JP2781870B2 - Aqueous high concentration composition of α-sulfo fatty acid ester salt - Google Patents
Aqueous high concentration composition of α-sulfo fatty acid ester saltInfo
- Publication number
- JP2781870B2 JP2781870B2 JP1238863A JP23886389A JP2781870B2 JP 2781870 B2 JP2781870 B2 JP 2781870B2 JP 1238863 A JP1238863 A JP 1238863A JP 23886389 A JP23886389 A JP 23886389A JP 2781870 B2 JP2781870 B2 JP 2781870B2
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- Japan
- Prior art keywords
- acid ester
- ester salt
- sulfofatty acid
- fatty acid
- high concentration
- Prior art date
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は、α−スルホ脂肪酸エステル塩を高濃度で含
有する水性組成物（スラリー）に関する。Description: TECHNICAL FIELD The present invention relates to an aqueous composition (slurry) containing a α-sulfofatty acid ester salt at a high concentration.
従来の技術 α−スルホ脂肪酸エステル塩は、洗浄力や耐硬水性等
に優れた界面活性剤であり、これを配合した潜在組成物
も報告されている（特開昭62−597号公報）。2. Description of the Related Art α-Sulfo fatty acid ester salts are surfactants having excellent detergency and hard water resistance, and latent compositions containing the same have been reported (JP-A-62-597).
α−スルホ脂肪酸エステル塩は、一般に、原料脂肪酸
のエステル化（エステル交換）→スルホン化→中和の各
工程を経て製造されるが、最後に水酸化ナトリウム等の
アルカリ水溶液で中和されることから、水性溶液ないし
スラリーとして得られる。このスラリーの界面活性剤濃
度は、製造装置、輸送時および包装材料等の経済的見地
からできるだけ高濃度であることが望ましいが、高濃度
化すると粘度が高くなり、ハンドリング性の点で問題が
あった。The α-sulfofatty acid ester salt is generally produced through the steps of esterification (transesterification) → sulfonation → neutralization of the raw material fatty acid, and is finally neutralized with an aqueous alkali solution such as sodium hydroxide. From aqueous solutions or slurries. It is desirable that the concentration of the surfactant in the slurry be as high as possible from the economical point of view of manufacturing equipment, transportation, packaging materials, etc. However, increasing the concentration increases the viscosity, and there is a problem in handling properties. Was.
α−スルホ脂肪酸エステル塩水性スラリーの高濃度化
に関しては、下記のような種々の技術が報告されている
が、界面活性剤濃度が65〜80重量％領域の高濃度化技術
は、実質上開発されていない。The following various techniques have been reported for increasing the concentration of the aqueous slurry of α-sulfofatty acid ester salt, but the technique for increasing the concentration of the surfactant in the range of 65 to 80% by weight has been substantially developed. It has not been.
（１）特開昭62−186930号公報:C２〜22の脂肪酸を10〜
30wt％共存させることにより、界面活性剤濃度（AI）を
50〜70wt％とする。(1) JP-62-186930 JP: 10 fatty acids C 2 to 22
By coexisting at 30wt%, the surfactant concentration (AI)
50 to 70 wt%.
（２）特開昭62−116698号公報：無機硫酸塩0.2〜30wt
％、ポリエチレングリコール、ポリプロピレングリコー
ル、グリセリン等0.1〜15wt％を共存させ、AI35〜60wt
％とする。(2) JP-A-62-116698: inorganic sulfate 0.2 to 30 wt.
%, Polyethylene glycol, polypropylene glycol, glycerin etc. 0.1 ~ 15wt% coexist, AI35 ~ 60wt
%.
（３）特開昭59−157199号公報：エチレンオキサイドの
平均付加モル数１〜20のノニオン界面活性剤を１〜15wt
％添加し、AI50wt％以上とする。(3) JP-A-59-157199: Nonionic surfactant having an average addition mole number of ethylene oxide of 1 to 20 is mixed with 1 to 15 wt.
% To make AI 50wt% or more.
（４）特開昭61−162596号公報:C11〜21のアルカンスル
ホン酸塩を0.5〜10wt％添加し、AI30％以上とする。(4) JP-61-162596 JP: alkane sulfonates C 11 to 21 is added 0.5-10%, and AI30% or more.
（５）特開昭59−74195号公報:C１〜４のアルコールサ
ルフェート３〜8wt％共存せしめ、AI40〜65wt％とす
る。(5) JP-A-59-74195: Alcohol sulfate of C 1-4 is coexisted with 3-8 wt% to make AI 40-65 wt%.
（６）特開昭62−220597号公報：中和物を中性無機質
（NaCl）で塩析し、AI50〜70wt％とする。(6) JP-A-62-220597: The neutralized product is salted out with a neutral inorganic substance (NaCl) to make AI 50 to 70% by weight.
（７）特開昭62−108853号公報：中和に先立って、スル
ホン化時に残った未反応SO3とアルコール類を反応せし
め、対AI当たりのα−スルホ脂肪酸ジ塩量が10wt％以下
で、AI35wt％以上、好ましくは40〜65wt％のスラリーを
得る。(7) JP-A-62-108853: Prior to neutralization, unreacted SO 3 remaining during sulfonation is reacted with alcohols, and the amount of α-sulfofatty acid disalt per AI is not more than 10 wt%. , 35% by weight or more of AI, preferably 40 to 65% by weight.
（８）特開昭61−280467号公報：無機硫酸塩を２〜30重
量％共存させ、AI30〜60wt％とする。(8) JP-A-61-280467: Incorporation of 2 to 30% by weight of inorganic sulfate to make AI 30 to 60% by weight.
（９）特開昭61−276895号公報：α−スルホ脂肪酸エス
テル塩の炭素数分布を、Ｃ16〜24/C６〜15＝95/5〜50/5
0とし、AI30〜60wt％とする。(9) JP-A-61-276895: The carbon number distribution of α-sulfofatty acid ester salt is determined by C 16-24 / C 6-15 = 95 / 5-50 / 5.
0, and 30 to 60 wt% AI.
（10）特開昭61−118355号公報：α−スルホ脂肪酸エス
テル塩の炭素数をＣ16〜18とし、AI60wt％以上とする。(10) JP-A-61-118355: The α-sulfofatty acid ester salt has a carbon number of C 16-18 and an AI of at least 60 wt%.
発明が解決しようとする課題 本発明は、α−スルホ脂肪酸エステル塩を高濃度に含
む領域において、粘度が低く流動性の良好な水性組成物
を提供するものである。Problems to be Solved by the Invention The present invention is to provide an aqueous composition having low viscosity and good fluidity in a region containing a high concentration of α-sulfofatty acid ester salt.
発明の構成 本発明のα−スルホ脂肪酸エステル塩の水性高濃度組
成物は、（ａ）α−スルホ脂肪酸エステル塩と（ｂ）α
−スルホ脂肪酸ジ塩とを重量比で（ａ）／（ｂ）＝96/4
〜100/0の範囲で含んで成る界面活性剤を65〜80重量％
含有し、かつ、無機硫酸塩の含有量が２重量％以下であ
ることを特徴とする。Constitution of the Invention The aqueous high-concentration composition of the α-sulfofatty acid ester salt of the present invention comprises (a) an α-sulfofatty acid ester salt and (b) an α-sulfofatty acid ester salt.
(A) / (b) = 96/4 by weight ratio with sulfo fatty acid disalt
65-80% by weight of surfactant comprising in the range of ~ 100/0
And the content of the inorganic sulfate is 2% by weight or less.
以下、本発明についてさらに詳細に説明する。 Hereinafter, the present invention will be described in more detail.
α−スルホ脂肪酸エステル塩は、脂肪酸低級アルキル
エステルのスルホン化物の塩であり、典型的に下記一般
式（Ｉ）で表わされる。The α-sulfofatty acid ester salt is a salt of a sulfonated fatty acid lower alkyl ester, and is typically represented by the following general formula (I).
（R :アルキル基またはアルケニル基 Ｒ′：低級アルキル基 M :対イオン） α−スルホ脂肪酸エステル塩は、天然油脂や合成脂肪
酸由来の脂肪酸低級アルキルエステルを蒸留、スルホン
化、漂白、中和することによって得られる。 (R: alkyl group or alkenyl group R ′: lower alkyl group M: counter ion) α-sulfofatty acid ester salt is to distill, sulfonate, bleach and neutralize fatty acid lower alkyl esters derived from natural fats and oils and synthetic fatty acids. Obtained by
中和は、NaOH,KOH,Mg（OH）２等の苛性アルカリや水
性アルカノールアミン、アンモニアなどを用いて行なう
ことができる。中和温度は50〜70℃が好ましく、また、
α−スルホ脂肪酸エステル塩のα−スルホ脂肪酸ジ塩へ
の加水分解を抑えるために、α−スルホ脂肪酸エステル
塩とアルカリ水溶液を同時に供給し、pH4〜７で連続中
和を行なうのがよい。Neutralization can be performed using a caustic alkali such as NaOH, KOH, Mg (OH) 2 , an aqueous alkanolamine, ammonia, or the like. The neutralization temperature is preferably 50 to 70 ° C, and
In order to suppress the hydrolysis of the α-sulfofatty acid ester salt to the α-sulfofatty acid disalt, it is preferable to simultaneously supply the α-sulfofatty acid ester salt and an aqueous alkali solution and to perform continuous neutralization at pH 4 to 7.
脂肪酸残基（Ｒ−CHCOO）の炭素数は、６〜24が好適
であり、Ｒは直鎖でも分岐鎖でもよい。The fatty acid residue (R-CHCOO) preferably has 6 to 24 carbon atoms, and R may be linear or branched.
低級アルキン基（Ｒ′）は直鎖でも分岐鎖でもよく、
炭素数は１〜４が好適である。The lower alkyne group (R ') may be linear or branched,
The carbon number is preferably 1 to 4.
また、対イオン（Ｍ）としては、Na,K等のアルカリ金
属などの水溶性塩が用いられる。As the counter ion (M), a water-soluble salt such as an alkali metal such as Na or K is used.
α−スルホ脂肪酸ジ塩は、下記一般式で表わされ、ス
ルホ脂肪酸エステル塩をアルカリで加水分解することに
よって容易に得られ、また、α−スルホ脂肪酸エステル
塩の製造時に副生するので製造条件を制御することによ
っても所定量を含有せしめるできる。The α-sulfofatty acid disalt is represented by the following general formula and is easily obtained by hydrolyzing a sulfofatty acid ester salt with an alkali. A predetermined amount can also be contained by controlling the amount.
（R,M:一般式（Ｉ）に同じ） 本発明の水性組成物は、α−スルホ脂肪酸エステル塩
とα−スルホ脂肪酸ジ塩とを、合計量として65〜80重量
％の範囲で含む。この量（AI）が65〜80重量％の範囲を
外れると、後記の如く各成分量を調整しても、水性組成
物の粘度が上昇し、流動性が劣化する。 (R, M: same as in general formula (I)) The aqueous composition of the present invention contains α-sulfofatty acid ester salt and α-sulfofatty acid disalt in a total amount of 65 to 80% by weight. If the amount (AI) is out of the range of 65 to 80% by weight, the viscosity of the aqueous composition increases and the fluidity deteriorates even if the amounts of the respective components are adjusted as described below.
（ａ）α−スルホ脂肪酸エステル塩と（ｂ）α−スル
ホ脂肪酸ジ塩とは、本発明の水性組成物中に、重量比で
（ａ）／（ｂ）＝96/4〜100/0、好ましくは97/3〜100/0
の範囲で含まれる。96/4を超えてジ塩量が増大すると、
AI65〜85wt％の領域では水性組成物が増粘し、流動性が
劣化してしまう。(A) α-sulfofatty acid ester salt and (b) α-sulfofatty acid disalt are contained in the aqueous composition of the present invention in a weight ratio of (a) / (b) = 96/4 to 100/0, Preferably 97/3 to 100/0
Included in the range. When the amount of di-salt increases beyond 96/4,
In the range of AI 65 to 85 wt%, the aqueous composition thickens and the fluidity deteriorates.
上述の通り、α−スルホ脂肪酸エステル塩の製造時に
は、ジ塩が副生する傾向があるので、反応条件の調整や
精製により、少なくともα−スルホ脂肪酸エステル塩中
のジ塩量を4wt％以下に抑える。As described above, during the production of the α-sulfofatty acid ester salt, a disalt tends to be produced as a by-product. suppress.
なお、従来α−スルホ脂肪酸エステル塩中のジ塩量の
測定は、メチレンブルー逆滴定法によっていたが、本発
明では高速液体クロマトグラフ法によった。高速液体ク
ロマトグラフ法は、メチレンブルー逆滴定法よりも検知
精度に優れており、微少含有量も検出でき、また、検出
値もメチレンブルー逆滴定法よりも高目に出る。高速液
体クロマトグラフ法の評価は後述するが、アニオン交換
モードのカラムを用い、NaClO4を１％含むメタノール／
水混合液［4/1（vol/vol）］を移動相とし、示差屈折計
を用いて検量線法により定量する。Conventionally, the amount of di-salt in the α-sulfofatty acid ester salt was measured by a methylene blue back titration method, but in the present invention, a high-performance liquid chromatography method was used. The high performance liquid chromatograph method has a higher detection accuracy than the methylene blue back titration method, can detect even a minute content, and has a higher detection value than the methylene blue back titration method. Evaluation of high-performance liquid chromatography will be described later, using a column of anion exchange mode, methanol containing NaClO 4 1% /
A water mixture [4/1 (vol / vol)] is used as a mobile phase, and quantified by a calibration curve method using a differential refractometer.
また、本発明の水性組成物では、Na2SO4,K2SO4などの
無機硫酸塩の含有量を2wt％以下とする。2wt％を超えて
無機硫酸塩が共存すると、水性組成物が増粘して、流動
性が劣化する。In the aqueous composition of the present invention, the content of inorganic sulfates such as Na 2 SO 4 and K 2 SO 4 is set to 2% by weight or less. When the content of the inorganic sulfate exceeds 2 wt%, the aqueous composition thickens, and the fluidity is deteriorated.
α−スルホ脂肪酸エステル塩の製造に際しては、スル
ホン化剤としてSO3などを用い、また中和時に水酸化ナ
トリウムなどのアルカリを用いるので、硫酸ナトリウム
等の硫酸塩が副生する傾向がある。そこで、反応条件の
調整や精製により、水性組成物中の硫酸塩量を少なくと
も2wt％以下に抑える。In producing an α-sulfo fatty acid ester salt, SO 3 or the like is used as a sulfonating agent, and an alkali such as sodium hydroxide is used at the time of neutralization, so that a sulfate such as sodium sulfate tends to be produced as a by-product. Therefore, by adjusting and purifying the reaction conditions, the amount of sulfate in the aqueous composition is suppressed to at least 2 wt% or less.
本発明の水性スラリー中には、上記各成分の他に、製
造時に混入する微量の脂肪酸塩、脂肪酸エステル、低級
アルコール、過酸化水素、あるいは安息香酸ナトリウ
ム、クエン酸ナトリウム、リン酸ナトリウムなどのpH緩
衝剤などを共存させてもよい。In the aqueous slurry of the present invention, in addition to the above components, trace amounts of fatty acid salts, fatty acid esters, lower alcohols, hydrogen peroxide, or sodium benzoate, sodium citrate, sodium phosphate, etc. A buffer and the like may coexist.
発明の効果 本発明によれば、界面活性剤量が65〜80wt％の高濃度
領域で、α−スルホ脂肪酸エステル塩水性組成物の粘度
を低下せしめ流動性を改善することができ、ポンピング
等のハンドリングが容易となり、また、噴霧乾燥等の際
には負荷が軽減される。Effect of the Invention According to the present invention, in the high concentration region where the amount of surfactant is 65 to 80 wt%, the viscosity of the aqueous composition of the α-sulfofatty acid ester salt can be reduced to improve the flowability, and it can be used for pumping and the like. Handling becomes easy, and the load is reduced during spray drying and the like.
実 施 例 種々の炭素数分布をもつパーム油、ヤシ油、パーム核
油由来の低級アルコールエステルを、常法通りスルホン
化、漂白、再エステル化、中和を行ない、また必要に応
じ、再結晶などの精製処理をし、表−１に示すような各
種のα−スルホ脂肪酸エステル塩およびα−スルホ脂肪
酸ジ塩を得た。これら界面活性剤を必要に応じ市販の無
機硫酸塩および水を混合し、種々の組成物を調製し、粘
度挙動を測定した。結果を表−１に示す。Example: A lower alcohol ester derived from palm oil, coconut oil, and palm kernel oil having various carbon number distributions is sulfonated, bleached, re-esterified, neutralized, and recrystallized as necessary. And the like, to obtain various α-sulfofatty acid ester salts and α-sulfofatty acid disalts as shown in Table 1. These surfactants were mixed with commercially available inorganic sulfates and water as needed to prepare various compositions, and the viscosity behavior was measured. The results are shown in Table 1.
ここで、測定は以下のように行なった。 Here, the measurement was performed as follows.
（１）粘度の測定 ブルックフィールド型粘度計VSH typeにて測定した。(1) Measurement of viscosity The viscosity was measured with a Brookfield viscometer VSH type.
（２）ジ塩の測定 Proceedings on ISF−JOCS world congress,1988,vo
l.II,721〜725頁（The Japan Oil Chemist's Society）
に記載の方法に準拠して、高速液体クロマトグラフ（HP
LC）を用い以下の通り行なった。(2) Measurement of disalts Proceedings on ISF-JOCS world congress, 1988, vo
l.II, pp.721-725 (The Japan Oil Chemist's Society)
High-performance liquid chromatograph (HP
LC) was performed as follows.
（ｉ） HPLC条件 カラム:nucleosil 5SB（I.D＝4.6mm,L＝125mm）［ガス
クロ工業（株）製のアニオン交換分離モードのカラム］ 移動層:1％（vol/vol）NaClO4を含むメタノール／水［4
/1（vol/vol）］混合液、流速0.8ml/min 注入量:200μ 検出器：示差屈折計（RI）、感度４×10-5RIUFS （ii） 検量線の作成 α−スルホ脂肪酸ジ塩を1mg/ml濃度で含むエタノール
／水（1/1）溶液を、メタノール／水（4/1）混合液で希
釈し、ジ塩濃度として0.05,0.10,0.15,0.20mg/ml含む４
つの溶液をそれぞれ調製する。(I) HPLC conditions Column: nucleosil 5SB (ID = 4.6 mm, L = 125 mm) [Column in an anion exchange separation mode manufactured by Gaschrom Industry Co., Ltd.] Moving bed: methanol containing 1% (vol / vol) NaClO 4 / Water [4
/ 1 (vol / vol)] Mixed solution, flow rate 0.8 ml / min Injection volume: 200 μ Detector: Differential refractometer (RI), sensitivity 4 × 10 -5 RIUFS (ii) Preparation of calibration curve α-sulfo fatty acid disalt The ethanol / water (1/1) solution containing 1 mg / ml in water is diluted with a methanol / water (4/1) mixed solution to contain 0.05, 0.10, 0.15, 0.20 mg / ml as the disalt concentration.
Prepare each of the two solutions.
この溶液を各々、200μループインジェクターを使
用しHPLCに注入して分析し、ジ塩のクロマトグラフを得
る。Each of the solutions is injected into a HPLC using a 200μ loop injector and analyzed to obtain a disalt chromatograph.
このジ塩のピーク面積を測定して検量線を作成する。 A calibration curve is prepared by measuring the peak area of this disalt.
（３）試料調製および測定 試料スラリー（界面活性剤として約0.3g）を精秤し、
エタノール／水（1/1）混合液に溶解し50mlに定容す
る。これより10ml分取してメタノールで50mlに定容し、
HPLCに注入しクロマトグラフを得る。このクロマトグラ
フからジ塩のピーク面積を求め、検量線よりジ塩濃度を
求め、次式よりスラリー（水性組成物）中のジ塩量を算
出する。(3) Sample preparation and measurement A sample slurry (about 0.3 g as a surfactant) was precisely weighed,
Dissolve in an ethanol / water (1/1) mixture and make up to 50 ml. Take 10 ml aliquot from this, make up to 50 ml with methanol,
Inject into HPLC to get chromatograph. The peak area of the disalt is determined from the chromatograph, the disalt concentration is determined from the calibration curve, and the disalt amount in the slurry (aqueous composition) is calculated from the following equation.
S:試料採取量（mg） A:検量線より求めた濃度（mg/ml） S: Sampling amount (mg) A: Concentration (mg / ml) obtained from calibration curve
フロントページの続き (72)発明者 近藤 房男 東京都墨田区本所１丁目３番７号 ライ オン株式会社内 (56)参考文献 特開 昭61−276895（ＪＰ，Ａ) 特開 昭61−118355（ＪＰ，Ａ) 特開 昭62−108853（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) C11D 1/28 B01J 13/00Continuation of front page (72) Inventor Fumio Kondo 1-3-7, Honjo, Sumida-ku, Tokyo Inside Rion Co., Ltd. (56) References JP-A-61-276895 (JP, A) JP-A-61- 118355 (JP, A) JP-A-62-108853 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) C11D 1/28 B01J 13/00
Claims (1)
（ｂ）α−スルホ脂肪酸ジ塩とを重量比で（ａ）／
（ｂ）＝96/4〜100/0の範囲で含んで成る界面活性剤を6
5〜80重量％含有し、かつ、無機硫酸塩の含有量が２重
量％以下であることを特徴とするα−スルホ脂肪酸エス
テル塩の水性高濃度組成物。(1) A weight ratio of (a) an α-sulfofatty acid ester salt and (b) an α-sulfofatty acid disalt,
(B) 6 surfactants comprising in the range of 96/4 to 100/0
An aqueous high-concentration composition of an α-sulfofatty acid ester salt, comprising 5 to 80% by weight and having an inorganic sulfate content of 2% by weight or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1238863A JP2781870B2 (en) | 1989-09-14 | 1989-09-14 | Aqueous high concentration composition of α-sulfo fatty acid ester salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1238863A JP2781870B2 (en) | 1989-09-14 | 1989-09-14 | Aqueous high concentration composition of α-sulfo fatty acid ester salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03101828A JPH03101828A (en) | 1991-04-26 |
| JP2781870B2 true JP2781870B2 (en) | 1998-07-30 |
Family
ID=17036383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1238863A Expired - Lifetime JP2781870B2 (en) | 1989-09-14 | 1989-09-14 | Aqueous high concentration composition of α-sulfo fatty acid ester salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2781870B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688982A (en) * | 1993-08-20 | 1997-11-18 | The Procter & Gamble Company | No-bleach process for making sulfonated fatty acid alkyl ester surfactant |
| KR980002224A (en) * | 1996-06-29 | 1998-03-30 | 이능희 | Synthetic Detergent Bar Composition Containing Alpha Sulfo Fatty Acid Diphosphate |
| JP5222733B2 (en) * | 2006-12-21 | 2013-06-26 | ライオン株式会社 | Surfactant aqueous liquid and method for producing the same |
| US8168580B2 (en) | 2008-11-21 | 2012-05-01 | Lion Corporation | Method for producing aqueous α-sulfo fatty acid alkyl ester salt solution |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3439520A1 (en) * | 1984-10-29 | 1986-04-30 | Henkel KGaA, 4000 Düsseldorf | PUMPABLE HIGH CONCENTRATED AQUEOUS PASTS IN FRONT OF ALKALINE SALT ALPHA-SULFONATED FATTY ACID ALKYLESTER AND METHOD FOR THE PRODUCTION THEREOF |
| JPS61276895A (en) * | 1985-05-31 | 1986-12-06 | 花王株式会社 | Alpha-sulfofatty acid ester high concentration aqueous solution |
| DE3538910A1 (en) * | 1985-11-02 | 1987-05-14 | Henkel Kgaa | METHOD FOR PRODUCING MOVABLE PASTE OF WASHING ACTIVE ALPHA SULFOURIC ACID ESTER SALTS HIGH SOLIDS |
-
1989
- 1989-09-14 JP JP1238863A patent/JP2781870B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03101828A (en) | 1991-04-26 |
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