JP2023539665A - マレイミド変性の活性エステル及びその調製方法と使用 - Google Patents
マレイミド変性の活性エステル及びその調製方法と使用 Download PDFInfo
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- JP2023539665A JP2023539665A JP2023514068A JP2023514068A JP2023539665A JP 2023539665 A JP2023539665 A JP 2023539665A JP 2023514068 A JP2023514068 A JP 2023514068A JP 2023514068 A JP2023514068 A JP 2023514068A JP 2023539665 A JP2023539665 A JP 2023539665A
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- active ester
- maleimide
- substituted
- compound
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- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 29
- -1 diphenol compound Chemical class 0.000 claims abstract description 28
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
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- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 5
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical group CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 4
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- 239000000758 substrate Substances 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052582 BN Inorganic materials 0.000 description 1
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Classifications
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Abstract
Description
から選ばれる。
(1)構造同定:フーリエ赤外分光装置(FT‐IR)により実施例1~5に提供されたマレイミド変性の活性エステルについて赤外テスト同定を行う。
例示的に、実施例1で提供されたマレイミド変性の活性エステルK―1の赤外分光グラフは図1に示すとおりであり、図1から分かるように、前記マレイミド変性の活性エステルK―1は、波数1740cm-1で活性エステルのエステル基固有の吸収ピークが表れ、波数1717.2cm-1、722.2cm-1がイミド環固有のピークであり、1606.8cm-1がC=Cの伸縮振動吸収ピークであるが、3400cm-1付近でフェノール性水酸基の強い吸収ピークが表れず、これはフェノール性水酸基がエステル基化になったことを説明している。
例示的に、実施例1で提供されたマレイミド変性の活性エステルK―1の高機能性ポリマークロマトグラフィーグラフ(APC図)は図2に示すとおりであり、図2から分かるように、前記マレイミド変性の活性エステルK―1の重量平均分子量Mwは2745である。
適用例1~5、比較例3~6に提供された熱硬化性樹脂組成とそれを含む回路基板について性能テストを行う。方法は以下の通りである。
Claims (10)
- マレイミド変性の活性エステルであって、前記活性エステルの調製原料は式A1で表される構造を有するジフェノール類化合物、式A2で表される構造を有するジアシル基化合物及び式A3で表される構造を有するマレイミド基含有化合物を含むことを特徴とするマレイミド変性の活性エステル。
- 前記Arは、
から選ばれ、
Ar2は、
Ar3は、
R3、R4はそれぞれ独立して、フッ素、C1~C5直鎖又は分岐鎖アルキル基、C2~C5直鎖又は分岐鎖オレフィン基、
R5はC1~C5直鎖又は分岐鎖アルキレン基であり、
n1、n3はそれぞれ独立して、0~4の整数から選ばれ、
n2は0~6の整数から選ばれ、
Y1、Y2はそれぞれ独立して、―O―、―S―、カルボニル基、スルホン基、置換又は非置換のC1~C20直鎖又は分岐鎖アルキレン基、置換又は非置換のC3~C30シクロアルキレン基、置換又は非置換のC6~C30アラルキレン基から選ばれ;前記置換する置換基はそれぞれ独立して、フッ素、C1~C5直鎖又は分岐鎖アルキル基、C6~C18アリール基から選ばれ、
mは0~10から選ばれ、
好ましくは、前記Y1、Y2はそれぞれ独立して、―O―、―S―、C1~C5直鎖又は分岐鎖アルキレン基、
好ましくは、前記Xは置換又は非置換のフェニレン基、置換又は非置換のビフェニレン基、置換又は非置換のナフチレン基、置換又は非置換のビフェニレンエーテル基から選ばれ;前記置換する置換基はそれぞれ独立して、フッ素、C1~C5直鎖又は分岐鎖アルキル基から選ばれ、
好ましくは、前記X1は塩素、臭素、ヨウ素又は水酸基から選ばれ、
好ましくは、前記Ar1は置換又は非置換のフェニレン基、置換又は非置換のナフチレン基から選ばれ;前記置換する置換基はフッ素、C1~C5直鎖又は分岐鎖アルキル基から選ばれ、
好ましくは、前記R1、R2がいずれも水素である、ことを特徴とする請求項1に記載の活性エステル。 - 前記ジアシル基化合物とジフェノール類化合物とのモル比は1:(0.5~0.9)、好ましくは1:(0.5~0.8)であり、
好ましくは、前記ジアシル基化合物とマレイミド基含有化合物とのモル比は1:(0.2~1)、さらに好ましくは1:(0.4~1)である、ことを特徴とする請求項1又は2に記載の活性エステル。 - 請求項1~3のいずれか1項に記載の活性エステルの調製方法であって、式A1で表される構造を有するジフェノール類化合物、式A2で表される構造を有するジアシル基化合物及び式A3で表される構造を有するマレイミド基含有化合物を反応させ、前記活性エステルが得られることを含む、ことを特徴とする活性エステルの調製方法。
- 前記反応の温度は-10~60℃であり、
好ましくは、前記反応は塩基性触媒の存在で行い、
好ましくは、前記反応の保護ガス雰囲気で行い、
好ましくは、前記反応は溶媒の存在で行い、
好ましくは、前記反応は完了後、さらに生成物をポスト処理することを含む、ことを特徴とする請求項4に記載の調製方法。 - エポキシ樹脂と請求項1~3のいずれか1項に記載の活性エステルを含み、
好ましくは、さらに、他の硬化剤、難燃剤、無機フィラー、有機フィラー又は硬化促進剤の任意の1種又は少なくとも2種の組み合わせを含む、ことを特徴とする熱硬化性樹脂組成物。 - 半導体封止材料の原料は請求項6に記載の熱硬化性樹脂組成物を含む、ことを特徴とする半導体封止材料。
- 基材、及び浸漬・乾燥で前記基材に付着する請求項6に記載の熱硬化性樹脂組成物を含み、
好ましくは、前記基材はガラス繊維布、不織布又はクォーツクロスの任意の1種又は少なくとも2種の組み合わせを含む、ことを特徴とするプリプレグ。 - 少なくとも1枚の請求項8に記載のプリプレグ、及び前記プリプレグの一側又は両側に設置される金属箔を含む、ことを特徴とする回路基板。
- 基材フィルム又は金属箔、及び前記基材フィルム又は金属箔の少なくとも1つの表面にコートされる請求項6に記載の熱硬化性樹脂組成物を含む、ことを特徴とする積層フィルム。
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