WO2007132710A1

WO2007132710A1 - Bactericidal/preservative agent

Info

Publication number: WO2007132710A1
Application number: PCT/JP2007/059590
Authority: WO
Inventors: Makoto Takeuchi; Noriko Mori; Hiromi Tatsukawa
Original assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority date: 2006-05-11
Filing date: 2007-05-09
Publication date: 2007-11-22
Also published as: JPWO2007132710A1; JP5145214B2; TWI427071B; TW200812988A

Abstract

The object is to provide a bactericidal/preservative agent whose bactericidal/preservative ingredient is hardly degraded even when exposed to an environmental light such as an artificial light and natural light, and also provide use of the bactericidal/preservative agent. Provided is a bactericidal/preservative agent comprising a specific cyanin dye as a bactericidal/preservative ingredient and rutin or a sugar derivative thereof as an ingredient for improving the light resistance of the cyanin dye. Also provided is an agent for external application to the skin, which comprises the bactericidal/preservative agent.

Description

Specification

Sterilization, preservative

Technical field

[0001] The present invention relates to a novel disinfectant / preservative and its use.

Background art

[0002] As is well known, preparations for external use on skin such as cosmetics are required to be prepared so as not to contain microorganisms as much as possible. However, no matter how carefully it is prepared, preservatives are usually used because it is impossible to prevent microbial contamination and growth during use. In addition, depending on the dosage form of the external preparation for skin, it may not be physically sterilized during the production, and in such a case, a bactericidal agent will be used.

[0003] Raw materials applied to the external preparation for skin as a bactericidal agent or preservative include, for example, organic acids such as benzoic acid and dehydroacetic acid, alcohols such as phenylethanol and phenoxyisopropyl alcohol, hydroxybenzoic acid There are phenols such as esters and chlortaresol, ammonium salts such as benzalkonium chloride and benzethonium chloride, and chlorhexidine, propylene glycol, photosensitizer 101 and photosensitizer 201. Photosensitive Element 101 and Photosensitive Element 201 exhibit remarkable sterilization and antiseptic properties at low concentrations, so that sterilization against acne bacteria is possible in addition to general cosmetics such as basic cosmetics, finished cosmetics, and hair cosmetics. For example, it is widely used as an active ingredient in quasi-drugs such as acne agents that use growth-inhibiting ability. Are (see, for example, JP-A-2 2 15706 Publication, Hei 10- 109923 JP, the JP 2002- 212009 publication).

However, force cyanine dyes such as Photosensitive Element 101 and Photosensitive Element 201 have low light resistance compared to the above-mentioned other sterilizing / preserving agents due to the chemical structure. When exposed to ambient light such as natural light or artificial light in a dissolved state, it decomposes in a short time.

Disclosure of the invention

[0005] In view of such circumstances, the problem to be solved by the present invention is to provide a sterilizing / preservative that does not easily decompose the sterilizing / preserving component even when exposed to ambient light such as natural light or artificial light. It is in [0006] Further, the problem to be solved by the present invention is to provide the use of such a bactericidal / preservative, in particular, a skin external preparation such as cosmetics.

[0007] The present invention provides a bactericidal / preservative comprising a cyanine dye represented by the general formula 1 or 2 as a bactericidal / preservative component and rutin or a sugar derivative thereof as a component for enhancing the light resistance of the cyanine dye. The problem is solved by providing an agent.

[0008] General Formula 1:

[Chemical 3]

[0009] General Formula 2:

[Chemical 4]

(In the general formulas l and 2, R to R are the same or different aliphatic hydrocarbon groups.

I 5

These aliphatic hydrocarbon groups may have a substituent. X—or X—

I 3 represents an appropriate anion. )

[OOll] Furthermore, the present invention solves the above-mentioned problems by providing a skin external preparation containing such a bactericidal / preservative.

[0012] The sterilizing 'preservative according to the present invention is sterilized even when exposed to ambient light such as natural light and artificial light.

'Because the cyanine dyes represented by general formulas I and 2, which are antiseptic components, are difficult to decompose, From the viewpoint of photogenicity, there is an actual benefit that can be effectively applied without worrying about the degradation of cyanine dyes even in applications where it has been hesitant to apply such cyanine dyes.

[0013] In addition, the topical skin preparations such as cosmetics using such antibacterial / preservatives can be used for growth of microorganisms mixed during preparation or use even in the form of solutions, emulsions, gels, and the like. In addition, quasi-drugs containing the cyanine dyes represented by the general formula 1 or 2 as an active ingredient have the advantage that the bactericidal ability and the like are not easily reduced for a long time.

BEST MODE FOR CARRYING OUT THE INVENTION

[0014] As described above, the present invention comprises a cyanine dye represented by the general formula 1 or 2 as a sterilizing / preserving component, and rutin or a sugar derivative thereof as a component that enhances the light resistance of the cyanine dye. Containing sterilization / preservative and its use.

[0015] General Formula 1:

[Chemical 5]

[0016] General Formula 2:

[Chemical 6]

In the general formulas 1 and 2, R to R are the same or different aliphatic hydrocarbon groups.

1 5

These aliphatic hydrocarbon groups may have a substituent. R or R

1 5 As the aliphatic hydrocarbon group, a linear or branched group having up to 20 carbon atoms, usually having up to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an isopropenyl group, 1 propenyl group, 2-propenyl group, 2-propynyl group, butyl group, isobutyl group, see butyl group, tert_butyl group, 2-butyr group, 1,3_butadienyl group, pentyl group, isopentyl Group, neopentyl group, tert_pentyl group, 1-methylpentyl group, 2-methylpentyl group, hexyl group, 2_pentenyl group, 2_pentene_4_ynyl group, isohexyl group, 5_methylhexyl Group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecinole group, etc. Among them, the number of carbon atoms is 5 to 9 in terms of solubility in solvents and affinity for microbial cells. No In particular, those having 7 carbon atoms are most preferable.

[0018] In the aliphatic hydrocarbon group, one or more of its hydrogen atoms are in a hydroxy group or within the range not departing from the object of the present invention. Alternatively, for example, methoxy group, trifluoromethoxy group, ethoxy group, propoxy Group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert butoxy group, pentyloxy group, phenoxy group, benzyloxy group and the like, which may be substituted. In addition, as in the cyanine dyes represented by the general formulas 1 and 2, those having two or more similar cyclic groups in the molecule, and those having a cyclic group strength S each having an aliphatic hydrocarbon group In terms of ease of preparation, their aliphatic hydrocarbon groups are conveniently the same as each other.

In the general formulas 1 and 2, X— or X— represents an appropriate anion, and each anion

13

For example, inorganic ions such as fluorine ion, chlorine ion, bromine ion, iodine ion, perchlorate ion, perbromate ion, periodate ion, nitrate ion, sulfate ion, phosphate ion, borate ion, etc. Ion, acetate ion, trifluoroacetate ion, trichloroacetate ion, benzoate ion, hydroxybenzoate ion, sulfonate ion, p-toluenesulfonate ion, ethyl sulfate ion, aspartate ion, orthoate ion, nicotinate ion Among them, iodine ions are particularly preferable because they have sterilizing and antiseptic properties.

[0020] Specific examples of such cyanine dyes include those represented by chemical formulas 1 to 10. None of these cause substantial damage to the human body. Prominent bactericidal activity against microorganisms to be excluded in topical skin preparations, for example, microorganisms of the genus Alpergillus, Escherichia, Candida, Corynebacterium, Syudomonas, Staphylococcus, and Noctilus Demonstrate. Among the cyanine dyes represented by the chemical formulas 1 to 10, those represented by the chemical formulas 2 and 7 have particularly high bactericidal and antiseptic properties and are moderately soluble in various solvents commonly used for external preparations for skin. It is particularly preferable since it has the properties. The cyanine dyes represented by Chemical Formulas 2 and 7 have specifications that are compatible with topical skin preparations such as cosmetics and quasi-drugs, respectively, as “Pionin” (Photosensitive Element 201) and “Platonin” (Photosensitive Element). No. 101) is sold under the product name.

[0021] Chemical Formula 1:

[Chemical 7]

H ₃ C (H ₂ C) 2 H ₂ C CH ₂ (CH _Z ) _Z CH ₃

[0022] Chemical Formula 2:

[Chemical 8]

H ₃

H ₃

[0023] Formula 3:

[Chemical 9]

H

H ₃

[0024] Chemical Formula 4: [Chemical 10]

H ₃ C (H ₂ C) ioH ₂ C CH _z (CH ₂ ) ioCH ₃

[0025] Chemical Formula 5:

[Chemical 11]

[0026] Chemical formula 6

[Chemical 12]

[0027] Chemical Formula 7:

[Chemical 13]

[0028] Chemical Formula 8:

[Chemical 14]

[0029] Chemical Formula 9:

[Chemical 15]

H ₃

H ₃

[0030] Formula 10:

[Chemical 16]

On the other hand, rutin as used in the present invention is a kind of flavonol glycoside represented by the chemical formula 11.

(Taercetin _3-rutinoside), for example, natural ones derived from plants such as laceae, legumes and citrus can be easily obtained.

[0032] Chemical Formula 11:

[Chemical 17]

[0033] The rutin sugar derivative referred to in the present invention means one in which a sugar residue is bonded to one or more of the hydroxy groups in the chemical formula 11, and in particular, the same patent application in terms of availability. A human dalcosyl group or a group bonded to the hydroxy group bonded to the 4-position carbon of the gnolecose residue in the rutinose residue of the chemical formula 11 described in JP-A-3-27293 and JP-A-3-115292. Preferred are monoglycosyl rutin, hyal-maltosyl rutin, hyal-maltotriosyl rutin, etc., to which a single glycosyl group is bonded. Although rutin is known to have a high purity product with pale yellow needles, In this invention, not only such a high-purity product, but also a relatively low-purity product of natural origin prepared from a plant of the family Taceae, Legumes, Citrus, Synthetic products or semi-synthetic products, and also specific to rutin sugar derivatives and preparation methods such as those described above, which are obtained by enzymatic treatment of these in the presence of a partially degraded starch, such as unreacted rutin and starch. It may be a composition in which impurities such as partially decomposed products are naturally integrated.

The sterilizing “preservative” according to the present invention is a sterilizing “preservative” containing one or more cyanine dyes as described above, and rutin and Z or a sugar derivative thereof. The content of rutin and / or its sugar derivative in such a sterilizing / preservative depends on the type and use of the individual skin external preparations to which the sterilizing 'preservative is applied, but is generally expressed in terms of solids as a general formula 1 or More than 0.01 parts by weight, preferably 0.1 to 1,000 parts by weight, more preferably 1 to 500 parts by weight, per 1 part by weight of the cyanine dye represented by 2. When the amount of rutin and / or a sugar derivative thereof is less than 0.01 parts by mass relative to 1 part by mass of the cyanine dye represented by the general formula 1 or 2, the light resistance of the cyanine dye cannot be substantially increased, and 1 Even if the amount exceeds 000 parts by mass, the effect of increasing light resistance has peaked, and the yellow color inherent to rutin or its sugar derivatives has become conspicuous, and this may impair commercial value depending on the application. Usually, it is adjusted in the range of 0.01 to 1,000 parts by mass.

[0035] The sterilizing / preserving agent of the present invention exhibits a remarkable sterilizing / preserving ability in any of liquid, solid and semi-solid. In particular, when used in a state dissolved in a solvent, even if it is exposed to ambient light such as natural light or artificial light, its remarkable sterilizing / preserving ability is hardly attenuated. The solvent is not particularly limited as long as the cyanine dye represented by the general formula 1 or 2 and rutin or a sugar derivative thereof are substantially dissolved, and is commonly used in skin external preparations such as cosmetics. Dermatologically acceptable, for example, water, ethanol, propanol monoole, isopropanol, glycerin, ethylene glycolanol, propylene glycolanol, butylene glycol, 1,2_pentanediol, 1,2-hexane Alcohols such as diol, 1,2-heptanediol, 1,2-octanediol and low molecular weight polyols are listed, and these are used in combination as necessary. Of these, 1, 3—Buchi Butylene glycol, such as lenglycol, and 1,2-alkylene diol, such as 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, themselves Has the ability to sterilize, and the latter 1,2-alkanediol is particularly preferable since it provides a high sterilizing / preserving effect synergistically with the cyanine dye of the present invention. When the cyanine dye and noretin or a sugar derivative thereof are dissolved in a solvent, as necessary, for example, polyoxyethylene alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene myristyl ether, polyoxyethylene can be used as a solubilizer. Add appropriate amount of surfactants such as ethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene oleyl cetyl ether, polyoxyethylene beenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene noyl phenyl ether , Heat and stir. Although the concentration of cyanine dye in the solution-like disinfectant 'preservative according to the present invention should be set as appropriate, when it is made into a product as a disinfectant / preservative, up to 20% by weight of cyanine dye is usually 0.01. Add or subtract 10% by mass.

The use of the sterilizing / preservative according to the present invention will be described. The sterilizing / preservative according to the present invention has a remarkable sterilizing / preserving action without causing substantial damage to the human body. Because it is hard to be attenuated even in an environment exposed to ambient light, such as natural light and artificial light, and sterilized 'preservative ability', sterilization 'preservatives are required, especially in cosmetics and pharmaceutical departments It is extremely useful in the field of external preparations for skin including external products.

[0037] Skin external preparations to which the sterilizing / preservative according to the present invention can be applied include, for example, face wash sarcophagus, face wash cream, face wash foam, cleansing cream, cleansing jewel, coronole cream, lotion, massage cream, milky lotion, beauty Basic and whitening cosmetics such as liquids, moisturizing creams, vanishing creams, hyzenic creams, packs, powder foundations, cake foundations, amphibious foundations, stick foundations, cream foundations, liquid foundations, white powders, makeup bases, lipsticks, eye shadows Finishing cosmetics such as eyeliner, mascara, hairbrow, scarlet, nail enamel, body cream, body lotion, massage cream, body powder, etc. Cosmetics, shampoos, hair rinses, hair treatments, hair conditioners Hair, hair pack, hair liquid, hair tonic, permanent 'wave agent, hair dye, depigmenting agent, hair restorer, hair nourishing cosmetics, sarcophagus, body shampoo, hand soap, deodorant, bath preparation, repellent , Hair remover, hair remover, shaving cream, shaving lotion, body care cosmetics such as shaving foam, perfume, perfume oil, perfume Frederance cosmetics such as sarcophagus, as well as toothpaste, hand cream, acne agent, etc. In general, external preparations and other external preparations for skin are mentioned, and the disinfectant / preservative according to the present invention disinfects microorganisms in such external preparations for skin and effectively suppresses the growth of microorganisms.

Such an external preparation for skin is used together with the bactericidal / preservative according to the present invention, for example, water, acetone, toluene, ethyl methyl ketone, isobutyl methyl ketone, cyclohexane, butanol, isoamyl acetate, ethyl acetate. , Solvents such as butyl acetate, avocado oil, almond oil, olive oil, cacao oil, sesame oil, safflower oil, soybean oil, camellia oil, versic oil, castor oil, mink oil, cottonseed oil, molasses, palm oil, egg yolk oil Fats and oils such as sperm oil, sperm whale oil, beeswax, whale wax, lanolin, jojoba oil, carnauba wax, canderia wax, montan wax, liquid paraffin, petrolatum, paraffin, ozokerite, cecilene, microcrystalline wax, Polyethylene powder, screen, scalar , Hydrocarbons such as pristane, fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, 12-hydroxystearic acid, tonole oil, lanolin fatty acid, ethanol, isopropanol, lauryl alcohol, cetanol Nore, stearyl alcohol, isostearyl alcohol, oleyl alcohol, lanolin alcohol, cholesterol, phytosterol, 2-hexyl decanol, 2-octade strength, ethylene oxide, ethylene glycol, diethylene glycol, triethylene glycolate, ethylene glycol Ethino oleore, ethylene glycol monobutino rea tenole, diethylene glycol eno mono methino eno enore, diethylene glycol eno mono eno Itel, polyethylene glycol, propylene oxide, propylene glycol, polypropylene glycolol, glycerin, butinoleanolecanole, pentaerythritolol, sonolebitolone, manolitol, glucose, sucrose, manoletos, trehalose and other alcohols and sugars, myristic acid Isopropyl, otatildodecyl myristate, myristino myristate, palmi Isopropyl tinate, butyl stearate, hexyl laurate, oleyl oleate, decyl oleate, hexyl decyl dimethyloctanoate, cetyl lactate, myristyl lactate, jetyl phthalate, dibutyl phthalate, lanolin acetate, ethylene glycol monostearate , Estenoles such as propylene glycol monostearate and propylene glycol dioleate, gum arabic, benzoin gum, danmanole gum, guayata fat, ainoleland moss, cara gum, tragacanth gum, kilob gum, quince seed, agar, casein, dextrin, gelatin, pectin , Sodium pectate, starch, dextran, pullulan, sodium anoleate, methinoresenorelose, ethinoresenorelose, canoleboxymethylenole Senole mouthpiece, hydroxyethinoresenololose, hydroxypropinoresenorelose, nitrosenololose, crystalline cellulose, polybulualcohol, polybulumethyl ether, polybulupyrrolidone, sodium polyacrylate, carboxyvinyl polymer, polyethylene Polymers such as imine, fatty acid, carboxylic acid, carboxylate, sulfonic acid, sulfonate, sulfate ester, sulfate ester salt, phosphate ester salt, phosphate ester salt, amine salt , Quaternary ammonium salt, betaine, ether, ether ester, ester, block polymer, nitrogen-containing cation, anion, amphoteric or nonionic surfactant, tocopherol, sezamol, gossypol, phosphorus Lipids, dibutylhydroxytoluene, Antioxidants such as tilhydroxyanisole and propyl gallate, p-amino benzoate, phenyl salicylate, cinoxalate, guaizulene, 2- (2-hydroxy-5-methylphenyl) benzotriazole, oxybenzone, etc. UV absorber, lactic acid, tartaric acid, succinic acid, citrate, boric acid, allantoin, allantoin hydroxyaluminum, zinc chloride, calamine, zinc sulfate, zinc p-phenol sulfonate, potassium aluminum sulfate, resorcinol, resorcinol, ferric chloride , Edeto disodium, sodium Tae phosphate, sodium polyphosphate, sequestering agents, such as sodium metaphosphate, chondroitin sodium sulfate, 1, ₃ - butylene glycol, sodium lactate, maltitol, humectants such as xylitol, In addition, amino acids, vitamins, hormones, fragrances, colorants, antifungal agents, antibiotics, antiperspirants, deodorants, skin bleaches, organic bases, aerosol propellants that are widely used in cosmetics It can be prepared by appropriately blending organic chemicals, inorganic chemicals, insect repellents, wound healing agents, antihistamines and the like. [0039] The amount of the bactericidal / preservative of this invention in such a topical skin preparation depends on the intended use of the topical skin preparation, but in the case of cosmetics, the concentration of cyanine pigment is 0.002% by mass, In the case of quasi-drugs, the dosage is adjusted up to 0.005% by mass. The sterilizing and preservative referred to in this invention is not limited to an independent form in which the cyanine dye represented by the general formula 1 or 2 and rutin or a sugar derivative thereof are mixed in advance. In addition to this, for example, a form of skin external preparation in which cyanine pigment and rutin or its sugar derivative are individually added to an application target such as an external preparation for skin, and both are formulated so as to have the desired effect there. Is also included. In addition, the sterilizing / preserving agent according to the present invention is a sterilizing / preserving component within the range not departing from the object of the present invention, as well as other cyanine dyes represented by the general formulas 1 and 2, and other commonly used in the field. Disinfection 'Preservatives, for example, organic acids such as benzoic acid and dehydroacetic acid, alcohols such as phenylethanol, phenoxyisopropyl pill alcohol, phenols such as hydroxybenzoic acid ester and chronolecresol, benzalkonium chloride, benzethonium chloride Ammonium salts such as chlorohexidine, propylene glycol, etc., or a combination of one or more of them.

Next, the light resistance of the sterilizing / preserving agent according to the present invention will be described based on experimental examples.

For 1,2-pentanediol / water mixture containing cetyl alcohol as a solubilizing agent, according to the formulation shown in Table 1, Photosensitizer 101, which is a cyanine dye represented by Chemical Formula 7, or Chemical Formula 2 Test solution 1 to 10 containing or not containing noretine, α-darcosylrutin, hesperidin or α-darcosyl hesperidin together with any of photosensitizer 201, which is a cyanine dye represented by Each was prepared. Next, install a fluorescent lamp (rated power 15 W, wavelength 380 to 700 nm) so that the light intensity on the surface of the quartz tube is 2.7 mW / cm ² at a wavelength of 413 nm. The test solution was sampled over time, and artificial light from a fluorescent lamp was irradiated for 40 hours. Incidentally, the characteristic yellow color becomes conspicuous in solutions of rutin, hesperidin and their sugar derivatives when the concentration force exceeds 1% by mass. [0042] Using a commercially available column for reversed-phase high-performance liquid chromatography (trade name “Inertsil 〇DS-3V”) for the sampled test solution, methanol / water mixture (volume ratio 85:15) The remaining cyanine dye was quantified by applying high performance liquid chromatography using as an eluent. Then, the peak area of the cyanine dye in the chromatogram obtained immediately before irradiation with artificial light and the peak area of the cyanine dye in the chromatogram obtained immediately after irradiation with artificial light for 20 or 40 hours were obtained. By substituting for 1, the cyanine dye residual ratio (%) was calculated. The results are shown in Table 2.

[0043] [Table 1]

Elemental survival rate (¾)

A peak manuscript of shear dye in a 07h gram obtained immediately after a certain period of time

XI 00 Shear / dye peak area in the matogram obtained just before the start of irradiation

[0045] [Table 2]

[0046] As can be seen from the results in Table 2, test solutions 1, 2, 6 and 7 combined with either rutin or α-darcosylrutin showed no errors due to analysis even when irradiated with artificial light for 40 hours. Within the range, the cyanine dye was hardly decomposed. In contrast, the control test solutions 5 and 10 containing no rutin or a sugar derivative thereof were similarly irradiated with light, and the amount of cyanine dye was reduced to less than one-fourth of the initial value after 20 hours. After 40 hours, the degradation of cyanine dye progressed beyond detection. Control solutions 3, 4, 8, and 9 to which hesperidin and sarcosine hesperidin were added were able to detect very little cyanine dye after 40 hours, but increased the light resistance of cyanine dye. From the viewpoint, both were far from the test solution containing rutin and hyaldarcosilrutin.

[0047] As described above, rutin and hesperidin show clearly different behaviors regarding the light resistance of Photosensitive Element 201 and Photosensitive Element 101, which are representative cyanine dyes represented by the general formulas 1 and 2. It was. As is well known, rutin and hesperidin are both analogs having a benzopyran skeleton and a lutinose residue bonded to the benzopyran skeleton. is there. Nevertheless, it was a surprising fact that they behave so differently.

[0048] Based on these experimental facts, the concentrations of rutin and its sugar derivatives α-darcosylrutin, unimaltosylrutin and unimaltotriosylrutin were set to 0.001. When the test was performed in the range of mass% in the same manner as described above, when 40 hours had passed, 70% or more of the cyanine dye remained without being decomposed. Furthermore, instead of Photosensitive Element 201 and Photosensitive Element 101, cyanine dyes and rutin represented by Chemical Formula 1, Chemical Formulas 3 to 6 and Chemical Formulas 8 to 10, Hirudarukosylrutin, Hiichi Martosyl Rutin and Himaltotriosyl When tested in the same manner in the range of 0.001% in the range of 0.1% by mass for the combination with rutin, in both cases, the light resistance was remarkably increased and decomposed by the coexistence of rutin or one darcosylrutin. It turned out to be difficult. In addition, although experimental data are not shown, the bactericidal / preservative ability of cyanine dyes represented by chemical formulas 1 to 10 did not decrease even in the presence of rutin or its sugar derivative.

Hereinafter, embodiments of the present invention will be described based on examples.

Example 1

[0050] <Bactericidal 'preservative>

Polyoxyethylene cetyl ether (ΡΟΕ20) was added as a solubilizer to an appropriate amount of 1,2-pentanediol to a concentration of 10% by mass, and Photosensitizer 201 (produced by Hayashibara Biochemical Research Institute, The product name “Pionin”) and Hi-Dalcocilrutin (sold by Hayashibara Biochemical Laboratories Co., Ltd., trade name “Hi-G-Rutin”) are dissolved to a concentration of 1 and 3% by mass, respectively. The sterilization-like preservative was obtained.

[0051] a—Gnolecosyl Noretin has a remarkable anti-oxidant ability, and even if it is exposed to ambient light such as natural light and artificial light, the bactericidal / preservative ability of this example is difficult to decrease. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.

Example 2

[0052] <Bactericidal 'preservative>

A solution-like disinfectant / preservative according to the present invention was obtained in the same manner as in Example 1 except that 1,3-butylene glycol was used in place of 1,2-pentanediol. [0053] a—Gnolecosyl Noretin has a remarkable antioxidative ability, and even if it is exposed to ambient light such as natural light and artificial light, the bactericidal / preservative of this example is difficult to decrease. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.

Example 3

[0054] <Bactericidal 'preservative>

Example except that high purity rutin (manufactured by Tokiwa Plant Chemical Laboratory Co., Ltd., purity of 95% or more) was blended to a concentration of 1% by mass instead of a-gnolecosyl noretin

In the same manner as in 1, a solution-like disinfectant / preservative according to the present invention was obtained.

[0055] Sterilization and antiseptics of this example, which have remarkable antioxidant ability by rutin and are not easily reduced even when exposed to ambient light such as natural light and artificial light. It is extremely useful for topical skin preparations.

Example 4

[0056] <Bactericidal 'preservative>

In place of Photosensitive Element 201, Photosensitive Element 101 (trade name “Platonin”, manufactured by Hayashibara Biochemical Laboratories, Inc.) is blended to a concentration of 0.04% by mass, and the concentration of Hirudarukosyl rutin is 20 A solution-like sterilizing / preserving agent according to the present invention was obtained in the same manner as in Example 1 except that the mass% was changed.

[0057] a—Gnolecosyl Noretin has a remarkable anti-oxidant ability, and even if exposed to ambient light such as natural light and artificial light, the bactericidal / preservative of this example is unlikely to deteriorate. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.

Example 5

[0058] <Lotion>

For the basic formula of the following lotion, the disinfectant 'preservative obtained by the method of Example 1 was blended to a concentration of 0.005% by mass in accordance with a conventional method. Got water.

[0059] Blending ingredients Blending quantity

Glycerin 2.0 parts by mass

Propylene glycol 6.0 parts by mass Dipropylene glycol 2.0 parts by mass

Polyoxyethylene polypropylene glycol 1.0 parts by mass

Polyoxyethylene sorbitan mono

Oleic acid ester (20EO) 2.0 parts by mass

Ethanor 15.0 parts by mass

Fragrance 0.1 parts by mass

Purified water 71.9 parts by mass

[0060] The skin lotion of the present example, which has excellent skin cleansing power and does not irritate the skin, hardly grows microorganisms even when used for a long period of time.

Example 6

[0061] <Morient cream>

According to the basic formula of emollient cream shown below, this invention was formulated by blending the disinfectant / preservative obtained by the method of Example 2 to a concentration of 0.008% by mass according to a conventional method. The emollient cream was obtained.

[0062] Blending ingredients Blending quantity

2.0 parts by mass

Stearyl Arco 7.0 parts by mass

Reduced lanolin 2.0 parts by mass

5.0 parts by mass

Otachido de canal 6.0 parts by weight

Polio:-Tell (25EO) 3.0 parts by mass

New oil type 2.0 parts by mass

Fragrance 0.3 parts by mass

Cole 5.0 parts by mass

Purified water 67.7 parts by mass

[0063] The emollient cream of this example, which is excellent in moisture retention and spreadability of the skin and does not irritate the skin, hardly grows microorganisms even when used for a long period of time.

Example 7 [0064] Agent>

The present invention was formulated by blending the disinfectant preservative obtained by the method of Example 3 to a concentration of 0.004% by mass in accordance with a conventional method with the basic formula of the following peel-off type pack agent. A pack agent was obtained.

[0065] Ingredients

Polybur alcohol 15.0 parts by mass

Sodium carboxymethylcellulose 5.0 parts by mass

Propylene glycolate 3.0 parts by mass

Ethanore 10.0 parts by mass

Fragrance 0.5 parts by mass

66.5 parts by mass of purified water

[0066] The pack of this example, which has excellent skin cleansing power and moisturizes the skin, hardly grows microorganisms even when stored for a long period of time.

Example 8

[0067]

According to the basic formula of the following emulsion foundation, the disinfectant obtained by the method of Example 1 was blended in a concentration of 0.004% by mass according to a conventional method. -I got Chillon.

[0068] Compounding ingredients

'11 2.4 parts by mass

—Nore 2.0 parts by mass

—Nore 0.2 parts by mass

Liquid lanolin 2.0 parts by mass

Liquid paraffin 3.0 parts by mass

Isopropyl myristate 8.5 parts by weight

Propyl paraoxybenzoate

Purified water 64.1 parts by mass

Sodium carboxycellulose 0.2 parts by mass 0.5 parts by mass

J CALL 4.0 parts by mass

Triethanolamine

Methyl paraoxybenzoate

Titanium oxide 8.0 parts by mass

Talc 4.0 parts by mass

[0069] The foundation of this example, which has excellent spreadability and adhesion to the skin and does not irritate the skin, is difficult for microorganisms to grow even when used over a long period of time.

Example 9

[0070] <Shampoo>

The shampoo according to the present invention is obtained by blending the disinfectant / preservative obtained by the method of Example 4 to a concentration of 0.007% by mass with the basic formulation of the transparent shampoo shown below according to a conventional method. It was.

[0071] Ingredients

Sodium alkyl ether sulfate 16.0 parts by mass

Lauric acid diethanolamide 4.0 parts by mass

Propylene glycolate 2. 0 parts by mass

78.0 parts by mass of purified water

[0072] The transparent shampoo of this example, which has excellent detergency and does not irritate the skin, hardly grows microorganisms even when used for a long time.

Example 10

[0073] <Acne agent>

For the basic formula of the acne agent shown below, the same α-darcosyl rutin as used in Example 1 was blended to a concentration of 0.0015% by mass according to a conventional method. An agent was obtained.

[0074] Blending ingredients Blending quantity

Dipotassium glycyrrhizinate 0.1 parts by mass

Cyanine dye represented by chemical formula 2 0.005 parts by mass Concentrated glycerin 0.5 parts by mass

Polyoxyethylene cetyl ether (POE20) 0.2 parts by mass

3-Butyleneglycolanol 5.0 parts by mass

Ethanore 5.0 parts by mass

89.2 parts by weight

[0075] The acne agent of this example, which effectively prevents acne and significantly improves and alleviates various symptoms associated with acne, exhibits a stable pharmacological action over a long period of time.

Industrial applicability

[0076] The disinfectant / preservative according to the present invention is extremely useful in external preparations for skin such as cosmetics and quasi-drugs, especially in external preparations exposed to ambient light such as natural light and artificial light during preparation or use. . In fields other than the topical skin preparation, it can be advantageously applied to a wide variety of articles requiring a disinfectant.

Claims

A sterilizing / preservative comprising a cyanine dye represented by the general formula 1 or 2 as a sterilizing / preservative component and rutin or a sugar derivative thereof as a component for enhancing the light resistance of the cyanine dye. General formula 1:

[Chemical 1]

General formula 2:

[Chemical 2]

I 5

And those aliphatic hydrocarbon groups may have a substituent. X— or X— is appropriate

I 3 represents a suitable anion. )

[2] a cyanine dye represented by the general formula I or 2 as a bactericidal and antiseptic component, and rutin or a sugar derivative thereof as a component that enhances the light resistance of the cyanine dye, The disinfectant / preservative according to claim I dissolved in a solvent.

[3] The sterilizing / preservative according to any one of claims 1 and 2, wherein 0.01 parts by mass or more of rutin or a sugar derivative thereof is contained per 1 part by mass of the cyanine dye. 4. The disinfectant / preservative according to claim 2 or 3, wherein the solvent is alcohol or low molecular weight polyol.

A topical skin preparation comprising the disinfectant / preservative according to any one of claims 1 and 4.