WO2024241212A1

WO2024241212A1 - Disinfectant composition

Info

Publication number: WO2024241212A1
Application number: PCT/IB2024/054924
Authority: WO
Inventors: Daniela DONELLI; Alessandra CAPEZZONE DE JOANNON; Elena MASTROCOLA
Original assignee: Angelini Pharma SpA
Current assignee: Angelini Pharma SpA
Priority date: 2023-05-22
Filing date: 2024-05-21
Publication date: 2024-11-28
Anticipated expiration: 2025-11-22
Also published as: IT202300010335A1

Abstract

The present invention concerns a disinfectant composition, in particular for the disinfection of the skin, comprising hydrogen peroxide, phenoxyethanol and a mixture of surfactants derived from coconut oil fatty acids.

Description

TITLE

DISINFECTANT COMPOSITION

FIELD OF THE INVENTION

The present invention concerns a disinfectant composition, in particular for the disinfection of the skin, comprising hydrogen peroxide, phenoxyethanol and a mixture of surfactants derived from coconut oil fatty acids. The composition of the present invention has demonstrated advantages in terms of bactericidal, virucidal and fungicidal efficacy, as well as an improved storage stability.

STATE OF THE ART

The skin often comes into contact with potentially harmful pathogens, which can root and develop thereon. A potentially harmful pathogen is an organism that can cause diseases. Non-limiting examples of potentially harmful pathogens are bacteria, viruses, fungi, allergens, molds and yeasts.

The regular disinfection of an area of human skin, for example the skin of hands and feet, is a common practice to reduce the risk of infection for human beings.

The disinfection of the skin is useful for human health, as it helps to prevent the spread of diseases and reduce the probabilities that a human being contracts a disease by coming into contact with potentially harmful pathogens.

Hand hygiene by means of disinfectant compositions has become a procedure recommended by WHO to improve user responsiveness and meet the recommendations of a good hygiene practice. Generally, hydroalcoholic solutions with bactericidal, virucidal and fungicidal properties are used, with no cleansing effect.

Most commercially available disinfectants contain chemical active ingredients and synthetic agents such as halogenated compounds, plasticizers and alcohols. The above-mentioned antimicrobial agents, while being effective, are of a toxic nature. The disposal of such compositions is dangerous because they contaminate the environment and in particular water bodies.

The disinfectant compositions destined to the use on the skin mainly comprise an alcohol base. Many disinfectant compositions commonly available show the drawback of flammability and high volatility. Furthermore, alcohols such as isopropyl alcohol and ethanol, commonly used in such compositions, are aggressive to the skin. Alcohols generally cause an excessive dryness of the skin and have also been reported as a cause of eczema and rashes.

As the use of disinfectant compositions is becoming more widespread, it remains of interest to identify new compositions that allow an effective disinfection according to current standards, while avoiding the use of an alcohol base, and showing a better stability over time.

The oxygenated water (hydrogen peroxide) is a common disinfectant that is used to clean and disinfect skin and surfaces. However, hydrogen peroxide can be irritating to the skin and can cause allergic reactions in some people.

For this reason, many skin disinfectant formulations that use hydrogen peroxide as an active ingredient have been developed to improve their safety and effectiveness. Currently, most of the skin disinfectant compositions comprising hydrogen peroxide contain other active ingredients, such as alcohols, glycols, benzalkonium chloride, benzethonium chloride, cetylpyridinium chloride, or other compounds that can increase the efficacy and safety of the disinfectant. Some formulations also include soothing ingredients to help reduce skin irritation and improve the tolerance of the disinfectant. Compositions of this type are described, for example in EP618768B1 , EP3911158A1 , W02001/065939A1 , W02005/089100A2 and W02009/021336A1 . The phenoxyethanol is a preservative and a disinfectant agent commonly used in cosmetic products and skin disinfectants. In particular, it is known for its activity against bacteria, fungi and viruses. However, phenoxyethanol can be irritating to some people, especially when used in high concentrations. Compositions of this type are described, for example, in WO2022/037821A1 , W02008/071027A1 , and W02007/071090A1.

SUMMARY OF THE INVENTION

The Applicant has addressed the problem of providing a new disinfectant composition, in particular for the disinfection of the skin, that overcomes the previously mentioned issues.

In particular, the Applicant aimed to find a water-based disinfectant composition that is less aggressive to the skin with respect to alcohol-based compositions.

The Applicant also aimed to obtain a disinfectant composition that met the current standards of efficacy against bacterial, viral and fungal agents. Finally, the Applicant aimed to obtain a disinfectant composition stable over time and with a low environmental impact.

After extensive experimentation, the Applicant has surprisingly observed that a water-based disinfectant composition comprising determined quantities of hydrogen peroxide, phenoxyethanol and of a mixture of surfactants derived from coconut oil fatty acids allowed to achieve all the intended objectives.

In particular, the disinfectant composition formulated by the Applicant allowed to obtain a valid efficacy against the main bacterial, viral and fungal pathogens and passed the stability tests at three months, with a low environmental impact and without the use of components aggressive to the skin.

Therefore, a first object of the present invention concerns a water-based disinfectant composition comprising (i) hydrogen peroxide, (ii) phenoxyethanol, (iii) at least one nonionic surfactant derived from coconut oil fatty acids, and (iv) at least one amphoteric surfactant derived from coconut oil fatty acids, wherein

• the amount of said hydrogen peroxide is more than 2% by weight relative to the weight of said composition,

• the amount of said phenoxyethanol is more than 1 % by weight relative to the weight of said composition, and

• the total amount of said at least one nonionic surfactant derived from coconut oil fatty acids and said at least one amphoteric surfactant derived from coconut oil fatty acids is equal to or greater than 2.75%, preferably equal to or greater than 3%, by weight relative to the weight of said composition.

DETAILED DESCRIPTION OF THE INVENTION

The present invention can show one or more of the preferred features hereafter indicated. They can be combined at will between them according to the application needs.

The disinfectant composition according to the present invention comprises hydrogen peroxide in an amount more than 2 percent by weight relative to the weight of the composition. Preferably, the percentage of hydrogen peroxide is equal to or less than 3% by weight relative to the weight of the composition. Advantageously, the percentage of hydrogen peroxide is between a value greater than 2% and a value equal to or less than 3% by weight relative to the weight of the composition. Advantageously, the percentage of hydrogen peroxide is between 2.05% and 2.95% by weight relative to the weight of the composition. In particular, the composition according to the present invention comprises a percentage of hydrogen peroxide equal to 2.10%, 2.15%, 2.20%, 2.25%, 2.30%, 2.35%, 2.40%, 2.45%, 2.50%, 2.55%, 2.60%, 2.65%, 2.70%, 2.75%, 2.80%, 2.85%, or 2.90% by weight relative to the weight of the composition.

The disinfectant composition according to the present invention comprises phenoxyethanol in an amount more than 1 % by weight relative to the weight of the composition. Preferably, the percentage of phenoxyethanol is equal to or less than 2% by weight relative to the weight of the composition. Advantageously, the percentage of phenoxyethanol is between a value greater than 1 % and a value equal to or less than 2% by weight relative to the weight of the composition. Advantageously, the percentage of phenoxyethanol is between 1.05% and 1.95% by weight relative to the weight of the composition. In particular, the composition according to the present invention comprises a percentage of phenoxyethanol equal to 1.10%, 1.15%, 1.20%, 1.25%, 1.30%, 1.35%, 1.40%, 1.45%, 1.50%, 1.55%, 1.60%, 1.65%, 1.70%, 1.75%, 1.80%, 1.85%, or 1.90% by weight relative to the weight of the composition.

The disinfectant composition according to the present invention comprises at least one nonionic surfactant derived from coconut oil fatty acids and at least one amphoteric surfactant derived from coconut oil fatty acids in a total amount equal to or greater than 2.75%, preferably equal to or greater than 3%, by weight relative to the weight of the composition. Advantageously, the disinfectant composition according to the present invention comprises at least one nonionic surfactant derived from coconut oil fatty acids and at least one amphoteric surfactant derived from coconut oil fatty acids in a total amount between 3% and 20%, preferably between 3.5% and 15%, more preferably between 4% and 10% by weight relative to the weight of the composition.

The coconut oil fatty acids are a mixture of fatty acids having 8 to 18 carbon atoms, with a predominance of saturated fatty acids, approximately between 80% and 90% and a smaller amount of mono- and poly-unsaturated fatty acids, between 10% and 20%.

Advantageously, the disinfectant composition according to the present invention comprises at least one nonionic surfactant derived from coconut oil fatty acids chosen in the group consisting of coco monoethanolamide (MEA cocam ide), coco diethanolamide (DEA cocamide), coco monoisopropanolamide (MIPA cocamide), methyl MEA cocamide, glyceryl cocoate, PEG-4 glyceryl cocoate, PEG-7 glyceryl cocoate, PEG-18 glyceryl cocoate, PEG-30 glyceryl cocoate, PEG-80 glyceryl cocoate, glyceryl ether cocoate, glyceryl ether-2 cocoate, glycerether-7 cocoate, glycerether-17 cocoate, PEG-9 cocoglyceride, cocoglucoside.

Preferably, the disinfectant composition according to the present invention comprises at least one nonionic surfactant derived from coconut oil fatty acids in an amount between 2% and 15%, preferably between 2.5% and 12%, more preferably between 3% and 10% by weight relative to the weight of the composition.

The nonionic surfactants derived from coconut oil fatty acids are commercial products realized and distributed, for example, by the company BASF under the brand name Plantacare (Plantacare 818 cocoglucoside) and Comperlan (Comperlan COD Cocamide DEA), and Zschimmer & Schwarz under the brand name Oxypon (for example PEG-9 Cocoglycerides Oxypon 401 ).

Advantageously, the disinfectant composition according to the present invention comprises at least one amphoteric surfactant derived from coconut oil fatty acids chosen in the group consisting of sodium cocoamphoacetate, disodium cocoamphodiacetate, coco betaine, cocoamidopropyl betaine, cocodimethylcarboxymethyl betaine, cocodimethylsulfopropyl betaine disodium cocoamphopropionate, cocam idopropyl hydroxysultaine, cocoamphocarboxyglycinate, sodium cocoamphohydroxypropylsulfonate, cocamine oxide, dihydroxyethylcocamine oxide, cocam idopropylamine oxide.

Preferably, the disinfectant composition according to the present invention comprises at least one amphoteric surfactant derived from coconut oil fatty acids chosen in the group consisting of disodium cocoamphodiacetate, cocoamidopropyl betaine.

Preferably, the disinfectant composition according to the present invention comprises at least one amphoteric surfactant derived from coconut oil fatty acids in an amount between 0.10% and 0.50%, preferably between 0.15% and 0.30%, more preferably between 0.20% and 0.25% by weight relative to the weight of the composition. The amphoteric surfactants derived from coconut oil fatty acids are commercial products realized and distributed, for example, by the company BASF under the brand name Dehyton (Dehyton DC Disodium Cocoamphodiacetate), Clariant under the brand name Genagen (Genagen CAB 818 Cocam idopropyl Betaine) and Genaminox (Genaminox CLS Cocamine Oxide), Stepan under the brand name Amphosol (Amphosol CG cocam idopropyl betaine) and Ammonyx (Ammonyx CDO cocam idopropylamine oxide), Lonza under the brand name Amphoterge (Amphoterge K-2 disodium cocamphopropionate), and Solvay Novecare under the brand name Mirataine (Mirataine CBS Cocamidopropyl hydroxysultaine).

The water-based disinfectant composition according to the present invention comprises the above-mentioned ingredients dissolved in water, preferably distilled or demineralized water, representing the main component of the composition, in an amount generally equal to or greater than 50%, preferably equal to or greater than 60%, more preferably equal to or greater than 70% by weight relative to the weight of the composition.

The water-based disinfectant composition according to the present invention can comprise additional ingredients known in the art such as for example cationic, anionic, nonionic and amphoteric surfactants, viscosifiers, preservatives, solubilizers, chelators, pH correctors, dyes, and fragrances.

Examples of suitable surfactants include sorbitans, long-chain ethoxylated alcohols, alkyl polyglycosides, soaps, alkyl sulfates, such as, for example, sodium cetylstearyl sulfate, sodium lauryl sulfate, sodium lauretere sulfate, sodium stearate, monoalkyl and dialkyl phosphates, alkyl sulfonates, hydrogenated castor oil, acyl isothionates, sucrose esters, betaines, lecithins, quaternary ammonium salts, alkyloleates, glycerides, as, for example, caprylocaproyl polyoxylglycerides (caprylocaproyl macrogolglycerides) and emulsifiers from olive oil.

Suitable viscosizing additives comprise inorganic compounds such as sodium sulfate and organic compounds such as sorbitol, mannitol, fructose, alginate, starch, and mixtures thereof.

Examples of suitable preservative additives useful in the present invention include, for example, alcohols, such as ethanol and benzyl alcohol, methyl and propyl parahydroxybenzoate, butylated hydroxyanisole (BHA), sorbates, urea derivatives, and isothiazolinones, natural preservatives, such as for example ascorbic acid and derivatives, tocopherol and derivatives, polyphenols, and mixtures thereof.

Suitable solubilizing additives comprise, for example, alcohols, ketones (such as acetone and methyl isobutyl ketone), glycols (such as ethylene glycol, propylene glycol and butylene glycol), polyethylene glycols (such as PEG-40, PEG-50, PEG- 60), alkyl acetates (such as amyl acetate, isopropyl acetate, butyl acetate), glycerin and mixtures thereof.

Examples of sequestering or chelating additives useful in the present invention are GLDA (tetrasodium glutamate diacetate), EDTA (ethylenediaminetetraacetic acid), HEDTA (hydroxyethylenediaminetriacetic acid), ethyldronic acid, alkyl oxalates, lithium or potassium oxalate, sodium or potassium pyrophosphate.

Examples of pH correctors useful in the present invention comprise citric acid, lactic acid, tartaric acid, phosphoric acid, sodium hydroxide and potassium hydroxide.

Examples of useful fragrances in the present invention are, for example, natural essential oils or fractions or concentrates of essential oils, such as for example lemon oil, bergamot oil, lavender oil, limonene, linalool. Preferably the composition of the present invention comprises a total amount of fragrances between about 0.1 % and about 1 .0%.

Examples of dyes preferably used in the present invention are easily washable water-soluble dyes that do not stain the skin and leave no residue such as, for example, Acid Blue 3 C.1.42051 , Acid Blue 9 C.I.42090, Acid Blue 74 C.1.73015, Pigment Blue 15 C.1.74160, Acid Yellow 3 C. I.47005, Food Yellow 3 C.1.15985, Acid Yellow 23 C.1.19140, Acid Yellow 73 C.I.45350, Acid Red 14 C.1.14720, Acid Red 18 C.1.16255, Acid Red 27 C.1.16185, Acid Red 51 C.I.45430, Acid Green 1 C.1.10020, Acid Green 25 C.1.61570, and mixtures thereof.

The water-based disinfectant composition according to the present invention is preferably free of components that can be classified as microplastics, such as for example acrylic and methacrylic polymers and copolymers classified by the International Nomenclature of Cosmetic Ingredients (INCI) with the term polyquaternium followed by a number, as for example polyquaternium-7 (copolymer of acrylamide and diallyldimethylammonium chloride) and silicone polymers classified by the International Nomenclature of Cosmetic Ingredients (INCI) with the term silicone quaternium followed by a number, as for example silicone quaternium 22 .

The following examples are now provided for illustrative and non-limiting purposes. EXPERIMENTAL PART

Example 1 :

A series of disinfectant compositions were prepared by mixing the ingredients indicated in the following tables 1-9.

TABLE 1

TABLE 2

TABLE 3

TABLE 4

TABLE 5

TABLE 6

TABLE 7

TABLE 8

The comparison 1-6 and invention 7-8 compositions were subjected to a preliminary assessment of stability at three months, keeping the compositions at different storage temperatures as indicated in table 10. Subsequently, the comparison composition 1 and the invention compositions 7-8 were subjected to an accelerated stability assessment according to the CIPAC method at 54°C for 2 weeks and at 40°C for 8 weeks. A preliminary assessment of the bactericidal activity was conducted in parallel according to the UNI EN 1276:2019 standard on Pseudomonas aeruginosa ATCC 15442, of the virucidal activity according to the UNI EN 14476:2019 standard su Poliovirus type 1 (Sabin), and of the fungicidal/yeasticidal activity according to the UNI EN 1650:2019 standard on Candida albicans ATCC 10231 .

The results are summarized in the following table 10.

TABLE 10

The data in Table 10 confirmed that the invention compositions met all the required stability and activity parameters, while the comparison compositions failed in stability tests and/or in at least one activity test.

In particular, the comparison compositions 1 and 2 despite passing the stability tests, failed the virucidal activity test, the compositions 3 and 4 failed the stability tests, and for this reason the activity tests were suspended despite the positive results of virucidal and fungicidal activity. On the contrary, the compositions 5 and 6 despite being very stable, failed the fungicidal activity tests, so subsequent stability and activity assessments were not carried out.

It is worth noting that the composition 6 comprised the same active ingredients of the compositions 7 and 8, but in lower concentrations.

The compositions 7 and 8 of the invention, comprising amounts of hydrogen peroxide greater than 2% and of phenoxyethanol greater than 1 %, in combination with a mixture of surfactants derived from coconut oil fatty acids of nonionic (Glyceryl ether-2 cocoate and DEA Cocammide) and amphoteric (Disodium cocoanfodiacetate) type, showed a good stability and effectiveness in all the activity tests.

Example 2

In view of the positive results of the preliminary tests of activities, the composition 8 of the invention has been the object of a complete assessment of bactericidal activity on Enterocossus hirae ATCC 10541 , Escherichia coli K12 NCTC 10538, Staphylococcus aureus ATCC 6538 and Pseudomonas aeruginosa ATCC 15442 according to the UNI EN 1276:2019 standard.

The test has been carried out with 50% v/v dilution with a contact time of 60 seconds at 20°C in presence of 3 g/l of bovine albumin (dirty condition).

The results have confirmed that the composition 8 of the invention showed bactericidal activity against all microorganisms used.

Example 3

In view of the positive results of the preliminary tests of activities, the composition 8 of the invention has been the subject of a comprehensive assessment of the virucidal activity on Adenovirus type 5, Adenoid 75 strain, ATCC VR-5, Murine Norovirus, S99 Berlin strain, RVB-0651 and Poliovirus type 1 (Sabin), according to the UNI EN 14476:2019 standard.

The test has been carried out with 50% v/v dilution with a contact time of 120 seconds at 20°C in presence of 3 g/l of bovine albumin and 3 ml/l of erythrocytes (dirty condition). The results have confirmed that the composition 8 of the invention showed virucidal activity against all viruses used.

Example 4

In view of the positive results of the preliminary tests of activities, the composition 8 of the invention has been the subject of a comprehensive assessment of the fungicidal activity on Candida albicans ATCC 10231 according to the UNI EN 1650:2019 standard.

The results have confirmed that the composition 8 of the invention showed fungicidal activity.

Example 5

The composition 8 of the invention has finally been assessed according to the UNI EN 1499:November 2013 standard on a panel of 12 volunteers, measuring the logarithmic reduction of the concentration of Escherichia coli K12 NCTC 10538 after handwashing for 60 seconds with 4 ml of the test composition and subsequent rinsing for 10 seconds with tap water. The result of the test has confirmed a statistically significant reduction according to the Wilcoxon method.

The present invention has been described with reference to some preferred embodiments. Various modifications can be made to the above described embodiments, while remaining within the scope of protection of the invention as defined by the following claims.

Claims

1. A water-based disinfectant composition comprising (i) hydrogen peroxide, (ii) phenoxyethanol, (iii) at least one nonionic surfactant derived from coconut oil fatty acids, and (iv) at least one amphoteric surfactant derived from coconut oil fatty acids, wherein

• the amount of said hydrogen peroxide is more than 2 percent by weight relative to the weight of said composition,

• the amount of said phenoxyethanol is more than 1 percent by weight relative to the weight of said composition, and

• the total amount of said at least one nonionic surfactant derived from coconut oil fatty acids and said at least one amphoteric surfactant derived from coconut oil fatty acids is equal to or greater than 2.75 percent by weight relative to the weight of said composition.

2. The disinfectant composition according to claim 1 , wherein said hydrogen peroxide is present in an amount equal to or less than 3% by weight relative to the weight of said composition.

3. The disinfectant composition according to claim 1 , wherein said phenoxyethanol is present in an amount equal to or less than 2% by weight relative to the weight of said composition.

4. The disinfectant composition according to any one of the preceding claims, wherein the total amount of said at least one nonionic surfactant derived from coconut oil fatty acids and said at least one amphoteric surfactant derived from coconut oil fatty acids is 3% or more, preferably between 3.5% and 15%, more preferably between 4% and 10%, by weight relative to the weight of said composition.

5. The disinfectant composition according to any of the preceding claims, wherein said at least one nonionic surfactant derived from coconut oil fatty acids is chosen in the group consisting of coco monoethanolamide (MEA cocamide), coco diethanolamide (DEA cocamide), coco monoisopropanolamide (MIPA cocamide), methyl MEA cocamide, glyceryl cocoate, PEG-4 glyceryl cocoate, PEG-7 glyceryl cocoate, PEG-18 glyceryl cocoate, PEG-30 glyceryl cocoate, PEG-80 glyceryl cocoate, glyceryl ether cocoate, glyceryl ether-2 cocoate, glycerether-7 cocoate, glycerether-17 cocoate, PEG-9 cocoglyceride, cocoglucoside, and mixtures thereof.

6. The disinfectant composition according to any one of the preceding claims, wherein said disinfectant composition comprises at least one nonionic surfactant derived from coconut oil fatty acids in an amount between 2% and 15%, preferably between 2.5% and 12%, more preferably between 3% and 10% by weight relative to the weight of the composition.

7. The disinfectant composition according to any of the preceding claims, wherein said at least one amphoteric surfactant derived from coconut oil fatty acids is chosen in the group consisting of sodium cocoamphoacetate, disodium cocoamphodiacetate, coco betaine, cocoamidopropyl betaine, cocodimethylcarboxymethyl betaine, cocodimethylsulfopropyl betaine disodium cocoamphopropionate, cocam idopropyl hydroxysultaine, cocoamphocarboxyglycinate, sodium cocoamphohydroxypropylsulfonate, cocamine oxide, dihydroxyethylcocamine oxide, cocamidopropylamine oxide, and mixtures thereof.

8. The disinfectant composition according to any one of the preceding claims, wherein said disinfectant composition includes at least one amphoteric surfactant derived from coconut oil fatty acids in an amount between 0.10% and 0.50%, preferably between 0.15% and 0.30%, more preferably between 0.20% and 0.25% by weight relative to the weight of the composition.

9. The disinfectant composition according to any one of the preceding claims, wherein said disinfectant composition comprises water in an amount equal to or greater than 50%, preferably equal to or greater than 60%, more preferably equal to or greater than 70% by weight relative to the weight of the composition.