Title of Invention

COMPOSITIONS CONTAINING QUATERNARY AMMONIUM COMPOUND

Abstract

This invention relates to preparation of quaternary ammonium compound & their application in detergent / cleaning I cosmetic formulations. The molecules presented in this invention do provide a multifunctional surfactant so that same surfactant is attributed with different functional requirement of the formulation. Examples are Cleaning & conditioning, Supper fattening & foaming, Viscosity boosting & mild ness synergy etc.

Full Text

FORM 2 THE PATENTS ACT, 1970 (39 Of 1970) COMPLETE SPECIFICATION (See Section 10: Rule 13) TITLE A process of preparing a surfactant composition containing quaternary ammonium compound" APPLICANT Galaxy Surfactants Limited C-49/2, TTC Industrial Area, Pawne, Navi-Mumbai 400 703, Maharashtra, India. A Public Limited Company Registered under Company's Act -1956 The following specification particularly describes the nature of the invention and the manner in which it is to be performed:- " A process of preparing a surfactant composition of the formula containing quaternary ammonium compound" 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. R2, R3 can be C1 to C3 alkyl group, • R1 & R4 can be Aliphatic alkyl (C2 to C22) or aromatic. They can be same or different. • R4 can be RCOO", mineral acid like CI", PO4", phenolic OH , Cinnamic etc. Field of invention: The present invention relates to usage of quaternary ammonium compounds. This relates & not limited to usage for multi functional quaternary ammonium compound formulations. Examples of reduced Zein values signifying reduced irritancy, thus more skin friendly molecules, having anti bactericidal, cleaning & wetting property in one molecule, thus unique usage for as surface cleaners. Having conditioning & cleaning properties in a same molecule for personal care. Boosting foam as well as viscosity in surfactant systems used for personal care formulations. Other usage including detergent and cleaning formulations are also unique. 1 Back ground of the invention : Quaternary ammonium compound have been use since long time. The positive Nitrogen also imparts many useful properties to the compound. Few of them are substantivity 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 apart from the conventional properties of quaternary compounds. Present invention pertains to salts of quaternary 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 quaternary nitrogen covalently or ionically, thus imparting many more important properties to the molecule. The basic quaternary ammonium nitrogen can be ionically attached with another fatty alky acids or aromatic acid or mineral acid group by netralisation 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 quarternisation or after the quatemisation 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 also quotes its usage 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. 2 Objects of the invention: The inventors of the present patent further this art by introducing, alkyt or aromatic chain or acid radical (anion) in the molecule using strong basisity of the quaternary ammonium compound. This technique enhance the functional properties of the molecule several time over. Thus the present invention pertains to " usage of quaternary ammonium base salts in wide range of applications" as illustrated in example. The application include usage of compounds of invention as antibacterial, anti fungal, wetting agent, cleaning agent, foam booster, viscosity booster. Irritancy reducer etc. Summery of the invention: New set of quaternary ammonium compounds is made. In process, the scope for using the compound for multi tasking has increased. The same compound can be used as say sunscreen as well as surfactant function or sunscreen & conditioning purpose has been proposed. The usage as more effective viscosity booster for AOS based liquid formulation is also proposed. Formulation data of bath soap, shampoo and floor cleaner is also presented. Detailed descriptions & examples : 3 A process of preparing a Surfactant composition containing Quaternary ammonium compounds of the formula for use in a cosmetic / detergent compositions. 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. R2, R3 can be C1 to C3 alkyl group, • R1 & R4 can be Aliphatic alkyl (C2 to C22) or aromatic. They can be same or different • R4 can be RCOO", mineral acid like CI", PO4", phenolic OH , Cinnamic etc.Reacting coco amido propyl amine is mixed with water, under heating at the range of 15-50°C temperature followed by purging N2 gas by maintaining a pressure for a period of 2-10min. Examples: 1 1110 grams of stripped (C12-C16) coco amido propyl amine is mixed with 3210 grams of water . The same is heated to 20 °C. Nitrogen gas is purged through it for 5 minutes. Initial pressure of 0.5 kg of nitrogen was given.. 150 grams of EO was added to this mass by maintaining the temperature between 20 to 40 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Examples: 2 1300 grams of coco (C8 to C 18) amido propyl amine is mixed with 4585 grams of water. The same is heated to 25 °C. Nitrogen gas is purged through it for 5 minutes to drive off air. Initial pressure of 0.5 kg of nitrogen was given.. 175 grams of EO was added to this mass by maintaining the temperature between 25 to 50 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Examples: 3 790 grams of mixture of C16 & C18 fatty amido propyl amine is mixed with 3395 grams of water. The same is heated to 30 °C. Nitrogen gas is purged through it for 5 minutes to drive off air. Initial pressure of 0.5 kg of nitrogen was given.. 100 grams of EO was added to this mass by maintaining the temperature between 30 to 50 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Examples: 4 1100 grams of dimethyl amine is mixed with 2250 grams of water. The same is heated to 30 C. Nitrogen gas is purged through it for 5 minutes to 4 drive off air. Initial pressure of 0.5 kg of nitrogen was given.. 860 grams of EO was added to this mass by maintaining the temperature between 30 to 50 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Examples: 5 905 grams of dimethyl amine is taken. The same is heated to 30 °C. Nitrogen gas is purged through it for 5 minutes to drive off air. Initial pressure of 0.5 kg of nitrogen was given.. 708 grams of EO was added to this mass by maintaining the temperature between 30 to 50 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Example 6: 800 grams of mixture of distilled palm fatty acid (C16 & C18 fatty with iodine value of 38 ) amido propyl amine is mixed with 3570 grams of water. The same is heated to 30 °C. Nitrogen gas is purged through it for 5 minutes to drive off air. Initial pressure of 0.5 kg of nitrogen was given.. 90 grams of EO was added to this mass by maintaining the temperature between 30 to 50 degree. During the procedure the reaction pressure was monitored at 5 kgs maximum. Preparation of neutralized salts of quaternary ammonium compounds: After preparing a quaternary compounds with one alkyl chain the compounds were treated with many mineral acids, long chain alkyl fatty acids or aromatic acids, so as to enhance there properties for different end use. Example 7: 200 grams Quaternary ammonium compounds of example 1 was taken in a glass reactor. 30 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 reached, the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 207 ml of foam indicating good performance properties. Example 8: 200 grams Quaternary ammonium compounds of example 1 was taken in a glass reactor. 58 grams of water and 40 Grams of distilled palm fatty 5 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. The product has been analysed for foam by Ross Mile column & found to 211 ml of foam indicating good performance properties. Example 9: 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 25 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. The product has been analysed for foam by Ross Mile column & found to 217 ml of foam indicating good performance properties. Example 10: 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 32.7 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 8.3 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 211 ml of foam indicating good performance properties. Example 11: 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 32.3 Grams of mixture of C16 & C18 fatty 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 8.3 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 208 ml of foam indicating good performance properties. Example 12: 200 grams Quaternary ammonium compounds of example 6 was taken in a glass reactor. 17 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 6 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 217 ml of foam indicating good performance properties. Example 13: 200 grams Quaternary ammonium compounds of example 6 was taken in a glass reactor. 22.0 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 8.3 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 211 ml of foam indicating good performance properties. Example 14: 200 grams Quaternary ammonium compounds of example 6 was taken in a glass reactor . 21.8 Grams of mixture of C16 & C18 fatty 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 8.3 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 208 ml of foam indicating good performance properties. Example 15: 200 grams Quaternary ammonium compounds of example 3 was taken in a glass reactor. 16.58 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 8.4 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 209 ml of foam indicating good performance properties. Example 16: 200 grams Quaternary ammonium compounds of example 3 was taken in a glass reactor. 21.3 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 8.3 is, the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 208 ml of foam indicating good performance properties. 7 Example 17 : 200 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor .21.8 Grams of mixture of C16 & C18 fatty 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 8.3 is , the mixing is stopped. The product has been analysed for foam by Ross Mile column & found to 208 ml of foam indicating good performance properties. Example 18: 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. The product has been analysed for foam by Ross Mile column & found to give 150 ml of foam indicating good foam performance. The substantivity of hair is measured by method described here in. When incorporated in soap at 2% level & soap is tested on human hair, it can be seen that 29.9 milli grams of product is substantiated on hair. The product has molar extinction coefficient of 25717 with max. wavelength of adsorption of 287.9 nm. This data indicates that this molecule can function as water soluble sunscreen agent for UVB range protection, surfactants & conditioner as well when used in hair care product. Example 19: 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. The product has been analysed for foam by Ross Mile column & found to 176 ml of foam indicating good performance properties. The Minimum Inhibitory Concentration (MIC) is 40 & 12 for Escherichia coli and Staphylococcus aureus. This gives us a molecule with surfactants base & antibacterial properties together. Example 20: (Dimethyl diethyl ammonium salt of coco fatty acid) 25 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor. 25.4 Grams of mixture of coco fatty acid and 135 grams 8 of water is 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. The product has been analysed for foam by Ross Mile column & found to 222 ml of foam indicating good performance properties. Example 21: (Dimethyl diethyl ammonium salt of Stearic acid) 25 grams Quaternary ammonium compounds of example 2 was taken in a glass reactor . 33.2 Grams of stearic acid (C16 & C18 mixed commercial blend) and 155 grams of water is 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. The product has been analysed for foam by Ross Mile column & found to 215 ml of foam indicating good performance properties. Multi functional performance of the invention: 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 formulation. For illustration compound of example 10 was used 9 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. 10 Hard surface cleaning formulations: A formulation is made containing 5.5% of active solution of example 19. No other surfactants was used in this test formulation. The 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. 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. Thus even after increase in inoculumn the test compound was found to be more effective. Methods of analysis: Foaming : Foaming is done using Ross Miles column as prescribed in BIS 5785:1970 pH : pH of 5% solution is measured using pH meter. The solution is made in distilled water. 11 Viscosity: Viscosity was measured using Brook Field Viscometer model 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 + / - 2deg. Cent. Check for the growth of the organism. Advantages of the invention The main advantage of the invention is to provide a molecule which can be used as multi functional entity in surfactant formulations. This will enable to have one component to do multi functional job. A same surfactants can be used in a formulation to do • Act as cleaning detergent • Hair conditioning • Reduce Skin irritancy potential of other component of formulation • To foam boosting of the formulation without using conventional foam booster • To reduce usage of sodium chloride for viscosity boosting • Anti-bacterial agent is floor cleaner formulations. 12 Claims of the inventions: We claim:- 1. A process of preparing a Surfactant composition containing Quaternary ammonium compounds of the formula for use in a cosmetic / detergent compositions. 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. R2, R3 can be C1 to C3 alkyl group, • R1 & R4 can be Aliphatic alkyl (C2 to C22) or aromatic. They can be same or different. • R4 can be RCOO", mineral acid like CI", PO4", phenolic OH , Cinnamic etc. Reacting coco amido propyl amine is mixed with water, under heating at the range of 15-50°C temperature followed by purging N2 gas by maintaining a pressure for a period of2-10min. 2. A process as claimed in claim - 1, where in the R1 cocofatty acid, R2/R3 = CH3. R4 can be cocofatty acid. can be 3. A process as claimed in claim - 1, where in the R1 can Undecylenic acid, R2, R3 = CH3. R4 can be cocofatty acid. 13 be 4. A process as claimed in claim - 1, where in the R1 can be cocofatty acid, R2, R3 = CH3. R4 can be Para methoxy cinnamic acid. 5. A process as claimed in claim - 1, where in the R1 can be cocofatty acid, R2, R3 = CH3. R4 can be Benzophenone -3. 6. A process as claimed in claim - 1, where in the R1 can be cocofatty acid, R2, R3 = CH3. R4 can be Benzophenone -4. 7. A process as claimed in claim - 1, where in amino compound is Dimethyl amino propyl amine. 8. A process as claimed in claim - 1, wherein amino compound is Dimethyl amine. 9. A process as claimed in claim-1, wherein the said compound used as a viscosity booster in liquid surfactants blends in proportion of 0.5 to 10%. 10. A process as claimed in claim-1, wherein the said compound used as a foam booster in liquid surfactants blends in proportion of 0.5 to 10%. This day, May, 200 Authorised Signatory. Name: Dilip Mhatre Manager QA (one of the inventor) 14 For Galaxy Surfactants Limited

Documents:

482-mum-2003-abstract(granted)-(23-06-2005).doc

482-mum-2003-abstracts(23-06-2005).pdf

482-mum-2003-cancelled pages(23-06-2005).pdf

482-mum-2003-claims(granted)-(23-06-2005).doc

482-mum-2003-claims(granted)-(23-06-2005).pdf

482-mum-2003-correspondence(23-06-2005).pdf

482-mum-2003-correspondence(ipo)-(15-06-2005).pdf

482-mum-2003-form 1(13-05-2003).pdf

482-mum-2003-form 2(granted)-(23-06-2005).doc

482-mum-2003-form 2(granted)-(23-06-2005).pdf

482-mum-2003-form 3(21-05-2004).pdf

482-mum-2003-form 4(21-05-2004).pdf

482-mum-2003-form 5(21-05-2004).pdf