JP2010538144A - オリゴマーシルセスキオキサンを有するポリイミドポリマー - Google Patents
オリゴマーシルセスキオキサンを有するポリイミドポリマー Download PDFInfo
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- JP2010538144A JP2010538144A JP2010524061A JP2010524061A JP2010538144A JP 2010538144 A JP2010538144 A JP 2010538144A JP 2010524061 A JP2010524061 A JP 2010524061A JP 2010524061 A JP2010524061 A JP 2010524061A JP 2010538144 A JP2010538144 A JP 2010538144A
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- polymer
- polyimide
- polyimide polymer
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- 229920000642 polymer Polymers 0.000 title claims abstract description 266
- 229920001721 polyimide Polymers 0.000 title claims abstract description 160
- 239000004642 Polyimide Substances 0.000 title claims abstract description 156
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 39
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 21
- 125000000524 functional group Chemical group 0.000 claims description 21
- 238000002955 isolation Methods 0.000 claims description 17
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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- 239000010703 silicon Substances 0.000 claims description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
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- 238000001704 evaporation Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 3
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- 229910052796 boron Inorganic materials 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 238000009739 binding Methods 0.000 claims description 2
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 claims 4
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 24
- 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 description 21
- 150000004985 diamines Chemical class 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 17
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- KPDMOOCRWQNXAI-UHFFFAOYSA-N 1,5-diaminocyclohexa-2,4-diene-1-carboxylic acid Chemical compound NC1=CC=CC(N)(C(O)=O)C1 KPDMOOCRWQNXAI-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
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- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
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Abstract
Description
ポリイミドは、多くの望ましい特性を有するポリマーの種類の1つである。一般に、ポリイミドポリマーは、ポリマー主鎖中に窒素原子を含み、この窒素原子は2つのカルボニル炭素に連結しており、これによって窒素原子は隣接するカルボニル基によってある程度安定化される。カルボニル基は、カルボニル炭素と呼ばれる炭素を含み、これは酸素原子に二重結合している。ほとんどのポリイミドは、ポリイミドポリマーの生成に2つの異なる種類のモノマーが使用されるため、AA−BB型ポリマーと見なされている。一方の種類のモノマーは酸モノマーと呼ばれ、通常は二無水物の形態である。他方の種類のモノマーは、通常はジアミン、またはジアミノモノマーである。ポリイミドは、数種類の方法によって合成することができる。芳香族ポリイミドを合成するための従来の二段階方法では、N−メチルピロリドン(NMP)などの極性非プロトン性溶媒が使用される。最初に、ジアミノモノマーを溶媒中に溶解させ、次に二無水物モノマーをこの溶液に加える。ジアミンおよび酸モノマーは、一般にほぼ1:1のモル化学量論で加えられる。
OS化合物または基は、[RSi]n[O1.5]nの一般式を有することを特徴とし、式中、Rは有機置換基を表し、SiおよびOは元素のケイ素および酸素の元素記号を表している。Rは、脂肪族または芳香族であってよく、多種多様な有機化合物を含む。図3に示されるように、ケイ素原子は酸素原子を介して互いに連結しており、R基はケイ素原子に連結している。これらのOS化合物は、有機と無機との複合的な性質を有する。Si−O基によって無機的性質が得られ、結合したR基によって有機的性質が得られる。多くの場合、図4に示されるようにこれらのOS化合物はかご型で存在し、ケイ素原子および酸素原子によって多面体が形成される。OS化合物がかご型または多面体型の場合、R基はかごの外側にあり、Si原子は全体的にかごのコーナーを形成する。
最終ポリマーの特性は、ポリマーの生成に使用されるモノマーの選択によって大部分は決定される。モノマーの選択時に考慮すべき要因としては、溶解性、熱安定性、およびガラス転移温度などの最終ポリマーの特性が挙げられる。考慮すべき他の要因としては、選択されるモノマーの費用および入手しやすさが挙げられる。大量に製造される市販のモノマーは、一般にポリイミドポリマーフィルムの製造費が減少するが、この理由はこのようなモノマーは、実験室規模およびパイロット規模で製造されたモノマーよりも一般に安価となるからである。さらに、市販のモノマーを使用することによって、ポリマー中に組み込まれるモノマーを生成するためのさらなる反応ステップが不要となるので、全体の反応効率が改善される。本発明の利点の1つは、好ましいモノマーが、10,000kg/年を超えることもある市販量で一般に製造されていることである。
OS基のポリマーマトリックス中への組み込みは、前述した理由で有益となることが多い。通常、OS基は多面体かご構造中に組み込まれ、多面体OSはポリマーに結合している。このような場合、OS基は、ポリマーに結合するための官能基を有する少なくとも1つの有機置換基を有する。多面体OSは、2つ以上の官能基を有することも可能であり、このような場合モノマーとして、または架橋成分として使用することができる。例えば、2つのアミン官能基を含む多面体OS基を、ジアミンモノマーとしてポリマーの主鎖中に組み込むことができる。または、第1のOS官能基が第1のポリマー鎖に結合する場合、第2のOS官能基を異なるポリマー鎖に結合させることができ、これによって2つのポリマー鎖が架橋する。ポリマー鎖は、ポリマー鎖を架橋させる他の有機置換基を組み込むことによって架橋させることもできる。
最終ポリマーを形成する方法は、全体的な効率を最大化するためにできるだけ少ない回数の反応および少ない回数の単離を含むべきである。製造プロセス中に使用される容器または釜の数を最小限にすることも、ポリマーの反応および/または単離の回数が最小限となる傾向にあるので、効率が改善されやすい。
前述の方法で製造したポリイミドポリマーは、幾つかの特殊な目的で使用することができる。考慮すべき重要な特性の1つは、ポリマーの色である。ポリイミドポリマーは、通常、50%透過率波長(50%T)と呼ぶことができる特定波長までの短波長側の光を吸収する。50%透過率波長より長い波長を有する光は、一般に、ポリマーが吸収せずに透過するか、またはポリマーによって反射される。50%Tは、電磁放射線の50%がポリマーを透過する波長である。ポリマーは50%Tを超えるほとんどすべての電磁放射線を透過する傾向にあり、ポリマーは50%T未満のほとんどすべての電磁放射線を吸収し、ほぼ50%T波長において透過と吸収の間の急激な遷移が起こる。50%Tを可視スペクトル未満に移動できる場合、このポリマーは非常に透明になる傾向にあるが、50%Tが可視スペクトル内またはこれを超える場合、このポリマーは有色となる。
本明細書に記載された方法は、非常に効率的であり、ポリイミドポリマーの単離が1回のみ、さらには0回となる変法を含む。このことは、ポリイミドポリマーが形成される反応、またはOS基をポリイミドポリマーに結合させる反応、またはこの両方のいずれかの間に、気体としての水を除去することによって行われる。全体のプロセスは、わずか1つまたは2つの釜で完了し、各反応は高収率で進行する。ポリマーの単離を行う場合、これは単純な沈殿および濾過による分離であり、これは比較的効率的となる。クロマトグラフィーや、他のより複雑な分離方法を使用する必要はない。より複雑な分離方法では、1バッチで製造することができる生成物量が限定され、およびバッチを進行できる速度が限定される。好ましいモノマーは市販されており、その結果、比較的安価となり、高い生産速度でより効率的なプロセスが得られる。
Claims (24)
- ポリイミドポリマーの製造方法であって:
(a)少なくとも1種類の酸モノマーを少なくとも1種類のジアミノモノマーと反応させて、ポリマー主鎖が少なくとも1つの非末端結合点を含むようなポリイミドポリマー主鎖を形成するステップであって、結合点がカルボン酸で構成されるステップ;
(b)ステップa)の後で、アミンおよびアルコールからなる群より選択される官能基をポリマー主鎖の結合点と反応させるステップであって、官能基がオリゴマーシルセスキオキサン(OS)化合物に連結されるステップ
を含む、方法。 - ポリイミドポリマーが可溶性である、請求項1の方法。
- ポリマー主鎖が最大1回単離される、請求項1の方法。
- OSが多面体の形態である、請求項1の方法。
- 酸モノマーが4−4’−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(6−FDA)であり、ならびにジアミノモノマーがジアミノ安息香酸(DBA)とp−フェニレンジアミン(p−PDA)との両方である、請求項4の方法。
- ポリイミドポリマーの製造方法であって:
(a)少なくとも1種類の酸モノマーを少なくとも1種類のジアミノモノマーと反応させてポリマー主鎖を形成するステップであって、モノマーは、ポリマー主鎖が非末端結合点を含むように選択されるステップ;
(b)ステップ(a)で得たポリマーをイミド化して可溶性ポリイミドポリマー主鎖を形成するステップ;
(c)ステップ(b)の後、オリゴマーシルセスキオキサン(OS)化合物をポリイミドポリマー主鎖上の結合点と反応させて、OS化合物をポリイミドポリマー主鎖に連結させるステップ;および
(d)ポリマー主鎖の単離を最大1回行うステップ
を含む、方法。 - OSが多面体であり、OSが、一般式(RSi)n−1(R’A)1(O1.5)nを有し、式中、RおよびR’は有機置換基であり、Aはある元素であり、ならびにR’はポリマー主鎖に連結している、請求項6の方法。
- AがSi、Al、B、Ge、Sn、Ti、およびSbからなる群より選択される、請求項7の方法。
- 酸モノマーが4−4’−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(6−FDA)であり、ジアミノモノマーがジアミノ安息香酸(DBA)とp−フェニレンジアミン(p−PDA)との両方であり、ならびにAがケイ素である、請求項7の方法。
- ステップ(b)が、水の蒸発および除去によって、イミド化反応の水を除去することをさらに含む、請求項6の方法。
- ステップ(c)が、水の蒸発および除去によって、OS結合反応の水を除去することをさらに含む、請求項10の方法。
- 結合点がカルボン酸であり、ならびにOS化合物が、アミンおよびアルコールからなる群より選択される少なくとも1つの官能基を含み、前記官能基がカルボン酸結合点と反応することで、OS化合物がポリマー主鎖に連結する、請求項6の方法。
- ポリイミドポリマーであって、
少なくとも1つの非末端フェニル基を含むポリイミドポリマー主鎖;
カルボニル炭素および結合窒素原子を含むアミド結合であって、カルボニル炭素が、単結合によってポリマー主鎖中の非末端フェニル基に連結しており、結合窒素原子が、単結合によってカルボニル炭素に連結しているアミド結合;
互いに連結したケイ素原子および酸素原子を含む少なくとも1つのオリゴマーシルセスキオキサン(OS)化合物;および
OS化合物の各ケイ素原子に連結した有機置換基であって、少なくとも1つの有機置換基が、アミド結合の結合窒素原子に連結している有機置換基
を含む、ポリイミドポリマー。 - OS化合物が多面体型である、請求項13のポリイミドポリマー。
- ポリイミドポリマーが可溶性である、請求項13のポリイミドポリマー。
- ポリイミドポリマーであって、
少なくとも1つの非末端フェニル基を含むポリイミドポリマー主鎖;
カルボニル炭素および結合酸素原子を含むエステル結合であって、カルボニル炭素が、単結合によってポリマー主鎖中の非末端フェニル基に連結しており、結合酸素原子が、単結合によってカルボニル炭素に連結しているエステル結合;
互いに連結したケイ素原子および酸素原子を含む少なくとも1つのオリゴマーシルセスキオキサン(OS)化合物;および
OS化合物の各ケイ素原子に連結した有機置換基であって、少なくとも1つの有機置換基が結合酸素原子に連結することでテザーを形成している有機置換基
を含む、ポリイミドポリマー。 - OS化合物が多面体型である、請求項16のポリイミドポリマー。
- ポリイミドポリマーが可溶性である、請求項16のポリイミドポリマー。
- ポリイミドポリマーであって、次式:
ならびにZZは、直接結合、−O−、−S−、−SO−、−SO2−、−CH2−、−CF2−、−C(CH3)2−、−(CF3)2−、−(CH2)n−、−(CH2CHCH3O)n−、−((CH2)4O)n−、−(Si(CH3)2O)n−、−(SiH(CH3)O)n−、−(SiH(C6H5)O)n−、および−(Si(C6H5)2O)n−からなる群より選択され、ならびにWWは、水素、および次式:
によって表される少なくとも1つの単位を含むポリイミドポリマー主鎖を含む、ポリイミドポリマー。 - OS化合物が、一般式(RSi)n−1(R’A)1(O1.5)nを有し、式中、RおよびR’は有機置換基であり、Aはある元素であり、ならびにR’はポリマー主鎖に連結している、請求項19のポリマー。
- AがSi、Al、B、Ge、Sn、Ti、およびSbからなる群より選択される、請求項20のポリマー。
- OS化合物が多面体型である、請求項19のポリマー。
- ポリイミドポリマーが可溶性である、請求項19のポリマー。
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US11/972,768 US7619042B2 (en) | 2007-09-07 | 2008-01-11 | Polyimide polymer with oligomeric silsesquioxane |
PCT/US2008/050891 WO2009032355A1 (en) | 2007-09-07 | 2008-01-11 | Polyimide polymer with oligomeric silsesquioxane |
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Also Published As
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EP2188330A4 (en) | 2012-08-29 |
US20090069508A1 (en) | 2009-03-12 |
EP2188330A1 (en) | 2010-05-26 |
JP4871414B2 (ja) | 2012-02-08 |
US7619042B2 (en) | 2009-11-17 |
WO2009032355A1 (en) | 2009-03-12 |
EP2433978A1 (en) | 2012-03-28 |
EP2188330B1 (en) | 2016-11-30 |
EP2433978B1 (en) | 2016-07-27 |
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