JP2009221309A - 含リンエステル基含有テトラカルボン酸またはその二無水物及び含リンポリエステルイミド - Google Patents
含リンエステル基含有テトラカルボン酸またはその二無水物及び含リンポリエステルイミド Download PDFInfo
- Publication number
- JP2009221309A JP2009221309A JP2008065852A JP2008065852A JP2009221309A JP 2009221309 A JP2009221309 A JP 2009221309A JP 2008065852 A JP2008065852 A JP 2008065852A JP 2008065852 A JP2008065852 A JP 2008065852A JP 2009221309 A JP2009221309 A JP 2009221309A
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- JP
- Japan
- Prior art keywords
- phosphorus
- formula
- dianhydride
- ester group
- bis
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 88
- 239000011574 phosphorus Substances 0.000 title claims abstract description 88
- 229920003055 poly(ester-imide) Polymers 0.000 title claims abstract description 44
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 125000004185 ester group Chemical group 0.000 title claims abstract description 28
- 150000000000 tetracarboxylic acids Chemical class 0.000 title claims abstract description 16
- 239000002243 precursor Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009792 diffusion process Methods 0.000 abstract description 3
- -1 phosphazene compound Chemical class 0.000 description 30
- 239000002904 solvent Substances 0.000 description 23
- 229920001721 polyimide Polymers 0.000 description 20
- 239000004642 Polyimide Substances 0.000 description 18
- 239000010408 film Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920005575 poly(amic acid) Polymers 0.000 description 11
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000006159 dianhydride group Chemical group 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
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- 238000005809 transesterification reaction Methods 0.000 description 4
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical group C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
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- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
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- KOUQMRHSPOKPBD-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 KOUQMRHSPOKPBD-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】式(1)または(2)で表される含リンエステル基含有テトラカルボン酸またはその二無水物、それを利用して製造される含リンポリエステルイミド前駆体および含リンポリエステルイミド。
【選択図】なし
Description
即ち本発明は以下に示すものである。
〔式(1)及び(2)中、
Arは、式(3):
より選択される三価の芳香族基を表し、
式(1)〜(3)中、R1、R2、R3、R4、及びR5は、同一または異なって、水素原子或いは炭素数1〜4のアルキル基を表す〕。
(式(5)中、Arは式(1)及び(2)におけるのと同義であり、R1及びR2は式(1)〜(3)におけるのと同義であり、Xは、二価の芳香族基、脂環式基または脂肪族基を表し、Rは水素原子、或いは炭素数1〜4のアルキル基を表す。)で表される反復単位を有する含リンポリエステルイミド前駆体。
本発明の含リンエステル基含有テトラカルボン酸またはその二無水物は、式(1)または(2)で表される。ここで、R1、R2及びR3として好ましいのは、水素、メチル、エチルである。
(式(6)中、Arは式(1)及び(2)におけるのと同義であり、R1及びR2は式(1)〜(3)におけるのと同義であり、Raは、同一または異なって、炭素数1〜4のアルキル基を表す)で表される含リン芳香族アルカンエステルと、式(7):
で示されるトリメリット酸無水物とを、相間移動触媒の存在下、溶媒中でエステル交換反応させて製造することができる。
(式(8)中、Arは式(1)及び(2)におけるのと同義であり、R1及びR2は式(1)〜(3)におけるのと同義である。)
で表される化合物を塩化アセチル等のハロゲン化アセチルによりアセトキシ化することで容易に製造することができる。
本発明の含リンポリエステルイミド前駆体は、式(5)で表される反復単位を有する。式(5)におけるXは、任意の二価の芳香族基、脂環式基又は脂肪族基であり、合成原料のジアミンに由来する。Xとして特に好ましいのは、二価の芳香族基としては、4,4‘−オキシジアニリンであり、二価の脂環式基としては、シクロヘキサンジアミンであり、二価の脂肪族基としては、ヘキサメチレンジアミンである。
本発明の含リンポリエステルイミドは、式(4)で表される反復単位を有する。式(4)におけるXは、式(5)におけるのと同様である。含リンポリエステルイミドは、式(4)で表される反復単位を、全反復単位に対して、好ましくは5%以上、更に好ましくは50%以上、もっとも好ましくは100%含む。含リンポリエステルイミドは、有機溶媒に不溶となり、粘度の測定ができない場合もあるが、溶媒可溶の場合は好ましくは1000mPa・s以上、更に好ましくは1000〜50000mPa・s、もっとも好ましくは1000〜30000mPa・sの粘度を有する。含リンポリエステルイミドは難燃性、高熱拡散性を有する。
1H−NMRスペクトル:日本電子社製 核磁気共鳴装置 JNM−AL400 (DMSO−d6)
燃焼試験:UL規格に準じて判定した。
熱拡散率:(株)アイフェイズ社製 アイフェイズモバイル
ガラス転位温度:(株)島津製作所製 DSC−60 (昇温速度:10℃/分、窒素ガス中)
粘度:東機産業(株)製 B形粘度計 (測定温度25℃)
攪拌機、温度計、蒸留用冷却管、窒素ガス導入管を付けた四つ口フラスコに含リン芳香族アルカンエステル(Arが下式:
で示され、RaがCH3である式(6)で表される化合物:マナック社製)32.43g(0.10モル)、トリメリット酸無水物38.43g(0.20モル)、1,2,4−トリクロロベンゼン120g及び臭化テトラフェニルホスホニウム0.42gを仕込み、窒素雰囲気下210℃で8時間反応させた。反応生成物を濾別し、粗製物を得た。粗製物をジメチルホルムアミド10%を含むトルエン溶液で1時間還流洗浄し、冷却後、濾別した。得られたウエット品を180℃で乾燥し、目的物57.0gを得た。本化合物の構造はNMRにて確認した(図1)。融点:308.0℃。
含リン芳香族アルカンエステルとして、Arが下式:
で示され、RaがCH3である式(6)で表される化合物45.84g(0.10モル)を用いた以外、実施例1に記載した方法に従って、本発明の式(2)で表される含リンエステル基含有酸二無水物(*5:TAHCNQ)を合成し、目的物62.1gを得た。本化合物の構造はNMRにて確認した(図2)。融点:311.2℃。
攪拌機、温度計、冷却管、窒素ガス導入管を付けた四つ口フラスコに、*2:ODA(和歌山精化工業(株)製)920.02g(0.1モル)、N−メチル−2−ピロリドン350gを仕込み、溶解させた。次に、同フラスコ内に、実施例1で得られた含リンエステル基含有酸二無水物(*1:TAHCHQ)67.25g(0.1モル)を投入した。この時、フラスコ内の温度は20℃〜45℃に保たれ、8時間攪拌を続けて反応を終了した。得られたポリアミック酸を含む反応液の粘度(B−型粘度計による)は100000mPa・sであった。続けて、このポリアミック酸をガラス板に塗布し80℃5分、130℃5分、180℃5分、210℃5分、260℃10分、310℃10分と順番に熱風乾燥機内で加熱して、熱イミド化を行った。熱イミド化の後、ガラス板からフイルムを引き剥がし、厚みを測定したところ20μmであった。DSCにより、このフイルムのガラス転位温度(Tg)を測定したところ220℃であった。このフイルムの燃焼性をUL規格に準じて判定したところ、94VTM−0であった。また、このフイルムの熱拡散率を測定したところ1.23E−7であった。
攪拌機、温度計、蒸留用冷却管、窒素ガス導入管を付けた四つ口フラスコに、実施例1で得られたTAHCHQ13.5g(0.02モル)、*3:ODPA(マナック(株)製)55.84g(0.18モル)、混合キシレン125g、N-メチル-2-ピロリドン140gを仕込み、この中にα,ω―ビス(3−アミノプロピル)ポリジメチルシロキサン(信越化学化学工業(株)製KF−8010 アミン当量415)を49.8g(0.06モル)を投入し、40℃以下で4時間攪拌した。次に、*4:BAPP(和歌山精化工業(株)製)57.47g(0.14モル)を投入して、さらに40℃以下で攪拌を4時間続けた。得られたポリアミック酸を含む反応液の粘度(B−型粘度計による)は10000mPa・sであった。さらに系内を200℃まで1時間を要して加熱攪拌し、200℃で6時間攪拌を継続した。途中留出してくる溶媒、水は蒸留用冷却管を通して系外に排出した。加熱終了後、N−メチル−2−ピロリドンで希釈して約30%濃度のポリイミド溶液を得た。得られた含リンポリエステルイミド溶液の粘度は3000mPa・sであった。この溶液をガラス板に塗布し80℃5分、130℃3分、180℃3分、210℃3分、260℃10分の順番で熱風乾燥機内で乾燥することにより溶媒を取り除いた。乾燥後、ガラス板からフイルムを引き剥がし、厚みを測定したところ20μmであった。DSCにより、このフイルムのガラス転位温度(Tg)を測定したところ130℃であった。このフイルムの燃焼性をUL規格に準じて測定したところ94VTM−1であった。
TAHCHQを使用しないで、ODPAの使用量を0.2モルに変えた以外は実施例4と同様の方法でフイルムを作成した。DSCにより、このフイルムのガラス転位温度(Tg)を測定したところ130℃であった。このフイルムの燃焼性をUL規格に準じて判定したところ、燃焼したので難燃性は無かった。
リンを含有しない汎用ポリエステルイミドである東レ・デュポン(株)製カプトン(登録商標)Hの熱拡散率を測定したところ8.18E−8であった。
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