JP4060563B2 - Stabilized orthophthalaldehyde composition - Google Patents
Stabilized orthophthalaldehyde composition Download PDFInfo
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- JP4060563B2 JP4060563B2 JP2001318475A JP2001318475A JP4060563B2 JP 4060563 B2 JP4060563 B2 JP 4060563B2 JP 2001318475 A JP2001318475 A JP 2001318475A JP 2001318475 A JP2001318475 A JP 2001318475A JP 4060563 B2 JP4060563 B2 JP 4060563B2
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- orthophthalaldehyde
- lactic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/544—Diformyl benzenes; Alkylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
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- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、例えば製紙工業におけるスライム、各種工業用の冷却水や洗浄水、金属加工油剤、繊維油剤、塗工液などの防腐や殺菌用に有用な安定化されたオルトフタルアルデヒド組成物に関する。
【０００２】
【従来の技術】
従来、オルトフタルアルデヒドは防腐殺菌力に優れ、消毒薬あるいは防菌防腐剤の成分として有用であり、例えば、粉末やフレーク、あるいは蒸留された留分を直接容器に流し込み冷却固化させた固形物などがある。しかし粉末やフレーク状ではブロッキングしやすく、その粉砕の際に作業者が皮膚や粘膜に刺激を受ける欠点が有る。
【０００３】
このような観点から、オルトフタルアルデヒドは予め液状とすることが好ましく、各種の有機溶媒と混合した組成物が特許出願されている。例えば特開平８−１５７３０７号、特開平８−３０２５９４号、特開平９−１１０６１２号、特開平９−１１０６１６号、特開２０００−１７８２２２等が例示される。
【０００４】
【発明が解決しようとする課題】
しかしながら、ここで使用されている例えばプロピレンカーボネート、グリオキシム誘導体、又はその酸付加物、ジメチルアセトアミド、γ−ブチロラクトンなどは構造が複雑で、高価な化合物であったり、危険性あるいは有害性を有する化合物である。またジメチルアセトアミドやジメチルホルムアミドなどは殆どのプラスチック容器を浸蝕し、運搬や保管上問題となる。
【０００５】
一方、特開平１１−１４００１０号では水及び水溶性脂肪族アルコールを含有させたオルトフタルアルデヒド安定化組成物が記載されているが、水溶性脂肪族アルコールとしては、例えばグリコール系溶剤、グリコールエーテル系溶剤、アルコール系溶剤などが挙げられ、このうち前２者はコスト的にも高価であったり、危険性、有害性を有する化合物であり、アルコール系溶剤としては２−プロパノールや１−オクタノールが使用されているが、これらは揮発性を有したりあるいは危険性を有するものである。
また最近は環境汚染物質排出移動登録（ＰＲＴＲ）による化学物質の厳しい管理（環境保護及び企業化の観点）も視野に入れることも要求されている。
【０００６】
本発明の課題は、危険物質、有害物質等の規制に対応し、運搬や保管上の問題がなく、最近の環境汚染物質排出移動登録（ＰＲＴＲ）による化学物質の厳しい管理にも対応し得る、安全性が高く且つ優れた安定性を有するオルトフタルアルデヒド組成物を提供することにある。
【０００７】
【課題を解決するための手段】
本発明は、オルトフタルアルデヒド及び乳酸を含有する安定化されたオルトフタルアルデヒド組成物に係る。
また本発明は、オルトフタルアルデヒド、乳酸及び水を含有する安定化されたオルトフタルアルデヒド組成物に係る。
【０００８】
本発明において乳酸としては、例えばＤＬ−乳酸で述べれば引火点は１１０℃で何ら消防法による危険物でもなく、また食品にも添加される安全性に優れた化合物である。
一方、従来オルトフタルアルデヒドの安定化に使用されているジメチルホルムアミドやジメチルアセトアミドは引火点が６０〜６９℃であり、いずれも消防法上の引火性液体であり、アミン臭も若干あり、前者はＰＲＴＲ法で厳しく管理される化合物でもある。また、ジメチルアセトアミドやジメチルホルムアミド等はプラスチック等の樹脂を溶かす可能性があるため、使用する容器の材質や作業等に使用する器具等の選定にも制限が生じる。
【０００９】
ところで特開平６−２６４３９７号にはオルトフタルアルデヒドを有効成分とする製紙用スライム防除剤が、特開２０００−２９０１１２にはオルトフタルアルデヒド及び有機リン化合物を有効成分とする工業用抗菌剤組成物が記載され、いずれにおいても併用可能な有機溶剤の例の１つとして、乳酸エチルが挙げられている。しかし乳酸エチルは例えばＤＬ−乳酸エチルで述べれば引火点が５３℃で消防法上の引火性液体であり、また乳酸ほど安全性の高いものではない。
【００１０】
【発明の実施の形態】
本発明で用いられるオルトフタルアルデヒドは比較的低毒性の芳香族ジアルデヒドであって、公知の方法により、容易に製造することができる。また市販品としても入手可能であり、通常粉末またはフレーク状の形態である。
【００１１】
本発明で用いられる乳酸はＤ体、Ｌ体、ＤＬ体のいずれでも良く、また乳酸が縮合したラクチル乳酸、ジラクチル乳酸、トリラクチル乳酸等を含んだものであっても良い。使用する乳酸の濃度は特に限定されず、例えば０．１〜１００％のものを用いることができる。市販品としても容易に入手可能である。１００％の乳酸は固体状であり、通常は９０％以下の液状のものが使用に便利である。しかしＤＬ−乳酸は融点が１８℃であるので２５℃程度の室温では液状である。乳酸は原則的にはオルトフタルアルデヒドの溶媒として機能するが、水酸基やカルボキシル基を有するので、一部反応に関与している可能性もあるが、そのようなものも含まれる。本発明では上記乳酸以外に、さらに水を含んでいても良い。
【００１２】
本発明においてオルトフタルアルデヒドの組成物中における割合は０.１〜７０重量％、より好ましくは１０〜４０重量％である。
本発明において乳酸の組成物中における割合は０.１〜９９重量％、より好ましくは４０〜７２重量％である。
【００１３】
本発明において水の割合は０〜９９重量％、より好ましくは６〜４０重量％である。本発明の安定化されたオルトフタルアルデヒド組成物は、水の含有量に依存するが、通常、水の含有量が６〜４０重量％のときは氷点下でも凍結せず寒冷地での取り扱い、作業性に優れたものとなる
【００１４】
本発明では本発明の目的を妨げない範囲で、アミド類、アルコール類、エーテル類、エステル類、ケトン類等を併用することもできる。
アミド類としては、例えばジメチルホルムアミドやジメチルアセトアミドなど、アルコール類としては、例えばエチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、ポリエチレングリコールなどのグリコール類、炭素数８までのアルコール類など、エーテル類としては、例えばメチルセロソルブ、フェニルセロソルブ、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノメチルエーテル、１,２−ジブトキシエタン、ジオキサン、テトラヒドロフランなど、エステル類としては、例えばメチルアセテート、エチルアセテート、ブチルアセテート、マレイン酸ジメチル、アジピン酸ジエチル、乳酸エチル、グルタル酸ジメチル、コハク酸ジメチル、フタル酸ジメチル、３−メトキシブチルアセテート、３−メトキシブチルアセテート、２−エトキシメチルアセテート、２−エトキシエチルアセテート、プロピレンカーボネ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−ペンタンジオールイソブチレートなど、ケトン類としては、例えばアセトン、メチルエチルケトン、メチルイソブチルケトン、イソホロンなどを挙げることができる。
【００１５】
本発明では本発明の目的を妨げない範囲で更に分散剤、界面活性剤、増粘剤、防錆剤、オルトフタルアルデヒド（以下、ＯＰＡＬという）以外の殺菌、制菌剤などを併用することもできる。
【００１６】
本発明においては、オルトフタルアルデヒド、乳酸および必要に応じて水、有機溶剤、添加剤等を混合することにより目的とする組成物を得ることができる。混合は通常、攪拌装置の付いたタンクなどを使用することができる。
本発明の安定化されたオルトフタルアルデヒド組成物は、例えば製紙工業におけるスライム、各種工業用の冷却水や洗浄水、金属加工油剤、繊維油剤、塗工液などの防腐や殺菌用に用いることができる。
【００１７】
【実施例】
以下に実施例および試験例を挙げて本発明を具体的に説明するが、何らこれに限定されるものではない。
【００１８】
実施例１〜７
表１に示した配合によりＯＰＡＬ、乳酸の含水物とを混合、攪拌し均一な安定性に優れた溶液を得た。
【００１９】
試験例１
実施例１〜７の組成物を−１０℃、１０日間保存し、凍結の有無等外観を観察した。組成物の組成及び１０日後の外観を表２に示した。
【００２０】
【表１】
【表２】
【発明の効果】
本発明の安定化されたオルトフタルアルデヒド組成物は、使用する乳酸が食品添加剤として用いられるほど安全性に優れたものであり、危険物質、有害物質等の規制に対応し、運搬や保管上の問題がなく、最近の環境汚染物質排出移動登録（ＰＲＴＲ）による化学物質の厳しい管理にも対応し得る、安全性が高く且つ優れた安定性を有するという顕著な効果を奏する。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a stabilized orthophthalaldehyde composition useful for antiseptic and sterilization of, for example, slime in the paper industry, various industrial cooling waters and washing waters, metal processing oils, fiber oils, coating liquids and the like.
[0002]
[Prior art]
Conventionally, orthophthalaldehyde has excellent antiseptic sterilizing power and is useful as a component of disinfectant or antiseptic preservative. For example, powders, flakes, or solids obtained by pouring distilled fractions directly into containers and solidifying by cooling. There is. However, powders and flakes are easy to block, and there is a drawback that the worker is irritated by the skin and mucous membranes during pulverization.
[0003]
From such a viewpoint, it is preferable that orthophthalaldehyde is in a liquid state in advance, and patent applications have been made for compositions mixed with various organic solvents. Examples thereof include JP-A-8-157307, JP-A-8-302594, JP-A-9-110612, JP-A-9-110616, and JP-A-2000-178222.
[0004]
[Problems to be solved by the invention]
However, for example, propylene carbonate, glyoxime derivatives, or acid adducts thereof, dimethylacetamide, γ-butyrolactone, etc. used here are complicated in structure, expensive compounds, and compounds that are dangerous or harmful. is there. Also, dimethylacetamide, dimethylformamide, and the like erode most plastic containers, causing problems in transportation and storage.
[0005]
On the other hand, JP-A-11-140010 discloses an orthophthalaldehyde stabilizing composition containing water and a water-soluble aliphatic alcohol. Examples of the water-soluble aliphatic alcohol include glycol solvents and glycol ethers. Solvents, alcohol solvents, etc. are mentioned. Among them, the former two are expensive, dangerous and harmful compounds, and 2-propanol and 1-octanol are used as alcohol solvents. However, they are volatile or dangerous.
Recently, it is also required to take into account the strict management of chemical substances (from the viewpoint of environmental protection and commercialization) by the Environmental Pollutant Release Transfer Registration (PRTR).
[0006]
The problem of the present invention corresponds to the regulation of dangerous substances, harmful substances, etc., there is no problem in transportation and storage, and can correspond to the strict management of chemical substances by recent environmental pollutant discharge transfer registration (PRTR), An object of the present invention is to provide an orthophthalaldehyde composition having high safety and excellent stability.
[0007]
[Means for Solving the Problems]
The present invention relates to a stabilized orthophthalaldehyde composition containing orthophthalaldehyde and lactic acid.
The invention also relates to a stabilized orthophthalaldehyde composition containing orthophthalaldehyde, lactic acid and water.
[0008]
In the present invention, as lactic acid, for example, DL-lactic acid is a compound having a flash point of 110 ° C., which is not a dangerous substance by the Fire Service Act, and excellent in safety added to foods.
On the other hand, dimethylformamide and dimethylacetamide, which are conventionally used for stabilizing orthophthalaldehyde, have a flash point of 60 to 69 ° C., both of which are flammable liquids under the Fire Service Act and have a slight amine odor. It is also a compound strictly controlled by the PRTR method. In addition, since dimethylacetamide, dimethylformamide, and the like may dissolve a resin such as plastic, there is a limit to the selection of the material of the container to be used and the equipment to be used for work.
[0009]
JP-A-6-264297 discloses a slime control agent for paper making containing orthophthalaldehyde as an active ingredient, and JP-A 2000-290112 discloses an industrial antibacterial agent composition containing orthophthalaldehyde and an organophosphorus compound as active ingredients. One example of an organic solvent that is described and can be used in combination is ethyl lactate. However, ethyl lactate is, for example, DL-ethyl lactate, and has a flash point of 53 ° C. and is a flammable liquid according to the Fire Service Act, and is not as safe as lactic acid.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
The orthophthalaldehyde used in the present invention is an aromatic dialdehyde having a relatively low toxicity and can be easily produced by a known method. It is also available as a commercial product and is usually in the form of powder or flakes.
[0011]
The lactic acid used in the present invention may be any of D-form, L-form and DL-form, and may contain lactyl lactic acid, dilacty lactic acid, trilacty lactic acid etc. condensed with lactic acid. The density | concentration of the lactic acid to be used is not specifically limited, For example, a 0.1-100% thing can be used. It can be easily obtained as a commercial product. 100% lactic acid is in a solid state, and usually 90% or less liquid is convenient for use. However, since DL-lactic acid has a melting point of 18 ° C., it is liquid at room temperature of about 25 ° C. Lactic acid functions in principle as a solvent for orthophthalaldehyde, but since it has a hydroxyl group or a carboxyl group, it may be partly involved in the reaction, but such is also included. In the present invention, water may be further contained in addition to the lactic acid.
[0012]
In the present invention, the proportion of orthophthalaldehyde in the composition is 0.1 to 70% by weight, more preferably 10 to 40% by weight.
In the present invention, the proportion of lactic acid in the composition is 0.1 to 99% by weight, more preferably 40 to 72% by weight.
[0013]
In the present invention, the proportion of water is 0 to 99% by weight, more preferably 6 to 40% by weight. The stabilized orthophthalaldehyde composition of the present invention depends on the water content, but usually, when the water content is 6 to 40% by weight, it is not frozen even at freezing point and is handled and operated in a cold region. It will have excellent properties. [0014]
In the present invention, amides, alcohols, ethers, esters, ketones and the like can be used in combination as long as the object of the present invention is not impaired.
Examples of amides include dimethylformamide and dimethylacetamide. Examples of alcohols include glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, and polyethylene glycol, and alcohols having up to 8 carbon atoms such as ethers. Is, for example, methyl cellosolve, phenyl cellosolve, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether, 1,2-dibutoxyethane, dioxane, tetrahydrofuran, etc. Examples of esters include methyl acetate, ethyl acetate, Butyl acetate, dimethyl maleate, diethyl adipate, ethyl lactate, dimethyl glutarate , Dimethyl succinate, dimethyl phthalate, 3-methoxybutyl acetate, 3-methoxybutyl acetate, 2-ethoxymethyl acetate, 2-ethoxyethyl acetate, propylene carbonate ethylene glycol diacetate, 2,2,4-trimethyl-1 Examples of ketones such as 1,3-pentanediol isobutyrate include acetone, methyl ethyl ketone, methyl isobutyl ketone, and isophorone.
[0015]
In the present invention, a dispersant, a surfactant, a thickener, a rust inhibitor, a bactericidal agent or an antibacterial agent other than orthophthalaldehyde (hereinafter referred to as OPAL) may be used in combination as long as the object of the present invention is not impaired. it can.
[0016]
In the present invention, a desired composition can be obtained by mixing orthophthalaldehyde, lactic acid and, if necessary, water, an organic solvent, an additive and the like. For mixing, a tank equipped with a stirrer can be used.
The stabilized orthophthalaldehyde composition of the present invention can be used for antiseptic and sterilization of slime in the paper industry, various industrial cooling waters and washing waters, metalworking oils, fiber oils, coating liquids, etc. it can.
[0017]
【Example】
EXAMPLES The present invention will be specifically described below with reference to examples and test examples, but the present invention is not limited to these examples.
[0018]
Examples 1-7
According to the formulation shown in Table 1, OPAL and a hydrated product of lactic acid were mixed and stirred to obtain a solution having excellent uniform stability.
[0019]
Test example 1
The compositions of Examples 1 to 7 were stored at −10 ° C. for 10 days, and appearances such as the presence or absence of freezing were observed. The composition of the composition and the appearance after 10 days are shown in Table 2.
[0020]
[Table 1]
[Table 2]
【The invention's effect】
The stabilized orthophthalaldehyde composition of the present invention is so safe that the lactic acid used is used as a food additive, complying with regulations on dangerous substances, harmful substances, etc., for transportation and storage. There is no problem, and there is a remarkable effect of having high safety and excellent stability that can cope with strict management of chemical substances by the recent environmental pollutant discharge transfer registration (PRTR).
Claims (4)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001318475A JP4060563B2 (en) | 2001-10-16 | 2001-10-16 | Stabilized orthophthalaldehyde composition |
| PCT/JP2002/010727 WO2003033446A1 (en) | 2001-10-16 | 2002-10-16 | STABILIZED o-PHTHALALDEHYDE COMPOSITIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001318475A JP4060563B2 (en) | 2001-10-16 | 2001-10-16 | Stabilized orthophthalaldehyde composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003128505A JP2003128505A (en) | 2003-05-08 |
| JP4060563B2 true JP4060563B2 (en) | 2008-03-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001318475A Expired - Fee Related JP4060563B2 (en) | 2001-10-16 | 2001-10-16 | Stabilized orthophthalaldehyde composition |
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| Country | Link |
|---|---|
| JP (1) | JP4060563B2 (en) |
| WO (1) | WO2003033446A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2008115141A (en) * | 2006-11-08 | 2008-05-22 | K I Chemical Industry Co Ltd | Amoeba killing agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06264397A (en) * | 1993-03-08 | 1994-09-20 | Permachem Asia Ltd | Slime controlling agent for papermaking |
| JP3445406B2 (en) * | 1995-05-11 | 2003-09-08 | 株式会社パーマケム・アジア | Slime control agent for papermaking |
| JP3778222B2 (en) * | 1996-01-22 | 2006-05-24 | 栗田工業株式会社 | Orthophthalaldehyde stabilization solution |
| JP4090544B2 (en) * | 1997-11-11 | 2008-05-28 | ケイ・アイ化成株式会社 | Orthophthalaldehyde stabilizing composition |
| JP4344031B2 (en) * | 1998-12-16 | 2009-10-14 | ケイ・アイ化成株式会社 | Orthophthalaldehyde stabilizing composition and method for producing the same |
-
2001
- 2001-10-16 JP JP2001318475A patent/JP4060563B2/en not_active Expired - Fee Related
-
2002
- 2002-10-16 WO PCT/JP2002/010727 patent/WO2003033446A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003033446A1 (en) | 2003-04-24 |
| JP2003128505A (en) | 2003-05-08 |
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