JP2023521924A - 架橋性熱可塑性樹脂組成物およびそれを形成する方法、ならびに硬化した熱可塑性樹脂組成物を形成する方法 - Google Patents
架橋性熱可塑性樹脂組成物およびそれを形成する方法、ならびに硬化した熱可塑性樹脂組成物を形成する方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/247—Heating methods
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/02—Polyamines
Abstract
Description
熱硬化性樹脂(「熱硬化性物質」)および熱可塑性樹脂(「熱可塑性物質」)は、異なる分類のポリマーであり、熱の存在下でのそれらの挙動に基づいて互いに区別される。具体的には、ポリエチレン(PE)、ポリカーボネート(PC)およびポリエーテルエーテルケトン(PEEK)などの熱可塑性物質は、熱を加えると柔軟に、または成形可能になる(冷却すると固化する)一方、エポキシ、ベンゾオキサジンおよびビスマレイミドなどの熱硬化性物質は、硬化すると不可逆的に固まり、加熱しても溶融および再成形することができない。したがって、熱可塑性材料は、それらが流動し始める溶融温度(融点)を有する一方、硬化された熱硬化性製品は、それらの構造的な完全性を失うことなく、より高い温度に耐えることができる。
本要約は、詳細な説明において以下でさらに説明されるコンセプトを選抜したものを紹介するために提供される。本要約は、特許請求される主題の重要な、または本質的な特徴を特定することを意図するものではなく、特許請求される主題の範囲を限定する助けとして使用されることを意図するものでもない。
図1は、1つ以上の実施形態の架橋性熱可塑性樹脂の合成の概略図である。
本開示の1つ以上の実施形態は概して、熱硬化性物質または熱可塑性物質が単独では達成できない特性の組み合わせを提供し得る架橋性熱可塑性樹脂に関する。例えば、架橋性熱可塑性組成物中の架橋性基は、高温での重合によって架橋構造を形成し得る;しかしながら、このような温度未満では、架橋性熱可塑性樹脂の特性が従来の熱可塑性物質の特性を大いに反映し得る(そして、溶融/成形および再溶融/再成形することができる)。架橋後、そのような組成物は、従来の熱硬化性材料の特性(繊維に対する優れた接着性および高温耐性など)を反映する特性を有する。
式中、R1は、水素原子、炭化水素基、置換炭化水素基、および官能基のうち1つ以上を表し得る。1つ以上の実施形態のBZ含有モノマー単位は、R1によって表される1つ以上の置換基を含み得る。本明細書において使用される場合、用語「炭化水素基」は、飽和または不飽和であり得る、分岐、直鎖、および/または環含有炭化水素基を指し得る。炭化水素基は、第一級、第二級、および/または第三級炭化水素であってよい。本明細書において使用される場合、用語「置換炭化水素基」は、少なくとも1つの水素原子が水素ではない基で置き換えられて安定な化合物となった炭化水素基(上記で定義される)を指し得る。そのような置換基は、限定されるものではないが、ハロ、ヒドロキシル、アルコキシ、オキソ、アルカノイル、アリールオキシ、アルカノイルオキシ、アミノ、アルキルアミノ、アリールアミノ、アリールアルキルアミノ、二置換アミン、アルカニルアミノ、アロイルアミノ、アラルカノイルアミノ、置換アルカノイルアミノ、置換アリールアミノ、置換アラルカノイルアミノ、チオール、アルキルチオ、アリールチオ、アリールアルキルチオ、アルキルチオノ、アリールチオノ、アリアルキルチオノ、アルキルスルホニル、アリールスルホニル、アリールアルキルスルホニル、スルホンアミド、置換スルホンアミド、ニトロ、シアノ、カルボキシ、カルバミル、アルコキシカルボニル、アリール、置換アリール、グアニジン、ビニル、アセチレン、アクリレート、シアネート、エポキシド、およびヘテロシクリル基、ならびにそれらの混合物から選択され得る。官能基は、限定されるものではないが、ハロ、ヒドロキシル、アルコキシ、オキソ、アミノ、アミド、チオール、アルキルチオ、スルホニル、アルキルスルホニル、スルホンアミド、置換スルホンアミド、ニトロ、シアノ、カルボキシ、カルバミル、アルコキシカルボニルビニル、アセチレン、アクリレート、シアネート、エポキシド基、およびこれらの混合物から選択され得る。
式中、R1は、式(I)に関して上述した基を表す。R1’は、R1と同じ基であっても異なる基であっていてもよい。R3は、炭化水素基または置換炭化水素基を表してもよい。特定の実施形態において、R3は、ベンゼン、ビベンジル、ジフェニルメタン、ナフタレン、アントラセン、ジフェニルエーテル、ジフェニルスルホンエーテル、ビス(フェノキシ)ベンゼン、スチルベン、フェナントレン、フッ素およびそれらの置換変異体から選択されるがこれらに限定されない芳香族基を表し得る。1つ以上の実施形態において、R3は、約1~100,000Da、または1~10,000Da、または1~1,000Daの範囲内の分子量を有する基を表し得る。1つ以上の実施形態において、1つ以上の開環BZ含有モノマーは、式(II)に関して一緒に使用することができる。
式中、R1は、式(I)に関して上述した基を表す。R1’は、R1と同じ基であっても異なる基であっていてもよい。R4は、炭化水素、エーテル、第二級アミノ、アミド、チオエーテル、スルホニル、スルホンアミド、カルボニル、カルバミル、フルオレニル、アルコキシカルボニル、およびこれらの混合物から選択され得るが、これらに限定されない。1つ以上の実施形態において、R4は、約1~100,000Da、または1~10,000Da、または1~1,000Daの範囲の分子量を有する基を表し得る。1つ以上の実施形態において、式(III)によって表される1つ以上の開環BZ含有モノマーは、組み合わせて使用され得る。1つ以上の実施形態において、式(II)および(III)によって表される1つ以上の開環BZ含有モノマーは、組み合わせて使用され得る。
R5は、特に限定されず、水素原子、炭化水素基、置換炭化水素基、ヒドロキシル基、および官能基のうち1つ以上を表すことができる。1つ以上の実施形態のフェノール含有モノマー単位は、R5で表される1つ以上の置換基を含み得る。例えば、特定の実施形態において、式(IV)で表されるフェノール含有モノマーは、ベンゼンジオール(カテコール、レゾルシノール、もしくはヒドロキノン)、または置換ベンゼンジオール(2-メチルレゾルシノール、2-エチルレゾルシノール、4-メチルカテコールなど、およびこれらのアルキル基がアルコキシ基によって置換されたアルコキシル化誘導体を含む)であってもよい。
式中、R7は、R5に関して上述した基を表す。R7’は、R7と同じ基であっても異なる基であっていてもよい。R6は、炭化水素基または置換炭化水素基を表してもよい。1つ以上の実施形態のビスフェノールモノマーは、2,2’-ビス(4-ヒドロキシフェニル)プロパン(ビスフェノールA)、2,2’-ビス(4-ヒドロキシフェニル)ブタン(ビスフェノールB)、1,1’-ビス(4-ヒドロキシフェニル)エタン(ビスフェノールE)、2,2’-ビス(4-ヒドロキシ-3-イソプロピルフェニル)プロパン(ビスフェノールG)、ビス(4-ヒドロキシフェニル)メタン(ビスフェノールF)、2,2’-ビス(4-ヒドロキシフェニル)ヘキサフルオロプロパン(ビスフェノールAF)、4,4’-(1-フェニルエチリデン)ビスフェノール(ビスフェノールAP)、4,4’-シクロヘキシリデンビスフェノール(ビスフェノールZ)、ビス(4-ヒドロキシフェニル)スルホン(ビスフェノールS)、4,4’-(9-フルオレニリデン)ジフェノール(ビスフェノールFL)、4,4’-(1,3-フェニレンジイソプロピリデン)ビスフェノール(ビスフェノールM)、4,4’-(1,4-フェニレンジイソプロピリデン)ビスフェノール(ビスフェノールP)、およびそれらの置換誘導体からなる群の1つ以上であってもよい。特定の実施形態において、ビスフェノールモノマーは、3,3’-ジメチルビスフェノールA(ビスフェノールC)、3,3’-ジアリルビスフェノールA、および2,2’-ビス(2-ヒドロキシ-5-ビフェニリル)プロパン(ビスフェノールPH)のうち1つ以上であってもよい。1つ以上の実施形態において、式(V)で表される1つ以上のビスフェノール含有モノマーは、組み合わせて使用され得る。1つ以上の実施形態において、式(IV)および(V)で表される1つ以上のフェノール含有モノマーまたはビスフェノール含有モノマーは、組み合わせて使用され得る。
Claims (20)
- ビス-ベンゾオキサジンモノマーと、フェノール官能基、アミン官能基、および/またはチオール官能基を有する二官能性コモノマーとの間の反応から形成されるポリマーを含み、
前記ポリマーは、少なくとも1つの架橋性基を含む、架橋性熱可塑性樹脂組成物。 - 前記架橋性基は、前記ポリマー上のエンドキャップである、請求項1に記載の架橋性熱可塑性樹脂組成物。
- 前記架橋性基は、前記ポリマーの主鎖上にある、請求項1に記載の架橋性熱可塑性樹脂組成物。
- 前記樹脂組成物は、温度140℃における溶融粘度が10000Pa・s以下である、請求項1に記載の架橋性熱可塑性樹脂組成物。
- UVまたはマイクロ波硬化性官能基をさらに含む、請求項1に記載の樹脂組成物。
- 前記UVまたはマイクロ波硬化性官能基は、前記架橋性基である、請求項5に記載の樹脂組成物。
- 前記UVまたはマイクロ波硬化性基は、前記架橋性基と反応する、請求項5に記載の樹脂組成物。
- 含有量が25重量%以下の未反応モノマーを含む、請求項1に記載の樹脂組成物。
- ビス-ベンゾオキサジンモノマーと二官能性コモノマーとを反応させて、少なくとも1つの架橋性基を含むポリマーを形成する工程を含む、架橋性熱可塑性樹脂組成物を形成する方法。
- 前記反応工程は、溶液中でベンゾオキサジン樹脂を形成するために、1気圧下で75℃を超える沸点を有する溶媒中における溶液重合を含む、請求項9に記載の方法。
- 前記溶媒は、酢酸エチル、2-メトキシエタノール、ジメチルホルムアミド(DMF)、N-メチルピロリドン(NMP)、酢酸ブチル、2-メトキシエタノール/テトラヒドロフラン(THF)の混合物、およびこれらの組み合わせからなる群から選択される、請求項10に記載の方法。
- 前記溶液から前記ベンゾオキサジン樹脂を精製することをさらに含む、請求項10に記載の方法。
- 前記ビス-ベンゾオキサジンモノマーと前記二官能性コモノマーとの間のモル比は、1:1~2:1である、請求項10に記載の方法。
- 前記反応工程は、前記ビス-ベンゾオキサジンモノマーとビスフェノールコモノマーとの溶融重合を含む、請求項9に記載の方法。
- 前記ビス-ベンゾオキサジンモノマーと前記ビスフェノールコモノマーとの間のモル比は、1:10~10:1である、請求項14に記載の方法。
- 前記熱可塑性樹脂組成物を、UVまたはマイクロ波硬化性官能基を含むように改質することをさらに含む、請求項9に記載の方法。
- 請求項9に記載の方法によって製造された、樹脂組成物。
- 硬化した熱可塑性樹脂組成物を形成する方法であって:
請求項1に記載の架橋性熱可塑性樹脂組成物を提供する工程と;
前記架橋性熱可塑性樹脂組成物を、外部刺激を加えることによって硬化させて、前記硬化した熱可塑性樹脂を形成する工程とを含む、方法。 - 前記外部刺激は、熱、紫外線照射、マイクロ波照射、および水分からなる群から選択される、請求項18に記載の方法。
- 前記架橋性熱可塑性樹脂組成物は、UVまたはマイクロ波硬化性官能基をさらに含み、前記外部刺激は、紫外線照射またはマイクロ波照射を含む、請求項18に記載の方法。
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