JPS6392619A - O-(trialkylsilyl)phenylacetylene polymer and its production - Google Patents
O-(trialkylsilyl)phenylacetylene polymer and its productionInfo
- Publication number
- JPS6392619A JPS6392619A JP23842186A JP23842186A JPS6392619A JP S6392619 A JPS6392619 A JP S6392619A JP 23842186 A JP23842186 A JP 23842186A JP 23842186 A JP23842186 A JP 23842186A JP S6392619 A JPS6392619 A JP S6392619A
- Authority
- JP
- Japan
- Prior art keywords
- phenylacetylene
- trialkylsilyl
- polymer
- group
- transition metal
- 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 37
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 9
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 239000012528 membrane Substances 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 5
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 abstract description 2
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 abstract description 2
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- SKRALBDPWWULBT-UHFFFAOYSA-N (2-ethynylphenyl)-trimethylsilane Chemical group C[Si](C)(C)C1=CC=CC=C1C#C SKRALBDPWWULBT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 101150030723 RIR2 gene Proteins 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- FQNHWXHRAUXLFU-UHFFFAOYSA-N carbon monoxide;tungsten Chemical group [W].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] FQNHWXHRAUXLFU-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、気体分離膜材料、電気・電子材料等アル〜
として有用である新規な０−（トリ→ルシリル）フェニ
ルアセチレン重合体およびその製法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides a novel 0-(tri→rusilyl)phenylacetylene polymer useful as a material for gas separation membranes, electrical/electronic materials, etc., and a method for producing the same. Regarding.
従来、−置換フェニルアセチレン誘導体の重合体として
は、例えば、フェニルアセチレン重合体、０−メチルフ
ェニルアセチレン重合体などが知られている（Ｐｏｌｙ
ｍｅｒ Ｐｒｅｐｒｉｎｔｓ＋ Ｊａｐａｒ＋＋ ３５
＋ ２２８（１９８６））が、分子量が数万〜十数万と
小さいため膜などへの成形加工が困難であり、得られる
膜は熱安定性および機械的強度が低いという問題点を存
している。Conventionally, as polymers of -substituted phenylacetylene derivatives, for example, phenylacetylene polymers, 0-methylphenylacetylene polymers, etc. are known (Poly
mer Preprints+ Japar++ 35
+228 (1986)), but because the molecular weight is small, ranging from tens of thousands to hundreds of thousands, it is difficult to form into films, etc., and the resulting films have the problem of low thermal stability and mechanical strength. There is.
そこで、本発明の目的は、分子量が高く、有機溶媒に可
溶性であり、製膜性等の成形加工性に優れ、熱安定性、
機械的強度の高い膜を作製できる一ｉ換フェニルアセチ
レン重合体を提供することにあり、さらに別の目的は、
このような重合体を比較的短時間で重合でき、かつ高収
率で製造することができる製法を提供することにある。Therefore, the object of the present invention is to have a high molecular weight, soluble in organic solvents, excellent molding processability such as film forming property, thermal stability,
Another object of the present invention is to provide a monovalent phenylacetylene polymer capable of producing a membrane with high mechanical strength.
The object of the present invention is to provide a manufacturing method that can polymerize such a polymer in a relatively short time and at a high yield.
本発明は前記の問題点を解決するものとして、一般式（
１）
〔式中、Ｒ１，Ｒ１およびＲ３は、同一でも異なっても
よく、低級アルキル基を表わし、ｎは繰返し単位の繰返
し数を表わす整数である。〕
で表わされる０ −（）リアルキルシリル）フェニルア
セチレン重合体を提供するものである。The present invention solves the above-mentioned problems by the general formula (
1) [In the formula, R1, R1 and R3 may be the same or different and represent a lower alkyl group, and n is an integer representing the number of repeating units. ] An 0-()alkylsilyl)phenylacetylene polymer represented by the following is provided.
また、本発明は、一般式（ｎ）
〔式中、Ｒ１，ＲＺおよびＲ３は前記に定義のとおりで
ある〕
で表わされるｏ−（トリアルキルシリル）フェニルアセ
チレンを、第■族遷移金属化合物の存在下で重合させる
ことからなる前記一般式（Ｉ）で表わされる〇−（トリ
アルキルシリル）フェニルアセチレン重合体の製法を提
供するものである。Further, the present invention provides o-(trialkylsilyl)phenylacetylene represented by the general formula (n) [wherein R1, RZ and R3 are as defined above] as a Group I transition metal compound. The present invention provides a method for producing a 〇-(trialkylsilyl)phenylacetylene polymer represented by the general formula (I), which comprises polymerizing in the presence of the above-mentioned general formula (I).
前記の一般式（１）および（ＩＩ）において、ＲＩＲ２
およびＲ３が表わす低級アルキル基としては、例えば、
メチル、エチル、プロピル等が挙げられる。In the above general formulas (1) and (II), RIR2
The lower alkyl group represented by R3 is, for example,
Examples include methyl, ethyl, propyl and the like.
本発明の重合体の製法に用いられる第■族遷移金属とし
ては、クロム、モリブデンおよびタングステンが挙げら
れ、触媒として使用される第■族遷移金属化合物の具体
例としては、五塩化モリブデン（ＭｏＣ１，） 、六塩
化タングステン等の塩化物；クロムカルボニル、モリ゛
ブデンカルポニルおよびタングステンカルボニルの金属
カルボニルとを機ハロゲン化物、例えば四塩化炭素、ト
リクロロ酢酸エチル等との混合物に紫外線などの光照射
して得られる物質等を挙げることができる。これらの触
媒は、単量体である０−（トリアルキルシリル）フェニ
ルアセチレン１００モルに対し０．２〜５モルの範囲で
使用するのが適当である。Examples of Group Ⅰ transition metals used in the method for producing the polymer of the present invention include chromium, molybdenum, and tungsten. Specific examples of Group Ⅰ transition metal compounds used as catalysts include molybdenum pentachloride (MoC1, ), chlorides such as tungsten hexachloride; metal carbonyls such as chromium carbonyl, molybdenum carbonyl, and tungsten carbonyl are obtained by irradiating a mixture of halides such as carbon tetrachloride, ethyl trichloroacetate, etc. with light such as ultraviolet rays. Examples include substances that can be used. These catalysts are suitably used in an amount of 0.2 to 5 moles per 100 moles of the monomer 0-(trialkylsilyl)phenylacetylene.
また、本発明の製法では、上記の第■族遷移金属化合物
に還元剤を併用することが好ましく、還元剤を併用する
ことにより前記触媒の作用を助長することができ、より
高分子量の重合体を得るのに有利である。使用すること
ができる還元剤としては、例えばテトラフェニルスズ、
テトラｎ−ブチルスズ、トリフェニルシラン、トリエチ
ルシラン、トリフェニルアンチモン、トリフェニルビス
マス等の有機金属化合物および金属水素化物などを挙げ
ることができる。この還元剤の使用量は、前記の第■族
遷移金属化合物１モルに対し０．３〜３モルの範囲が好
ましい。In addition, in the production method of the present invention, it is preferable to use a reducing agent in combination with the above-mentioned Group Ⅰ transition metal compound, and by using the reducing agent in combination, the action of the catalyst can be promoted, and a polymer with a higher molecular weight can be produced. It is advantageous to obtain Reducing agents that can be used include, for example, tetraphenyltin,
Examples include organometallic compounds and metal hydrides such as tetra-n-butyltin, triphenylsilane, triethylsilane, triphenylantimony, and triphenylbismuth. The amount of this reducing agent used is preferably in the range of 0.3 to 3 moles per mole of the Group I transition metal compound.
本発明の製法における重合反応は、通常、有機溶媒中で
行なわれる。有機溶媒としては、ヘンゼン、トルエン等
の炭化水素；四塩化炭素等のハロゲン化炭化水素等が挙
げられる。The polymerization reaction in the production method of the present invention is usually carried out in an organic solvent. Examples of the organic solvent include hydrocarbons such as Hensen and toluene; halogenated hydrocarbons such as carbon tetrachloride.
重合反応においては、単量体である０−（トリアルキル
シリル）フェニルアセチレンの濃度は０．１〜５モル／
ｉの範囲が好ましく、反応温度は一５〜８０℃が好まし
いが、得られる重合体の分子量と収率が向上する点で特
に、０〜４０″Ｃが好ましい。反応時間は、通常数十分
〜数十時間である。In the polymerization reaction, the concentration of the monomer 0-(trialkylsilyl)phenylacetylene is 0.1 to 5 mol/
A range of i is preferable, and the reaction temperature is preferably -5 to 80 degrees Celsius, but 0 to 40 degrees Celsius is particularly preferable in terms of improving the molecular weight and yield of the obtained polymer.The reaction time is usually several tens of minutes. ~ several dozen hours.
上記の重合反応により、−ｉ式（Ｉ）で表わされる重合
体を含む反応混合物が得られるが、該反応混合物を反応
に用いた有機溶媒で希釈した後大量のメタノールの中に
投入することにより、生成重合体が沈殿するので濾別に
より回収することができる。Through the above polymerization reaction, a reaction mixture containing the polymer represented by the -i formula (I) is obtained, but by diluting the reaction mixture with the organic solvent used in the reaction and then pouring it into a large amount of methanol. , the produced polymer precipitates and can be recovered by filtration.
こうして得られる一般式＜１）の０−（トリアルキルシ
リル）フェニルアセチレン重合体は、通常、一般式（Ｉ
）におけるｎがおよそ１００〜２０．０００であり、分
子量がｔｏ、０００〜３，０００，０００程度である。The 0-(trialkylsilyl)phenylacetylene polymer of the general formula <1) thus obtained is usually the general formula (I
) is about 100 to 20,000, and the molecular weight is about 000 to 3,000,000.
〔実施例〕 次に本発明を実施例により具体的に説明する。〔Example〕 Next, the present invention will be specifically explained using examples.
実施例１
乾燥窒素雰囲気下で充分精製したトルエン１１！中に六
塩化タングステン１０ミリモルを加え、溶解し、次にｏ
−（トリメチルシリル）フェニルアセチレン１．０モル
を添加し、３０℃で２４時間重合させた。得られた反応
混合物を過剰のメタノール中に投入して生成重合体を沈
殿させ、濾別、乾燥した。Example 1 Toluene 11 sufficiently purified under a dry nitrogen atmosphere! Add 10 mmol of tungsten hexachloride into the solution, dissolve, and then o
1.0 mol of -(trimethylsilyl)phenylacetylene was added and polymerized at 30°C for 24 hours. The resulting reaction mixture was poured into excess methanol to precipitate the produced polymer, which was filtered and dried.
メタノール不溶性重合体の収率は、単量体の仕込量に対
し９１％であり、得られた重合体の分子量をゲルパーミ
ェーションクロマトグラフィーで測定したところ、ポリ
スチレン換算での重量平均分子量が１５０万であった。The yield of the methanol-insoluble polymer was 91% based on the amount of monomer charged, and when the molecular weight of the obtained polymer was measured by gel permeation chromatography, the weight average molecular weight in terms of polystyrene was It was 1.5 million.
なお、得られた重合体は黒紫色であり、電気伝導度は４
Ｘｌ０−”５７ｃｍ、 １２０℃で２０時間空気中
で加熱した時の熱安定性は、α＝２．０ Ｘｌ０−’
（なお、α＝（１／Ｕ下下’Ｉ −（１／丁ｒ丁コ）、
■丁丁コおよびコ１はそれぞれ加熱前と後における重合
体の数平均重合度である）であった。The obtained polymer has a blackish-purple color and an electrical conductivity of 4.
Xl0-'57cm, thermal stability when heated in air at 120℃ for 20 hours is α=2.0 Xl0-'
(In addition, α=(1/U下下'I -(1/Ding r Ding),
(2) ding ding ko and ko 1 are the number average degree of polymerization of the polymer before and after heating, respectively).
生成重合体をトルエンに溶解し、濾過後平滑面上に流延
し、乾燥させることにより丈夫な膜を得た。得られた膜
の気体透過性を測定したところ、酸素透過係数はＰ Ｏ
ｘ ＝８．９ Ｘｌ０−’ｃｎ（ＳＴＰ） ・ｃｍ／
ａｄ・３ｅ（−ｃｍＨｇであり、酸素と窒素の透過係数
比はＰ ｏｚ ／ Ｐ ｎｚ＝３．３であった。The resulting polymer was dissolved in toluene, filtered, cast on a smooth surface, and dried to obtain a strong membrane. When the gas permeability of the obtained membrane was measured, the oxygen permeability coefficient was P O
x = 8.9 Xl0-'cn(STP) ・cm/
ad·3e (-cmHg), and the permeability coefficient ratio of oxygen and nitrogen was Poz/Pnz=3.3.
得られた重合体の赤外吸収スペクトルを第１図に示す。The infrared absorption spectrum of the obtained polymer is shown in FIG.
次の吸収がみられた。The following absorption was observed.
３０５０、１４６５ （ａｍ−’） ＝・ＣＨ＝ Ｃに
基づく吸収、１２４５、８３５．７５０ （ｃｍ−’）
＝−Ｓｉ（ＣＨｔ）ｓに基づく吸収、
７２０ （ｃｍ−’）・・・ベンゼン環に基づく吸収。3050, 1465 (am-') =・CH= Absorption based on C, 1245, 835.750 (cm-')
= Absorption based on -Si(CHt)s, 720 (cm-')...Absorption based on benzene ring.
また、得られた重合体の元素分析の結果は、次のとおり
であった。Further, the results of elemental analysis of the obtained polymer were as follows.
計算値： （ＣｚＨ＋４Ｓｉ）、としてＨ： ８．１０
％、Ｃ： ７５．７９％、Ｓｉ： １６．１１％
実測値：Ｈ：８．０３％、Ｃ： ７５．９４％、ｓｉ
： １６．０３％
実施例２〜１０
実施例１において、六塩化タングステンの代りに第１表
に示す触媒を用いたほかに、実施例２〜７および１０に
おいては第１表に示す還元剤を１０ミリモル使用し、ま
た実施例８においては溶媒としてトルエンの代りに四塩
化炭素を１１用いた以外は、実施例１と同様にしてｏ−
（トリメチルシリル）フェニルアセチレンの重合を行な
った。Calculated value: (CzH+4Si), H: 8.10
%, C: 75.79%, Si: 16.11% Actual value: H: 8.03%, C: 75.94%, si
: 16.03% Examples 2 to 10 In Example 1, the catalyst shown in Table 1 was used instead of tungsten hexachloride, and in Examples 2 to 7 and 10, the reducing agent shown in Table 1 was used. o-
(Trimethylsilyl)phenylacetylene was polymerized.
得られた重合体の収率とポリスチレン換算の重量平均分
子量を第１表に示す。Table 1 shows the yield of the obtained polymer and the weight average molecular weight in terms of polystyrene.
第 １ 表
φυ ＊−（■）６と四塩（？Ｊ心盪容夜に光を照射し
て得られた物質。Table 1 Substances obtained by irradiating light on φυ *-(■) 6 and 4 salts (?J).
〔発明の効果〕
本発明の新規重合体は、１０，０００以上の高い分子量
を有するもので、しかも有機溶媒に可溶性であるため、
製膜性等の成形加工性に優れている。該重合体は高い気
体透過性を有し、成形体の機械的強度が大きいので、気
体透過性膜、特に例えば空気から酸素を分離するなどの
気体分離膜として有用である。またこの重合体は耐熱安
定性に優れており、高温下に置かれる場所においても使
用することができる。さらに、本発明の重合体は、その
まま絶縁材料として、またドーパントを加えて導電材料
として、種々の用途に電気、電子材料としても有用であ
る。[Effects of the Invention] The novel polymer of the present invention has a high molecular weight of 10,000 or more and is soluble in organic solvents.
Excellent formability such as film forming properties. Since the polymer has high gas permeability and the mechanical strength of the molded product is high, it is useful as a gas permeable membrane, particularly as a gas separation membrane, for example, for separating oxygen from air. Furthermore, this polymer has excellent heat resistance stability and can be used even in places exposed to high temperatures. Furthermore, the polymer of the present invention is useful as an insulating material as it is, or as a conductive material with the addition of a dopant, and as an electrical and electronic material for various uses.
また、本発明の重合体の製法によると、かかる有用な新
規重合体を比較的短い重合時間で高収率で得ることがで
きる。Moreover, according to the method for producing a polymer of the present invention, such a useful new polymer can be obtained in a high yield in a relatively short polymerization time.
第１図は、実施例１で得られたｏ−（トリメチルシリル
）フェニルアセチレン重合体の赤外吸収スペクトルを表
わす。FIG. 1 shows an infrared absorption spectrum of the o-(trimethylsilyl)phenylacetylene polymer obtained in Example 1.
Claims (1)
ってもよく、低級アルキル基を表わし、ｎは繰返し単位
の繰返し数を表わす整数である。〕 で表わされるｏ−（トリアルキルシリル）フェニルアセ
チレン重合体。 ２）一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾１、Ｒ＾２およびＲ＾３は前記に定義のと
おりである〕 で表わされるｏ−（トリアルキルシリル）フェニルアセ
チレンを、第VI族遷移金属化合物の存在下で重合させる
ことからなる前記一般式（ I ）で表わされるｏ−（ト
リアルキルシリル）フェニルアセチレン重合体の製法。 ３）特許請求の範囲第２項記載の製法であって、前記の
重合を、さらに還元剤の存在下において行なう製法。[Claims] 1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1, R^2 and R^3 may be the same or different, It represents a lower alkyl group, and n is an integer representing the number of repeating units. ] An o-(trialkylsilyl)phenylacetylene polymer represented by: 2) o-(trialkylsilyl)phenylacetylene represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2 and R^3 are as defined above] A method for producing an o-(trialkylsilyl)phenylacetylene polymer represented by the general formula (I), which comprises polymerizing in the presence of a Group VI transition metal compound. 3) The manufacturing method according to claim 2, wherein the above polymerization is further carried out in the presence of a reducing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23842186A JPH0610216B2 (en) | 1986-10-07 | 1986-10-07 | 0- (trialkylsilyl) phenylacetylene polymer and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23842186A JPH0610216B2 (en) | 1986-10-07 | 1986-10-07 | 0- (trialkylsilyl) phenylacetylene polymer and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6392619A true JPS6392619A (en) | 1988-04-23 |
| JPH0610216B2 JPH0610216B2 (en) | 1994-02-09 |
Family
ID=17029957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23842186A Expired - Fee Related JPH0610216B2 (en) | 1986-10-07 | 1986-10-07 | 0- (trialkylsilyl) phenylacetylene polymer and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0610216B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02102289A (en) * | 1988-10-11 | 1990-04-13 | Sekisui Chem Co Ltd | Electrochromic element |
| JPH02296890A (en) * | 1989-05-10 | 1990-12-07 | Sekisui Chem Co Ltd | Eletrochromic element |
| US7977441B2 (en) | 2005-11-25 | 2011-07-12 | National Institute Of Advanced Industrial Science And Technology | Acetylene-based polymer |
| CN102604104A (en) * | 2012-02-29 | 2012-07-25 | 山东大学 | Preparation method of high-temperature-resistant silicon resin containing phenylethynyl group |
-
1986
- 1986-10-07 JP JP23842186A patent/JPH0610216B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02102289A (en) * | 1988-10-11 | 1990-04-13 | Sekisui Chem Co Ltd | Electrochromic element |
| JPH02296890A (en) * | 1989-05-10 | 1990-12-07 | Sekisui Chem Co Ltd | Eletrochromic element |
| US7977441B2 (en) | 2005-11-25 | 2011-07-12 | National Institute Of Advanced Industrial Science And Technology | Acetylene-based polymer |
| CN102604104A (en) * | 2012-02-29 | 2012-07-25 | 山东大学 | Preparation method of high-temperature-resistant silicon resin containing phenylethynyl group |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0610216B2 (en) | 1994-02-09 |
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