JP2017226774A - 硬化性組成物及び繊維強化複合材料 - Google Patents
硬化性組成物及び繊維強化複合材料 Download PDFInfo
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- JP2017226774A JP2017226774A JP2016124576A JP2016124576A JP2017226774A JP 2017226774 A JP2017226774 A JP 2017226774A JP 2016124576 A JP2016124576 A JP 2016124576A JP 2016124576 A JP2016124576 A JP 2016124576A JP 2017226774 A JP2017226774 A JP 2017226774A
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- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 239000000463 material Substances 0.000 title claims abstract description 40
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- 125000001931 aliphatic group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 20
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- 239000003795 chemical substances by application Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004695 Polyether sulfone Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
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- 238000007334 copolymerization reaction Methods 0.000 description 3
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- 150000004692 metal hydroxides Chemical class 0.000 description 3
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- 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
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
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- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 150000001639 boron compounds Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 150000004650 carbonic acid diesters Chemical class 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
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- 125000003700 epoxy group Chemical group 0.000 description 2
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- 238000011156 evaluation Methods 0.000 description 2
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
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Abstract
Description
で表されるエポキシ化合物(A1)を必須の成分として含有することを特徴とする硬化性組成物を提供するものである。
で表されるエポキシ化合物(A1)を必須の成分として含有することを特徴とする。
で表される構造部位等が挙げられる。
で表されるものが挙げられる。
本発明の硬化性組成物は、難燃性を発揮させるために、実質的にハロゲン原子を含有しない非ハロゲン系難燃剤を含有していてもよい。
本発明の硬化性組成物は、充填材を含有していてもよい。本発明の硬化性組成物が充填材を含有すると、得られる硬化物において優れた機械特性を発現させることができるようになる。
本発明の硬化性組成物は、添加剤を含有していてもよい。本発明の硬化性組成物が添加剤を含有すると、得られる硬化物において剛性や寸法安定性等、他の特性が向上する。添加剤としては、例えば可塑剤、酸化防止剤、紫外線吸収剤、光安定剤等の安定剤、帯電防止剤、導電性付与剤、応力緩和剤、離型剤、結晶化促進剤、加水分解抑制剤、潤滑剤、衝撃付与剤、摺動性改良剤、相溶化剤、核剤、強化剤、補強剤、流動調整剤、染料、増感材、着色用顔料、ゴム質重合体、増粘剤、沈降防止剤、タレ防止剤、消泡剤、カップリング剤、防錆剤、抗菌・防カビ剤、防汚剤、導電性高分子等を添加することも可能である。
本発明の硬化性組成物は、フィラメントワインディング法にて繊維強化樹脂成形品を製造する場合などには、有機溶剤を含有していてもよい。ここで使用し得る有機溶剤としては、メチルエチルケトンアセトン、ジメチルホルムアミド、メチルイソブチルケトン、メトキシプロパノール、シクロヘキサノン、メチルセロソルブ、エチルジグリコールアセテート、プロピレングリコールモノメチルエーテルアセテート等が挙げられ、その選択や適正な使用量は用途によって適宜選択し得る。
本発明の硬化性組成物から硬化物を得る方法としては、一般的なエポキシ樹脂組成物の硬化方法に準拠すればよく、例えば加熱温度条件は、組み合わせる硬化剤の種類や用途等によって、適宜選択すればよい。例えば、硬化性組成物を、室温〜250℃程度の温度範囲で加熱する方法が挙げられる。成形方法なども硬化性組成物の一般的な方法が用いること可能であり、特に本発明の硬化性組成物に特有の条件は不要である。
本発明の繊維強化複合材料とは、硬化性組成物を強化繊維に含浸させた後の硬化前の状態の材料のことである。ここで、強化繊維は、有撚糸、解撚糸、又は無撚糸などいずれでも良いが、解撚糸や無撚糸が、繊維強化複合材料において優れた成形性を有することから、好ましい。さらに、強化繊維の形態は、繊維方向が一方向に引き揃えたものや、織物が使用できる。織物では、平織り、朱子織りなどから、使用する部位や用途に応じて自由に選択することができる。具体的には、機械的強度や耐久性に優れることから、炭素繊維、ガラス繊維、アラミド繊維、ボロン繊維、アルミナ繊維、炭化ケイ素繊維などが挙げられ、これらの2種以上を併用することもできる。これらの中でもとりわけ成形品の強度が良好なものとなる点から炭素繊維が好ましく、かかる、炭素繊維は、ポリアクリロニトリル系、ピッチ系、レーヨン系などの各種のものが使用できる。
本発明の繊維強化樹脂成形品とは、強化繊維と硬化性組成物の硬化物とを有する成形品であり、繊維強化複合材料を熱硬化させて得られるものである。本発明の繊維強化樹脂成形品として、具体的には、繊維強化成形品における強化繊維の体積含有率が40%〜85%の範囲であることが好ましく、強度の観点から50%〜70%の範囲であることが特に好ましい。そのような繊維強化樹脂成形品としては、例えば、フロントサブフレーム、リアサブフレーム、フロントピラー、センターピラー、サイドメンバー、クロスメンバー、サイドシル、ルーフレール、プロペラシャフトなどの自動車部品、電線ケーブルのコア部材、海底油田用のパイプ材、印刷機用ロール・パイプ材、ロボットフォーク材、航空機の一次構造材、二次構造材などを挙げることができる。
下記表1に示す配合に従って各成分を配合し、均一に撹拌混合して、硬化性組成物を得た。該硬化性組成物について、下記の要領で各種評価試験を行った。結果を表1に示す。
・A1−1:下記構造式(1−1)で表されるエポキシ化合物(Cardlite社製「NC−513」)
・A2−2:ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 840S」エポキシ当量184g/eq)
・B−2:4−メチルヘキサヒドロフタル酸とヘキサフタル酸とを70/30で含有する組成物(新日本理化株式会社製「リカシッド MH−700」)
・B’−1:2−エチル−4−メチルイミダゾール
粘度計(TOKI SANGYO CO.LTD.VISCOMETER TV−22)を用い、先で得た硬化性組成物の粘度を25℃、50rmp条件下で測定した。
先で得た硬化性組成物を、幅90mm、長さ110mm、高さ4mmの型枠内に流し込み、100℃で2時間硬化後、更に165℃で3時間硬化させた。得られた硬化物をダイヤモンドカッターで幅5mm、長さ50mmに切り出し、これを試験片とした。次に、粘弾性測定装置(エスアイアイ・ナノテクノロジー社製「DMS6100」)を用いて試験片の両持ち曲げによる動的粘弾性を測定し、tanδが最大となる値の温度をガラス転移温度(Tg)として評価した。なお、動的粘弾性測定の測定条件は、温度条件 室温〜260℃、昇温速度3℃/分、周波数1Hz、歪振幅10μmとした。
・A:ガラス転移温度(Tg)が120℃以上
・B:ガラス転移温度(Tg)が70℃以上120℃未満
・C:ガラス転移温度(Tg)が70℃未満
先で得た硬化性組成物を幅90mm、長さ110mm、高さ4mmの型枠内に流し込み、100℃で2時間硬化後、更に165℃で3時間硬化させた。JIS K6911に準拠して、硬化物の曲げ強度及び曲げ弾性率を測定した。それぞれ以下の通り評価した。
曲げ強度
・A:110MPa以上
・B:100MPa以上110MPa未満
・C:100MPa未満
曲げ弾性率
・A:2800MPa以上
・B:2500MPa以上2800MPa未満
・C:2500MPa未満
先で得た硬化性組成物を幅90mm、長さ110mm、高さ4mmの型枠内に流し込み、100℃で2時間硬化後、更に165℃で3時間硬化させた。得られた硬化物の質量を測定した後、40℃に加温した蒸留水に浸漬し、90日間放置して吸水させた。吸水処理後の硬化物の質量を測定し、下記計算式にて硬化物の吸水率を算出した。
(吸水率)=[{(吸水処理後の硬化物の質量)−(吸水処理前の硬化物の質量)}/(吸水処理前の硬化物の質量)]×100
先で得た硬化性組成物を30℃で保持し、初期粘度の2倍となる時間をポットライフとして評価した。
Claims (10)
- 前記エポキシ樹脂成分(A)が、前記エポキシ化合物(A1)に加え、脂肪族エポキシ樹脂を含有する請求項1記載の硬化性組成物。
- 前記エポキシ樹脂成分(A)が、前記エポキシ化合物(A1)に加え、ビスフェノール型エポキシ樹脂を含有する請求項1記載の硬化性組成物。
- 前記エポキシ樹脂成分(A)の0.1〜20質量%が前記エポキシ化合物(A1)である請求項1記載の硬化性組成物。
- 請求項1〜4の何れか1項記載の硬化性組成物の硬化物。
- 請求項1〜4の何れか1項記載の硬化性組成物と、強化繊維とを必須成分とする繊維強化複合材料。
- 前記強化繊維の体積含有率が40%〜85%の範囲内である請求項6記載の繊維強化複合材料。
- 請求項5記載の硬化物と強化繊維とを必須成分とする繊維強化樹脂成形品。
- 前記強化繊維の体積含有率が40%〜85%の範囲内である請求項8記載の繊維強化樹脂成形品。
- 請求項6又は7記載の繊維強化複合材料を熱硬化させる繊維強化樹脂成形品の製造方法。
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