JP6742304B2 - 粒子状ポリ(フェニレンエーテル)含有ワニス組成物、複合材、それから調製したラミネート、および複合材の製造方法 - Google Patents
粒子状ポリ(フェニレンエーテル)含有ワニス組成物、複合材、それから調製したラミネート、および複合材の製造方法 Download PDFInfo
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- JP6742304B2 JP6742304B2 JP2017519868A JP2017519868A JP6742304B2 JP 6742304 B2 JP6742304 B2 JP 6742304B2 JP 2017519868 A JP2017519868 A JP 2017519868A JP 2017519868 A JP2017519868 A JP 2017519868A JP 6742304 B2 JP6742304 B2 JP 6742304B2
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- C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08J2471/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08J2471/12—Polyphenylene oxides
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Description
組成物の合計質量に対して、アセトン、メチルエチルケトンおよびこれらの組み合わせからなる群より選択されるケトンを30〜70質量%と;硬化性成分を15〜60質量%と;平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を5〜40質量%と;硬化性成分のための有効量の硬化剤とを含む硬化性組成物で、補強構造物を少なくとも一部コーティングして、硬化性組成物でコーティングされた補強構造物を形成するステップと;硬化性組成物でコーティングされた補強構造物からケトンの少なくとも一部を除去して、複合材を形成するステップと、を備える複合材の形成方法である。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%と
を含む複合材である。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%と
を含むラミネートである。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%と、
を含む複合材である。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%とを含む。「複数のプリプレグをラミネートする」との関連で、「複数」とは、少なくとも2つを意味する。ラミネートを形成するのに使用したプリプレグの数は、例えば3〜12であり得る。ラミネートのプロセスがプリプレグの一部硬化した組成物をさらに硬化するステップを含むことも理解されるだろう。例えば、ラミネートは、30分〜5時間、150〜200℃の温度で、10〜100MPaの圧力で実施できる。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%とを含む複合材。
平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を10〜60質量%と、
シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびそれらの組み合わせからなる群より選択される硬化性成分と、硬化性成分のための有効量の硬化剤とを少なくとも一部硬化した生成物を40〜90質量%とを含むラミネート。
アセトンまたはメチルエチルケトン(MEK)と溶媒として使用するワニスを、表2に示す実施例1〜16の組成物に従って、粒子状ポリ(フェニレンエーテル(pPPE)および様々な種類の熱硬化性樹脂を用いて調製した。最初に熱硬化性樹脂を溶媒に溶解させることによって、ワニスを調製した。粒子状PPEはアセトンまたはMEKに可溶ではなく、それ故に、粒子状PPEをワニス溶液中に懸濁させた。ワニス溶液の合計樹脂含量は、50質量%(wt.%)で一定に保った。均一な分散が得られたら、実施例1〜16のそれぞれについて、Brookfield粘度計を用いて、初期粘度を求めた。2日後、各溶液について粘度を再び求めた。一部の例では、7日後に3回目の粘度を決定した。
E−ガラス布をワニス溶液中に浸すことで、プリプレグを調製した。ワニス組成物を表4に要約する。リストした成分に加えて、各組成物は、硬化性成分100質量部に対して1質量部の2−エチル−4−メチルイミダゾールを含んでいた。空気循環オーブン中で、140℃で3〜5分間プリプレグを加熱して、溶媒(MEKまたはMIBK)を除去し、硬化性材料を一部硬化した。比較実施例5および本発明の実施例17および18のそれぞれにおいて、メチルエチルケトンを溶媒として使用し、BPAエポキシを硬化性材料として使用した。E−ガラス布の初期質量を測定し、ワニスで処理し、溶媒を蒸発させた後のプリプレグ(すなわちB段階のプリプレグ)の質量と比較した。プリプレグ組成物を、表4に示した比較実施例5および本発明の実施例17および18に要約する。実施例はそれぞれ、同じワニスから同じ加工条件の下で調製した8個のプリプレグ試料を含む。各実施例での樹脂の質量%およびガラスの質量%は、8個のプリプレグの平均であった。「質量%樹脂」は、硬化性材料とpPPE成分とを含み、硬化性材料とpPPEとガラスとの合計質量に対するものである。樹脂およびガラスの同じ量を含有するようにプリプレグを調製した。例えば、ワニスから調製しpPPEを有さないプリプレグの平均樹脂含量は45.06質量%(比較実施例5)であり、ワニスから調製しpPPEを有するプリプレグでは44.47〜46.28質量%であった(実施例17および18)。
8個の一部硬化した(B段階の)プリプレグを積層し、200℃で2時間、31MPa(4500psi)の圧力で、プレスして硬化することによって、ラミネートを調製した。ラミネートの組成物および特性を表5に要約する。記入した成分に加えて、組成物はそれぞれ、硬化性成分100質量部に対して1質量部の2−エチル−4−メチルイミダゾールを含んだ。
Claims (14)
- 組成物の合計質量に対して、
アセトン、メチルエチルケトン、メチルイソブチルケトンおよびこれらの組み合わせからなる群より選択されるケトンを30〜70質量%と;
硬化性成分を15〜60質量%と;
クロロホルム中25℃で測定した固有粘度が0.3〜0.6dL/gであり、平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を5〜40質量%と、を含むことを特徴とする組成物。 - 25〜30℃の範囲の温度で測定した粘度が0.01〜0.25Pa・s(10〜250cP)である請求項1に記載の組成物。
- 前記ケトンがメチルエチルケトンを含む請求項1に記載の組成物。
- 前記硬化性成分が、シアン酸エステル樹脂、トリアリルシアヌレート、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、多官能性エポキシ化合物、不飽和エステルイミド樹脂、硬化性シリコーン樹脂およびこれらの組み合わせからなる群より選択される請求項1に記載の組成物。
- 前記硬化性成分が、シアン酸エステル樹脂、トリアリルイソシアヌレート、ポリブタジエン、二官能性エポキシ化合物、クレゾールノボラックエポキシ化合物およびこれらの組み合わせからなる群より選択される請求項1に記載の組成物。
- 前記粒子状ポリ(フェニレンエーテル)がポリ(2,6−ジメチル−1,4−フェニレンエーテル)を含む請求項1乃至5のいずれか1項に記載の組成物。
- 硬化性成分のための有効量の硬化剤をさらに含む請求項1乃至5のいずれか1項に記載の組成物。
- 前記ケトンがメチルエチルケトンを含み;
前記硬化性成分が、二官能性エポキシ化合物、多官能性エポキシ化合物およびこれらの組み合わせからなる群より選択され;
前記粒子状ポリ(フェニレンエーテル)の平均粒径が4〜10μmであり、かつ粒径の相対標準偏差が30〜50%であり;
前記粒子状ポリ(フェニレンエーテル)が、クロロホルム中25℃で測定した固有粘度が0.3〜0.6dL/gであるポリ(2,6−ジメチル−1,4−フェニレンエーテル)を含み;
前記組成物が、
前記ケトンを40〜60質量%と、
前記硬化性成分を25〜50質量%と、
前記粒子状ポリ(フェニレンエーテル)を5〜30質量%と、を含む請求項1に記載の組成物。 - 複合材の形成方法であって、
硬化性組成物の合計質量に対して、
アセトン、メチルエチルケトンおよびこれらの組み合わせからなる群より選択されるケトンを30〜70質量%と;
硬化性成分を15〜60質量%と;
クロロホルム中25℃で測定した固有粘度が0.3〜0.6dL/gであるポリ(2,6−ジメチル−1,4−フェニレンエーテル)を含み、平均粒径が3〜12μmであり、かつ粒径の相対標準偏差が20〜60%である粒子状ポリ(フェニレンエーテル)を5〜40質量%と;
硬化性成分のための有効量の硬化剤と
を含む硬化性組成物で補強構造物を少なくとも一部コーティングして、硬化性組成物でコーティングされた補強構造物を形成するステップと;
硬化性組成物でコーティングされた前記補強構造物からケトンの少なくとも一部を除去して複合材を形成するステップと、
を備えることを特徴とする複合材の形成方法。 - 前記補強構造物が、ガラス繊維、炭素繊維、芳香族ポリアミド繊維およびこれらの組み合わせからなる群より選択される繊維を含む強化織物を含む請求項9に記載の複合材の形成方法。
- 前記補強構造物がガラス布を含む請求項9に記載の複合材の方法。
- 前記複合材を少なくとも一部硬化してプリプレグ形成するステップをさらに備える請求項9乃至11のいずれか1項に記載の複合材の形成方法。
- 前記補強構造物がガラス布を含み;
前記ケトンがメチルエチルケトンを含み;
前記硬化性成分が、二官能性エポキシ化合物、多官能性エポキシ化合物およびこれらの組み合わせからなる群より選択され;
前記粒子状ポリ(フェニレンエーテル)の平均粒径が4〜10μmであり、かつ粒径の相対標準偏差が30〜50%であり;
前記粒子状ポリ(フェニレンエーテル)が、クロロホルム中25℃で測定した固有粘度が0.3〜0.6dL/gであるポリ(2,6−ジメチル−1,4−フェニレンエーテル)を含み;
前記硬化性組成物が、
前記ケトンを40〜60質量%と、
前記硬化性成分を25〜50質量%と、
前記粒子状ポリ(フェニレンエーテル)を5〜30質量%と、を含む請求項9に記載の複合材の形成方法。 - 請求項1に記載の組成物から形成される複合材であって、
補強構造物と;
前記補強構造物を少なくとも一部コーティングする少なくとも一部硬化した樹脂と;を含み、
前記少なくとも一部硬化した樹脂は、請求項1に記載の組成物から形成されることを特徴とする複合材。
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US201462081610P | 2014-11-19 | 2014-11-19 | |
US62/081,610 | 2014-11-19 | ||
PCT/US2015/051831 WO2016081063A1 (en) | 2014-11-19 | 2015-09-24 | Particulate poly(phenylene ether)-containing varnish composition, composite and laminate prepared therefrom, and method of forming composite |
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JP2017534723A JP2017534723A (ja) | 2017-11-24 |
JP6742304B2 true JP6742304B2 (ja) | 2020-08-19 |
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US (1) | US10647877B2 (ja) |
EP (1) | EP3221402A4 (ja) |
JP (1) | JP6742304B2 (ja) |
KR (1) | KR20170087456A (ja) |
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JPS56106954A (en) * | 1980-01-29 | 1981-08-25 | Mitsubishi Petrochem Co Ltd | Stabilized polyphenylene ether resin composition |
US5087657A (en) | 1989-02-23 | 1992-02-11 | Amoco Corporation | Fiber-reinforced composites toughened with resin particles |
US5834565A (en) * | 1996-11-12 | 1998-11-10 | General Electric Company | Curable polyphenylene ether-thermosetting resin composition and process |
US6352782B2 (en) | 1999-12-01 | 2002-03-05 | General Electric Company | Poly(phenylene ether)-polyvinyl thermosetting resin |
US6906120B1 (en) * | 2000-06-20 | 2005-06-14 | General Electric | Poly(arylene ether) adhesive compositions |
US7022777B2 (en) * | 2001-06-28 | 2006-04-04 | General Electric | Moldable poly(arylene ether) thermosetting compositions, methods, and articles |
JP2004059596A (ja) * | 2002-07-24 | 2004-02-26 | Mitsubishi Chemicals Corp | 樹脂組成物及びそれを用いたプリント配線板 |
SG157958A1 (en) * | 2003-05-22 | 2010-01-29 | Asahi Kasei Chemicals Corp | Epoxy resin composition |
JP2008050526A (ja) * | 2006-08-28 | 2008-03-06 | Matsushita Electric Works Ltd | 樹脂組成物、それを用いたプリプレグ及び積層板 |
US7655278B2 (en) * | 2007-01-30 | 2010-02-02 | Sabic Innovative Plastics Ip B.V. | Composite-forming method, composites formed thereby, and printed circuit boards incorporating them |
US8017697B2 (en) | 2008-06-24 | 2011-09-13 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether)-polysiloxane composition and method |
US8669332B2 (en) | 2011-06-27 | 2014-03-11 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether)-polysiloxane composition and method |
WO2013141255A1 (ja) | 2012-03-19 | 2013-09-26 | 旭化成イーマテリアルズ株式会社 | ポリフェニレンエーテル粒子を含むプリプレグ |
US9611385B2 (en) * | 2012-06-29 | 2017-04-04 | Sabic Global Technologies B.V. | Ultrafine poly(phenylene ether) particles and compositions derived therefrom |
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- 2015-09-24 WO PCT/US2015/051831 patent/WO2016081063A1/en active Application Filing
- 2015-09-24 CN CN201580058898.0A patent/CN107109048A/zh active Pending
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EP3221402A1 (en) | 2017-09-27 |
JP2017534723A (ja) | 2017-11-24 |
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US20170247566A1 (en) | 2017-08-31 |
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