JP2010024206A - Commercial antiseptic and antifungal agent - Google Patents
Commercial antiseptic and antifungal agent Download PDFInfo
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- JP2010024206A JP2010024206A JP2008190177A JP2008190177A JP2010024206A JP 2010024206 A JP2010024206 A JP 2010024206A JP 2008190177 A JP2008190177 A JP 2008190177A JP 2008190177 A JP2008190177 A JP 2008190177A JP 2010024206 A JP2010024206 A JP 2010024206A
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Abstract
Description
本発明は、工業用殺菌剤組成物に関し、特に、広い抗菌スペクトラムを有する工業用防腐防かび剤に関する。 The present invention relates to an industrial disinfectant composition, and in particular, to an industrial antiseptic and fungicide having a broad antibacterial spectrum.
紙パルプの製造に用いられる水、産業分野における循環冷却水等の種々の用水、水性塗料、エマルジョン、捺染糊、皮革等の製造に用いられる水に繁殖した微生物は、被処理物、被洗浄物または処理設備等の腐食やかびの原因となる。工業用水等における有害微生物の発生を抑制または防除する薬剤の１つとしてイソチアゾリン系化合物が知られている。しかし、イソチアゾリン系化合物は、実用濃度では抗菌スペクトラムが狭く、多種の微生物に対しては対応しきれないという問題点を有している。さらに、このイソチアゾリン系化合物のフリー体は水、湿気、温度等に対して非常に敏感で分解し易いため、通常は水を含まない有機溶媒に溶解させた状態で保存されている。 Water used in the manufacture of pulp and paper, water used for various purposes such as circulating cooling water in the industrial field, water-borne paints, emulsions, printing paste, leather used in the manufacture of water, etc. Or it may cause corrosion or mold of processing equipment. An isothiazoline-based compound is known as one of agents that suppress or control the generation of harmful microorganisms in industrial water and the like. However, the isothiazoline-based compound has a problem that the antibacterial spectrum is narrow at a practical concentration and cannot cope with various microorganisms. Furthermore, the free form of this isothiazoline-based compound is very sensitive to water, moisture, temperature and the like and is easily decomposed. Therefore, it is usually stored in a state dissolved in an organic solvent not containing water.
工業用防腐防かび剤の抗菌スペクトラムを拡げるため、種々の抗菌、防かび剤や防藻剤との併用が検討され、例えば、２−メチル−４−イソチアゾリン−３−オンと２−ブロモ−２−ニトロ−１，３−プロパンジオールとの併用については特許文献１または２に記載されており、２−メチル−４−イソチアゾリン−３−オンと２−ｎ−オクチル−４−イソチアゾリン−３−オンとの併用については特許文献３に記載されている。
イソチアゾリン系化合物の溶解に適した有機溶媒として、通常はグリコール系有機溶媒等が用いられている。しかし、該グリコール系有機溶媒で溶液化した製剤は、消防法による危険物の指定を受けており、その取扱いや保存には特別な注意や設備を必要とするという問題があった。安全に使用できるイソチアゾリン系化合物含有の製剤として、水で希釈し有機溶媒の比率を下げた場合、イソチアゾリン系化合物の濃度を高くすることができず、また使用できるイソチアゾリン系化合物の種類も限定されるため、広い抗菌スペクトラムを有する工業用防腐防かび剤を得ることができないという問題があった。 As an organic solvent suitable for dissolving the isothiazoline-based compound, a glycol-based organic solvent or the like is usually used. However, the preparation in solution with the glycol organic solvent has been designated as a dangerous substance by the Fire Service Act, and there has been a problem that special care and equipment are required for its handling and storage. As a preparation containing an isothiazoline compound that can be used safely, the concentration of the isothiazoline compound cannot be increased when the ratio of the organic solvent is decreased by dilution with water, and the types of isothiazoline compounds that can be used are also limited. Therefore, there was a problem that an industrial antiseptic / fungal agent having a wide antibacterial spectrum could not be obtained.
そこで、本発明者らは、溶媒系を最適化することにより親水性のイソチアゾリン化合物と疎水性イソチアゾリン化合物を併用し、かつ第三の殺菌剤成分として２−ブロモ−２−ニトロ−１，３−プロパンジオールを配合することにより、広い抗菌スペクトラムが実現されることを見出し、本発明を完成するに至った。
すなわち本発明は、以下の通りである。
〔１〕殺菌活性配合剤として、２−ブロモ−２−ニトロ−１，３−プロパンジオール、下記式（１）で示される親水性イソチアゾリン系化合物、下記式（２）で示される疎水性イソチアゾリン系化合物および極性溶媒から調製されることを特徴とする、工業用防腐防かび剤。
Therefore, the present inventors have used a hydrophilic isothiazoline compound and a hydrophobic isothiazoline compound together by optimizing the solvent system, and 2-bromo-2-nitro-1,3- It has been found that a broad antibacterial spectrum is realized by blending propanediol, and the present invention has been completed.
That is, the present invention is as follows.
[1] As a bactericidal activity compounding agent, 2-bromo-2-nitro-1,3-propanediol, a hydrophilic isothiazoline compound represented by the following formula (1), and a hydrophobic isothiazoline compound represented by the following formula (2) An industrial antiseptic and fungicide characterized in that it is prepared from a compound and a polar solvent.
式（１）： Formula (1):
〔式中、Ｒ１はＣ１−３のアルキル基を示す。〕
式（２）：
Wherein, R 1 represents an alkyl group of C 1-3. ]
Formula (2):
〔式中、Ｒ２はＣ６−１２のアルキル基を示す。〕
〔２〕前記親水性イソチアゾリン系化合物が、２−メチル−４−イソチアゾリン−３−オンであり、前記疎水性イソチアゾリン系化合物が、２−ｎ−オクチル−４−イソチアゾリン−３−オンである、前記〔１〕記載の工業用防腐防かび剤。
〔３〕２−ブロモ−２−ニトロ−１，３−プロパンジオールを１０〜２５重量％、前記親水性イソチアゾリン系化合物を０．５〜５重量％および前記疎水性イソチアゾリン系化合物を０．５〜５重量％含有してなる、前記〔１〕または〔２〕記載の工業用防腐防かび剤。
〔４〕前記極性溶媒が少なくとも水および水溶性グリコール系溶媒を含む、前記〔１〕〜〔３〕のいずれかに記載の工業用防腐防かび剤。
〔５〕水を１０〜３０重量％および水溶性グリコール系溶媒を３５〜７９重量％含有してなる、前記〔４〕記載の工業用防腐防かび剤。
[Wherein, R 2 represents a C 6-12 alkyl group. ]
[2] The hydrophilic isothiazoline compound is 2-methyl-4-isothiazolin-3-one, and the hydrophobic isothiazoline compound is 2-n-octyl-4-isothiazolin-3-one, [1] The industrial antiseptic and fungicide according to [1].
[3] 10 to 25% by weight of 2-bromo-2-nitro-1,3-propanediol, 0.5 to 5% by weight of the hydrophilic isothiazoline compound and 0.5 to 5% of the hydrophobic isothiazoline compound The industrial antiseptic and fungicidal agent according to the above [1] or [2], comprising 5% by weight.
[4] The industrial antiseptic and fungicide according to any one of [1] to [3], wherein the polar solvent contains at least water and a water-soluble glycol solvent.
[5] The industrial antiseptic and fungicide according to the above [4], comprising 10 to 30% by weight of water and 35 to 79% by weight of a water-soluble glycol solvent.
広い抗菌スペクトラムを有する工業用防腐防かび剤の提供。 Providing industrial antiseptic and fungicides with a broad antibacterial spectrum.
以下、本発明について詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の工業用防腐防かび剤は、２−ブロモ−２−ニトロ−１，３−プロパンジオール、下記式（１）で示される親水性イソチアゾリン系化合物、下記式（２）で示される疎水性イソチアゾリン系化合物および極性溶媒から調製される。 The industrial antiseptic / fungal agent of the present invention is 2-bromo-2-nitro-1,3-propanediol, a hydrophilic isothiazoline compound represented by the following formula (1), and a hydrophobic compound represented by the following formula (2). Prepared from isothiazoline-based compounds and polar solvents.
本発明に用いる２−ブロモ−２−ニトロ−１，３−プロパンジオールは、工業用殺菌剤として従来から用いられている公知化合物であり、商業的に入手可能な化合物である。 2-Bromo-2-nitro-1,3-propanediol used in the present invention is a known compound conventionally used as an industrial disinfectant and is a commercially available compound.
本発明の２−ブロモ−２−ニトロ−１，３−プロパンジオールの配合量は特に限定されないが、好ましくは１０〜２５重量％、さらに好ましくは１０〜２０重量％配合される。 The blending amount of 2-bromo-2-nitro-1,3-propanediol of the present invention is not particularly limited, but is preferably 10 to 25% by weight, more preferably 10 to 20% by weight.
本発明に用いられる親水性イソチアゾリン系化合物は、下記式（１）で示される。
式（１）：
The hydrophilic isothiazoline compound used in the present invention is represented by the following formula (1).
Formula (1):
〔式中、Ｒ１はＣ１−３のアルキル基を示す。〕 [Wherein, R 1 represents a C 1-3 alkyl group. ]
Ｃ１−３アルキルとしては、例えば、メチル、エチル、ｎ−プロピル、およびイソプロピルが挙げられ、メチルが最も好ましい。 C 1-3 alkyl includes, for example, methyl, ethyl, n-propyl, and isopropyl, with methyl being most preferred.
このような親水性イソチアゾリン系化合物としては、より具体的には、２−メチル−４−イソチアゾリン−３−オン（以下、ＭＩＴと略することもある）が挙げられる。 More specific examples of such a hydrophilic isothiazoline-based compound include 2-methyl-4-isothiazolin-3-one (hereinafter sometimes abbreviated as MIT).
本発明に用いられる疎水性イソチアゾリン系化合物は、下記式（２）で示される。
式（２）：
The hydrophobic isothiazoline compound used in the present invention is represented by the following formula (2).
Formula (2):
〔式中、Ｒ２はＣ６−１２のアルキル基を示す。〕 [Wherein, R 2 represents a C 6-12 alkyl group. ]
Ｃ６−１２アルキルとしては、例えば、ヘキシル、ヘプチル、ｎ−オクチル、イソオクチル、２−エチルヘキシル、ノニル、デシル、イソデシル、ウンデシル、ドデシル等が挙げられ、ｎ−オクチルが最も好ましい。 Examples of C 6-12 alkyl include hexyl, heptyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, isodecyl, undecyl, dodecyl, and the like, and n-octyl is most preferable.
このような疎水性イソチアゾリン系化合物としては、より具体的には、２−ｎ−オクチル−４−イソチアゾリン−３−オン（以下、ＯＩＴと略することもある）が挙げられる。 More specific examples of such a hydrophobic isothiazoline-based compound include 2-n-octyl-4-isothiazolin-3-one (hereinafter sometimes abbreviated as OIT).
前記の親水性イソチアゾリン系化合物および疎水性イソチアゾリン系化合物はいずれも公知の化合物であり、たとえば米国特許第３７６１４８８号明細書、米国特許第３８４９４３０号明細書、米国特許第３８７０７９５号明細書、米国特許第４０６７８７８号明細書、米国特許第４１５００２６号明細書、米国特許第４２４１２１４号明細書、米国特許第３５１７０２２号明細書、米国特許第３０６５１２３号明細書、米国特許第３７６１４８９号明細書、および米国特許第３８４９４３０号明細書等に記載の方法またはそれらに準ずる方法によって製造することができる。 The hydrophilic isothiazoline-based compound and the hydrophobic isothiazoline-based compound are both known compounds. For example, US Pat. No. 3,761,488, US Pat. No. 3,849,430, US Pat. No. 3,870,795, US Pat. US Pat. No. 4,067,878, US Pat. No. 4,15,0026, US Pat. No. 4,241,214, US Pat. No. 3,571,022, US Pat. No. 3,065,123, US Pat. No. 3,761,489, and US Pat. No. 3,849,430. It can be produced by the method described in the specification of the application or the like or a method analogous thereto.
本発明の工業用防腐防かび剤において、２−ブロモ−２−ニトロ−１，３−プロパンジオール、親水性イソチアゾリン系化合物、疎水性イソチアゾリン系化合物および極性溶媒との配合割合は、特に限定されないが、好ましくは、２−ブロモ−２−ニトロ−１，３−プロパンジオールを１０〜２５重量％、親水性イソチアゾリン系化合物を０．５〜５重量％、疎水性イソチアゾリン系化合物を０．５〜５重量％、より好ましくは、２−ブロモ−２−ニトロ−１，３−プロパンジオールを１０〜２０重量％、親水性イソチアゾリン系化合物を１〜２重量％、疎水性イソチアゾリン系化合物を１〜２重量％配合することで、優れた腐敗防止効果を得ることができる。 In the industrial antiseptic and fungicide of the present invention, the blending ratio of 2-bromo-2-nitro-1,3-propanediol, hydrophilic isothiazoline compound, hydrophobic isothiazoline compound and polar solvent is not particularly limited. Preferably, 10 to 25% by weight of 2-bromo-2-nitro-1,3-propanediol, 0.5 to 5% by weight of hydrophilic isothiazoline compound, and 0.5 to 5 of hydrophobic isothiazoline compound. % By weight, more preferably 10 to 20% by weight of 2-bromo-2-nitro-1,3-propanediol, 1 to 2% by weight of hydrophilic isothiazoline compound, and 1 to 2% of hydrophobic isothiazoline compound %, It is possible to obtain an excellent anti-corruption effect.
（製造方法）
本発明の工業用防腐防かび剤は、常温、常圧下において、極性溶媒に２−ブロモ−２−ニトロ−１，３−プロパンジオール、親水性イソチアゾリン系化合物、疎水性イソチアゾリン系化合物を添加し混合することにより、極性溶媒を含む液剤として調製することができる。該混合は、例えば１〜４時間、攪拌することにより行われる。
(Production method)
The industrial antiseptic / fungal agent of the present invention is a mixture of 2-bromo-2-nitro-1,3-propanediol, hydrophilic isothiazoline compound and hydrophobic isothiazoline compound added to a polar solvent at room temperature and normal pressure. By doing so, it can be prepared as a liquid agent containing a polar solvent. The mixing is performed, for example, by stirring for 1 to 4 hours.
極性溶媒としては、各成分を溶解し、または、分散し得る溶剤であれば特に限定されないが例えば、水、アルコール系溶媒（例えばメタノール、エタノール、ｎ−プロパノール、ｉｓｏ−プロパノール、ｎ−ブタノール、ｔｅｒｔ−ブタノール、３−メチル−３−メトキシブタノール等）、グリコール系溶媒等（例えば、エチレングリコール、ジエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、ポリプロピレングリコール、プロパンジオール、ブタンジオール、ペンタンジオール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、トリプロピレングリコールモノメチルエーテル等）が挙げられるが、溶媒の安全性および適度なイソチアゾリン系化合物の濃度を確保し所望の防腐防かび性を達成する観点から少なくとも水および水溶性グリコール系溶媒を含む混合溶媒が好ましい。水溶性グリコール系溶媒としては疎水性のＯＩＴの溶解性に優れたジエチレングリコール（以下、ＤＥＧと略することもある）が最も好ましい。 The polar solvent is not particularly limited as long as it can dissolve or disperse each component. For example, water, alcohol solvents (for example, methanol, ethanol, n-propanol, iso-propanol, n-butanol, tert) -Butanol, 3-methyl-3-methoxybutanol, etc.), glycol solvents, etc. (for example, ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, propanediol, butanediol, pentane) Diol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, polyethylene Glycol monoethyl ether, tripropylene glycol monomethyl ether, etc.), but at least water and water-soluble glycol type from the viewpoint of ensuring the safety of the solvent and the appropriate concentration of the isothiazoline compound to achieve the desired antiseptic and fungicidal properties A mixed solvent containing a solvent is preferred. The water-soluble glycol solvent is most preferably diethylene glycol (hereinafter sometimes abbreviated as DEG), which is excellent in the solubility of hydrophobic OIT.
混合溶媒に用いる水は、通常の水、例えば、水道水、飲水、イオン交換水、純水等が挙げられ、工業用水等も使用可能であるが、イオン交換水が好ましい。 The water used for the mixed solvent includes normal water, for example, tap water, drinking water, ion exchange water, pure water, and the like, and industrial water can be used, but ion exchange water is preferable.
本発明の工業用防腐防かび剤において、極性溶媒の配合量は特に限定されないが、好ましくは水を１０〜３０重量％、水溶性グリコール系溶媒を３５〜７９重量％、より好ましくは水を１０〜２５重量％、水溶性グリコール系溶媒を４０〜７９重量％とすることが好ましい。 In the industrial antiseptic and fungicide of the present invention, the blending amount of the polar solvent is not particularly limited, but preferably 10 to 30% by weight of water, 35 to 79% by weight of water-soluble glycol solvent, more preferably 10 of water. It is preferable that the amount of water-soluble glycol solvent is 40 to 79% by weight.
更に本発明に係わる工業用防腐防かび剤は、当業者に添加剤として知られている従来の他の成分を、本発明の工業用殺菌組成物の優れた効果を阻害しない範囲において、適宜含むことができる。例えば、増粘剤、消泡剤、ｐＨ調整剤、安定化剤、香料、分散剤、着色剤、変色防止安定化剤、錯化剤および活性組成物の劣化を防止する安定化剤等が挙げられる。 Furthermore, the industrial antiseptic / fungal agent according to the present invention appropriately contains other conventional components known as additives to those skilled in the art within a range not inhibiting the excellent effect of the industrial sterilizing composition of the present invention. be able to. Examples include thickeners, antifoaming agents, pH adjusters, stabilizers, fragrances, dispersants, colorants, anti-discoloration stabilizers, complexing agents, and stabilizers that prevent deterioration of the active composition. It is done.
（発明の用途）
このようにして得られる本発明の工業用防腐防かび剤は、紙パルプの製造に用いられる水、産業分野における循環冷却水等の種々の用水、水性塗料、エマルジョン、捺染糊、皮革等の製造に用いられる水等に添加することにより、それらにおける微生物の繁殖を阻止することができる。
(Application of the invention)
The industrial antiseptic / fungal agent of the present invention thus obtained is used for the production of water for use in the production of paper pulp, various waters such as circulating cooling water in the industrial field, water-based paints, emulsions, printing pastes, leathers, etc. By adding to water or the like used in the above, the growth of microorganisms in them can be prevented.
本発明の工業用防腐防かび剤を上記のように使用する際には、有効成分、即ち、２−ブロモ−２−ニトロ−１，３−プロパンジオール、下記式（１）で示される親水性イソチアゾリン系化合物および下記式（２）で示される疎水性イソチアゾリン系化合物の合計量が、約１０〜１０００ｐｐｍとなるように、好ましくは、約５０〜５００ｐｐｍとなる量が添加される。 When the industrial preservative and fungicide of the present invention is used as described above, the active ingredient, that is, 2-bromo-2-nitro-1,3-propanediol, hydrophilicity represented by the following formula (1) Preferably, an amount of about 50 to 500 ppm is added so that the total amount of the isothiazoline compound and the hydrophobic isothiazoline compound represented by the following formula (2) is about 10 to 1000 ppm.
式（１）： Formula (1):
〔式中、Ｒ１は上述したものと同様である。〕 [Wherein, R 1 is the same as described above. ]
式（２）： Formula (2):
〔式中、Ｒ２は上述したものと同様である。〕 Wherein, R 2 is the same as that described above. ]
以下、本発明について、実施例を挙げてさらに具体的に説明する。本発明はこれらにより何ら限定されるものではない。なお、実施例等における評価は下記のようにして行った。 Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited by these. In addition, evaluation in an Example etc. was performed as follows.
なお、以下の実施例、比較例および試験結果の表に用いる有効成分の略号を下記に示す。 In addition, the symbol of the active ingredient used for the table | surface of a following example, a comparative example, and a test result is shown below.
ＢＮＰＤ：２−ブロモ−２−ニトロ−１，３−プロパンジオール
ＯＩＴ：２−ｎ−オクチル−４−イソチアゾリン−３−オン
ＤＥＧ：ジエチレングリコール
（１）工業用防腐防かび剤の調製
実施例１
ＤＥＧ６６．０重量％、ＭＩＴ含量５０重量％の水溶液４重量％およびＯＩＴ２重量％の混合液に、ＢＮＰＤ１５重量％を添加、室温（２５℃）で１時間撹拌して溶解した後、イオン交換水１３重量％を添加して透明溶液を得た。
BNPD: 2-bromo-2-nitro-1,3-propanediol OIT: 2-n-octyl-4-isothiazolin-3-one DEG: diethylene glycol (1) Preparation of industrial antiseptic and fungicide Example 1
15% by weight of BNPD was added to a mixed solution of 46.0% by weight of DEG 66.0% by weight, MIT content 50% by weight of aqueous solution and 2% by weight of OIT, and dissolved by stirring at room temperature (25 ° C.) for 1 hour. Weight percent was added to obtain a clear solution.
実施例２〜８
下記表１に示す割合の有効成分および溶媒から、実施例１と同様の操作により、実施例２〜８の各液剤をそれぞれ調製した。
Examples 2-8
From the active ingredients and solvents in the proportions shown in Table 1 below, each solution of Examples 2 to 8 was prepared in the same manner as in Example 1.
比較例１〜３
下記表１に示す割合の有効成分および溶媒から、実施例１と同様の操作により、比較例１〜３の各液剤をそれぞれ調製した。
Comparative Examples 1-3
From the active ingredients and solvents in the proportions shown in Table 1 below, each solution of Comparative Examples 1 to 3 was prepared in the same manner as in Example 1.
（２）最小発育阻止濃度（ＭＩＣ）試験
上記で調製した実施例１〜８の液剤および比較例１〜３について、ｐＨ６に調整されたグルコース−ブイヨン寒天培地を用いた倍数希釈法で、表２に示す供試菌を用い、細菌は３３℃で１８時間培養し、また、かびおよび酵母は３３℃で１８時間培養した後、２８℃で２日間培養し、それぞれの最小発育阻止濃度（ＭＩＣ：μｇ／ｍｌ）を求めた。その結果を表２に示す。
(2) Minimum Growth Inhibitory Concentration (MIC) Test Regarding the solutions of Examples 1 to 8 and Comparative Examples 1 to 3 prepared above, Table 2 shows a multiple dilution method using a glucose-bouillon agar medium adjusted to pH 6. Bacteria were cultured at 33 ° C. for 18 hours, and fungi and yeast were cultured at 33 ° C. for 18 hours and then cultured at 28 ° C. for 2 days. Each of the minimum growth inhibitory concentrations (MIC: μg / ml) was determined. The results are shown in Table 2.
（３）防腐効力試験
紙力剤（防腐剤添加品）に実施例１〜８および比較例１〜３の液剤を紙力剤中の濃度が０．０５重量％となるように添加した。腐敗種１％を添加して３３℃で培養し、１週間後に細菌はブイヨン培地にて、かび、酵母はグルコース−ブイヨン培地にて菌数を測定した。さらに、９日後に腐敗種を２％添加して３３℃で培養、試験開始より２週間後に菌数を測定した。同様に、１７日後に腐敗種を３％添加、試験開始より３週間後に菌数を測定した。その結果を表４に示す。なお前記腐敗種はＳｔａｐｈｙｌｏｃｏｃｃｕｓ ａｕｒｅｕｓ、Ｅｓｃｈｅｒｉｃｈｉａ ｃｏｌｉおよびＰｓｅｕｄｏｍｏｎａｓ ａｅｒｕｇｉｎｏｓａは各々のｏｐｕｔｉｃａｌ ｄｅｎｓｉｔｙ（６６０ｎｍ）を０．２、Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ、Ｐｅｎｉｃｉｌｌｉｕｍ ｃｉｔｒｉｎｕｍ、Ｃｌａｄｏｓｐｏｒｉｕｍ ｃｌａｄｏｓｐｏｒｉｏｉｄｅｓ、Ｓａｃｃｈａｒｏｍｙｃｅｓ ｃｅｒｅｖｉｓｉａｅおよびＲｈｏｄｏｔｏｒｕｌａは各々のｏｐｔｉｃａｌ ｄｅｎｓｉｔｙ（４２０ｎｍ）を０．２に調整後、すべての菌液を等量混合し、使用時に２倍希釈した。
(3) Preservative efficacy test The liquid agent of Examples 1-8 and Comparative Examples 1-3 was added to a paper strength agent (preservative addition product) so that the density | concentration in a paper strength agent might be 0.05 weight%. 1% of spoilage species was added and cultured at 33 ° C., and after 1 week, the number of bacteria was measured in a bouillon medium for bacteria and in a glucose-bouillon medium for yeast. Further, after 9 days, 2% of spoilage species was added and cultured at 33 ° C., and the number of bacteria was measured 2 weeks after the start of the test. Similarly, 3% of spoilage species was added after 17 days, and the number of bacteria was measured 3 weeks after the start of the test. The results are shown in Table 4. Note the rot species Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa 0.2 each oputical density (660nm), Aspergillus niger, Penicillium citrinum, Cladosporium cladosporioides, Saccharomyces cerevisiae and Rhodotorula are each optical density (420nm) 0. After adjusting to 2, all the bacterial solutions were mixed in equal amounts and diluted 2 times when used.
表３の結果から明らかなように、比較例１〜３の場合には、３３℃での培養２週間後には、細菌、かび、酵母の少なくともいずれかで菌種が検出され、腐敗が進行したことが確認された。これに対し、本発明の実施例１〜８では、３３℃での培養３週間後でも、細菌、かび、酵母のいずれについても菌種が検出されなかった。本防腐効力試験の結果、本発明の防腐防かび剤は、細菌、かび、酵母のいずれに対しても優れた腐敗防止効果を示す。 As is apparent from the results in Table 3, in the case of Comparative Examples 1 to 3, after 2 weeks of culturing at 33 ° C., the bacterial species was detected in at least one of bacteria, fungi, and yeast, and decay proceeded. It was confirmed. On the other hand, in Examples 1 to 8 of the present invention, no bacterial species were detected in any of bacteria, fungi, and yeast even after 3 weeks of culture at 33 ° C. As a result of this antiseptic efficacy test, the antiseptic / fungal agent of the present invention exhibits an excellent antiseptic effect against bacteria, fungi and yeasts.
Claims (5)
式（１）：
〔式中、Ｒ１はＣ１−３のアルキル基を示す。〕
式（２）：
〔式中、Ｒ２はＣ６−１２のアルキル基を示す。〕 It contains 2-bromo-2-nitro-1,3-propanediol, a hydrophilic isothiazoline compound represented by the following formula (1), a hydrophobic isothiazoline compound represented by the following formula (2), and a polar solvent. An industrial antiseptic and fungicidal agent.
Formula (1):
[Wherein, R 1 represents a C 1-3 alkyl group. ]
Formula (2):
[Wherein, R 2 represents a C 6-12 alkyl group. ]
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015502967A (en) * | 2011-12-23 | 2015-01-29 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Isothiazoline compounds for combating invertebrate pests |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02221205A (en) * | 1988-12-22 | 1990-09-04 | Rohm & Haas Co | Synergistically microbicidal compound drug containing 2-n-octyl-3-isothiazolone and commercially available certain kind of biocide |
| JPH0881311A (en) * | 1994-04-07 | 1996-03-26 | Rohm & Haas Co | Biocide containing no halogen |
| JP2001515016A (en) * | 1997-08-20 | 2001-09-18 | トール ヘミー ゲゼルシャフト ミット ベシュレンクテル ハフツング | Biolethal composition with synergistic action |
| US20020164266A1 (en) * | 2001-03-15 | 2002-11-07 | Peter Wachtler | Microbicidal mixtures |
| JP2003192507A (en) * | 2001-12-27 | 2003-07-09 | Takeda Chem Ind Ltd | Bactericidal composition for industrial use |
| JP2004507475A (en) * | 2000-08-31 | 2004-03-11 | トール ゲーエムベーハー | Synergistic biocide composition comprising 2-methylisothiazolin-3-one |
| JP2005068054A (en) * | 2003-08-22 | 2005-03-17 | Japan Enviro Chemicals Ltd | Industrial microbicidal composition |
| JP2005320320A (en) * | 2004-04-06 | 2005-11-17 | Japan Enviro Chemicals Ltd | Industrial sterilizing composition |
| JP2006001850A (en) * | 2004-06-16 | 2006-01-05 | Permachem Asia Ltd | Aqueous preservative |
| JP2006045246A (en) * | 2005-10-25 | 2006-02-16 | Somar Corp | Harmful microorganism exterminating agent |
-
2008
- 2008-07-23 JP JP2008190177A patent/JP5344862B2/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02221205A (en) * | 1988-12-22 | 1990-09-04 | Rohm & Haas Co | Synergistically microbicidal compound drug containing 2-n-octyl-3-isothiazolone and commercially available certain kind of biocide |
| JPH0881311A (en) * | 1994-04-07 | 1996-03-26 | Rohm & Haas Co | Biocide containing no halogen |
| JP2001515016A (en) * | 1997-08-20 | 2001-09-18 | トール ヘミー ゲゼルシャフト ミット ベシュレンクテル ハフツング | Biolethal composition with synergistic action |
| JP2004507475A (en) * | 2000-08-31 | 2004-03-11 | トール ゲーエムベーハー | Synergistic biocide composition comprising 2-methylisothiazolin-3-one |
| US20020164266A1 (en) * | 2001-03-15 | 2002-11-07 | Peter Wachtler | Microbicidal mixtures |
| JP2003192507A (en) * | 2001-12-27 | 2003-07-09 | Takeda Chem Ind Ltd | Bactericidal composition for industrial use |
| JP2005068054A (en) * | 2003-08-22 | 2005-03-17 | Japan Enviro Chemicals Ltd | Industrial microbicidal composition |
| JP2005320320A (en) * | 2004-04-06 | 2005-11-17 | Japan Enviro Chemicals Ltd | Industrial sterilizing composition |
| JP2006001850A (en) * | 2004-06-16 | 2006-01-05 | Permachem Asia Ltd | Aqueous preservative |
| JP2006045246A (en) * | 2005-10-25 | 2006-02-16 | Somar Corp | Harmful microorganism exterminating agent |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015502967A (en) * | 2011-12-23 | 2015-01-29 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Isothiazoline compounds for combating invertebrate pests |
| US9732051B2 (en) | 2011-12-23 | 2017-08-15 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
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