JPH1192306A - Antimicrobial agent for fiber and antimicrobial and deodorizing-processed textile product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject antimicrobial agent causing no irritation to the skin by using a diglycerol monofatty acid ester containing a mono-fatty acid ester of a specific purity as an active ingredient. SOLUTION: This antimicrobial agent contain a diglycerol monofatty acid (as a 8-18C fatty acid) having more than 50 wt.% purity of the monofatty acid ester as an active ingredient. In general, the diglycerol fatty acid ester is obtained by heating the mixture of diglycerol with fatty acid at 180-240 deg.C in the presence of or the absence of a catalyst and the reaction mixture comprises unreacting diglycerol, diglycerol monofatty acid ester, difatty acid ester, trifatty acid ester and tetrafatty acid ester. The objective diglycerol monofatty acid ester containing >=50 wt.% of diglycerol monofatty acid is obtained by removing the unreacting diglycerol from the reaction mixture or by the solvent fractionation, molecular distillation and other processes.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an antibacterial agent for fibers containing diglycerin monofatty acid ester having an excellent antibacterial action as an active ingredient, and an antibacterial and deodorant fiber product provided with the antibacterial agent.

[0002]

2. Description of the Related Art Clothes, bedding, futons, rugs, curtains, wall fabrics, shoes, and the like adhere to secretions discharged from a user's skin and exfoliated skin. Because these are nutrient sources such as bacteria and mold, it becomes a suitable medium for bacteria and the like to propagate,
The product of the bacterium produces an unpleasant odor, which in some cases causes skin diseases. In addition, futons, rugs, curtains, wall fabrics, and the like often generate mold during storage or use in a humid place. In this case, the fiber is deteriorated, and the quality is deteriorated due to contamination or the like. Furthermore,
In addition to these, it is desired that towels, towels, bandages, and the like be kept hygienic by suppressing bacterial contamination.

Conventionally, as a means for solving these problems,
BACKGROUND ART Liquids containing various germicides are attached to textiles by a method such as immersion, application, spraying, or the like. However, these methods often decompose or fall off due to external influences such as heating, washing with water, washing and the like, and the duration of the effect is short. As a method of extending the duration of efficacy, for example,
A method in which a part of a bactericidal quaternary ammonium salt is bonded to a fiber molecule through an organic silicon compound, a method in which a bactericide is strongly coated and adhered to a fiber surface by using a polymer compound having a strong adsorptivity to the fiber, A method of binding a bactericidal metal compound to the composition of a constituent material to impart antibacterial properties and the like has been performed (cited reference: Dictionary of Bactericidal and Fungicide First Edition: Japanese Society of Bactericidal and Fungicide).

However, in these methods, the compounds used have low heat resistance, cannot withstand the heating step during processing, are easily detached by washing, impair the properties of the material fibers, and have insufficient safety. In addition, there are various disadvantages such as complicated processing steps, high processing cost, and generation of harmful substances when the products are discarded or incinerated.

[0005]

DISCLOSURE OF THE INVENTION The present inventors have conducted intensive studies to overcome the above-mentioned problems of the prior art and to develop an antibacterial agent for fibers having no skin irritation. completed.

[0006]

SUMMARY OF THE INVENTION The object of the present invention is to provide a diglycerin monofatty acid ester in which the purity of the monofatty acid ester is 50% by weight or more and the number of carbon atoms of the fatty acid constituting the ester is in the range of 8 to 18. Has been found to be achieved by using one or more selected from natural fibers and / or synthetic fibers impregnated with at least one part thereof.

Hereinafter, the present invention will be described in detail. The antibacterial agent for fibers comprising a diglycerin monofatty acid ester having a monofatty acid ester purity of 50% by weight or more according to the present invention has never been used in the antibacterial processing of fibers, and its suitability is completely known. I didn't.

[0008] The polyglycerin fatty acid ester containing the product of the present invention is a safe compound as a food additive, with no restrictions imposed on the food used and the amount used. Among these compounds, it is known that glycerin monofatty acid ester, triglycerin fatty acid ester, hexaglycerin fatty acid ester, and decaglycerin fatty acid ester have antibacterial properties (Antimicrobial Agents and Chemothe
rapy, Nov. 1973, p. 501-506). In this document, the antibacterial evaluation of these polyglycerin fatty acid esters was
occus sp., Staphyrococcus aureus, Corynebacterium
sp., Nocardiaasteroides, and Micrococcus sp. were measured for the minimum growth inhibitory concentration (MIC) of five Gram-positive bacteria. The MIC value of each strain was significantly higher than that of known glycerin fatty acid esters having antibacterial properties. It is small and there is no description of antibacterial effects on Gram-negative bacteria, yeast, and fungi.

No antibacterial properties of the diglycerin monofatty acid ester used in the present invention are known, and no antibacterial properties are known. No antibacterial properties of the diglycerin monofatty acid ester used in the present invention are known, and no antifungal agent is known at all.

The diglycerin monofatty acid ester used in the present invention contains the monofatty acid ester in an amount of 50% by weight or more. The diglycerin monofatty acid ester used in the present invention has poor or no antifungal activity when the monofatty acid ester is less than 50% by weight.

The diglycerin monofatty acid ester used in the present invention contains the monofatty acid ester in an amount of 50% by weight or more. Generally, the diglycerin fatty acid ester is prepared by reacting diglycerin and a fatty acid in the absence of a catalyst or in the presence of a catalyst in the range of 180 to
Obtained by heating and mixing at 240 ° C. The esterification reaction is
Proceeds along an indiscriminate distribution, and in addition to unreacted diglycerin and diglycerin monofatty acid ester as reaction products,
The same diester, the same triester, and the same tetraester exist. The proportion of these is determined by the reaction molar ratio of diglycerin and fatty acid. Specifically, when diglycerin and palmitic acid are mixed and reacted until there is no unreacted fatty acid, the reaction products are almost as shown in the following table.

[0012]

[Table 1]

The monoester content of the reaction product of diglycerin and fatty acid does not exceed 50% by weight even if the reaction molar ratio is changed.

The diglycerin monofatty acid ester containing 50% by weight or more of the monofatty acid ester used in the present invention can be obtained by a method for removing unreacted diglycerin from an ordinary reaction product (however, in this method, the content of the monofatty acid ester is reduced). The maximum is only 55% by weight), a method of fractionating a solvent, a method of molecular distillation, and the like.
Known techniques can be employed for the unreacted substance removal method, solvent fractionation method, and molecular distillation method. The diglycerin monofatty acid ester containing 50% by weight or more of the monofatty acid ester used in the present invention preferably has 8 to 18 fatty acid carbon atoms.
Diglycerin monoester having a fatty acid carbon number of less than 8 causes generation of unpleasant odor and increased skin irritation. In addition, diglycerin monoester having a fatty acid carbon number of more than 18 has poor or no antibacterial properties. The diglycerin monofatty acid ester used in the present invention is a liquid or semi-solid compound at room temperature, is colorless and odorless, and has little or no irritation to the skin.

The diglycerin fatty acid ester used in the present invention may be other well-known fungicides and preservatives, for example, paraoxybenzoic acid esters, parachlor-metaxylenol, α-bromocinnamaldehyde, thiabendazole, glycerin fatty acid esters and the like. Can be used in combination, which is expected to enhance the initial effect and maintain the effect.

In the method of applying the antibacterial component of the present invention to a fiber material, various emulsions or solutions described below are prepared and used. That is, an emulsion is prepared by adding an emulsifier, a hydrophilic solvent, water and the like to the above compound, heating, mixing and homogenizing the compound. When dissolved in an organic solvent, it is prepared as a solution. Emulsions and solutions are prepared by conventional adjustment methods. If necessary, a viscosity modifier, a stabilizer, a coloring agent, a fragrance, and the like may be added.

Examples of the hydrophilic solvent include lower alcohols, alkylene glycols, alkylene glycol monoalkyl ethers, dialkylene glycol monoalkyl ethers, dimethyl sulfoxide, and N-methyl-2-.
Pyrrolidone or the like is used and is not particularly limited. Further, as the organic solvent, methanol, ethanol, propanol, butanol ethylene glycol,
Alcohols such as propylene glycol, ethers such as ethylene glycol monobutyl ether, propylene glycol monoethyl ether and dioxane, ketones such as acetone, methyl ethyl ketone and cyclohexanone, esters such as lower alcohol acetate, dimethylformamide and dimethylacetamide Examples thereof include acid amides and dimethyl sulfoxide, and are not particularly limited. When the treatment is performed at a high temperature, it is preferable to select a solvent having a high boiling point. Similarly, emulsifiers are also not limited in use, but typical examples thereof include alkyl sulfates, alkyl aryl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, dialkyl sulfosuccinic acids, polyoxyethylene sorbitan fatty acid esters, and sucrose. Fatty acid esters and the like.

The method of applying the emulsion or solution prepared by the above composition to a fiber material is as follows. First, in the case of the above emulsion, the emulsion is diluted with water to contain the active ingredient in an amount of 0.1 to 30% by weight. A liquid is prepared and treated by means of dipping, coating, spraying or the like so as to give about 0.1 to 5% by weight to the fiber product to be processed. In this case, if it is less than 0.1% by weight, the antibacterial effect is weak, and as long as it is used under normal use conditions, it is 5%.
It is not necessary to apply more than weight%. In the case of the above solution, the compound of the present invention is treated so as to give the above-described weight to the fiber product to be treated by a method of immersion, application, or spraying with or without dilution in water.

The diglycerin monofatty acid ester of the present invention is strongly applied to natural fibers such as cotton, silk and wool, synthetic fibers such as polyamide, polyester and acrylic, and semi-synthetic fibers such as rayon and acetate. Shows the strength. For example, acrylic and nylon fibers exhibit antibacterial activity even after 10 washes. Fiber products blended or woven with cotton, silk, and wool show extremely strong affinity
Antibacterial properties are imparted even after 0 washes. Therefore, as a processed fiber product, it is widely applied to underwear, socks, sports clothing, bedding, curtains, rugs, wall fabrics, cloths, towels, bandages, athletic shoes, bags, paper, pulp products, and the like. Textile products antibacterial processed using the antibacterial agent of the present invention,
In terms of gloss, smell, water repellency, etc., the original characteristics of the material fiber are not impaired. The compound used in the antibacterial agent of the present invention is specified as a food additive, and has a major feature that it is higher in safety than a bactericide conventionally used for antibacterial processing of textile products. is there.

[0020]

EXAMPLES The present invention will be described below with reference to examples.
The present invention is not limited to these examples.

Example 1 The antibacterial properties of textile products were evaluated using the diglycerin monofatty acid esters of the present invention shown in Table 2 and Comparative Examples. In the antibacterial test, the viable cell counts of unprocessed and processed samples were measured by the bacterial count method of the Textile Sanitation Processing Council. Evaluation method is evaluation index log
(B / C)> 2 was considered valid. Here, B: the viable cell count of the unprocessed sample after 18 hours of culture, and C: the viable cell count of the processed sample after 18 hours of culture.

[0022]

[Table 2]

30 parts by weight of the product of the present invention and 30 parts by weight of the comparative product are separately taken, and 10 parts by weight of sodium dioctylsulfosuccinate, 20 parts by weight of dimethyl sulfoxide, 20 parts by weight of isopropanol and 20 parts by weight of water are added and heated and mixed. An emulsion having an active ingredient concentration of 30% by weight was obtained. The cotton cloth was immersed in a 30-fold diluted aqueous solution of 30% by weight emulsifier, squeezed so that an amount of liquid equal to the weight of the cotton cloth was attached, and dried with 105 ° C. warm air for 10 minutes to obtain a sample cloth. The laundry sample cloth is J
Prepared by processing with IS L 1018 (H method). The antibacterial test used Staphylococcus aureus to measure the viable cell count. Table 3 shows the results. Further, an aqueous solution was prepared by diluting the 30% by weight emulsion of each of the Examples and Comparative Examples 10-fold, a cotton cloth was immersed, squeezed so that an amount of the liquid equal to the weight of the cotton cloth adhered, and heated with 105 ° C. warm air for 10 minutes. The sample cloth was dried and subjected to the same antibacterial test as described above to evaluate antibacterial properties. Table 4 shows the results.

[0024]

[Table 3]

[0025]

[Table 4]

In the embodiment using the antibacterial agent of the present invention, the antibacterial activity is maintained even after washing, and an excellent antibacterial fiber product can be obtained.

(Example 2) Using 30% by weight emulsified liquid of each of the product of the present invention and the comparative product prepared in Example 1, 30
A double-diluted aqueous solution was used, a polyester fabric was immersed in the solution, and a liquid having an amount equal to the weight of the fabric was adhered. An antibacterial test was performed on Staphylococcus aureus in the same manner as in Example 1 to measure the inhibition circle. Table 5 shows the measurement results.

[0028]

[Table 5]

As in Example 1, a good antibacterial effect was recognized for the polyester fabric.

Example 3 Each 30% by weight emulsion of the product of the present invention and the comparative product prepared in Example 1 was used as a 30-fold diluted aqueous solution, and one pair of socks (mixed spinning of acrylic, polyester, nylon, and hair) Was immersed in the solution, an amount of liquid equivalent to the weight of the sock was adhered, and air-dried. Two pairs of the treated socks were prepared for each pair of untreated ones, and after washing for one day, washing and drying were repeated three times, and the odor of the fourth wearing on the first day was compared. The shoes were brand new athletic shoes to prevent the effects of odor before the test. Table 6 shows the results.

[0031]

[Table 6]

[0032]

According to the present invention, it is possible to provide an antibacterial and deodorized fiber product which is excellent in safety, stability and washing resistance and does not impair the physical properties of the processed product. The active ingredient of the antibacterial agent used in the present invention is a polyglycerin fatty acid ester which is a food additive, and is hygienic and safe.

Claims (3)

[Claims] An antibacterial agent for fibers, comprising a diglycerin monofatty acid ester having a monofatty acid ester purity of 50% by weight or more as an active ingredient. 2. The antibacterial agent for fibers according to claim 1, wherein the carbon number of the fatty acid constituting the diglycerin monofatty acid ester is in the range of 8 to 18. 3. An antibacterial and deodorant treated fiber product comprising at least one part of one or more selected from the group consisting of natural fibers and synthetic fibers provided with diglycerin monofatty acid ester.