45 % Calcium carbonate 2 % Sodium benzoate 0.3 % CAPB 2.0 % Water to make 100% TABLE III Taste scores for toothpastes Taste panelist no. 1 2 3 4 5 6 7 Average taste score Tooth paste with CAPB (commercial grade) 6 10 10 6 6 6 7 7.2 Tooth paste with CAPB (present invention) 4 3 6 4 4 2 3 3.7 Example II: Process for making cocoamidopropyl betaine composition containing 35 % of active matter of Formula I and total solids of 47 %. It is made by the two-step procedure. The amidoamine of Formula II is obtained from step of Experiment I. 16 To a stirred mixture of cocofatty acid amidoamine (from step I of Example I, 300 g, 1.0 mole, tertiary nitrogen content of 4.6 %, acid value 2.5, free DMAPA 332 ppm), glycerin (31.5 g) and water (320 ml) under nitrogen at 65°C, an aqueous solution of sodium monochloroacetate (311.6 g, 40 %, 1.07 moles) is added over the period of half an hour. The reaction mixture is stirred for 8 hours at 80 - 85°C by maintaining the pH between 7.5 to 8.2 with sodium hydroxide (47 % aqueous solution). Cocoyl glycine (6 g) was then added to the reaction mixture and stirring is continued for 8 hours at 95°C while maintaining pH between 10 - 10.5. The reaction mass is cooled and the pH is adjusted to 4.5 to 5.5 with phosphoric acid. The clear product (982 g) so formed has the following composition. Solids 47.2 % Amidobetaine 35.2 % NaCI 6.9 % Fatty acids 0.8 % Cocoyl glycine 0.6 % Glycerin 3.2 % Amidoamine 0.1 % Sodium monochloroacetate Free DMAPA Aminopropyl dimethylamino betaine pH 5.2 The amidobetaine composition of this experiment had taste score of 1. Advantages of the invention The amidobetaine composition of the present invention has the following advantages 17 1) The process of the present invention gives an amidobetaine composition that is most suitable for oral care applications (mouth rinses and tooth pastes) due to its significantly less bitter taste compared to commercially available CAPB for personal care applications. 2) The amidobetaine of the present invention allows use of a number powerful cationic antimicrobial agent in oral care formulations. 3) The amidobetaine of the present invention can replace anionic surfactants (that are irritant, expensive and incompatible with cationic actives) partially or totally. 4) Using the process of the present invention a high active, self preserving amidobetaine composition (45 % solids minimum, 37 % betaine content minimum) for oral care can also be made by incorporating other anionic surfactants like sodium lauroyl sarcosinate or sodium cocoyl glycinate (0.5 to 3 %) that are very widely used in dental care products. (US patent application No. 11/010,762 filed on Dec 12th 2004, US pat 5,354,906) 5) The process of the present invention yields amidobetaine composition with the lowest possible impurity level with less than 5.0 ppm of free sodium monochloroacetate and N,N- dimethylpropyl amine and with less than 150 ppm of aminopropyl betaine, the totally undesirable impurities that contribute to the bitter taste of the product. We claim 1. An aqueous amidobetaine composition comprising from 28 to 30 % by wt. of a betaine of the general Formula I, 18 Formula I in which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture, which, on the average, corresponds to coconut fatty acids, an amidoamine of not more than 0.1 % by weight, a free fatty acid less than 0.5 % by weight, 0 to 4 % by weight of glycerin, based on composition, less than 5 ppm of free sodium monochloroacetate and, less than 150 ppm of aminopropyl dimethylamino betaine ( Formula III), Formula III less than 5 ppm of free DMAPA wherein the composition has a solids content of at least 36 % by weight and a pH of 4.5 to 6. 2. An aqueous self-preserving high active amidobetaine composition comprising from 35 to 37 % by wt. of a betaine of Formula I, 19 in which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture, which, on the average, corresponds to coconut fatty acids, an amidoamine of not more than 0.1 % by weight, either a free fatty acid or A/-acyl a-amino acids less than 3 % by weight wherein alkyl group of fatty acids or A/-acyl a-amino acids is selected from C 8 to C18, 0 to 4 % by weight of glycerin, based on composition, less than 5 ppm of free sodium monochloroacetate and, less than 180 ppm of aminopropyl dimethylamino betaine, less than 5 ppm of free DMAPA wherein the composition has a solids content of at least 45 % by weight and a pH of 4.5 to 6. 3. The process for the preparation of amidobetaine (Formula I), Formula I in which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture, which, on the average, corresponds to coconut fatty acids, comprising steps of; 20 (i) reacting stoichiometric amounts of fatty acids with 3-N,N-dimethylaminopropylamine or aminolysis of triglycerides with the same amine to yield amidoamine of Formula II wherein the unreacted 3- N,N-dimethylaminopropylamine is removed by washing with aqueous solution or by steam distillation till free 3- /V, N-dimethy!aminopropylamine is less than 350 ppm; Formula II wherein, R of Formula II is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture which, on the average, corresponds to coconut fatty acids alkyl group; (ii) reacting purified alkyiamldopropyidimethyl amine of step (i) with stoichiometric quantities of sodium monochloroacetate at a temperature of 80-85°C and maintaining the pH between 7.5-8.0, ensuring the completion of quatemization with free amidoamine (Formula II) about 0.1 % by weight, raising the pH to between 10 to 10.5 and maintaining the temperature of between 90 - 98°C for a period of 4 - 8 hours and thereafter adjusting the pH to 4.5 to 6.0 with phosphoric acid or citric acid. 4. A process for the preparation of amidobetaine as claimed in claim 3 wherein the steam distillation is carried out by passing steam at the temperature of about 120°C to about 170°C. 21 Abstract An aqueous composition for oral care application comprising solution of an amidobetaine of the following general Formula I is disclosed; in which R is an alkyl of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture group which, on the average, corresponds to coconut fatty acids, wherein the solution has a solids content of 36 % by weight, a pH of 4.5 to 6, an alkylamidopropyldimethyl amine content of not more than 0.1 % by weight, and a free fatty acid content less than 0.5 % by weight, sodium chloride content of 6.0% max and dimethylaminopropylamino betaine (from A/,/V-dimethyl amino propyl 1,3-diamine (DMAPA) and monochloroacetic acid) content of 150 ppm max, free sodium monochloroacetic acid content of 5 ppm max and free /V,/V-dimethylamino propyl 1,3-diamine content of 5.0 ppm max. Amidobetaine composition of higher active matter content (total solids 45 %) for oral care application is also disclosed. Dated this 1SI Day of July 2005. ASHWINI SANDU OF S. MAJUMDAR & CO. Applicants' Agent 22

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