JP3077486B2 - Antibacterial agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antibacterial agent applicable to all antibacterial products. More specifically, the present invention relates to an antibacterial agent applicable to kitchen appliances, bathroom appliances, home electric appliances, interior materials in hospitals, textiles such as sheets, and medical equipment in homes.

[0002]

2. Description of the Related Art It has been conventionally practiced to incorporate a compound having antibacterial properties into a resin to obtain fibers and paints. Among the compounds having antibacterial properties, organic compounds have a problem in application to uses that are highly toxic and are in direct contact with food and the human body.
There is a disadvantage that resistant bacteria are easily generated. Therefore, a method using particles containing a metal element such as silver having antibacterial properties is recommended. These metal element-containing particles have advantages in that they are less toxic than organic compounds and hardly cause resistant bacteria.

[0003] Usually, the larger the surface area of the particles is, the more advantageous the bacteria prevention is. Therefore, a metal element is carried on the surface of porous ceramic particles such as zeolite, hydroxyapatite, etc. Alternatively, a bactericidal action by active ozone generated by a metal element as a catalyst is used. However, when metal elements on the particle surface are eluted as ions, these ions are easily oxidized by ultraviolet rays. For example, in the case of silver ions, silver oxides are quickly generated and discolored even with an amount of ultraviolet rays under sunlight.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an antibacterial agent having low toxicity, little coloring and discoloration, and easy to handle.

[0005]

That is, the present invention provides an antibacterial agent comprising a phenolic cyclic condensate and / or a derivative thereof adsorbed with an antibacterial metal ion in the presence of a basic compound. .

[0006] Calixarene, one of the phenol cyclic condensates, is generally easily obtained from a phenol derivative and paraformaldehyde with an alkali catalyst (potassium hydroxide or sodium hydroxide). Depending on the type of the phenol derivative, the type of the alkali catalyst, and the reaction temperature, each core compound can be obtained. Examples of the phenol derivative include octyl phenol, nonyl phenol, iso-propyl phenol, p-tert-butyl phenol, cresol and the like. Although not particularly limited, p-tert-butylphenol is preferred in terms of synthesis.

[0007] Calixarene is a cyclic oligomer of phenol, and depending on the number of nuclei, tetranuclear, pentanuclear, hexanuclear,
It is divided into heptanucleotides and octuploids. The functionality differs depending on each nucleus, and excellent effects can be obtained by using any of them. However, it is usually preferable to use an octanucleus from the viewpoint of easy production and handling.

[0008] Calixarene and its derivatives include p-tert-butylcalix (8) arene, p-tert-butylcalix (7) arene, p-tert-butylcalix
(6) Allene, p-tert-butyl calix (5) Allene, p-
tert-butylcalix (4) arene, acetylated tert-butylcalix (8) arene, acetylated tert-butylcalix (7) arene, acetylated tert-butylcalix (6) arene, acetylated tert-butylcalix (5) )
Allene, acetylated tert-butylcalix (4) arene and the like. The numbers in parentheses indicate the number of nuclei.

Sources of antibacterial metal ions include silver salts, copper salts, zinc salts, tin salts, cobalt salts, nickel salts, manganese salts, iron salts, and aluminum salts such as silver nitrate, silver chloride, and chloride chloride. Copper, copper sulfate, ferrous chloride and the like can be mentioned.

[0010] Antimicrobial metal ions are not adsorbed to the phenol cyclic condensate and / or a derivative thereof by merely contacting it, but by contacting in the presence of a basic compound, the metal ion is converted to phenol. Adsorbed on cyclic condensates and / or their derivatives. As the basic compound, conventionally known compounds can be used, but ammonia and amines such as methylamine, ethylamine, dimethylamine, diethylamine, and trimethylamine are preferable.

[0011]

The present invention will be described below with reference to examples. In the examples, “parts” means “parts by weight” and “%” means “% by weight”. [Example 1] 0.5 part of silver nitrate and 10%
91.8 parts of aqueous ammonia was added and dissolved, and 7.7 parts of p-tert-butylcalix (8) allene was added. After stirring well for about 150 hours, the mixture was washed by filtration and dried to obtain an antibacterial agent. Example 2 In a flask container, 0.5 part of silver nitrate, 5.0 parts of ethylamine and 86.8 parts of water were added and dissolved, and 7.7 parts of p-tert-butylcalix (6) arene was added. After stirring well for about 150 hours, the mixture was washed by filtration and dried to obtain an antibacterial agent.

Example 3 In a flask container, 0.5 g of silver nitrate was placed.
And 5.0 parts of ethylenediamine and 86.8 parts of water were added and dissolved, and 7.7 parts of p-tert-butylcalix (4) arene was added. After stirring well for about 150 hours, the mixture was washed by filtration and dried to obtain an antibacterial agent. Example 4 Example 1 except that silver nitrate was replaced with silver chloride.
An antibacterial agent was obtained in the same manner as described above. Example 5 Example 2 except that silver nitrate was replaced with silver chloride.
An antibacterial agent was obtained in the same manner as described above. Example 6 Example 3 except that silver nitrate was replaced with silver chloride.
An antibacterial agent was obtained in the same manner as described above.

Example 7 p-tert-butylcalix
(6) An antibacterial agent was obtained in the same manner as in Example 2 except that the allene was changed to p-tert-butylcalix (8) allene and the stirring time was set to 24 hours. [Example 8] p-tert-butylcalix (4)
-tert-butylcalix (8)
Except for 24 hours, an antibacterial agent was obtained in the same manner as in Example 2. Example 9 In a flask container, 0.5 part of silver chloride, 5.0 parts of ethylenediamine and 86.8 parts of water were added and dissolved, and p-tert-
Butylcalix (8) Allene (7.7 parts) was added. After stirring well for 24 hours, the mixture was filtered, washed and dried to obtain an antibacterial agent.

[Comparative Example 1] Silver nitrate 0.5
And 91.8 parts of a 5% aqueous acetone solution were added and dissolved.
7.7 parts of t-butyl calix (8) allene was added. After stirring well for 24 hours, the mixture was filtered, washed and dried to obtain an antibacterial agent. The 5% acetone aqueous solution was used to improve the wetting of p-tert-butylcalix (8) arene.

Comparative Example 2 p-tert-butylcalix
(8) An antibacterial agent was obtained in the same manner as in Comparative Example 1, except that allene was changed to p-tert-butylcalix (6) arene. [Comparative Example 3] p-tert-butylcalix (8)
An antibacterial agent was obtained in the same manner as in Comparative Example 1 except that -tert-butylcalix (4) was replaced with allene.

Two parts of the test specimens obtained in Examples 1 to 9 and Comparative Examples 1 to 3 were added to Liopol (Toyo Ink floor coating "Liopol IX-226G-215 Top A" / "Liopol").
IX-226 Series B "= 2/1, solid content 60%), 98 parts were mixed, poured into a frame and cured to obtain a test material having a thickness of 1 mm.

(Antibacterial test) The bacteria shown in Table 1 were 5 × 5 cm ²
Was sprayed on the surface of the test material and cultured for 24 hours. After the cultivation, the antibacterial activity was evaluated in comparison with the degree of proliferation of a control containing no specimen. The antibacterial activity was defined as-when the growth of the bacteria was equivalent to the growth level of the control, + when the growth was up to about 50% of the growth level of the control, and ++ when the growth was almost completely suppressed. Table 1 shows the results.

[0018]

[Table 1]

(Weather Resistance Test) The test materials were subjected to a weather resistance test at 70% humidity for 72 hours, 168 hours and 480 hours using "Xenon Long Life Weatherometer". The material stored in a cool dark place was used as a reference material, and the degree of discoloration was visually evaluated. The evaluation criterion was expressed in five levels, with 5 indicating no discoloration and 1 indicating significant discoloration. Table 2 shows the results.

[0020]

[Table 2]

[0021]

Industrial Applicability According to the present invention, an antibacterial agent which is excellent in heat resistance, has little discoloration, is easy to handle, can be widely used, and is industrially extremely useful can be provided.

────────────────────────────────────────────────── ─── of the front page continued (51) Int.Cl. ⁷ identification mark FI A01N 59/20 A01N 59/20 Z (58 ) investigated the field (Int.Cl. ^7, DB name) A01N 59/16 A01N 59 / 20 A01N 59/06 A01N 25/22 A01N 25/32

Claims (2)

(57) [Claims] An antibacterial agent comprising a phenol cyclic condensate and / or a derivative thereof adsorbed with an antibacterial metal ion in the presence of a basic compound. 2. The antibacterial agent according to claim 1, wherein the metal ion having antibacterial properties is at least one selected from silver, copper, zinc, tin, cobalt, nickel, manganese, iron and aluminum.