JPH04366128A - Production of polycarbonate - Google Patents
Production of polycarbonateInfo
- Publication number
- JPH04366128A JPH04366128A JP23860491A JP23860491A JPH04366128A JP H04366128 A JPH04366128 A JP H04366128A JP 23860491 A JP23860491 A JP 23860491A JP 23860491 A JP23860491 A JP 23860491A JP H04366128 A JPH04366128 A JP H04366128A
- Authority
- JP
- Japan
- Prior art keywords
- polycarbonate
- terminal hydroxyl
- hydroxyl groups
- carbonate
- mol
- 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
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 35
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 5
- 125000005011 alkyl ether group Chemical group 0.000 claims 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract description 4
- 150000005690 diesters Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 4
- -1 chlorine ions Chemical class 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000001816 cooling Methods 0.000 description 3
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OIZBWJKWAYXWLY-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)-2h-fluoren-1-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=C1C(=O)CC=C2 OIZBWJKWAYXWLY-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- JMPVESVJOFYWTB-UHFFFAOYSA-N dipropan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)C JMPVESVJOFYWTB-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、色調の改良されたポリ
カーボネートの製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing polycarbonate with improved color tone.
【０００２】0002
【従来技術】ポリカーボネートは、耐衝撃性などの機械
的特性に優れ、しかも耐熱性、透明性などにも優れてお
り、広く用いられている。このようなポリカーボネート
の製造方法としては、芳香族ジヒドロキシ化合物とホス
ゲンとを反応させる方法（界面法）、あるいはビスフェ
ノールなどの芳香族ジヒドロキシ化合物と炭酸ジエステ
ルとを溶融状態で重縮合する方法（エステル交換法）な
どが知られている。BACKGROUND OF THE INVENTION Polycarbonate is widely used because it has excellent mechanical properties such as impact resistance, as well as heat resistance and transparency. Methods for producing such polycarbonates include a method in which an aromatic dihydroxy compound and phosgene are reacted (interfacial method), or a method in which an aromatic dihydroxy compound such as bisphenol and a carbonic acid diester are polycondensed in a molten state (ester exchange method). ) etc. are known.
【０００３】界面重縮合法は、一般的にポリカーボネー
トの製造に効果的であるが、有毒なホスゲンを使用する
ことや塩素イオンが生成するポリカーボネートに残存す
ることなどの欠点を有する。Although the interfacial polycondensation method is generally effective for producing polycarbonate, it has drawbacks such as the use of toxic phosgene and the fact that chlorine ions remain in the polycarbonate produced.
【０００４】これらの欠点を除くために、有毒なホスゲ
ンの代わりにホスゲンのダイマーである液体のトリクロ
ロメチルクロロホルメートと特殊な２価フェノールとを
界面重縮合反応でポリカーボネートを製造する方法が特
開昭６３−１８２３３６号に開示されている。[0004] In order to eliminate these drawbacks, a method for producing polycarbonate by interfacial polycondensation reaction of liquid trichloromethyl chloroformate, which is a dimer of phosgene, and a special dihydric phenol, instead of toxic phosgene, has been disclosed. It is disclosed in Sho 63-182336.
【０００５】[0005]
【発明が解決しようとする課題】しかしながら、特殊な
２価フェノールとして９，９−ビス（４−ヒドロキシフ
ェニル）フルオレノン類についての記載があるのみであ
る。また、有毒なホスゲンの代わりにトリホスゲンを用
いて２，２−ビス（４−ヒドロキシフェニル）プロパン
からポリカーボネートを得る方法がＡｎｇｅｗ．Ｃｈｅ
ｍ．（アンゲバンテ，ヘミー）９９．９２２（１９８７
）に記載されているが、ホスゲンが発生する反応機構も
提唱されている。However, there is only a description of 9,9-bis(4-hydroxyphenyl)fluorenone as a special dihydric phenol. Also, Angew describes a method for obtaining polycarbonate from 2,2-bis(4-hydroxyphenyl)propane using triphosgene instead of toxic phosgene. Che
m. (Angevante, Hemy) 99.922 (1987
), but a reaction mechanism in which phosgene is generated has also been proposed.
【０００６】一方、芳香族系有機二水酸基化合物と炭酸
ジエステルとのエステル交換反応によってポリカーボネ
ートを製造する際には、芳香族ジヒドロキシ化合物と炭
酸ジエステルとを、金属の有機酸塩、無機酸塩、酸化物
、水酸化物、水素化物あるいはアルコラート、電子供与
性アミン化合物（特開平３−２７６２２）、第４級アン
モニウム塩（特開平２−１７５７２３）又は、アルカリ
金属、アルカリ土類金属の併用（特開平２−１７５７２
３）などの触媒を用いて、通常２５０〜３３０℃の温度
で減圧下に加熱しながら溶融状態でエステル交換反応さ
せているため、前述の界面法と比較して安価にポリカー
ボネートを製造することができるという利点を有してい
る。On the other hand, when producing polycarbonate by the transesterification reaction between an aromatic organic dihydroxy compound and a carbonic acid diester, the aromatic dihydroxy compound and the carbonic acid diester are mixed with an organic acid salt, an inorganic acid salt, or an oxidized metal salt. compounds, hydroxides, hydrides or alcoholates, electron-donating amine compounds (JP-A-3-27622), quaternary ammonium salts (JP-A-2-175723), or combinations of alkali metals and alkaline earth metals (JP-A-Hei 2-175723). 2-17572
Since the transesterification reaction is carried out in the molten state while heating under reduced pressure at a temperature of usually 250 to 330°C using a catalyst such as 3), polycarbonate can be produced at a lower cost compared to the interfacial method described above It has the advantage of being possible.
【０００７】上記のように、重合されたポリカーボネー
ト樹脂を混練押出処理することにより最終生成物を得て
いるが、最終生成物中に不純物、特に末端水酸基濃度の
高いオリゴマー、ポリマー等が残留するという問題があ
る。かかる化合物はポリカーボネート樹脂の成形時に黄
変を起こす原因となるなどの不都合を生じるため、その
除去方法が種々検討されている。As mentioned above, the final product is obtained by kneading and extruding polymerized polycarbonate resin, but it is said that impurities, especially oligomers and polymers with a high concentration of terminal hydroxyl groups, remain in the final product. There's a problem. Since such compounds cause inconveniences such as causing yellowing during molding of polycarbonate resins, various methods for their removal have been studied.
【０００８】例えば、米国特許明細書第３，２６７，０
７５号には、ポリカーボネート溶液に不活性物質を注入
して押出す方法が開示されているが、注入した不活性物
質が残留するとポリカーボネート樹脂の耐熱性が低下し
、また食品衛生上の問題が生じるなどの欠点がある。For example, US Pat. No. 3,267,0
No. 75 discloses a method of injecting an inert substance into a polycarbonate solution and extruding it, but if the injected inert substance remains, the heat resistance of the polycarbonate resin will decrease and food hygiene problems will occur. There are drawbacks such as.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、ポリカー
ボネートを炭酸ジエステルで処理することにより、末端
水酸基濃度を０．１モル％以下であるポリカーボネート
の製造方法を見出すに至った。上記のように製造された
ポリカーボネートは末端水酸基濃度が極めて低いため、
着色することなく、色調、耐熱性、耐加水分解性に優れ
たポリカーボネートを得ることができる。[Means for Solving the Problems] The present inventors have discovered a method for producing polycarbonate having a terminal hydroxyl group concentration of 0.1 mol % or less by treating polycarbonate with a carbonic acid diester. Since the polycarbonate produced as described above has an extremely low concentration of terminal hydroxyl groups,
Polycarbonate with excellent color tone, heat resistance, and hydrolysis resistance can be obtained without coloring.
【００１０】0010
【発明の具体的説明】本発明において、ポリカーボネー
トの形状は粉末でもペレットでもどちらでも用いること
ができる。ポリカーボネートに炭酸ジアルキルエステル
を加え、炭酸ジアルキルエステルの沸点以下で加熱する
ことにより、末端水酸基をアルキルエーテル化する。DETAILED DESCRIPTION OF THE INVENTION In the present invention, polycarbonate can be used in either powder or pellet form. By adding carbonate dialkyl ester to polycarbonate and heating at a temperature below the boiling point of carbonate dialkyl ester, terminal hydroxyl groups are converted into alkyl ether.
【００１１】ここで用いられる炭酸ジアルキルエステル
の代表例は、ジメチルカーボネート、ジエチルカーボネ
ート、ジプロピルカーボネート、ジイソプロピルカーボ
ネート、ジブチルカーボネート、ジターシャリーブチル
カーボネート等を挙げることができる。また、これらの
中から選ばれる２種又は３種の混合炭酸ジアルキルエス
テルを用いることも可能である。Typical examples of the carbonic acid dialkyl ester used here include dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, ditertiary butyl carbonate, and the like. It is also possible to use two or three mixed dialkyl carbonate esters selected from these.
【００１２】次に本発明を実施例により説明するが、本
発明は、これらの実施例によって限定するものではない
。[0012] Next, the present invention will be explained by examples, but the present invention is not limited to these examples.
【００１３】[0013]
【実施例１】２，２−ビス（４−ヒドロキシフェニル）
プロパン２２．８ｇ（０．１モル）と２−メチルイミダ
ゾール０．１６４ｇ（２×１０−２モル）、ビスフェニ
ルカーボネート２１．４ｇ（０．１モル）を加え窒素下
、１８０゜Ｃで１時間撹拌後、徐々に減圧しながら昇温
させ、最終的に０．１Ｔｏｒｒ、２７０゜Ｃ、１時間重
縮合反応させ生成するフェノールを留去させて、無色透
明なポリカーボネートを
１５０゜Ｃであった。粘度平均分子量の測定方法は、２
０゜Ｃにおける塩化メチレン溶液の固
算した。[Example 1] 2,2-bis(4-hydroxyphenyl)
Add 22.8 g (0.1 mol) of propane, 0.164 g (2 x 10-2 mol) of 2-methylimidazole, and 21.4 g (0.1 mol) of bisphenyl carbonate and heat at 180°C for 1 hour under nitrogen. After stirring, the temperature was gradually increased while reducing the pressure, and finally the polycondensation reaction was carried out at 0.1 Torr and 270°C for 1 hour, and the produced phenol was distilled off, leaving a colorless and transparent polycarbonate at 150°C. The method for measuring viscosity average molecular weight is 2.
The methylene chloride solution at 0°C was calculated.
【００１４】[0014]
【数１】[Math 1]
【００１５】末端水酸基の濃度は、８モル％であった。
末端水酸基濃度の測定方法は末端基構造：サンプル０．
４ｇを３ｍｌのクロロホルムに溶解し、４０゜Ｃで１３
Ｃ−ＮＭＲ（日本電子社製、ＧＸ−２７０）を用いて、
末端のＯＨ基及び構造を測定した。末端ＯＨ基濃度は、
全末端基濃度に対する割合（％）で計算した。The concentration of terminal hydroxyl groups was 8 mol %. The method for measuring the terminal hydroxyl group concentration is based on the terminal group structure: Sample 0.
Dissolve 4g in 3ml of chloroform and heat at 40°C for 13
Using C-NMR (manufactured by JEOL Ltd., GX-270),
The terminal OH group and structure were measured. The terminal OH group concentration is
Calculated as a percentage (%) of the total end group concentration.
【００１６】このように合成されたポリカーボネート５
０ｇをジメチルカーボネート２００ｍｌに加え、２時間
加熱還流した。冷却した後、ジメチルカーボネートとポ
リカーボネート分別し、１００゜Ｃ、０．１Ｔｏｒｒで
真空乾燥した。このポリカーボネートの末端水酸基の濃
度は０．０１モル％であった。Polycarbonate 5 synthesized in this way
0 g was added to 200 ml of dimethyl carbonate, and the mixture was heated under reflux for 2 hours. After cooling, dimethyl carbonate and polycarbonate were separated and vacuum dried at 100°C and 0.1 Torr. The concentration of terminal hydroxyl groups in this polycarbonate was 0.01 mol%.
【００１７】[0017]
【実施例２】実施例１と同様に合成されたポリカーボネ
ート５０ｇをジエチルカーボネート２００ｍｌに加え、
２時間加熱還流した。冷却した後、ジエチルカーボネー
トとポリカーボネトを分別し、１００゜Ｃ、０．１Ｔｏ
ｒｒで真空乾燥した。このポリカーボネートの末端水酸
基の濃度は０．０２モル％であった。[Example 2] 50 g of polycarbonate synthesized in the same manner as in Example 1 was added to 200 ml of diethyl carbonate,
The mixture was heated under reflux for 2 hours. After cooling, diethyl carbonate and polycarbonate were separated and heated at 100°C and 0.1To
It was vacuum dried at rr. The concentration of terminal hydroxyl groups in this polycarbonate was 0.02 mol%.
【００１８】[0018]
【実施例３】実施例１と同様に含成されたポリカーボネ
一ト５０ｇをジブチルカーボネート２００ｍｌに加え、
２時間加熱還流した。冷却した後、ジブチルカーボネー
トとポリカーボネートを分別し、１００゜Ｃ、０．１Ｔ
ｏｒｒで真空乾燥した。このポリカーボネートの末端水
酸基の濃度は０．０５モル％であった。[Example 3] 50 g of polycarbonate containing the same composition as in Example 1 was added to 200 ml of dibutyl carbonate,
The mixture was heated under reflux for 2 hours. After cooling, dibutyl carbonate and polycarbonate were separated and heated at 100°C and 0.1T.
It was vacuum dried in orr. The concentration of terminal hydroxyl groups in this polycarbonate was 0.05 mol%.
【００１９】[0019]
【比較例１】実施例１で合成されたポリカーボネートの
末端水酸基の濃度は８モル％であった。Comparative Example 1 The concentration of terminal hydroxyl groups in the polycarbonate synthesized in Example 1 was 8 mol%.
【００２０】[0020]
【表１】[Table 1]
【００２１】[0021]
【発明の効果】上記のような本発明の方法によれば、末
端水酸基濃度の極めて少ないポリカーボネートを容易に
得られることができる。しかも、得られたポリカーボネ
ートは優れた黄色指数を示し、また、熱安定性に優れて
いる。According to the method of the present invention as described above, polycarbonate having an extremely low concentration of terminal hydroxyl groups can be easily obtained. Moreover, the obtained polycarbonate exhibits an excellent yellow index and also has excellent thermal stability.
Claims (2)
することにより末端水酸基濃度を０．１モル％以下とす
ることを特徴とするポリカーボネートの製造方法。1. A method for producing polycarbonate, which comprises treating the polycarbonate with a carbonic acid diester to reduce the concentration of terminal hydroxyl groups to 0.1 mol % or less.
エーテル基からなるポリカーボネート。2. A polycarbonate comprising alkyl ether groups having a terminal concentration of 99.9 mol % or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23860491A JPH04366128A (en) | 1991-06-12 | 1991-06-12 | Production of polycarbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23860491A JPH04366128A (en) | 1991-06-12 | 1991-06-12 | Production of polycarbonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04366128A true JPH04366128A (en) | 1992-12-18 |
Family
ID=17032657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23860491A Pending JPH04366128A (en) | 1991-06-12 | 1991-06-12 | Production of polycarbonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04366128A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5905135A (en) * | 1997-12-08 | 1999-05-18 | General Electric Company | Method of preparing polycarbonates by solid state polymerization |
| WO2012157766A1 (en) | 2011-05-19 | 2012-11-22 | 三菱瓦斯化学株式会社 | Polycarbonate copolymer having high fluidity, method for producing aromatic polycarbonate resin having high molecular weight, and aromatic polycarbonate compound |
-
1991
- 1991-06-12 JP JP23860491A patent/JPH04366128A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5905135A (en) * | 1997-12-08 | 1999-05-18 | General Electric Company | Method of preparing polycarbonates by solid state polymerization |
| EP0949288A1 (en) * | 1997-12-08 | 1999-10-13 | General Electric Company | Method of preparing polycarbonates by solide state polymerization |
| WO2012157766A1 (en) | 2011-05-19 | 2012-11-22 | 三菱瓦斯化学株式会社 | Polycarbonate copolymer having high fluidity, method for producing aromatic polycarbonate resin having high molecular weight, and aromatic polycarbonate compound |
| KR20140035412A (en) | 2011-05-19 | 2014-03-21 | 미츠비시 가스 가가쿠 가부시키가이샤 | Polycarbonate copolymer having high fluidity, method for producing aromatic polycarbonate resin having high molecular weight, and aromatic polycarbonate compound |
| US9353216B2 (en) | 2011-05-19 | 2016-05-31 | Mitsubishi Gas Chemical Company, Inc. | High-fluidity polycarbonate copolymer, process for production highly polymerized aromatic polycarbonate resin and aromatic polycarbonate compound |
| US10053537B2 (en) | 2011-05-19 | 2018-08-21 | Mitsubishi Gas Chemical Company, Inc. | High-fluidity polycarbonate copolymer, process for production highly polymerized aromatic polycarbonate resin and aromatic polycarbonate compound |
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