JP3771632B2 - Novel β-hydroxycarboxylic acid and perfume composition containing the same - Google Patents
Novel β-hydroxycarboxylic acid and perfume composition containing the same Download PDFInfo
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Description
【０００１】
【発明の属する技術分野】
本発明は、アニマル系の香気を有する新規β−ヒドロキシカルボン酸及びこれを含有する香料組成物に関する。
【０００２】
【従来の技術及び発明が解決しようとする課題】
従来、アニマル系の香気を付与する香料素材としては、シベット、カストリウム、ムスク等の動物から採取される物質が用いられてきた。しかしながら、最近では上記物質は、それらの動物の減少や、動物保護の立場から入手が困難になってきている。
【０００３】
そのため、アニマルノートを付与する代替品が求められているが、その中でも動物を経由せず化学的に容易に合成可能で、天然感と嗜好性を兼ね備えた物質の開発が望まれている。
【０００４】
【課題を解決するための手段】
かかる実情において本発明者らは鋭意研究を重ねた結果、β位にメチル基及びヒドロキシル基を有する新規なカルボン酸が上記要求を満たすものであることを見出し、本発明を完成した。
【０００５】
すなわち本発明は、下記一般式(1)
【０００６】
【化２】
〔式中、Ｒは炭素数３又は４の直鎖又は分岐鎖のアルキル基を示す。〕
で表されるβ−ヒドロキシカルボン酸又はその塩、並びにこれを含有する香料組成物を提供するものである。
【０００８】
【発明の実施の形態】
一般式(1)において、Ｒで示される炭素数３又は４の直鎖又は分岐鎖のアルキル基としては、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec-ブチル基及びtert-ブチル基が挙げられるが、中でもプロピル基、イソブチル基が好ましい。
【０００９】
本発明のβ−ヒドロキシカルボン酸(1)の塩としては、アルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、アルカノールアミン塩、塩基性アミノ酸塩等が挙げられる。
【００１０】
本発明のβ−ヒドロキシカルボン酸(1)又はその塩は、不斉炭素原子を有するため光学異性体が存在し、また水和物を形成することもあるが、本発明は、そのいずれの異性体、ラセミ混合物を含む異性体混合物及び水和物をも包含するものであり、これらのいずれも香料組成物の賦香成分として使用することができる。
【００１１】
本発明のβ−ヒドロキシカルボン酸(1)は、例えば下記反応式に従って、レフォルマトスキー反応〔Reformatskii Reaction; Ber. 20, 1210(1887), J. Russ. Phys. Chem. Soc., 22, 44(1890)〕によりβ位に水酸基を持つエステルを合成し、そのエステルを加水分解することにより合成することができる。この方法により得られるβ−ヒドロキシカルボン酸はβ位炭素原子の不斉に基づきｄ体とｌ体の混合物となるが、香料組成物としての効果は十分に得られる。
【００１２】
【化３】
〔式中、Ｒは前記と同じ意味を示し、Ｘはハロゲン原子を示す。〕
【００１４】
本発明のβ−ヒドロキシカルボン酸(1)又はその塩は、単独では腐敗臭を有するが、低濃度で他の香料成分と組合せることにより、アニマル系香気の賦香成分として好適に使用することができる。この場合の本発明のβ−ヒドロキシカルボン酸(1)又はその塩の香料組成物への配合量は、併用する調合香料の種類、目的とする香気の種類及び強さ等によって異なり、また目的とする香気を賦与できる量であれば特に限定されないが、一般的には0.001〜５重量％の範囲が好ましい。
【００１５】
本発明のβ−ヒドロキシカルボン酸(1)又はその塩と組合せる他の香料成分としては特に限定されず、合成香料及び天然香料のいずれも用いることができる。天然香料としては、例えばイランイラン油、ラベンダー油、ローズ油、ジャスミン油、クラリーセージ油、サンダルウッド油、エレミ油、パチョウリ油、ペルーバルサム油、トルーバルサム油等が挙げられる。また合成香料としては、cis-3-ヘキセノール、ヘキシルシンナミックアルデヒド、シンナミックアルコール、バニリン、クマリン、リモネン、γ−ウンデカラクトン、6-アセチル-1,1,3,4,4,6-ヘキサメチル-テトラヒドロナフタレン、5-アセチル-1,1,2,3,3,6-ヘキサメチルインダン、シクロペンタデカノン、フェニルエチルアルコール、アミンシンナミックアルデヒド、ローズオキサイド、ヘリオトロピン等が挙げられる。これらの香料は、それぞれ単独で又は２種以上を混合した調合香料として、本発明のβ−ヒドロキシカルボン酸(1)又はその塩と組合せて用いることができる。
【００１６】
本発明の香料組成物は、香水、石けん、シャンプー、リンス、洗剤、化粧品、スプレー、芳香剤等の賦香を必要とするものに広範に使用することができる。
【００１７】
【実施例】
以下、実施例を挙げて本発明を更に詳細に説明するが、本発明はこれらに限定されるものではない。
【００１８】
実施例１ 3-ヒドロキシ-3-メチルヘキサン酸の合成：
乾燥窒素気流下、200ml三つ口フラスコにメチルプロピルケトン0.86ｇを無水テトラヒドロフラン25mlに溶解させ、攪拌下、亜鉛粉末6.5ｇを加えた。次にフラスコを氷冷しながら、滴下ロートより11.1mlのブロム酢酸エチルをゆっくりと連続して加え、室温で６時間反応させた後、塩化メチレンを50ml加えた。そこに飽和重層水を滴下し、起泡の発生が無くなるまで添加し、沈殿物をデカンテーションして反応液を塩化メチレンで分層した。有機層を集めて、減圧下濃縮した。濃縮後、濃縮物と同重量のエタノールを加え、２Ｎ水酸化ナトリウム水溶液2.88ｇを滴下した。室温で30分攪拌した後、塩化メチレン５mlを加え、１Ｎ塩酸で当量点まで中和し、塩化メチレン層を濃縮した。濃縮物をカラム精製することにより、標記化合物を得た（収率64％）。
【００１９】
ＩＲ（cm-1；ヒューレットパッカード社製GC/IRシステムHP-5965B）：
3570, 2973, 1767, 1378, 1112
ＭＳ（m/e値；ヒューレットパッカード社製GC/MSシステムHP-5971B）：
71(M+), 85, 103, 131
【００２０】
実施例２ 3-ヒドロキシ-3,4-ジメチルヘキサン酸の合成：
乾燥窒素気流下、200ml三つ口フラスコに3-メチル-2-ペンタノン1.00ｇを無水テトラヒドロフラン25mlに溶解させ、攪拌下、亜鉛粉末6.5ｇを加えた。次にフラスコを氷冷しながら、滴下ロートより11.1mlのブロム酢酸エチルをゆっくりと連続して加え、室温で６時間反応させた後、塩化メチレンを50ml加えた。そこに飽和重層水を滴下し、起泡の発生が無くなるまで添加し、沈殿物をデカンテーションして反応液を塩化メチレンで分層した。有機層を集めて、減圧下濃縮した。濃縮後、濃縮物と同重量のエタノールを加え、２Ｎ水酸化ナトリウム水溶液2.88ｇを滴下した。室温で30分攪拌した後、塩化メチレン５mlを加え、１Ｎ塩酸で当量点まで中和し、塩化メチレン層を濃縮した。濃縮物をカラム精製することにより、標記化合物を得た（収率72％）。
【００２１】
ＩＲ（cm-1；ヒューレットパッカード社製GC/IRシステムHP-5965B）：
3569, 2978, 1763, 1378, 1114
ＭＳ（m/e値；ヒューレットパッカード社製GC/MSシステムHP-5971B）：
85(M+), 103, 127, 145
【００２２】
実施例３ 3-ヒドロキシ-3,5-ジメチルヘキサン酸の合成：
乾燥窒素気流下、200ml三つ口フラスコに4-メチル-2-ペンタノン1.00ｇを無水テトラヒドロフラン25mlに溶解させ、攪拌下、亜鉛粉末6.5ｇを加えた。次にフラスコを氷冷しながら、滴下ロートより11.1mlのブロム酢酸エチルをゆっくりと連続して加え、室温で６時間反応させた後、塩化メチレンを50ml加えた。そこに飽和重層水を滴下し、起泡の発生が無くなるまで添加し、沈殿物をデカンテーションして反応液を塩化メチレンで分層した。有機層を集めて、減圧下濃縮した。濃縮後、濃縮物と同重量のエタノールを加え、２Ｎ水酸化ナトリウム水溶液2.88ｇを滴下した。室温で30分攪拌した後、塩化メチレン５mlを加え、１Ｎ塩酸で当量点まで中和し、塩化メチレン層を濃縮した。濃縮物をカラム精製することにより、標記化合物を得た（収率74％）。
【００２３】
ＩＲ（cm-1；ヒューレットパッカード社製GC/IRシステムHP-5965B）：
3569, 2986, 1764, 1377, 1114
ＭＳ（m/e値；ヒューレットパッカード社製GC/MSシステムHP-5971B）：
85(M+), 103, 127, 145
【００２４】
実施例４ 3-ヒドロキシ-3,4,4-トリメチルペンタン酸の合成：
乾燥窒素気流下、200ml三つ口フラスコに3-メチル-2-ペンタノン1.00ｇを無水テトラヒドロフラン25mlに溶解させ、攪拌下、亜鉛粉末6.5ｇを加えた。次にフラスコを氷冷しながら、滴下ロートより11.1mlのブロム酢酸エチルをゆっくりと連続して加え、室温で６時間反応させた後、塩化メチレンを50ml加えた。そこに飽和重層水を滴下し、起泡の発生が無くなるまで添加し、沈殿物をデカンテーションして反応液を塩化メチレンで分層した。有機層を集めて、減圧下濃縮した。濃縮後、濃縮物と同重量のエタノールを加え、２Ｎ水酸化ナトリウム水溶液2.88ｇを滴下した。室温で30分攪拌した後、塩化メチレン５mlを加え、１Ｎ塩酸で当量点まで中和し、塩化メチレン層を濃縮した。濃縮物をカラム精製することにより、標記化合物を得た（収率75％）。
【００２５】
ＩＲ（cm-1；ヒューレットパッカード社製GC/IRシステムHP-5965B）：
3568, 2972, 1762, 1379, 1139
ＭＳ（m/e値；ヒューレットパッカード社製GC/MSシステムHP-5971B）：
85(M+), 103, 127, 145
【００２６】
実施例５
表１に示す組成の香料基剤(A)及び表２に示す香料基剤(B)を調製し、これに本発明化合物を添加してその香気を未添加品と比較し、添加効果を評価した。
【００２７】
〈評価基準〉
○：十分にアニマル香を付与した効果が認められる。
△：やや付与した効果が認められる。
×：未添加と同等で変化が認められない。
【００２８】
【表１】
【表２】
【発明の効果】
本発明のβ−ヒドロキシカルボン酸(1)又はその塩は、一定濃度で他の香料成分と組合せて用いることにより、アニマル系の香気を付与することができ、香水、石けん、シャンプー、リンス、洗剤、化粧品、スプレー、芳香剤等の賦香を必要とするものに広範に使用することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel β-hydroxycarboxylic acid having an animal-based fragrance and a fragrance composition containing the same.
[0002]
[Prior art and problems to be solved by the invention]
Conventionally, substances collected from animals such as civet, castrium, musk, and the like have been used as perfume materials that impart animal-based aromas. However, recently, it has become difficult to obtain the above substances from the viewpoint of reducing these animals or protecting animals.
[0003]
For this reason, there is a demand for alternatives that give animal notes. Among them, there is a demand for the development of substances that can be easily synthesized chemically without going through animals and have both natural feeling and taste.
[0004]
[Means for Solving the Problems]
Under such circumstances, the present inventors have conducted intensive research and found that a novel carboxylic acid having a methyl group and a hydroxyl group at the β-position satisfies the above requirements, thereby completing the present invention.
[0005]
That is, the present invention provides the following general formula (1)
[0006]
[Chemical 2]
[Wherein, R represents a linear or branched alkyl group having 3 or 4 carbon atoms. ]
(Beta) -hydroxycarboxylic acid represented by these, or its salt, and the fragrance | flavor composition containing this are provided.
[0008]
DETAILED DESCRIPTION OF THE INVENTION
In the general formula (1), the linear or branched alkyl group having 3 or 4 carbon atoms represented by R includes propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and tert-butyl group. Among them, propyl group and isobutyl group are preferable.
[0009]
Examples of the salt of β-hydroxycarboxylic acid (1) of the present invention include alkali metal salts, alkaline earth metal salts, ammonium salts, alkanolamine salts, basic amino acid salts and the like.
[0010]
Since β-hydroxycarboxylic acid (1) or a salt thereof of the present invention has an asymmetric carbon atom, optical isomers exist and may form hydrates. Body, isomer mixtures including racemic mixtures, and hydrates, and any of these can be used as a perfuming ingredient in perfume compositions.
[0011]
The β-hydroxycarboxylic acid (1) of the present invention is prepared, for example, according to the following reaction formula (Reformatskii Reaction; Ber. 20, 1210 (1887), J. Russ. Phys. Chem. Soc., 22, 44). (1890)] can be synthesized by synthesizing an ester having a hydroxyl group at the β-position and hydrolyzing the ester. The β-hydroxycarboxylic acid obtained by this method becomes a mixture of d-form and l-form based on the asymmetry of the β-position carbon atom, but the effect as a fragrance composition is sufficiently obtained.
[0012]
[Chemical 3]
[Wherein, R represents the same meaning as described above, and X represents a halogen atom. ]
[0014]
The β-hydroxycarboxylic acid (1) or a salt thereof of the present invention has a rotting odor when used alone, but it can be suitably used as a flavoring component for animal fragrances by combining with other flavoring components at a low concentration. Can do. In this case, the blending amount of the β-hydroxycarboxylic acid (1) of the present invention or a salt thereof in the fragrance composition varies depending on the type of blended fragrance used, the type and intensity of the target fragrance, etc. Although it will not specifically limit if it is the quantity which can provide the fragrance to perform, Generally the range of 0.001 to 5 weight% is preferable.
[0015]
It does not specifically limit as another fragrance | flavor component combined with (beta) -hydroxycarboxylic acid (1) or its salt of this invention, Both a synthetic | combination fragrance | flavor and a natural fragrance | flavor can be used. Examples of natural fragrances include ylang-ylang oil, lavender oil, rose oil, jasmine oil, clary sage oil, sandalwood oil, elemi oil, patchouli oil, peru balsam oil, and trobalsam oil. Synthetic fragrances include cis-3-hexenol, hexyl cinnamic aldehyde, cinnamic alcohol, vanillin, coumarin, limonene, γ-undecalactone, 6-acetyl-1,1,3,4,4,6-hexamethyl. -Tetrahydronaphthalene, 5-acetyl-1,1,2,3,3,6-hexamethylindane, cyclopentadecanone, phenylethyl alcohol, amine cinnamic aldehyde, rose oxide, heliotropin and the like. These fragrances can be used alone or in combination with the β-hydroxycarboxylic acid (1) of the present invention or a salt thereof as a blended fragrance in which two or more kinds are mixed.
[0016]
The perfume composition of the present invention can be widely used for those requiring perfume, such as perfumes, soaps, shampoos, rinses, detergents, cosmetics, sprays, and fragrances.
[0017]
【Example】
EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to these.
[0018]
Example 1 Synthesis of 3-hydroxy-3-methylhexanoic acid:
Under a dry nitrogen stream, 0.86 g of methyl propyl ketone was dissolved in 25 ml of anhydrous tetrahydrofuran in a 200 ml three-necked flask, and 6.5 g of zinc powder was added with stirring. Next, while cooling the flask with ice, 11.1 ml of ethyl bromoacetate was slowly and continuously added from the dropping funnel and reacted at room temperature for 6 hours, and then 50 ml of methylene chloride was added. Saturated multistory water was dripped there, it added until generation | occurrence | production of foaming disappeared, the deposit was decanted, and the reaction liquid was separated by methylene chloride. The organic layer was collected and concentrated under reduced pressure. After concentration, ethanol of the same weight as the concentrate was added, and 2.88 g of 2N aqueous sodium hydroxide solution was added dropwise. After stirring at room temperature for 30 minutes, 5 ml of methylene chloride was added, neutralized to the equivalent point with 1N hydrochloric acid, and the methylene chloride layer was concentrated. The concentrate was subjected to column purification to obtain the title compound (yield 64%).
[0019]
IR (cm -1 ; Hewlett-Packard GC / IR system HP-5965B):
3570, 2973, 1767, 1378, 1112
MS (m / e value; GC / MS system HP-5971B manufactured by Hewlett-Packard Company):
71 (M + ), 85, 103, 131
[0020]
Example 2 Synthesis of 3-hydroxy-3,4-dimethylhexanoic acid:
Under a dry nitrogen stream, 1.00 g of 3-methyl-2-pentanone was dissolved in 25 ml of anhydrous tetrahydrofuran in a 200 ml three-necked flask, and 6.5 g of zinc powder was added with stirring. Next, while cooling the flask with ice, 11.1 ml of ethyl bromoacetate was slowly and continuously added from the dropping funnel and reacted at room temperature for 6 hours, and then 50 ml of methylene chloride was added. Saturated multistory water was dripped there, it added until generation | occurrence | production of foaming disappeared, the deposit was decanted, and the reaction liquid was separated by methylene chloride. The organic layer was collected and concentrated under reduced pressure. After concentration, ethanol of the same weight as the concentrate was added, and 2.88 g of 2N aqueous sodium hydroxide solution was added dropwise. After stirring at room temperature for 30 minutes, 5 ml of methylene chloride was added, neutralized to the equivalent point with 1N hydrochloric acid, and the methylene chloride layer was concentrated. The concentrate was subjected to column purification to obtain the title compound (yield 72%).
[0021]
IR (cm -1 ; Hewlett-Packard GC / IR system HP-5965B):
3569, 2978, 1763, 1378, 1114
MS (m / e value; GC / MS system HP-5971B manufactured by Hewlett-Packard Company):
85 (M + ), 103, 127, 145
[0022]
Example 3 Synthesis of 3-hydroxy-3,5-dimethylhexanoic acid:
Under a dry nitrogen stream, 1.00 g of 4-methyl-2-pentanone was dissolved in 25 ml of anhydrous tetrahydrofuran in a 200 ml three-necked flask, and 6.5 g of zinc powder was added with stirring. Next, while cooling the flask with ice, 11.1 ml of ethyl bromoacetate was slowly and continuously added from the dropping funnel and reacted at room temperature for 6 hours, and then 50 ml of methylene chloride was added. Saturated multistory water was dripped there, it added until generation | occurrence | production of foaming disappeared, the deposit was decanted, and the reaction liquid was separated by methylene chloride. The organic layer was collected and concentrated under reduced pressure. After concentration, ethanol of the same weight as the concentrate was added, and 2.88 g of 2N aqueous sodium hydroxide solution was added dropwise. After stirring at room temperature for 30 minutes, 5 ml of methylene chloride was added, neutralized to the equivalent point with 1N hydrochloric acid, and the methylene chloride layer was concentrated. The concentrate was subjected to column purification to obtain the title compound (yield 74%).
[0023]
IR (cm -1 ; Hewlett-Packard GC / IR system HP-5965B):
3569, 2986, 1764, 1377, 1114
MS (m / e value; GC / MS system HP-5971B manufactured by Hewlett-Packard Company):
85 (M + ), 103, 127, 145
[0024]
Example 4 Synthesis of 3-hydroxy-3,4,4-trimethylpentanoic acid:
Under a dry nitrogen stream, 1.00 g of 3-methyl-2-pentanone was dissolved in 25 ml of anhydrous tetrahydrofuran in a 200 ml three-necked flask, and 6.5 g of zinc powder was added with stirring. Next, while cooling the flask with ice, 11.1 ml of ethyl bromoacetate was slowly and continuously added from the dropping funnel and reacted at room temperature for 6 hours, and then 50 ml of methylene chloride was added. Saturated multistory water was dripped there, it added until generation | occurrence | production of foaming disappeared, the deposit was decanted, and the reaction liquid was separated by methylene chloride. The organic layer was collected and concentrated under reduced pressure. After concentration, ethanol of the same weight as the concentrate was added, and 2.88 g of 2N aqueous sodium hydroxide solution was added dropwise. After stirring at room temperature for 30 minutes, 5 ml of methylene chloride was added, neutralized to the equivalent point with 1N hydrochloric acid, and the methylene chloride layer was concentrated. The concentrate was subjected to column purification to obtain the title compound (yield 75%).
[0025]
IR (cm -1 ; Hewlett-Packard GC / IR system HP-5965B):
3568, 2972, 1762, 1379, 1139
MS (m / e value; GC / MS system HP-5971B manufactured by Hewlett-Packard Company):
85 (M + ), 103, 127, 145
[0026]
Example 5
A fragrance base (A) having the composition shown in Table 1 and a fragrance base (B) shown in Table 2 were prepared, the present compound was added thereto, and the fragrance was compared with an unadded product, and the effect of addition was evaluated. did.
[0027]
<Evaluation criteria>
○: An effect of sufficiently imparting an animal scent is recognized.
Δ: Slightly imparted effect is observed.
X: It is equivalent to no addition and no change is recognized.
[0028]
[Table 1]
[Table 2]
【The invention's effect】
The β-hydroxycarboxylic acid (1) of the present invention or a salt thereof can be used in combination with other perfume ingredients at a constant concentration to impart an animal-based fragrance, and can be used as a perfume, soap, shampoo, rinse or detergent. It can be widely used for cosmetics, sprays, fragrances and the like that require fragrance.
Claims (3)
で表されるβ−ヒドロキシカルボン酸からなるアニマルノート用香料素材。The following general formula (1)
The fragrance | flavor material for animal notes which consists of ( beta) -hydroxycarboxylic acid represented by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18328096A JP3771632B2 (en) | 1996-07-12 | 1996-07-12 | Novel β-hydroxycarboxylic acid and perfume composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18328096A JP3771632B2 (en) | 1996-07-12 | 1996-07-12 | Novel β-hydroxycarboxylic acid and perfume composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1025265A JPH1025265A (en) | 1998-01-27 |
| JP3771632B2 true JP3771632B2 (en) | 2006-04-26 |
Family
ID=16132899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18328096A Expired - Fee Related JP3771632B2 (en) | 1996-07-12 | 1996-07-12 | Novel β-hydroxycarboxylic acid and perfume composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3771632B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100356901C (en) * | 2003-03-03 | 2007-12-26 | 高砂香料工业株式会社 | Pseudo body odor composition and perfume composition for inhibiting body odor |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031766A1 (en) | 2002-10-04 | 2004-04-15 | Kao Corporation | Indicator for assessing body odor, process for producing the same, body odor assessment method, method of assessing efficaciousness of deodorant and kit for conveniently assesing body odor |
| EP2368602A1 (en) * | 2003-03-03 | 2011-09-28 | Takasago International Corporation | Deodorant perfume composition comprising essential oils for masking an acid odour |
| JP2004262900A (en) * | 2003-03-04 | 2004-09-24 | Takasago Internatl Corp | Body odor-suppressing perfume composition |
| KR100773499B1 (en) * | 2006-07-07 | 2007-11-05 | 대진대학교 산학협력단 | Dynamic frequency filtering system and method of micro speaker unit for mobile terminal device |
-
1996
- 1996-07-12 JP JP18328096A patent/JP3771632B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100356901C (en) * | 2003-03-03 | 2007-12-26 | 高砂香料工业株式会社 | Pseudo body odor composition and perfume composition for inhibiting body odor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1025265A (en) | 1998-01-27 |
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