JPH02243604A - Industrial anti-mold agent - Google Patents

Industrial anti-mold agent

Info

Publication number
JPH02243604A
JPH02243604A JP6087689A JP6087689A JPH02243604A JP H02243604 A JPH02243604 A JP H02243604A JP 6087689 A JP6087689 A JP 6087689A JP 6087689 A JP6087689 A JP 6087689A JP H02243604 A JPH02243604 A JP H02243604A
Authority
JP
Japan
Prior art keywords
dicyclohexylamine
salt
industrial
mold agent
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP6087689A
Other languages
Japanese (ja)
Inventor
Masahiro Noda
昌宏 野田
Masaharu Fuchigami
正晴 渕上
Akira Akagawa
赤川 章
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yushiro Chemical Industry Co Ltd
Original Assignee
Yushiro Chemical Industry Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yushiro Chemical Industry Co Ltd filed Critical Yushiro Chemical Industry Co Ltd
Priority to JP6087689A priority Critical patent/JPH02243604A/en
Publication of JPH02243604A publication Critical patent/JPH02243604A/en
Pending legal-status Critical Current

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Abstract

PURPOSE:To obtain industrial anti-mold agent used for metal-processing oil, detergent or cooling water, etc., having excellent durability, a slight variation of effect with time at a low cost, containing dicyclohexylamine or salt of said compound as active ingredient. CONSTITUTION:The aimed industrial anti-mold agent contains >=60ppm (preferably 0.1-100wt.%) dicyclohexylamine and salt of said compound (preferably salt of 1-3C carboxylic acid or salt of inorganic acid such as hydrochloric acid). Dicyclohexylamine has excellent disinfecting property especially against fungi and anti-mold agent containing said compound as active indgredient is able to be safely used for metal-processing oil, detergent, aqueous paint, pulp for papermaking or cooling water in circulation system, etc. In a case of using after dilution, water, methanol or acetone, etc., is used as solvent and further, dispersant or emulsifier, etc., may be added.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は、水系で使用される工業用防黴剤に関する。[Detailed description of the invention] Industrial applications The present invention relates to an industrial fungicide used in an aqueous system.

従来の技術 従来、水溶性の金属加工用油剤、洗浄剤、水性ペイント
、製紙バルブ、循環系の冷却水などは、細菌類、真菌類
等の有害微生物の生育によって生じる種々の問題点を防
止するために防腐防黴剤が使用されていた。この種の工
業用防腐防黴剤としては、例えばトリアジン系化合物、
チアゾリン系化合物およびイミダシリン系化合物等が挙
げられる。
Conventional Technology Traditionally, water-soluble metalworking oils, cleaning agents, water-based paints, paper valves, cooling water for circulation systems, etc. have been used to prevent various problems caused by the growth of harmful microorganisms such as bacteria and fungi. Therefore, preservatives and fungicides were used. Examples of this type of industrial preservative and fungicide include triazine compounds,
Examples include thiazoline compounds and imidacilline compounds.

発明が解決しようとする課題 上記のような従来の工業用防腐防黴剤は以下に示すよう
な問題があった。
Problems to be Solved by the Invention The conventional industrial preservatives and fungicides as described above have had the following problems.

(1)効果の持続性に乏しい。(1) The sustainability of the effect is poor.

(2)金属加工用油剤や洗浄剤などの原液に配合した場
合には、原液の保管中に薬効を失ってしまう。
(2) If it is added to a stock solution such as a metalworking oil or cleaning agent, it will lose its medicinal efficacy during storage of the stock solution.

(3)高価であるとともに皮膚刺激性が強いことから添
加量が制約されるので、満足する効果が得られない。
(3) Since it is expensive and highly irritating to the skin, the amount added is limited, and therefore a satisfactory effect cannot be obtained.

本発明は上記のような従来の工業用防黴剤の有する問題
点に鑑みてなされたものであり、防鍵効果の持続性に優
れ、金属加工用油剤や洗浄剤等に配合した場合に原液保
管中の経時的な薬効の変化が小さく、かつ安価な工業用
防黴剤を提供することを目的とする。
The present invention has been made in view of the problems of conventional industrial antifungal agents as described above. The purpose of the present invention is to provide an inexpensive industrial fungicide whose medicinal efficacy changes little over time during storage.

課題を解決するための手段 本発明者らは、種々の化合物について有害微生物に対す
る殺菌性を試験した結果、ジシクロヘキシルアミンが特
に真菌類に対して優れた殺菌性を有し、工業用防黴剤と
して実用可能であることを見いだし本発明を完成した。
Means for Solving the Problems As a result of testing the bactericidal properties of various compounds against harmful microorganisms, the present inventors found that dicyclohexylamine has particularly excellent bactericidal properties against fungi and has been used as an industrial fungicide. They found that it is practical and completed the present invention.

すなわち本発明は、工業用防黴剤にジシクロヘキシルア
ミンを有効成分として含有させることにより上記問題点
を解決したものである。
That is, the present invention solves the above problems by incorporating dicyclohexylamine as an active ingredient in an industrial fungicide.

この本発明に係る工業用防黴剤は、ジシクロヘキシルア
ミンとしてそのまま使用することもできるが、炭素原子
数が1ないし3のカルボン酸の塩あるいは塩酸のような
無機酸の塩として使用することもできる。
The industrial fungicide according to the present invention can be used as dicyclohexylamine as it is, but it can also be used as a salt of a carboxylic acid having 1 to 3 carbon atoms or a salt of an inorganic acid such as hydrochloric acid. .

また、適当な溶媒(例えば、水、メタノール、エタノー
ル、アセトン等)で希釈するか、あるいは分散剤、乳化
剤等を添加して使用することもできる。
Further, it can be used by diluting it with a suitable solvent (for example, water, methanol, ethanol, acetone, etc.), or by adding a dispersant, an emulsifier, etc.

本発明の工業用防黴剤は、その効果を得るために、ジシ
クロヘキシルアミンまたはその塩として60ppm以上
の濃度が必要である。
The industrial fungicide of the present invention requires a concentration of 60 ppm or more as dicyclohexylamine or its salt in order to obtain its effect.

なお、本発明の防黴剤を工業用防黴剤として用いる場合
には、ジシクロヘキシルアミンまたはその塩としての有
効成分が0.1ないし100重量%とじて使用すること
が好ましい。
When the antifungal agent of the present invention is used as an industrial antifungal agent, it is preferable to use the active ingredient in the form of dicyclohexylamine or a salt thereof at 0.1 to 100% by weight.

以上示した本発明の防黴剤は、例えば水溶性金属加工用
油剤、洗浄剤、水性ペイント、製紙バルブ、循環系の冷
却水などに関する工業分野において使用することができ
る。
The antifungal agent of the present invention described above can be used in industrial fields related to, for example, water-soluble metal processing oils, cleaning agents, water-based paints, paper manufacturing valves, and cooling water for circulation systems.

実施例 次に、本発明に係る工業用防黴剤の実施例について、そ
の防黴効果を各種実験により確かめた。
Examples Next, the anti-mildew effect of the industrial anti-mildew agent according to the present invention was confirmed through various experiments.

本発明の実施例として、ジシクロヘキシルアミン、ジシ
クロへキジルアミーンの蟻酸塩、ジシクロヘキシルアミ
ンの酢酸塩、ジシクロヘキシルアミンのプロピオン酸塩
およびジシクロヘキシルアミンの塩酸塩をそれぞれ有効
成分として含有する工業用防黴剤を選択し、また比較例
として以下に示す市販の防腐剤を選択して防黴効果を比
較する各種の実験を行った。
As an example of the present invention, an industrial fungicide containing dicyclohexylamine, dicyclohexylamine formate, dicyclohexylamine acetate, dicyclohexylamine propionate, and dicyclohexylamine hydrochloride as active ingredients was selected. In addition, as a comparative example, various experiments were conducted to compare the antifungal effects of the commercially available preservatives shown below.

市販防腐剤A:ニブルトップ3(商品名、ベンゾイソチ
アゾリン系、式日薬品 工業社製) 市販防腐剤B:パラオキシ安息香酸(吉富製薬社製) 市販防腐剤C:PROXEL  CRL  (商品名、
ベンゾイソチアゾリン系、 ICI社製) 市販防腐剤D:グロタン(商品名、トリアジン系、三愛
石油社製) (実験l) 上記のような本発明の実施例の工業用防黴剤と市販の防
腐剤とについて、普通寒天培地により、フザリウム(f
usariuml、セファロスポリウム(cephal
osporium)、アスペルギルス(asper−g
illuslおよびペニシリウム(penicilli
umlの各真菌類に対する最低生育阻止濃度(MIC)
を測定した。この結果を第1表に示す。
Commercially available preservative A: Nibble Top 3 (trade name, benzisothiazoline series, manufactured by Shikinichi Yakuhin Kogyo Co., Ltd.) Commercially available preservative B: Paraoxybenzoic acid (manufactured by Yoshitomi Pharmaceutical Co., Ltd.) Commercially available preservative C: PROXEL CRL (trade name,
(benzisothiazoline type, manufactured by ICI) Commercially available preservative D: Grotan (trade name, triazine type, manufactured by San-Ai Oil Co., Ltd.) (Experiment 1) Industrial fungicide of the example of the present invention as described above and commercially available preservative Regarding, Fusarium (f
usarium, cephalosporium
osporium), aspergillus (asper-g
illusl and Penicillium (penicilli)
Minimum inhibitory concentration (MIC) for each fungus in uml
was measured. The results are shown in Table 1.

この表から明らかなように、本発明の工業用防黴剤は、
従来の市販の防腐剤と同等以上の防黴効果を有すること
が確認できた。
As is clear from this table, the industrial fungicide of the present invention is
It was confirmed that the anti-mildew effect was equal to or greater than that of conventional commercially available preservatives.

第1表 注1)ジシクロヘキシルアミン 注2)プルトップ33:ベンゾイソチアゾリン系 武田
薬品工業社製注3)バラオキシ安息香酸ブチル:吉富製
薬社製注4)PROXEL  CRL:ベンゾイソチア
ゾリン系 IC1社製注5)グロタン:トリアジン系 
三愛石油社製(実験2) (試料の調製) JIS  K  224・1に規定されているW2種1
号に該当するソリュブルタイプの水溶性切削油剤に、防
腐剤成分として本発明の実施例の工業用防黴剤および市
販の防腐剤を下記に示すように配合して試料を調製した
Table 1 Note 1) Dicyclohexylamine Note 2) Pull top 33: Benzisothiazoline type Manufactured by Takeda Pharmaceutical Company Note 3) Butyl roseoxybenzoate: Manufactured by Yoshitomi Pharmaceuticals Note 4) PROXEL CRL: Benzisothiazoline type Manufactured by IC1 Note 5) Grotan : Triazine type
Manufactured by San-ai Oil Co., Ltd. (Experiment 2) (Sample preparation) W2 type 1 specified in JIS K 224.1
A sample was prepared by adding the industrial fungicide of the example of the present invention and a commercially available preservative as a preservative component to a soluble type water-soluble cutting fluid corresponding to No.

(実施例の試料) 試料1ニジシクロヘキシルアミン 1重量%配合品 試料2ニジシクロヘキシルアミン 2重量%配合品 試料3ニジシクロヘキシルアミンのギ酸塩(等モル反応
物)  1重量%配合品 試料4ニジシクロヘキシルアミンのギ酸塩(等モル反応
物) 2重量%配合品 試料5ニジシクロヘキシルアミンのプロピオン酸塩(等
モル反応物)1重量%配合品 試料6:ジシクロヘキシルアミンの塩酸塩(等モル反応
物) 1重量%配合品 (比較例の試料) 試料7:市販防腐剤A 1重【%配合品試料8:市販防
腐剤B 1重量%配合品試料9:市版防腐剤01重量%
配合品 試料10:市販防腐剤D 1重量%配合品試料11:防
腐成分無配合品 (菌液の調製) 真菌類によってスライムを生成した水溶性切削油剤の老
化液より、フザリウム及びセファロスポリウムを分離し
た。それぞれの菌をポテトデキストロース培地で増殖さ
せ、I X 10”個/ m itをカウントする液を
調製した。
(Samples of Examples) Sample 1 Ni-dicyclohexylamine 1% by weight combination Sample 2 Ni-dicyclohexylamine 2% by weight combination Sample 3 Ni-dicyclohexylamine formate (equimolar reactant) 1% by weight combination Sample 4 Ni-dicyclohexylamine Formate of dicyclohexylamine (equimolar reactant) 2% by weight Sample 5 Propionate of dicyclohexylamine (equimolar reactant) 1% by weight Sample 6: Hydrochloride of dicyclohexylamine (equimolar reactant) 1% by weight % blended product (sample of comparative example) Sample 7: Commercially available preservative A 1 weight [% blended product Sample 8: Commercially available preservative B 1% by weight blended product Sample 9: Commercial preservative 0 1% by weight
Compounded product sample 10: Commercially available preservative D 1% by weight Compounded product sample 11: Preservative-free product (preparation of bacterial liquid) Fusarium and Cephalosporium were extracted from the aged liquid of a water-soluble cutting fluid that had produced slime by fungi. separated. Each of the bacteria was grown in a potato dextrose medium, and a solution for counting I x 10'' cells/mit was prepared.

(真菌数の測定) 前記のようにして調製した各試料1ないし11をそれぞ
れ50.100.150.200.300倍に希釈し、
これらの希釈液中に上記のように調製したフザリウムお
よびセファロスポリウムの菌液をそれぞれ10重量%添
加し、30℃の恒温槽内に静置した。そして、24時間
後ポテトデキトロース培地で真菌数を測定した。この結
果を、フザリウムについて第2表に、セファロスポリウ
ムについて第3表に示す。
(Measurement of the number of fungi) Each sample 1 to 11 prepared as described above was diluted 50.100.150.200.300 times,
10% by weight of each of the Fusarium and Cephalosporium bacterial solutions prepared as described above was added to these diluted solutions, and the mixture was left standing in a constant temperature bath at 30°C. After 24 hours, the number of fungi was measured using potato dextrose medium. The results are shown in Table 2 for Fusarium and Table 3 for Cephalosporium.

上記の各結果から、本発明の各実施例の工業用防黴剤は
、従来の市販の防腐剤と比較して、試験菌株フザリウム
およびセファロスポリウムに対し、比較的少量で薬効が
得られることが確認できた。
From the above results, the industrial fungicide of each example of the present invention has a medicinal effect against the test strains Fusarium and Cephalosporium in a relatively small amount compared to conventional commercially available preservatives. was confirmed.

(以下空白) 第2表 本試験菌株:フザリウム 第3表 本試験菌株:セファロスポリウム 第4表 (実験3) 実験2で用いた試料1ないし11と同じ試料油剤を用い
て50倍の希釈液を調整した。これらの希釈液300m
!2に鋳鉄切屑を20重量%加え、1.2および4日目
に、真菌類によるスライムを生成した水滴性切削油剤の
老化液(真菌数1×103個/ m 12 )を5重量
%添加した。
(Blank below) Table 2 Main test strain: Fusarium Table 3 Main test strain: Cephalosporium Table 4 (Experiment 3) 50-fold dilution using the same sample oil as Samples 1 to 11 used in Experiment 2 adjusted. 300ml of these diluted solutions
! 20% by weight of cast iron chips were added to 1.2 and 4th day, and 5% by weight of an aged water droplet cutting fluid (number of fungi 1 x 103/m12) that had produced slime due to fungi was added. .

これらの液を37℃、150rpmの条件で振どう培養
し、真菌数の経時変化を測定した。その結果を第4表に
示す。
These solutions were cultured under shaking conditions at 37° C. and 150 rpm, and changes in the number of fungi over time were measured. The results are shown in Table 4.

この結果から、本発明の各実施例は比較例の防腐剤と比
較して薬効の持続性が優れていることが分った。
From this result, it was found that each of the examples of the present invention had superior durability of medicinal efficacy compared to the preservative of the comparative example.

(実験4) 実験2で用いた試料1ないし10と同じ試料油剤を30
0m12のガラス容器に200mj2採取し、軟鋼板(
spcc、30X30X1mm)を加えて50℃の恒温
槽に静置した。3力月経過後、各試料油剤を50.10
0.150.200および300倍に希釈し、セファロ
スポリウムを試験菌株として用い、実験2と同じ方法で
各防黴剤の薬効を評価した。その結果を第5表に示す。
(Experiment 4) 30% of the same sample oil as Samples 1 to 10 used in Experiment 2
200mj2 was collected in a 0m12 glass container, and a mild steel plate (
spcc, 30 x 30 x 1 mm) and left in a thermostat at 50°C. After 3 months, each sample oil was 50.10%
The efficacy of each antifungal agent was evaluated in the same manner as in Experiment 2 by diluting it 0.150.200 and 300 times and using Cephalosporium as a test strain. The results are shown in Table 5.

この結果から、水溶性切削油剤の原液に添加された本発
明の実施例の工業用防黴剤は、従来の防黴剤と比較して
保管中における薬効の持続性が高いことが認められた。
From this result, it was confirmed that the industrial fungicide of the example of the present invention, which was added to the stock solution of water-soluble cutting fluid, had a higher persistence of medicinal effect during storage compared to conventional fungicide. .

第5表 本試験菌株:セファロスボリウム 以上示したように、本発明の各実施例の工業用防黴剤は
、真菌類に対して従来から市販の防腐剤と同等以上の殺
菌性を有すると共に持続性が優れている。また、水溶性
切削油剤に配合した場合の経時的な殺菌効果の消失が認
められない。
Table 5 Main test strain: Cephalosborium As shown above, the industrial fungicides of each example of the present invention have bactericidal properties against fungi that are equivalent to or higher than conventional commercially available preservatives. Excellent durability. Furthermore, no loss of bactericidal effect over time was observed when the compound was added to a water-soluble cutting fluid.

このような本発明の防黴剤は、従来の市販の防腐剤に比
較すると非常に安価である。したがって、本発明の防黴
剤を用いることによって、経済的で良好な防黴効果が得
られる。
The antifungal agent of the present invention is very inexpensive compared to conventional commercially available preservatives. Therefore, by using the antifungal agent of the present invention, an economical and good antifungal effect can be obtained.

発明の効果 本発明により、従来の工業用防黴剤と比較して防黴効果
の持続性に優れ、金属加工用油剤や洗浄剤等に配合した
場合に原液保管中の経時的な薬効の変化が小さく、かつ
安価な工業用防黴剤を提供することができた。
Effects of the Invention The present invention has excellent long-lasting anti-mold effects compared to conventional industrial anti-mold agents, and when added to oils for metal processing, cleaning agents, etc., the medicinal efficacy changes over time during storage of the undiluted solution. We were able to provide an industrial fungicide with a small size and low cost.

出願人  ユシロ化学工業株式会社Applicant: Yushiro Chemical Industry Co., Ltd.

Claims (1)

【特許請求の範囲】[Claims] ジシクロヘキシルアミン又はその塩を含有することを特
徴とする工業用防黴剤。
An industrial fungicide characterized by containing dicyclohexylamine or a salt thereof.
JP6087689A 1989-03-15 1989-03-15 Industrial anti-mold agent Pending JPH02243604A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP6087689A JPH02243604A (en) 1989-03-15 1989-03-15 Industrial anti-mold agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6087689A JPH02243604A (en) 1989-03-15 1989-03-15 Industrial anti-mold agent

Publications (1)

Publication Number Publication Date
JPH02243604A true JPH02243604A (en) 1990-09-27

Family

ID=13155019

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6087689A Pending JPH02243604A (en) 1989-03-15 1989-03-15 Industrial anti-mold agent

Country Status (1)

Country Link
JP (1) JPH02243604A (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5115616A (en) * 1974-07-31 1976-02-07 Kodama Kyodai Shoten Kk KATORISENKOYOBOBAIZAI
JPS61197693A (en) * 1985-02-12 1986-09-01 Yushiro Do Brazil Ind Chem Ltd Water-soluble cutting and grinding oil

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5115616A (en) * 1974-07-31 1976-02-07 Kodama Kyodai Shoten Kk KATORISENKOYOBOBAIZAI
JPS61197693A (en) * 1985-02-12 1986-09-01 Yushiro Do Brazil Ind Chem Ltd Water-soluble cutting and grinding oil

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