JP7643982B2 - Diacetyl odor suppressant - Google Patents

Description

The present invention relates to a diacetyl odor suppressant that contains a specific fragrance as an active ingredient.

In our living environment, there are many malodorous molecules with different polarities and molecular weights. To eliminate the various malodorous molecules, various deodorizing methods have been developed. In general, deodorizing methods are broadly divided into biological methods, chemical methods, physical methods, and sensory methods. Among malodorous molecules, diketones, including diacetyl, can be deodorized through chemical reactions.

However, these malodorous substances often have a low threshold, making it difficult to deodorize them to a concentration that cannot be detected by chemical deodorization methods alone, and so sensory deodorization is often used in combination to deodorize them efficiently. Sensory deodorization mainly includes (1) a method using a fragrance in excess of the malodor, known as masking deodorization, (2) a method using a fragrance with strong characteristics different from the malodor, known as pairing deodorization, (3) a method of deodorizing by acclimatization using a fragrance that responds to the olfactory receptor to which the malodor responds, (4) a method of deodorizing by suppressing the response of the olfactory receptor to which the malodor responds, and (5) a method of deodorizing by modulating or blocking the signal from the olfactory cells.

Diacetyl is a naturally occurring diketone, and has been reported to be the main component of body odor that becomes more pronounced in people in their 30s and 40s. Diacetyl has the odor of oily sweat and has a low threshold. Patent Document 1 discloses an extract of at least one plant selected from the group consisting of tea and persimmon as a deodorizing ingredient for diacetyl.

JP 2001-198200 A

Therefore, the object of the present invention is to provide a novel diacetyl odor suppressant, etc.

The olfactory receptors that recognize odor molecules such as malodors are complex, and known fragrance ingredients do not necessarily suppress malodors such as diacetyl odor, and may even increase the malodor. The inventors discovered that a specific fragrance ingredient suppresses diacetyl odor, and thus completed the present invention.

That is, the present invention provides a diacetyl odor suppressant containing, as an active ingredient, one or more active ingredients selected from the group consisting of α-damascone, β-ionone, tricyclodecenyl propionate, rifalome, citral, β-damascone, nonanal, cis-6-nonenal, nerol, melonal, fenchol, lilial, anisaldehyde, dihydromyrcenol, linalool, geraniol, cyclamen aldehyde, terpineol, cis-jasmone, 3-phenyl-1-propanol, and ethyl linalool.

The present invention also provides a method for suppressing diacetyl odor, which includes a step of contacting the diacetyl odor suppressant with diacetyl.

The diacetyl odor suppressant provided by the present invention has a diacetyl odor suppression effect equal to or far superior to existing products.

The present invention uses as an active ingredient one or more selected from the group consisting of α-damascone, β-ionone, tricyclodecenyl propionate, rifarom, citral, β-damascone, nonanal, cis-6-nonenal, nerol, melonal, fenchol, lilial, anisaldehyde, dihydromyrcenol, linalool, geraniol, cyclamen aldehyde, terpineol, cis-jasmone, 3-phenyl-1-propanol, and ethyl linalool.

Of the above compounds, the following compounds are preferred: α-damascone, β-ionone, tricyclodecenyl propionate, rifalome, citral, β-damascone, nonanal, cis-6-nonenal, nerol, melonal, fenchol, lilial, anisaldehyde, dihydromyrcenol, linalool, geraniol, and cyclamen aldehyde. Among these, tricyclodecenyl propionate, nerol, melonal, lilial, geraniol, and cyclamen aldehyde are more preferred because they have low fragrance strength. Of these compounds, tricyclodecenyl propionate, nerol, and melonal are more preferred.

Each compound may be used alone, or two or more may be used in combination, so long as the diacetyl odor suppression effect is not impaired. Furthermore, these compounds may be used by adding other fragrance ingredients to prepare a blended fragrance. Such other fragrance ingredients are not particularly limited as long as they do not impair the diacetyl odor suppression effect, but examples of such ingredients include animal fragrances such as musk, spirit cat fragrance, and dragon's sprout fragrance, abies oil, acorn oil, almond oil, angelica root oil, peper oil, bergamot oil, perch oil, boerose oil, kayabuchi oil, gananga oil, capsicum oil, caraway oil, cardamom oil, cassia oil, celery oil, cinnamon oil, citronella oil, cognac oil, and coli. Examples of fragrances include vegetable fragrances such as under oil, cumin oil, camphor oil, basil oil, estugoran oil, eucalyptus oil, fennel oil, garlic oil, ginger oil, grapefruit oil, hops oil, lemon oil, lemongrass oil, nutmeg oil, mandarin oil, peppermint oil, orange oil, sage oil, star anise oil, turpentine oil, rosemary oil, eucalyptus oil, anise oil, lavender oil, cumin oil, cinnamon oil, and hiba oil. In addition, synthetic fragrances or artificial fragrances such as extracted fragrances can also be used as fragrances. Examples of such fragrances include hydrocarbon fragrances such as pinene and limonene, alcohol fragrances such as citronellol, menthol, borneol, benzyl alcohol, anise alcohol, and β-phenethyl alcohol, phenol fragrances such as anethole and eugenol, aldehyde fragrances such as n-butyraldehyde, isobutyraldehyde, hexylaldehyde, citronellal, benzaldehyde, and cinnamic aldehyde, carvone, menthone, camphor, acetophenone, and ketone fragrances, lactone fragrances such as γ-butyrolactone, coumarin, and cineol, and ester fragrances such as octyl acetate, benzyl acetate, cinnamyl acetate, butyl propionate, and methyl benzoate.

The diacetyl odor inhibitor can be used to eliminate or remove the diacetyl odor contained in sweat and body odor. The diacetyl odor inhibitor can be applied directly to the source of the diacetyl odor. If the diacetyl odor is caused by bacterial proliferation, in addition to applying the diacetyl odor inhibitor, an antibacterial treatment to inhibit bacterial proliferation may be performed.

The diacetyl odor inhibitor is expected to be incorporated into various deodorants, various air fresheners, body or face cleansers, laundry detergents, laundry softeners, cosmetics, and fragrance products. The diacetyl odor inhibitor is incorporated in a volatile state, including, but not limited to, liquid agents, sheets supported on a carrier such as fibers, gel agents, etc.

Examples include oil-type deodorants in which diacetyl odor suppressants or compounded fragrances prepared by mixing them as is or with a suitable volatile organic solvent are vaporized using a volatile medium, water-based deodorants in which diacetyl odor suppressants or compounded fragrances prepared by mixing them are dissolved in water using a surfactant or the like to form an aqueous solution, which is vaporized using a volatile medium, gel-type deodorants prepared by gelling these with a gelling agent, and deodorants absorbed in a highly water-absorbent resin.

The volatile organic solvent is not particularly limited, but examples thereof include volatile alcohols and volatile glycol ethers. Among these, examples of volatile alcohols include lower alcohols such as methanol, ethanol, 1-propanol, and 2-propanol, and examples of volatile glycol ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, butylene glycol monomethyl ether, 3-methoxy-1-butanol, and 3-methoxy-3-methyl-1-butanol.

The surfactant may be a nonionic surfactant, anionic surfactant, cationic surfactant, or amphoteric surfactant, either alone or in combination.
The nonionic surfactant is not particularly limited, but examples thereof include polyoxyethylene alkyl ethers, polyoxyalkylene alkyl ethers, polyoxyethylene hydrogenated castor oil ethers, polyoxyethylene fatty acid esters, polyoxyethylene alkylphenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, glycerin fatty acid esters, polyoxyethylene polyoxypropylene block polymers, polyoxyethylene alkylamine ethers, fatty acid alkanolamides, tertiary amine oxides, etc. The polyoxyethylene alkyl ethers have a polyoxyethylene chain length of 3 to 18, preferably 7 to 12, and the alkyl chain may be either linear or branched, with the alkyl chain length being 8 to 22, preferably 12 to 14. Examples of the fatty acid alkanolamide include monoethanolamide and diethanolamide of coconut oil fatty acid, stearic acid, and lauric acid, and examples of the tertiary amine oxide include lauryl dimethylamine oxide, coconut oil fatty acid dimethylamine oxide, lauroylaminopropyl dimethylamine oxide, octyl dimethylamine oxide, and myristyl dimethylamine oxide.

Examples of anionic surfactants that can be used include higher fatty acid soap, soap base, metal soap, triethanolamine N-acyl-L-glutamate, sodium N-acyl-L-glutamate, sodium alkyl sulfate, sodium alkyl sulfonate, sodium polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, sodium methyl coconut taurate (sodium N-cocoyl-N-methyl taurate), triethanolamine lauryl sulfate, sodium lauryl sulfate, sodium lauroyl sarcosine, sodium lauroyl methyl β-alanine solution, sodium lauroyl methyl taurate, and the like, which can be used alone or in combination of two or more.

As cationic surfactants, one or a mixture of two or more of ethyl lanolin fatty acid aminopropylethyldimethylammonium sulfate, alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, stearyltrimethylammonium chloride, benzalkonium chloride, benzethonium chloride, etc. can be used.

As amphoteric surfactants, one or more of the following may be used in combination: 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, alkyldiaminoethylglycine hydrochloride solution, lauryldimethylaminoacetate betaine, etc.

Examples of gelling agents include carrageenan, gellan gum, agar, gelatin, guar gum, pectin, locust bean gum, xanthan gum, tamarind gum, sodium alginate, isobutylene-maleic anhydride copolymer, carboxymethyl cellulose and other cellulose derivatives.

The water-absorbent resin is not particularly limited, but examples thereof include those containing polyacrylic acid or its salt, such as crosslinked polyacrylates, partially neutralized polyacrylates, crosslinked acrylic acid and/or its salt-acrylamide copolymers, crosslinked isobutylene-maleic anhydride copolymers, hydrolyzates of starch-acrylonitrile graft copolymers, (partially) neutralized starch-acrylic acid ester copolymers, saponified and partially saponified vinyl acetate-acrylic acid ester copolymers, hydrolyzates of acrylonitrile copolymers or acrylamide copolymers, and modified polyvinyl alcohols.

The diacetyl odor suppressant may contain other components that have a deodorizing effect as long as the effect of the active ingredient is not impaired, or any component used in a deodorant or deodorant, as appropriate for the purpose. Any known deodorant can be used as such other components that have a deodorizing effect, but examples include deodorizing active ingredients extracted from various parts of plants, such as leaves, petioles, fruits, stems, roots, and bark (e.g., green tea extract); organic acids such as lactic acid, gluconic acid, succinic acid, glutaric acid, adipic acid, malic acid, tartaric acid, maleic acid, fumaric acid, itaconic acid, citric acid, benzoic acid, and salicylic acid, various amino acids and their salts, glyoxal, oxidizing agents, flavonoids, catechins, and polyphenols; porous substances such as activated carbon and zeolite; inclusion agents such as cyclodextrins; photocatalysts; and various masking agents.

Examples of optional ingredients used in deodorants and deodorants include fragrances, powdered ingredients, liquid oils and fats, solid oils and fats, waxes, hydrocarbons, plant extracts, herbal ingredients, higher alcohols, lower alcohols, esters, long-chain fatty acids, surfactants (nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc.), sterols, polyhydric alcohols, moisturizers, water-soluble polymer compounds, thickeners, film-forming agents, bactericides, preservatives, UV absorbers, retention agents, cooling agents, warming agents, stimulants, sequestering agents, sugars, amino acids, organic amines, synthetic resin emulsions, pH adjusters, antioxidants, antioxidant assistants, oils, powders, capsules, chelating agents, inorganic salts, organic salt pigments, thickeners, bactericides, preservatives, antifungal agents, colorants, defoamers, bulking agents, modulators, organic acids, polymers, polymer dispersants, enzymes, enzyme stabilizers, etc.

In a second embodiment, a method for suppressing diacetyl odor is provided, comprising the step of contacting a diacetyl odor suppressor with diacetyl.

Potential sources of diacetyl odor include clothing, pillows, conference rooms, elevators, and other places where bacteria that produce diacetyl grow, but as used in this specification, the sources to which the diacetyl odor suppressant is directly applied do not include parts of the human body.

The contact can also be performed by applying a diacetyl odor inhibitor to the source of diacetyl or diacetyl odor. Application methods include scattering, spraying, coating, etc., and can be determined by a person skilled in the art as appropriate depending on the dosage form of the diacetyl odor inhibitor. It can also be combined with a known diacetyl odor suppression method. For example, if the diacetyl odor is caused by bacterial proliferation, in addition to applying the diacetyl odor inhibitor, an antibacterial treatment to suppress bacterial proliferation can be performed.

The timing of application is not particularly limited, and can be applied as soon as the diacetyl odor is perceived. From a preventative perspective, the diacetyl odor inhibitor may be applied in advance to areas where the diacetyl odor is expected to occur.

The present invention will be described in more detail below using examples. However, the present invention is not limited to the description of the following examples.

<Sensory test>
(Test sample)
The following test samples were used to test the deodorizing effect against diacetyl odor.

(Preparation of Masterbatch)
Diacetyl was dissolved in liquid paraffin to prepare solutions (0.0001 ppm, 0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 10 ppm, 100 ppm, 1000 ppm), and 5 g of each solution was soaked into pleated filter paper (diameter 185 mm) and placed in a 500 ml beaker. The beaker was sealed in a 10 liter bag, filled with odorless air, and left to stand at room temperature for 24 hours to prepare six types of master batch bags.

(Preparation of malodorous bags)
Air in the amounts shown in Table 2 was dispensed from the six types of master batch bags using a syringe and injected into a 3 liter odor bag filled with odorless air to prepare odor bags 1 to 8.

(Preparation of Fragrance Bags)
1 g of each of the fragrances in Table 1 was soaked in a pleated filter paper (diameter 90 mm) and placed in a 500 ml beaker. The beaker was sealed in a 10 liter bag, filled with odorless air, and left to stand at 25°C for 30 minutes to prepare a fragrance bag.

(Preparation of sample bags)
Another set of the malodor bags 1 to 8 was prepared, and 200 ml of air was taken from the fragrance bag and injected into each of them, to give sample bags 1 to 8 in that order.

(Pleasantness/unpleasantness of aroma, preference)
200 ml of the fragrance bag was taken and filled with odorless air to create a 3-liter bag, and the pleasantness or unpleasantness and strength of each fragrance were evaluated according to the following criteria. The values shown are the average values of four panelists who passed the olfactory test (T&T olfactometer method) in the odor judgement test and were confirmed to have normal sense of smell. The results are shown in Table 3.

(Pleasantness/unpleasantness)
-4: Extremely unpleasant -3: Very unpleasant -2: Unpleasant -1: Slightly unpleasant 0: Neither pleasant nor unpleasant +1: Slightly pleasant +2: Pleasant +3: Very pleasant +4: Extremely pleasant

(Strength)
-3: Very weak -2: Weak -1: Slightly weak 0: Just right +1: Slightly strong +2: Strong +3: Very strong

(Perception test of malodor caused by fragrances)
The panelists were asked to smell the malodorous bags prepared above in order of increasing concentration, and those that were judged to have the odor of diacetyl were marked with an O, and those that were not were marked with an X. The number of the malodorous bag that could be recognized was taken as the threshold value of the diacetyl odor.

Next, the panelists were asked to smell the sample bags containing the fragrance in the same way, in order of increasing malodor concentration. Those that were judged to have the odor of diacetyl were similarly given an ◯, and those that were not were given an ×. The number of the bag with the malodor that was recognized was taken as the threshold value of the diacetyl odor of the fragrance-mixed air. The value is the average of the four panelists. The results are shown in Table 3. If the threshold value when the fragrance was added to a similar bag was higher than the concentration (threshold) felt when smelling the malodor alone, it was determined that the fragrance contributed to deodorization (recognition of malodor). Specifically, the odor suppression function was given as ◎ when it was 2 or more higher than the threshold for the malodor alone, ◯ when it was 1 or more higher, △ when it was less than 1 (0 or more), and × when it was less than 0. The odor suppression function of the bag with only the malodor was not evaluated as it was a control.

The above results show that fragrances No. 1 to No. 20 all make the odor of diacetyl less noticeable. In particular, fragrances No. 1 to No. 17, which had different threshold values, made the odor of diacetyl significantly less noticeable. Furthermore, while strong fragrances have limited uses, tricyclodecenyl propionate, nerol, melonal, lilial, geraniol, and cyclamen aldehyde, which have low strength and high odor suppression effects, can be said to be particularly preferred diacetyl odor suppressors and are expected to be used in a variety of applications.

Claims (4)

A diacetyl odor suppressant containing one or more active ingredients selected from the group consisting of α-damascone, β-ionone, tricyclodecenyl propionate, rifarom, citral, β-damascone, nonanal, cis-6-nonenal, nerol, melonal, fenchol, lilial, anisaldehyde, dihydromyrcenol, linalool, geraniol, cyclamen aldehyde, terpineol, cis-jasmone, 3-phenyl-1-propanol, and ethyl linalool. The diacetyl odor inhibitor according to claim 1, wherein the active ingredient is one or more selected from the group consisting of α-damascone, β-ionone, tricyclodecenyl propionate, rifarom, citral, β-damascone, nonanal, cis-6-nonenal, nerol, melonal, fenchol, lilial, anisaldehyde, dihydromyrcenol, linalool, geraniol and cyclamen aldehyde. The diacetyl odor suppressant according to claim 1 or 2, wherein the active ingredient is one or more selected from the group consisting of tricyclodecenyl propionate, nerol, melonal, lilial, geraniol and cyclamen aldehyde. A method for suppressing diacetyl odor, comprising a step of contacting the diacetyl odor suppressant according to any one of claims 1 to 3 with diacetyl.