JP2010037362A - シクロペンテン開環重合体とその製造方法および重合体組成物 - Google Patents
シクロペンテン開環重合体とその製造方法および重合体組成物 Download PDFInfo
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- JP2010037362A JP2010037362A JP2008198591A JP2008198591A JP2010037362A JP 2010037362 A JP2010037362 A JP 2010037362A JP 2008198591 A JP2008198591 A JP 2008198591A JP 2008198591 A JP2008198591 A JP 2008198591A JP 2010037362 A JP2010037362 A JP 2010037362A
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- cyclopentene
- cyclopentene ring
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- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical group C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims abstract description 211
- 229920000642 polymer Polymers 0.000 title claims abstract description 168
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 125000000524 functional group Chemical group 0.000 claims abstract description 57
- 230000000737 periodic effect Effects 0.000 claims abstract description 32
- 239000010954 inorganic particle Substances 0.000 claims abstract description 29
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 19
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 12
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 8
- 238000007142 ring opening reaction Methods 0.000 claims description 71
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 abstract description 6
- 229920002223 polystyrene Polymers 0.000 abstract description 5
- 150000001941 cyclopentenes Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 238000004132 cross linking Methods 0.000 description 22
- -1 aluminum compound Chemical class 0.000 description 21
- 229920001971 elastomer Polymers 0.000 description 20
- 239000005060 rubber Substances 0.000 description 20
- 239000000377 silicon dioxide Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 14
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- 229910052717 sulfur Inorganic materials 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
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- 229910052736 halogen Inorganic materials 0.000 description 5
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 125000005842 heteroatom Chemical group 0.000 description 3
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- 238000004898 kneading Methods 0.000 description 3
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- 239000002184 metal Substances 0.000 description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
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- YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QHORRKSZGBYGPH-UHFFFAOYSA-L benzylidene(dichloro)ruthenium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1 QHORRKSZGBYGPH-UHFFFAOYSA-L 0.000 description 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
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- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 description 1
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- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】シクロペンテンを開環重合してなる繰返し単位を含有するシクロペンテン開環重合体であって、重合体鎖末端に周期表第15族の原子、周期表第16属の原子、およびケイ素原子からなる群から選ばれる原子を含有する官能基を有し、かつ、ゲルパーミエーションクロマトグラフィーで測定される、ポリスチレン換算の数平均分子量(Mn)が10,000〜1,000,000であるシクロペンテン開環重合体。
【選択図】なし
Description
テトラヒドロフランを溶媒とするゲル・パーミエーション・クロマトグラフィー(GPC)により、重合体の数平均分子量(Mn)、重量平均分子量(Mw)および分子量分布(Mw/Mn)を、ポリスチレン換算値として測定した。
シクロペンテン開環重合体について、1H−NMRスペクトルの測定を行い、得られたスペクトルから主鎖中の炭素−炭素二重結合に帰属されるピークの積分値と、重合体鎖末端に導入された官能基に帰属されるピークの積分値と、数平均分子量(Mn)とから、一本の重合体鎖が2個の末端を有するものとして、(特定官能基が導入されたシクロペンテン開環重合体末端数/シクロペンテン開環重合体鎖末端全数)の百分率を官能基の導入率として算出した。
混練した重合体組成物2部を1000部のトルエンに72時間浸漬した後、100メッシュのフィルターで濾過して、フィルター残留部(フィルター上に残留したろ物)の重量を測定した。重合体鎖末端に官能基を導入していないシクロペンテン開環重合体を用いた場合におけるフィルター残留部重量を100としたときの、測定対象であるシクロペンテン開環重合体を用いた場合におけるフィルター残留部重量を求め、無機粒子親和性の指標とした。
窒素雰囲気下、磁気攪拌子を入れた耐圧ガラス反応容器に、シクロペンテン100部とアリルトリメトキシシラン0.10部を加えた。次に、トルエン10部に溶解した(1,3−ジメシチルイミダゾリジン−2−イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド0.062部を加え、重合温度0℃で10時間重合した。過剰のビニルエチルエーテルを加えて重合を停止した後、2,6−ジ−t−ブチル−p−クレゾール(BHT)を含む大過剰のイソプロパノールに注いだ。そして、沈殿したポリマーを回収し、イソプロパノールで洗浄後、40℃で3日間、真空乾燥することにより、25部のシクロペンテン開環重合体を得た。得られたシクロペンテン重合体は、Mn=45,600、Mw/Mn=1.89であった。重合体鎖末端への官能基の導入率は49%〔官能基を1つ含有する化合物(アリルトリメトキシシラン)を用いたので、理論上の最大値は50%である。〕であった。
重合温度を10℃、重合時間を20時間としたこと以外は、実施例1と同様にして重合を行い、89部のシクロペンテン開環重合体を得た。得られたシクロペンテン重合体は、Mn=137,200、Mw/Mn=1.50であった。重合体鎖末端への官能基の導入率は47%であった。
アリルトリメトキシシラン0.10部を2−ブテン−1,4−ジカルボン酸0.09部に代えたこと以外は実施例1と同様にして重合を行い、20部のシクロペンテン開環重合体を得た。得られたシクロペンテン重合体は、Mn=36,800、Mw/Mn=1.68であった。重合体鎖末端への官能基の導入率は95%〔官能基を2つ含有する化合物(2−ブテン−1,4−ジカルボン酸)を用いたので、理論上の最大値は100%である。〕であった。
重合温度80℃としたこと以外は、実施例1と同様にして重合反応を行い、15部のシクロペンテン開環重合体を得た。得られたシクロペンテン重合体は、Mn=3,800、Mw/Mn=1.68であった。重合体鎖末端への官能基の導入率は5%以下であった。
アリルトリメトキシシラン0.10部に代えて、1−ヘキセン0.051部を加えたこと以外は、実施例1と同様にして重合を行い、重合体末端に官能基が導入されていないシクロペンテン開環重合体を合成した。得られたシクロペンテン重合体の収量は21部であり、Mn=37,800、Mw/Mn=1.87であった。
容量250mlのブラベンダータイプミキサー中で、実施例1、2および参考例1で得たシクロペンテン開環重合体100部を30秒素練りし、次いでプロセスオイル(フッコールM・フェレックスM:富士興産社製)10部、カーボン−シリカ デュアルフェイズフィラー(CRX2000、キャボット社製)40部およびシランカップリング剤(Si69、デグッサ社製)2.5部を添加して、110℃を開始温度として2分間混合後、カーボン−シリカ デュアルフェイズフィラー(CRX2000、キャボット社製)20部、酸化亜鉛(亜鉛華#1、本荘ケミカル社製、粒度0.4μm)3部、ステアリン酸2部および老化防止剤(ノクラック6C、大内新興社製)2部を添加し、さらに2分間混練した。混練した重合体組成物2部を1000部のトルエンに72時間浸漬した後、100メッシュのフィルターで濾過して、フィルター残留部の重量を測定した。参考例1の重合体を用いた場合の残留部重量を100としたときの、実施例1の重合体を用いた場合(実施例4)、および実施例2の重合体を用いた場合(実施例5)の残留部量はそれぞれ115、108であった。
Claims (3)
- シクロペンテンを開環重合してなる繰返し単位を含有するシクロペンテン開環重合体であって、重合体鎖末端に周期表第15族の原子、周期表第16属の原子、およびケイ素原子からなる群から選ばれる原子を含有する官能基を有し、かつ、ゲルパーミエーションクロマトグラフィーで測定される、ポリスチレン換算の数平均分子量(Mn)が10,000〜1,000,000であるシクロペンテン開環重合体。
- 請求項1に記載のシクロペンテン開環重合体を製造する方法であって、周期表第15族の原子、周期表第16属の原子、およびケイ素原子からなる群から選ばれる原子を含有する官能基とエチレン性不飽和結合とを分子中に含有する化合物の存在下で、ルテニウム−カルベン錯体を触媒として用いて、20℃未満の重合温度でシクロペンテンを開環重合するシクロペンテン開環重合体の製造方法。
- 請求項1に記載のシクロペンテン開環重合体と無機粒子とを含有してなる重合体組成物。
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