JPWO2019188283A1 - ポリオレフィン系接着剤組成物 - Google Patents
ポリオレフィン系接着剤組成物 Download PDFInfo
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- JPWO2019188283A1 JPWO2019188283A1 JP2020509863A JP2020509863A JPWO2019188283A1 JP WO2019188283 A1 JPWO2019188283 A1 JP WO2019188283A1 JP 2020509863 A JP2020509863 A JP 2020509863A JP 2020509863 A JP2020509863 A JP 2020509863A JP WO2019188283 A1 JPWO2019188283 A1 JP WO2019188283A1
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- JP
- Japan
- Prior art keywords
- adhesive composition
- propylene
- modified polyolefin
- base material
- modified
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Abstract
Description
また、前記変性ポリオレフィン(A1)と前記変性ポリオレフィン(A2)の融点の差が3〜55℃であり、融点が50〜160℃、前記変性ポリオレフィン(A1)及び前記変性ポリオレフィン(A2)の酸価がそれぞれ2〜50mgKOH/gであることが好ましい。
<変性ポリオレフィン(A1)および(A2)>
本発明で用いる変性ポリオレフィン(A1)および(A2)は限定的ではないが、ポリエチレン、ポリプロピレンおよびプロピレン・α−オレフィン共重合体の少なくとも1種に、変性がほどこされたものであることが好ましい。また、変性ポリオレフィン(A1)および(A2)はポリプロピレンまたはプロピレン・α−オレフィン共重合体に変性がほどこされたものがより好ましい。
変性ポリオレフィン(A1)と(A2)の融点は異なっていて、(A1)よりも(A2)の方が高融点である。(A1)と(A2)の融点の差は、3〜55℃であることが好ましく、より好ましくは4〜45℃、さらに好ましくは5〜30℃である。前記の範囲外であると低温加工性、耐電解液性、および高温条件における耐久性を並立することができないおそれがある。
本発明で用いられる熱可塑性樹脂(B)は特に限定されないが、スチレン骨格を有する熱可塑性樹脂を用いることができる。スチレン系熱可塑性樹脂として具体的には、スチレン−エチレン−ブチレン−スチレン共重合樹脂、スチレン−エチレン−プロピレン−スチレン共重合樹脂、スチレンーブタジエン共重合樹脂、スチレン−エチレン共重合樹脂、スチレン−ブチレン共重合樹脂、スチレン−エチレン−スチレン共重合樹脂、スチレン−ブチレン−スチレン共重合樹脂などのスチレン系エラストマー等が挙げられる。また、スチレン骨格を有さない熱可塑性樹脂としてはエチレンープロピレン共重合樹脂、エチレン−ブテン共重合樹脂、エチレン−酢酸ビニル共重合樹脂、エチレン−エチルアクリレート共重合樹脂等のオレフィン系エラストマー等が挙げられる。中でもスチレン−エチレン−ブチレン−スチレン共重合樹脂、スチレン−エチレン−プロピレン−スチレンなどのスチレン系エラストマーが、変性ポリオレフィン(A1)および(A2)との相溶性や、耐熱性の観点から好ましい。
本発明の接着剤組成物は変性ポリオレフィン(A1)および(A2)、ならびに熱可塑性樹脂(B)を含有する組成物である。本発明の接着剤組成物は、さらに硬化剤(C)を含有することができる。
接着剤組成物の不揮発分中における(A1)、(A2)および(B)の合計量は60質量%以上が好ましく、70質量%以上がより好ましく、最も好ましくは80質量%以上である。
本発明で用いられる硬化剤(C)は特に限定されないが、例えば、エポキシ硬化剤、イソシアネート硬化剤、カルボジイミド系硬化剤、オキサゾリン系硬化剤などが挙げられ、エポキシ硬化剤またはイソシアネート硬化剤であることが好ましい。
例えば、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、イソホロンジイソシアネート、1,5−ナフタレンジイソシアネート、ヘキサメチレンジイソシアネート、ビス(4−イソシアネートシクロヘキシル)メタン、または水添化ジフェニルメタンジイソシアネート等のジイソシアネートが挙げられる。さらに前記ジイソシアネートから誘導された化合物、即ち、前記ジイソシアネートのイソシアヌレート体、アダクト体、ビウレット型、ウレトジオン体、アロファネート体、イソシアネート残基を有するプレポリマー(ジイソシアネートとポリオールから得られる低重合体)、トリグリシジルイソシアヌレート、またはこれらの複合体等が挙げられる。これらを単独で使用しても良いし、2種以上を任意に組み合わせて使用しても良い。
本発明の積層体は、ポリオレフィン樹脂基材と金属基材を本発明にかかる接着剤組成物で積層したものである。
前記接着剤組成物により形成される接着剤層の厚みは、特に限定されないが、0.5〜10μmにすることが好ましく、0.8〜9.5μmにすることがより好ましく、1〜9μmにすることがさらに好ましい。
ポリオレフィン樹脂基材としては、従来から公知のポリオレフィン樹脂の中から適宜選択すればよい。例えば、特に限定されないが、ポリエチレン、ポリプロピレン、エチレン−プロピレン共重合体などを用いることができる。中でも、ポリプロピレンの無延伸フィルム(以下、CPPともいう。)の使用が好ましい。その厚さは、特に限定されないが、20〜100μmであることが好ましく、25〜95μmであることがより好ましく、30〜90μmであることがさらに好ましい。なお、ポリオレフィン樹脂基材には必要に応じて顔料や種々の添加物を配合してもよいし、表面処理を施してもよい。
金属基材としては、特に限定されないが、例えばアルミニウム、銅、鉄鋼、クロム、亜鉛、ジュラルミン、ダイカストなどの各種金属およびその合金を使用することができる。また、その形状としては、金属箔、圧延鋼板、パネル、パイプ、カン、キャップなど任意の形状を取り得ることができる。一般的には、加工性等の観点からアルミ二ウム箔が好ましい。また、使用目的によっても異なるが、一般的には0.01〜10mm、好ましくは0.02〜5mmの厚みのシートの形で使用される。
また、これら金属基材の表面を予め表面処理を施しておいてもよいし、未処理のままでもよい。いずれも場合であっても同等の効果を発揮することができる。
<<実施例>>
製造例1
1Lオートクレーブに、プロピレン・1−ブテン共重合体(Tm:80℃、プロピレン/1−ブテン=8O/2O モル比)100質量部、トルエン233質量部及び無水マレイン酸20質量部、ジ−tert−ブチルパーオキサイド5質量部を加え、140℃まで昇温した後、更に1時間撹拌した(ここで、1時間「反応」したという)。その後、得られた反応液を100℃まで冷却後、予め40℃に加温したトルエン717質量部とメチルエチルケトン950質量部が入った容器に攪拌しながら注ぎ、40℃まで冷却し、更に30分間攪拌し、更に25℃まで冷却することで樹脂を析出させた(ここで、反応液をメチルエチルケトンなどの溶剤に攪拌しながら注ぎ込み、冷却することで樹脂を析出させる操作を「再沈」という)。その後、当該樹脂を含有するスラリー液を遠心分離することで無水マレイン酸がグラフト重合した酸変性プロピレン・1−ブテン共重合体と(ポリ)無水マレイン酸および低分子量物とを分離した。
更に、遠心分離して取り出した酸変性プロピレン・1−ブテン共重合体を、予め25℃に保温した新たな2000質量部のメチルエチルケトンが入った容器に攪拌しながら投入し、1時間攪拌を続けた。その後、スラリー液を遠心分離することで、更に酸変性プロピレン・1−ブテン共重合体と(ポリ)無水マレイン酸および低分子量物とを分離した。当該操作を2回繰り返すことで、精製した(ここで、遠心分離して取り出した酸変性プロピレン・1−ブテン共重合体をメチルエチルケトンに攪拌しながら投入し、再度遠心分離することで、精製を強化する操作を「リスラリー」とする)。
精製後、減圧下70℃で5時間乾燥させることにより、変性ポリオレフィンである無水マレイン酸変性プロピレン・1−ブテン共重合体(PO−1、酸価25mgKOH/g、重量平均分子量60,000、Tm80℃)を得た。
製造例1で用いたプロピレン・1−ブテン共重合体(Tm:80℃)をプロピレン・1−ブテン共重合体(Tm:90℃、プロピレン/1−ブテン=85/15 モル比)に変更し、リスラリー回数を1回、リスラリーの際に投入するメチルエチルケトンの量を1000質量部に変更した以外は製造例1と同様にすることにより、変性ポリオレフィンである無水マレイン酸変性プロピレン・1−ブテン共重合体(PO−2、酸価25mgKOH/g、重量平均分子量60,000、Tm90℃)を得た。
無水マレイン酸の仕込み量を3質量部、ジ−tert−ブチルパーオキサイドの仕込み量を1質量部に変更し、リスラリー回数を1回、リスラリーの際に投入するメチルエチルケトンの量を1000質量部に変更した以外は製造例1と同様にすることにより、変性ポリオレフィンである無水マレイン酸変性プロピレン・1−ブテン共重合体(PO−3、酸価5mgKOH/g、重量平均分子量90,000、Tm80℃)を得た。
製造例1で用いたプロピレン・1−ブテン共重合体をエチレン・プロピレン共重合体(Tm:100℃、エチレン/プロピレン=75/25 モル比)に変更した以外は製造例1と同様にすることにより、変性ポリオレフィンである無水マレイン酸変性エチレン・プロピレン共重合体(PO−4、酸価25mgKOH/g、重量平均分子量60,000、Tm100℃)を得た。
B−1: クレイトン社製 クレイトン(登録商標)FG1924 (無水マレイン酸変性スチレン・エチレン・ブチレン・スチレン樹脂、酸価11mgKOH/g)
B−2: 旭化成社製 タフテック(登録商標)M1911 (無水マレイン酸変性スチレン・エチレン・ブチレン・スチレン樹脂、酸価2mgKOH/g)
B−3: クレイトン社製 クレイトン(登録商標)FG1901 (無水マレイン酸変性スチレン・エチレン・ブチレン・スチレン樹脂、酸価19mgKOH/g)
B−4: タフマー(登録商標)MH7020(無水マレイン酸変性エチレン‐1−ブテン共重合体、酸価11mgKOH/g
B−5: 旭化成社製 タフテック(登録商標)H1517 (スチレン・エチレン・ブチレン・スチレン樹脂、酸価0mgKOH/g)
B−6: クレイトン社製 クレイトン(登録商標)G1730 (スチレン・エチレン・プロピレン・スチレン樹脂、酸価0mgKOH/g)
B−7: 三井化学社製 タフマー(登録商標)DF640 (エチレン・ブタジエン樹脂、酸価0mgKOH/g)
水冷還流凝縮器と撹拌機を備えた500mlの四つ口フラスコに、製造例1で得られた無水マレイン酸変性プロピレン・1−ブテン共重合体(PO−1)を90質量部、無水マレイン酸変性プロピレン・1−ブテン共重合体(PO−2)を10質量部、熱可塑性樹脂クレイトンFG1924(B-1)を15質量部、シクロヘキサンを424質量部およびメチルエチルケトンを228質量部仕込み、撹拌しながら80℃まで昇温し、撹拌を1時間続けた後、硬化剤(C-1)を3.8質量部、(C-2)を0.5質量部配合し、接着剤組成物を得た。この接着剤組成物を用いて、下記の方法で積層体を作成した。評価結果を表1に示す。
酸変性プロピレン・1−ブテン共重合体または酸変性エチレン・プロピレン共重合体、熱可塑性樹脂を表1および表2に示すとおりに変更し、実施例1と同様な方法で実施例2〜15、比較例1〜6を作製した。配合量および評価結果を表1および表2に示す。
金属基材にはアルミニウム箔(住軽アルミ箔社製、8079−0、厚さ40μm)を使用し、ポリオレフィン樹脂基材には無延伸ポリプロピレンフィルム(東洋紡社製パイレン(登録商標)フィルムCT、厚さ40μm)(以下、CPPともいう。)を使用した。
得られた接着剤組成物を金属基材にバーコータを用いて乾燥後の接着剤層の膜厚が3μmになるように調整して塗布した。塗布面を温風乾燥機を用いて100℃雰囲気で1分間乾燥させ、膜厚3μmの接着剤層が積層された金属基材を得た。前記接着剤層表面にポリオレフィン樹脂基材を重ね合わせ、テスター産業社製の小型卓上テストラミネーター(SA−1010−S)を用いて、ラミネート温度80℃で、0.3MPa、1m/分にて貼り合わせ、40℃、50%RHにて5日間養生することで積層体を得た。
得られた積層体に対して、接着性、耐電解液性、成形性、破断伸度および貯蔵弾性率を評価した。結果を表1および表2に示す。
(C-1) グリシジルエーテル型エポキシ樹脂:jER(登録商標)152(三菱化学社製)
(C-2) グリシジルアミン型エポキシ樹脂:TETRAD(登録商標)−X(三菱ガス化学社製)
(C-3) 多官能ポリイソシアネート:スミジュール(登録商標)N3300(コベストロ社製)
酸価の測定
本発明における酸価(mgKOH/g)は、1gの試料を中和するのに必要とするKOH量のことであり、JIS K0070(1992)の試験方法に準じて、測定した。具体的には、100℃に温度調整したキシレン100gに、変性ポリオレフィンまたは熱可塑性樹脂1gを溶解させた後、同温度でフェノールフタレインを指示薬として、0.1mol/L水酸化カリウムエタノール溶液[商品名「0.1mol/Lエタノール性水酸化カリウム溶液」、和光純薬(株)製]で滴定を行った。この際、滴定に要した水酸化カリウム量をmgに換算して酸価(mgKOH/g)を算出した。
本発明における重量平均分子量は日本ウォーターズ社製ゲルパーミエーションクロマトグラフAlliance e2695(以下、GPC、標準物質:ポリスチレン樹脂、移動相:テトラヒドロフラン、カラム:Shodex KF-806 + KF-803、カラム温度:40℃、流速:1.0ml/分、検出器:フォトダイオードアレイ検出器(波長254nm = 紫外線))によって測定した値である。
本発明における融点は示差走査熱量計(以下、DSC、ティー・エー・インスツルメント・ジャパン製、Q−2000)を用いて、10℃/分の速度で200℃まで昇温後、同速度で−50℃まで冷却し、再度同速度で昇温した際の融解ピークのトップ温度から測定した値である。
ポットライフ性とは、変性ポリオレフィンに硬化剤を配合し、その配合直後または配合後一定時間経過後の該溶液の安定性を指す。ポットライフ性が良好な場合は、溶液の粘度上昇が少なく長期間保存が可能であることを指し、ポットライフ性が不良な場合は、溶液の粘度が上昇(増粘)し、ひどい場合にはゲル化現象を起こし、基材への塗布が困難となり、長期間保存が不可能であることを指す。
接着剤組成物のポットライフ性を、25℃雰囲気で24時間貯蔵した後に、B型粘度計を用いて25℃の溶液粘度を測定することで評価した。
評価結果を表1および表2に示す。
<評価基準>
☆(実用上極めて優れる):300mPa・s未満
◎(実用上特に優れる):300mPa・s以上500mPa・s未満
○(実用上優れる):500mPa・s以上800mPa・s未満
△(実用可能):800mPa・s以上1000mPa・s未満
×(実用不可能):1000mPa・s以上またはゲル化により粘度測定不可
積層体を100mm×15mm大きさに切断し、T型剥離試験により接着性を以下の基準により評価した。
T型剥離試験はASTM−D1876−61の試験法に準拠し、オリエンテックコーポレーション社製のテンシロンRTM−100を用いて、25℃環境下で、引張速度50mm/分における剥離強度を測定した。金属基材/ポリオレフィン樹脂基材間の剥離強度(N/cm)は5回の試験値の平均値とした。
評価基準は以下のとおりとした。
☆(実用上極めて優れる): 8.0N/cm以上
◎(実用上特に優れる): 7.5N/cm以上8.0N/cm未満
○(実用上優れる): 7.0N/cm以上7.5N/cm未満
△(実用可能): 6.5N/cm以上7.0N/cm未満
×(実用不可能): 6.5N/cm未満
リチウムイオン電池の包装材としての利用性を検討するため耐電解液性の評価を行った。積層体を、100mm×15mm大きさに切断し、電解液[エチレンカーボネート/ジエチルカーボネート/ジメチルカーボネート=1/1/1(容積比)100gに6フッ化リン酸リチウムを13g添加したもの]に85℃で1日間浸漬させた。その後、積層体を取り出しイオン交換水で洗浄、ペーパーワイパーで水を拭き取り、十分に水分を乾燥させ、T型剥離試験により耐電解液性を以下の基準により評価した。
☆(実用上極めて優れる): 8.0N/cm以上
◎(実用上特に優れる): 7.5N/cm以上8.0N/cm未満
○(実用上優れる): 7.0N/cm以上7.5N/cm未満
△(実用可能): 6.5N/cm以上7.0N/cm未満
×(実用不可能): 6.5N/cm未満
成形性は作製した積層体の限界成形深さ(深絞り性)により評価した。限界成形深さは、以下の方法で実施した。
積層体を80×120mm大きさに切断し、冷間成形を行った。具体的には、株式会社アマダ製の張り出し成形機(品番:TP−25C−X2)と、55mm×35mmの口径を有する形成金型(雌型)と、これに対応した成形金型(雄型)を用いて、押え圧0.4MPaで0.5mmの成形深さから0.5mm単位で成形深さを変えて、それぞれ10個のサンプル(積層体)について冷間成形を行った。冷間成形後のサンプルについて、皺やアルミニウム箔にピンホール、クラックが10個のサンプル全てにおいて発生しない最も深い成形深さを、そのサンプルの限界成形深さとした。この限界成形深さから、以下の基準により電池用包装材料の成形性を評価した。評価結果を表1および表2に示す。
<評価基準>
☆(実用上極めて優れる): 限界成形深さ6.0mm以上
◎(実用上特に優れる): 限界成形深さ4.0mm以上6.0mm未満
○(実用上優れる): 限界成形深さ3.0mm以上4.0mm未満
△(実用可能): 限界成形深さ2.0mm以上3.0mm未満
×(実用不可能): 限界成形深さ2.0mm未満
本発明における25℃の引張破断伸度(Eb)は、JIS K7161(2014)の試験法に準拠して測定した。具体的には、オリエンテックコーポレーション社製のテンシロンRTM−100を用いて、25℃環境下で、速度50mm/分における引張において破断した際の伸度(%)を測定した値である。
また、85℃の破断伸度は、85℃環境下において同様に測定した値である。得られた接着剤組成物をテフロン(登録商標)シートに500μmアプリケーターを用いて、乾燥後の接着剤層の膜厚が50μmになるように調整して塗布した。塗布面を温風乾燥機を用いて100℃雰囲気で1分間乾燥させた。テフロンシートから接着剤層を剥離し、膜厚50μmの試験片を得た。試験片を50mm×15mmに切断し、前記T型剥離試験と同様の方法で実施し試験片が破断した時点の伸び率により評価した。
☆(実用上極めて優れる): 300%以上
◎(実用上特に優れる): 250%以上300%未満
○(実用上優れる): 220%以上250%未満
△(実用可能): 200%以上220%未満
×(実用不可能): 200%未満
本発明における貯蔵弾性率(E’)は、JIS K7244−4(1999)の試験法に準拠して測定した。具体的には、アイティー計測制御社製、動的粘弾性測定装置 DVA-200を用いて、周波数10Hzにて、−50℃から5℃/分の速度で昇温しながら測定した値である。貯蔵弾性率は80℃環境下、および110℃環境下でそれぞれ測定した。試験片は、前記破断伸度の測定で用いた試験片と同様に作製した。
☆(実用上極めて優れる): 1.0×106Pa以上
◎(実用上特に優れる): 1.0×105Pa以上1.0×106Pa未満
○(実用上優れる): 5.0×104Pa以上1.0×105Pa未満
△(実用可能): 1.0×104Pa以上5.0×104Pa未満
×(実用不可能): 1.0×104Pa未満
Claims (14)
- 変性ポリオレフィン(A1)、プロピレンを30モル%以上含有し変性ポリオレフィン(A1)よりも融点の高い変性ポリオレフィン(A2)、および熱可塑性樹脂(B)を含有する接着剤組成物。
- 前記変性ポリオレフィン(A1)のプロピレンと1−ブテンのモル比がプロピレン/1−ブテン=98〜40/2〜60であり、前記変性ポリオレフィン(A2)のプロピレンと1−ブテンのモル比がプロピレン/1−ブテン=99〜55/1〜45である、請求項1に記載の接着剤組成物。
- 前記変性ポリオレフィン(A1)と前記変性ポリオレフィン(A2)の融点の差が3〜55℃である、請求項1または2に記載の接着剤組成物。
- 前記変性ポリオレフィン(A1)及び前記変性ポリオレフィン(A2)の酸価がそれぞれ2〜50mgKOH/gである、請求項1〜3いずれかに記載の接着剤組成物。
- 前記変性ポリオレフィン(A1)と前記変性ポリオレフィン(A2)の融点がそれぞれ50〜160℃である、請求項1〜4いずれかに記載の接着剤組成物。
- 前記熱可塑性樹脂(B)が酸変性熱可塑性樹脂である、請求項1〜5いずれかに記載の接着剤組成物。
- 前記熱可塑性樹脂(B)が、2〜50mgKOH/gの酸価を有する、請求項1〜6いずれかに記載の接着剤組成物。
- 前記熱可塑性樹脂(B)が、スチレン系熱可塑性樹脂である、請求項1〜7いずれかに記載の接着剤組成物。
- さらに硬化剤(C)を含有する請求項1〜8いずれかに記載の接着剤組成物。
- 前記硬化剤(C)が、エポキシ硬化剤またはイソシアネート硬化剤である、請求項9に記載の接着剤組成物。
- 前記熱可塑性樹脂(B)の質量比が、前記変性ポリオレフィン(A1)および前記変性ポリオレフィン(A2)の合計量100質量部に対して5〜30質量部である、請求項1〜10いずれかに記載の接着剤組成物。
- ポリオレフィン樹脂基材と金属基材との接着に用いられる請求項1〜11のいずれかに記載の接着剤組成物。
- 請求項1〜12のいずれかに記載の接着剤組成物によって接着されたポリオレフィン樹脂基材と金属基材の積層体。
- 請求項13に記載の積層体を構成部材とするリチウムイオン電池用包装材料。
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ES2974056T3 (es) | 2024-06-25 |
TWI813648B (zh) | 2023-09-01 |
KR20200135862A (ko) | 2020-12-03 |
CN111971360A (zh) | 2020-11-20 |
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