JPH01315421A - Aromatic polysulfone - Google Patents
Aromatic polysulfoneInfo
- Publication number
- JPH01315421A JPH01315421A JP14754288A JP14754288A JPH01315421A JP H01315421 A JPH01315421 A JP H01315421A JP 14754288 A JP14754288 A JP 14754288A JP 14754288 A JP14754288 A JP 14754288A JP H01315421 A JPH01315421 A JP H01315421A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- temperature
- thermogravimetric analysis
- aromatic polysulfone
- heat
- 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.)
- Pending
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 16
- 229920002492 poly(sulfone) Polymers 0.000 title claims abstract description 16
- 238000002411 thermogravimetry Methods 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 4
- 230000004580 weight loss Effects 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 abstract description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000002798 polar solvent Substances 0.000 abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 238000006068 polycondensation reaction Methods 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 238000010411 cooking Methods 0.000 abstract description 2
- 238000010292 electrical insulation Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000000465 moulding Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- OFCFYWOKHPOXKF-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-chlorobenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 OFCFYWOKHPOXKF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 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】
本発明は、熱費°定性の優れた成形温度範囲の広い芳香
族ポリスルホンに関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an aromatic polysulfone with excellent heat cost properties and a wide molding temperature range.
（産業上の利用分野）
芳香族ポリスルホンは、耐熱性２機械性能及び耐薬品性
に優れており、商業的りこ実用性の高いものである。(Industrial Application Field) Aromatic polysulfone has excellent heat resistance, mechanical performance, and chemical resistance, and is highly practical for commercial use.
（従来の技術とその課題）
芳香族ポリスルホンは、高軟化点を有する熱可塑性樹脂
である。この高軟化点ゆえに、即ち高温における溶融粘
度が高いゆえに、射出成形等の成形加工時に３５０’Ｃ
前後の高温が必要となる。(Prior art and its problems) Aromatic polysulfone is a thermoplastic resin with a high softening point. Because of this high softening point, that is, because of the high melt viscosity at high temperatures, it is possible to
High temperatures before and after are required.
従って、熱分解温度が低いポリマーは、成形中に分解、
ゲル化等により溶融粘度が増加したり、著しく着色する
といった問題点を生ずる。Therefore, polymers with low thermal decomposition temperatures decompose during molding.
Problems arise such as increased melt viscosity and significant coloring due to gelation and the like.
実際、特公昭４２−７７９９号、特公昭４５−２１３１
８号。In fact, Special Publication No. 42-7799, Special Publication No. 45-2131
No. 8.
特公昭４６−２１４５８号及び特公昭５５−２３５７４
号等に開示されている方法で製造した芳香族ポリスルホ
ンは、成形中に溶融粘度が増加したり、色が淡黄色から
褐色に変化したりして、上記問題点を解決するのに満足
なものではない。Special Publication No. 46-21458 and Special Publication No. 55-23574
The aromatic polysulfone produced by the method disclosed in the above issue is satisfactory in solving the above problems, such as the melt viscosity increasing during molding and the color changing from pale yellow to brown. isn't it.
（課題を解決するための手段）
本発明者らは、かかる問題点を解決すべく鋭意検討した
結果、驚くべきことに、熱重量分析（昇温速度２０℃／
分）における２、５％重量減少時温度が５０５℃以上の
芳香族ポリスルホンを用いると、成形中に溶融粘度が増
加したり、色が淡黄色から褐色に変化したりすることの
ない成形体が得られることを見出し、本発明を完成する
に至った。(Means for Solving the Problems) As a result of intensive studies aimed at solving these problems, the present inventors surprisingly found that thermogravimetric analysis (heating rate of 20°C/
When using aromatic polysulfone with a temperature of 505°C or higher at the time of 2.5% weight loss during molding, a molded product that does not increase in melt viscosity or change in color from pale yellow to brown during molding can be obtained. The present inventors have discovered that the present invention can be obtained, and have completed the present invention.
即ち本発明は、成形時に溶融粘度が増加したり、著しく
着色するといった問題点を生じない、熱重量分析（昇温
速度２０℃Ｉ分）における２、５％重量減少時の温度が
５０５℃以上である、一般式（Ｉ）で示される繰り返し
単位を有する芳香族ポリスルホンに関するものである。That is, the present invention does not cause problems such as an increase in melt viscosity or significant discoloration during molding, and the temperature at the time of 2.5% weight loss in thermogravimetric analysis (temperature increase rate 20 °C I min) is 505 °C or higher. This invention relates to an aromatic polysulfone having a repeating unit represented by the general formula (I).
本発明でいう熱重量分析（昇温速度２０℃／分）におけ
る２、５％重量減少時の温度が５０５℃以上である芳香
族ポリスルホンは、下記に述べる方法で得ることが出来
るが、本発明はこれに限定されるものではなく、熱重量
分析（昇温速度２０℃／分）における２、５％重量減少
時の温度が５０５℃以上である芳香族ポリスルホンであ
れば、いかなる方法で製造してもかまわない。The aromatic polysulfone which has a temperature of 505°C or higher at the time of 2.5% weight loss in thermogravimetric analysis (heating rate 20°C/min) as used in the present invention can be obtained by the method described below. is not limited to this, but aromatic polysulfone can be produced by any method as long as it has a temperature of 505°C or higher at 2.5% weight loss in thermogravimetric analysis (heating rate 20°C/min). It doesn't matter.
く熱重量分析（昇温速度２０℃／分）における２、５％
重量減少時の温度が５０５℃以上である芳香族ポリスル
ホンの製造方法〉
一般に芳香族ポリスルホンは、以下の方法にて合成する
ことが出来る。例えば、極性溶媒中で二価フェノールと
アルカリ金属の水酸化物の水溶液より二価フェノールの
アルカリ金属二塩を合成し、系中の水分を除去した後、
ジハロゲノベンゼノイド化合物を添加して重縮合反応さ
せる方法、又は二価フェノールとジハロゲノベンゼノイ
ド化合物及びアルカリ金属水酸化物の水溶液とを、極性
溶媒中で系中の水分を除去させなから重縮合反応させる
方法、もしくは二価フェノールとジハロゲノベンゼノイ
ド化合物とを極性溶媒中アルカリ金属炭酸塩の存在下に
て重縮合反応させる方法等がある。2.5% in thermogravimetric analysis (heating rate 20°C/min)
Method for producing aromatic polysulfone whose temperature at weight reduction is 505° C. or higher> Generally, aromatic polysulfone can be synthesized by the following method. For example, an alkali metal di-salt of dihydric phenol is synthesized from an aqueous solution of dihydric phenol and alkali metal hydroxide in a polar solvent, and after removing water in the system,
A method in which a dihalogenobenzenoid compound is added and a polycondensation reaction is carried out, or a dihydric phenol and an aqueous solution of a dihalogenobenzenoid compound and an alkali metal hydroxide are combined in a polar solvent without removing water from the system. There is a method of carrying out a condensation reaction, or a method of carrying out a polycondensation reaction of a dihydric phenol and a dihalogenobenzenoid compound in the presence of an alkali metal carbonate in a polar solvent.
本発明で言う熱重量分析（昇温速度２０６Ｃ／分）にお
ける２、５％重量減少時の温度が５０５℃以上である芳
香族ポリスルホンは、上記反応において末端を熱的に安
定な構造にすることにより得られる。そのような方法と
しては、例えば末端封止剤である一価のフェノール、も
しくはモノハロゲノベンゼノイド化合物を反応のはじめ
から、もしくは後添加にて反応させ末端封止する方法、
或いは上記反応方法において、はじめから二価フェノー
ルに対してジハロゲノベンゼノイド化合物を過剰に用い
て反応させる方法等により合成することが出来る。In the present invention, the aromatic polysulfone whose temperature at the time of 2.5% weight loss in thermogravimetric analysis (temperature increase rate 206 C/min) is 505 °C or higher has a terminal structure that is thermally stable in the above reaction. It is obtained by Such a method includes, for example, a method of terminal-capping by reacting a monovalent phenol or a monohalogenobenzenoid compound as an end-capping agent from the beginning of the reaction or by adding it afterward;
Alternatively, in the above reaction method, it can be synthesized by using an excess amount of the dihalogenobenzenoid compound with respect to the dihydric phenol from the beginning.
本発明によって得られる芳香族ポリスルホンは、その優
れた耐熱性２機械性能及び耐薬品性により、電気絶縁用
途、耐熱部品、調理用具、コーティング材料、精密部品
等に用いることが出来る。The aromatic polysulfone obtained by the present invention can be used for electrical insulation purposes, heat-resistant parts, cooking utensils, coating materials, precision parts, etc. due to its excellent heat resistance, mechanical performance, and chemical resistance.
（実施例）
本発明を以下の実施例及び比較例にて詳細に説明するが
、これをもって本発明を制限するものではない。(Example) The present invention will be explained in detail using the following Examples and Comparative Examples, but the present invention is not limited thereto.
実施例１
撹拌機、窒素導入管、温度計及び先端に受器を付した凝
縮器とを備えた４０モ反応缶内に、２，２−ビス（４−
ヒドロキシフェニル）プロパン１８２６ｇ （８，００
０モル）、４．４−ジクロロジフェニルスルホン（８。Example 1 2,2-bis(4-
Hydroxyphenyl)propane 1826g (8,00
0 mol), 4,4-dichlorodiphenylsulfone (8.
１６０モル）、無水炭酸カリウム２２１１ｇ （１６．
０００モル）及びＮ，Ｎ−ジメチルアセトアミド１２
ｋｇを仕込み、１時間窒素ガスを導入し、系内を窒素に
置換した。温度を反応液の沸点まで上昇させ、２時間か
けて約２ｋｇのＮ，Ｎ−ジメチルアセトアミドを留出さ
せた。同時に約１４４ｇのＨ２Ｏが留出された。その後
、還流状態で更に４時間反応させた後、温度を室温まで
戻し、析出した塩及び過剰の炭酸カリウムをン戸別し、
ｆ液を大量のメタノール中に注いで生成ポリマーを沈殿
させた。生成ポリマーを単離し、数回メタノール及び水
で洗浄した後、１５０℃で３時間減圧乾燥させた。160 mol), anhydrous potassium carbonate 2211 g (16.
000 mol) and N,N-dimethylacetamide 12
kg was charged, nitrogen gas was introduced for 1 hour, and the inside of the system was replaced with nitrogen. The temperature was raised to the boiling point of the reaction solution, and about 2 kg of N,N-dimethylacetamide was distilled out over 2 hours. At the same time, about 144 g of H2O was distilled off. After that, the reaction was continued for another 4 hours under reflux, the temperature was returned to room temperature, and the precipitated salt and excess potassium carbonate were separated.
Liquid f was poured into a large amount of methanol to precipitate the produced polymer. The produced polymer was isolated, washed several times with methanol and water, and then dried under reduced pressure at 150° C. for 3 hours.
得られたポリマーの収率は９８％で、１％ｗｔ ／ ｖ
ｏｌのＮ，Ｎ−ジメチルホルムアミド溶液中、２５℃で
の還元粘度ｒｌｒｅｄは０．４８ ｄ ｅ ／ ｇで、
２７０メガヘルツ（ＭＨｚ）、 ＩＨ−ＮＭＲ測定によ
りポリマーの末端基は９５％以上が
であることがわかった。The yield of the obtained polymer was 98% with 1% wt/v
The reduced viscosity rlred of ol in N,N-dimethylformamide solution at 25 °C is 0.48 d e / g,
IH-NMR measurement at 270 megahertz (MHz) revealed that more than 95% of the polymer had terminal groups.
このポリマーについて昇温速度２０℃／分で熱重量分析
を行ったところ、２８５％重量減少時の温度は５１３℃
であった。When thermogravimetric analysis was performed on this polymer at a heating rate of 20°C/min, the temperature at 285% weight loss was 513°C.
Met.
次に、得られたポリマーを３４０℃で射出成形したが、
何ら異常は認められなかった。Next, the obtained polymer was injection molded at 340°C.
No abnormality was observed.
実施例２
撹拌機、窒素導入管、温度計及び先端に受器を付した凝
縮器とを備えた４０老反応缶内に、２，２．ビス（４−
ヒドロキシフェニル）プロパン１８２６ｇ （８，００
０モル）、４，４′−ジクロロジフェニルスルホン２２
５１ｇ（７，８４０モル）、（４−クロロフェニル）ス
ルホニルベンゼン８０．４ｇ （０，３２０モル）、無
水炭酸カリウム２２１１ｇ （１６，０００モル）及び
Ｎ、Ｎ−ジメチルアセトアミド１２ｋｇを仕込み、１時
間窒素ガスを導入し、系内を窒素に置換した。温度を反
応液の沸点まで上昇させ、２時間かけて約２ｋｇのＮ、
Ｎ−ジメチルアセトアミドを留出させた。同時に約１４
４ｇのＨ２Ｏが留出された。その後、還流状態で更に４
時間反応させた後、温度を室温まで戻し、析出した塩及
び過剰の炭酸カリウムな一別し、ｒ液を大量のメタノー
ル中に注いで生成ポリマーを沈殿させた。生成ポリマー
を単離し、数回メタノール及び水で洗浄した後、１５０
℃で３時間減圧乾燥させた。Example 2 2, 2. Bis(4-
Hydroxyphenyl)propane 1826g (8,00
0 mol), 4,4'-dichlorodiphenylsulfone 22
51 g (7,840 mol), (4-chlorophenyl)sulfonylbenzene 80.4 g (0,320 mol), anhydrous potassium carbonate 2211 g (16,000 mol), and 12 kg of N,N-dimethylacetamide were charged and heated with nitrogen gas for 1 hour. was introduced to replace the atmosphere in the system with nitrogen. The temperature was raised to the boiling point of the reaction solution, and about 2 kg of N was added over 2 hours.
N-dimethylacetamide was distilled off. About 14 at the same time
4g of H2O was distilled off. Then, under reflux, 4 more
After reacting for an hour, the temperature was returned to room temperature, the precipitated salt and excess potassium carbonate were separated, and the r solution was poured into a large amount of methanol to precipitate the produced polymer. After isolation of the produced polymer and washing with methanol and water several times, 150
It was dried under reduced pressure at ℃ for 3 hours.
得られたポリマーの収率は９６％で、１％ｗｔ ／ ｖ
ｏｌのＮ、Ｎ−ジメチルホルムアミド溶液中、２５℃で
の還元粘度１１ｒｅｄは０．５５ ｄ ｔ ／ｇで、２
７０メガヘルツ（ＭＨｚ）、 ＩＨ−ＮＭＲ測定により
ポリマーの末端基は９５％以上が
であることがわかった。The yield of the obtained polymer was 96% with 1% wt/v
The reduced viscosity 11red of ol in N,N-dimethylformamide solution at 25°C is 0.55 dt/g, 2
IH-NMR measurement at 70 megahertz (MHz) revealed that more than 95% of the polymer had terminal groups.
このポリマーについて、昇温速度２０℃／分で熱重量分
析を行ったところ、２，５％重量減少時の温度は５１２
℃であった。When thermogravimetric analysis was performed on this polymer at a heating rate of 20°C/min, the temperature at 2.5% weight loss was 512°C.
It was ℃.
次に得られたポリマーを３４０℃で射出成形したが、何
ら異常は認められなかった。Next, the obtained polymer was injection molded at 340°C, but no abnormality was observed.
実施例３
撹拌機、窒素導入管、温度計及び先端に受器を付した凝
縮器とを備えた４０テ反応缶内に、２，２−ビス（４−
ヒドロキシフェニル）プロパン１８２６ｇ （８，００
０モル）、４．４−ジクロロジフェニルスルホン（８．
１６０モル）、フェノール３０ｇ （０．３２０モル）
、無水炭酸カリウム２２１１ ｇ （１６．０００モル
）及びＮ，Ｎ−ジメチルアセトアミド１２ｋｇを仕込み
、１時間窒素ガスを導入し、系内を窒素に置換した。温
度を反応液の沸点まで上昇させ、２時間かけて約２ｋｇ
のＮ，Ｎ−ジメチルアセトアミドを留出させた。同時に
約１４４ｇのＨ２Ｏが留出された。その後、還流状態で
更に４時間反応させた後、温度を室温まで戻し、析出し
た塩及び過剰の炭酸カリウムを♂別し、Ｐ液を大量のメ
タノール中に注いで生成ポリマーを沈殿させた。生成ポ
リマーを単離し、数回メタノール及び水で洗浄した後、
１５０℃で３時間減圧乾燥させた。Example 3 2,2-bis(4-
Hydroxyphenyl)propane 1826g (8,00
0 mol), 4,4-dichlorodiphenylsulfone (8.
160 mol), phenol 30g (0.320 mol)
, 2211 g (16.000 mol) of anhydrous potassium carbonate and 12 kg of N,N-dimethylacetamide were charged, and nitrogen gas was introduced for 1 hour to replace the inside of the system with nitrogen. The temperature was raised to the boiling point of the reaction solution, and about 2 kg was poured over 2 hours.
of N,N-dimethylacetamide was distilled out. At the same time, about 144 g of H2O was distilled off. Thereafter, the reaction was continued under reflux for an additional 4 hours, and then the temperature was returned to room temperature, the precipitated salt and excess potassium carbonate were separated, and the P solution was poured into a large amount of methanol to precipitate the produced polymer. After isolating the produced polymer and washing it with methanol and water several times,
It was dried under reduced pressure at 150°C for 3 hours.
得られたポリマーの収率は９６％で、１％ｗｔ ／ ｖ
ｏｌのＮ，Ｎ−ジメチルホルムアミド溶液中、２５℃で
の還元粘度１１ｒｅｄは０．４７ ａ ！− ／ ｇで
、２７０メガヘルツ −（ＭＨｚ）、”Ｈ−ＮＭＲ測定
によりポリマーの末端基は９５％以上が
であることがわかった。The yield of the obtained polymer was 96% with 1% wt/v
The reduced viscosity 11red of ol in N,N-dimethylformamide solution at 25°C is 0.47 a! - / g, 270 MHz - (MHz), H-NMR measurement revealed that more than 95% of the terminal groups of the polymer were.
このポリマーについて、昇温速度２０℃Ｉ分で熱重量分
析を行ったところ、２．５％重量減少時の温度は５１５
℃であった。When thermogravimetric analysis was performed on this polymer at a heating rate of 20°C/min, the temperature at 2.5% weight loss was 515.
It was ℃.
次に得られたポリマーを３４０℃で射出成形したが、何
ら異常は認められなかった。Next, the obtained polymer was injection molded at 340°C, but no abnormality was observed.
比較例１
撹拌機，窒素導入管，温度計及び先端に受器を付した凝
縮器とを備えた４０ｅ反応缶内に、２，２−ビス（４−
ヒドロキシフェニル）プロパン１８２６ｇ （８．００
０モル）、４，４′−ジクロロジフェニルスルホン２２
５１ｇ（７．８４０モル）、無水炭酸カリウム２２１１
ｇ （１６．０００モル）及びＮ，Ｎ−ジメチルアセト
アミド１２ｋｇを仕込み、１時間窒素ガスを導入し、系
内を窒素に置換した。温度を反応液の沸点まで上昇させ
、２時間かけて約２ｋｇのＮ，Ｎ−ジメチルアセトアミ
ドを留出させた。同時に約１４４ｇのＨ２Ｏが留出され
た。その後、還流状態で更に４時間反応させた後、１０
０℃まで降温し、塩化メチルガスを１２で１分の流量で
３０分間吹き込んだ。その後、室温まで降温し、析出し
た塩及び過剰の炭酸カリウムをＰ別し、♂液を大量のメ
タノール中に注いで生成ポリマーを沈殿させた。生成ポ
リマーを単離し、数回メタノール及び水で洗浄した後、
１５０℃で３時間減圧乾燥させた。Comparative Example 1 2,2-bis(4-
Hydroxyphenyl)propane 1826g (8.00
0 mol), 4,4'-dichlorodiphenylsulfone 22
51 g (7.840 mol), anhydrous potassium carbonate 2211
g (16.000 mol) and 12 kg of N,N-dimethylacetamide were charged, and nitrogen gas was introduced for 1 hour to replace the inside of the system with nitrogen. The temperature was raised to the boiling point of the reaction solution, and about 2 kg of N,N-dimethylacetamide was distilled out over 2 hours. At the same time, about 144 g of H2O was distilled off. After that, after reacting for another 4 hours under reflux, 10
The temperature was lowered to 0° C., and methyl chloride gas was blown into the reactor at a flow rate of 12° C. for 30 minutes. Thereafter, the temperature was lowered to room temperature, the precipitated salt and excess potassium carbonate were separated with P, and the male solution was poured into a large amount of methanol to precipitate the produced polymer. After isolating the produced polymer and washing it with methanol and water several times,
It was dried under reduced pressure at 150°C for 3 hours.
得られたポリマーの収率は９５％で、１％ｗｔ ／ ｖ
ｏｌのＮ、Ｎ−ジメチルホルムアミド溶液中、２５℃で
の還元粘度ｒｌｒｅｄは０．４６ ｄ ｅ ７ｇで、２
７０メガヘルツ（ＭＨｚ）、 ＩＨ−ＮＭＲ測定により
ポリマーの末端基は９５％以上がＣＨ３０−であること
がわかった。The yield of the obtained polymer was 95% with 1% wt/v
The reduced viscosity rlred of ol in N,N-dimethylformamide solution at 25°C is 0.46 d e 7 g, 2
IH-NMR measurement at 70 megahertz (MHz) revealed that more than 95% of the terminal groups of the polymer were CH30-.
このポリマーについて、昇温速度２０℃Ｉ分で熱重量分
析を行ったところ、２．５％重量減少時の温度は４９９
℃であった。When thermogravimetric analysis was performed on this polymer at a heating rate of 20°C/min, the temperature at a weight loss of 2.5% was 499.
It was ℃.
次に得られたポリマーを３４０℃で射出成形したところ
、成形品に着色が見られた。Next, when the obtained polymer was injection molded at 340°C, coloring was observed in the molded product.
（発明の効果）
本発明の芳香族ポリスルホンは、熱分解温度が５０５℃
以上と高く、且つ溶融流動性に優れており、着色も少な
いものである。(Effect of the invention) The aromatic polysulfone of the present invention has a thermal decomposition temperature of 505°C.
In addition, it has excellent melt fluidity and little coloring.
Claims (1)
量減少時の温度が５０５℃以上である、一般式（ I ）
で示される繰り返し単位を有する芳香族ポリスルホン。 ▲数式、化学式、表等があります▼……（ I ）[Scope of Claims] General formula (I) whose temperature at 2.5% weight loss in thermogravimetric analysis (heating rate 20°C/min) is 505°C or higher
An aromatic polysulfone having a repeating unit represented by ▲There are mathematical formulas, chemical formulas, tables, etc.▼……(I)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14754288A JPH01315421A (en) | 1988-06-15 | 1988-06-15 | Aromatic polysulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14754288A JPH01315421A (en) | 1988-06-15 | 1988-06-15 | Aromatic polysulfone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01315421A true JPH01315421A (en) | 1989-12-20 |
Family
ID=15432676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14754288A Pending JPH01315421A (en) | 1988-06-15 | 1988-06-15 | Aromatic polysulfone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01315421A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1057783C (en) * | 1997-05-20 | 2000-10-25 | 吉林大学 | Synthesis of narrow distribted, high thermostability poly-ether-sulfone (PES) |
| WO2012133641A1 (en) * | 2011-03-31 | 2012-10-04 | 住友化学株式会社 | Method for producing polysulfone having reduced amount of contained halogens |
| JP2016511770A (en) * | 2012-12-18 | 2016-04-21 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | Portable electronic devices made of low chlorine aromatic polysulfone |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312991A (en) * | 1976-07-19 | 1978-02-06 | Ici Ltd | Process for producing aromatic polyether sulfone or ketone |
| JPS5334900A (en) * | 1976-07-12 | 1978-03-31 | Ici Ltd | Process for preparing polyether sulfone and*or* ketone |
| JPH01315422A (en) * | 1988-06-14 | 1989-12-20 | Daicel Chem Ind Ltd | Aromatic polysulfone |
-
1988
- 1988-06-15 JP JP14754288A patent/JPH01315421A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5334900A (en) * | 1976-07-12 | 1978-03-31 | Ici Ltd | Process for preparing polyether sulfone and*or* ketone |
| JPS5312991A (en) * | 1976-07-19 | 1978-02-06 | Ici Ltd | Process for producing aromatic polyether sulfone or ketone |
| JPH01315422A (en) * | 1988-06-14 | 1989-12-20 | Daicel Chem Ind Ltd | Aromatic polysulfone |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1057783C (en) * | 1997-05-20 | 2000-10-25 | 吉林大学 | Synthesis of narrow distribted, high thermostability poly-ether-sulfone (PES) |
| WO2012133641A1 (en) * | 2011-03-31 | 2012-10-04 | 住友化学株式会社 | Method for producing polysulfone having reduced amount of contained halogens |
| JP2016511770A (en) * | 2012-12-18 | 2016-04-21 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | Portable electronic devices made of low chlorine aromatic polysulfone |
| CN111253747A (en) * | 2012-12-18 | 2020-06-09 | 索尔维特殊聚合物美国有限责任公司 | Mobile Electronic Devices Made of Low Chlorine Aromatic Polysulfone |
| CN111253747B (en) * | 2012-12-18 | 2022-12-06 | 索尔维特殊聚合物美国有限责任公司 | Mobile electronic device made of low-chlorine aromatic polysulphone |
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