JP2006117917A - ポリカルボシランおよびその製造方法 - Google Patents
ポリカルボシランおよびその製造方法 Download PDFInfo
- Publication number
- JP2006117917A JP2006117917A JP2005263629A JP2005263629A JP2006117917A JP 2006117917 A JP2006117917 A JP 2006117917A JP 2005263629 A JP2005263629 A JP 2005263629A JP 2005263629 A JP2005263629 A JP 2005263629A JP 2006117917 A JP2006117917 A JP 2006117917A
- Authority
- JP
- Japan
- Prior art keywords
- polycarbosilane
- general formula
- acid
- following general
- repeating structural
- 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
- 229920003257 polycarbosilane Polymers 0.000 title claims abstract description 72
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002994 raw material Substances 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 abstract description 15
- 229910052799 carbon Inorganic materials 0.000 abstract description 12
- 150000001721 carbon Chemical group 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 18
- 230000003595 spectral effect Effects 0.000 description 17
- 229910018557 Si O Inorganic materials 0.000 description 14
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000010354 integration Effects 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910002808 Si–O–Si Inorganic materials 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 238000010304 firing Methods 0.000 description 4
- -1 lithium aluminum hydride Chemical compound 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 238000006462 rearrangement reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 229910008045 Si-Si Inorganic materials 0.000 description 2
- 229910006411 Si—Si Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
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- 229910021529 ammonia Inorganic materials 0.000 description 2
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- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
【解決手段】本発明のポリカルボシランは、ケイ素原子と炭素原子とが交互に連続してなる主鎖を有し、SiH基含有カルボシランの繰り返し構造単位、ジメチルカルボシランの繰り返し構造単位、およびSiO基含有カルボシランの繰り返し構造単位を有する。ジメチルカルボシランとSiH基含有シランの構造単位を有する原料ポリマーに塩基性触媒の存在下で水および/またはアルコールを反応させて製造する。
【選択図】なし
Description
ジャーナル オブ マテリアルズ サイエンス,1978年,第13巻,p.2569−2576(Journal of Materials Science, 2569-2576, Vol.13, 1978) オーガノメタリクス,1991年,第10巻,p.1336−1344(Organometallics, 1336-1344, Vol.10, 1991) ジャーナル オブ オーガノメタリック ケミストリー,1996年,第521巻,p.1−10(Journal of Organometallic Chemistry, 1-10, Vol.521, 1996)
ケイ素原子と炭素原子とが交互に連続してなる主鎖を有し、下記一般式(1)で表される繰り返し構造単位、下記一般式(2)で表される繰り返し構造単位、および下記一般式(3)で表される繰り返し構造単位を有する。
ケイ素原子と炭素原子とが交互に連続してなる主鎖を有し、下記一般式(1)で表される繰り返し構造単位および下記一般式(2)で表される繰り返し構造単位を有する原料ポリマーに、塩基性触媒の存在下で水および/またはアルコールを反応させる工程を含む。
本発明のポリカルボシランは、ケイ素原子と炭素原子とが交互に連続してなる主鎖を有し、下記一般式(1)で表される繰り返し構造単位、下記一般式(2)で表される繰り返し構造単位、および下記一般式(3)で表される繰り返し構造単位を有する。すなわち、本発明のポリカルボシランは、ケイ素原子と炭素原子とが交互に連続してなる主鎖と、主鎖のケイ素原子に結合する水素原子、酸素原子、および炭素原子を含む側鎖とを含む。
本発明のポリカルボシランの製造方法は、ケイ素原子と炭素原子とが交互に連続してなる主鎖を有し、下記一般式(1)で表される繰り返し構造単位および下記一般式(2)で表される繰り返し構造単位を有する原料ポリマーに、塩基性触媒の存在下で水および/またはアルコールを反応させる工程を含む。
以下、本発明の実施例について説明するが、本発明はこれらの実施例に限定されるものではない。実験例および比較例における各評価は以下に示す方法で行なった。
ポリカルボシランの重量平均分子量(Mw)および数平均分子量(Mn)は、下記条件によるゲルパーミエーションクロマトグラフィー(GPC)法により測定した。
試料:テトラヒドロフランを溶媒として使用し、重合体1[g]を、100[cc]のテトラヒドロフランに溶解して調製した。
標準ポリスチレン:米国プレッシャーケミカル社製の標準ポリスチレンを使用した。
装置:米国ウオーターズ社製の高温高速ゲル浸透クロマトグラム(モデル150−CALC/GPC)
カラム:昭和電工(株)製のSHODEX A−80M(長さ50cm)
測定温度:40℃流速:1cc/分
下記の装置を用いて、1H NMRスペクトル(500MHz)および29Si NMRスペクトル(100MHz)の測定を行なった。
装置:BRUKER AVANCE 500型(ブルカー(Bruker)社製)
(株)日本カーボン社製ニプシType−S(商品名,以下「原料ポリマー1」ともいう)20[g]をテトラヒドロフランに溶解させて400[g]とし、ここに1.0[mol/L]のTMAH(テトラメチルアンモニウムハイドロオキサイド)水溶液を5.0[ml]加えた後、この反応液を50℃で3時間加熱した。次に、この反応液を室温まで冷却した後、2.0[mol/L]のシュウ酸水溶液10[ml]を加えて反応を停止させた。次いで、この反応液にシクロヘキサノン100[g]と0.02[mol/L]のシュウ酸水溶液400[g]とを加えて振り混ぜた後、静置して有機相と水相とに分離した。この有機相を取り出して濃縮することにより、実験例1のポリカルボシラン19.8[g]を得た。
29Si NMR(重ベンゼン中)スペクトルデータ:-40〜-30ppm(broad),-20〜10ppm(broad),10〜30ppm(broad);後者2つのピークは重なっている。3つのピークの積分比はおよそ3:6:1であった。
分子量(GPC):Mw=7,100,Mn=720
(株)日本カーボン社製ニプシType−UH(商品名,以下「原料ポリマー2」ともいう)20[g]をジオキサンに溶解させて400[g]とし、これにピリジン3.0[ml]および水4.0[ml]を加えた後、この反応液を80[℃]で5時間加熱した。次に、この反応液を室温まで冷却した後、2.0 [mol/L]の酢酸水溶液10[ml]を加えて反応を停止させた。次いで、この反応液にシクロヘキサノン100[g]と0.02[mol/L]の酢酸水溶液400[g]とを加えて振り混ぜた後、静置して有機相と水相とに分離した。この有機相を取り出して濃縮することにより、実験例2のポリカルボシラン19.3[g]を得た。
29Si NMR(重ベンゼン中)スペクトルデータ:-40〜-30ppm(broad),-20〜10ppm(broad),10〜30ppm(broad);後者2つのピークは重なっている。3つのピークの積分比はおよそ3.5:6:0.5であった。
分子量(GPC):Mw=10,200、Mn=1,500
(株)日本カーボン社製ニプシType−S(原料ポリマー1)の理化学的データ
1H NMR(重ベンゼン中)スペクトルデータ:-2.0〜1.0ppm(broad),3.5-4.5ppm(broad)
29Si NMR(重ベンゼン中)スペクトルデータ:-40〜-30ppm(broad),-20〜10ppm(broad);2つのピークの積分比はおよそ4:6であった。
分子量(GPC):Mw=3,000,Mn=500
比較例1(原料ポリマー1)の構造およびNMRスペクトルデータとの帰属を、下記一般式(20)および表5,6に示す。なお、下記一般式(20)において、xは40%(0.4)であり、yは60%(0.6)である。
(株)日本カーボン社製ニプシType−UH(原料ポリマー2)の理化学的データ
1H NMR(重ベンゼン中)スペクトルデータ:-2.0〜1.0ppm(broad),3.5-4.5ppm(broad)
29Si NMR(重ベンゼン中)スペクトルデータ:-40〜-30ppm(broad),-20〜10ppm(broad);2つのピークの積分比はおよそ4:6であった。
分子量(GPC):Mw=5,000、Mn=1,000
比較例2(原料ポリマー2)の構造およびNMRスペクトルデータとの帰属を、下記一般式(21)および表7,8に示す。なお、下記一般式(21)において、xは40%(0.4)であり、yは60%(0.6)である。
Claims (5)
- 請求項1または2において、
重量平均分子量が300〜1,000,000であり、有機溶剤に可溶であるポリカルボシラン。
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003501518A (ja) * | 1999-06-07 | 2003-01-14 | アライドシグナル インコーポレイテッド | ポリカルボシランから生じた低誘電率ポリオルガノシリコンコーティング |
-
2005
- 2005-09-12 JP JP2005263629A patent/JP4900557B2/ja active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003501518A (ja) * | 1999-06-07 | 2003-01-14 | アライドシグナル インコーポレイテッド | ポリカルボシランから生じた低誘電率ポリオルガノシリコンコーティング |
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