Question 1 page of manual: Conclusion Dibenzalacetone can be synthesized from benzaldehyde and acetone by Aldol condensation. The experiment was fairly successful as the percent yield indicated the experiment was sufficient. The IR graph and the Rf value results also supported the completion of the reaction. References: Mahrwald, R. Modern Aldol Reactions 1, 2. Smith, M. Advanced Organic Chemistry 5th ed. These silicone emulsifiers are typically organically modified organopolysiloxanes, also known to those skilled in the art as silicone surfactants.
Useful silicone emulsifiers include dimethicone copolyols. These materials are polydimethyl siloxanes which have been modified to include polyether side chains such as polyethylene oxide chains, polypropylene oxide chains, mixtures of these chains, and polyether chains containing moieties derived from both ethylene oxide and propylene oxide. Other examples include alkyl-modified dimethicone copolyols, i. Still other useful dimethicone copolyols include materials having various cationic, anionic, amphoteric, and zwitterionic pendant moieties.
It is recognized that positional isomers of these copolyols can be achieved. Nonlimiting examples of dimethicone copolyols and other silicone surfactants useful as emulsifiers herein include polydimethylsiloxane polyether copolymers with pendant polyethylene oxide sidechains, polydimethylsiloxane polyether copolymers with pendant polypropylene oxide sidechains, polydimethylsiloxane polyether copolymers with pendant mixed polyethylene oxide and polypropylene oxide sidechains, polydimethylsiloxane polyether copolymers with pendant mixed poly ethylene propylene oxide sidechains, polydimethylsiloxane polyether copolymers with pendant organobetaine sidechains, polydimethylsiloxane polyether copolymers with pendant carboxylate sidechains, polydimethylsiloxane polyether copolymers with pendant quaternary ammonium sidechains; and also further modifications of the preceding copolymers containing pendant C2-C30 straight, branched, or cyclic alkyl moieties.
Other nonlimiting examples of dimethicone copolyols also include lauryl dimethicone copolyol, dimethicone copolyol acetate, diemethicone copolyol adipate, dimethicone copolyolamine, dimethicone copolyol behenate, dimethicone copolyol butyl ether, dimethicone copolyol hydroxy stearate, dimethicone copolyol isostearate, dimethicone copolyol laurate, dimethicone copolyol methyl ether, dimethicone copolyol phosphate, and dimethicone copolyol stearate.
See International Cosmetic Ingredient Dictionary. Fifth Edition, Dimethicone copolyol emulsifiers useful herein are described, for example, in U. Dahms, et al. Carlotti et al. Dispersion Science And Technology. Smid-Korbar et al. International Journal of Cosmetic Science, 12, ; and D.
Krzysik et al. Among the non-silicone-containing emulsifiers useful herein are various non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated derivatives of C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated ethers of C1-C30 fatty alcohols, polyglyceryl esters of C1-C30 fatty acids, Cl- C30 esters of polyols, C1-C30 ethers of polyols, alkyl phosphates, polyoxyalkylene fatty ether phosphates, fatty acid amides, acyl lactylates, soaps, and mixtures thereof.
Nonlimiting examples of these non-silicon-containing emulsifiers include: polyethylene glycol 20 sorbitan monolaurate Polysorbate 20 , polyethylene glycol 5 soya sterol, Steareth, Ceteareth, PPG-2 methyl glucose ether distearate, Ceteth- 10, Polysorbate 80, cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate, Polysorbate 60, glyceryl stearate, PEG- stearate, polyoxyethylene 20 sorbitan trioleate Polysorbate 85 , sorbitan monolaurate, polyoxyethylene 4 lauryl ether sodium stearate, polyglyceryl-4 isostearate, hexyl laurate, steareth, ceteareth, PPG-2 methyl glucose ether distearate, ceteth- 10, diethanolamine cetyl phosphate, glyceryl stearate, PEG- stearate, and mixtures thereof.
Examples of suitable carriers comprising oil-in-water emulsions are described in U. A preferred oil-in-water emulsion, containing a structuring agent, hydrophilic surfactant and water, is described in detail hereinafter. Without being limited by theory, it is believed that the structuring agent assists in providing rheological characteristics to the composition which contribute to the stability of the composition. The structuring agent may also function as an emulsifier or surfactant.
Preferred compositions of this invention comprise from about 0. The preferred structuring agents of the present invention are selected from the group consisting of stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, stearic acid, palmitic acid, the polyethylene glycol ether of stearyl alcohol having an average of about 1 to about 21 ethylene oxide units, the polyethylene glycol ether of cetyl alcohol having an average of about 1 to about 5 ethylene oxide units, and mixtures thereof.
More preferred structuring agents of the present invention are selected from the group consisting of stearyl alcohol, cetyl alcohol, behenyl alcohol, the polyethylene glycol ether of stearyl alcohol having an average of about 2 ethylene oxide units steareth-2 , the polyethylene glycol ether of stearyl alcohol having an average of about 21 ethylene oxide units steareth , the polyethylene glycol ether of cetyl alcohol having an average of about 2 ethylene oxide units, and mixtures thereof.
Even more preferred structuring agents are selected from the group consisting of stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, steareth-2, steareth, and mixtures thereof.
The surfactant, at a minimum, must be hydrophilic enough to disperse in water. Suitable surfactants include any of a wide variety of known cationic, anionic, zwitterionic, and amphoteric surfactants. See, McCutcheon's, Detergents and Emulsifiers. Patent 5,,; U. Patent 4,,; and U. Such surfactants may be used as a component of the emulsion form of the present compositions or they may be used in alternative product forms, e.
Anionic surfactants are preferred for use in the present compositions as part of the carrier system. These anionic surfactants may be lathering or non-lathering, depending on the desired final product form. Nonlimiting examples of anionic lathering surfactants useful in the compositions of the present invention are disclosed in McCutcheon's, Detergents and Emulsifiers, North American edition , published by The Manufacturing Confectioner Publishing Co.
The hydrophobic phase is dispersed in the continuous aqueous phase. The hydrophobic phase may contain water insoluble or partially soluble materials such as are known in the art, including but not limited to the silicones described herein in reference to silicone-in-water emulsions, and other oils and lipids such as described above in reference to emulsions.
The antimicrobial compositions and products of the subject invention, including but not limited to lotions, cleansers, creams, aqueous solutions, alcohol gels, tissues, wipes, etc. As used herein, "emollient" refers to a material useful for the prevention or relief of dryness, as well as for the protection of the skin.
A wide variety of suitable emollients are known and may be used herein. Sagarin, Cosmetics. Science and Technology. A preferred emollient is glycerin. Glycerin is preferably used in an amount of from or about 0. Lotions and creams according to the present invention generally comprise a solution carrier system and one or more emollients. Ointments may further comprise a thickening agent, such as described in Sagarin, Cosmetics, Science and Technology.
As used herein, the term "foundation" refers to a liquid, semi-liquid, semi-solid, or solid skin cosmetic which includes, but is not limited to lotions, creams, gels, pastes, cakes, and the like. Typically the foundation is used over a large area of the skin, such as over the face, to provide a particular look. Foundations are typically used to provide an adherent base for color cosmetics such as rouge, blusher, powder and the like, and tend to hide skin imperfections and impart a smooth, even appearance to the skin.
Foundations of the present invention include a dermatologically acceptable carrier for the pyroglutamic acid and metal salt and may include conventional ingredients such as oils, colorants, pigments, emollients, fragrances, waxes, stabilizers, and the like. Exemplary carriers and such other ingredients which are suitable for use herein are described, for example, in copending patent application Serial No. Canter, Brain D. Barford, and Brian D. Hofrichter, and U. EH The antimicrobial compositions of the present invention exhibit a pH of from about 1 to about 7.
More preferably, the pH of the present compositions ranges from about 1. In the most preferred embodiment, the pH of the compositions is from about 2 to about 4. Without being limited by theory, it is believed that such an acidic environment protonates the viral capsid shell, which initiates a conformational change that irreversibly inactivates the virus, rendering the virus incapable of initiating infection.
This effect synergizes with the metal salt and acid structure to produce the desired immediate and residual anti-viral and antibacterial efficacy which is key to the present compositions.
Optional Components The compositions of the present invention may contain a variety of other ingredients such as are conventionally used in a given product type provided that they do not unacceptably alter the benefits of the invention.
The CTFA Cosmetic Ingredient Handbook, Second Edition describes a wide variety of nonlimiting cosmetic and pharmaceutical ingredients commonly used in the personal care industry, which are suitable for use in the compositions of the present invention. In any embodiment of the present invention, however, the actives useful herein can be categorized by the benefit they provide or by their postulated mode of action. However, it is to be understood that the actives useful herein can in some instances provide more than one benefit or operate via more than one mode of action.
Therefore, classifications herein are made for the sake of convenience and are not intended to limit the active to that particular application or applications listed.
Antimicrobial and Antifungal Actives The compositions of the present invention may comprise an antimicrobial or antifungal active. Such actives are capable of destroying microbes, preventing the development of microbes or preventing the pathogenic action of microbes.
A safe and effective amount of an antimicrobial or antifungal active may be added to the present compositions, preferably, from about 0. Table 1 and 2 Table 1. If contacted, remove with plenty of water.
In a medium size tube, mix 2mL of benzaldehyde with 15 drops of acetone, and leave it at room temperature for 5 minutes. Then, add the mixture to the ethanol-NaOH solution in small portions and stir with magnetic stirrer if available for 30 minutes. Chill the solution in an ice-water bath. Collect the yellow crystals by suction filtration and hand-dry them by pressing them between dry paper towels. Determine the weight of the dibenzalacetone product, its melting point, and the percent yield. Return the product to your instructor.
NOTE- The amounts of the reagents used in this reaction are very important to ensure the correct product forms. In a given example a student added twice as much acetone as the procedure called for. Since there would be such an excess of acetone the benzaldehyde would only see acetone and would not end up adding twice to any acetone molecules. This would give an end product of benzalacetone instead of dibenzalacetone.
Structure of dibenzalacetone 8. Answer in space provided. The product from the reaction will be a yellow precipitate. After the precipitate forms, place the flask in an ice water bath for 10 minutes. Clamp the flask to prevent it from tipping. Collect the solid using vacuum filtration.
Note: Be sure to record the mass of the filter paper before placing it in the vacuum funnel. Prepare to wash and dry the solid. Wash with cold distilled water. Rinse the solid with 5—8 drops of ethanol. Keep the vacuum filtration on for an additional 10 minutes to help air dry the solid.
Weigh the dried solid on the filter paper and record the mass to 0. Part II Recrystallization Monitor the temperature with a Wide-Range Temperature Probe or thermometer. Transfer your crude product to a test tube and add about 5 mL of ethanol. Use the minimum amount of solvent needed to dissolve your solid.
Crystals will not form if too much ethanol is used.
Prepare a sample in a capillary tube and determine the melting temperature of the sample: The methodology utilized to determine residual anti-viral efficacy is discussed below in the "Analytical Methods" section. Wade, L. The peak at cm-1 is an indication of the presence of the double bonds in the product, and the next weak signals are indicators of the presence of aromatic rings. This would give an end product of benzalacetone instead of dibenzalacetone.
The term "volatile" as used in this context refers to all other silicone oils. Patent 4,,; and U. A more detailed discussion of useful lipophilic skin moisturizers can be found in U.
Furthermore, the present invention relates to antimicrobial products which comprise the compositions of the present invention as well as kits which comprise such products.
The alkyl sulfates are typically made by the sulfation of monohydric alcohols having from about 8 to about 24 carbon atoms using sulfur trioxide or other known sulfation technique. Emulsions according to the present invention generally contain a solution as described above and a lipid or oil. These products range from personal cleansing products such as hand soaps to household cleaning products like disinfectant sprays and cleansers. Prepare to wash and dry the solid. International Journal of Cosmetic Science, 12, ; and D.
Generally, the pyroglutamic acid ester is present in a safe and effective amount such that equilibrium is established between the pyroglutamic acid, the pyroglutamic acid ester, and the alcohol component of the carrier of the present invention. These anionic surfactants may be lathering or non-lathering, depending on the desired final product form. More particularly, the metal salts include, but are not limited to, dermatologically acceptable metal chelates and salts like bishistidine complexes, bromides, chondroitin sulfate, chromites, cyanides, dipiocolinates, ethylhexanoates, glycerolate complex, methoxides, polyphosphonates, paraphenolsulfonates, perchlorates, phenolsulfonates, selenides, stearates, thiocyanates, tripolyphosphates, tungstates, phosphates, carbonates, para-aminobenzoate, paradimethylaminobenzoates, hydroxides, para- methoxycinnamate, naphthenates, stearates, caprates, laurates, myristates, palmitates, oleates, picolinates, pyrithiones, fluorides, aspartates, gluconates, iodides, oxides, nitrites, nitrates, phosphates, pyrophosphates, sulfides, mercaptopyridine- oxides e. Weldegirma, S. Thus at higher temperature in base the aldol reaction will go directly to the conjugated enone without any isolation of the aldol intermediate.
Obtain and wear goggles. Dispose of the capillary tubes as directed by your instructor. In this 3 experiment we will prepare the dibenzalacetone: 1,5-diphenyl-1,4-pentadienone. Collect the product by vacuum filtration. Slowly add acetone dropwise to the flask until the mass is about 0. Dispersion Science And Technology.
Exemplary carriers and such other ingredients which are suitable for use herein are described, for example, in copending patent application Serial No. The acidity of the organic species is large relative to most hydrogens that are bonded to carbon due to the resonance stabilization of the enolate that is formed. Weigh your product and determine percent yield. The carrier solution containing the pyroglutamic acid and metal salt can be applied directly to the surface to be treated or delivered via a suitable substrate.