JP3588314B2 - 貼り合わせ用ウレタン接着剤組成物 - Google Patents

貼り合わせ用ウレタン接着剤組成物 Download PDF

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JP3588314B2
JP3588314B2 JP2000247932A JP2000247932A JP3588314B2 JP 3588314 B2 JP3588314 B2 JP 3588314B2 JP 2000247932 A JP2000247932 A JP 2000247932A JP 2000247932 A JP2000247932 A JP 2000247932A JP 3588314 B2 JP3588314 B2 JP 3588314B2
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Prior art keywords
polyester
adhesive composition
diisocyanate
adhesive
composition according
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JP2001098247A (ja
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チェン マイ
エイチ．デイッチ ジェフリー
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モートン インターナショナル，インコーポレイティド
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
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    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
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Description

【０００１】
【発明の属する技術分野】
本発明は、ポリマーフィルムを接合するのに有用な貼り合わせ用接着剤に関し、特に食品、医薬品等のためのポリマーフィルム積層体を提供することに関する。本発明の貼り合わせ用接着剤は、水も有機溶剤も含まないという意味で「無溶剤型」の接着剤である。この接着剤は、優れた酸素遮断性及び防湿性を備えている。
【０００２】
【従来の技術及び発明が解決しようとする課題】
酸素、湿分及び他の気体は多くの食品及び医薬品の品質を劣化させる傾向を有する。食品包装、医薬品包装等に有用な多くのポリマーフィルムが、酸素及び湿分が比較的透過しうるものである。遮断性を高めるために、ポリマーフィルムは、高遮断性を有する接着剤層を使用して積層体に形成される。
【０００３】
現在のところ、遮断性のある貼り合わせ用接着剤は主として水性又は溶剤型のポリ塩化ビニリデン（ＰＶＤＣ）配合物である。溶液が水性である場合には、水を蒸発させるためにエネルギーを消費させる必要がある。有機溶剤型配合物も、溶剤を除去するために若干のエネルギー消費を伴い、さらに溶剤は作業場及び環境に有害である。無溶剤型貼り合わせ機のみを所有する包装業者は、ＰＶＤＣで予めコーティングされたフィルムを使用しなくてはならない。また、ＰＶＤＣ中の塩素は環境汚染物質の発生原因である。
【０００４】
もう１つ別の高遮断性材料にはエチレンビニルアルコール（ＥＶＯＨ）があるが、これは典型的には水性接着剤配合物として適用される。ＥＶＯＨは塩素を含まないが、配合物中の水はエネルギーの消費を必要とする。ＥＶＯＨは高い融点、すなわち１５０℃よりも高い融点を有する。そのような高い融点では、また殆どのポリマーフィルムが溶融する。従って、ＥＶＯＨを溶剤型接着剤として適用することはできない。ＥＶＯＨは酸素及び他の気体に対して優れた遮断性を有するが、不十分な防湿性を有する。また、ＥＶＯＨは比較的高価である。
【０００５】
本発明は、貼り合わせに有用であり、かつ酸素及び湿分の両方に対する高い遮断性を提供する無溶剤型ウレタン接着剤に関する。殆どの商用の無溶剤型ウレタン接着剤は、それらがアモルファスポリマーとなる傾向があるために、非常に不十分な酸素遮断性を有する。
【０００６】
【課題を解決するための手段】
本発明は、ポリマー材料の第１フィルムをポリマー材料の第２フィルムに貼り合わせる方法であって、
末端ヒドロキシル基及び２〜１０個の炭素原子を有する１種の線状脂肪族ジオールと１種の線状ジカルボン酸から形成された溶融状態にある無溶剤ヒドロキシル末端ポリエステルであって、３００〜５０００の数平均分子量及び８０℃以下の融点を有するポリエステル（Ａ）を準備する工程；
液体状態にある１種のジイソシアネート（Ｂ）を準備する工程；
前記ジイソシアネート（Ｂ）と前記ポリエステル（Ａ）を１〜１．１の間のＮＣＯ／ＯＨ比で混合して接着剤混合物（Ｉ）を形成させるか、又は前記ジイソシアネート（Ｂ）の全部若しくは一部（Ｂ’）を前記ポリエステル（Ａ）の一部（Ａ’）と２〜８の間のＮＣＯ／ＯＨ比で反応させてウレタンプレポリマー（Ｃ）を形成させ、前記ポリエステル（Ａ）の残りの部分（Ａ’’）及びもし存在するならば前記ジイソシアネート（Ｂ）の残りの部分（Ｂ’’）と前記ウレタンプレポリマー（Ｃ）とを混合し、（Ｂ）に対する（Ａ）のＮＣＯ／ＯＨ比が１〜１．１の間である接着剤混合物（ＩＩ）を形成させる工程；
前記接着剤混合物（Ｉ）又は（ＩＩ）を前記第１フィルム及び第２フィルムの片方又は両方に適用する工程であって、前記接着剤混合物が前記フィルムとの接触直前に調製される工程；
前記混合物の実質的な硬化及びそれに伴うポリウレタン接着剤の形成に先立って、結晶性ポリエステルドメインが形成されるように前記第１フィルムと第２フィルムを接着させる工程；並びに
前記ジイソシアネート（Ｂ）及び前記ポリエステル（Ａ）を完全に反応させ、それにより高いガス遮断特性を有する接着層を形成する工程；
を含む方法を提供する。
【０００７】
本発明の無溶剤型ウレタン接着剤は、２〜１０個の炭素原子、好ましくは３〜６個の炭素原子を有する１種の線状脂肪族ジオール及び１種の線状ジカルボン酸から形成されたヒドロキシル末端ポリエステル（Ａ）と１種の液状ジイソシアネート（Ｂ）とが約１〜約１．１の間のＮＣＯ／ＯＨ比で反応した反応生成物を含む。前記ポリエステル（Ａ）は、周囲温度で結晶質であり、約８０℃以下、好ましくは約７０℃以下、より好ましくは約６０℃以下、最も好ましくは約５５℃以下の融点を有する。前記ポリエステルの数平均分子量（Ｍｎ ）は、約３００〜約５０００の間、好ましくは約５００〜約２０００の間である。結果として得られるウレタンは、１種の線状ジオール、１種の線状ジカルボン酸及び１種のジイソシアネートから形成されるため、ポリウレタンは高い結晶性を有し、それに伴って高い酸素遮断性及び高い防湿性を有する。前記ポリエステルの低い融点はいかなる溶剤も必要とせずに低温での接着剤の適用を可能にするため、貼り合わされるポリマーフィルムは分解も変形もしない。
【０００８】
前記ポリエステル（Ａ）の一部（Ａ’）を前記イソシアネート（Ｂ）の全部又は一部（Ｂ’）と約２〜約８のＮＣＯ／ＯＨ比で反応させてウレタンプレポリマー（Ｃ）を形成させ、その後にポリエステル（Ａ）の残りの部分（Ａ’’）をプレポリマー（Ｃ）及びイソシアネート（Ｂ）の残りの部分（Ｂ’’）と混合してフィルムを貼り合わせるのに適する接着剤混合物を形成させることは本発明の範囲内に含まれることであり、ある場合に好ましい。そのような場合においても、（Ａ’）及び（Ａ’’）の両方を包含する（Ａ）に対する（Ｂ’）及び（Ｂ’’）を包含する（Ｂ）のＮＣＯ／ＯＨ比は約１〜約１．１の間である。
【０００９】
【発明の実施の形態】
前記ポリエステルを形成するのに好ましい線状脂肪族ジオールは、Ｃ３ 〜Ｃ６ ジオールであり、優れた遮断性を有する接着剤を形成するという観点及び経済的観点からｎ−ブタンジオール及びｎ−ヘキサンジオールが好ましいジオールである。
【００１０】
アジピン酸は本発明のポリエステルを形成するのに好ましいジカルボン酸であるが、他の適切なジカルボン酸が使用されてもよい。このような適切なジカルボン酸としてはアゼライン酸及びセバシン酸があるが、これらに限定されない。
【００１１】
現在のところ、最も好ましいポリエステルは、１，６−ヘキサンジオール又は１，４−ブタンジオールとアジピン酸との反応生成物である。
【００１２】
約２０〜約３５０、好ましくは約１００〜約２５０のＯＨ価を有するヒドロキシル末端ポリエステルが形成するようにジオールを反応させる。
【００１３】
好ましいジイソシアネートは、脂肪族ジイソシアネート、特に線状ジイソシアネートであり、高分子量ヘキサメチレンジイソシアネート（ＨＤＩ）が挙げられる。
【００１４】
しかしながら、メチレンジフェニルジイソシアネート（ＭＤＩ）、ジシクロヘキシルメタン４，４’−ジイソシアネート（Ｈ１２ＭＤＩ）及びトルエンジイソシアネート（ＴＤＩ）を包含する他のジイソシアネートが使用されてもよい。ジイソシアネートは、概して、ポリエステルよりも小さな割合で線状ポリウレタン鎖を構成する。そのため、ジイソシアネートの選択はポリエステルの性質よりも概して厳密ではない。遮断性が非常に優れた遮断層を形成する観点から、高分子量ＨＤＩが現在のところ好ましい。しかしながら、高分子量ＨＤＩは比較的高価な材料であり、遮断性に対する要求があまり厳しくない場合にはＭＤＩのようなあまり高価でないジイソシアネートを使用することができる。
【００１５】
本発明において有用なジイソシアネートは、周囲温度、すなわち２０〜２５℃で液状である。本発明の低分子量ポリエステルは非常に結晶性が高いが、それらの分子量が小さいために比較的低い温度で溶融する。ポリエステルは、周囲温度よりもほんの僅か高い温度であるが積層体を形成するポリマーフィルムが分解又は変形しない温度で接着剤を適用することができるように、周囲温度よりもほんの僅か高い低温で溶融することが必要である。このことは、当然のことながらポリマーフィルムの個々の性質に依存するが、より感熱性の高いフィルムに対してはポリエステルが約８０℃以下の温度で溶融することが望ましい。
【００１６】
高速貼り合わせ機を使用する適用、例えば、６００ｆｔ／分（１８３ｍ／分）以上の速度での適用に対しては、ジイソシアネート／ポリエステル混合物の粘度は貼り合わせ温度で約３００〜約２０００ｃｐｓであることが好ましく、貼り合わせ温度で約４００〜約１０００ｃｐｓであることがより好ましい。貼り合わせ温度は、好ましくは８０℃以下、より好ましくは７０℃以下、さらに好ましくは６０℃以下、最も好ましくは５５℃以下である。すなわち、参考までに述べると、個々の適用に依存して、上記粘度は、先に列挙した温度のうちの少なくとも１つの温度、すなわち８０℃、７０℃、６０℃又は５５℃での粘度に該当すべきである。
【００１７】
本発明の接着剤は、ポリプロピレン、ポリエチレン、ポリエステル、ポリアミドのフィルム及び同時押出フィルムを包含する種々のポリマーフィルムを接着するのに有用である。当然のことながら、この接着剤は、不十分な遮断性を有するフィルムを接着させて高遮断性積層体を提供することにおいて最も有用である。２枚のフィルム同士の間の接着性は非常に優れ、このウレタン接着剤から形成される積層体は剥離性でない。
【００１８】
概して、貼り合わせ前、すなわち貼り合わせ前の約１分以内に２つの接着剤成分が混合される。溶融ポリエステルは液状ジイソシアネートと混合され、接着剤混合物組成物が形成される。接着剤混合物組成物は、ポリマーフィルムのうちの１枚に適用され、両方のフィルムがニップに通され、そしてその結果として得られる積層体がリールに巻き取られる。塗布量は、典型的には１〜３ポンド毎連（１．６〜４．９ｇ／ｍ２ ）、好ましくは約１．５ポンド毎連（２．４ｇ／ｍ２ ）である。高い遮断性を達成するには、速度が遅いウレタン形成反応が最も望ましく、貼り合わせ後に、積層体は巻き取られ、そのリールは周囲温度でイソシアネートとポリエステルのヒドロキシル基の間の反応を完了させるのに十分な時間貯蔵される。周囲温度で少なくとも１週間の貯蔵が望ましい。
【００１９】
低粘度イソシアネートキャップドプレポリマーが形成されるようにジイソシアネートをポリエステルの一部と予備反応させ、ポリエステルの残りをプレポリマーと反応させること、及び適用の時点でＮＣＯ／ＯＨ比が約１〜約１．１であることも本発明の範囲内に含まれる。いずれの場合においても、高結晶性であり、そのため酸素、湿分及び他の気体に対して高遮断性である接着剤層を提供するために、１種のジオール、ジカルボン酸及び好ましくはジイソシアネートが使用される。プレポリマーが形成される場合には、プレポリマーを形成する際に約２〜約８の間のＮＣＯ／ＯＨ比が概して使用される。ポリエステルの一部をジイソシアネートと予備反応させたプレポリマーを形成させることの主な理由は、接着剤混合物組成物の粘度が適用温度で低くなりすぎないようにするためである。概して、この方法に従う場合には、ジイソシアネートの全部がポリエステルの適切な割合の一部と反応する。しかしながら、ジイソシアネートの２５重量％がポリエステルの適切な割合の一部と予備反応したとしても、粘度の実質的な調節が確認される。粘度調節のためにウレタンプレポリマーが望ましい場合には、ポリエステルの少なくとも５０重量％を予備反応させることが望ましい。
【００２０】
ポリエステルをジイソシアネートと反応させる場合であってもウレタンプレポリマーをポリエステルと反応させる場合であっても、ポリエステルをイソシアネートと反応させる際に１のＮＣＯ／ＯＨ比が理論的に望ましい。しかしながら、ポリエステルがポリエステル縮合反応に由来する若干の残留水を含みうるため、約１．１のＮＣＯ／ＯＨ比まで僅かに過剰のジイソシアネートが典型的には使用される。
特定の実施例によって本発明をより詳細に説明する。
【００２１】
【実施例】
実施例１〜５
実施例１：１，４−ブタンジオールアジペート（ＯＨ価２２５）のポリエステル１３重量部（ｐｂｗ）を１０重量部の高分子量ＨＤＩと混合した。混合物を１．６ポンド毎連（２．６ｇ／ｍ２ ）の塗布量で１ミル（２５ミクロン）の透明延伸ポリプロピレン（ＯＰＰ）フィルム上にコーティングした。コーティングされたフィルムを１６０°Ｆ（７１℃）のニップ温度でもう１枚の１ミル（２５ミクロン）ＯＰＰフィルムに貼り合わせた。
【００２２】
実施例２：２６．４ｐｂｗの１，６−ヘキサンジオールアジペート（ＯＨ価１１２）を１０ｐｂｗのＨＤＩポリイソシアネートと混合した。接着剤を２ポンド／連（３．２５ｇ／ｍ２ ）の塗布量で１ミルの低密度ポリエチレン（ＬＤＰＥ）フィルム上にコーティングした。コーティングされたフィルムを１６０°Ｆ（７１℃）のニップ温度でもう１枚の１ミル（２５ミクロン）ＬＤＰＥフィルムに貼り合わせた。
【００２３】
実施例３：４０ｐｂｗの１，６−ヘキサンジオールアジペート（ＯＨ価１１２）を１０ｐｂｗの２，４’−４，４’−メチレンジフェニルジイソシアネート（ＭＤＩ）と混合した。混合物を使用し、１６０°Ｆ（７１℃）のニップ温度で２枚の１ミル（２５ミクロン）同時押出（ＣＯＥＸ）フィルムを貼り合わせた。
【００２４】
比較例４：４０ｐｂｗのジエチレングリコールアジペート（ＯＨ価１１２）を１０ｐｂｗの２，４’−４，４’−ＭＤＩと混合し、実施例３におけるように積層体を形成することに使用した。
【００２５】
比較例５：従来のアモルファスウレタン接着剤を使用し、実施例２におけるように２枚の１ミル（２５ミクロン）ＬＤＰＥフィルムを貼り合わせた。
【００２６】
参考のため、実施例において使用した接着剤層を有していない１ミル（２５ミクロン）の各フィルム層は湿度０％、７５°Ｆ（２３．９℃）で次の酸素透過度（ＯＴＲ）（単位： ｃｃ／ｉｎ２／日）を有していた：ＬＤＰＥ ４７９．０；ＯＰＰ
９８．０；ＣＯＥＸ ８５．６。
結果（湿度０％、７５°Ｆ（２３．９℃）でのＯＴＲ（ｃｃ／ｉｎ２／日））は次の通りである：
【００２７】
【表１】
Figure 0003588314
【００２８】
実施例１の透湿度は０．１３ｃｃ／１００ｉｎ２／日であり、これに対して１ミル（２５ミクロン）のＯＰＰ層の透湿度は０．４０ｃｃ／１００ｉｎ２／日であった。

Claims (6)

  1. 高遮断性接着剤を形成するための貼り合わせ用ウレタン接着剤組成物であって、
    （Ａ）が末端ヒドロキシル基及び２〜１０個の炭素原子を有する１種の線状脂肪族ジオールと１種の線状ジカルボン酸から形成された溶融状態にあるヒドロキシル末端ポリエステルであって、３００〜５０００の数平均分子量及び８０℃以下の融点を有するヒドロキシル末端ポリエステルであり、
    （Ｂ）が１種のジイソシアネートであり、
    （Ｃ）が前記ジイソシアネート（Ｂ）の全部若しくは一部（Ｂ’）を前記ポリエステル（Ａ）の一部（Ａ’）と２〜８のＮＣＯ／ＯＨ比で反応させて得られる反応生成物であるウレタンプレポリマーであり、
    （Ａ''）が前記ポリエステル（Ａ）の残りの部分であり、
    （Ｂ''）が前記ジイソシアネート（Ｂ）の残りの部分であるとすると、（Ａ）を含む第１部分と（Ｂ）を含む第２部分との又は（Ａ''）を含む第１部分ともし存在するならば（Ｂ''）及び（Ｃ）を含む第２部分との無溶剤液状混合物であって、前記ポリエステル（Ａ）に対する前記イソシアネート（Ｂ）のＮＣＯ／ＯＨ比が１〜１．１の間である無溶剤液状混合物を含む貼り合わせ用ウレタン接着剤組成物。
  2. 前記ジオールが３〜６個の炭素原子を有する請求項１記載の接着剤組成物。
  3. 前記ポリエステルが５００〜２０００の間の数平均分子量を有する請求項１記載の接着剤組成物。
  4. 前記ポリエステルが７０℃以下の融点を有する請求項１記載の接着剤組成物。
  5. 前記ポリエステルが６０℃以下の融点を有する請求項１記載の接着剤組成物。
  6. 前記ポリエステルが５５℃以下の融点を有する請求項１記載の接着剤組成物。
JP2000247932A 1997-09-17 2000-08-09 貼り合わせ用ウレタン接着剤組成物 Expired - Lifetime JP3588314B2 (ja)

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