JP6841221B2 - 繊維強化ポリアミド樹脂基材、その製造方法、それを含む成形品および複合成形品 - Google Patents
繊維強化ポリアミド樹脂基材、その製造方法、それを含む成形品および複合成形品 Download PDFInfo
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- JP6841221B2 JP6841221B2 JP2017517126A JP2017517126A JP6841221B2 JP 6841221 B2 JP6841221 B2 JP 6841221B2 JP 2017517126 A JP2017517126 A JP 2017517126A JP 2017517126 A JP2017517126 A JP 2017517126A JP 6841221 B2 JP6841221 B2 JP 6841221B2
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- Prior art keywords
- polyamide resin
- terminal
- fiber
- general formula
- base material
- Prior art date
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- 238000000034 method Methods 0.000 claims description 60
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 4
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 4
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- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 3
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Description
連続した強化繊維に、または不連続の強化繊維が分散した強化繊維基材にポリアミド樹脂を含浸させてなる繊維強化ポリアミド樹脂基材であって、前記ポリアミド樹脂が、ポリアミド樹脂を構成するポリマーの少なくとも一部が、ポリマーの主鎖を構成する繰り返し構造単位とは異なる構造単位から構成される構造をポリマーの末端基に有する末端変性ポリアミド樹脂であり、前記末端変性ポリアミド樹脂が、下記一般式(I)で表される末端構造を1〜20質量%含有する繊維強化ポリアミド樹脂基材、である。
−X−(R 1 −O) m −R 2 (I)
上記一般式(I)中、mは2〜100の範囲を表す。R 1 は炭素数2〜10の2価の炭化水素基、R 2 は炭素数1〜30の1価の炭化水素基を表す。−X−は−NH−、−N(CH 3 )−または−(C=O)−を表す。一般式(I)中に含まれるm個のR 1 は同じでも異なってもよい。
アミノ酸、ラクタム、ならびに/もしくは、ジアミンおよびジカルボン酸を重合する際に、下記一般式(III)で表される末端変性用化合物をアミノ酸、ラクタム、ジアミンおよびジカルボン酸の合計に対して1〜20質量%含有させて、ポリアミド樹脂の末端に末端変性用化合物を結合させることにより、下記一般式(I)で表される末端構造を1〜20質量%含有する末端変性ポリアミド樹脂を得る工程と、連続した強化繊維に、または不連続繊維の強化繊維が分散した強化繊維基材に前記末端変性ポリアミド樹脂を含浸させる工程を少なくとも有する上記繊維強化ポリアミド樹脂基材の製造方法、である。
−X−(R1−O)m−R2 (I)
上記一般式(III)および(I)中、mは2〜100の範囲を表す。R1は炭素数2〜10の2価の炭化水素基、R2は炭素数1〜30の1価の炭化水素基を表す。上記一般式が(III)の場合、−X−は−NH−、−N(CH3)−または−O(C=O)−を表す。上記一般式が(I)の場合、−X−は−NH−、−N(CH3)−または−(C=O)−を表す。一般式(III)中に含まれるm個のR1は同じでも異なってもよい。
上記繊維強化ポリアミド樹脂基材を含む成形品、である。
上記繊維強化ポリアミド樹脂基材と、熱可塑性樹脂を含む成形品とが、少なくとも一部で接合された複合成形品、である。
上記一般式(II)中、R3は炭素数1〜30の1価の炭化水素基を表す。前記一般式(I)におけるXが−NH−または−N(CH3)−の場合、上記一般式(II)における−Y−は−(C=O)−を表し、前記一般式(I)におけるXが−(C=O)−の場合、上記一般式(II)におけるYは−NH−または−N(CH3)−を表す。
(Li:測定した繊維長(i=1,2,3,・・・400)(単位:mm))。
上記一般式(I)中、mは2〜100(2以上100以下)の範囲を表す。mが大きいほど、溶融粘度の低減効果が効果的に奏される。mは5以上が好ましく、8以上がより好ましく、16以上がさらに好ましい。一方、mが小さいほど、耐熱性をより高く維持することができる。mは70以下が好ましく、50以下がより好ましい。なお、ポリアミド樹脂の主たる構造単位に由来する特性を維持する観点から、本発明における末端変性ポリアミド樹脂は、上記一般式(I)で表される構造をポリマーの末端のみに有することが好ましい。
上記一般式(II)中、R3は炭素数1〜30(1以上30以下)の1価の炭化水素基を表す。R3の炭素数が少ないほどポリアミド樹脂の主たる構造単位との親和性に優れるため、炭素数1〜30の炭化水素基であることが好ましい。具体的には、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、イコシル基、エイコシル基、ヘンイコシル基、ヘネイコシル基、ドコシル基、トリコシル基、テトラコシル基、ペンタコシル基、ヘキサコシル基、ヘプタコシル基、オクタコシル基、ノナコシル基、トリアコンチル等の直鎖アルキル基、イソプロピル基、イソブチル基、tert−ブチル基、イソペンチル基、ネオペンチル基等の分岐鎖アルキル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基等のシクロアルキル基、フェニル基、トリル基等のアリール基、ベンジル基、2−フェニルエチル基等のアラルキル基などが挙げられる。末端変性ポリアミド樹脂の熱安定性および着色防止の観点から、R3は1価の炭素数1以上20以下の飽和炭化水素基またはアリール基であることがさらに好ましい態様である。
(1)ポリアミド樹脂、末端変性用化合物、および必要に応じてその他の成分を、ポリアミド樹脂の融点以上において溶融混練し、反応せしめる方法や、これらを溶液中において混合し、反応せしめた後に溶媒を除く方法、および(2)ポリアミド樹脂の主たる構造単位を構成する原料(ポリアミド樹脂の主たる原料)、末端変性用化合物、および必要に応じてその他の成分を添加して反応させる方法(反応時添加方法)などが挙げられる。
上記一般式(V)において、Aは炭素原子数1〜12のアルキレン基または炭素数6〜24のアリーレン基を表す。aは炭素原子と水素原子以外の原子または単結合を表す。rは(a−A)で表される構造単位の繰り返し数を表し、1以上である。Wは、水酸基、アルデヒド基、カルボキシル基、スルホ基、アミノ基、グリシジル基、イソシアネート基、カルボジイミド基、オキサゾリン基、オキサジン基、エステル基、アミド基、シラノール基またはシリルエーテル基を表す。
上記一般式(III)中、nは2〜100の範囲を表す。前記一般式(I)におけるmと同様に、5以上が好ましく、8以上がより好ましく、16以上がさらに好ましい。一方、nは70以下が好ましく、50以下がより好ましい。R1は炭素数2〜10の2価の炭化水素基、R2は炭素数1〜30の1価の炭化水素基を表す。それぞれ、一般式(I)におけるR1およびR2として例示したものが挙げられる。X−は−NH−、−N(CH3)−または−O(C=O)−を示す。ポリアミドの末端との反応性に優れる−NH−がより好ましい。
上記一般式(IV)中、R3は炭素数1〜30の1価の炭化水素基を表す。前記一般式(II)と同様に、末端変性ポリアミド樹脂の熱安定性および着色防止の観点から、R3は1価の飽和炭化水素基がさらに好ましい。前記一般式(III)におけるXが−NH−または−N(CH3)−の場合、上記一般式(IV)における−Y−は−O(C=O)−を表し、前記一般式(III)におけるXが−O(C=O)−の場合、上記一般式(IV)におけるYは−NH−または−N(CH3)−を表す。
(1)ポリアミド樹脂と末端変性用化合物とを溶融混練することにより末端変性ポリアミド樹脂を製造する場合には、溶融混練温度をポリアミド樹脂の融点(Tm)よりも10℃以上40℃以下高い温度で反応させることが好ましい。例えば、押出機を用いて溶融混練する場合、押出機のシリンダー温度を前記範囲とすることが好ましい。溶融混練温度をこの範囲にすることで、末端変性用化合物の揮発、ポリアミド樹脂の分解を抑制しつつ、ポリアミド樹脂の末端と末端変性用化合物とを効率的に結合させることができる。ポリアミド樹脂としては、前述のポリアミド樹脂が例示される。
(2)ポリアミド樹脂の原料と末端変性用化合物とを重合時に反応させる方法により末端変性ポリアミド樹脂を製造する場合には、ポリアミド樹脂の融点以上で反応させる溶融重合法、ポリアミド樹脂の融点未満で反応させる固相重合法のいずれを用いてもよい。ポリアミド樹脂を与える原料としては、前述のアミノ酸、ラクタムおよび「ジアミンとジカルボン酸との混合物」が例示される。
ρf:強化繊維の密度(g/cm3)
ρr:末端変性ポリアミド樹脂の密度(g/cm3)
また、本発明の実施形態の繊維強化ポリアミド樹脂基材は、その用法や目的に応じて、所望の含浸性を選択することができる。例えば、より含浸性を高めたプリプレグや、半含浸のセミプレグ、含浸性の低いファブリックなどが挙げられる。一般的に、含浸性の高い成形材料ほど、短時間の成形で力学特性に優れる成形品が得られるため好ましい。
本発明の第二の態様における、不連続繊維が分散した強化繊維基材に末端変性ポリアミド樹脂を含浸させる方法としては、例えば、末端変性ポリアミド樹脂を押出機により供給して強化繊維基材に含浸させる方法、粉末の末端変性ポリアミド樹脂を強化繊維基材の繊維層に分散し溶融させる方法、末端変性ポリアミド樹脂をフィルム化して強化繊維基材とラミネートする方法、末端変性ポリアミド樹脂を溶剤に溶かし溶液の状態で強化繊維基材に含浸させた後に溶剤を揮発させる方法、末端変性ポリアミド樹脂を繊維化して不連続繊維との混合糸にする方法、末端変性ポリアミド樹脂の前駆体を強化繊維基材に含浸させた後に重合させて末端変性ポリアミド樹脂にする方法、メルトブロー不織布を用いてラミネートする方法などが挙げられる。いずれの方法を用いてもよいが、末端変性ポリアミド樹脂を押出機により供給して強化繊維基材に含浸させる方法は、末端変性ポリアミド樹脂を加工する必要がないという利点があり、粉末の末端変性ポリアミド樹脂を強化繊維基材の繊維層に分散し溶融させる方法は、含浸がしやすいという利点があり、末端変性ポリアミド樹脂をフィルム化して強化繊維基材とラミネートする方法は、比較的品質の良いものが得られるという利点がある。
各実施例および比較例により得られた繊維強化ポリアミド樹脂基材の質量W0を測定したのち、該繊維強化ポリアミド樹脂基材を空気中500℃で30分間加熱してポリアミド樹脂成分を焼き飛ばし、残った強化繊維の質量W1を測定し、下記式(VI)により繊維強化ポリアミド樹脂基材の体積含有率(Vf)を算出した。
ρf:強化繊維の密度(g/cm3)
ρr:末端変性ポリアミド樹脂の密度(g/cm3)
[相対粘度(ηr)]
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂の、樹脂濃度0.01g/mLの98%硫酸溶液について、25℃でオストワルド式粘度計を用いて相対粘度を測定した。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂2.5mgを、ヘキサフルオロイソプロパノール(0.005N−トリフルオロ酢酸ナトリウム添加)4mlに溶解し、得られた溶液を0.45μmのフィルターでろ過した。得られた溶液を用いて、GPC測定により数平均分子量(Mn)および重量平均分子量(Mw)(溶融滞留前重量平均分子量)を測定した。測定条件を以下に示す。
検出器:示差屈折率計 Waters 2414(Waters製)
カラム:Shodex HFIP−806M(2本)+HFIP−LG
溶媒:ヘキサフルオロイソプロパノール(0.005N−トリフルオロ酢酸ナトリウム添加)
流速:1mL/min
試料注入量:0.1mL
温度:30℃
分子量基準物質:ポリメチルメタクリレート。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂0.5gを精秤し、フェノール/エタノール混合溶液(比率:83.5/16.5質量比)25mLを加えて室温で溶解した後、チモールブルーを指示薬として、0.02規定の塩酸で滴定してアミノ末端基量(mol/t)を求めた。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂0.5gを精秤し、ベンジルアルコール20mLを加えて195℃の温度で溶解した後、フェノールフタレインを指示薬として、0.02規定の水酸化カリウムのエタノール溶液を用いて、195℃の状態で滴定してカルボキシル末端基量(mol/t)を求めた。
実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂について、日本電子(株)製FT−NMR:JNM−AL400を用いて1H−NMR測定を実施した。まず、測定溶媒として重水素化硫酸を用いて、試料濃度50mg/mLの溶液を調製した。積算回数256回にて、ポリアミド樹脂の1H−NMR測定を実施した。一般式(I)で表される末端構造におけるR1およびR2由来部分のピーク、一般式(II)で表される末端構造におけるR3部分由来のピークおよびポリアミド樹脂骨格の繰り返し構造単位由来のピークを同定した。各ピークの積分強度を算出し、算出した積分強度と、それぞれの構造単位中の水素原子数とから、末端変性ポリアミド樹脂における一般式(I)で表される末端構造の含有量[I](mol/t、質量%)(滞留前含有量)および一般式(II)で表される末端構造の含有量[II](mol/t、質量%)をそれぞれ算出した。
TAインスツルメント社製示差走査熱量計(DSC Q20)を用いて、各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂5〜7mgを秤量し、窒素雰囲気下、20℃から昇温速度20℃/minで250℃まで昇温した。昇温したときに現れる吸熱ピークの頂点をTm(融点)とした。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。溶融粘度の測定装置として、キャピラリーフローメーター((株)東洋精機製作所製、キャピログラフ1C型)を用いて、径0.5mm、長さ5mmのオリフィスにて、融点+60℃、せん断速度9,728sec−1の条件で溶融粘度(滞留前溶融粘度)を測定した。ただし、末端変性ポリアミド樹脂またはポリアミド樹脂を溶融させるため、5分間滞留させた後に測定を行った。この溶融粘度の値が小さいほど、高い流動性を有することを示す。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。キャピラリーフローメーター((株)東洋精機製作所製、キャピログラフ1C型)を用いて、径0.5mm、長さ5mmのオリフィスにて、融点+60℃で60分間溶融滞留後、せん断速度9,728sec−1の条件で溶融粘度(滞留後溶融粘度)を測定した。前述の方法により測定した溶融粘度(滞留前溶融粘度)と溶融粘度(滞留後溶融粘度)から、(滞留後溶融粘度/滞留前溶融粘度)×100により溶融粘度保持率[%]を算出した。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。キャピラリーフローメーター((株)東洋精機製作所製、キャピログラフ1C型)を用いて、径0.5mm、長さ5mmのオリフィスにて、融点+60℃で60分間溶融滞留を行った。溶融滞留後の末端変性ポリアミド樹脂またはポリアミド樹脂について、前述の分子量測定方法と同様のGPC測定により重量平均分子量(Mw)(滞留後重量平均分子量)を測定した。前述の方法により測定した重量平均分子量(溶融滞留前重量平均分子量)と重量平均分子量(滞留後重量平均分子量)から、(滞留後重量平均分子量/滞留前重量平均分子量)×100により重量平均分子量保持率[%]を算出した。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。キャピラリーフローメーター((株)東洋精機製作所製、キャピログラフ1C型)を用いて、径0.5mm、長さ5mmのオリフィスにて、融点+60℃で60分間溶融滞留を行った。溶融滞留後の末端変性ポリアミド樹脂またはポリアミド樹脂について、前述の末端構造含有量測定方法と同様の1H−NMR測定により末端変性ポリアミド樹脂における一般式(I)で表される末端構造の含有量[I](mol/t)(滞留後含有量)を算出した。前述の方法により測定した一般式(I)で表される末端構造の含有量[I](mol/t)(滞留前含有量)と一般式(I)で表される末端構造の含有量[I](mol/t)(滞留後含有量)から、(滞留後含有量/滞留前含有量)×100により含有量保持率を算出した。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。任意部分を20mg切り出し、熱重量分析装置(パーキンエルマー社製、TGA7)を用い、窒素ガス雰囲気下、末端変性ポリアミド樹脂またはポリアミド樹脂の融点+60℃の温度で40分間保持し、熱処理前後の重量減少率[%]を測定した。
各実施例および比較例により得られた末端変性ポリアミド樹脂またはポリアミド樹脂を、80℃真空乾燥器中で12時間以上乾燥した。東芝機械(株)製IS55EPN射出成形機を用いて、シリンダー温度は、末端変性ポリアミド樹脂またはポリアミド樹脂の融点(Tm)+60℃とし、金型温度は80℃とし、射出時間と保圧時間は合わせて10秒、冷却時間は10秒の成形サイクル条件で、試験片厚み1/25インチ(約1.0mm)のASTM4号ダンベルの評価用試験片を射出成形した。得られたASTM4号ダンベル型試験片を、“テンシロン”(登録商標)UTA−2.5T(オリエンテック社製)に供し、ASTM−D638に準じて、23℃、湿度50%の雰囲気下で、歪み速度10mm/minで引張試験を行い、引張破断伸度を測定した。
各実施例および比較例により得られた繊維強化ポリアミド樹脂基材の厚み方向断面を以下のように観察した。繊維強化末端変性ポリアミド樹脂をエポキシ樹脂で包埋したサンプルを用意し、繊維強化末端変性ポリアミド樹脂の厚み方向断面が良好に観察できるようになるまで、前記サンプルを研磨した。研磨したサンプルを、超深度カラー3D形状測定顕微鏡VHX−9500(コントローラー部)/VHZ−100R(測定部)((株)キーエンス製)を使用して、拡大倍率400倍で撮影した。撮影範囲は、繊維強化末端変性ポリアミド樹脂の厚み×幅500μmの範囲とした。撮影画像において、樹脂が占める部位の面積および空隙(ボイド)となっている部位の面積を求め、次式により含浸率を算出した。
含浸性および熱安定性が高い場合はボイドが低減され、含浸性または熱安定性の少なくとも一方が低い場合はボイドが増加することから、繊維強化ポリアミド樹脂基材の含浸性および熱安定性は、この含浸率を判断基準とし、以下の2段階で評価し、良を合格とした。第一の態様における繊維強化ポリアミド樹脂基材は、融点+30℃、60℃、100℃の加工温度にて製造した。第二の態様における繊維強化ポリアミド樹脂基材は、融点+10℃、20℃、30℃の加工温度にて製造した。
良:含浸率が98%以上である。
各実施例および比較例により得られた繊維強化末端変性ポリアミド樹脂または繊維強化ポリアミド樹脂基材の表面品位を目視により観察した。表面品位は、以下の2段階で評価し、良を合格とした。
不良:表面にわれ、マトリックス樹脂の変色、強化繊維の露出有り
第一の態様における繊維強化ポリアミド樹脂基材は、融点+30℃、60℃、100℃の加工温度にて製造した。第二の態様における繊維強化ポリアミド樹脂基材は、融点+10℃、20℃、30℃の加工温度にて製造した。
実施例および比較例において、原料は以下に示すものを用いた。
炭素繊維束:東レ(株)製 T700S−12K
・ε−カプロラクタム:和光純薬工業(株)製、和光特級。
・下記の構造式(化学式1)で表されるメトキシポリ(エチレングリコール)ポリ(プロピレングリコール)アミン:HUNTSMAN製“JEFFAMINE”(登録商標)M1000(数平均分子量Mn1,000)。
・安息香酸:和光純薬工業(株)製、試薬特級
・酢酸:和光純薬工業(株)製、試薬特級
・ステアリン酸:和光純薬工業(株)製、試薬特級
・セロチン酸:東京化成工業(株)製。
[実施例1]
ε−カプロラクタム20g、イオン交換水20g、“JEFFAMINE”M1000を1.6g、安息香酸0.14gを反応容器に仕込み密閉し、窒素置換した。反応容器外周にあるヒーターの設定温度を290℃とし、加熱を開始した。缶内圧力が1.0MPaに到達した後、水分を系外へ放出させながら缶内圧力1.0MPaに保持し、缶内温度が240℃になるまで昇温した。缶内温度が240℃に到達した後、ヒーターの設定温度を270℃に変更し、1時間かけて常圧となるよう缶内圧力を調節した(常圧到達時の缶内温度:243℃)。続けて、缶内に窒素を流しながら(窒素フロー)240分間保持して末端変性ポリアミド6樹脂を得た(最高到達温度:253℃)。続いて得られた末端変性ポリアミド6樹脂を、イオン交換水でソックスレー抽出を行い、未反応の末端変性用化合物を除去した。このようにして得られた末端変性ポリアミド6樹脂の相対粘度は1.81、重量平均分子量は3.0万、融点(Tm)は220℃、溶融粘度は5.5Pa・sであった。また、得られた末端変性ポリアミド6樹脂は以下の化学式4にて示される構造と以下の化学式5で示される構造を末端に有する末端変性ポリアミド6樹脂を含むものであった。その他の物性を表1に示す。
[実施例2〜39、比較例1〜3]
原料を表1〜5に示す組成に変更し、かつ缶内圧力を常圧とした後、缶内に窒素を流しながら保持する時間(窒素フロー時間)を表1〜5に示す時間に変更したこと以外は実施例1と同様にして末端変性ポリアミド6樹脂を得た。実施例1により得られた末端変性ポリアミド6樹脂にかえて、各実施例および比較例により得られた末端変性ポリアミド6樹脂またはポリアミド6樹脂を用いたこと以外は実施例1と同様にして繊維強化ポリアミド樹脂基材を得た。得られた末端変性ポリアミド6樹脂の物性および、繊維強化ポリアミド樹脂基材の物性を表1〜5に示す。
[実施例40]
ヘキサメチレンジアミン9.46g、アジピン酸11.92g、イオン交換水20g、“JEFFAMINE”(登録商標)M1000を1.6g、安息香酸0.14gを反応容器に仕込み密閉し、窒素置換した。反応容器外周にあるヒーターの設定温度を290℃とし、加熱を開始した。缶内圧力が1.75MPaに到達した後、水分を系外へ放出させながら缶内圧力1.75MPaに保持し、缶内温度が260℃になるまで昇温した。缶内温度が260℃に到達した後、ヒーターの設定温度を290℃に変更し、1時間かけて常圧となるよう缶内圧力を調節した(常圧到達時の缶内温度:270℃)。続けて、缶内に窒素を流しながら(窒素フロー)240分間保持して末端変性ポリアミド66樹脂を得た(最高到達温度:275℃)。ここで、得られたポリアミド樹脂は実施例1で示す構造を末端に有する末端変性ポリアミド66樹脂を含むものであった。
加工温度を320℃とした以外は実施例1と同様にして、得られた末端変性ポリアミド66樹脂を用いて繊維強化ポリアミド66樹脂基材を得た。得られた末端変性ポリアミド66樹脂の物性および繊維強化ポリアミド66樹脂基材の物性を表6に示す。
[実施例41]
ヘキサメチレンジアミン7.74g、セバシン酸13.46g、イオン交換水20g、“JEFFAMINE”(登録商標)M1000を1.6g、安息香酸0.14gを反応容器に仕込み密閉し、窒素置換した。反応容器外周にあるヒーターの設定温度を290℃とし、加熱を開始した。缶内圧力が1.0MPaに到達した後、水分を系外へ放出させながら缶内圧力1.0MPaに保持し、缶内温度が240℃になるまで昇温した。缶内温度が240℃に到達した後、ヒーターの設定温度を290℃に変更し、1時間かけて常圧となるよう缶内圧力を調節した(常圧到達時の缶内温度:243℃)。続けて、缶内に窒素を流しながら(窒素フロー)240分間保持して末端変性ポリアミド610樹脂を得た(最高到達温度:253℃)。ここで、得られたポリアミド樹脂は以下の実施例1で示す構造を末端に有する末端変性ポリアミド610樹脂を含むものであった。
[実施例42]
実施例1と同様にして末端変性ポリアミド樹脂を得た。得られた末端変性ポリアミド樹脂を押出機に投入し、溶融混練した後フィルムダイから膜状に押出し、樹脂フィルムを得た。
[実施例43〜80、比較例4〜6]
原料を表7〜11に示す組成に変更し、かつ缶内圧力を常圧とした後、缶内に窒素を流しながら保持する時間(窒素フロー時間)を表7〜11に示す時間に変更したこと以外は実施例40と同様にして末端変性ポリアミド6樹脂を得た。実施例42により得られた末端変性ポリアミド6樹脂にかえて、各実施例および比較例により得られた末端変性ポリアミド6樹脂またはポリアミド6樹脂を用いたこと以外は実施例42と同様にして繊維強化ポリアミド樹脂基材を得た。得られた末端変性ポリアミド6樹脂の物性および、繊維強化ポリアミド樹脂基材の物性を表7〜11に示す。
[実施例81]
実施例40と同様にして末端変性ポリアミド66樹脂を得た。加工温度を290℃とした以外は実施例42と同様にして、得られた末端変性ポリアミド610樹脂を用いて繊維強化ポリアミド610樹脂基材を得た。得られた末端変性ポリアミド610樹脂の物性および繊維強化ポリアミド610樹脂基材の物性を表12に示す。
[実施例82]
実施例41と同様にして末端変性ポリアミド610樹脂を得た。加工温度を250℃とした以外は実施例42と同様にして、得られた末端変性ポリアミド610樹脂を用いて繊維強化ポリアミド610樹脂基材を得た。得られた末端変性ポリアミド610樹脂の物性および繊維強化ポリアミド610樹脂基材の物性を表12に示す。
Claims (16)
- 連続した強化繊維に、または不連続の強化繊維が分散した強化繊維基材にポリアミド樹脂を含浸させてなる繊維強化ポリアミド樹脂基材であって、前記ポリアミド樹脂が、ポリアミド樹脂を構成するポリマーの少なくとも一部が、ポリマーの主鎖を構成する繰り返し構造単位とは異なる構造単位から構成される構造をポリマーの末端基に有する末端変性ポリアミド樹脂であり、前記末端変性ポリアミド樹脂が、下記一般式(I)で表される末端構造を1〜20質量%含有する繊維強化ポリアミド樹脂基材。
−X−(R 1 −O) m −R 2 (I)
上記一般式(I)中、mは2〜100の範囲を表す。R 1 は炭素数2〜10の2価の炭化水素基、R 2 は炭素数1〜30の1価の炭化水素基を表す。−X−は−NH−、−N(CH 3 )−または−(C=O)−を表す。一般式(I)中に含まれるm個のR 1 は同じでも異なってもよい。 - 前記末端変性ポリアミド樹脂が、さらに下記一般式(II)で表される末端構造を0.1〜5質量%含有する請求項1に記載の繊維強化ポリアミド樹脂基材。
−Y−R3 (II)
上記一般式(II)中、R3は炭素数1〜30の1価の炭化水素基を表す。前記一般式(I)におけるXが−NH−または−N(CH3)−の場合、上記一般式(II)における−Y−は−(C=O)−を表し、前記一般式(I)におけるXが−(C=O)−の場合、上記一般式(II)におけるYは−NH−または−N(CH3)−を表す。 - 前記強化繊維が一方向に連続して配列している、または、数平均繊維長が3〜100mmの不連続繊維である請求項1または2に記載の繊維強化ポリアミド樹脂基材。
- 前記強化繊維が炭素繊維を含み、強化繊維を20〜70体積%含有する請求項1〜3のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂が、前記一般式(I)で表される末端構造と前記一般式(II)で表される末端構造を合計60〜250[mol/t]含有し、かつ前記一般式(I)で表される末端構造の含有量[mol/t]と前記一般式(II)で表される末端構造の含有量[mol/t]の比((I)/(II))が0.3〜2.5である請求項1〜4のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂が、アミノ末端基とカルボキシル末端基を合計50〜150[mol/t]含有し、かつアミノ末端基の含有量[mol/t]とカルボキシル末端基の含有量[mol/t]の比(アミノ末端基/カルボキシル末端基)が0.5〜2.5である請求項1〜5のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、樹脂濃度0.01g/mLの98%硫酸溶液の25℃における相対粘度(ηr)が1.3〜3.0である請求項1〜6のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、ゲルパーミエーションクロマトグラフィーにより測定した重量平均分子量Mwが15,000〜50,000である請求項1〜7のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、融点+60℃、せん断速度9,728sec−1の条件における溶融粘度が30Pa・s以下である請求項1〜8のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、融点+60℃の条件下60分間滞留前後における前記一般式(I)で表される末端構造の含有量保持率((滞留後含有量/滞留前含有量)×100)が80%以上である請求項1〜9のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、融点+60℃の条件下60分間滞留前後における重量平均分子量保持率((滞留後重量平均分子量/滞留前重量平均分子量)×100)が80%〜120%である請求項1〜10のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、融点+60℃の条件下60分間滞留前後における溶融粘度保持率((滞留後溶融粘度/滞留前溶融粘度)×100)が80%〜120%である請求項1〜11のいずれかに記載の繊維強化ポリアミド樹脂基材。
- 前記末端変性ポリアミド樹脂の、窒素雰囲気下、融点+60℃の条件下40分間滞留前後における重量減少率が4%以下である請求項1〜12のいずれかに記載の繊維強化ポリアミド樹脂基材。
- アミノ酸、ラクタム、ならびに/もしくは、ジアミンおよびジカルボン酸を重合する際に、下記一般式(III)で表される末端変性用化合物をアミノ酸、ラクタム、ジアミンおよびジカルボン酸の合計に対して1〜20質量%含有させて、ポリアミド樹脂の末端に末端変性用化合物を結合させることにより、下記一般式(I)で表される末端構造を1〜20質量%含有する末端変性ポリアミド樹脂を得る工程と、連続した強化繊維に、または不連続の強化繊維が分散した強化繊維基材に前記末端変性ポリアミド樹脂を含浸させる工程を少なくとも有する請求項2〜13のいずれかに記載の繊維強化ポリアミド樹脂基材の製造方法。
H−X−(R1−O)m−R2 (III)
−X−(R1−O)m−R2 (I)
上記一般式(III)および(I)中、mは2〜100の範囲を表す。R1は炭素数2〜10の2価の炭化水素基、R2は炭素数1〜30の1価の炭化水素基を表す。上記一般式が(III)の場合、−X−は−NH−、−N(CH3)−または−O(C=O)−を表す。上記一般式が(I)の場合、−X−は−NH−、−N(CH3)−または−(C=O)−を表す。一般式(III)中に含まれるm個のR1は同じでも異なってもよい。 - 請求項1〜14のいずれかに記載の繊維強化ポリアミド樹脂基材を含む成形品。
- 請求項1〜13のいずれかに記載の繊維強化ポリアミド樹脂基材と、熱可塑性樹脂を含む成形品とが、少なくとも一部で接合された複合成形品。
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