JP6670045B2 - オキサゾリドン環含有エポキシ樹脂、その製造方法、エポキシ樹脂組成物及び硬化物 - Google Patents
オキサゾリドン環含有エポキシ樹脂、その製造方法、エポキシ樹脂組成物及び硬化物 Download PDFInfo
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- JP6670045B2 JP6670045B2 JP2015050298A JP2015050298A JP6670045B2 JP 6670045 B2 JP6670045 B2 JP 6670045B2 JP 2015050298 A JP2015050298 A JP 2015050298A JP 2015050298 A JP2015050298 A JP 2015050298A JP 6670045 B2 JP6670045 B2 JP 6670045B2
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- epoxy resin
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- resin
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- 239000003795 chemical substances by application Substances 0.000 claims description 25
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- 239000003085 diluting agent Substances 0.000 description 6
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- 229910052739 hydrogen Inorganic materials 0.000 description 6
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 6
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- 238000004382 potting Methods 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000003566 sealing material Substances 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical class [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical class [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
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- 239000013008 thixotropic agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
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- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
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Description
東ソー株式会社製GPC測定装置、HLC−8220GPCを使用した。東ソー株式会社製カラム、TSKgelG4000HXL、TSKgelG3000HXL、及びTSKgelG2000HXLを直列に備えたものを使用し、カラム温度は40℃にした。また、溶離液にはテトラヒドロフラン(THF)を用い、1mL/分の流速とし、検出器はRI(示差屈折計)検出器を用いた。データ処理は、東ソー株式会社製GPC−8020モデルIIバージョン4.10を使用した。測定試料はサンプル0.1gを10mLのTHFに溶解し、マイクロフィルターでろ過したものを100μL使用した。得られたクロマトグラムにより二核体含有率及び三核体含有率を算出し、標準の単分散ポリスチレン(東ソー株式会社製、A−500、A−1000、A−2500、A−5000、F−1、F−2、F−4、F−10、F−20、F−40、F−80、F−128)で求めた検量線により数平均分子量を測定した。
本発明のオキサゾリドン環含有エポキシ樹脂に用いるエポキシ樹脂(a)は、好ましくはフェノール類とアルデヒド類等の架橋剤を酸性触媒の存在下に縮合して得られる下記式(2)で表される多官能のノボラック樹脂と、エピハロヒドリンとを反応して得られ、式(1)で表される特定の分子量分布を有する多官能のノボラック型エポキシ樹脂である。
ガラス転移温度(TMA法):IPC−TM−650 2.4.24.1に準じて熱機械分析装置(株式会社日立ハイテクサイエンス製、EXSTAR6000 TMA/SS120U)にて10℃/分の昇温条件で測定を行った時のTMA外挿値の温度で表した。
ガラス製セパラブルフラスコに、フェノールを2500部、シュウ酸二水和物を7.5部仕込み、窒素ガスを注入しながら撹拌を行い、加熱を行って昇温した。次に、80℃にて撹拌しながら、37.4%ホルマリン474.1部を30分かけて滴下し反応させた。さらに反応温度を92℃に保ち3時間反応を行った。昇温を行い、反応生成水を系外に除去しながら110℃まで昇温した。残存フェノールを160℃にて減圧下回収を行い、さらに温度を250℃に上げて二核体の一部を回収し、フェノールノボラック樹脂を得た。得られたフェノールノボラック樹脂の二核体含有率及び三核体含有率はGPCによる測定でそれぞれ10面積%及び38面積%であった。
合成例1と同様な装置に、合成例1で得られたフェノールノボラック樹脂を666部、エピクロロヒドリンを2110部、イオン交換水を17部仕込み、撹拌しながら50℃まで昇温した。均一に溶解後、49%水酸化ナトリウム水溶液を14.2部仕込み3時間反応を行った。次に、64℃まで昇温した後、水の還流が起きる程度まで減圧を引き、49%水酸化ナトリウム水溶液457.7部を3時間かけて滴下し、この滴下中に還流留出した水とエピクロルヒドリンを分離槽で分離しエピクロルヒドリンは反応容器に戻し、水は系外に除いて反応した。反応終了後、温度を70℃まで上げ脱水を行い、温度を135℃として残存するエピクロロヒドリンを回収した。常圧に戻し、メチルイソブチルケトン(MIBK)を1232部加えて溶解した。イオン交換水を1200部加え、撹拌静置して副生した食塩を水に溶解して除去した。次に49%水酸化ナトリウム水溶液を37.4部仕込み、80℃で90分間撹拌反応して精製反応を行った。MIBKを追加、水洗を数回行いイオン性不純物を除去した。溶剤を回収し、フェノールノボラック型エポキシ樹脂を得た。得られたフェノールノボラック型エポキシ樹脂の二核体含有率10面積%、三核体含有率35面積%、三核体及び四核体含有率の合計が52面積%、五核体以上含有率38面積%、数平均分子量635、重量平均分子量884、分散度1.39、エポキシ当量174g/eq.であった。
GPC測定チャートを図1に示す。図中、Aで示すピークが二核体を示し、Bで示すピークが三核体を示し、Cで示すピーク群が五核体以上を示す。横軸に溶出時間を示し、左縦軸に信号強度を示し、右縦軸に数平均分子量Mを常用対数(log)で示す。用いた標準物質の数平均分子量の測定値を黒丸でプロットしており検量線とした。
合成例1と同様な装置に、合成例2で得られたフェノールノボラック型エポキシ樹脂を90部、ビスフェノールF型液状エポキシ樹脂(新日鉄住金化学株式会社製、エポトートYDF−1500、エポキシ当量168g/eq.、粘度2500mPa・s)を10部仕込み、50℃まで撹拌しながら昇温し、均一に溶解して、混合型のエポキシ樹脂とした。得られた混合型のエポキシ樹脂について分子量分布を測定したところ、二核体含有率18面積%、三核体含有率32面積%、三核体及び四核体含有率の合計が48面積%、五核体以上含有率34面積%、数平均分子量597、重量平均分子量824、分散度1.38、エポキシ当量173g/eq.であった。
エポキシ樹脂A:合成例2で得られたフェノールノボラック型エポキシ樹脂
エポキシ樹脂B:合成例3で得られた混合型のエポキシ樹脂
エポキシ樹脂C:汎用型フェノールノボラック型エポキシ樹脂(新日鉄住金化学株式会社製、エポトートYDPN−638、二核体含有率22面積%、三核体含有率15面積%、三核体及び四核体含有率の合計が25面積%、五核体以上含有率53面積%、数平均分子量528、重量平均分子量1127、分散度2.13、エポキシ当量176g/eq.GPC測定チャートを図2に示す。A、B及びCは図1の説明と同じである。)
エポキシ樹脂D:ビスフェノールA型液状エポキシ樹脂(新日鉄住金化学株式会社製、エポトートYD−8125、エポキシ当量174g/eq.、粘度4100mPa・s)
エポキシ樹脂E:オルソクレゾールノボラック型エポキシ樹脂(新日鉄住金化学株式会社製、エポトートYDCN−703、エポキシ当量202g/eq.、軟化点℃)
エポキシ樹脂F:リン含有エポキシ樹脂(新日鉄住金化学株式会社製、エポトートTX−1320A、エポキシ当量763g/eq.、リン含有量5.0%)
イソシアネートA:ジフェニルメタンジイソシアネート(三井化学株式会社製、コスモネートPH、NCO濃度34%)
イソシアネートB:ポリメチレンポリフェニルポリイソシアネート(三井化学株式会社製、コスモネートM−50、NCO濃度34%)
イソシアネートC:2,4−トリレンジイソシアネート(80%)と2,6−トリレンジイソシアネート(20%)の混合物(三井化学株式会社製、コスモネートT−80、NCO濃度48%)
イソシアネートD:シクロヘキサン−1,3−ジイルビスメチレンジイソシアナート(三井化学株式会社製、タケネート600、NCO濃度43%)
触媒A:テトラメチルアンモニウムヨージド(東京化成工業株式会社製、試薬)
触媒B:n−ブチルトリフェニルホスホニウム・ブロミド(日本化学工業株式会社製、ヒシコーリン(登録商標)BTPPBr)
PN:フェノールノボラック樹脂(昭和電工株式会社製、ショウノールBRG−557、軟化点80℃)
DICY:ジシアンジアミド(日本カーバイト株式会社製)
2E4MZ:2−エチル−4−メチルイミダゾール(四国化成工業株式会社製、キュアゾール(登録商標)2E4MZ)
PX−200:芳香族縮合リン酸エステル(大八化学工業株式会社製、PX−200、リン含有量9.0%)
合成例1と同様な装置に、エポキシ樹脂(a)としてエポキシ樹脂Aを100部、触媒Aを0.17部仕込み、窒素ガスを投入しながら昇温し、120℃にて30分間温度を維持して系内の水分を除去した。次に、130℃〜140℃の温度を維持しながら、イソシアネート化合物(b)としてイソシアネートA14.4部(イソシアネート基b/エポキシ基aの当量比[(b)/(a)]=0.20)を50%トルエン溶液として、3時間かけて滴下した。滴下終了後、同温度を維持しながら、さらに60分間撹拌を続けた。反応終了後、150℃、1.33kPa、30分の回収条件で溶剤を除去して、オキサゾリドン環含有エポキシ樹脂(樹脂1)を得た。得られた樹脂1について、エポキシ当量、軟化点を測定した。測定結果を表1に示す。また、図3にGPCチャートを、図4にIRチャートをそれぞれ示す。
表1に示す各原料の仕込量(部)に従い、実施例1と同様の装置を使用し、同様の操作で、オキサゾリドン環含有エポキシ樹脂を合成した。実施例1と同様に得られた樹脂のエポキシ当量、軟化点を測定し、測定結果を表1に示す。また、実施例2、実施例4、実施例6及び実施例7のイソシアネートの滴下時間は、滴下速度を実施例1とほぼ同じにするため、3時間から6時間に変更した。これらの実施例2〜7で得られたオキサゾリドン環含有エポキシ樹脂を樹脂2〜7とした。
表2に示す各原料の仕込量(部)に従い、実施例1と同様の装置を使用し、同様の操作で、オキサゾリドン環含有エポキシ樹脂を合成した。実施例1と同様に得られた比較樹脂のエポキシ当量、軟化点を測定し、測定結果を表2に示す。なお、比較例4のイソシアネートの滴下時間は、滴下速度を実施例1とほぼ同じにするため、3時間から6時間に変更した。また、比較例1、比較例6及び比較例7は、滴下時間途中でゲル化が起こり反応を中止した。これらの比較例で得られたオキサゾリドン環含有エポキシ樹脂を比較樹脂2〜5とした。
実施例1で得られた樹脂1を100部、硬化剤としてPNを41.0部、硬化促進剤として2E4MZを0.01部で配合し、MEK、プロピレングリコールモノメチルエーテル、N,N−ジメチルホルムアミドで調整した混合溶剤に溶解してエポキシ樹脂組成物ワニスを得た。
実施例1〜実施例7で得られた樹脂1〜樹脂7、PN、DICY、及び2E4MZを表3の配合量(部)で配合し、実施例8と同様の装置を使用して、同様の操作を行い、積層板及び試験片を得た。実施例8と同様の試験を行い、その結果を表3に示す。なお、表中の「−」は不使用を表す。
比較例2〜比較例5で得られた比較樹脂2〜比較樹脂5、エポキシ樹脂E、PN、DICY、及び2E4MZを表4の配合量(部)で配合し、実施例8と同様の装置を使用して、同様の操作を行い、積層板及び試験片を得た。実施例8と同様の試験を行い、その結果を表4に示す。なお、表中の「−」は不使用を表す。
樹脂1、樹脂2、比較樹脂2、比較樹脂3、エポキシ樹脂F、PN、2E4MZ、及びPX−200を表5の処方の配合量(部)で配合し、実施例8と同様の装置を使用して、同様の操作で、積層板及び試験片を得た。実施例8と同様の試験を行い、その結果を表5に示す。また、難燃性測定用試験片は積層板の両面をエッチングして得た。なお、表中の「−」は不使用を表す。
Claims (14)
- エポキシ樹脂(a)とイソシアネート化合物(b)より得られるオキサゾリドン環含有エポキシ樹脂であって、該エポキシ樹脂(a)がゲルパーミエーションクロマトグラフィーにおける測定において二核体含有率が20面積%以下であり、三核体含有率が15面積%以上60面積%以下であり、三核体と四核体の含有率の合計が15面積%以上85面積%以下であり、五核体以上の含有率は45面積%以下であり、数平均分子量が350以上700以下である分子量分布を持つノボラック型エポキシ樹脂であることを特徴とするオキサゾリドン環含有エポキシ樹脂。
- ノボラック型エポキシ樹脂が下記式(1)で表されるエポキシ樹脂である請求項1に記載のオキサゾリドン環含有エポキシ樹脂。
- イソシアネート化合物(b)が、分子内に平均で1.8個以上のイソシアネート基を有する請求項1又は2に記載のオキサゾリドン環含有エポキシ樹脂。
- エポキシ樹脂(a)のエポキシ基1モルに対して、イソシアネート化合物(b)のイソシアネート基を0.02モル以上0.6モル以下の範囲で反応させて得られる請求項1〜3のいずれか1項に記載のオキサゾリドン環含有エポキシ樹脂。
- エポキシ当量が200〜500g/eq.である請求項1〜4のいずれか1項に記載のオキサゾリドン環含有エポキシ樹脂。
- 軟化点が50〜150℃である請求項1〜5のいずれか1項に記載のオキサゾリドン環含有エポキシ樹脂。
- 請求項1に記載のオキサゾリドン環含有エポキシ樹脂の製造方法であって、エポキシ樹脂(a)とイソシアネート化合物(b)を反応させること、該エポキシ樹脂(a)がゲルパーミエーションクロマトグラフィーにおける測定において二核体含有率が20面積%以下であり、三核体含有率が15面積%以上60面積%以下であり、三核体と四核体の含有率の合計が15面積%以上85面積%以下であり、五核体以上の含有率は45面積%以下であり、数平均分子量が350以上700以下である分子量分布を持つノボラック型エポキシ樹脂であり、エポキシ樹脂(a)のエポキシ基1モルに対し、イソシアネート化合物(b)のイソシアネート基を0.02モル以上0.6モル以下の範囲で使用することを特徴とするオキサゾリドン環含有エポキシ樹脂の製造方法。
- ノボラック型エポキシ樹脂が下記式(1)で表されるエポキシ樹脂である請求項7に記載のオキサゾリドン環含有エポキシ樹脂の製造方法。
- イソシアネート化合物(b)が、分子内に平均で1.8個以上のイソシアネート基を有する請求項7又は8に記載のオキサゾリドン環含有エポキシ樹脂の製造方法。
- 請求項1〜6のいずれか1項に記載のオキサゾリドン環含有エポキシ樹脂と硬化剤とを必須成分とし、全エポキシ樹脂のエポキシ基1モルに対して、該硬化剤の活性水素基を0.2モル以上1.5モル以下の範囲で配合することを特徴とするエポキシ樹脂組成物。
- 請求項10に記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物。
- 請求項10に記載のエポキシ樹脂組成物を用いたことを特徴とするプリプレグ。
- 請求項10に記載のエポキシ樹脂組成物を用いたことを特徴とする積層板。
- 請求項10に記載のエポキシ樹脂組成物を用いて得られたことを特徴とするプリント配線基板。
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