JPS62292830A - Aromatic polyester for optical material - Google Patents
Aromatic polyester for optical materialInfo
- Publication number
- JPS62292830A JPS62292830A JP61137016A JP13701686A JPS62292830A JP S62292830 A JPS62292830 A JP S62292830A JP 61137016 A JP61137016 A JP 61137016A JP 13701686 A JP13701686 A JP 13701686A JP S62292830 A JPS62292830 A JP S62292830A
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- aromatic polyester
- tables
- formulas
- optical materials
- 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 23
- 229920000728 polyester Polymers 0.000 title claims abstract description 22
- 230000003287 optical effect Effects 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 title claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 7
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 6
- 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 claims abstract description 6
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims abstract description 4
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 claims abstract description 3
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000962 organic group Chemical group 0.000 claims abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract description 3
- 238000012695 Interfacial polymerization Methods 0.000 abstract description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QDTCBEZXBDUOCR-UHFFFAOYSA-N n,n-dibutylbutan-1-amine oxide Chemical compound CCCC[N+]([O-])(CCCC)CCCC QDTCBEZXBDUOCR-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
- B41M5/41—Base layers supports or substrates
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Polyesters Or Polycarbonates (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は光学材料用芳香族ポリエステルに関する。詳し
くは、立体規制された芳香環を側鎖に持つ、８１屈折率
の低い芳香族ポリエステルに関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an aromatic polyester for optical materials. Specifically, the present invention relates to an aromatic polyester having a low refractive index of 81 and having a sterically restricted aromatic ring in a side chain.
通常、光学材料用たとえば光デイスク用プラスチックと
してポリメチルメタクリレ−）（ＰＭＭＡ）、ボリカー
ボネー） （ＰＣ）およびエポキシ樹脂などが用いられ
ている。Generally, polymethyl methacrylate (PMMA), polycarbonate (PC), and epoxy resins are used as plastics for optical materials, such as optical disks.
ところがＰ Ｍ Ｍ Ａとエポキシ樹脂はその複屈折は
ほぼゼロであるが、ＰＭＭＡは吸水性が大きく耐熱性も
やや不溝であり、エポキシ樹脂は射出成形できないとい
う欠点がある。一方ＰＣは耐熱性、吸水性はほぼ滴定で
きるが、溶融粘度が制く射出成形時の配向による複屈折
が発現するという欠点を有している。この点を克服する
ため、ＰＣの分子量を下げたり、オリゴマーを混合する
などして溶融粘度を下げる方法がとられているが、この
ような方法では、耐熱性および機械的強度の低下をきた
す恐れがあり、しかも成形条件を微妙にコ整しなければ
ならない。However, although PMMA and epoxy resin have almost zero birefringence, PMMA has a large water absorption property and somewhat poor heat resistance, and epoxy resin has the disadvantage that it cannot be injection molded. On the other hand, PC has heat resistance and water absorption that can be almost titrated, but it has the disadvantage that birefringence occurs due to orientation during injection molding, which is controlled by melt viscosity. In order to overcome this problem, methods have been taken to lower the melt viscosity by lowering the molecular weight of PC or mixing oligomers, but such methods may cause a decrease in heat resistance and mechanical strength. Moreover, the molding conditions must be delicately adjusted.
光学材料用ポリマーとして、前記従来より公知のポリマ
ーを改良しても限界があるため、全く異なるポリマーを
考慮した場合、たとえば透明で耐熱性の良好なポリマー
としてビスフェ／ −／Ｉｚ Ａ ラグリコール成分と
する芳香族ポリエステルがあるが、複屈折率が非常に高
く、光学材料用、特に光デイスク用としては全く使用で
きない。As polymers for optical materials, there are limits even if the conventionally known polymers are improved, so when considering completely different polymers, for example, bisphe/-/IzA Laglycol component and a transparent and heat-resistant polymer. Although there are aromatic polyesters that have a very high birefringence, they cannot be used at all for optical materials, especially for optical disks.
Ｃ問題点を解決するための手段〕
本発明者らは、前記芳香族ポリエステルが成形時のわず
かの配向によっても複屈折率が高くなるのは、芳香族ポ
リエステルの分子自体が複屈折率が高いためだという知
見に基き、分子自体の複屈折率の低い芳香族ポリエステ
ルを鋭意検討した結果、立体規制された側鎖の芳香環が
主鎖の芳香環の複屈折を打消して、分子自体の複屈折率
を低下させることを見出し、遂に本発明を完成するに到
った。すなわち本発明は、二価カルボン酸またはその塩
化物および下記一般式（Ｉ）で示されるビスフェノール
とを重合して得られる光学材料用芳香族ポリエステルで
ある。Means for Solving Problem C] The present inventors believe that the reason why the aromatic polyester has a high birefringence even with a slight orientation during molding is that the molecules of the aromatic polyester itself have a high birefringence. Based on the knowledge that the birefringence of the molecule itself is low, based on the knowledge that aromatic polyesters have a low birefringence index, they found that the aromatic rings in the sterically-regulated side chains cancel out the birefringence of the aromatic rings in the main chain, and the molecule itself has a low birefringence. It was discovered that the birefringence can be lowered, and the present invention was finally completed. That is, the present invention is an aromatic polyester for optical materials obtained by polymerizing a divalent carboxylic acid or its chloride and a bisphenol represented by the following general formula (I).
本発明において二価カルボッ酸またはその塩化物として
は下記一般式（Ｔ１）で示される化合物が用いられる。In the present invention, a compound represented by the following general formula (T1) is used as the dicarboxylic acid or its chloride.
前期二価カルボ／ｉ！Ｉと前記一般式（１）で示される
ビスフェノールとより本発明の光学材料用芳香族ポリエ
ステルを得る方法としては、界面重合法および溶液重合
法のいずれも採用することができる。Early bivalent carbo/i! As a method for obtaining the aromatic polyester for optical materials of the present invention from I and the bisphenol represented by the general formula (1), both an interfacial polymerization method and a solution polymerization method can be employed.
界面ｍ合法を採用する場合、溶媒としてＣ８ｍＣｆ４−
ｍ（ｍ＝ ０−３＞ 、Ｃｍ ＨｎＣｆｆｉ、−ｎ（
ｎ＝２〜５）、 Ｃｆｆ−Ｃ１’）１（Ｚ’ ＝Ｃｆｆ
１、Ｉ３ｒ、 ｅ＝１〜２）テ示ｉｔ ｈ ６ ハＯ’
ｒ’ ７ 化Ｆｌ化水素を用い、温度−２０℃〜８０℃
、好ましくは一２０℃〜４０℃で重合される。なお反応
の初期および／または後期は８０℃以内に加熱してもよ
い。また触媒としてはトリメチルベンジルアンモニウム
クロリド、トリメチルセチルアンモニウムプロミドなど
の４級アンモニウム塩、トリフェニルメチルホスホニウ
ムクロリドなどの４級ホスホニウム塩、トリエチルアミ
ン、トリーｎ−ブチルアミンオキシドなどの３級アミン
、アミンオキンド、他に４級スルホニウム塩などが用い
られる。さらに酸化防止剤としてハイドロサルファイド
ナトリウム、水素化硼素ナトリウムなどを添加してもよ
い。When using the interfacial m method, C8mCf4- is used as a solvent.
m(m=0-3>, Cm HnCffi, -n(
n=2~5), Cff-C1')1(Z'=Cff
1, I3r, e=1~2) te it h 6 haO'
Using r' 7 Fl hydrogen, temperature -20°C to 80°C
, preferably at -20°C to 40°C. Note that the reaction may be heated to a temperature of 80°C or less during the initial and/or latter stages of the reaction. Catalysts include quaternary ammonium salts such as trimethylbenzylammonium chloride and trimethylcetylammonium bromide, quaternary phosphonium salts such as triphenylmethylphosphonium chloride, tertiary amines such as triethylamine and tri-n-butylamine oxide, amine oxides, and others. Quaternary sulfonium salts and the like are used. Furthermore, sodium hydrosulfide, sodium borohydride, etc. may be added as an antioxidant.
一方、溶液重合法を採用する場合、溶媒としてジメチル
スルホオキシド、ジメチルホルムアミド、ジメチルアセ
トアミド、Ｎ−メチルピロリド７．３−（跣 など
の沸点が重合温度以上である極性溶媒を用い、二価カル
ボ／酸塩化物の分解点以下の温度、２０℃〜２００℃、
好ましくは８０℃〜１８０℃で、マグネシウムクロリド
、塩化亜鉛、塩化錫などの金属ハロゲン化物を触媒とし
て重合される。On the other hand, when employing the solution polymerization method, a polar solvent with a boiling point higher than the polymerization temperature, such as dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methylpyrrolid Temperature below the decomposition point of chloride, 20°C to 200°C,
The polymerization is preferably carried out at 80°C to 180°C using a metal halide such as magnesium chloride, zinc chloride, or tin chloride as a catalyst.
以上の方法によって得られる本発明芳香族ポリエステル
は光学材料用として、たとえば各種レンズ、光ファイバ
、光ディスク、透明電極の基板などに用いることができ
る。The aromatic polyester of the present invention obtained by the above method can be used for optical materials, such as various lenses, optical fibers, optical disks, transparent electrode substrates, and the like.
以下実施例を用いて本発明ｙｆ谷族ポリエステルの製造
方法を具体的に示すが、本発明はこれらに限定されるも
のではない。The method for producing the yf Valley polyester of the present invention will be specifically described below using Examples, but the present invention is not limited thereto.
なお、複屈折率は偏光顕微鏡を備えたセナルモンフンペ
ンセーター（日本地科学社製）を用いナトリウムラップ
を光源として測定した。The birefringence was measured using a Senarmonfunpensator (manufactured by Nippon Geikagaku Co., Ltd.) equipped with a polarizing microscope and using a sodium wrap as a light source.
実施例１゜
フェノールフタレイン７．９６重量部、水酸化ナトリウ
ム２重量部、２５０重量部、ベンジルトリエチルアンモ
ニウム０．０４ ｆｆｌｆｆｉ部および亜ジチオン酸ナ
トリウム０．０４重量部より溶液（Ａ）を調整し、一方
テレフタル酸塩化物２．５４重量部、イソフタル酸塩化
物２．５４重量部および乾燥ジクロルエタン７５重量部
を混合して溶液（ｎ）を調整した。前記溶液（Ａ）を激
しく撹拌しながら溶液（Ｂ）を一度に加えて２０℃で１
０分間反応させた。反応混合物を多量のアセトンに再沈
シフし、析出したポリマーを２回水洗した後減圧乾燥し
た。得られたポリマーは環元比粘度（７エ／−ル／テト
ラクロロエタン（８／４ ｖｏｌ／ｖｏｌ）の０．５ｇ
／ｄＱ溶液とし３０℃で測定した）ηｓｐ／ｃ＝０．６
０、軟化温度（Ｔｓ）２８３°Ｃの芳香族ポリエステル
であった。Example 1 A solution (A) was prepared from 7.96 parts by weight of phenolphthalein, 2 parts by weight of sodium hydroxide, 250 parts by weight, 0.04 parts by weight of benzyltriethylammonium and 0.04 parts by weight of sodium dithionite. On the other hand, a solution (n) was prepared by mixing 2.54 parts by weight of terephthalic acid chloride, 2.54 parts by weight of isophthalic acid chloride, and 75 parts by weight of dry dichloroethane. While vigorously stirring the solution (A), add the solution (B) all at once and heat at 20°C for 1 hour.
The reaction was allowed to proceed for 0 minutes. The reaction mixture was reprecipitated in a large amount of acetone, and the precipitated polymer was washed twice with water and then dried under reduced pressure. The obtained polymer had a ring specific viscosity of 0.5 g (7 ethanol/tetrachloroethane (8/4 vol/vol)).
/dQ solution and measured at 30°C) ηsp/c=0.6
0. It was an aromatic polyester with a softening temperature (Ts) of 283°C.
入
この芳香族ポリエステル２．０ｇをクロロホルムｇ、ｏ
ｇ＋、、溶解しキャスト製膜して、室温で１日乾燥して
フィルムを得た。Add 2.0 g of this aromatic polyester to chloroform (g, o)
g+, melted and cast to form a film, dried at room temperature for 1 day to obtain a film.
該フィルムを２８０℃に加熱、１．５倍に延伸し複屈折
率（Δｎ）を測定したところ３．０であった。The film was heated to 280° C., stretched 1.5 times, and its birefringence (Δn) was measured and found to be 3.0.
実施例２〜４、比較例１〜３
実施例１において第１表に示すビスフェノール成分を用
い、酸成分としてはテレフタル酸塩化物とイソフタル酸
塩化物の等ｆｆｉ混合物またはアジピン酸塩化物を用い
た以外は全て実施例１と同様にして芳香族ポリエステル
を得、フィルム成形した。その結果を第１表に示す。な
お比較例２は市販のポリカーボネート（三菱瓦斯化学社
製：商品名ニーピロノ）を、比較例３はポリメチルメタ
クリレート（協和ガス化学社製：商品名バラペット）を
用いた。Examples 2 to 4, Comparative Examples 1 to 3 In Example 1, the bisphenol components shown in Table 1 were used, and as the acid component, an ffi mixture such as terephthalic acid chloride and isophthalic acid chloride or adipic acid chloride was used. Except for this, an aromatic polyester was obtained in the same manner as in Example 1 and formed into a film. The results are shown in Table 1. Comparative Example 2 used commercially available polycarbonate (manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name: Niepirono), and Comparative Example 3 used polymethyl methacrylate (manufactured by Kyowa Gas Chemical Co., Ltd., trade name: Barapet).
第 １ 表
第１表より明らかなように立体規制された芳香環側鎖を
存する本発明芳香族ポリエステル（実施例１〜４）は複
屈折率が低く軟化温度が高いが、芳香環側鎖のないポリ
エステル（比較例１）は複屈折率が１４．０もあった。Table 1 As is clear from Table 1, the aromatic polyesters of the present invention (Examples 1 to 4) having sterically regulated aromatic ring side chains have a low birefringence and a high softening temperature; The polyester (Comparative Example 1) without the above had a birefringence of as high as 14.0.
また従来より用いられているポリマーは軟化点の低いも
のであった。Furthermore, conventionally used polymers have low softening points.
（発明の効果〕
以上の構成よりなる芳香族ポリエステルは優れた耐熱性
を存するとともに、透明でη屈折が低いため各種の光学
材料として使用することができ、産業界に寄与すること
大である。(Effects of the Invention) The aromatic polyester having the above structure has excellent heat resistance, is transparent and has a low η refraction, and therefore can be used as various optical materials, making a great contribution to industry.
Claims (2)
式（ I ）で示されるビスフェノールとを重合して得ら
れる光学材料用芳香族ポリエステル。 ▲数式、化学式、表等があります▼（ I ） （式中Ｘは▲数式、化学式、表等があります▼、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼ ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
で表わされる 二価の有機基）(1) An aromatic polyester for optical materials obtained by polymerizing a divalent carboxylic acid or its chloride and a bisphenol represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (X in the formula is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
(divalent organic group represented by)
塩化物、イソフタル酸塩化物、アジピン酸塩化物または
セバシン酸塩化物の中から選ばれた少なくとも一種の酸
塩化物である特許請求の範囲第（１）項記載の光学材料
用芳香族ポリエステル。(2) The divalent carboxylic acid or its chloride is at least one acid chloride selected from terephthalic acid chloride, isophthalic acid chloride, adipic acid chloride, or sebacic acid chloride. Aromatic polyester for optical materials as described in (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61137016A JPS62292830A (en) | 1986-06-12 | 1986-06-12 | Aromatic polyester for optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61137016A JPS62292830A (en) | 1986-06-12 | 1986-06-12 | Aromatic polyester for optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62292830A true JPS62292830A (en) | 1987-12-19 |
Family
ID=15188852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61137016A Pending JPS62292830A (en) | 1986-06-12 | 1986-06-12 | Aromatic polyester for optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62292830A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530086A (en) * | 1992-07-30 | 1996-06-25 | Kanebo, Ltd. | Polyester containing 9,9-bis(4-(2-hydroxyalkoxy)phenyl fluorene |
| JP2009242589A (en) * | 2008-03-31 | 2009-10-22 | Unitika Ltd | Film forming resin |
| JP2010162846A (en) * | 2009-01-19 | 2010-07-29 | Sony Corp | Optical information recording medium |
| JP2014205829A (en) * | 2013-03-21 | 2014-10-30 | 三菱化学株式会社 | Resin composition and film using the same |
-
1986
- 1986-06-12 JP JP61137016A patent/JPS62292830A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530086A (en) * | 1992-07-30 | 1996-06-25 | Kanebo, Ltd. | Polyester containing 9,9-bis(4-(2-hydroxyalkoxy)phenyl fluorene |
| JP2009242589A (en) * | 2008-03-31 | 2009-10-22 | Unitika Ltd | Film forming resin |
| JP2010162846A (en) * | 2009-01-19 | 2010-07-29 | Sony Corp | Optical information recording medium |
| JP2014205829A (en) * | 2013-03-21 | 2014-10-30 | 三菱化学株式会社 | Resin composition and film using the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3169121A (en) | Carbonate-carboxylate copolyesters of dihydric phenols and difunctional carboxylic acids | |
| JP2003501532A (en) | Amorphous copolyester with high glass transition temperature and low melt viscosity | |
| US3236808A (en) | Polysulfonate copolymers | |
| US3262914A (en) | Sulfonate-carboxylate copolymers | |
| JPH06502673A (en) | Polyester from terephthalic acid, 2,6-naphthalene dicarboxylic acid, hydroquinone and 4,4'-biphenol | |
| JPH06502668A (en) | Polyester from terephthalic acid, 2,6-naphthalene dicarboxylic acid and hydroquinone | |
| JPS62292830A (en) | Aromatic polyester for optical material | |
| US4552947A (en) | Heat-resisting aromatic polyester and process for preparing the same | |
| JPS6119627A (en) | Fully aromatic polyester and its production | |
| US5177173A (en) | Heat-resting aromatic polyestersulfone and process for preparing the same | |
| US5043413A (en) | Low birefringence polyarylate from polyarylene dicarboxylic acid and polyarylene diphenol | |
| JP2866125B2 (en) | Aromatic polyester copolymer | |
| JPH04211451A (en) | Weather-resistant polymer alloy | |
| JPS63152622A (en) | Method for producing soluble heat-resistant polyarylate | |
| KR101562273B1 (en) | Optical polyester film | |
| US3236809A (en) | Polysulfonate copolymers | |
| JPS63297423A (en) | Polysulfone copolymer and production thereof | |
| JPH0656976A (en) | New polyester and production | |
| JP3906951B2 (en) | Aromatic polyester and method for producing the same | |
| JPH06100675A (en) | Aromatic polyester carbonate and its production | |
| JP2865979B2 (en) | Method for producing aromatic polyester | |
| JPS6377933A (en) | Optical polycarbonate resin molding | |
| JPH01138225A (en) | Resin for optical material | |
| JPH03281524A (en) | Aromatic polyester copolymer | |
| JPH0299556A (en) | Polyarylate-based resin composition |