JP2023024587A - 接着剤、積層体、積層体の製造方法、包装材 - Google Patents
接着剤、積層体、積層体の製造方法、包装材 Download PDFInfo
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- JP2023024587A JP2023024587A JP2022203098A JP2022203098A JP2023024587A JP 2023024587 A JP2023024587 A JP 2023024587A JP 2022203098 A JP2022203098 A JP 2022203098A JP 2022203098 A JP2022203098 A JP 2022203098A JP 2023024587 A JP2023024587 A JP 2023024587A
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- polyisocyanate
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Classifications
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Abstract
Description
本発明の接着剤は、ポリイソシアネート化合物(A)を含むポリイソシアネート組成物(X)と、ポリオール(B)を含むポリオール組成物(Y)と、を含み、ポリオール組成物の50℃における粘度が20mPa・s以上180mPa・s以下である2液硬化型接着剤である。以下、本発明の接着剤について詳細に説明する。
ポリイソシアネート組成物(X)は、ポリイソシアネート化合物(A)を含む。ポリイソシアネート化合物(A)は特に制限なく公知のもの用いることができ、ト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、ポリメリックジフェニルメタンジイソシアネート、1,5-ナフタレンジイソシアネート、トリフェニルメタントリイソシアネート、キシリレンジイソシアネート等の分子構造内に芳香族構造を持つポリイソシアネート、これらのポリイソシアネートのNCO基の一部をカルボジイミドで変性した化合物;
グリセリン、トリメチロールプロパン、ペンタエリスリトール等の3官能又は4官能の脂肪族アルコール;
ビスフェノールA、ビスフェノールF、水素添加ビスフェノールA、水素添加ビスフェノールF等のビスフェノール;
ダイマージオール;
前記鎖状脂肪族グリコール、脂環式グリコール、ダイマージオール、ビスフェノール又は前記ポリエーテルポリオール等のポリオールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(2);
2官能型ポリオールと、前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(4);
ジメチロールプロピオン酸、ヒマシ油脂肪酸等のヒドロキシル酸の重合体である、ポリエステルポリオール(5);
ヒマシ油、ヒマシ油の水素添加物であるヒマシ硬化油、ヒマシ油のアルキレンオキサイド5~50モル付加体等のヒマシ油系ポリオール等が挙げられ、単独または複数を組み合わせて用いることができる。
1,3-シクロペンタンジカルボン酸、1,4-シクロヘキサンジカルボン酸等の脂環式ジカルボン酸;テレフタル酸、イソフタル酸、フタル酸、1,4-ナフタレンジカルボン酸、2,5-ナフタレンジカルボン酸、2,6-ナフタレンジカルボン酸、ナフタル酸、ビフェニルジカルボン酸、1,2-ビス(フェノキシ)エタン-p,p’-ジカルボン酸等の芳香族系ジカルボン酸;
これら脂肪族又は芳香族ジカルボン酸の無水物あるいはエステル形成性誘導体;
p-ヒドロキシ安息香酸、p-(2-ヒドロキシエトキシ)安息香酸及びこれらのジヒドロキシカルボン酸のエステル形成性誘導体、ダイマー酸等の多塩基酸類が挙げられる。
本発明の接着剤に用いられるポリオール組成物(Y)は、ポリオール(B)を含み、50℃における粘度が20mPa・s以上180mPa・s以下である。このようなポリオール組成物(X)はプラスチックフィルムやアルミニウム箔、アルミ蒸着層、無機蒸着層など種々の基材への濡れ性が極めて良好であり、ポリイソシアネート組成物(X)との反応が始まり接着剤層の粘度が上昇する前に十分に濡れ広がることができ、さらにポリオール組成物(Y)と例えば金属層や、ポリエステルフィルムの表面に存在する官能基との相互作用により接着層と基材との密着性が強固なものとなる。すなわち、本発明の接着剤は常温でエージングでき、なおかつ各種基材への密着性に優れたものとなる。なお本明細書におけるポリオール組成物(Y)の粘度は回転粘度計を用い、コーン・プレート:1°×直径50mm、せん断速度:100sec-1、50℃±1℃で測定した値である。
本発明において使用するポリオール(B)は、例えば、エチレングリコール、プロピレングリコール、1,3-プロパンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、3-メチル-1,5-ペンタンジオール、1,6-ヘキサンジオール、ネオペンチルグリコール、メチルペンタンジオール、ジメチルブタンジオール、ブチルエチルプロパンジオール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコール、ビスヒドロキシエトキシベンゼン、1,4-シクロヘキサンジオール、1,4-シクロヘキサンジメタノール、トリエチレングリコール等のグリコール;グリセリン、トリメチロールプロパン、ペンタエリスリトール等の3官能又は4官能の脂肪族アルコール;ビスフェノールA、ビスフェノールF、水素添加ビスフェノールA、水素添加ビスフェノールF等のビスフェノール;ダイマージオール;前記グリコール、3官能又は4官能の脂肪族アルコール等の重合開始剤の存在下にエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド、スチレンオキサイド、エピクロルヒドリン、テトラヒドロフラン、シクロヘキシレン等のアルキレンオキシドを付加重合したポリエーテルポリオール;該ポリエーテルポリオールを更に前記芳香族又は脂肪族ポリイソシアネートで高分子量化したポリエーテルウレタンポリオール;プロピオラクトン、ブチロラクトン、ε-カプロラクトン、σ-バレロラクトン、β-メチル-σ-バレロラクトン等の環状エステル化合物の開環重合反応によって得られるポリエステルと前記グリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の多価アルコールとの反応物であるポリエステルポリオール(1);前記グリコール、ダイマージオール、又は前記ビスフェノール等の2官能型ポリオールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(2):前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(3);2官能型ポリオールと、前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(4);ジメチロールプロピオン酸、ひまし油脂肪酸等のヒドロキシル酸の重合体である、ポリエステルポリオール(5);前記ポリエステルポリオール(1)~(5)と前記ポリエーテルポリオールと芳香族若しくは脂肪族ポリイソシアネートとを反応させて得られるポリエステルポリエーテルポリオール;前記ポリエステルポリオール(1)~(5)を芳香族若しくは脂肪族ポリイソシアネートで高分子量化して得られるポリエステルポリウレタンポリオール;ひまし油、脱水ひまし油、ひまし油の水素添加物であるヒマシ硬化油、ひまし油のアルキレンオキサイド5~50モル付加体等のひまし油系ポリオール等、及びこれらの混合物等が挙げられる。
ポリオール組成物(Y)は、アミン化合物(C)を含むことも好ましい。アミン化合物(C)としては、複数の水酸基を有するアミン化合物(C1)、アミノ基を有するアミン化合物(C2)、活性水素基を有しない3級アミン化合物(C3)が挙げられる。
ポリオール組成物(Y)は、アルコール性水酸基を1つ有するモノオール化合物(D)を含んでいてもよい。モノオール化合物(D)の主鎖は特に制限されず、水酸基を1つ有するビニル樹脂、アクリル樹脂、ポリエステル、エポキシ樹脂、ウレタン樹脂等が挙げられる。また、脂肪族アルコール、アルキルアルキレングリコール等も用いることができる。モノオール化合物(D)の主鎖は、直鎖状であってもよいし、分岐状であってもよい。水酸基の結合位置についても特に限定はないが、分子鎖の末端に存在することが好ましい。モノオール化合物(D)を用いることで、接着剤の硬化塗膜に柔軟性を与えることができ、シール強度の向上が期待できる。
本発明の接着剤は、無溶剤型の形態で用いられる。なお本明細書において「無溶剤型」の接着剤とは、ポリイソシアネート組成物(X)及びポリオール組成物(Y)が酢酸エチル、酢酸ブチル、セロソルブアセテート等のエステル類、アセトン、メチルエチルケトン、イソブチルケトン、シクロヘキサノン等のケトン類、テトラヒドロフラン、ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、メチレンクロリド、エチレンクロリド等のハロゲン化炭化水素類、ジメチルスルホキシド、ジメチルスルホアミド等の溶解性の高い有機溶剤、特に酢酸エチル又はメチルエチルケトンを実質的に含まず、接着剤を基材に塗工した後に、オーブン等で加熱して溶剤を揮発させる工程を経ずに他の基材と貼り合せる方法、いわゆるノンソルベントラミネート法に用いられる接着剤の形態を指す。ポリイソシアネート組成物(X)またはポリオール組成物(Y)の構成成分や、その原料の製造時に反応媒体として使用された有機溶剤が除去しきれずに、ポリイソシアネート組成物(X)やポリオール組成物(Y)中に微量の有機溶剤が残留してしまっている場合は、有機溶剤を実質的に含まないと解される。また、ポリイソシアネート組成物(X)が低分子量アルコールを含む場合、低分子量アルコールはポリオール組成物(Y)と反応して塗膜の一部となるため、塗工後に揮発させる必要はない。従ってこのような形態も無溶剤型接着剤として扱い、低分子量アルコールは有機溶剤とはみなされない。
本発明の接着剤は、上述の成分以外の成分を含んでいてもよい。これらの成分はポリイソシアネート組成物(X)またはポリオール組成物(Y)のいずれかまたは両方に含まれていてもよいし、これらとは別に調整しておき、接着剤の塗工直前にポリイソシアネート組成物(X)、ポリオール組成物(Y)とともに混合して用いてもよい。以下では各成分について説明する。
本発明の接着剤は必要に応じて触媒を使用することにより硬化反応を促進することができる。触媒としては、ポリイソシアネート組成物(X)とポリオール組成物(Y)のウレタン化反応を促進するものであれば特に制限されず、金属系触媒(E1)、脂肪族環状アミド化合物(E2)等が例示される。
本発明の接着剤は、必要に応じて顔料を含んでいてもよい。用いられる顔料としては特に制限はなく、塗料原料便覧1970年度版(日本塗料工業会編)に記載されている体質顔料、白顔料、黒顔料、灰色顔料、赤色顔料、茶色顔料、緑色顔料、青顔料、金属粉顔料、発光顔料、真珠色顔料等の有機顔料や無機顔料、さらにはプラスチック顔料などが挙げられる。
本発明の接着剤は、接着促進剤を含んでいてもよい。接着促進剤としては、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤等のカップリング剤、エポキシ樹脂等が挙げられる。
本発明の接着剤は、上述した成分以外に、レベリング剤、コロイド状シリカやアルミナゾルなどの無機微粒子、ポリメチルメタクリレート系の有機微粒子、消泡剤、タレ性防止剤、湿潤分散剤、粘性調整剤、紫外線吸収剤、金属不活性化剤、過酸化物分解剤、難燃剤、補強剤、可塑剤、潤滑剤、防錆剤、蛍光性増白剤、無機系熱線吸収剤、防炎剤、帯電防止剤、脱水剤、公知慣用の熱可塑性エラストマー、粘着付与剤、燐酸化合物、メラミン樹脂、反応性エラストマー等を含んでいてもよい。これらの添加剤の配合量は、本発明の接着剤の希望を損なわない範囲で適宜調整される。
本発明の積層体は、公知の方法で得ることができる。例えばポリイソシアネート組成物(X)とポリオール組成物(Y)とを事前に混ぜ合わせた後、第一の基材フィルムに塗布、次いで塗布面に第二の基材フィルムを積層し、接着剤層を硬化させて得る2液混合工程を有する方法や、ポリイソシアネート組成物(X)と、組成物ポリオール(Y)とを第一の基材フィルム及び第二の基材フィルムに別々に塗布後、それぞれの塗布面を接触させ圧着させることにより第一の基材フィルムと第二の基材フィルムとを積層させ、接着剤層を硬化させて得る2液分別塗工工程を有する方法により得られる。
本発明の2液硬化型接着剤を用いて製造される積層体および包装材に使用される基材フィルムとしては、積層フィルムで通常使用されるプラスチックフィルムが好ましい。例えば第一の基材フィルムとしては、ポリエチレンテレフタラート(以下PETと略)フィルム、ナイロン(以下Nyと略)フィルム、2軸延伸ポリプロピレン(以下OPPと略)フィルム、各種蒸着フィルム等のベースフィルムやアルミ箔等が挙げられる。また第二の基材フィルムとしては、無延伸ポリプロピレン(以下CPPと略)フィルム、直鎖低密度ポリエチレン(以下LLDPEと略)フィルム等のシーラントフィルムが挙げられる。また基材として紙も使用することができる。紙としては、天然紙や合成紙などが挙げられる。基材層および紙層の外表面または内面側には、必要に応じて印刷層を設けてもよい。
本発明の包装材は、前記積層フィルムを袋状に成形してなり、具体的には前記積層フィルムをヒートシールすることにより包装材の形態となる。また、包装材としての用途、必要な性能(易引裂性やハンドカット性)、包装材として要求される剛性や耐久性(例えば、耐衝撃性や耐ピンホール性など)などを考慮した場合、必要に応じて他の層を積層することもできる。通常は基材層、紙層、第2のシーラント層、不職布層などを伴って使用される。他の層を積層する方法としては、公知の方法を用いることができる。たとえば、他の層との層間に接着剤層を設けてドライラミネート法、熱ラミネート法、ヒートシール法、押出しラミネート法などにより積層すればよい。
本発明の包装材の態様としては、三方シール袋、四方シール袋、ガセット包装袋、ピロー包装袋、ゲーベルトップ型の有底容器、テトラクラッシク、ブリュックタイプ、チューブ容器、紙カップ、蓋材、など種々ある。また、本発明の包装材に易開封処理や再封性手段を適宜設けてあってもよい。
構成1:OPPフィルム/接着層/CPPフィルム
構成2:Nyフィルム/接着層/LLDPEフィルム
構成3:PETフィルム/接着層/CPPフィルム
構成4:PETフィルム/接着層/アルミ蒸着PETフィルム/接着層/LLDPEフィルム
構成5:PETフィルム/接着層/アルミ蒸着CPPフィルム
などが挙げられるが、上述した不具合は、構成3のPETフィルムと接着剤との層間や、構成4、5のアルミ蒸着層と接着層との層間、特にアルミ蒸着層と接着層との層間に顕著に見られる。一般的に、無溶剤型接着剤はアルミ蒸着層との密着性に劣ることが知られているが、本発明の接着剤は基材との密着性に優れ、これらの層間でも剥離が生じにくく、チャック付き包装材のような過酷な条件下で製造される包装材にも好適に用いることができる。他の構成の積層体や包装材にも好適であるのは言うまでもない。
(ポリイソシアネート組成物(X-1))
撹拌機、温度計、窒素ガス導入管を備えたフラスコに、4,4-ジフェニルメタンジイソシアネート36部、2, 4’-ジフェニルメタンジイソシアネート19部を反応容器内に仕込み、窒素ガス下で攪拌し、60℃まで加熱する。数平均分子量400のポリプロピレングリコール(以下、「PPG」と略記する。)を11部、数平均分子量1000のPPGを22部、数平均分子量2000のPPGの11部を数回に分けて滴下し、5~6時間攪拌しウレタン化反応を終了させた。得られたポリイソシアネートのNCO基含有率は、13.5%、50℃における粘度は700mPa.sであった。これをポリイソシアネート組成物(X-1)として用いた。
攪拌機、窒素ガス導入管、スナイダー管、コンデンサーを備えたポリエステル反応容器に、エチレングリコール92.00部、無水フタル酸118.50部、アジピン酸29.23部及びチタニウムテトライソプロポキシド0.01部を仕込み、精留管上部温度が100℃を超えないように徐々に加熱して内温を220℃に保持した。酸価が1mgKOH/g以下になったところでエステル化反応を終了し、数平均分子量500のポリエステル中間体B1’を得た。
表1、2の配合に従ってポリオール組成物(Y-1)~(Y-11)、(Y’-1)~(Y’-5)を調整した。表中における粘度は50℃におけるものであり、単位はmPa・sである。アミン価の単位はmgKOH/gである。表中における化合物の詳細は以下の通りである。
ポリオール(B-1):ひまし油
ポリオール(B-2):ポリプロピレングリコール(Mw=1000)
ポリオール(B-3):ポリプロピレングリコール(Mw=400)
ポリオール(B-4):ポリプロピレントリオール(Mw=3000)
ポリオール(B-5):ポリプロピレングリコール(Mw=4000)
ポリオール(B-6):ポリエーテルポリウレタンポリオール(DIC株式会社製、HA-380B)
ポリオール(B-7):ポリエステルジオール(DIC株式会社製、ODX-2376)
ポリオール(B-8):ポリエステルジオール(DIC株式会社製、HA-700B)
ポリオール(B-9):ポリエステルジオール(上記ポリエステル中間体B1’)
モノオール化合物(D-1):ポリプロピレングリコールモノメチルエーテル(Mw=400)
触媒(E1-1):ジブチル錫ジラウレート(DBTDL)
触媒(E1-2):ネオデカン酸ビスマス
触媒(E1-3):ネオデカン酸亜鉛
触媒(E2-1):ε-カプロラクタム
消泡剤:EVONIK株式会社製、SURFYNOL440
(実施例1)
ポリエステルフィルム(PET、東洋紡株式会社製 E5100、12μm)にポリイソシアネート組成物(X-1)を、アルミ蒸着ポリエステルフィルム(VMPET、東レフィルム加工株式会社製 1310、12μm)のアルミ蒸着面にポリオール組成物(Y-1)を塗布し、PETとVMPETとをニップロール(50℃)で圧着してPET/接着層/VMPETの積層体1を得た。ポリイソシアネート組成物(X-1)、ポリオール組成物(Y-1)の塗布量はそれぞれ、1.3g/m2、0.7g/m2であった。
エージング時間を24時間とした以外は積層体2と同様にして積層体3を得た。
(実施例1)
ポリアミドフィルム(Ny、ユニチカ株式会社製、ON、15μm)にポリイソシアネート組成物(X-1)を、アルミ蒸着ポリエステルフィルム(VMPET、東レフィルム加工株式会社製 1310、12μm)のアルミ蒸着面にポリオール組成物(Y-1)を塗布し、NyとVMPETとをニップロール(50℃)で圧着してNy/接着層/VMPETの積層体4を得た。ポリイソシアネート組成物(X-1)、ポリオール組成物(Y-1)の塗布量はそれぞれ、1.3g/m2、0.7g/m2であった。
用いるポリイソシアネート組成物(X)、ポリオール組成物(Y)と、その塗布量を表4~7のように変更した以外は実施例1と同様にして実施例、比較例の評価用サンプル1~3を得た。
(チャックシール適性)
評価用サンプル1のチャックテープ端部とヒートシールが重なる部分においてアルミ蒸着層と接着層との間の剥離の有無を調べ、以下のようにして5段階で評価した。評価用サンプル2についても同様にして評価し、結果を表8~10にまとめた。
5:20箇所全てにおいて剥離がない
4:20箇所中1箇所で剥離が発生
3:20箇所中2~3箇所で剥離が発生
2:20箇所中4~8箇所で剥離が発生
1:20箇所中9箇所以上で剥離が発生
評価用サンプル3のフィルムの両端を引張試験機に固定し、引張モードで測定した(引張速度:300mm/min)。同じ測定条件で5回測定を行った。得られた強度の最大値の平均値に応じて5段階で評価を行った。
5:最大強度の平均値が100N以上
4:最大強度の平均値が80N以上100N未満
3:最大強度の平均値が70N以上80N未満
2:最大強度の平均値が60N以上70N未満
1:最大強度の平均値が60N未満
Claims (12)
- ポリイソシアネート化合物(A)を含むポリイソシアネート組成物(X)と、
ポリオール(B)を含むポリオール組成物(Y)と、を含み、
前記ポリオール組成物の50℃における粘度が20mPa・s以上180mPa・s以下である2液硬化型接着剤。 - 前記ポリオール組成物が、アミン化合物(C)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール組成物のアミン価が1mgKOH/g以上100mgKOH/g以下である請求項2に記載の2液硬化型接着剤。
- 前記アミン化合物(C)が複数の水酸基を有するアミン化合物(C1)を含む請求項2または3に記載の2液硬化型接着剤。
- 前記アミン化合物(C)がアミノ基を有するアミン化合物(C2)を含む請求項2~4のいずれか一項に記載の2液硬化型接着剤。
- 前記アミン化合物(C)が活性水素基を有しない3級アミン化合物(C3)を含む請求項2~5のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリオール組成物(Y)がモノオール化合物(D)を含む請求項1~6のいずれか一項に記載の2液硬化型接着剤。
- 触媒(E)を含む請求項1~8のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリイソシアネート組成物の50℃における粘度が200mPa・s以上3000mPa・s以下である請求項1~8のいずれか一項に記載の2液硬化型接着剤。
- 第1の基材に、ポリイソシアネート化合物(A)を含むポリイソシアネート組成物(X)を塗布する工程と、
第2の基材に、ポリオール(B)を含み、50℃における粘度が20mPa・s以上180mPa・s以下であるポリオール組成物(Y)を塗布する工程と、
前記第1の基材と前記第2の基材とを、前記ポリイソシアネート組成物(X)と前記ポリオール組成物(Y)とが接触するように貼り合わせる工程とを含む積層体の製造方法。 - 第1の基材と、第2の基材と、前記第1の記載と前記第2の基材とを貼り合わせる接着層とを含み、前記接着層は請求項1~9のいずれか一項に記載の2液硬化型接着剤の硬化塗膜である積層体。
- 請求項11に記載の積層体からなる包装材。
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