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SYNTHETIC PHOSPHOBETAINES TECHNOLOGY (PHOENOTAINE C-35 / PHOENOTAINE D-35) Specialty phospholipids made from soy lecithin are used extensively in cosmetics for their ability to act as emulsifiers, lubricants, dispersing agents, and emollients. In recent years, they have assumed important roles in the formation of liposome dispersions used in fine cosmetic and drug applications. Phospholipids are excellent choices for cosmetic use since they are natural, toxicologically safe, and do not produce skin irritation or cause sensitization effects. The naturally occurring materials from soy while useful have some drawbacks in terms of formulation. They have some problems with ease of emulsification and applications. Phospholipids refers to compounds having one or more ionizable phosphate groups and one or more cationic groups. This term applies to compounds regardless of the number of these groups. Phosphobetaines are a specific type of phospholipids in which there is only one ionizable phosphate group and only one cationic group. Phoenix Chemical has undertaken a project aimed at providing Synthetic PhosphoBetaines (The SPB project). The use of synthetic organic chemistry to modify the basic properties of phospholipids has resulted in functional materials that can be used as replacements, enhancers, emulsifiers, and extenders of natural phospholipids. As one looks at the product line the natural product phosphatidyl choline needs to be kept in mind. Compounds in our SPB line need to be compared to this material. R C(O) O CH2 R'C(O) O CH CH3 H2C O P(O) O (CH2)2N+ CH3 O Phosphatidyl Choline CH3 It is important to note the functional groups present in phosphatidyl choline. It is the structural attributes of the molecule that determines the functionality. The molecule has (a) hydrophobic groups (the two acyl groups), (b) hydrophilic groups (the quat group and the phosphate group), and (c) the presence of the (+) and (-) groups in the same molecule make this material an amphoteric surfactant. This is quite significant when one realizes that 99% of all surfactant activities in the cell is carried out by amphoteric surfactants. This includes cell wall activities. Industrially, we use comparatively little amphoteric materials. Phoenix EPB Compounds (Ester PhosphoBetaines) Phoenix EPB compounds conform to the following structure: CH3 HO R C(O) O (CH2CH2O)X P(O) O CH2 CH CH2 -O N+R' CH3 These molecules have (a) two hydrophobic groups R and R’ at opposite ends of the molecule (gemini surfactants), (b) hydrophilic groups ( the quat group, the phosphate group and the polyoxyalkylene group), and (c) the presence of the (+) and (-) groups in the same molecule making this material an amphoteric surfactant and (d) an ester group. The molecule can be modified in terms of: (a) Hydrophobic Modification (b) Hydrophilic Modification (c) HLB Balance R and R’, “x” value ratios of (a) to (b) providing the formulator with new flexibility in making emulsions. PHOENIX AMIDO PHOSPHO BETAINES (APB) COMPOUNDS Phoenix APB compounds conform to the following structure: + O RCNH(CH2)3 CH3 N CH3 O CH2CHCH2O PONa OH 2 3Cl These molecules have (a) a hydrophobic group R, (b) hydrophilic groups (the quat group, and the phosphate group), and (c) the presence of the (+) and ( - ) groups in the same molecule making this material an amphoteric surfactant and (d) an amido group. The molecule can be modified in terms of: (a) Hydrophobic Modification (b) Hydrophyllic Modification (c) HLB Balance By modifying the R (alkyl) group one can modify either property providing the formulator with new flexibility in making emulsions. The conversion of the ester group into the more hydrolytically stable amido group provides wider formulation latitude. Phoenix synthetic phosphobetaines are propylene glycol free and unique in that they are monofunctional as compared to di and trifunctional phospholipids currently in the market. These products are covered by U.S. patent 6,180,806, entitled Glyceryl Phosphobetaine Compounds, issued January 30, 2001, to Phoenix Research Corp. Phosphobetaines are compatible with anionic surfactants such as sodium lauryl ether sulfate (SLES), forming a complex that enhances deposition on hair and contributes to hair conditioning and manageability. This effect is also postulated to take effect on the epidermis. Two materials are currently being offered; one is a Sodium Cocamidopropyl PGDimonium Chloride Phosphate and the other a Sodium Dilinoleamidopropyl PGDimonium Chloride Phosphate. Trade Name INCI CAS # EINECS PHOENOTAINE® C-35 Sodium Cocamidopropyl PG-Dimonium Chloride Phosphate 83682-78-4 280-518-3 Trade Name INCI CAS # PHOENOTAINE® D-35 Sodium Dilinoleamidopropyl PG-Dimonium Chloride Phosphate Not Assigned Amino phospholipids are recommended for use as extremely mild surfactants, especially in baby products such as shampoos, bath and shower gels, body wash, bath beads, and products used in personal care. ATTRIBUTES At 5% levels favorable properties contributed by PHOSPHOBETAINES in shampoos and bath products are: 1. Mildness 2. Counter irritant for SLES 3. Foam enhancement 4. Mild detergent 5. Conditioning TENTATIVE SPECIFICATIONS PHOENOTAINE® Appearance (@25°C) Solids (%) pH (10% in 25% IPA) Color (Gardner) Foreign Matter % NaCl C-35 Clear Yellow Liquid 37-39 6.0-8.0 6 Max Free Of 4.0 Min. D-35 Clear Amber Liquid 29-31 5-7 8 Max Free Of 5.0 Min. SOLUBILITIES PHOENOTAINE® C-35 D-35 Water s s Propylene Glycol s s IPA s s Mineral Oil i i Isopropyl Myristate i i Silicone Fluid i i s = Soluble i = Insoluble SAFETY DATA Skin irritation and skin sensitization data developed via RIPT studies with 50 human subjects follows: PHOENOTAINE® * Skin Irritation * Skin Sensitization C-35 Non-Primary Irritant Non-Primary Sensitizer D-35 Non-Primary Irritant Non-Primary Sensitizer * Studies conducted by AMA Labs., 216 Congers Rd. New City, NY 10956 02/28/03 Rev. 02/06/07 While the information herein is believed to be reliable, PHOENIX CHEMICAL, INC. does not guarantee its accuracy. Purchasers are urged to conduct their own tests. PHOENIX CHEMICAL, INC. warrants its materials, as described herein, shall conform to the written specifications for such materials. PHOENIX CHEMICAL, INC. makes no other warranty, either expressed or implied, as to the materials’ merchantability or fitness for purpose. In no event shall PHOENIX CHEMICAL, INC.’s liability for breach of this warranty exceed the purchase price of the material for which such breach is claimed. Nothing contained herein is intended as a recommendation to use PHOENIX CHEMICAL, INC. products so as to infringe any patent and no liability for customer’s violation of patent or other rights is assumed.