Patent Application: US-201313792071-A

Abstract:
stable , bio - compatible , 1 , 2 , 4 - trioxolane compounds are produced and applied to living tissue , teeth , and hair , for the cosmetic purpose of bleaching or whitening .

Description:
any compound with a 1 , 2 , 4 - trioxolane functionality will have some degree of bleaching power , thus a virtually infinite variety of compounds could be created with some degree of bleaching properties . fig1 . depicts the formation of these embodiments , where the alkene substituents can be any alkyl group or proton . resulting in an ozonide of infinite variety . fortunately however , due to the many practical concerns regarding the synthetic process , the nature of the desired product , and the availability of unsaturated hydrocarbons ( alkenes ), the practical embodiments are more narrowly defined by fig2 . fig2 thus depicts the practical ramifications of this invention . fig2 shows that the alkene to be ozonated must have only two alkyl substituents , and these two substituents must be in a cis orientation . now the exact nature of these two cis - alkyl substituents thus complete the definition of the practical embodiments of this invention . r1 is an alkyl group of chain length c2 - c30 , and may contain other cis - alkene functionalities . r2 is an alkyl group of chain length c2 - c30 that may also contain an ester group or other functionality . the exact nature of these two r - groups is left undefined so as to allow for differing log p values ( log p value , a physical characteristic a pharmaceutical compound used to predict its behavior within biological systems ) and formulation characteristics . for example if aqueous formulations were desirable , then salts of the ozonide could be prepared . also , a specific log p value of the product could be targeted by manipulation of these r - groups . a specific embodiment of this invention is depicted in fig3 showing the chemical reaction where the cis - alkene methyl linoleate ( cas # 112 - 63 - 0 ) is converted to the methyl linoleate ozonide , a di - trioxolane , under the following reaction conditions : a 0 . 3m solution of methyl linoleate in hexane is maintained at − 30 c , before using a sintered glass gas impinger to pass an oxygen stream containing about 5 % ozone through the alkene solution . the effluent gas is monitored for the point when the ozone escaping the reaction is no longer being “ absorbed ” by the alkene solution . the reaction is very rapid and virtually quantitative , with & gt ; 80 % yields always expected . the hexane can then be thoroughly removed under vacuum ( recovered , re - distilled , and reused ) giving a product of sufficient quality for formulation and use . sources of methyl linoleate ( cas # 112 - 63 - 0 ) are available world wide as it is used for a very wide variety of applications from , metal cutting lubricants and ink solvents to food emulsifiers and emollients in skin products . as these compounds are subject to decomposition by both heat and light and should be stored in dark bottles , refrigerated , for best shelf life . it is this same “ decomposition ” that can better be described as activation for the purposes of bleaching . as is the case with peroxide compounds , the bleaching rate for 1 , 2 , 4 - trioxolane compounds can also be “ activated ” by either heat or by light , as depicted in fig4 ( taken from page 142 of baileys review ). and while the literature is vague for the specific wavelengths of light that activate the peroxide bond , wavelengths of between 375 and 500 nm have been used successfully for hydrogen peroxide and are expected to do the same with the peroxide bond in ozonides . i have found no examples in the literature for an ozonide , or trioxolane compound being used for cosmetic purposes . however i still feel i should make some comments about how ozonides differ from hydrogen peroxide as a bleaching agent , since hydrogen peroxide currently constitutes the overwhelming majority of treatments for the bleaching of teeth , skin and hair . trioxolane compounds can be considered to have a negative toxicity , as not only are they highly tolerated by biological tissue but they can also purge the tissue of unwanted pathogens , like fungus , viruses , bacteria , and parasites . hydrogen peroxide , on the other hand , is known to produce hydroxide radicals as the primary decomposition product . these hydroxide radicals are clearly the souse of tissue irritation produced by hydrogen peroxide treatments . this makes ozonides a much safer source of “ peroxide like ” whitening activity . one disadvantage of the specific embodiment disclosed in this document is that on weight per weight basis hydrogen peroxide will have significantly more bleaching power , as the molecular weight of hydrogen peroxide is 11 . 4 times less than that of the ozonide disclosed herein . hydrogen peroxide has a molecular weight of 34 , compared with a molecular weight of 390 amu for the particular embodiment described here . thus , if we assume the peroxide bond in the ozonide is of equal bleaching power to the peroxide bond in hydrogen peroxide , and with two peroxide bonds per molecule , then the ozonide will inherently have 6 times weaker , or milder , bleaching power . 1 criegee , rudolf ( 1975 ). “ mechanism of ozonolysis ”. angew . chem . int . ed . engl . 14 ( 11 ): 745 - 752 . 2 bailey , p . s ., “ ozonation in organic chemistry ”, volume 1 olefinic compounds . academic press , new york ( 1978 ). 3 neel , w . d ., u . s . pat . no . 925 , 590 ( july 1902 ) 4 knox , w . j ., u . s . pat . no . 1 , 210 , 949 ( january 1917 ) 5 johnson , c . c ., u . s . pat . no . 2 , 356 , 062 ( august 1944 ) 6 cronheim , g ., organic ozonides as chemotherapeutic agents , i & amp ; 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