JP7353075B2 - Deodorizing structure - Google Patents
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Description
本発明は、アセトアルデヒドやホルムアルデヒド等のアルデヒド類の捕捉に有効な消臭性構造物に関する。 The present invention relates to a deodorizing structure that is effective in capturing aldehydes such as acetaldehyde and formaldehyde.
アセトアルデヒドやホルムアルデヒド等のアルデヒド類は、生活環境における代表的な臭気物質であり、臭い閾値が極めて低いために低濃度でも不快臭の原因となる。これらのアルデヒド類は屋内や自動車内において合成樹脂、合板、タバコの煙等から発生し、シックハウス症候群やシックカー症候群の原因となることが知られている。また、これらのアルデヒド類は発癌性も疑われており、人が日常的にこれらに曝されると、健康を害するリスクがある。そのため、厚生労働省により室内濃度指針値として、アセトアルデヒドは０．０３ｐｐｍ、ホルムアルデヒドは０．０８ｐｐｍと規定されている。したがって、アルデヒド類を速やかに且つ持続的に除去する手段が求められている。 Aldehydes such as acetaldehyde and formaldehyde are typical odor substances in the living environment, and because they have extremely low odor thresholds, they cause unpleasant odors even at low concentrations. These aldehydes are generated from synthetic resins, plywood, cigarette smoke, etc. indoors and in automobiles, and are known to cause sick building syndrome and sick car syndrome. Furthermore, these aldehydes are also suspected of being carcinogenic, and there is a risk of harm to human health if people are exposed to them on a daily basis. Therefore, the Ministry of Health, Labor and Welfare defines the indoor concentration guideline values as 0.03 ppm for acetaldehyde and 0.08 ppm for formaldehyde. Therefore, there is a need for a means to quickly and sustainably remove aldehydes.
アセトアルデヒドやホルムアルデヒド等の低級アルデヒドは沸点が低いため、消臭剤として汎用されるシリカゲルや活性炭等の無機系多孔質材では捕捉効率が低い。そこで、ヒドラジン誘導体、アミン、アミノ酸、又は尿素誘導体等からなるアルデヒド捕捉剤とアルデヒド類を化学反応させることによりアルデヒド類を捕捉する方法が開示されている（例えば、特許文献１～３参照）。 Lower aldehydes such as acetaldehyde and formaldehyde have low boiling points, so inorganic porous materials such as silica gel and activated carbon, which are commonly used as deodorants, have low capture efficiency. Therefore, methods for capturing aldehydes by chemically reacting aldehydes with aldehyde scavengers made of hydrazine derivatives, amines, amino acids, urea derivatives, etc. have been disclosed (see, for example, Patent Documents 1 to 3).
しかしながら、これら特許文献に記載の方法は、捕捉効率が不十分である、捕捉剤自体が臭気源となる、又は一旦アルデヒド類を捕捉しても経時的にアルデヒド類を再放出する等の問題があった。また、これら特許文献に記載のアルデヒドの捕捉剤をシックハウス症候群やシックカー症候群を予防する目的で住居内や自動車内で使用する場合、これらの場所は夏場等に高温になるため、性能が低下する点が問題であった。 However, the methods described in these patent documents have problems such as insufficient capture efficiency, the scavenger itself becoming a source of odor, or even if aldehydes are once captured, they are re-released over time. there were. In addition, when using the aldehyde scavengers described in these patent documents in homes or cars for the purpose of preventing sick building syndrome or sick car syndrome, performance may deteriorate as these areas become hot in the summer. was the problem.
本発明はかかる従来技術の背景に鑑み、アルデヒドとの接触時に、優れた捕捉効果を示す消臭性構造物を提供することをその目的とする。 In view of the background of the prior art, an object of the present invention is to provide a deodorizing structure that exhibits an excellent trapping effect when it comes into contact with aldehydes.
本発明者らは、上記の課題を解決するため鋭意検討を重ねた結果、特定のＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩を１種以上含有することを特徴とする消臭性構造物がアルデヒド類を速やかに且つ持続的に捕捉することを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors have developed a deodorizing product characterized by containing one or more specific O-substituted hydroxylamine derivatives or chemically acceptable salts thereof. The present inventors have discovered that the chemical structure rapidly and sustainably captures aldehydes, and have completed the present invention.
すなわち、本発明は、以下の要旨を有するものである。
［１］
下記一般式（１）で表されるＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩を１種以上含有することを特徴とする消臭性構造物。
That is, the present invention has the following gist.
[1]
A deodorizing structure characterized by containing one or more O-substituted hydroxylamine derivatives represented by the following general formula (1) or chemically acceptable salts thereof.
（式中、Ｒは水素原子又は炭素数１～４のアルキル基を表す。ｎは１～６の整数を表す。複数のＲは同一又は相異なっていてもよい。）
［２］
前記一般式（１）で表されるＯ－置換ヒドロキシルアミン誘導体において、Ｒが水素原子であり、ｎが１～４の整数であるＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩を１種以上含有することを特徴とする［１］に記載の消臭性構造物。
［３］
構造物の基材が、繊維状物、シート状物、スポンジ状物、ボード状物であることを特徴とする［１］又は［２］に記載の消臭性構造物。
［４］
構造物の基材が、合成繊維、半合成繊維、天然繊維、ガラス繊維、炭素繊維、セラミックス繊維及びこれらの混合繊維からなる織物、編物、不織布、糸、ロープ、紐状の繊維状物；樹脂、天然ゴム、合成ゴムからなるシート状物やスポンジ状物；又は木材、合板、石膏からなるボード状物であることを特徴とする［１］又は［２］に記載の消臭性構造物。
［５］
構造物の基材が、ポリエステル系繊維、ポリアミド系繊維、ポリアクリロニトリル系繊維、ポリプロピレン系繊維、ポリエチレン系繊維、ポリ塩化ビニル系繊維、フッ素系繊維、アラミド系繊維、サルフォン系繊維等の合成繊維、レーヨン、アセテート繊維等の半合成繊維、木綿、羊毛、絹、麻等の天然繊維、ガラス繊維、炭素繊維、セラミックス繊維及びこれらの混合繊維からなる織物、編物、不織布、糸、ロープ、紐状の繊維状物；ポリエステル系樹脂、ポリアミド系樹脂、ポリエチレン系樹脂、ポリプロピレン系樹脂、フッ素系樹脂、シリコン系樹脂、ポリイミド系樹脂、ポリ塩化ビニル系樹脂、天然ゴム、合成ゴムからなるシート状物やスポンジ状物；又は木材、合板、石膏等からなるボード状物であることを特徴とする［１］又は［２］に記載の消臭性構造物。
［６］
前記一般式（１）で表されるＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩を１種以上基材に担持することを特徴とする［１］乃至［５］に記載の消臭性構造物の製造方法。
［７］
［１］乃至［５］に記載の消臭性構造物を使用することを特徴とするアルデヒドの除去方法。
(In the formula, R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. n represents an integer of 1 to 6. Plural R's may be the same or different.)
[2]
In the O-substituted hydroxylamine derivative represented by the general formula (1), R is a hydrogen atom and n is an integer of 1 to 4, or a chemically acceptable salt thereof. The deodorizing structure according to [1], characterized in that it contains one or more types.
[3]
The deodorizing structure according to [1] or [2], wherein the base material of the structure is a fibrous material, a sheet-like material, a sponge-like material, or a board-like material.
[4]
Fabrics, knits, non-woven fabrics, threads, ropes, string-like fibrous materials whose base materials are synthetic fibers, semi-synthetic fibers, natural fibers, glass fibers, carbon fibers, ceramic fibers, and mixed fibers thereof; resins; The deodorizing structure according to [1] or [2], which is a sheet-like material or sponge-like material made of natural rubber or synthetic rubber; or a board-like material made of wood, plywood, or plaster.
[5]
The base material of the structure is synthetic fiber such as polyester fiber, polyamide fiber, polyacrylonitrile fiber, polypropylene fiber, polyethylene fiber, polyvinyl chloride fiber, fluorine fiber, aramid fiber, sulfone fiber, etc. Semi-synthetic fibers such as rayon and acetate fibers, natural fibers such as cotton, wool, silk and hemp, glass fibers, carbon fibers, ceramic fibers, and woven fabrics, knitted fabrics, non-woven fabrics, threads, ropes, and string-like fibers made of mixed fibers. Fibrous materials: Sheet materials and sponges made of polyester resin, polyamide resin, polyethylene resin, polypropylene resin, fluorine resin, silicone resin, polyimide resin, polyvinyl chloride resin, natural rubber, and synthetic rubber. or a board-like object made of wood, plywood, plaster, etc. [1] or [2].
[6]
The eraser according to [1] to [5], characterized in that one or more O-substituted hydroxylamine derivatives represented by the general formula (1) or chemically acceptable salts thereof are supported on the base material. A method for producing an odorous structure.
[7]
A method for removing aldehydes, which comprises using the deodorizing structure described in [1] to [5].
本発明の消臭性構造物は、アルデヒド類を速やかに且つ持続的に捕捉する。その結果、人体に有害なアルデヒド類を低減し、ヒトの生活環境を改善することができる。 The deodorizing structure of the present invention traps aldehydes quickly and continuously. As a result, aldehydes harmful to the human body can be reduced and the living environment of humans can be improved.
本発明の消臭性構造物は、特定のＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩を１種以上含有することをその特徴とする。 The deodorizing structure of the present invention is characterized by containing one or more specific O-substituted hydroxylamine derivatives or chemically acceptable salts thereof.
前記一般式（１）で表されるＯ－置換ヒドロキシルアミン誘導体において、Ｒは水素原子又は炭素数１～４のアルキル基を表し、該アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基等を例示することができる。ｎは１～６の整数を表す。アルデヒド捕捉能が高い点で、Ｒは水素原子が好ましく、ｎは１～４の整数が好ましい。 In the O-substituted hydroxylamine derivative represented by the general formula (1), R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the alkyl group includes a methyl group, an ethyl group, a propyl group, an isopropyl group. Examples include a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and the like. n represents an integer from 1 to 6. From the viewpoint of high aldehyde trapping ability, R is preferably a hydrogen atom, and n is preferably an integer of 1 to 4.
Ｏ－置換ヒドロキシルアミン誘導体（１）は、一部又は全てが無機酸又は有機酸との化学的に許容される塩となっていてもよい。塩の種類としては、特に限定されないが、例えば、塩酸塩、臭化水素酸塩、過塩素酸塩、ケイ酸塩、テトラフルオロホウ酸塩、ヘキサフルオロリン酸塩、硫酸塩、硝酸塩、リン酸塩等の無機酸塩、酢酸塩、クエン酸塩、フマル酸塩、マレイン酸塩、トリフルオロメタンスルホン酸塩、トリフルオロ酢酸塩、安息香酸塩、ｐ－トルエンスルホン酸塩等の有機酸塩が挙げられ、安価である点で無機酸塩が好ましく、塩酸塩がさらに好ましい。 Part or all of the O-substituted hydroxylamine derivative (1) may be a chemically acceptable salt with an inorganic acid or an organic acid. The type of salt is not particularly limited, but includes, for example, hydrochloride, hydrobromide, perchlorate, silicate, tetrafluoroborate, hexafluorophosphate, sulfate, nitrate, and phosphoric acid. Inorganic acid salts such as salts, organic acid salts such as acetate, citrate, fumarate, maleate, trifluoromethanesulfonate, trifluoroacetate, benzoate, p-toluenesulfonate, etc. Inorganic acid salts are preferred, and hydrochlorides are more preferred because they are easy to use and inexpensive.
Ｏ－置換ヒドロキシルアミン誘導体（１）は、分子内にカルボキシ基を有するため、当該カルボキシ基が分子内のアルコキシアミノ基と分子内塩を形成してもよい。また、当該カルボキシ基の一部又は全てがカルボン酸塩となっていてもよい。カルボン酸塩の種類としては、特に限定されないが、例えば、リチウム塩、ナトリウム塩、カリウム塩、セシウム塩等のアルカリ金属塩、アンモニウム塩等が挙げられる。 Since the O-substituted hydroxylamine derivative (1) has a carboxy group in the molecule, the carboxy group may form an inner salt with an alkoxyamino group in the molecule. Further, part or all of the carboxy group may be a carboxylate. The type of carboxylate salt is not particularly limited, but examples include alkali metal salts such as lithium salts, sodium salts, potassium salts, and cesium salts, ammonium salts, and the like.
本発明において、アルデヒド捕捉剤として用いるＯ－置換ヒドロキシルアミン誘導体（１）又はその化学的に許容される塩は一部市販されているが、特許文献（特開平５－８６０１２号公報）記載の方法に従って調製することができる。 In the present invention, some of the O-substituted hydroxylamine derivatives (1) or chemically acceptable salts thereof used as aldehyde scavengers are commercially available; It can be prepared according to the following.
本発明の消臭性構造物の基材としては、特に限定されないが、例えば、ポリエステル系繊維、ポリアミド系繊維、ポリアクリロニトリル系繊維、ポリプロピレン系繊維、ポリエチレン系繊維、ポリ塩化ビニル系繊維、フッ素系繊維、アラミド系繊維、サルフォン系繊維等の合成繊維、レーヨン、アセテート等の半合成繊維、木綿、羊毛、絹、麻等の天然繊維、ガラス繊維、炭素繊維、セラミックス繊維等及びこれらの混合繊維からなる織物、編物、不織布、糸、ロープ、紐等の繊維状物、又はポリエステル系樹脂、ポリアミド系樹脂、ポリエチレン系樹脂、ポリプロピレン系樹脂、フッ素系樹脂、シリコン系樹脂、ポリイミド系樹脂、ポリ塩化ビニル系樹脂、天然ゴム、合成ゴム等からなるシート状物やスポンジ状物、又は木材、合板、石膏等からなるボード状物等が挙げられる。 The base material of the deodorizing structure of the present invention is not particularly limited, but examples include polyester fibers, polyamide fibers, polyacrylonitrile fibers, polypropylene fibers, polyethylene fibers, polyvinyl chloride fibers, and fluorine-based fibers. Fibers, synthetic fibers such as aramid fibers and sulfone fibers, semi-synthetic fibers such as rayon and acetate, natural fibers such as cotton, wool, silk, hemp, glass fibers, carbon fibers, ceramic fibers, etc., and mixed fibers thereof. fibrous materials such as woven fabrics, knitted fabrics, nonwoven fabrics, threads, ropes, and strings, or polyester resins, polyamide resins, polyethylene resins, polypropylene resins, fluorine resins, silicone resins, polyimide resins, and polyvinyl chloride. Examples include sheet-like materials and sponge-like materials made of resins, natural rubber, synthetic rubber, etc., and board-like materials made of wood, plywood, plaster, etc.
本発明の消臭性構造物は、目的、用途に応じて任意の用途で使用することができる。用途は特に限定されないが、例えば、カーテン用、カーペット用、壁装材用、自動車内装材用、家具用等の用途で使用することができる。 The deodorizing structure of the present invention can be used for any purpose depending on the purpose and use. Although the application is not particularly limited, it can be used, for example, for curtains, carpets, wall covering materials, automobile interior materials, furniture, and the like.
本発明の消臭性構造物の製造方法としては、特に限定するものではないが、例えば、一般式（１）で表されるＯ－置換ヒドロキシルアミン誘導体又はその化学的に許容される塩（以下、「Ｏ－置換ヒドロキシルアミン類」という。）を基材に担持する方法が挙げられる。Ｏ－置換ヒドロキシルアミン類は単独で、又は２種以上混合して担持してもよい。 Although the method for producing the deodorizing structure of the present invention is not particularly limited, for example, an O-substituted hydroxylamine derivative represented by general formula (1) or a chemically acceptable salt thereof (hereinafter referred to as , referred to as "O-substituted hydroxylamines") on a substrate. O-substituted hydroxylamines may be supported alone or in combination of two or more.
Ｏ－置換ヒドロキシルアミン類を基材に担持する方法としては、特に限定されないが、例えば、Ｏ－置換ヒドロキシルアミン類を水等の溶媒に溶解させて溶液とし、次いで上記した基材に該溶液を塗布する方法が挙げられる。 The method for supporting O-substituted hydroxylamines on a substrate is not particularly limited, but for example, O-substituted hydroxylamines are dissolved in a solvent such as water to form a solution, and then the solution is applied to the above-mentioned substrate. An example is a method of coating.
基材へのＯ－置換ヒドロキシルアミン類の担持量は、目的に応じて任意に調節可能であり、特に限定するものではないが、Ｏ－置換ヒドロキシルアミン類が０．１～１０ｇ／ｍ２の範囲が好ましく、０．５～５ｇ／ｍ２の範囲がさらに好ましい。 The amount of O-substituted hydroxylamines supported on the base material can be arbitrarily adjusted depending on the purpose, and is not particularly limited . A range of 0.5 to 5 g/m 2 is more preferred.
以下、本発明を具体的に説明するが、本発明はこれらの実施例に限定して解釈されるものではない。 The present invention will be specifically explained below, but the present invention should not be construed as being limited to these Examples.
基材は市販のカーペット（ポリエステル・アクリル樹脂製／レック社製）、カーテン（ポリエステル製／シンコール社製）、ゴムスポンジ（天然ゴム製／東京防音社製）、及び壁紙（ポリ塩化ビニル樹脂製／アサヒペン社製）を用いた。 The base materials are commercially available carpets (made of polyester/acrylic resin/manufactured by REC Co., Ltd.), curtains (made of polyester/manufactured by Shincor Co., Ltd.), rubber sponges (made of natural rubber/manufactured by Tokyo Soundproofing Co., Ltd.), and wallpaper (made of polyvinyl chloride resin/manufactured by Tokyo Soundproofing Co., Ltd.). (manufactured by Asahipen Co., Ltd.) was used.
実施例１～８
基材（縦１０ｃｍ、横１０ｃｍ）に、（アミノオキシ）酢酸を５重量％含有する捕捉剤の水溶液を２０ｇ／ｍ２の割合で塗布し（（アミノオキシ）酢酸としての塗布量＝１ｇ／ｍ２）、室温で２４時間乾燥させ、消臭性構造物を得た。この消臭性構造物をテドラーバッグに窒素ガス５Ｌと共に封入し、アセトアルデヒドガスを加えた。室温で２時間静置後、テドラーバッグ内のガスを２，４－ジニトロフェニルヒドラジン（ＤＮＰＨ）を担持したカートリッジ（製品名：プレセップ－Ｃ ＤＮＰＨ、和光純薬工業製）に吸着させた。このカートリッジからＤＮＰＨ－アルデヒド縮合体を溶出（溶離液＝アセトニトリル）し、溶出液中のＤＮＰＨ－アルデヒド縮合体を液体クロマトグラフ（装置名：Ａｇｉｌｅｎｔ １２２０ Ｉｎｆｉｎｉｔｙ ＬＣ、アジレント・テクノロジー製）で定量して残存アルデヒド濃度を算出した。さらに、アルデヒド捕捉率を下式から算出した。
Examples 1 to 8
An aqueous solution of a scavenger containing 5% by weight of (aminooxy)acetic acid was applied to a substrate (length 10cm, width 10cm) at a rate of 20g/ m2 (coating amount as (aminooxy)acetic acid = 1g/m2). 2 ), it was dried at room temperature for 24 hours to obtain a deodorizing structure. This deodorizing structure was sealed in a Tedlar bag with 5 L of nitrogen gas, and acetaldehyde gas was added. After standing for 2 hours at room temperature, the gas in the Tedlar bag was adsorbed onto a cartridge carrying 2,4-dinitrophenylhydrazine (DNPH) (product name: Presep-C DNPH, manufactured by Wako Pure Chemical Industries, Ltd.). The DNPH-aldehyde condensate is eluted from this cartridge (eluent = acetonitrile), and the DNPH-aldehyde condensate in the eluate is quantified using a liquid chromatograph (device name: Agilent 1220 Infinity LC, manufactured by Agilent Technologies) to determine whether it remains. The aldehyde concentration was calculated. Furthermore, the aldehyde capture rate was calculated from the following formula.
アルデヒド捕捉率（％）＝［（アセトアルデヒド初濃度－残存アセトアルデヒド濃度）÷アセトアルデヒド初濃度］×１００。 Aldehyde capture rate (%) = [(initial acetaldehyde concentration - residual acetaldehyde concentration) ÷ initial acetaldehyde concentration] x 100.
比較例１，３，５，７
（アミノオキシ）酢酸を用いなかったこと以外は実施例１～４と同様に実施した。
Comparative examples 1, 3, 5, 7
The same procedure as in Examples 1 to 4 was carried out except that (aminooxy)acetic acid was not used.
比較例２，４，６，８
（アミノオキシ）酢酸に代え、既存のアルデヒド捕捉剤であるケムキャッチＨ－６０００ＨＳ（ヒドラジド系、大塚化学製）を用いたこと以外は実施例１～４と同様に実施した。
Comparative examples 2, 4, 6, 8
The same procedure as in Examples 1 to 4 was carried out, except that instead of (aminooxy)acetic acid, Chemcatch H-6000HS (hydrazide type, manufactured by Otsuka Chemical), an existing aldehyde scavenger, was used.
実施例１～８及び比較例１～８の結果を表１に示した。 The results of Examples 1 to 8 and Comparative Examples 1 to 8 are shown in Table 1.
表１より明らかなように、本発明の消臭性構造物は、基材のみ、若しくは既存のアルデヒド捕捉剤を含有する基材と比較して高いアセトアルデヒド捕捉性能を示し、さらにホルムアルデヒドに対しても高い捕捉性能を示した。 As is clear from Table 1, the deodorizing structure of the present invention exhibits high acetaldehyde scavenging performance compared to a base material alone or a base material containing an existing aldehyde scavenger, and is also effective against formaldehyde. It showed high capture performance.
実施例９
アセトアルデヒドガスを加えた後、室温で２４時間静置したこと以外は実施例１と同様に実施した結果、アセトアルデヒド捕捉率は９９．９％であり、本発明の消臭性構造物は長時間経過後も高いアルデヒド捕捉性能を維持した。
Example 9
The same procedure as in Example 1 was carried out except that after adding acetaldehyde gas, it was allowed to stand at room temperature for 24 hours. As a result, the acetaldehyde capture rate was 99.9%, and the odor-eliminating structure of the present invention could be used for a long time. The high aldehyde scavenging performance was maintained even after the treatment.
実施例１０
実施例１でアセトアルデヒドを捕捉した後の消臭性構造物をテドラーバッグに窒素ガス５Ｌと共に封入し、６５℃で２時間静置後、テドラーバッグ内のガスを実施例１～８と同様に定量した結果、アセトアルデヒド濃度は０．０１ｐｐｍ未満であり、本発明の消臭性構造物は高温下でもアルデヒドを再放出しないことが確認された。
Example 10
The deodorizing structure after capturing acetaldehyde in Example 1 was sealed in a Tedlar bag with 5 L of nitrogen gas, and after standing at 65°C for 2 hours, the gas in the Tedlar bag was quantified in the same manner as in Examples 1 to 8. The acetaldehyde concentration was less than 0.01 ppm, and it was confirmed that the deodorizing structure of the present invention did not re-release aldehyde even at high temperatures.
本発明の消臭性構造物は、アルデヒド類を速やかに且つ持続的に捕捉する。その結果、人体に有害なアルデヒド類を低減し、ヒトの生活環境を改善することができる。 The deodorizing structure of the present invention traps aldehydes quickly and continuously. As a result, aldehydes harmful to the human body can be reduced and the living environment of humans can be improved.
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| JP2005233613A (en) | 2004-01-20 | 2005-09-02 | Sumika Chemical Analysis Service Ltd | Carbonyl compound trapping material and method for determinating carbonyl compound using the material |
| JP2011173070A (en) | 2010-02-24 | 2011-09-08 | Gifu Prefecture | Adsorbent |
| JP2012224608A (en) | 2011-04-08 | 2012-11-15 | Sumitomo Chemical Co Ltd | Method for obtaining propylene oxide |
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| US5112741A (en) | 1988-07-07 | 1992-05-12 | Enzymatics, Inc. | Acetaldehyde trapping system |
| JP2005233613A (en) | 2004-01-20 | 2005-09-02 | Sumika Chemical Analysis Service Ltd | Carbonyl compound trapping material and method for determinating carbonyl compound using the material |
| JP2011173070A (en) | 2010-02-24 | 2011-09-08 | Gifu Prefecture | Adsorbent |
| JP2012224608A (en) | 2011-04-08 | 2012-11-15 | Sumitomo Chemical Co Ltd | Method for obtaining propylene oxide |
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