JP7215091B2 - 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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- JP7215091B2 JP7215091B2 JP2018210518A JP2018210518A JP7215091B2 JP 7215091 B2 JP7215091 B2 JP 7215091B2 JP 2018210518 A JP2018210518 A JP 2018210518A JP 2018210518 A JP2018210518 A JP 2018210518A JP 7215091 B2 JP7215091 B2 JP 7215091B2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
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- HIAAVKYLDRCDFQ-UHFFFAOYSA-L calcium;dodecanoate Chemical compound [Ca+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O HIAAVKYLDRCDFQ-UHFFFAOYSA-L 0.000 description 2
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- ABSWXCXMXIZDSN-UHFFFAOYSA-L magnesium;hexadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O ABSWXCXMXIZDSN-UHFFFAOYSA-L 0.000 description 2
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011574 phosphorus Substances 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 229940114930 potassium stearate Drugs 0.000 description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 2
- PYJBVGYZXWPIKK-UHFFFAOYSA-M potassium;tetradecanoate Chemical compound [K+].CCCCCCCCCCCCCC([O-])=O PYJBVGYZXWPIKK-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
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- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 2
- 229940082004 sodium laurate Drugs 0.000 description 2
- 229940045845 sodium myristate Drugs 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 229940045870 sodium palmitate Drugs 0.000 description 2
- 229940080350 sodium stearate Drugs 0.000 description 2
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 2
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 229940012185 zinc palmitate Drugs 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
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Landscapes
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Description
具体的には、硬化剤配合後の接着剤のポットライフ性確保と耐電解液性両立が困難であり(特許文献1)、押出ラミネーションによる接着を行っていることからラミネート機台が制約されたり、高温での貼り合せによってポリオレフィン基材が熱収縮の影響を受ける(特許文献2)、ポリオレフィン主剤が水系であることから乾燥時間が長く、生産条件が限定されてしまう(特許文献3)などの問題が見られるものであった。
有機溶剤(C1):脂肪族炭化水素および脂環族炭化水素からなる群より選択された1種以上であり、かつ、沸点が110℃未満である有機溶剤
有機溶剤(C2):アルコール系溶剤、ケトン系溶剤、エステル系溶剤およびグリコールエーテル系溶剤からなる群より選択された1種以上であり、かつ、沸点が110℃未満である有機溶剤
有機溶剤(C3):脂肪族炭化水素および脂環族炭化水素からなる群より選択された1種以上であり、かつ、沸点が110℃以上である有機溶剤
有機溶剤(C4):アルコール系溶剤、ケトン系溶剤、エステル系溶剤、およびグリコールエーテル系溶剤からなる群より選択された1種以上であり、かつ、沸点が110℃以上である有機溶剤
<酸変性ポリオレフィン(A)>
本発明で用いられる硬化剤(B)は特に限定されないが、エポキシ硬化剤または多官能ポリイソシアネート硬化剤を使用することが好ましい。
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。
本発明で用いる有機溶剤(C)は、酸変性ポリオレフィン(A)および硬化剤(B)を溶解または分散させるものであれば、特に限定されない。好ましくは、有機溶剤(C)が、有機溶剤(C3)を含み、有機溶剤(C1)、有機溶剤(C2)および有機溶剤(C4)からなる群より選ばれた2種以上の溶剤であり、均一に混ざり合うことが好ましい。
また、有機溶剤(C1)が脂環族炭化水素、有機溶剤(C3)が脂環族炭化水素やパラフィン系溶剤であり、有機溶剤(C2)および有機溶剤(C4)がケトン系溶剤であることが特に好ましい。
本発明にかかる接着剤組成物は、前記酸変性ポリオレフィン(A)、硬化剤(B)および有機溶剤(C)の混合物であり、再溶解性の観点から酸変性ポリオレフィン(A)、硬化剤(B)は、有機溶剤(C)に溶解していることが好ましい。
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。
製造例1
1Lオートクレーブに、プロピレン-ブテン共重合体(Tm:80℃)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-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-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-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-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、酸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-ブテン共重合体(PO-1、酸価25mgKOH/g-resin、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-ブテン共重合体(Tm:80℃)をプロピレン-ブテン共重合体(Tm:90℃)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、酸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-ブテン共重合体(PO-2、酸価25mgKOH/g-resin、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、酸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-ブテン共重合体(PO-3、酸価5mgKOH/g-resin、重量平均分子量90,000、Tm80℃)を得た。
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-ブテン共重合体(PO-1)を100質量部、シクロヘキサンを130質量部、アイソパーEを130質量部およびメチルエチルケトンを140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、冷却することで主剤1を得た。溶液状態を表1に示す。
酸変性ポリオレフィンおよび有機溶剤を表1に示すとおりに変更し、主剤1と同様な方法で主剤2~25を作製した。配合量、溶液状態を表1に示す。
アイソパーE(登録商標、エクソンモービル製):イソパラフィン系溶剤、沸点 115-123℃
シェルゾールMC311(登録商標、シェル化学社製):パラフィン系溶剤、沸点 167-180℃
エクソールD40(登録商標、エクソンモービル製):ナフテン系溶剤、沸点 166-191℃
アイソパーG(登録商標、エクソンモービル製):イソパラフィン系溶剤、沸点 166-177℃
アイソパーL(登録商標、エクソンモービル製):イソパラフィン系溶剤、沸点 184-199℃
主剤1を500質量部、硬化剤(B)としてjER(登録商標)152(三菱化学社製)を25質量部、TETRAD(登録商標)-X(三菱ガス化学社製)を3質量部配合し、接着剤組成物を得た。この接着剤組成物に対し、ポットライフ性、接着性、耐薬品性および再溶解性を評価した。結果を表2に示す。
主剤1~25および各硬化剤を表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2~22、比較例1~4を行った。配合量、ポットライフ性、接着性、耐薬品性および再溶解性の結果を表2に示す。
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)
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)
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-resin)は、1gの酸変性ポリオレフィン(A)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、酸変性ポリオレフィン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、融解熱量は示差走査熱量計(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℃/分の速度で昇温融解、冷却樹脂化して、再度昇温融解した際の融解ピークのトップ温度および面積から測定した値である。
主剤1~25の溶液状態について、東機産業社製のブルックフィールド型粘度計TVB-10M(以下、B型粘度計ともいう)を用いて25℃の溶液粘度を測定することで評価した。
<評価基準>
○(実用可能):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
再溶解性とは、酸変性ポリオレフィン(A)、硬化剤(B)、および有機溶剤(C)を配合した接着剤組成物が、基材への塗布後一定時間経過後に該組成物へ再度溶解する性質を示す。
再溶解性試験の方法
200mLディスポカップに接着剤組成物を150mL入れ、予め重量を測定したブリキ試験板(日本テストパネル社製、切りブリキ、厚さ25μm、大きさ 50mm×10mm)を繰り返し浸漬、25℃30分乾燥後再度試験板の重量を測定する。試験板浸漬はブリキ試験板を該試験板の一端から4.5cmが液面下の状態で2秒浸漬後、基材全体を50cm/秒で液面から引き上げて15秒間25℃雰囲気下で放置し、再度浸漬するまでを1サイクルとし、30サイクル行った。樹脂付着量は浸漬前後の試験板の重量の差を浸漬面積で割った値である。
<評価基準>
☆(実用上特に優れる):55 g/m2以下
◎(実用上優れる):55g/m2を超え100g/m2以下
○(実用可能):100g/m2を超え200 g/m2以下
×(実用不可能):200 g/m2を超える。
ポットライフ性とは、酸変性ポリオレフィンに架橋剤または硬化剤を配合し、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2に示す。
<評価基準>
☆(実用上特に優れる):300mPa・s未満
◎(実用上優れる):300mPa・s以上500mPa・s未満
○(実用可能):500mPa・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
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。
実施例1~22および比較例1~4で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5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、25℃、50%RHにて36時間養生することで積層体を得た。
前記積層体を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。評価結果を表2に示す。
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。
☆(実用上特に優れる):8.0N/cm以上またはCPPが材破する(以下、単に「材破」ともいう。)。材破とは、金属基材/CPPの界面で剥離が生じず、金属基材またはCPPが破壊されることをいう。
◎(実用上優れる):7.5N/cm以上8.0N/cm未満
○(実用可能):7.0N/cm以上7.5N/cm未満
×(実用不可能):7.0N/cm未満
LiBの包装材としての利用性を検討するため電解液試験による耐薬品性(以下、耐電解液性ともいう)の評価を行った。前記積層体を、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、100mm×15mm大きさに切断し、T型剥離試験により耐薬品性を以下の基準により評価した。評価結果を表2に示す。
☆(実用上特に優れる):8.0N/cm以上または材破
◎(実用上優れる):7.5N/cm以上8.0N/cm未満
○(実用可能):7.0N/cm以上7.5N/cm未満
×(実用不可能):7.0N/cm未満
Claims (6)
- 酸変性ポリオレフィン(A)、硬化剤(B)および有機溶剤(C)を含有し、再溶解試験
後の酸変性ポリオレフィン(A)、硬化剤(B)、およびこれらの反応物の付着物の合計量
が200g/m2以下であり、
有機溶剤(C)が、有機溶剤(C3)を含み、有機溶剤(C1)、有機溶剤(C2)および有機溶剤(C4)からなる群より選ばれた2種以上の有機溶剤を含む接着剤組成物、
有機溶剤(C1):脂肪族炭化水素および脂環族炭化水素からなる群より選択された1種以上であり、かつ、沸点が110℃未満である有機溶剤
有機溶剤(C2):アルコール系溶剤、ケトン系溶剤、エステル系溶剤およびグリコールエーテル系溶剤からなる群より選択された1種以上であり、かつ、沸点が110℃未満である有機溶剤
有機溶剤(C3):脂肪族炭化水素および脂環族炭化水素からなる群より選択された1種以上であり、かつ、沸点が110℃以上である有機溶剤
有機溶剤(C4):アルコール系溶剤、ケトン系溶剤、エステル系溶剤、およびグリコールエーテル系溶剤からなる群より選択された1種以上であり、かつ、沸点が110℃以上である有機溶剤。 - 前記硬化剤(B)が、エポキシ樹脂またはイソシアネート樹脂である請求項1に記載の接着剤組成物。
- 酸変性ポリオレフィン(A)100質量部に対して、硬化剤(B)を0.5~40質量部、有機溶剤(C)を80~2000質量部含有する請求項1~2の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1~3のいずれかに記載の接着剤組成物。
- 請求項1~4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5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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TW202018046A (zh) | 2020-05-16 |
KR20210090221A (ko) | 2021-07-19 |
EP3878918A4 (en) | 2022-07-20 |
JP2019112611A (ja) | 2019-07-11 |
EP3878918A1 (en) | 2021-09-15 |
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