FR3117336A1 - NEW DISINFECTANT COMPOSITION - Google Patents

Abstract

NEW DISINFECTANT COMPOSITION The subject of the present invention is a new disinfectant composition comprising a mixture of phenol, aldehyde and alcohol, and its use for disinfecting a surface or in cosmetics for disinfecting the skin, in particular the hands.

Description

NEW DISINFECTANT COMPOSITION

The subject of the present invention is a new disinfectant composition comprising a mixture of phenol, aldehyde and alcohol, and its use for disinfecting a surface or in cosmetics for disinfecting the skin, in particular the hands.

Maintaining proper disinfection and following effective hygiene practices ensures a healthy lifestyle and reduced risk of adverse infection outbreaks. In the current health context, disinfection operations for hands and surfaces have become key in the fight against the transmission of viruses such as COVID-19.

Public places such as hospitals, religious/public/office buildings, restaurants form a virtual abode of disease-causing microorganisms. Apart from public places, spaces in the home like the kitchen and bathroom are also home to many such organisms. A disinfection operation consists of a voluntary and momentary elimination of certain germs, so as to stop or prevent an infection or the risk of infection or superinfection by pathogenic and/or undesirable micro-organisms or viruses. Disinfection involves eliminating or killing microorganisms or inactivating pathogenic viruses from contaminated environments, materials or materials by altering their structure or inhibiting their metabolism or some of their vital functions. The disinfectant used may have:

• an action of inhibiting the growth of microorganisms - in the case of bacteria we speak of bacteriostatic action;
• a lethal action on micro-organisms - in the case of bacteria we speak of bactericidal action.

According to current standards, disinfection must kill 99.999% of the targeted germs (thus divide the number of germs by 100,000).

In addition, practicing hand hygiene by hydro-alcoholic friction has become a procedure recommended by the WHO, which makes it possible to improve compliance by users and to respect the recommendations relating to good hygiene practices. Hydroalcoholic solutions with bactericidal, virucidal and fungicidal properties, without a cleaning effect, are usually used.

The compositions allowing the disinfection of surfaces mainly comprise one or more antimicrobial agents. Most of the disinfectants available on the market contain chemical actives and synthetic agents such as halogenated compounds, plasticizers and alcohols. The antimicrobial agents mentioned above, although effective, are toxic in nature. Disposal of such compositions is dangerous because they contaminate the environment and in particular bodies of water. In addition to being dangerous for the environment, these compositions are also corrosive and often damage furniture and countertops in the long term.

Disinfectant compositions intended for use on the skin mainly comprise plasticizers dispersed in an alcoholic base. Several currently available disinfectant compositions suffer from lack of flammability and high volatility. Additionally, alcohols such as isopropyl alcohol and ethanol which are commonly employed in such compositions are aggressive to the skin. Alcohols generally cause excessive dryness of the skin and have also been reported to cause eczema and rashes.

Insofar as the use of disinfectant compositions has become widespread, both for cleaning surfaces and for cleaning hands, it remains interesting to identify new compositions allowing effective disinfection according to the standards in force while preserving the cleaned surfaces or the skin depending on the intended use.

However, it has now been found that a combination of substances which can be obtained in particular from essential oils used in perfumery allows effective disinfection according to the standards in force, while preserving the cleaned surfaces or the skin according to the intended use. .

Thus, the subject of the present invention is a disinfectant composition comprising:

• at least one phenol of general formula (I)

(I)

wherein the R ¹ to R ⁵ substituents are independently selected from hydrogen or hydroxy, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ - alkynyl or C ₁ -C ₆ -alkoxy;

• at least one aldehyde of general formula (II)

(II)

wherein R ⁶ is C ₁ -C ₁₅ -alkyl; C ₂ -C ₁₅ -alkenyl; C ₂ -C ₁₅ -alkynyl; C ₁ -C ₁₅ -alkoxy; phenyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; isopropylphenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-; And

• at least one alcohol of general formula (III)

(III)

in which :

• R ⁷ and R ⁸ are independently selected from hydrogen or hydroxy, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl or C ₁ -C ₆ -alkoxy; And
• R ⁹ is chosen as being a C ₁ -C ₁₅ -alkyl group; C ₂ -C ₁₅ -alkenyl; C ₂ -C ₁₅ -alkynyl; C ₁ -C ₁₅ -alkoxy; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-;

in a ratio (w/w/w) phenol:aldehyde:alcohol ranging from 0.01:0.01:1 to 100:100:1.

The composition according to the present invention allows effective disinfection according to the standards in force of surfaces or of the skin, in particular of the hands. In addition, since the phenols, aldehydes and alcohols used in the composition can in particular be obtained from essential oils used in perfumery, the compositions according to the invention preserve the cleaned surfaces such as the skin.

In the context of the present invention:

- “C _x -C _y -alkyl” means a saturated hydrocarbon chain, linear or branched, and comprising from x to y carbon atoms;

- “C _x -C _y -alkenyl” is understood to mean a linear or branched hydrocarbon chain, comprising from x to y carbon atoms and at least one double bond;

- “C _x -C _y -alkynyl” means a linear or branched hydrocarbon chain, comprising from x to y carbon atoms and at least one triple bond;

- the term "C ₁ -C ₆ -alkoxy" means a group -O- (C _x -C _y -alkyl);

- “anisic alcohol” denotes (4-methoxyphenyl)methanol or 4-methoxybenzyl alcohol, the CAS number of which is 105-13-5;

- “benzyl alcohol” designates phenylmethanol, the CAS number of which is 100-51-6;

- "cinnamic alcohol" denotes ( 2E )-3-phenylprop-2-en-1-ol or styron, the CAS number of which is 104-54-1;

- “cuminic alcohol” denotes (4-propan-2-ylphenyl)methanol, the CAS number of which is 536-60-7;

- “isoamyl alcohol” denotes 3-methylbutan-1-ol, the CAS number of which is 123-51-3;

- “phenylethyl alcohol” designates 2-phenylethanol whose CAS number is 60-12-8;

- “phenylpropyl alcohol” designates 3-phenylpropan-1-ol, the CAS number of which is 122-97-4;

- “styralic alcohol” designates 1-phenylethanol whose CAS number is 98-85-1;

- "cinnamic aldehyde" denotes 3-phenylpropenal or cinnamaldehyde, the CAS number of which is 104-55-2;

- “Cuminic aldehyde” denotes 4-proan-2-yl-benzaldehyde or cuminaldehyde, the CAS number of which is 122-03-2;

- "cyclamen aldehyde" denotes 3-(4-isopropylphenyl)-2-methylpropanal or cyclamal, the CAS number of which is 103-95-7;

- "hydratropic aldehyde" denotes 2-phenylpropanal, the CAS number of which is 93-53-8;

- "lauric aldehyde" means C12-lauric aldehyde or C12 aldehyde, the CAS number of which is 112-54-9;

- “mandarin aldehyde” denotes (E)-dodec-2-enal, the CAS number of which is 20407-84-5;

- “phenylacetic aldehyde” denotes phenylacetaldehyde, the CAS number of which is 122-78-1;

- "aldehyde syringa" designates the compound whose CAS number is 104-09-6;

- “undecylenic aldehyde” designates 10-undecanal or aldehyde-C11-undecylenic whose CAS number is 112-45-8;

- "undecyl aldehyde" refers to C11-undecyl aldehyde, the CAS number of which is 112-44-7;

- “anisaldehyde” denotes 4-methoxybenzaldehyde, the CAS number of which is 123-11-5;

- "benzaldehyde" refers to benzoic aldehyde, the CAS number of which is 100-52-7;

- “carvacrol” denotes 2-methyl-5-(propan-2-yl)phenol, the CAS number of which is 499-75-2;

- "eugenol" denotes 4-allyl-2-methoxyphenol, the CAS number of which is 97-53-0;

- “chavicol” denotes 4-allylphenol, the CAS number of which is 501-92-8;

- “citral” denotes either 3,7-dimethyl-2,6-octadienal or lemonal, the CAS number of which is 5392-40-5; the trans or citral A or geranial isomer whose CAS number is 141-27-5; or the cis or citral B or neral isomer whose CAS number is 106-26-3. Preferably, “citral” denotes 3,7-dimethyl-2,6-octadienal, the CAS number of which is 5392-40-5;

- “Citronellol” denotes 3,7-dimethyloct-6-en-1-ol, the CAS number of which is 106-22-9;

- “creosol” denotes 2-methoxy-4-methylphenol or 4-methylguaiacol, the CAS number of which is 93-51-6;

- “decanal” denotes caprinaldehyde or C10 aldehyde, the CAS number of which is 112-31-2;

- “decanol” denotes decan-1-ol or C10 alcohol whose CAS number is 112-30-1;

- “4-ethylguaiacol” denotes 4-methyl-2-methoxyphenol, the CAS number of which is 2785-89-9;

- “dodecanol” denotes dodecan-1-ol or lauryl alcohol or lauryl alcohol whose CAS number is 112-53-8;

- “guaiacol” denotes 2-methoxyphenol or orthomethoxyphenol, the CAS number of which is 90-05-1;

- “geraniol” designates (2E)-3,7-dimethylocta-2,6-dien-1-ol or trans -3,7-dimethyl-2,6-octadien-1-ol whose CAS number is 106- 24-1;

- “heptanal” designates heptan-1-al or aldehyde C07 whose CAS number is 111-71-7;

- “hexanal” denotes n-hexanal or C06 aldehyde or capronaldehyde, the CAS number of which is 66-25-1;

- “isoeugenol” designates without distinction 2-methoxy-4-(prop-1-en-1-yl)phenol whose CAS number is 97-54-1; its “trans” or “E” form, the CAS number of which is 5932-68-3; or its “cis” or “Z” form whose CAS number is 5912-86-7. Preferably, “isoeugenol” designates 2-methoxy-4-(prop-1-en-1-yl)phenol whose CAS number is 97-54-1;

- "2-methyldecanal" refers to the C11 MOA aldehyde, the CAS number of which is 19009-56-4;

- "2-methylundecanal" refers to the aldehyde C12 MNA, the CAS number of which is 110-41-8;

- “nerol” designates ( Z )3,7-dimethyl-2,6-octadien-l-ol or cis -3,7-dimethyl-2,6-octadien-8-ol whose CAS number is 106-25 -2;

- “nerolidol” designates without distinction 3,7,11-trimethyldodeca-1,6,10-triene-3-ol, the CAS number of which is 7212-44-4; its “trans racemic” form, the CAS number of which is 3790-78-1; its “cis racemic” form, the CAS number of which is 40716-66-3; or (S)-Z-nerolidol whose CAS number is 142-50-7. Preferably, “nerolidol” denotes its “trans racemic” form, the CAS number of which is 3790-78-1;

- “nonanol” denotes nonan-1-ol or C09 alcohol, the CAS number of which is 143-08-8;

- "octanal" designates caprylic aldehyde or C08 aldehyde, the CAS number of which is 124-13-0;

- “octanol” designates octan-1-ol whose CAS number is 111-87-5;

- “salicylaldehyde” denotes 2-hydroxybenzaldehyde or salicylic aldehyde, the CAS number of which is 90-02-8;

- "tridecanol" refers to isotridecanol or tridecyl alcohol or oxo C13 alcohol whose CAS number is 68526-86-3;

- “trimethylhexanol” denotes trimethyl hexan-1-ol or oxo C9 alcohol, the CAS number of which is 3452-97-9;

- “thymol” denotes 5-methyl-2-(propan-2-yl)-phenol, the CAS number of which is 89-83-8;

- “undecanol” denotes undecan-1-ol, the CAS number of which is 112-42-5;

- “veratraldehyde” denotes 3,4-dimethoxybenzaldehyde or veratric aldehyde, the CAS number of which is 120-14-9;

- “4-vinylguaiacol” denotes 4-ethenyl-2-methoxyphenol or 2-methoxy-4-vinylphenol, the CAS number of which is 7786-61-0; And

- the term "disinfectant composition" means any composition allowing the disinfection (or to disinfect) of a surface or of the skin (i.e. cosmetic use), that is to say the destruction of 99.999% of the targeted germs (therefore dividing per 100,000 the number of said germs). Such a composition can in particular have a bactericidal and/or virucidal action.

Finally, in the context of the present invention, and unless otherwise stated, the proportions expressed in % correspond to mass percentages relative to the total weight of the entity considered.

The present invention therefore relates to a disinfectant composition comprising at least one phenol of general formula (I) as defined above, at least one aldehyde of general formula (II) as defined above and at least one alcohol of general formula (III ) as defined previously, in a ratio (w/w/w) phenol:aldehyde:alcohol ranging from 0.01:0.01:1 to 100:100:1. Preferably, the subject of the present invention is a composition as described above having the following characteristics, taken alone or in combination:

- the composition comprises at least one phenol of general formula (I) in which R ¹ to R ⁵ are chosen independently of each other as being a hydrogen atom or a hydroxy, methyl, ethyl, propyl, isopropyl or butyl group, tert-butyl, ethylene, propylene, butyl-1-ene, butyl-2-ene, 2-methylpropylene, acetylene, propyne, but-1-yne, but-2-yne, methoxy, ethoxy, propoxy or butoxy. Preferably, the composition comprises at least one phenol of general formula (I) in which R ¹ to R ⁵ are chosen independently of each other as being a hydrogen atom or a hydroxy, methyl, ethyl, isopropyl, ethylene, propylene or methoxy. More preferably, the composition comprises at least one phenol chosen from chavicol, guaiacol, creosol, 4-ethyl guaiacol, 4-vinyl guaiacol, isoeugenol, eugenol, thymol and carvacrol. More preferably, the composition comprises at least one phenol chosen from eugenol, thymol and carvacrol. Most preferably, the composition comprises a combination of eugenol, thymol and carvacrol;

- the composition comprises at least one aldehyde of general formula (II) in which R ⁶ is chosen as being a C ₅ -C ₁₂ -alkyl group; C ₅ -C ₁₂ -alkenyl; C ₁ -C ₅ -alkoxy; phenyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; isopropylphenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-. More preferably, the composition comprises at least one aldehyde chosen from anisaldehyde, benzaldehyde, citral, hexanal, heptanal, octanal, decanal, 2-methyldecanal, undecylenic aldehyde, undecyl aldehyde, lauryl aldehyde, 2-methylundecanal, cinnamic aldehyde, cumin aldehyde, cyclamen aldehyde, mandarin aldehyde, phenylacetic aldehyde, salicylaldehyde, syringa aldehyde, veratraldehyde and l hydratropic aldehyde. Quite preferably, the composition comprises at least one aldehyde chosen as being citral;

- the composition comprises at least one alcohol of general formula (III) in which R ⁷ and R ⁸ are chosen independently of each other as being a hydrogen atom or a hydroxy, methyl, ethyl, propyl, isopropyl group , butyl, tert-butyl, ethene, propene, but-1-ene, but-2-ene, 2-methylpropene, acetylene, propyne, but-1-yne, but-2-yne, methoxy, ethoxy, propoxy or butoxy ; and R ⁹ is selected as being a C ₅ -C ₁₂ -alkyl group; C ₅ -C ₁₂ -alkenyl; C ₅ -C ₁₂ -alkynyl; C ₅ -C ₁₂ -alkoxy; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-. More preferably, the composition comprises at least one alcohol chosen from anisic alcohol, benzyl alcohol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, trimethylhexanol, cinnamic alcohol, cumin alcohol, isoamyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, styralic alcohol, citronellol, geraniol, nerol and nerolidol. Most preferably, the composition comprises at least one alcohol chosen as being nerolidol; and or

- the ratio (w/w/w) phenol:aldehyde:alcohol varies from 0.1:0.1:1 to 10:10:1. Preferably the ratio (w/w/w) phenol:aldehyde:alcohol ranges from 0.5:0.5:1 to 5:5:1. Most preferably, the ratio (w/w/w) phenol:aldehyde:alcohol ranges from 1:1:1 to 3:3:1.

As examples of disinfectant compositions according to the present invention, mention may in particular be made of compositions comprising one of the following phenol/aldehyde/alcohol combinations in the ratio (w/w/w) phenol:aldehyde:alcohol defined above:

- eugenol, citral and nerolidol;

- thymol, citral and nerolidol;

- carvacrol, citral and nerolidol;

- eugenol, thymol, citral and nerolidol;

- eugenol, carvacrol and nerolidol;

- thymol, carvacrol, citral and nerolidol;

- eugenol, thymol, carvacrol, citral and nerolidol.

Quite preferably, the subject of the present invention is a disinfectant composition as defined above comprising eugenol, thymol, carvacrol, citral and nerolidol in a ratio (w/w/w) phenol:aldehyde :alcohol as defined above.

The phenols, aldehydes and alcohols used to prepare the composition according to the present invention can be synthetic or, preferably, natural. When these compounds are natural, they can be added to the composition according to the present invention in various forms, in particular in an isolated form or in the form of essential oils. So, for example:

- the eugenol present in the composition can be provided in an isolated form or in the form of essential oil of cloves, clove cloves, clove leaves, cinnamon leaves, pepper leaves, berries chilli, Dominica berries, basil or Ceylon cinnamon bark;

- the thymol present in the composition can be provided in an isolated form or in the form of essential oil of thyme, garden savory or wild thyme;

- the carvacrol present in the composition can be provided in an isolated form or in the form of essential oil of oregano, thyme, garden savory, wild thyme or Alaskan cypress;

- the citral present in the composition can be provided in an isolated form or in the form of essential oil of lemon, lemon litsea, lemon myrtle, lemongrass, lemon balm, verbena or lemon petitgrain; And

- the nerolidol present in the composition can be provided in an isolated form or in the form of essential oil of neroli, cabreuva, peimou or verbena; or in the form of orange blossom absolute or balsam of Peru.

The compositions according to the present invention can therefore be used in cosmetics for disinfecting the skin. To do this, the compositions according to the present invention may be in any pharmaceutical form suitable for its topical application.

Cosmetic compositions comprising the compounds as defined above can be formulated in liquid, pasty or solid form, and more particularly in the form of ointments, creams, milks, ointments, powders, soaked pads (wipes), solutions, gels, sprays, foams, suspensions or sticks. They can also be in the form of suspensions of microspheres or nanospheres, of lipid or polymeric vesicles, or of polymeric or gelled patches allowing controlled release, but also in the form of rinse-off products such as shower gels, bath products (salts, foaming, etc.).

These cosmetic compositions contain the compounds as defined above at contents ranging from 0.0001% to 10% by total weight of the composition, preferably from 0.001% to 1% by total weight of the composition.

For the preparation of these compositions, the compounds as defined above are mixed with the excipients conventionally used in the cosmetics field.

The compositions comprising the compounds as defined above can take the form of perfuming compositions possessing cosmetic activity, such as for example the compositions of the Actiscent® range.

The cosmetic compositions comprising the compounds as defined previously can take the form of a cream in which the said fraction is combined with the excipients commonly used in cosmetology.

These compositions can also take the form of gels in the appropriate excipients such as cellulose esters or other gelling agents, such as carbopol, sepinov (polyacrylate) or guar gum.

These compositions can also take the form of a lotion or a solution in which the compounds as defined above are in encapsulated form. The microspheres can for example consist of fatty substances, agar and water. The compounds as defined above can be incorporated into vectors of the liposome, glycosphere or cyclodextrin type, in chylomicrons, macro-, micro-, nano-particles as well as macro-, micro- and nanocapsules and also be absorbed onto powdery organic polymers, talcs, bentonites and other mineral carriers.

These emulsions enjoy good stability and can be stored for the time necessary for use at temperatures between 0 and 50°C without there being any sedimentation of the constituents or separation of the phases.

The cosmetic compositions comprising the compounds as defined above may also contain additives or adjuvants customary in cosmetology, such as for example antimicrobial agents or perfumes, but also extraction or synthetic lipids, gelling and viscosifying polymers, surfactants. - active ingredients and emulsifiers, water- or fat-soluble active ingredients, plant extracts, tissue extracts, marine extracts, synthetic active ingredients.

The cosmetic compositions comprising the compounds as defined above can also comprise other complementary active principles chosen for their action, for example for the moisturizing effect, the anti-ageing effect, the antioxidant activity, the anti-aging activity. -radical, the healing effect, the tensor effect, the chelating activity, the complexing and sequestering activity, the soothing effect, the anti-redness effect, the emollient activity, the activity involved in cell renewal, activity modulating the inflammatory response, but also sun protection, anti-irritant activity, cellular nutrition, cellular respiration, skin tone.

When the cosmetic compositions comprising the compounds as defined above contain additional active principles, these are generally present in the composition at a sufficiently high concentration for them to be able to exert their activity.

The compositions according to the present invention can also be used to disinfect surfaces. To do this, the compositions according to the present invention may be in any pharmaceutical form suitable for such use.

The compositions according to the present invention therefore allow effective disinfection according to the standards in force while preserving the cleaned surfaces or the skin depending on the intended use.

A subject of the present invention is therefore also the use of a composition as defined above for the disinfection of a surface, as well as the use of a composition as defined above in cosmetics, in particular for the disinfection of the skin. , especially the hands.

The present invention is illustrated without limitation by the following examples.

Example 1 - Composition according to the invention

Preparation

A composition comprising:

- eugenol obtained from cloves;

- thymol obtained from ajwain;

- carvacrol obtained from oregano;

- citral obtained from lemon litsea ( Litsea cubeba );

- nerolidol obtained from cabreuva.

To do this, the various ingredients are weighed and then mixed together in the presence of triethyl citrate (TEC).

The composition reported in the following Table 1 is obtained.

Ingredient % (w/w/w) Eugenol 16.7% Thymol 3.4% carvacrol 16.7% citral 15.1% Nerolidol 16.7% TEC (solvent) 31.4

Table 1 – Composition according to the invention

Example 2 - Bactericidal efficacy compositions of the invention

2.1 - Experimental protocol

The product (compound alone or composition) diluted in dipropylene glycol is incorporated into a specific culture medium at the time of distribution into 96-well microplates.

The microplates are then seeded with a known solution of Escherichia coli .

After 24 hours of incubation at 37°C, a measurement of the Minimum Inhibitory Concentration (MIC) is carried out using a resazurin test (7-hydroxy-3H-phenoxazin-3-one 10-oxide), a blue dye which is reduced to pink-colored resofurine in the presence of bacterial growth.

The bacterial growth inhibitory activity of the product is evaluated in relation to controls and measured using the different dilutions carried out.

2.2 - Results

Results obtained

The results obtained are reported in Table 2 below.

Compound (% of composition 1) or composition MIC (in ppm +/- 500 ppm) Eugenol 3000 Thymol 3676 carvacrol 2395 citral 29000 Nerolidol 40000 Membership 1 1500

Table 2 – Bactericidal efficacy

Conclusion

The results obtained prove the existence of a bactericidal effect for composition 1 and the existence of a synergy of action between the different ingredients.

Example 3 - Bactericidal efficacy of the compositions of the invention

3.1 - Experimental protocol

To evaluate the bactericidal efficacy of the compositions according to the invention, the experimental protocol defined in standard EN-1276 (phase 2, step 1) was followed.

The experimental conditions adopted are as follows:

• Number of boxes: 2 per test;
• Membrane filtration method
• Rinsing liquid: Trytone 1 g/l, NaCl 9 g/l, Lecithin 3 g/l;
• Test temperature: 20°C;
• Interfering substance: Bovine albumin: 0.3 g/l
• Test microorganism: Escherichia coli ATCC 10536;
• Incubation temperature: 37°C;
• Diluent used for product test solutions: hard water; And
• Appearance of product test solutions: clear.

Different concentrations (0.05%, 0.1% and 0.2%) of composition 1 in the culture medium were tested.

To be effective, the log R value at the concentration tested must be greater than 5.

3.2 - Results

The results obtained are reported in Table 3 below.

% (w/w) of composition 1 in the culture medium Log R (No=7.51) 0.05% 4.24 0.1% 5.07 0.2% 5.37

Table 3 – Bactericidal efficacy of composition 1

Conclusion

Under the (mandatory and additional) conditions of the test performed, the minimum effective concentration of composition 1 to eliminate 99.999% of E. coli bacteria is 0.1%, which demonstrates the effectiveness of the composition at a very low level of concentration compared to other products. For comparison, ethanol demonstrates similar efficacy at a rate greater than 4%.

Example 4 - Virucidal efficacy compositions of the invention

4.1 - Experimental protocol

To assess the bactericidal efficacy of the compositions according to the invention, the experimental protocol defined in standard EN-14476 (phase 2, step 1) was followed.

The experimental conditions adopted are as follows:

• Viral strain studied: Human coronavirus 229E (HCo-229E), ATCC VR-740 (passage no. 3);
• Cell line and passage number: MRC-5, for propagation of Human coronavirus 229E (HCo-229E) (passage #27+4);
• Diluent used: carbonated water;
• Interfering substance: 0.3 g/l bovine albumin (clean conditions);
• Contact: 1 min +/- 5 sec;
• Incubation temperature: 20°C +- 1°C;
• Neutralization method: filtration with Microspin™ S400HR column;
• Culture medium: MEM 10% FCS;
• Maintenance medium: MEM 2% FCS; And
• Cell incubation conditions: 34° C., 5% CO ₂ .

Different concentrations (0.01%, 0.1% and 0.2%) of composition 1 in the culture medium were tested.

To be effective, the log R value at the concentration tested must be greater than 4.

4.2 - Results

Results obtained

% (w/w) of composition 1 in the culture medium Log R (No=5.5) 0.01% 2.25 0.1% 3.75 0.2% >4

Conclusion

According to the UNI EN 14476+A2:2019 standard and under the test conditions detailed above, composition 1 has virucidal activity against human coronavirus 229E (HCo-229E) at a concentration of 0.2%. These results demonstrate the effectiveness of the composition at a very low level of concentration compared to other products. For comparison, formaldehyde demonstrates similar efficacy at a rate of 0.7%.

Claims (13)

Disinfectant composition comprising:

• at least one phenol of general formula (I)

(I)
in which the substituents R¹to R⁵are selected independently of each other as being a hydrogen atom or a hydroxy group, C₁-VS₆-alkyl, C₂-VS₆-alkenyl, C₂-VS₆-alkynyl or C₁-VS₆-alkoxy;

• at least one aldehyde of general formula (II)

(II)
in which R⁶as being a group C₁-VS₁₅-alkyl; VS₂-VS₁₅-alkenyl; VS₂-VS₁₅-alkynyl; VS₁-VS₁₅-alkoxy; phenyl optionally substituted by one or more substituents chosen from a group C₁-VS₆-alkyl or C₁-VS₆-alkoxy; benzyl optionally substituted by one or more substituents chosen from a group C₁-VS₆-alkyl or C₁-VS₆-alkoxy; phenyl-C₁-VS₆-alkyl-; isopropylphenyl-C₁-VS₆-alkyl-; or phenyl-C₂-VS₆-alkenyl-; And

• at least one alcohol of general formula (III)

(III)
in which :

• R ⁷ and R ⁸ are independently selected from hydrogen or hydroxy, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl or C ₁ -C ₆ -alkoxy; And
• R ⁹ is chosen as being a C ₁ -C ₁₅ -alkyl group; C ₂ -C ₁₅ -alkenyl; C ₂ -C ₁₅ -alkynyl; C ₁ -C ₁₅ -alkoxy; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-;

in a ratio (w/w/w) phenol:aldehyde:alcohol ranging from 0.01:0.01:1 to 100:100:1. Composition according to Claim 1, characterized in that it comprises at least one phenol of general formula (I) in which R ¹ to R ⁵ are chosen independently of each other as being a hydrogen atom or a hydroxy, methyl , ethyl, propyl, isopropyl, butyl, tert-butyl, ethylene, propylene, butyl-1-ene, butyl-2-ene, 2-methylpropylene, acetylene, propyne, but-1-yne, but-2-yne, methoxy , ethoxy, propoxy or butoxy. Composition according to Claim 2, characterized in that it comprises at least one phenol chosen from chavicol, guaiacol, creosol, 4-ethyl guaiacol, 4-vinyl guaiacol, isoeugenol, eugenol, thymol and carvacrol. Composition according to Claim 3, characterized in that it comprises at least one phenol chosen from eugenol, thymol and carvacrol. Composition according to any one of Claims 1 to 4, characterized in that it comprises at least one aldehyde of general formula (II) in which R ⁶ is chosen as being a C ₅ -C ₁₂ -alkyl group; C ₅ -C ₁₂ -alkenyl; C ₁ -C ₅ -alkoxy; phenyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; isopropylphenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-. Composition according to Claim 5, characterized in that it comprises at least one aldehyde chosen from anisaldehyde, benzaldehyde, citral, hexanal, heptanal, octanal, decanal, 2-methyldecanal, undecylenic aldehyde, lauryl aldehyde, 2-methylundecanal, cinnamic aldehyde, cumin aldehyde, cyclamen aldehyde, mandarin aldehyde, phenylacetic aldehyde, salicylaldehyde, syringa aldehyde, veratraldehyde and hydratropic aldehyde. Composition according to Claim 6, characterized in that it comprises at least one aldehyde chosen as being citral. Composition according to any one of Claims 1 to 7, characterized in that the composition comprises at least one alcohol of general formula (III) in which:

• R ⁷ and R ⁸ are chosen independently of each other as being a hydrogen atom or a hydroxy, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, ethene, propene, but-1-ene group , but-2-ene, 2-methylpropene, acetylene, propyne, but-1-yne, but-2-yne, methoxy, ethoxy, propoxy or butoxy; And
• R ⁹ is chosen as being a C ₅ -C ₁₂ -alkyl group; C ₅ -C ₁₂ -alkenyl; C ₅ -C ₁₂ -alkynyl; C ₅ -C ₁₂ -alkoxy; benzyl optionally substituted by one or more substituents chosen from a C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy group; phenyl-C ₁ -C ₆ -alkyl-; or phenyl-C ₂ -C ₆ -alkenyl-.

Composition according to Claim 8, characterized in that it comprises at least one alcohol chosen from anisic alcohol, benzyl alcohol, octanol, nonanol, decanol, undecanol, dodecanol, cinnamic alcohol, cumin alcohol, isoamyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, styralic alcohol, citronellol, geraniol, nerol and nerolidol. Composition according to Claim 9, characterized in that it comprises at least one alcohol chosen as being nerolidol. Composition according to any one of Claims 1 to 10, characterized in that the ratio (w/w/w) phenol:aldehyde:alcohol varies from 0.5:0.5:1 to 5:5:1. Composition according to any one of Claims 1 to 11, characterized in that it comprises one of the following phenol/aldehyde/alcohol combinations:
- eugenol, citral and nerolidol;
- thymol, citral and nerolidol;
- carvacrol, citral and nerolidol;
- eugenol, thymol, citral and nerolidol;
- eugenol, carvacrol and nerolidol;
- thymol, carvacrol, citral and nerolidol; Or
- eugenol, thymol, carvacrol, citral and nerolidol. Use of a composition according to any one of Claims 1 to 12 for disinfecting a surface or for disinfecting the skin, in particular the hands.