JP5522049B2 - 重合性組成物、架橋性成形体、架橋成形体、及び架橋成形体複合体 - Google Patents
重合性組成物、架橋性成形体、架橋成形体、及び架橋成形体複合体 Download PDFInfo
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- JP5522049B2 JP5522049B2 JP2010533934A JP2010533934A JP5522049B2 JP 5522049 B2 JP5522049 B2 JP 5522049B2 JP 2010533934 A JP2010533934 A JP 2010533934A JP 2010533934 A JP2010533934 A JP 2010533934A JP 5522049 B2 JP5522049 B2 JP 5522049B2
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/14—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers obtained by ring-opening polymerisation of carbocyclic compounds having one or more carbon-to-carbon double bonds in the carbocyclic ring, i.e. polyalkeneamers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
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Description
本発明の目的は、高い機械的強度を有し、なおかつボイドが少ない、架橋成形体及び架橋成形体複合体の製造に有用な、重合性組成物及び架橋性成形体、並びに、それらを用いて得られる、架橋成形体及び架橋成形体複合体を提供することにある。
〔1〕シクロオレフィンモノマー、メタセシス重合触媒、架橋剤、および、末端不飽和基と極性基とを有する化合物を含むサイジング剤と予め接触させてなる炭素繊維を含有してなる重合性組成物、
〔2〕シクロオレフィンモノマーが、架橋性の炭素−炭素不飽和結合を1以上有するシクロオレフィンモノマーを含むものである前記〔1〕記載の重合性組成物、
〔3〕連鎖移動剤をさらに含む前記〔1〕または〔2〕記載の重合性組成物、
〔4〕サイジング剤の末端不飽和基がビニル基および/またはビニリデン基であり、極性基がエポキシ基および/またはイソシアネート基である前記〔1〕〜〔3〕いずれか記載の重合性組成物、
〔5〕前記〔1〕〜〔4〕いずれかに記載の重合性組成物を重合してなる架橋性成形体、
〔6〕前記〔5〕に記載の架橋性成形体を架橋してなる架橋成形体、並びに
〔7〕前記〔6〕に記載の架橋成形体とその他の部材とを含んでなる架橋成形体複合体、
を提供するものである。
本発明の重合性組成物は、シクロオレフィンモノマー、メタセシス重合触媒、架橋剤、及び、末端不飽和基と極性基とを有する化合物を含むサイジング剤と予め接触させてなる炭素繊維を含有してなる。
本発明に使用されるシクロオレフィンモノマーは、炭素原子で形成される脂環構造を有し、かつ該脂環構造中に重合性の炭素−炭素二重結合を1つ有する化合物である。本明細書において「重合性の炭素−炭素二重結合」とは、連鎖重合(メタセシス開環重合)可能な炭素−炭素二重結合をいう。
シクロオレフィンモノマーは、アルキル基、アルケニル基、アルキリデン基、及びアリール基などの、炭素数1〜30の炭化水素基や、カルボキシル基又は酸無水物基などの極性基を置換基として有していてもよい。
これらのシクロオレフィンモノマーは、それぞれ単独で、あるいは2種以上を組み合わせて用いることができる。
本発明の重合性組成物に配合するシクロオレフィンモノマー中、架橋性の炭素−炭素不飽和結合を1以上有するシクロオレフィンモノマーと架橋性の炭素−炭素不飽和結合を持たないシクロオレフィンモノマーとの配合割合は所望により適宜選択されるが、重量比(架橋性の炭素−炭素不飽和結合を1以上有するシクロオレフィンモノマー/架橋性の炭素−炭素不飽和結合を持たないシクロオレフィンモノマー)で、通常、5/95〜100/0、好ましくは10/90〜90/10、より好ましくは15/85〜70/30の範囲である。当該配合割合がかかる範囲にあれば、得られる架橋成形体や架橋成形体複合体において、耐熱性、及び耐クラック性等の特性を高度に向上させることができ、好適である。
重合性組成物を構成するメタセシス重合触媒は、シクロオレフィンモノマーを、メタセシス開環重合させるものであれば特に限定されない。
メタセシス重合触媒としては、遷移金属原子を中心にして、イオン、原子、多原子イオン及び/又は化合物が複数結合してなる錯体が挙げられる。遷移金属原子としては、5族、6族及び8族(長周期型周期表、以下同じ。)の原子が使用される。それぞれの族の原子は特に限定されないが、5族の原子としては、好ましくはタンタルが挙げられ、6族の原子としては、好ましくは、モリブデンやタングステンが挙げられ、8族の原子としては、好ましくは、ルテニウムやオスミウムが挙げられる。
活性剤の使用量は、モル比(メタセシス重合触媒中の金属原子:活性剤)で、通常、1:0.05〜1:100、好ましくは1:0.2〜1:20、より好ましくは1:0.5〜1:10の範囲である。
本発明で使用される架橋剤は、本発明の重合性組成物を重合反応に供して得られる重合体(シクロオレフィンポリマー)において架橋反応を誘起する目的で使用される。従って、該重合体は、後架橋可能な熱可塑性樹脂となる。ここで「後架橋可能な」とは、該樹脂を加熱することにより架橋反応を進行させて架橋樹脂になし得ることを意味する。前記重合体をマトリックス樹脂とする本発明の架橋性成形体は、加熱により溶融し、高粘度であるため、その形状は保持する一方、任意の部材を接触させた場合、その表面では、該部材の形状に対し追従性を発揮し、最終的に架橋して硬化する。本発明の架橋性成形体のかかる特性は、例えば、本発明の架橋性成形体を積層し、加熱して溶融、架橋して得られる積層体において層間密着性の向上に寄与するものと考えられる。
本発明に用いられるサイジング剤は、末端不飽和基と極性基とを有する化合物(以下、化合物Aという場合がある。)を含有してなる。末端不飽和基とは、化合物Aの分子末端に存在する、不飽和基、すなわち、脂肪族炭素−炭素二重結合基又は脂肪族炭素−炭素三重結合基をいう。末端不飽和基は、通常、ビニル基及び/又はビニリデン基であり、ラジカル架橋反応性に優れることから、ビニル基、アクリル基、及びメタクリル基からなる群から選ばれる少なくとも1種として存在するのが好ましく、ビニル基及び/又はメタクリル基として存在するのがより好ましい。極性基としては、炭素繊維の表面と化学結合し得るものであれば特に限定されるものではないが、炭素繊維表面の水酸基、カルボキシル基、及びケトン基などの官能基との反応性に優れることから、エポキシ基、イソシアネート基、オキサゾリン基、スルホン酸基、酸無水物基、チオール基、メルカプト基、オキセタン基、ラクトン基、アミド結合、イミド結合、ウレタン結合、及びウレア結合からなる群から選ばれる少なくとも1種が好ましく、エポキシ基、イソシアネート基、オキサゾリン基、酸無水物基、及びチオール基からなる群から選ばれる少なくとも1種がより好ましく、エポキシ基及び/又はイソシアネート基が特に好ましい。本発明においては、マトリックス樹脂との反応性及び相溶性、並びに炭素繊維表面との反応性に優れることから、通常、末端不飽和基がビニル基及び/又はビニリデン基であり、極性基がエポキシ基及び/又はイソシアネート基であるサイジング剤が好適に用いられる。
炭素繊維の表面状態は、特に限定されず、平滑でも凹凸であってもよい。アンカー効果が期待できることから、凹凸であるのが好ましい。この凹凸の程度は適宜選択すればよい。炭素繊維表面への凹凸の導入は、例えば、上記した溶液中の酸化反応の際に、電流密度を変化させることや、溶液のpHを制御することにより同時に行うことができる。
本発明において炭素繊維は、サイジング剤と予め接触させて、その表面にサイジング剤を付着させた後、重合性組成物の調製に用いる。すなわち、「サイジング剤と予め接触させてなる炭素繊維」とは、重合性組成物の調製に使用する前にサイジング剤と接触させ、サイジング剤が、その表面に付着した状態の炭素繊維をいう。
本発明に用いる炭素繊維は、ピッチ、レーヨン、リグニン、及びポリアクリロニトリルなどのいずれの原材料からなるものであってもよい。また、その種類は、例えば、高強度タイプ(低弾性炭素繊維)、中高弾性炭素繊維、及び超高弾性炭素繊維などのいずれの種類のものでもよい。さらに、その形態は、長繊維、短繊維、織物、編み物、及びシート状物など、いずれのものでもよく、特に限定されない。シート状物としては、例えば、織布、一方向配列シート、不織布、及びマットなどや、これらを組み合わせたものが挙げられる。織り組織は特に限定されず、平織り、綾織り、及び朱子織り等の他、これら原組織を変化させたものでもよい。また、緯、経糸共に炭素繊維でもよく、又は炭素繊維以外の繊維との混織を使用することもできる。炭素繊維以外の繊維としては、ガラス繊維、チラノ繊維、及びSiC繊維などの無機繊維、アラミド、ポリエステル、ポリプロピレン、ナイロン、アクリル、ポリイミド、及びビニロンなどの有機繊維などが挙げられる。さらに、2種以上からなる複合繊維と炭素繊維との混織を使用することもできる。炭素繊維の取扱性やシクロオレフィンモノマーの含浸性を良好に保つ観点から、経糸として炭素繊維を用いた場合、該炭素繊維より低い引張弾性率の繊維を緯糸として用い、シート状物を調製するのが好ましい。
本発明の重合性組成物には、各種の添加剤、例えば、充填剤、連鎖移動剤、重合反応遅延剤、ラジカル架橋遅延剤、強化材、改質剤、酸化防止剤、難燃剤、着色剤、及び光安定剤などを含有させることができる。
これらの連鎖移動剤は、それぞれ単独で、あるいは2種以上を組み合わせて用いることができる。本発明の重合性組成物への連鎖移動剤の配合量としては、配合するシクロオレフィンモノマー100重量部に対して、通常、0.01〜10重量部、好ましくは0.1〜5重量部である。
また、シクロオレフィンモノマーのうち、分子内に1,5−ジエン構造や1,3,5−トリエン構造を有するモノマーは重合反応遅延剤としても機能する。このような化合物としては、1,5−シクロオクタジエンや5−ビニル−2−ノルボルネンなどが挙げられる。
本発明の架橋性成形体は、前記重合性組成物を重合することによって得られる。重合性組成物の重合方法は特に限定されないが、架橋性成形体の生産効率を考慮すると、通常、塊状重合が好適である。重合性組成物を塊状重合する方法としては、(i)予備的組成物を任意の部材に注ぐか又は塗布し、予備的組成物中にサイジング剤と予め接触させてなる炭素繊維を含浸させた後、塊状重合する方法、(ii)予備的組成物を、サイジング剤と予め接触させてなる炭素繊維を載置した型内に注ぎこみ、塊状重合する方法、(iii)サイジング剤と予め接触させてなる炭素繊維に予備的組成物を含浸させたものを予め準備し、塊状重合する方法などが挙げられる。
以上のようにして得られる架橋性成形体からなる層の厚さは、通常、15mm以下、好ましくは10mm以下、より好ましくは5mm以下である。
また、通常、重合性組成物は反応に関与しない溶媒等の含有量が少ないので、炭素繊維に含浸させた後に溶媒を除去するなどの工程が不要であり、生産性に優れ、残存溶媒による臭気やフクレ等が、得られる架橋性成形体等で生じにくい。
本発明の架橋性成形体は、例えば、プリプレグとして、本発明の架橋成形体、及び積層体などの架橋成形体複合体の製造に好適に用いられる。
本発明の架橋成形体は、前記架橋性成形体を架橋してなるものである。架橋性成形体の架橋は、本発明の架橋性成形体を構成する架橋性樹脂(シクロオレフィンモノマーの重合体)が架橋反応を起す温度以上に維持することによって行うことができる。加熱温度は、通常、架橋剤により架橋反応が誘起される温度以上である。例えば、架橋剤としてラジカル発生剤を使用する場合、通常、1分間半減期温度以上、好ましくは1分間半減期温度より5℃以上高い温度、より好ましくは1分間半減期温度より10℃以上高い温度である。典型的には、100〜300℃、好ましくは150〜250℃の範囲である。加熱時間は、0.1〜180分間、好ましくは0.5〜120分間、より好ましくは1〜60分間の範囲である。
(1)ボイド
100mm角の積層体1個について表面を目視で観察し、以下の基準で評価した。
○:ボイドが3個以下
×:ボイドが4個以上
(2)含侵性
積層体を2分割し、その断面を研磨し、走査型電子顕微鏡(SEM)で当該断面を観察し、炭素繊維の束の内部に樹脂が含侵しているかについて、以下の基準で評価した。
○:未含侵の部分がない
×:未含侵の部分がある
(3)曲げ強度
JIS K7074に準ずる方法により積層体の曲げ強度の測定を行った。
◎:曲げ強度 550Mpa以上
○:曲げ強度 500Mpa以上、550Mpa未満
△:曲げ強度 400Mpa以上、500Mpa未満
×:曲げ強度 400Mpa未満
(4)耐熱性
積層体から短冊状の試験片(厚さ250μm、幅5mm×長さ45mm)を切り出し、測定用試験片として用いた。試験片を動的粘弾性試験機(型番:EXSTAR DMS6100、セイコーインスツルメント社製)による測定に供してtanδのピーク値からガラス転移温度(Tg)を求めた。Tgが高いほど積層体の耐熱性が高く好ましい。
(5)サイジング剤付着率
炭素繊維のサイジング剤付着率の測定は、JIS R 7601のサイジング剤付着率試験に従って行った。
サイジング剤溶液としては、以下の式:
ポリエチレン製の瓶にシクロオレフィンモノマーとしてジシクロペンタジエン80部及びテトラシクロ[6.2.1.13,6.02,7]ドデカ−4−エン(TCD)20部を入れ、ここに連鎖移動剤としてアリルメタクリレート0.74部、架橋剤としてジ−t−ブチルペルオキシド(1分間半減期温度186℃)1.2部を加え、混合した。次いで前記触媒液をシクロオレフィンモノマー100gあたり0.12mLの割合で加えて撹拌し、予備的組成物を調製した。
サイジング剤として1,2−エポキシ−5−ヘキセンを用いた以外は、実施例1と同様にして積層体を得、評価した。結果を表1に示す。
サイジング剤の付着量を3%にした以外は実施例1と同様にして積層体を得、評価した。結果を表1に示す。
サイジング剤として2−イソシアネートエチルメタクリレート用い、トルエンで希釈し5%溶液を作製した。この溶液を用いた以外は、実施例1と同様にして積層体を得、評価した。結果を表1に示す。また、実施例1と同様にして、樹脂積層板を得、評価したところ、第1の積層体からなる部分とポリプロピレン層との界面にはボイドや亀裂がないことを確認した。
前記市販の炭素繊維織物をそのまま用いた以外は、実施例1と同様にして積層体を得、評価した。結果を表1に示す。なお、サイジング剤はビスフェノールA型エポキシであった。
前記市販の炭素繊維織物から、前記のようにして得られたサイジング剤無しの炭素繊維織物を用いた以外は、実施例1と同様にして積層体を得、評価した。結果を表1に示す。
Claims (7)
- シクロオレフィンモノマー、メタセシス重合触媒、架橋剤、および、末端不飽和基と極性基とを有する化合物を含むサイジング剤と予め接触させてなる炭素繊維を含有してなる重合性組成物。
- シクロオレフィンモノマーが、架橋性の炭素−炭素不飽和結合を1以上有するシクロオレフィンモノマーを含むものである請求項1記載の重合性組成物。
- 連鎖移動剤をさらに含む請求項1または2記載の重合性組成物。
- サイジング剤の末端不飽和基がビニル基および/またはビニリデン基であり、極性基がエポキシ基および/またはイソシアネート基である請求項1〜3いずれか記載の重合性組成物。
- 請求項1〜4いずれかに記載の重合性組成物を重合してなる架橋性成形体。
- 請求項5に記載の架橋性成形体を架橋してなる架橋成形体。
- 請求項6に記載の架橋成形体とその他の部材とを含んでなる架橋成形体複合体。
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JP5640656B2 (ja) * | 2010-10-29 | 2014-12-17 | 日本ゼオン株式会社 | プリプレグ及び積層体 |
US8759463B2 (en) * | 2010-12-17 | 2014-06-24 | Zeon Corporation | Cross-linkable resin shaped article, cross-linked resin shaped article and laminate |
EP2721106B1 (en) | 2011-06-17 | 2020-06-03 | Materia, Inc. | Adhesion promoters and gel-modifiers for olefin metathesis compositions |
US20150152283A1 (en) | 2012-06-12 | 2015-06-04 | Materia, Inc. | Method and composition for improving adhesion of metathesis compositions to substrates |
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US9598531B2 (en) | 2013-02-27 | 2017-03-21 | Materia, Inc. | Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts |
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WO2015106210A1 (en) | 2014-01-10 | 2015-07-16 | Materia, Inc. | Method and composition for improving adhesion of metathesis compositions to substrates |
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