JPH01172427A - Modification of polyarylene sulfide amide polymer - Google Patents
Modification of polyarylene sulfide amide polymerInfo
- Publication number
- JPH01172427A JPH01172427A JP62329823A JP32982387A JPH01172427A JP H01172427 A JPH01172427 A JP H01172427A JP 62329823 A JP62329823 A JP 62329823A JP 32982387 A JP32982387 A JP 32982387A JP H01172427 A JPH01172427 A JP H01172427A
- Authority
- JP
- Japan
- Prior art keywords
- polyarylene sulfide
- group
- amide polymer
- sulfide amide
- formulas
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 24
- 229920000412 polyarylene Polymers 0.000 title claims abstract description 13
- -1 sulfide amide Chemical class 0.000 title claims abstract description 13
- 230000004048 modification Effects 0.000 title 1
- 238000012986 modification Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004734 Polyphenylene sulfide Substances 0.000 description 4
- 229920000069 polyphenylene sulfide Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005486 sulfidation Methods 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000001955 polymer synthesis method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はポリアリーレンスルフィドアミド重合体の改質
方法に関するものである。本発明により、本来優れた耐
熱性を有するポリアリーレンスルフィドアミド重合体の
耐溶剤性を向上させ、より幅広い分野への応用を可能と
するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for modifying polyarylene sulfide amide polymers. The present invention improves the solvent resistance of a polyarylene sulfide amide polymer, which inherently has excellent heat resistance, and enables its application to a wider range of fields.
〈従来の技術〉
アミド基及びチオエーテル基を介してフエニレン基及び
アルキレン基が連結されているポリアリーレンスルフィ
ドアミド重合体は優れた耐熱性を有するため、その工業
分野への応用が期待される。<Prior Art> Polyarylene sulfide amide polymers in which phenylene groups and alkylene groups are linked via amide groups and thioether groups have excellent heat resistance, and are therefore expected to be applied to industrial fields.
しかし逆に融点が高く通常の溶融成形が不可能である。However, it has a high melting point and cannot be melt-molded.
この重合体の成形を行うにあたっては、濃硫酸・ＮＭＰ
等、一部の溶媒に可溶であることを利用してキャスト法
が第一に考えられる。しかし、耐溶剤性を必要とする分
野への応用は制限されざるを得ない。When molding this polymer, concentrated sulfuric acid/NMP
The first option is to use the casting method, which takes advantage of the fact that it is soluble in some solvents. However, its application to fields requiring solvent resistance is inevitably limited.
〈発明が解決しようとする問題点〉
本発明はこの要望に答えるべく鋭意研究の結果、ポリア
リーレンスルフィドアミド重合体を本来の耐熱性を保持
したまま耐溶剤性を向上させる、すなわちポリアリーレ
ンスルフィドアミド重合体の改質方法を提供することに
ある。<Problems to be Solved by the Invention> As a result of intensive research in order to meet this demand, the present invention has been developed to improve the solvent resistance of polyarylene sulfide amide polymers while retaining their original heat resistance. An object of the present invention is to provide a method for modifying a polymer.
く問題点を解決するための手段〉
本発明は、下式（１）、 （■）及び（ＩＩＩ）から
選ばれる少なくとも１種の繰返し単位から成る、ポリア
リーレンスルフィドアミド重合体を１５０〜４００℃の
範囲において加熱処理することを特徴とするその物性を
改質する方法にある。Means for Solving the Problems> The present invention provides a polyarylene sulfide amide polymer comprising at least one type of repeating unit selected from the following formulas (1), (■), and (III) at a temperature of 150 to 400°C. A method for modifying the physical properties of a material, characterized by heat treatment in the range of .
［式中Ａｒ１〜Ａ「１０は芳香族環を示しＲ１−Ｒ１４
は炭素数１〜２０のアルキル基、炭素数３〜２０のシク
ロアルキル基、炭素数６〜２０のアリール基、炭素数１
〜２０のアルコキシ基、炭素数２〜２０のアシル基又は
炭素数７〜２０のアリールアルキル基を表わし、それぞ
れ同一あるいは異なっていても良いｏ ａｎ ｂ＋
Ｃ＋ ｄ＊ ｅ＋ ｆ＋ ｇ。[In the formula, Ar1 to A"10 represents an aromatic ring and R1 to R14
is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 1 carbon number.
~20 alkoxy group, acyl group having 2 to 20 carbon atoms, or arylalkyl group having 7 to 20 carbon atoms, each of which may be the same or different o an b+
C+ d* e+ f+ g.
ｈ＋ Ｌ Ｊは互いに同一、あるいは異なる０〜４
の整数を示す。またＲ１１〜Ｒ１４は水素、であっても
良い。Ｒ１５，ＲｌＢ、 Ｒ１７は炭素数１〜２０のア
ルキレン基を表わしそれぞれ同一あるいは異なっていて
も良い。又、ｐ／ｑ、 ｐ’ ／ｑ’ 、 ｐ”／
ｑ”はそれぞれ１００１０〜１／９９の範囲である。］
以下本発明の詳細な説明する。h+L J are the same or different from 0 to 4
indicates an integer. Further, R11 to R14 may be hydrogen. R15, RlB, and R17 represent alkylene groups having 1 to 20 carbon atoms, and may be the same or different. Also, p/q, p'/q', p''/
q'' is in the range of 10010 to 1/99, respectively.] The present invention will be described in detail below.
本発明で対象とされるポリアリーレンスルフィ（Ｚは−
ｏ−、−ｓ−、−５ｏ２−、−ｃｏ−。Polyarylene sulfuric acid (Z is -
o-, -s-, -5o2-, -co-.
等が挙げられ、それぞれ同一あるいは異なっても良い。etc., and they may be the same or different.
その好ましい（Ｉ）、（ＩＩ）、（ＩＩＩ）の繰返し単
位の具体例としては以下のものが挙げられる。Specific examples of the preferred repeating units (I), (II), and (III) include the following.
これらアミド基含有化合物は耐熱性の面ではパラ位の結
合から成ることが好ましいが、得られるスルフィドアミ
ド重合体の成形性を向上するためにはメタ位及び／又は
オルト位の結合を含ませたり、分岐構造を取るほうが良
い。These amide group-containing compounds preferably consist of bonds in the para position from the viewpoint of heat resistance, but in order to improve the moldability of the resulting sulfide amide polymer, it is preferable to include bonds in the meta and/or ortho positions. , it is better to take a branched structure.
次に熱処理の具体的条件は１５０〜４００℃の範囲にお
いて１〜１２時間、好ましくは２００〜３００℃の範囲
において１〜６時間で行うのが良い。また、酸素存在下
で処理を行うほうが時間を短縮するうえで好ましい。Next, the specific conditions for heat treatment are preferably 1 to 12 hours at a temperature of 150 to 400°C, preferably 1 to 6 hours at a temperature of 200 to 300°C. Further, it is preferable to perform the treatment in the presence of oxygen in order to shorten the time.
これまでスルフィド化剤を用いスルフィド化して合成し
たＰＰＳ （ポリフェニレンスルフィド）は加熱処理す
ることで見かけ上の分子量を上昇させていたが、耐溶剤
性に関しては顕著な変化が見られなかった。ポリアリー
レンスルフィドアミド重合体においては加熱処理するだ
けで耐溶剤性が顕著に向上した。この現象は本発明で新
たに判明した事実である。Until now, the apparent molecular weight of PPS (polyphenylene sulfide) synthesized by sulfidation using a sulfidation agent was increased by heat treatment, but no significant change was observed in terms of solvent resistance. Solvent resistance of polyarylene sulfide amide polymers was significantly improved simply by heat treatment. This phenomenon is a newly discovered fact in the present invention.
この方法を利用すると、例えばキャスト法でフィルム・
繊維に加工したり、塗装した後、加熱処理することによ
って不溶不融とし、高耐熱性・耐溶剤性を要求される分
野へも適応可能となる。従ってこれまでＰＰＳ （ポリ
フェニレンスルフィド）に代表されるイオウ系のエンプ
ラとは異なった、新たな用途への展開も考えられる。Using this method, you can, for example, use the casting method to
After being processed into fibers or painted, it is heat-treated to make it insoluble and infusible, making it applicable to fields that require high heat resistance and solvent resistance. Therefore, it is conceivable that it could be used for new purposes, different from the sulfur-based engineering plastics typified by PPS (polyphenylene sulfide).
［実施例］
以下、本発明を実施例によって具体的に説明するが、本
発明はこれらの実施例のみ限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited only to these Examples.
使用したポリマーの合成法
５００ｍ１容量のオートクレーブにＮ ａ ２ Ｓ・２
、 ７Ｈ２００，０４ｍｏ ｌ、 Ｎ−メチル−２−ピ
ロリドン（ＮＭＰ）１５０ｍｌを入れ撹拌しながら２０
０℃まで昇温し、脱水を行った。反応系を１００℃まで
冷却した後アミド基を含有するジハロゲン化合物０．０
４ｍｏｌをＮＭＰ ５０ｍｌとともに添加し、系を封入
昇温しで２５０℃で６時間重合した。Polymer synthesis method used: Na 2 S・2 in an autoclave with a capacity of 500 ml.
, 200.04 mol of 7H, and 150 ml of N-methyl-2-pyrrolidone (NMP) were added while stirring.
The temperature was raised to 0°C and dehydration was performed. After cooling the reaction system to 100°C, 0.0% of the dihalogen compound containing an amide group was added.
4 mol was added together with 50 ml of NMP, and the system was sealed and heated to 250° C. for 6 hours to polymerize.
反応終了後、系を冷却しメタノールを加えてポリマーを
析出させた。ろ過した後温水で洗浄、ろ過を繰返し乾燥
して粉末状ポリマーを得た。After the reaction was completed, the system was cooled and methanol was added to precipitate the polymer. After filtration, washing with warm water and filtration were repeated and drying to obtain a powdery polymer.
このポリマーの赤外吸収（ＩＲ）スペクトルを測定した
ところ１０９０ｃｍ−１付近にチオエーテル結合に由来
する吸収が、３３５０．１６４０゜１５４０ｃ＋ｏ−’
付近にアミド結合に由来する吸収が見られた。When the infrared absorption (IR) spectrum of this polymer was measured, an absorption derived from the thioether bond was observed near 1090 cm-1 at 3350.1640°1540c+o-'
Absorption derived from amide bonds was observed nearby.
比較例 １
重合後熱処理をしない次の構造を有するポリマ０１（Ｈ
Ｏ
テストはメタノール・ピリジン（Ｐ ｙ） ・ジメチル
ホルムアミド（ＤＭＦ） ・ジメチルスルホキシド（Ｄ
ＭＳＯ） ・Ｎ−メチル−ピロリドン（ＮＭＰ）・Ｌ
ｉＣｌ／ＮＭＰ溶液・濃硫酸で行った。Comparative Example 1 Polymer 01 (H
O The test is methanol, pyridine (Py), dimethylformamide (DMF), dimethyl sulfoxide (D
MSO) ・N-methyl-pyrrolidone (NMP) ・L
It was performed using iCl/NMP solution/concentrated sulfuric acid.
＋＋＋＋＋＋＋
＋ 可溶 士 難溶 −不溶 （目視により判断
）
実施例 １
上記ポリマーを空気雰囲気下、オーブン中（２５０℃）
で１〜４時間熱処理した後の溶解度テストは次の通りで
ある。＋＋＋＋＋＋＋ Soluble Poorly soluble - Insoluble (Judged visually) Example 1 The above polymer was placed in an oven (250°C) in an air atmosphere.
The solubility test after heat treatment for 1 to 4 hours is as follows.
１時間 −−士 士 ＋ ＋ 十２時間
−−−−± ＋ ＋
３時間 −−一一一 −±
十 可溶 士 難溶 −不溶（目視により判断）実
施例 ２
上記ポリマーを空気雰囲気下、オーブン中（１５０〜３
００℃）で２時間熱処理した後の溶解度テストは次の通
りである。1 hour ---Certified + + 12 hours
−−−−± + + 3 hours −−111 −± 10 Soluble Poorly soluble −Insoluble (determined by visual inspection) Example 2 The above polymer was placed in an oven under an air atmosphere (150 to 3
The solubility test after heat treatment at 00°C for 2 hours is as follows.
１５０ ℃ −−＋ 十＋ ＋
十２００ ℃ −−士 士 士
十 ＋２５０℃−一一一±＋ ＋
３００℃−一一一一一 ±
十 可溶 士 難溶 −不溶（目視により判断）比
較例 ２
別のポリマーにおいても溶解度テストを行った。熱処理
前の結果は次の通りである。150℃ −−+ 10+ +
1200 degrees Celsius
+250°C-111±+ +300°C-1111±10 Soluble Poorly soluble - Insoluble (determined by visual observation) Comparative Example 2 A solubility test was also conducted on another polymer. The results before heat treatment are as follows.
ｎｌｌ０
＋ 可溶 士 難溶 −不溶（目視により判断）実
施例 ３
上記各種ポリマーを空気雰囲気下で２５０℃、２時間熱
処理した時の各溶媒に対する溶解度は次の通りである。nll0 + Soluble Poorly soluble - Insoluble (determined visually) Example 3 The solubility in each solvent when the above various polymers were heat treated at 250° C. for 2 hours in an air atmosphere is as follows.
ＨＩＩＯ
十 可溶 士 難溶 −不溶（目視により判断）〈
発明の効果〉
以上の説明から明らかなように、本発明によれば従来ポ
リイミド等の限られた構造をもつ高分子しか使用できな
かった高耐熱性・耐溶剤性を要求される分野へも新たに
ポリアリーレンスルフィドアミド重合体の適用が期待さ
れる。HIIO 10 Soluble Poorly soluble - Insoluble (determined by visual inspection)
Effects of the Invention> As is clear from the above explanation, the present invention can be applied to fields requiring high heat resistance and solvent resistance, where conventionally only polymers with limited structures such as polyimide could be used. Polyarylene sulfide amide polymers are expected to be applied to
Claims (1)
くとも１種の繰返し単位から成るポリアリーレンスルフ
ィドアミド重合体を１５０〜４００℃の範囲において加
熱処理することを特徴とするポリアリーレンスルフィド
アミド重合体の改質方法。 ▲数式、化学式、表等があります▼（ I ） ▲数式、化学式、表等があります▼（II） ▲数式、化学式、表等があります▼（III） ［式中Ａｒ＾１〜Ａｒ＾１＾０は芳香族環を示しＲ＾１
〜Ｒ＾１＾４は炭素数１〜２０のアルキル基、炭素数３
〜２０のシクロアルキル基、炭素数６〜２０のアリール
基、炭素数１〜２０のアルコキシ基、炭素数２〜２０の
アシル基又は炭素数７〜２０のアリールアルキル基を表
わし、それぞれ同一あるいは異なっていても良い。ａ、
ｂ、ｃ、ｄ、ｅ、ｆ、ｇ、ｈ、ｉ、ｊは互いに同一、あ
るいは異なる０〜４の整数を示す。またＲ＾１＾１〜Ｒ
＾１＾４は水素であっても良い。Ｒ＾１＾５、Ｒ＾１＾
６、Ｒ＾１＾７は炭素数１〜２０のアルキレン基を表わ
しそれぞれ同一あるいは異なっていても良い。又、ｐ／
ｑ、ｐ′／ｑ′、ｐ″／ｑ″はそれぞれ１００／０〜１
／９９の範囲である。］[Claims] 1) Heat treating a polyarylene sulfide amide polymer comprising at least one type of repeating unit selected from the following formulas (I), (II) and (III) at a temperature in the range of 150 to 400°C. A method for modifying a polyarylene sulfide amide polymer, characterized by: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) [In the formula, Ar^1 ~ Ar^1^ 0 indicates an aromatic ring and R^1
~R^1^4 is an alkyl group having 1 to 20 carbon atoms, and 3 carbon atoms
~20 cycloalkyl group, C6-20 aryl group, C1-20 alkoxy group, C2-20 acyl group, or C7-20 arylalkyl group, each of which is the same or different. You can leave it there. a,
b, c, d, e, f, g, h, i, and j are integers of 0 to 4 that are the same or different from each other. Also R^1^1~R
^1^4 may be hydrogen. R^1^5, R^1^
6, R^1^7 represents an alkylene group having 1 to 20 carbon atoms, and may be the same or different. Also, p/
q, p'/q', p''/q'' are each 100/0 to 1
/99 range. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62329823A JPH0739492B2 (en) | 1987-12-28 | 1987-12-28 | Method for modifying polyarylene sulfide amide polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62329823A JPH0739492B2 (en) | 1987-12-28 | 1987-12-28 | Method for modifying polyarylene sulfide amide polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01172427A true JPH01172427A (en) | 1989-07-07 |
| JPH0739492B2 JPH0739492B2 (en) | 1995-05-01 |
Family
ID=18225628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62329823A Expired - Fee Related JPH0739492B2 (en) | 1987-12-28 | 1987-12-28 | Method for modifying polyarylene sulfide amide polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739492B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921396A (en) * | 2010-07-29 | 2010-12-22 | 四川大学 | Semi-aryl poly (phenylene sulfide amide) and preparation method thereof |
| CN102532532A (en) * | 2011-12-21 | 2012-07-04 | 四川大学 | Thioether-containing semi-aromatic polyamide and preparation method thereof |
-
1987
- 1987-12-28 JP JP62329823A patent/JPH0739492B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921396A (en) * | 2010-07-29 | 2010-12-22 | 四川大学 | Semi-aryl poly (phenylene sulfide amide) and preparation method thereof |
| CN102532532A (en) * | 2011-12-21 | 2012-07-04 | 四川大学 | Thioether-containing semi-aromatic polyamide and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0739492B2 (en) | 1995-05-01 |
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