JPH10243994A - Antimicrobial composition and coating material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain products having a particularly excellent antimicrobial property, mildew-proofing property, safety, liquid preservable and stable property, etc., by including at least an amphoteric surfactant and a flavonoid deriv. into the compsn. SOLUTION: The amphoteric surfactant of a glycine type is expressed by formula I. In the formula, R is a 6 to 16C alkyl, etc., and denotes an octyl group, dodecyl group, etc. The flavonoid deriv. is the compd. of the flavonoid expressed by formula II as a skeleton. The antimicrobial compsn. is obtd. by mixing at least the amphoteric surfactant and the flavonoids deriv. The antimicrobial compsn. prepd. by mixing the amphoteric surfactant at a ratio of about 0.5 to 30 pts.wt., more particularly 1 to 20 pts.wt. per 1 pt.wt. flavonoid deriv. is more preferable. The mixing method is preferably executed by mixing the aq. soln. of the flavonoid deriv. and the aq. soln. of the amphoteric surfactant. At this time, the flavonoid deriv. is preferably added to the aq. soln. of the amphoteric surfactant previously adjusted to pH5 to 7 at 25 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a composition having antibacterial properties and a paint having antibacterial properties.

[0002]

2. Description of the Related Art Hitherto, amphoteric surfactants have antibacterial properties themselves and are therefore used as antibacterial agents. The amphoteric surfactant is, for example, dodecyl diaminoethyl glycine hydrochloride. Such an aqueous solution containing an amphoteric surfactant has not only a detergency but also a cation-active group, so it has an antibacterial (antibacterial) and bactericidal (bactericidal) properties against Escherichia coli and the like. Also have.

[0003]

However, although the amphoteric surfactant has antibacterial properties, there is a problem that its antibacterial properties and fungicide properties are not sufficient.

Accordingly, an object of the present invention is to provide an economical antibacterial composition and an antibacterial paint which are particularly excellent in antibacterial properties and are also excellent in fungicidal properties, safety, storage stability of liquids and the like. .

[0005]

The object is achieved by providing an antimicrobial composition containing at least an amphoteric surfactant and a flavonoid derivative.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, embodiments will be described to make the present invention easier to understand. The amphoteric surfactant (amphoteric surfactant) is a surfactant having both an atomic group that dissociates into an anion and an atomic group that dissociates into a cation in one molecule. As the amphoteric surfactant, an amino acid-type amphoteric surfactant, particularly a glycine-type amphoteric surfactant, is preferable because it gives a composition having excellent antibacterial properties. The glycine-type amphoteric surfactant is represented by the following chemical formula 1.

[0007]

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In the formula, R is an alkyl group having 6 to 16 carbon atoms, such as an octyl group and a dodecyl group. The above specific examples are those in which R is an octyl group (8 carbon atoms) (that is, polyoctyl polyaminoethyl glycine).

The flavonoid derivative is a compound having a flavonoid represented by the following chemical formula 2 as a skeleton. The flavonoid derivative may be a compound in which a flavonoid skeleton is substituted with a group containing a hydroxyl group, an ester bond or an ether bond.

[0010]

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Examples of the flavonoid derivative are those having a phenolic hydroxyl group, for example, those having the phenolic hydroxyl group in the 2-phenyl group of the chemical formula (2) or derivatives thereof.

[0012]

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Another example of the flavonoid derivative is a flavonoid (2-phenylchromone) represented by the formula (2) having a hydroxyl group at the 3-position, or a glycoside thereof (that is, flavonols). Natural flavonoids can be suitably used as the flavonoid derivative. For example, a natural flavonoid obtained from an extract of a seed of a citrus plant such as grapefruit can be suitably used.

The antibacterial composition of the present invention can be obtained by mixing at least an amphoteric surfactant and a flavonoid derivative. In the composition of the present invention, the amphoteric surfactant is added in an amount of about 0.5 to 30 with respect to 1 part by weight of the flavonoid derivative.
It is preferable to mix them in a ratio of 1 part by weight, especially 1 to 20 parts by weight. When the amount is less than about 0.5 part by weight, the antibacterial properties are poor, and expensive flavonoid derivatives are used in a relatively large amount, which is uneconomical. If it exceeds 30 parts by weight,
Mold resistance is reduced.

The method of mixing the flavonoid derivative with the amphoteric surfactant is not limited, but it is preferable to mix an aqueous solution of the flavonoid derivative with an aqueous solution of the amphoteric surfactant. At that time, it is preferable to add a flavonoid derivative to an aqueous solution of an amphoteric surfactant whose pH at 25 ° C. has been previously adjusted to 5 to 7. When a flavonoid derivative is added to an aqueous solution whose pH has been previously adjusted to be neutral as described above,
When the flavonoid derivative and the amphoteric surfactant are mixed, these mixtures do not gel.

The pH of the aqueous solution of the amphoteric surfactant is adjusted by adjusting the acid
This is achieved by mixing an alkali substance and an aqueous solution of an amphoteric surfactant. As the acid / alkali substance, oxycarboxylic acid is preferable, and as oxycarboxylic acid, lactic acid, malic acid, tartaric acid, citric acid and the like can be mentioned. With oxycarboxylic acids, unlike mineral acids such as hydrochloric acid, the compositions of the present invention do not have metal corrosivity.

The mixed solution of the amphoteric surfactant and the flavonoid derivative (the antibacterial composition of the present invention) may be further adjusted to neutral pH. The preferred pH range is 5-7 (25 ° C). The pH is adjusted by mixing an acid / alkali substance, preferably a nucleotide (for example, inosinic acid) with the mixture. Since nucleotides are natural products, the composition of the present invention is excellent in safety.
Further, even if the pH-adjusted composition is stored for a long period of time, it does not gel during storage. That is, the composition has excellent storage stability. Further, the composition using the nucleotide does not corrode metals and the like.

The composition of the present invention is diluted with water or the like,
For example, those diluted about 50 to 200 times are included. When the composition is diluted with water or the like and used as an antibacterial agent, if the concentration of each of the amphoteric surfactant and the flavonoid derivative is about 1 ppm or more, preferably 10 ppm or more,
The composition of the present invention exhibits antibacterial properties against Escherichia coli, Staphylococcus aureus and the like. When the composition of the present invention is used as an antibacterial agent or the like, the concentration of the amphoteric surfactant and the concentration of the flavonoid derivative differ depending on the type of bacteria, mold, etc., or the use as an antibacterial agent. However, amphoteric surfactants,
Each concentration of the flavonoid derivative is about 1-3000
ppm, preferably 10 to 3000 ppm can be suitably used as an antibacterial agent, a bactericide or a fungicide. When the amount is less than about 1 ppm, the antibacterial property and the antifungal property are inferior.

The antimicrobial composition of the present invention is a mixture of at least a surfactant and a flavonoid derivative which is a natural extract. Therefore, the antimicrobial composition of the present invention is compared with a composition containing only an amphoteric surfactant or a flavonoid derivative. It is an effective antibacterial agent for a wide range of bacteria and fungi, and is also a fungicide, fungicide and the like. Further, it has long-lasting antibacterial properties, bactericidal properties, fungicidal properties, etc., has little decrease in activity over time, and is excellent in safety. Furthermore, since the composition also has an antioxidant effect, the freshness of the food can be maintained. Therefore, hospitals, care, utensils used in food processing, equipment, etc., if the surface treatment with the composition of the present invention, fungi, mold propagation is suppressed, fungi,
The fungus is killed or the mediating pathway is interrupted. As described above, the composition of the present invention can effectively suppress cross-infections such as hospital-acquired infections and is useful for improving the sanitary environment.

Various antibacterial articles can be manufactured by using the antibacterial composition of the present invention. Examples of antibacterial articles include, but are not limited to, antibacterial fibers, antibacterial fabrics, antibacterial paper, and antibacterial materials obtained by attaching, impregnating, and applying the composition of the present invention to fibers, nonwoven fabrics, paper, metal plates, building materials, and the like. It is a painted product. If the concentration of each of the amphoteric surfactant and the flavonoid derivative in the antibacterial article is about 1 to 3000 ppm, preferably about 10 to 3000 ppm, the antibacterial article has antibacterial properties against Escherichia coli, Staphylococcus aureus, and the like. Show. One example of the use of the antimicrobial fabric is as a kitchen filter for filtering kitchen refuse such as food. The kitchen filter is manufactured by attaching the composition of the present invention to a nonwoven fabric. An example of the antibacterial fabric is an antibacterial workwear. Even when the composition of the present invention is applied to a woven fabric, the flexibility of the work clothes is not lost. In addition, the composition of the present invention can be disinfected even when it comes into direct contact with the skin or the like, and does not show toxicity to the human body. Therefore, these household goods and work clothes can be used with confidence.

The antibacterial coated article can be obtained by applying an antibacterial paint obtained by mixing the antibacterial composition of the present invention and a resin to an article to be coated such as a metal plate. The resin mixed with the antimicrobial composition of the present invention may be in the form of a water emulsion. Examples of the resin include natural resins such as natural rubber, cellulose derivatives, phenol resins, polyurethane resins, acrylic resins, silicone resins, and synthetic resins such as silicone epoxy resins.

When a fluorine-containing resin is used as the resin, a coated article having particularly excellent antibacterial properties can be obtained. The fluorine element-containing resin is a resin to which a fluorine element is chemically bonded, and is a polymer obtained by polymerizing a polymerizable monomer containing a fluorine element. Examples of the fluorine element-containing resin include an acrylic urethane resin and an acrylic melamine resin containing an element fluorine. The antibacterial paint of the present invention may further contain, if necessary, a curing agent, a coloring agent such as a dye or pigment, a filler such as an inorganic powder, another bactericide, and a fungicide.

The paint of the present invention provides a coated product which is excellent not only in antibacterial properties but also in bactericidal properties and fungicidal properties. In the coating film, the concentration of each of the amphoteric surfactant and the flavonoid derivative is about 1 to 3000 ppm, preferably about 10 ppm.
When present in an amount of up to 3000 ppm, the coating film exhibits antibacterial properties and mold resistance. For example, the paint of the present invention can be applied to the surface of a drain pan (dish) of a humidifier. Even if the drain pan coated with the coating material of the present invention is used for a long time, slimy deposits do not adhere to the surface. The paint of the present invention can be used as an antibacterial paint for in-hospital infection control by applying it to equipment used in hospitals, equipment, etc.
It is useful as an antibacterial / antifungal paint for switchboards or electric circuits.

[0024]

Hereinafter, the present invention will be described in detail. In the following test examples, all “%” and “part” mean “% by weight” and “part by weight”.
As a flavonoid derivative-containing liquid, a pale yellow transparent viscous liquid containing a fatty acid flavonoid having a flavonoid skeleton represented by Chemical Formula 2 at room temperature was prepared. The concentration of the fatty acid flavonoid in the liquid was 80%. The fatty acid flavonoids were obtained from grapefruit seed extracts.

On the other hand, as the amphoteric surfactant solution, octyl diaminoethyl glycine which is a glycine type surfactant is used.
An aqueous solution containing 30% of (C ₈ H ₁₇ NHCH ₂ CH ₂ ) ₂ N ⁺ CH ₂ COO ⁻ was prepared. A 3% aqueous solution of citric acid was added to the amphoteric surfactant solution to adjust its pH (25 ° C.) to 5.
5 was obtained.

The anti-bacterial composition of the present invention was obtained by adding the above-mentioned flavonoid derivative-containing liquid at room temperature (25 ° C.) to the amphoteric surfactant aqueous solution with stirring and stirring. The flavonoid derivative-containing liquid (1 part) and the amphoteric surfactant aqueous solution (4 parts) were mixed at a mixing ratio of 1 part. No gelation was observed during mixing. The obtained antibacterial composition was further adjusted to pH (25 ° C.) 5.5 by further adding a 3% aqueous solution of inosinic acid. The antibacterial composition was stored at room temperature for several days, but no gel component (insoluble component) was observed. That is, the storage stability of the liquid was excellent.

The antibacterial composition was impregnated in a paper-made heat-dissipating sheet by 0.2% with respect to the heat-dissipating sheet and dried to produce an antibacterial-treated sheet.

Further, 1 part of the above antibacterial composition was mixed with 99 parts of a fluorine element-containing acrylic paint (solid content: 50%) to obtain an antibacterial paint of the present invention.

This antibacterial coating was applied to the surface of a stainless steel plate and dried to obtain an antibacterial coating having an antibacterial coating. In addition, the thickness of the coating film was 20μ.

An antibacterial test was carried out on the antibacterial treated sheet and the antibacterial coated product manufactured as described above as follows. The antibacterial activity test was performed using an appropriately sized sample (5 per side).
cm × 5 cm) as a test piece, 1 ml of a bacterial solution of Escherichia coli, Staphylococcus aureus, Vibrio parahaemolyticus, Aspergillus niger or blue mold was added dropwise, and stored at 25 ° C .;
The viable cell count after 8 hours was measured. In the test method, test conditions such as a test bacterium (bacteria and mold), a method for preparing a bacterial solution, and a method for measuring the number of viable bacteria were as follows.

Bacteria: Escherichia coli
IFO 3301 (E. coli), Staphylococ
cus aureus IFO 12732 (Staphylococcus aureus), VIbrio parahaemolyti
cus RIMD 2210100 (Vibrio parahaemolyticus); Mold: Aspergillus niger IFO
4407 (Black Aspergillus), Penicillium c
itrinum IFO 7784 (blue mold)

Preparation of bacterial solution: The bacteria were cultured in a normal bouillon medium (manufactured by Eiken Chemical Co., Ltd.) at 35 ° C. with shaking overnight.
It was diluted 0000-fold to obtain a bacterial solution. However, Vibrio parahaemolyticus was cultured and diluted with a normal broth medium supplemented with 3% sodium chloride and a sterilized phosphate buffer to obtain a bacterial solution. Mold is potato dextrose agar (Eiken Chemical Co., Ltd.)
After culturing at 25 ° C. for 7 days, the conidia of the test bacteria formed were suspended in a sterilized 0.05% polysorbate 80 solution.
A bacterial solution was used.

A method for measuring the number of viable bacteria; test pieces after storage, bacteria for SCDLP liquid medium (manufactured by Nippon Pharmaceutical Co., Ltd.),
Washed out with a P liquid medium (Nippon Pharmaceutical Co., Ltd.). For the viable cell count of the washed liquid, the bacteria were pour-plate-cultured (35 ° C. for 2 days) using a standard agar medium (manufactured by Eiken Chemical Co., Ltd.), and the mold was pour-poured using potato dextrose agar medium. Measured by the plate culture method (cultured at 25 ° C for 7 days),
It was converted per sheet.

Tables 1 to 3 show the results of measuring the viable cell count of the above antibacterial treated sheet and antibacterial coated product under the above test conditions. Table 1 shows the measurement results for the antibacterial treatment sheet, and Tables 2 and 3 show the measurement results for the antibacterial coating product. The number of viable bacteria in Tables 1 to 3 is a value per test piece (size of 5 cm × 5 cm), and “<10” indicates that no bacteria were detected by the method for counting the number of bacteria used in this test. It shows that.
Also, the number of viable bacteria at the start, the number of viable bacteria dropped was measured,
This is a value converted per test piece. In addition, the untreated sheet in Table 2 is a raw material sheet used for manufacturing the antibacterial treatment sheet, and is a sheet which is not impregnated with the antibacterial composition of the present invention. The normal coated products in Tables 2 and 3 are
A fluorine-containing acrylic paint was applied to the surface of the stainless steel plate used for the production of the antibacterial paint and dried, and the paint film did not contain the antibacterial composition of the present invention.

[0035]

[Table 1]

[0036]

[Table 2]

[0037]

[Table 3]

From Table 1, it can be seen that the antibacterial treated sheet has an antibacterial property against Escherichia coli, Staphylococcus aureus and blue mold as compared with the untreated sheet. That is, the composition of the present invention inhibited the growth of bacteria, mold, and the like.

From Tables 2 and 3, it can be seen that the antibacterial coated product is compared with the normal coated product, Escherichia coli, Staphylococcus aureus, Vibrio parahaemolyticus,
It can be seen that it had antibacterial properties against Aspergillus niger and blue mold. That is, the coating film formed from the paint of the present invention inhibited the growth of bacteria such as bacteria and mold.

[0040]

As described above, the compositions and coatings of the present invention have excellent antibacterial properties, as well as excellent bactericidal properties, antioxidant properties, safety, storage stability of liquids, economic efficiency and the like.

Claims (4)

[Claims] An antibacterial composition comprising at least an amphoteric surfactant and a flavonoid derivative. 2. The antibacterial composition according to claim 1, wherein the amphoteric surfactant is of the glycine type. 3. An antibacterial paint containing at least an amphoteric surfactant, a flavonoid derivative and a resin. 4. The antibacterial paint according to claim 3, wherein the resin contains elemental fluorine.