MXPA00008334A - Polymeric compounds and methods of formulating same - Google Patents

Abstract

A method for the preparation of compositions of poly(2-propenal, 2-propenoic acid), whereby the compositions exhibit one or more of the properties of increased stability, increased antimicrobial activity, reduced trans-dermal migration of low molecular weight components of the composition, and the formation of continuous antimicrobial film on substrates, the property or properties making the composition suitable forone or more of antimicrobial use, dermatological use, and/or use as an animal feed additive.

Description

POLYMERIC COMPOUNDS AND METHODS PABA _r? _ü__Jl_¿_ LCS IIZSIOS DESCRIPTION D? ____ ia_V? -_ CSOH The present invention relates to psiméricos compounds and methods to form them, the polymeric compounds have a polyacrolein sub-unit in the form of aldehyde, hydrate, hemiacetal or acetal and having biostatic or biocidal properties. More particularly, the present invention is directed to compositions containing the above-noted polymeric compounds and the biostatic and / or biocidal uses of these compositions. The widely based antimicrobial properties of polymers having the repeated polymer unit: ; or this unit in its hydrated, hemiacetal or acetal form, represented by the formula: wherein R is hydrogen or alkyl and n is an integer number of one or more that has been demonstrated above (International Patent Application Publication WO 88/04671). The compounds particularly described therein include poly (2-propenal, 2-propenoic acid). It has also been previously noted (Publication in International Patent Application WO 96/38186) that poly (2-propenal, 2-propenoic acid) is formed when the poly (2-propenal) non-polyacrolein aldehyde groups auto-oxidize partially to carboxyl groups. Additionally it was noted that the polymer is soluble in dilute aqueous bases, for example aqueous sodium carbonate. It is known that the antimicrobial compositions can be used as preservatives, or as the active ingredients in disinfectants, dermatological compositions that include formulations of sunscreens to antiseptic formulations, or in animal feed additives. Generally these antimicrobial compositions must: o be stable; or be effective in the destruction of microorganisms within a specified time; or to be safe, that is to be reasonably free of toxicity which may be caused by the transdermal migration of low molecular weight ingredients into the blood stream to manifest to the patient. antigenicity, allergy, irritation or inflammation; or have a minimal smell; Y . _, -. -? in some dermatological preparations, having the property of filtering the sun and minimizing the adverse dermatological effects of the generation of free radicals. Specifically, the antimicroi formulations. Anas applied to inanimate objects and skin are usually called disinfectants and antiseptics, respectively. Frequently, regulatory standards first demand that a disinfectant formulation be stable and second, that it destroy a selected amount of vegetative microorganisms within 10 minutes. That is, the antimicrobial activity of these compositions must be biocidal and rapid. The formulations described herein address substantially these goals, but frequently achieve more, for example by destroying extremely resistant bacterial spores within the usual 24-hour standard. It has now been found that the formulation of poly (2-propenal, 2-propenoic acid) simply by dissolving in dilute aqueous sodium carbonate, and then neutralizing to pH 7, provides a composition that does not always destroy microorganisms fast enough to satisfy the previous standards.

It is an object of the present invention to provide methods for preparing compositions comprising compounds of the type described by the prior art and in particular poly (2-propenal, 2-propenoic acid), and which are useful disinfectants and / or antiseptics that meet ostos standards. It is a further object of the present invention to provide a method for preparing polymers and / or copolymers derived from acrolein according to the aforementioned prior art for use as useful disinfectants and / or antiseptics. It is still an additional object of the present m 'enciór. to provide a method for preparing polymers and / or copolymers derived from acrolein according to the aforementioned prior art, for use in dermatological formulations, which include sunscreens. It is still a further object of the present invention to provide a method for preparing polymers and / or copolymers derived from acrolein according to the aforementioned prior art for use in other applications which includes as a preservative or as an animal feed additive. Through this specification, unless the context requires otherwise, the word "understand", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a whole number or group of integers but not the exclusion of any other whole number or group of integers. According to the present invention there is provided a method for the preparation of compositions of poly (2-propenal, 2-propenoic acid) comprising the steps of the methods of dissolving poly (2-propene, 2-propenoic acid) in a base aqueous, add an organic compound containing one or more hydrophobic groups, and the subsequent acidification of the solution, whereby the interaction between the hydrophobic groups of the organice compound / the poly (2-propenal, 2-propenoic acid) prevents precipitation of the poly (2-propenal, 2-propenoic acid) which occurs at pH = 5.5 and the solution is consequently stable over a wide range of pH. Preferably, the precipitation of? <"> li2-propenal, 2-propenoic acid) is prevented at pH > -3.5 The organic compound may be an anionic tensive.The anionic surfactant is preferably selected from sodium lauryl sulfate or decylbenzene sulfonate (sulfofoxy) disodium and disodium oxybis (decylsulfophenoxy) benzenesulfonate In one form of the invention, one or more phenols can be added to the solution of poly (2-propenal, 2-propenoic acid) before acidification.Phenol is preferably o-phenyl- In a further form of the invention, the composition containing poly (2-pro-enan, 2-propenoic acid) is first stored for a time in a basic composition before the addition of the surfactant and acidification. Further form of the invention, the composition exhibits increased antimicrobial activity, the method for preparing the composition comprises the preparation of poly (2-propenal, 2-propenoic acid) in the presence of air and / or oxygen, with or without inhibitor. Alternatively, the method comprises the subsequent preparation of the composition of poly (2-propenal, 2-propenoic acid) within a basic composition. Preferably, the organic compound is one or more of ethylenediamine tetra acetic acid, a lower alkanol, a phenol, isothiazolinones and glutaraldehyde, the composition exhibits a synergistic increase in antimicrobial activity. The composition may additionally comprise phenols and / or glutaraldehyde, whereby the odor of phenols and glutaraldehyde is reduced by the presence of poly (2-propenal, 2-propenoic acid). The composition may exhibit reduced transdermal migration of low molecular weight components of the composition as a result of the presence of poly (2-propenal, 2-propenoic acid). The low molecular weight composition may contain a sunscreen agent. The sunscreen agent can be one or both of octyl methoxycinnamate and octyl dimethyl p-aminobenzoate. In one form of the invention, the composition, especially for dermatological use, exhibits a sunscreen effect as a result of the presence of poly (2-propenal, 2-propenoic acid). In another form of the invention, the composition exhibits the formation of a continuous antimicrobial film on the substrates. In another form of the invention, the composition, especially for dermatological use, exhibits a free radical scavenging effect as a result of the presence of poly (2-propenal, 2-propenoic acid). According to the present invention, there is provided an aqueous polymer composition comprising poly (2-propenal, 2-propenoic acid) and an organo compound containing one or more hydrophobic groups, wherein the interaction between the hydrophobic groups of the organic compound and the poly (2-propenal, 2-propenoic acid) prevents the precipitation of poly (2-propenal, 2-propenoic acid, at pH> 5.5. "Preferably, poly (2-pro-enan, 2-propenoic acid) Preferably still, the organic compound is an anionic surfactant.The anionic surfactant may be chosen from sodium lauryl sulfate or disodium decylbenzene sulphonate (sulphoxy) and disodium oxybis \ decyl sulfonoxy benzene sulfonate. additionally one or more phenols.Phenol can be o-phenii-phenol In one form of the invention, the composition further comprises one or more of ethylene diamine tetra acetic acid, an aikanol .inferior, a phenol, isothiazolinones and glutaraldehia, the composition exhibits a synergistic increase in antimicrobial activity. The composition can be an emulsion. According to the present invention, the use of the compositions defined above for antimicrobial uses, for dermatological uses, or for use as a food additive is still further provided. It has now been discovered that the modification of the preparation of poly (2-propenal, 2-propenoic acid) as described in WO 88/04671 and WO 96/38186 (Examples Ib in each) by the concurrent bubbling in air and / or oxygen during polymerization, produces a polymer with a more discrete crystalline form that aids in recovery and subsequent drying, and which has slightly odorous oligomers and less contamination in the solid or liquid medium, and has an inherent velocity more high microbial activity; see Example 1 below. It has now been found that while the basic aqueous compositions containing the poly (2-propenal, 2-propenoic acid) are biostatic and / or biocides; however, the compositions are significantly unstable. Although, it has been shown additionally that you. pH decrease (decrease in concentration to the hydroxyl ion) of such compositions / solutions increases its chemical stability, it has been found counterproductively that the acidification of the composition at low pH, of about pH 6, causes the precipitation of poly (2-). propenal, 2-propenoic acid). It has now been shown that this precipitation can be avoided up to approximately pH 3.5 (ie more than ten times lower hydroxyl ion concentration), by a formulation method in which the poly (2-propene, 2-propenoic acid) is first dissolved in dilute aqueous base,} v-after the anionic surfactant is added, before acidification. Useful anionic surfactants are sodium lauryl sulfate ("SLS") or decylbenzenesulfone or (sulfofoxy) disodium and disulphite oxybis (decylsulfofenixi) belen sulphonate in equal weight ratios with poly (2-propenal, 2-propenoic acid). In order to be effective, it is important to maintain this order of addition, so that the poly (2-propene, 2-propene acid) co) is in its anionic form prior to the addition of the surfactant; see Example 2 below. This apparent interrelation between the two negatively charged species of poly (2-propenal, 2-propenoic), and the anionic detergent is surprising since repulsion would be expected between similar charges of the species. It has now been found that the basic aqueous solutions of poly (2-propenal, 2-propenoic acid) destroy microorganisms more rapidly than acidic solutions of the polymer. This discovery leads to the additional finding that the more stable acidic formulations containing poly (2-propenal, 2-propene-co-acid) and preferably, anionic surfactant, can subsequently become basic and, consequently, antimicrobially more active, immediately before. of its use, for example, a disinfectant and / or antiseptic and / or preservative; see Example 10 below. It has now been shown that if a solution of poly (2-propenal, 2-propenoic acid) which contains a phenol, with an anionic surfactant is acidified, a surprisingly stable emulsion is formed, and in this heterogeneous system, the poly (2) -propenal, 2-propenoic acid) in the hydrophobic phase is protected from chemical degradation by hydroxyl ions in the hydrophilic phase; see Example 2 below. The o-phenyl-phenol is particularly useful, and in equal weight ratio with the poly (2-propenal, 2-propenoic acid). It has now been shown that the inclusion of phenols in addition to the anionic surfactants in the compositions containing poly (2-pro-enan, 2-propenoic acid) allows the further acidification of these compositions before any precipitation of the poly (2-propene, 2-propenoic acid) that is, additional chemical stability is achieved with respect to the hydroxyl and / or base ion; see Example 2 below. Additionally, it has now been shown that if the composition containing poly (2-? Ropenal, 2-propenoic acid) is only maintained first, for example for about 11 days at about pH 9, in an aqueous alkaline medium, before the addition of the anionic surfactant and then the precipitation of the phenol will not occur, on acidification; see Example 2 below. It has now been shown that the co-formulation of the composition containing poly (2-propenal, 2-propenoic acid), with anionic surfactant, and optionally with additionally a phenol, produces a composition which provides a continuous antimicrobial film on substrates, after application to it, for example skin, floor, walls, furniture, etc. Without these additives, the film is invariably discontinuous and consequently only partially protects the substrate, antimicrobially. It has now been shown that these films retain moisture, facilitating their protective antimicrobial activities. If they also contain a volatile component that carries out their pH-dependent antimicrobial activities, then, in turn, these activities can be increased while evaporation takes place.; see Example 10, below, has now shown that the inclusion of or an anionic surfactant in the formulations containing poly (2-propenal, 2-propenoic acid), increases its chemical stability to the hydroxyl ion and / or base; see Example 3 below. It has now been shown that poly (2-propenal, 2-propenoic acid) absorbs in the UV, and that a peak of about 268 nm, as replaced by absorption on about 232 nm, correlates with and is a convenient monitor of the Chemical stability of poly (2-pro? enal, 2-propenoic acid) in basic aqueous solutions; see "Stability Test" below. It has now been shown that the co-formulating anionic surfactant and / or ethylenediaminetetraacetic acid ("EDTA") and / or its salts and / or a lower alkanol improves the antimicrobial properties of the compositions containing the poly (2-propene, -propenoic), see Examples 4 and 5 below.

It has now been further shown that not only is the antimicrobial activity increased, but surprisingly, it is increased synergistically by the incorporation into the composition containing the poly (2-propene, 2-propenoic acid), of EDTA (and / or its salts) and / or phenols, and / or isothiazolinones, and / or glutaraldehyde; see Example 7 below. It has now been shown that the inclusion of poly (2-propenal, 2-propenoic acid) decreases the noticeable odors of the compositions containing phenol or phenols and / or antimicrobial glutaraldehyde; see Example 6 below. It has now been shown that the surprising apparent interaction between the negatively charged phenols and the negatively charged anionic form of the poly (2-propenal, 2-propenoic acid) is more -general, and is thought to result from the interaction of the hydrophobic portions of the respective species. Thus, it is shown that the presence of poly (2-propenal, 2-propenoic acid) in an emulsion with the UV solar filter octylmethoxycinnamate, or octyl dimetii p-aminobenzoate, prevents the migration of any of the solar filters through a membrane which is a model for the skin; see Example 8 below. Accordingly, it is apparent that the poly (2-propenal, 2-propenoic acid) can be used as a cs-foroulant to reduce the potential toxicity and / or allergy and / or antigenicity and / or irritation and / or inflammation of filter agents solar, or other compounds, for example phenols, which results from the transdermal migration of such constituents, in dermatological preparations, into the bloodstream. It has further been shown that the peak at 268 nm and below provides significant UVC absorption. UVC energy is more than 50% of the energy of sunlight (Lide, DF, "CRC Handbook of Chemistry and Physics", CRC Press, 73rd edition, 1992-93, page 14-8) and is on the length of wave to which the skin is most sensitive ("Harry's Cosmeticology", _ JB Wilkinson and RJ Moore Eds., Chemical Publishing CO. Inc., New York, 1982, page 128) and which induces changes that "alter the structure of the ADM (Kano RJ and Colome JS "Microbiology", West Pubiishing Company 1986, pages 162) .Therefore, it has been found now that it is an advantage to include poly (2-propenal, 2-propenoic acid) in dermatological sunscreen preparations. It has now been shown that compositions containing poly (2-propenal, 2-propenoic acid) and containing only polymeric ingredients, (for example polymeric solvents / emollients and / or polymeric surfactants and / or emulsifiers) and / or volatile ingredients provide compositions for dermatological applications, libr it is of any component that, after spreading on the skin, could migrate transdermally and within the bloodstream to cause toxicity, allergy, etc .; see Example 8 below. It has now been shown that the formulation of lime compositions (for example free of conventional surfactants) is facilitated by the surfactant properties of poly (2-propenal, 2-propenoic acid). It has now been shown that poly (2-propenal, 2-propenoic acid) has the ability to absorb free radicals and this is a unique use in dermatological compositions with the perspective of decreasing the damage to the skin effected by free radicals; see Example 9 below. It has now been shown that the methods, compositions and uses provided herein apply to all compounds described in WO 88/04671 and WO 96/38186, particularly those compounds which are hydrophilic and / or soluble in an aqueous medium; the methods shown herein to keep these compounds in solution and / or emulsion in an aqueous medium generally facilitate any desired chemical reactions with these compounds in an acidic medium. The invention will now be described with reference to. a number of specific Examples, each of which should not be construed as limiting the scope of the invention. In the following examples, reference is made to a number of tests as follows: 1. Biocidal Test Dilute the sample with sterile water to obtain the required concentration. Load 19.9g of the diluted sample into a sterile jar and inoculate with 0.1 mL of IO'-IO "1 suspension of Ps aeruginosa and mix, transfer immediately to 1 mL of the inoculated sample to 9 mL of vortex and broth. Letheen culture: Give dilutions in series of 1 in 10. Pour with tripton soy agar Incubate for 3 days at 37 ° C. 2. Minimum Destruction Concentration Test Make dilutions in 1 in 2 series of the sample using sterile saline. to 0.85% add 0.1 rnL of suspension of the test organism to the dilution incubate at 37 ° C for 24 hours Subculture one mL of each tube into 10 mL of sterile nutrient broth in addition to TWEEN 80; incubate at 37 ° C for 24 hours. 3. Sporicidal Test Add 1 mL of E spore suspension. Subtil us var niger (efu 107 / mL) to 10 mL of sample solution in a sterile bottle and mix in a vortex. Immediately remove 0.020 mL and add to the recovery broth; repeat 5 times. Mix in a vortex and incubate at 37 ° C for 14 days. Confirm by "heat shock" all tests. . Sporicidal Efficiency Test _ Inoculate sterile glass slides Gene a suspension of B. subtilus var niger (cfu 10 '/ mL). Dry under vacuum for 24 hours at 30 ° C. Add 4 mL of sample solution to the slide. After 10 minutes of the contact time, blot the slides at 30 ° C for 72 hours. Sonicate and mix the slides in the deactivation broth in a vortex. Enumerate by making 4 dilutions in series of 1 in 10 on agar and incubate for 48 hours at 30 ° C. 5. Modified Kelsey Sykes Test Add 1 mL of test organism culture (2 x '' - 2 x 10y) cfu / mL containing 1. yeast to 3 ml, of the test solution. At 8 minutes, subculture 0.02 mL into each of the 5 tubes containing recovery ca, and mix in a vortex. Incubate at 37 ° C for 48 hours. 6. Stability test Poly (2-propenal, 2-propenoic acid) (Ig) was dissolved in 0.5? ~ W / w aqueous sodium carbonate, and left at room temperature. The stability was measured by the UV method. The stability of the aqueous solutions of the polymers was followed by the disappearance of a UV peak close to 268 nm and the appearance of a peak close to 232 nm; AC. Absorbance at 268 nm, of 0.02% solution = 1.5.

Example 1 (a) With hydroquinone; open to air Water, (720 mL at room temperature, approximately 20 ° C) and acrolein (60 g, recently distilled and hydroquinone added at 0.25% w / w) were placed in an open beaker inside a fume hood , and it was stirred very vigorously, mechanically. Then, 0.2 M aqueous sodium hydroxide (21.4 mL) was added to bring the pH to 10.5 - 11.0. The solution immedly turned yellow, typical of the hydroquinone anion and, within a minute, the color had disappeared and the solution became milky. Approximately 1 minute later, the precipitation of a white crystalline woolly polymer began and appeared to be completed within 15-30 minutes. The precipitated polymer, poly (2-pro? Enai, 2-propenoic acid), was filtered and washed with water (250 mL; dried at room temperature on filter papers for 2 days (yield 25.2 g), then sprayed As a thin layer in glass petri dishes and heated to 40 ° C / 8 o'clock, this heating was continued in the following chronograms: 50 ° C / 15 hours (after it was ground), 65 ° C / 4 hours, 70 ° C / 2 hours, 75 ° C / 18 hours, 82 ° C / 24 hours It is contemplated that this method can be scaled to include, for example the step-by-step addition of acrolein, followed by faster drying. The resulting poly (2-propenal, 2-propenoic acid) is prepared by adding 2 g, with stirring for 15-30 minutes, to an aqueous solution of sodium carbonate 1% w / w (100 mL) and diluted as required. (b) With hydroquinone, closed vessel As in the above for (a) except that the reaction vessel was a 1 liter flask with stopper, this resulted in a slow formation of precipitate which was poorly crystalline and glassy - yield 25.5 g. (c) Without hydroquinone; closed vessel As in the above for (a) except that hydroquinone was excluded, and the reaction vessel was a 1 liter stoppered flask; this resulted in a crystalline product - yield 21.0 g. (d) Without hydroquinone; open to air As in the above for (a) except that hydroquinone was excluded; this resulted in a crystalline product-yield 26.0 g. After 3 days at room temperature, the diluted samples (0.25% w / w). being the product of examples l (a) to 1 (b), they were tested by the Biocidal Test. The results are shown in Table 1: Table 1 Cfu / mL (ie Units / mL forming colony; Example 2 A series of tests were conducted to examine the impact of the surfactant and / or water, and / or regulator, and / or phenol on the state of precipitation and the pH. The results are shown in Table 2: Table 2 A - 4% w / w of polymer in 4% w / w sodium bicarbonate, freshly prepared.

B - as A, aged for 11 days at room temperature. C - aqueous sodium lauryl sulfate 4% w / w. D - Dowfax 3B2 aqueous 4% w / w. - Decyl (sulfophenoxy) benzenesulfonic acid, disodium salt.

- Oxibis (decylbenzenesulfonic acid), disodium salt. E - Dowfax 3B2 - Dowfax 3B2 aqueous 4% w / w. - Decyl (sulfophenoxy) benzenesulfonic acid, disodium salt - Oxybis (decylbenzenesulfonic acid), disodium salt F - Dowicide A - orthophenylphenol, sodium salt G - Dowicide (orthophenylphenol), 33s w / w. in sodium hydroxide solution, 66% w / w H - 4 - ter - amylphenol, 33% w / w, in sodium hydroxide solution, 66% w / w I - acetic acid 10% w / w: sodium hydroxide buffer, pH 4.5 . Example 3 (a) A 2% w / w solution of poly (2-propenal, 2-propenoic acid) in 2% w / w aqueous sodium carbonate containing 2% w / w sodium lauryl sulfate a environment pri (~ 9.8) was shown by the UV test to be more stable than a solution without sodium iauril sulfate for 11 days / 38 ° C. (b) A 4% w / w solution of poly (2-propenal, 2-propenoic acid) in aqueous 4% w / w sodium carbonate containing 2%. p / p of sodium lauryl sulfate ac? or with hydrochloric acid at pH 5, was more stable in the UV test than a solution without sodium lauryl sulfate for 4 days / room temperature. The results are shown in Table 3: Table 3 Example 4 A series of tests was conducted to examine the impact of the incorporation of EDTA or SLS on the antimicrobial activity of a 2% w / w solution of poly (2-propenal, 2-propenoic acid). The results of the Eiocida Test are shown in Table 4: Table 4 Cfu / mL Example 5 A test formulation of. 1.5 w / w solution of poly (2-propenal, 2-propenoic acid) in 6b _ w / w of ethanol in water was compared with a control formulation of 65-w / w of ethanol in water. First, in in vivo tests on human hands as a skin antiseptic, the results are shown in Table 5A; second, the test formulation was assessed by the Modified Kelsey Sykes Test, the results are shown in Table 5B: Formulation (a) 1.5% w / w of polymer in 65% w / w ethanol (Test) (b) 65 % p / p of ethanol in water (Control) Table 5A t = 0 (before application) t = 2.4 (2 hours and 4 hours, respectively, after 1¿ application and the hands being peeled) Table 5B Example 6 A series of tests were conducted to examine the impact of poly (2-propenal, 2-propenoic acid) on the odors of compositions containing phenols and / or glutaraldehyde. The results are shown in Table or: Solution A - 1 g of poly (2-propenal, 2-propenoic acid) was dissolved in 50 mL of sodium carbonate at 1% W / W. Solution B - 1 g of 4-tert-amylphenol and 2 g of sodium hydroxide were dissolved in 40 mL of water. Solution C - 25% w / w glutaraldehyde in water. Table 6 Example 7- A series of tests were conducted to examine any synergies between the antimicrobial activity of the solutions containing poly (2-propenal, 2-propenoic acid) and EDTA and / or phenols, and / or isothiazolinones, and / or glutaraldehyde. If the Minimum Destruction Concentrations of compounds A, B, and a mixture of A and B are a, o and m, respectively, then there is synergy ("S") when mixing A and B if a / m + b / m > 1 ie S = (a + b) / m > 1 for synergy The following solutions were tested by the Minimum Destruction Concentration Test, and gave the results shown in Table 7: Table 7 Phenol = DOWICIDE A; thiazolinone = KATHON Example 8- The effect of the presence of poly-2-propenal, 2-propenoic acid) on the migration of various agents through a model for the skin were studied as follows.

The results are shown in Table 8: (a) poly (2-propene, 2-propenoic acid) (0.5g) was dissolved in polyethylene glycol 1000 (10g) by stirring at 70 ° C, then sodium hydroxide was added in micro pellets (50mg) and stirred for 2 minutes, and then octylmethoxycinnamate (10g, sunscreen agent) was added, followed by a mixture of the polymeric emulsifiers PEMULIN TR1 and CARBOPOL 2984 (0.5g, equal parts) while maintaining the temperature at 70 ° C / 15 minutes. This resulting composition was then emptied with stirring in water (79g, at room temperature) and the pH was adjusted to 7. (b) The same as (a) above, except that the octylmethoxycinnamate was replaced by octyldimethyl p-aminobenzoate. (c) The same as (a) above, except that the 1: 1 mixture of polymeric emulsifiers was replaced by a 1: 1 mixture of TWEEN 80 and stearic acid. (d) The same as (a) above, except that the 1: 1 mixture of polymeric emulsifiers was replaced by a mixture 1: 1 of TWEEN 80 and stearic acid followed by CARBOPOL 2984 (0.25g). (e) The same as (a) above, except that the poly (2-propenal, 2-propenoic acid) was omitted. (f) The same as (c) above, except that the poly (2-propenal, 2-propenoic acid) was omitted. In a special apparatus, the samples were applied to one side of a 0.45 micron cellulose acetate membrane in contact, on the other hand, with a stirred solution of ethanol. "After" 1.5 hours, the "ethanol" spectrum was compared with the "Before" sample solution in the same solvent; Table 8"if" = exhibits maximum; "no" = does not show it Example 9 The ability of the poly (2-propene, 2-propenoic acid) to absorb free radicals is indicated by each of the following: First, it was treated with a 1% w / w solution of poly (2-propene, -propenoic acid) in aqueous sodium carbonate, adjusted to pH 7.1, with two successive additions of Fenton reagent comprising 0.1% w / w of ferrous sulfate (3 mL) and 30% v / v of hydrogen peroxide (3 mL) , and stirred; Oxygen bubbles were observed and the typical golden color of the solution of poly (2-propenal, 2-propenoic acid) disappeared. Second, the following was mixed as shown in Table 9: Table 9 Si = included in the sample No = NOT included in the sample Inhibition by the poly (2-propenal, 2-propenoic acid) of the free radical cobalt-catalyzed auto-oxidation of flaxseed oil demonstrated by the speed of each of the samples that become "sticky" after stretching as film on glass, especially, shows 2 > Sample 1.

Example 10 In Tables 10A, 10B, and 10C, the results obtained for the following derivative compositions are shown: (a) poly (2) was dissolved (2). -propeneal, 2-propenoic acid) (18g) e water (529g) containing hydrogenated sodium carbonate (18g), and then a mixture of tetrasodium EDTA (18g), sodium lauryl sulfate (18g), and stirring continued for 30 minutes, after which the pH was adjusted from 8.5 to 9 by the addition of sodium hydroxide. and micro-pellets (approximately 2g). (b) Part A: poly (2-propene, 2-propenoic acid was dissolved (2.7g) by stirring in water (63g) containing sodium carbonate (0.9g), DOWFAX 3B2 (2.7g) and l continuous stirring were added for 15 minutes; the pH is adjusted from 9.4 to 5.1 by the addition of 10% w / w hydrochloric acid (2.5 g). Part B: Water (27g) containing sodium carbonate (1.35g) and tetrasodium EDTA (2.7g) Part B was added to Part A, immediately before the microbiological test. (c) poly (2-propenal, 2-propenoic acid) (2g) was dissolved by stirring for 20 minutes in water (98g) containing DOWICIDE A (2g); DOWFAX 3B2 (8g) was added and stirring was continued for 60 minutes to give a clear solution of pH 10.5 which was then adjusted by the addition of 10% w / w hydrochloric acid (1.2g) to a stable emulsion of pH 5.0 . The antimicrobial results were obtained after aging at 38 ° C / 14 days. Table 10A Modified Kelsey Sykes Test: Table 10B Sporicidal test Table 10C Sporicidal efficiency test Cfu / slide Modifications and values such as would be apparent to the recipient expert are considered to fall within the scope of the present invention.

Claims (28)

1. CLAIMS 1. A method for the preparation of compositions of poly (2-propene, 2-propenoic acid) characterized in that it comprises the steps of the method of dissolving poly (2-propene, 2-propenoic acid) in aqueous base, adding a compound organic containing one or more hydrophobic groups, and subsequently acidifying the solution, whereby the interaction between the hydrophobic groups of the organic compound and the poly (2-propenal, 2-propenoic acid) prevents the precipitation of poly (2-propenal, 2-propenoic acid) that occurs at pH = 5.5 and the solution is consequently stable over a wide range of pH.
2. 2. The method according to claim 1, characterized in that the precipitation of the poly (2-propenal, 2-propenoic acid) is prevented at pH 3.5.
3. 3. The method according to claim 1 or 2 characterized in that the organic compound is an anionic surfactant.
4. 4. The method according to any of claims 1 to 3 characterized in that one or more phenols are added to the solution of poly (2-propenal, 2-propenoic acid) before acidification. 5. The method according to any of claims 1 to 4, characterized in that the composition containing poly (2-propenal, 2-propenoic acid) is first stored for a time in the basic composition before the addition of the surfactant. and acidification. The method according to any of the preceding claims, characterized in that the anionic surfactant is selected from sodium lauryl sulfate or disodium decyl (sulfofoxy) benzenesulfonate and disodium oxybis (decyl sulphoxyphenoxy) benzenesulfonate. 7. The method according to claims 4 to 6, characterized in that the phenol is o-phenyl-phenol. The method according to claim 1, characterized in that the composition exhibits increased antimicrobial activity, the method comprises the preparation of poly (2-propenal, 2-propenoic acid) in the presence of air and / or oxygen with or without inhibitor . 9. The method according to claim 1, characterized in that the composition exhibits increased antimicrobial activity, the method comprises the subsequent elaboration of the composition of poly (2-propenal, 2-propenoic acid) in a basic composition. 10. The method according to claim 1, characterized in that the organic compound is one or more of ethylenediamine tetraacetic acid, a lower alkanol, a phenol, isothiazolinones and glutaraldehyde, the composition exhibits a synergistic increase in activity antimicrobial . 11. The method according to the claim 1, further characterized in that the composition comprises phenols and / or glutaraldehyde, whereby the odor of phenols and / or glutaraldehyde is reduced by the presence of poly (2-propenal, 2-propenoic acid). The method according to claim 1, characterized in that the composition exhibits reduced transdermal migration of low molecular weight components of the composition as a result of the presence of poly (2-propenal, 2-propenoic acid). 13. The method according to claim 12, characterized in that the low molecular weight composition contains a sunscreen agent. 14. The method according to the claim 12, characterized in that the sunscreen agent is one or both of octyl methoxycinnamate and octyldimethyl p-aminobenzoate. The method according to claim 1, characterized in that the composition, especially for dermatological use, exhibits an effect that filters the sol as a result of the presence of poly (2-propenal, 2-propenoic acid). 16. The method according to any of claims 1 to 15, characterized in that the composition exhibits the formation of a continuous antimicrobial film on the substrates 17. The method according to claim 1, characterized in that the composition, especially for dermatological use exhibits a free radical scavenging effect as a result of the presence of poly (2-propenal, 2-propenoic acid). 18. An aqueous polymeric composition characterized in that it comprises poly (2-propenal, 2-propenoic acid) and an organic compound containing one or more hydrophobic groups, wherein the interaction between the hydrophobic groups of the organic compound and the poly (2-propene) , 2-propenoic acid) prevents the precipitation of poly (2-propenal, 2-propenoic acid) at pH = 5.5. 19. The composition according to claim 17, characterized in that the poly (2-propenal, 2-propenoic acid) does not precipitate at a pH = 3.
5. 5. The composition according to claim 18 or 19, characterized in that the organic compound is an anionic surfactant. The composition according to claim 20, characterized in that the anionic surfactant is chosen from sodium lauryl sulfate or disodium decyl (sulfofoxy) benzenesulfonate and disodium oxybis (decyl sulphoxyphenoxy) benzenesulfonate. 22. The composition according to any of claims 18 to 21, further characterized in that it comprises one or more phenols. 23. The composition according to claim 22, characterized in that the phenol is o-phenyl-phenol. 24. The composition according to any of claims 18 to 23, characterized in that the composition further comprises one or more of ethylenediamine tetraacetic acid, a lower alkanol, a phenol, isothiazolinones and glutaraldehyde, the composition exhibits a synergistic increase in the antimicrobial activity. 25. The composition according to any of claims 18 to 24, characterized in that the composition is an emulsion. 26. The use of compositions according to any of claims 18 to 25, for antimicrobial uses. 27. The use of compositions according to any of claims 18 to 25, for dermatological uses. 28. The use of compositions according to any of claims 18 to 25 as an animal feed additive.