JPS621948B2 - - Google Patents
Info
- Publication number
- JPS621948B2 JPS621948B2 JP12823881A JP12823881A JPS621948B2 JP S621948 B2 JPS621948 B2 JP S621948B2 JP 12823881 A JP12823881 A JP 12823881A JP 12823881 A JP12823881 A JP 12823881A JP S621948 B2 JPS621948 B2 JP S621948B2
- Authority
- JP
- Japan
- Prior art keywords
- oxamide
- bis
- biscyclic
- imino ether
- parts
- 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.)
- Expired
Links
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 22
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- -1 imino ether compound Chemical class 0.000 claims description 11
- 238000000859 sublimation Methods 0.000 claims description 8
- 230000008022 sublimation Effects 0.000 claims description 8
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 8
- KKKKCPPTESQGQH-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=NCCO1 KKKKCPPTESQGQH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- MUAULJMMFLVLHM-UHFFFAOYSA-N n,n'-bis(2-chloroethyl)oxamide Chemical compound ClCCNC(=O)C(=O)NCCCl MUAULJMMFLVLHM-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RLNIFVGPECHGGO-UHFFFAOYSA-N n,n'-bis(3-chloropropyl)oxamide Chemical group ClCCCNC(=O)C(=O)NCCCCl RLNIFVGPECHGGO-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
【発明の詳細な説明】
本発明はビス環状イミノエーテル化合物の合成
法、詳しくは高品質のビス環状イミノエーテル化
合物を収率よく合成する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for synthesizing bis-cyclic imino ether compounds, and more particularly to a method for synthesizing high-quality bis-cyclic imino ether compounds in good yield.
ビス環状イミノエーテル化合物は、カルボキシ
ル基との反応性が極めて高いため、多くの分野で
の利用が考えられる。例えばカルボキシル基を有
する化合物のカツプリング剤、末端カルボキシル
基を有するポリマーの鎖伸長剤として有効と考え
られる。 Since biscyclic iminoether compounds have extremely high reactivity with carboxyl groups, they can be considered for use in many fields. For example, it is considered to be effective as a coupling agent for compounds having a carboxyl group and a chain extender for polymers having a terminal carboxyl group.
しかしながら、ビス環状イミノエーテル化合物
は、その合成が因難で、工業上使用するのに重大
なネツクとなつている。即ち、ビス環状イミノエ
ーテル化合物は、不安定な化合物であつて、水の
存在下加熱すると40℃程度の温度でも分解する傾
向がある。特に、系が酸性又はアルカリ性になる
と、この分離反応は著しく促進される。 However, the synthesis of biscyclic imino ether compounds is difficult, and this poses a serious problem for industrial use. That is, the biscyclic iminoether compound is an unstable compound and tends to decompose even at a temperature of about 40° C. when heated in the presence of water. In particular, this separation reaction is significantly accelerated when the system becomes acidic or alkaline.
従来、ビス環状イミノエーテル化合物の合成法
としては、下記一般式
（式中、Ｘは−CH2・CH2−又は−CH2・
CH2・CH2−を示す）で表わされるＮ，N′−ビス
（クロルアルキル）オキサミド（以下オキサミド
と略称する）を適当な溶媒に懸濁させ、これにオ
キサミドに対し当量またはそれ以上の苛性ソーダ
又は苛性カリウムを添加し、加熱反応させた後反
応混合物を加熱時過して副生した塩化ナトリウ
ム又は塩化カリウムを分離し、次いで液を加熱
濃縮し、しかる後冷却して析出したビス環状イミ
ノエーテル化合物を過により別する方法が知
られている。 Conventionally, the synthesis method for biscyclic imino ether compounds is based on the following general formula: (In the formula, X is -CH 2 · CH 2 - or -CH 2 ·
N,N'-bis(chloralkyl)oxamide (hereinafter referred to as oxamide) represented by CH 2・CH 2 - is suspended in a suitable solvent, and an equivalent or more amount of caustic soda is added to the oxamide. Alternatively, add caustic potassium, heat the reaction, heat the reaction mixture to separate by-produced sodium chloride or potassium chloride, then heat and concentrate the liquid, and then cool to precipitate biscyclic imino ether. Methods of separating compounds by filtration are known.
しかしながら、かかる従来法の問題点は、オキ
サミドとは苛性ソーダ又は苛性カリウムとを反応
させた際に、目的とするビス環状イミノエーテル
化合物以外に塩化物が副成すると同時に、使用し
たオキサミドの２倍当量の水が副生することであ
る。ビス環状イミノエーテル化合物は、上述した
ように加水分解し易く、特にアルカリ性又は酸性
雰囲気下で水が存在すると、この加水分解反応は
急速に進行する。このため、前記従来法では収率
が極めて低く且つ得られるビス環状イミノエーテ
ル化合物の品位も悪い。 However, the problem with this conventional method is that when oxamide is reacted with caustic soda or caustic potassium, chloride is formed as a by-product in addition to the target biscyclic imino ether compound, and at the same time, the amount of chloride that is twice the equivalent of the oxamide used is water is produced as a by-product. As mentioned above, biscyclic imino ether compounds are easily hydrolyzed, and this hydrolysis reaction proceeds rapidly, particularly in the presence of water in an alkaline or acidic atmosphere. Therefore, in the conventional method, the yield is extremely low and the quality of the obtained biscyclic imino ether compound is also poor.
本発明者は、オキサミドと反応させたときに水
を副生ないアルカリという点でナトリウムメチラ
ートに着目し、オキサミドとナトリウムメチラー
トとを反応させてビス環状イミノエーテル化合物
を合成する方法について検討した結果、この方法
によればビス環状イミノエーテル化合物の収率
は、水を副生する前記従来法より有利であること
を確認した。しかしながら、この方法では反応混
合物から、副生した塩化ナトリウムを除去せんと
して加熱時過を試みたところ、目塞りが著しく
過が極めて因難で結局、この方法では反応収率
も品位も向上できなかつた。 The present inventor focused on sodium methylate because it is an alkali that does not produce water as a by-product when reacted with oxamide, and investigated a method for synthesizing a bis-cyclic imino ether compound by reacting oxamide with sodium methylate. As a result, it was confirmed that the yield of biscyclic imino ether compounds according to this method is more advantageous than the above-mentioned conventional method in which water is produced as a by-product. However, when using this method to remove by-product sodium chloride from the reaction mixture, heating was attempted, but the clogging was extremely severe, and in the end, this method was unable to improve the reaction yield and quality. Nakatsuta.
更に、本発明者は高品位のビス環状イミノエー
テル化合物を高収率で合成する方法について鋭意
検討した結果、オキサミドとナトリウムメチラー
トとを反応せしめ、得られた反応生成物からビス
環状イミノエーテル化合物を昇華によつて分離す
れば、目的が達成されることを知り、本発明を達
成した。 Furthermore, as a result of intensive study on a method for synthesizing high-quality bis-cyclic imino ether compounds in high yield, the present inventor reacted oxamide with sodium methylate, and synthesized bis-cyclic imino ether compounds from the resulting reaction product. The present invention was achieved based on the knowledge that the object could be achieved by separating the molecule by sublimation.
即ち、本発明は下記一般式
（式中、Ｘは−CH2・CH2−又は−CH2・
CH2・CH2−を示す）で表わされるＮ，N′−ビス
（クロルアルキル）オキサミドとナトリウムメチ
ラートとを反応せしめ、得られた反応生成物から
ビス環状イミノエーテル化合物を昇華により系外
に取出すことを特徴とするビス環状イミノエーテ
ル化合物の合成法である。 That is, the present invention is based on the following general formula (In the formula, X is -CH 2 · CH 2 - or -CH 2 ·
N,N'-bis(chloralkyl)oxamide represented by CH 2・CH 2 -) is reacted with sodium methylate, and the biscyclic imino ether compound is removed from the system by sublimation from the resulting reaction product. This is a method for synthesizing a biscyclic iminoether compound, which is characterized by the step of extracting the biscyclic iminoether compound.
本発明で使用するＮ，N′−ビス（クロルアル
キル）オキサミドは、具体的には
で示されるＮ，N′−ビス（２−クロルエチル）
オキサミド又は
で示されるＮ，N′−ビス（３−クロルプロピ
ル）オキサミドである。 Specifically, the N,N'-bis(chloralkyl)oxamide used in the present invention is N,N'-bis(2-chloroethyl) represented by
Oxamide or It is N,N'-bis(3-chloropropyl)oxamide shown by
また、本発明で言うビス環状イミノエーテル化
合物は、下記一般式
（式中、Ｘは−CH2・CH2−又は−CH2・
CH2・CH2−を示す）で表わされ、具体的には、
オキサミドとしてＮ，N′−ビス（２−クロルエ
チル）オキサミドを使用したときは、
であり、Ｎ，N′−ビス（２−クロルプロピル）
オキサミドを使用したときは
である。 In addition, the biscyclic imino ether compound referred to in the present invention has the following general formula: (In the formula, X is -CH 2 · CH 2 - or -CH 2 ·
CH 2・CH 2 −), specifically,
When N,N'-bis(2-chloroethyl)oxamide is used as the oxamide, and N,N'-bis(2-chloropropyl)
When using oxamide It is.
オキサミドとナトリウムメチラートとの反応方
式は、粉体のオキサミドと粉体のナトリウムメチ
ラートとを反応せしめる方式でも、オキサミドを
を溶媒に懸濁し、これにナトリウムメチラートを
粉体のまま又はメタノール溶液として添加し撹拌
下及び／又は還流下加熱反応せしめる方式でもよ
いが、反応の容易さ及びより高収率が得られる点
で、後者のオキサミドを溶媒に懸濁する方式が好
ましい。オキサミドを懸濁させる溶媒としては、
例えばメタノール，エタノール，ジオキサン，キ
シレン，トルエン，等をあげることができ、なか
でもメタノールが好ましい。 The reaction method for oxamide and sodium methylate can be one in which powdered oxamide is reacted with powdered sodium methylate, or oxamide is suspended in a solvent, and sodium methylate is added either as a powder or as a methanol solution. Although it is also possible to add the oxamide and heat the reaction under stirring and/or reflux, the latter method in which the oxamide is suspended in a solvent is preferred in terms of ease of reaction and higher yield. As a solvent for suspending oxamide,
Examples include methanol, ethanol, dioxane, xylene, toluene, etc., with methanol being preferred.
オキサミドに反応させるナトリウムメチラート
の量は、オキサミド１モルに対し1.5〜３モルの
範囲が好ましく、なかでも1.8〜2.1モルの範囲が
特に好ましい。反応温度は30〜80℃の範囲が好ま
しく、なかでも50〜70℃の範囲が好ましい。 The amount of sodium methylate reacted with oxamide is preferably in the range of 1.5 to 3 moles, particularly preferably in the range of 1.8 to 2.1 moles, per mole of oxamide. The reaction temperature is preferably in the range of 30 to 80°C, particularly preferably in the range of 50 to 70°C.
本発明にあつては、このようにして得られた粉
体の反応混合物を減圧下加熱してビス環状イミノ
エーテル化合物を昇華によつて取出す。前記反応
が溶媒を使用する方式を採用したときは、得られ
た反応混合物を熱過することなく、加熱により
常圧下又は減圧下蒸発乾固し、得られた粉体を昇
華に供するのが好ましい。昇華の際の減圧度は、
30mmHg以下の高真空が好ましく、なかでも５mm
Hg以下の高真空が特に好ましい。また昇華温度
としては120〜200℃の範囲が好ましく、なかでも
140〜180℃の範囲が特に好ましい。 In the present invention, the powder reaction mixture thus obtained is heated under reduced pressure to extract the biscyclic imino ether compound by sublimation. When the reaction employs a method using a solvent, it is preferable to evaporate the obtained reaction mixture to dryness by heating under normal pressure or reduced pressure without heating, and to subject the obtained powder to sublimation. . The degree of reduced pressure during sublimation is
High vacuum of 30mmHg or less is preferable, especially 5mm
High vacuum below Hg is particularly preferred. In addition, the sublimation temperature is preferably in the range of 120 to 200℃, especially
A temperature range of 140 to 180°C is particularly preferred.
以下に実施例をあげて本発明を更に詳細に説明
する。実施例中の部は重量部を示す。 The present invention will be explained in more detail with reference to Examples below. Parts in Examples indicate parts by weight.
実施例１
Ｎ，N′−ビス（２−クロルエチル）オキサミ
ド10部とナトリウムメチラート4.98部とメタノー
ル12.8部の混合物を65℃で還流下30分間加熱した
後、弱真空にして60℃でメタノールを追出し、得
られた粉体を160℃，１mmHgの真空からなる昇華
設備に入れて60分間昇華した。Example 1 A mixture of 10 parts of N,N'-bis(2-chloroethyl)oxamide, 4.98 parts of sodium methylate, and 12.8 parts of methanol was heated under reflux at 65°C for 30 minutes, and then methanol was evaporated at 60°C under a weak vacuum. The powder thus obtained was placed in a sublimation equipment with a vacuum of 1 mmHg at 160°C and sublimed for 60 minutes.
かくして昇華物として得られた２，2′−ビス
（２−オキサゾリン）は6.1部であつた。この値は
理論収量の93％であつた。また得られた２，2′−
ビス（２−オキサゾリン）の純度は98％であつ
た。 The amount of 2,2'-bis(2-oxazoline) thus obtained as a sublimated product was 6.1 parts. This value was 93% of the theoretical yield. Also obtained 2,2'-
The purity of bis(2-oxazoline) was 98%.
比較例１
Ｎ，N′−ビス（２−クロルエチル）オキサミ
ド10部と水酸化カリウム5.2部とメタノール12.8
部の混合物を65℃で30分間加熱した後、この温度
のまま熱時過を行い、塩化カリウムを除き、
液を弱真空にしてメタノールを８部追出し、次い
で１℃まで冷却し、析出した針状結晶を別し
た。得られた２，2′−ビス（２−オキサゾリン）
の結晶は4.9部であり、この値は理論値の69％で
あつた。また得られた２，2′−ビス（２−オキサ
ゾリン）の純度は88％であり、そのままでは使用
できないものであつた。Comparative Example 1 10 parts of N,N'-bis(2-chloroethyl)oxamide, 5.2 parts of potassium hydroxide, and 12.8 parts of methanol
After heating the mixture at 65℃ for 30 minutes, heat aging was carried out at this temperature to remove potassium chloride.
The liquid was evacuated to a weak vacuum to expel 8 parts of methanol, then cooled to 1°C, and the precipitated needle crystals were separated. Obtained 2,2'-bis(2-oxazoline)
The amount of crystals was 4.9 parts, which was 69% of the theoretical value. Moreover, the purity of the obtained 2,2'-bis(2-oxazoline) was 88%, and it could not be used as it was.
比較例２
比較例１において水酸化カリウムをナトリウム
メチラート4.98部にかえる以外は比較例１と全く
同一操作で得た２，2′−ビス（２−オキサゾリ
ン）は5.2部であつた。また得られた２，2′−ビ
ス（２−オキサゾリン）の純度は91％であり、こ
のままでは使用できないものであつた。Comparative Example 2 2,2'-bis(2-oxazoline) was obtained in exactly the same manner as in Comparative Example 1 except that 4.98 parts of sodium methylate was used instead of potassium hydroxide.The amount of 2,2'-bis(2-oxazoline) was 5.2 parts. The purity of the obtained 2,2'-bis(2-oxazoline) was 91%, and it could not be used as it was.
Claims (1)
CH2・CH2−を示す）で表わされるＮ，N′−ビス
（クロルアルキル）オキサミドとナトリウムメチ
ラートとを反応せしめ、得られた反応生成物から
ビス環状イミノエーテル化合物を昇華により系外
に取出すことを特徴とするビス環状イミノエーテ
ル化合物の合成法。[Claims] 1. The following general formula (In the formula, X is -CH 2 · CH 2 - or -CH 2 ·
N,N'-bis(chloralkyl)oxamide represented by CH 2・CH 2 -) is reacted with sodium methylate, and the biscyclic imino ether compound is removed from the system by sublimation from the resulting reaction product. 1. A method for synthesizing a biscyclic iminoether compound, which is characterized by the step of extracting a biscyclic iminoether compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12823881A JPS5832869A (en) | 1981-08-18 | 1981-08-18 | Synthesis of biscyclic iminoether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12823881A JPS5832869A (en) | 1981-08-18 | 1981-08-18 | Synthesis of biscyclic iminoether compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5832869A JPS5832869A (en) | 1983-02-25 |
| JPS621948B2 true JPS621948B2 (en) | 1987-01-16 |
Family
ID=14979902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12823881A Granted JPS5832869A (en) | 1981-08-18 | 1981-08-18 | Synthesis of biscyclic iminoether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5832869A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1229490B (en) * | 1988-12-23 | 1991-09-03 | Enichem Anic Spa | SUMMARY OF 2, 2'DELTA2- -BIS-OSSAZOLINA |
-
1981
- 1981-08-18 JP JP12823881A patent/JPS5832869A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5832869A (en) | 1983-02-25 |
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