JPH09194419A - Stabilized solution of ortho-phthalaldehyde - Google Patents
Stabilized solution of ortho-phthalaldehydeInfo
- Publication number
- JPH09194419A JPH09194419A JP873696A JP873696A JPH09194419A JP H09194419 A JPH09194419 A JP H09194419A JP 873696 A JP873696 A JP 873696A JP 873696 A JP873696 A JP 873696A JP H09194419 A JPH09194419 A JP H09194419A
- Authority
- JP
- Japan
- Prior art keywords
- solution
- orthophthalaldehyde
- formula
- solvent
- phthalaldehyde
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paper (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、オルソフタルアル
デヒドの安定化溶液に関する。FIELD OF THE INVENTION The present invention relates to a stabilizing solution of orthophthalaldehyde.
【０００２】[0002]
【従来の技術】オルソフタルアルデヒドは、抗菌性を有
し、防菌剤あるいは殺菌剤等として有害微生物の増繁殖
が問題となる各種の分野に用いられている。例えば、紙
パルプ工業分野における用水や冷却用循環水、紙用塗工
液、または水性塗料等に対する殺菌剤あるいは防菌剤と
して用いられる（特開平６−２３３６８号公報、特開平
６−２６４３９７号、特開平７−１１６６６９号公報等
参照）。BACKGROUND OF THE INVENTION Orthophthalaldehyde has antibacterial properties and is used as various antibacterial agents or bactericides in various fields in which the proliferation of harmful microorganisms is a problem. For example, it is used as a bactericidal agent or bactericidal agent for water for use in the pulp and paper industry, circulating water for cooling, coating liquid for paper, water-based paint, etc. See Japanese Patent Laid-Open No. 7-116669.
【０００３】かかるオルソフタルアルデヒドは、一般に
は溶液として使用され、オルソフタルアルデヒドの溶液
調製に使用される溶媒としては、従来より次の化合物が
知られている。例えば、特開平６−２３３６８号公報に
は、エチレングリコール等のグリコール類、メタノー
ル、エタノール等のアルコール類、テトラヒドロフラン
等が挙げられている。また、特開平６−２６４３９７号
公報には、さらに、ベンゼン、トルエン、キシレン等の
芳香族炭化水素、酢酸エチル、酢酸ブチル、アジピン酸
エチル、乳酸エチル等のエステル類、ジメチルアセトア
ミド、ジメチルホルムアミド、ジメチルスルホキシド、
ジオキサン、マレイン酸ジメチル等が挙げられている。
また、特開平７−１１６６６９号公報には、さらに、ア
セトン、メチルエチルケトン、メチルイソブチルケト
ン、イソホロン等のケトン類が挙げられている。Such orthophthalaldehyde is generally used as a solution, and as a solvent used for preparing a solution of orthophthalaldehyde, the following compounds have been conventionally known. For example, JP-A-6-23368 discloses glycols such as ethylene glycol, alcohols such as methanol and ethanol, tetrahydrofuran and the like. Further, in JP-A-6-264397, aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl acetate, butyl acetate, ethyl adipate and ethyl lactate, dimethylacetamide, dimethylformamide and dimethyl are further disclosed. Sulfoxide,
Dioxane, dimethyl maleate and the like are mentioned.
Further, JP-A-7-116669 further lists ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and isophorone.
【０００４】[0004]
【発明が解決しようとする課題】しかし、オルソフタル
アルデヒドは不安定な化合物であるため、分解によって
溶液中の濃度が低下したり、求核性が強い溶媒と反応し
て不活性化したりするという問題がある。従って、上述
した従来の溶媒は、長期間安定な溶液を調製するための
溶媒としては実用上必ずしも充分ではなかった。However, since orthophthalaldehyde is an unstable compound, its concentration in the solution is lowered by decomposition, and it is inactivated by reacting with a strongly nucleophilic solvent. There's a problem. Therefore, the above-mentioned conventional solvent is not always practically sufficient as a solvent for preparing a stable solution for a long period of time.
【０００５】本発明は、このような事情に鑑み、オルソ
フタルアルデヒド溶液における上述した問題を解決し、
安定化されたオルソフタルアルデヒド溶液を提供するこ
とを課題とする。In view of such circumstances, the present invention solves the above-mentioned problems in an orthophthalaldehyde solution,
An object is to provide a stabilized orthophthalaldehyde solution.
【０００６】[0006]
【課題を解決するための手段】前記課題を解決する本発
明の第１の態様は、オルソフタルアルデヒドを、下記式
（Ｉ）で示されるグルタル酸ジアルキル、下記式（II）
で示されるコハク酸ジアルキルおよび下記式（III）で
示されるプロピレンカーボネートからなる群から選択さ
れる少なくとも一種の溶媒またはこれらを主成分とする
溶媒に溶解させてなることを特徴とするオルソフタルア
ルデヒドの安定化溶液にある。The first aspect of the present invention for solving the above-mentioned problems is to use orthophthalaldehyde as the dialkyl glutarate represented by the following formula (I) and the following formula (II).
Of orthophthalaldehyde characterized by being dissolved in at least one solvent selected from the group consisting of dialkyl succinate represented by and propylene carbonate represented by the following formula (III) or a solvent containing these as the main components. In stabilizing solution.
【０００７】[0007]
【化３】 ここで、Ｒ1〜Ｒ4は、それぞれ炭素数１〜３の低級アル
キル基である。Embedded image Here, R 1 to R 4 are lower alkyl groups having 1 to 3 carbon atoms, respectively.
【０００８】[0008]
【化４】 Embedded image
【０００９】すなわち、本発明によれば、上述したグル
タル酸ジアルキル、コハク酸ジアルキルおよびプロピレ
ンカーボネートからなる群から選択される少なくとも一
種を含む溶媒を用いることにより、オルソフタルアルデ
ヒドの分解が著しく抑制され、安定性が非常に高められ
たオルソアルデヒド溶液が提供される。That is, according to the present invention, by using a solvent containing at least one selected from the group consisting of the above-mentioned dialkyl glutarate, dialkyl succinate and propylene carbonate, the decomposition of orthophthalaldehyde is significantly suppressed, An orthoaldehyde solution with greatly enhanced stability is provided.
【００１０】ここで、オルソフタルアルデヒドは、下記
式（IV）で示される化合物である。Here, orthophthalaldehyde is a compound represented by the following formula (IV).
【００１１】[0011]
【化５】 Embedded image
【００１２】本発明の安定化オルソフタルアルデヒド溶
液は、かかるオルソフタルアルデヒドを上述したグルタ
ル酸ジアルキルおよびコハク酸ジアルキルからなる群か
ら選択される少なくとも一種、またはプロピレンカーボ
ネートを含む溶媒に溶解することにより得ることができ
る。グルタル酸ジアルキルおよびコハク酸ジアルキルま
たはプロピレンカーボネートは、それぞれ単独で用いて
も複数のものを任意の割合で混合して用いてもよい。ま
た、これらの単独あるいは混合溶媒に、例えば、メタネ
ール、エタノール、プロパノール等のアルコール類；エ
チレングリコール、ジエチレングリコール、プロピレン
グリコール、ポエチレングリコール、エチルセロソル
ブ、ジ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アセテート、３−メト
キシブチルアセテート、エチレングリコールジアセテー
ト、２，２，４−トリメチル−１，３−ペンタンジオー
ルジイソブチレート等のグリコール系溶媒；酢酸エチ
ル、酢酸ブチル、マレイン酸ジメチル、アジピン酸ジエ
チル、乳酸エチル等のエステル類；アセトン、メチルエ
チルケトン、メチルイソブチルケトン、イソホロン等の
ケトン類；トルエン、キシレン、１，２−ジメチル−４
−エチルベンゼン等の芳香族系溶媒；ジメチルアセトア
ミド、ジメチルホルムアミド、ジメチルスルホキシド、
ジオキサンなどの他の溶媒を混合して用いることもでき
る。但し、この場合には、全溶媒中のグルタル酸ジアル
キル、コハク酸ジアルキルおよびプロピレンカーボネー
トから選択された溶媒の合計の組成が５０重量％以上で
あることが望ましい。The stabilized orthophthalaldehyde solution of the present invention is obtained by dissolving such orthophthalaldehyde in a solvent containing at least one selected from the group consisting of dialkyl glutarate and dialkyl succinate, or propylene carbonate. be able to. The dialkyl glutarate and the dialkyl succinate or propylene carbonate may be used alone or as a mixture of two or more at an arbitrary ratio. Further, these alone or in a mixed solvent, for example, alcohols such as methanol, ethanol, propanol; ethylene glycol, diethylene glycol, propylene glycol, polyethylene glycol, ethyl cellosolve, diethylene glycol monomethyl ether, ethylene glycol monoethyl ether acetate, 3- Glycol solvents such as methoxybutyl acetate, ethylene glycol diacetate, 2,2,4-trimethyl-1,3-pentanediol diisobutyrate; ethyl acetate, butyl acetate, dimethyl maleate, diethyl adipate, ethyl lactate, etc. Esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone; toluene, xylene, 1,2-dimethyl-4
-Aromatic solvents such as ethylbenzene; dimethylacetamide, dimethylformamide, dimethylsulfoxide,
Other solvents such as dioxane can also be mixed and used. However, in this case, it is desirable that the total composition of the solvents selected from dialkyl glutarate, dialkyl succinate and propylene carbonate in all the solvents is 50% by weight or more.
【００１３】また、本発明のオルソフタルアルデヒド溶
液には、これに可溶性の他種殺菌剤あるいは防菌剤を溶
解して使用することができる。In the orthophthalaldehyde solution of the present invention, other soluble bactericides or antibacterial agents can be dissolved and used.
【００１４】[0014]
【発明の実施の形態】以下、本発明をさらに詳細に説明
する。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail.
【００１５】（試験例）オルソアルデヒドを、各種有機
溶媒に溶解して試料溶液Ｎｏ．１〜２２を調製した。各
試料溶液の組成は表１に示した。ここで、試料溶液Ｎ
ｏ．１〜１０が本発明の実施例に係り、Ｎｏ．１１〜２
２が比較例である。(Test Example) Orthoaldehyde was dissolved in various organic solvents to prepare a sample solution No. 1-22 were prepared. The composition of each sample solution is shown in Table 1. Here, the sample solution N
o. Nos. 1 to 10 relate to the embodiment of the present invention. 11-2
2 is a comparative example.
【００１６】[0016]
【表１】 [Table 1]
【００１７】次に、各試料溶液を恒温室（４０℃）に保
管し、経時的に各試料溶液の一部をそれぞれ採取して液
体クロマトグラフィーでオルソフタルアルデヒドの残存
濃度を測定した。この結果を残存率（％）として表２に
示した。なお、残存率は次式で示される。Next, each sample solution was stored in a temperature-controlled room (40 ° C.), and a part of each sample solution was sampled over time to measure the residual concentration of orthophthalaldehyde by liquid chromatography. The results are shown in Table 2 as the residual rate (%). The residual rate is expressed by the following equation.
【００１８】残存率（％）＝（Ｂ／Ａ）×１００ Ａ・・・オルソフタルアルデヒドの初期濃度 Ｂ・・・オルソフタルアルデヒドの測定濃度Residual rate (%) = (B / A) × 100 A ... Initial concentration of orthophthalaldehyde B ... Measured concentration of orthophthalaldehyde
【００１９】[0019]
【表２】 [Table 2]
【００２０】表２に示される結果から明らかなように、
比較例に係る試料溶液Ｎｏ．１１〜２２は、オルソフタ
ルアルデヒドが３０日以上安定なものはなかった。これ
に対し、本発明によれば、グルタル酸ジアルキルまたは
コハク酸ジアルキルから選ばれる溶媒をそれぞれ単独で
用いた試料溶液Ｎｏ．１〜４および１０、およびこれら
を混合して用いた試料溶液Ｎｏ．５〜７、さらに、これ
らの溶媒の単独または混合物に他種溶媒を混合して用い
た試料溶媒Ｎｏ．８および９は、何れもオルソフタルア
ルデヒドが３０日以上にわたって安定であった。As is clear from the results shown in Table 2,
Sample solution No. 1 according to the comparative example. No. 11 to 22 had orthophthalaldehyde stable for 30 days or longer. On the other hand, according to the present invention, sample solution No. 1 using a solvent selected from dialkyl glutarate or dialkyl succinate, respectively. Sample solutions Nos. 1 to 4 and 10 and sample solutions Nos. 5 to 7, and sample solvent Nos. 1 and 2 which were used alone or as a mixture of these solvents with another solvent. In all of 8 and 9, orthophthalaldehyde was stable for 30 days or longer.
【００２１】[0021]
【発明の効果】以上説明したように、本発明に係るオル
ソフタルアルデヒド溶液は、オルソフタルアルデヒドの
分解が著しく抑制され、安定性が非常に高められたもの
である。従って、本発明に係るオルソフタルアルデヒド
溶液は、その安定性が高いことから、その保存および輸
送等を有利に行うことができ、オルソフタルアルデヒド
を含む殺菌剤あるいは防菌剤の製造原料として、または
そのまま殺菌剤あるいは防菌剤として好適である。As described above, the orthophthalaldehyde solution according to the present invention is a solution in which the decomposition of orthophthalaldehyde is significantly suppressed and the stability is greatly enhanced. Therefore, since the orthophthalaldehyde solution according to the present invention has high stability, it can be advantageously stored and transported, and can be used as a raw material for producing a bactericide or antibacterial agent containing orthophthalaldehyde, or It is suitable as it is as a bactericide or antibacterial agent.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ａ０１Ｎ 35/04 Ａ０１Ｎ 35/04 ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 6 Identification code Office reference number FI technical display location // A01N 35/04 A01N 35/04
Claims (2)
（Ｉ）で示されるグルタル酸ジアルキル、下記式（II）
で示されるコハク酸ジアルキルおよび下記式（III）で
示されるプロピレンカーボネートからなる群から選択さ
れる少なくとも一種の溶媒またはこれらを主成分とする
溶媒に溶解させてなることを特徴とするオルソフタルア
ルデヒドの安定化溶液。 【化１】 ここで、Ｒ1〜Ｒ4は、それぞれ炭素数１〜３の低級アル
キル基である。 【化２】 1. An orthophthalaldehyde is a dialkyl glutarate represented by the following formula (I) and a following formula (II):
Of orthophthalaldehyde characterized by being dissolved in at least one solvent selected from the group consisting of dialkyl succinate represented by and propylene carbonate represented by the following formula (III) or a solvent containing these as the main components. Stabilizing solution. Embedded image Here, R 1 to R 4 are lower alkyl groups having 1 to 3 carbon atoms, respectively. Embedded image
ルタル酸ジアルキル、コハク酸ジアルキル、およびプロ
ピレンカーボネートから選択された溶媒の合計が、５０
重量％以上であることを特徴とするオルソフタルアルデ
ヒドの安定化溶液。2. The total amount of the solvent selected from the dialkyl glutarate, the dialkyl succinate, and propylene carbonate in the solvent according to claim 1, is 50 or more.
A stabilized solution of orthophthalaldehyde, characterized in that it is at least wt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00873696A JP3778222B2 (en) | 1996-01-22 | 1996-01-22 | Orthophthalaldehyde stabilization solution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00873696A JP3778222B2 (en) | 1996-01-22 | 1996-01-22 | Orthophthalaldehyde stabilization solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09194419A true JPH09194419A (en) | 1997-07-29 |
| JP3778222B2 JP3778222B2 (en) | 2006-05-24 |
Family
ID=11701245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP00873696A Expired - Fee Related JP3778222B2 (en) | 1996-01-22 | 1996-01-22 | Orthophthalaldehyde stabilization solution |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3778222B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003033446A1 (en) * | 2001-10-16 | 2003-04-24 | Showa Kako Corporation | STABILIZED o-PHTHALALDEHYDE COMPOSITIONS |
| WO2003073849A1 (en) * | 2002-02-28 | 2003-09-12 | Ecolab Inc. | Diester dicarboxylate antimicrobial compositions and methods employing them |
| JP2009154154A (en) * | 1998-03-16 | 2009-07-16 | Nalco Chem Co | Contaminant dispersant useful in recycling of treated container |
-
1996
- 1996-01-22 JP JP00873696A patent/JP3778222B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009154154A (en) * | 1998-03-16 | 2009-07-16 | Nalco Chem Co | Contaminant dispersant useful in recycling of treated container |
| WO2003033446A1 (en) * | 2001-10-16 | 2003-04-24 | Showa Kako Corporation | STABILIZED o-PHTHALALDEHYDE COMPOSITIONS |
| WO2003073849A1 (en) * | 2002-02-28 | 2003-09-12 | Ecolab Inc. | Diester dicarboxylate antimicrobial compositions and methods employing them |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3778222B2 (en) | 2006-05-24 |
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