JP6481321B2 - ウレタン化触媒、ポリオール混合物、接着剤、及び積層フィルム - Google Patents
ウレタン化触媒、ポリオール混合物、接着剤、及び積層フィルム Download PDFInfo
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- JP6481321B2 JP6481321B2 JP2014204795A JP2014204795A JP6481321B2 JP 6481321 B2 JP6481321 B2 JP 6481321B2 JP 2014204795 A JP2014204795 A JP 2014204795A JP 2014204795 A JP2014204795 A JP 2014204795A JP 6481321 B2 JP6481321 B2 JP 6481321B2
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- Prior art keywords
- polyol
- adhesive
- polyisocyanate
- amide compound
- cyclic amide
- Prior art date
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- 230000001070 adhesive effect Effects 0.000 title claims description 46
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- 229920005862 polyol Polymers 0.000 claims description 52
- 150000003077 polyols Chemical class 0.000 claims description 52
- -1 aliphatic cyclic amide compound Chemical class 0.000 claims description 48
- 239000005056 polyisocyanate Substances 0.000 claims description 47
- 229920001228 polyisocyanate Polymers 0.000 claims description 47
- 229910052719 titanium Inorganic materials 0.000 claims description 25
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- 239000004814 polyurethane Substances 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003118 aryl group Chemical group 0.000 description 18
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
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- 239000011888 foil Substances 0.000 description 4
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
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- 239000005033 polyvinylidene chloride Substances 0.000 description 4
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Adhesives Or Adhesive Processes (AREA)
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Description
斯かる光潜在性キレート触媒を用いた場合には、光照射のタイミングで硬化開始させることができるメリットがあるものの、実際にはポリオール成分とポリイソシアネート成分とを配合直後からの混合液の増粘は避けられず、十分なポットライフ性能が得られないものであった。加えて、硬化促進効果も十分なレベルになくラミネート後の経時的なシール強度が弱いものであった。
に関する。
上記した各種の脂肪族又は芳香族ジケトンは、通常、エノラートアニオンとしてチタン原子に配位するが、そのままチタン原子に配位していてもよい。これらのなかでも本発明では、硬化促進効果が良好である点から構造式L−2、L−5、L−6のものが好ましく、特に構造式L−2のものが好ましい。
攪拌機、温度計、窒素ガス導入管、精留管、水分分離器等を備えたポリエステル反応容器に、イソフタル酸の41.2質量部、アジピン酸の18.0質量部、セバチン酸の9.8質量部、エチレングリコールの17.3質量部、ネオペンチルグリコールの14.9質量部、1,6−ヘキサンジオールの16.7質量部およびチタン触媒0.006質量部を仕込み、精留管上部温度が100℃を越えないように徐々に加熱して内温を240℃に保持した。酸価が5mgKOH/gになったところでキシレンを加え水分分離器を用いて同温度でキシレンをリフラックスさせ、酸価2mgKOH/g以下になるまでさらに反応を続けた。10mmHg以下に減圧し、1.5時間保持してエステル化反応を終了し、水酸基価28mgKOH/gの中間体ポリエステルポリオールを得た。
得られた中間体ポリエステルポリオールの100質量部に対し、酢酸エチルを70質量部、イソホロンジイソシアネートを3.1質量部、ジブチル錫ラウレートを0.05質量部加え、80℃で30分間加熱撹拌し、固形分59.6質量%のポリエステルポリウレタン樹脂溶液(水酸基価9mgKOH/g)を得た。
合成例1で得られたポリエステルポリウレタン樹脂溶液に、ε-カプロラクタム、及び、チタンキレート錯体(BASF社製「SOLYFAST0010」、ジピバロイルメタン/イソプロピルアルコール=50/50(質量基準)をリガンドとするチタンキレート錯体)を表1に記載の配合量で添加し、50℃で約1時間保持してポリオール混合物を得た。
次いで、得られたポリオール混合物と、芳香族ポリイソシアネート(トリレンジイソシアネートのトリメチロールプロパンアダクト)の酢酸エチル溶液(固形分75質量%)とを、イソアネート過剰率[当量比(NCO/OH)]が3.8となる割合で配合し、最終的に固形分30質量%になるように酢酸エチルを加えて調製して接着剤を得た。
[ポットライフ評価]
上記接着剤調整直後より25℃で30分間静置した後、ザーンカップ#3で粘度測定を行った。
この配合液を40℃の恒温槽に入れて6時間反応促進した後、25℃で30分間静置した後、再び粘度測定を行った。
さらに室温で静置し続け、18時間後(配合時から24時間後)の粘度測定を行った。結果を表1に示した。
評価◎:24時間後の配合液の粘度が20秒未満
評価○:24時間後の配合液の粘度が25秒未満
評価△:24時間後の配合液の粘度が30秒未満
評価×:24時間後の配合液の粘度が30秒以上
前記ポリエステルウレタンポリイソシアネートを酢酸エチル111.9質量部で希釈した後、50℃で1ヶ月促進した後、着色の状態を目視評価した。結果を表1に示した。
評価◎:無色透明
評価○:微黄色透明
評価×:黄色透明
上記接着剤をフィルムに塗布量が固形分2.5〜3.5g/m2程度となるように塗布し、ドライヤーで乾燥後、紫外線を照射した。
(紫外線照射条件)
80Wメタルハライドランプ使用
ラインスピード10m/分
照射量50mJ/cm2(岩崎電気製積算光量計にて実測・ライン中心部測定)
5回照射(合計250mJ/cm2)
カレンダーロールでこのフィルムの塗布面と別のシーラントフィルムと塗布面に密着させ、ラミネートフィルムを作製した。
ラミネートフィルムはOPP/CPP(NCO減衰率測定用)とNY/LLDPE(経時シール強度測定用)の2構成を作製した。
このラミネートフィルムを40℃の恒温槽に入れ、経時ごとに以下に示す評価試験方法に従って測定した。
なお、使用したフィルムは以下の通りである。
NY:ユニチカ社製「エンブレムON」 (15μm)
LLDPE:三井化学東セロ社製「T.U.X HC 」(60μm)
OPP:フタムラ化学社製「FOR」 (15μm)
CPP:東洋紡社製「パイレンフィルム−CT P−1128」 (30μm)
(経時シール強度測定)
ONY/LLDPEラミネートフィルムをシーラントが内側になるように折り曲げ、折り曲げ部位を1atm、180℃、1秒間でヒートシールした。これを幅15mmになるように短冊状に切り、剥離試験機を用いて剥離速度300mm/分でヒートシール部位の強度をn=5で測定した。結果を表1に示した。
評価5:フィルム破断が生じる
評価4:フィルム破断とエッジ切れが生じる
評価3:エッジ切れが生じる
評価2:エッジ切れと三角剥離が生じる。
評価1:三角剥離が生じる
(イソシアネート減衰率測定)
OPP/CPPラミネートフィルムを、透過方式で赤外吸収スペクトル測定を行い、イソシアネート由来の吸収スペクトル(2270cm−1付近)を測定した。結果を表1に示した。
評価5:イソシアネート反応率が90%以上
評価4:イソシアネート反応率が80%以上
評価3:イソシアネート反応率が70%以上
評価2:イソシアネート反応率が50%以上
評価1:イソシアネート反応率が50%未満
合成例1で得られたポリエステルポリウレタン樹脂溶液に、表1に記載の各触媒成分を配合し、50℃で約1時間保持してポリオール混合物を得た。
次いで、得られたポリオール混合物と、芳香族ポリイソシアネート(トリレンジイソシアネートのトリメチロールプロパンアダクト)の酢酸エチル溶液(固形分75質量%)とを、イソアネート過剰率[当量比(NCO/OH)]が3.8となる割合で配合し、最終的に固型分30質量%になるように酢酸エチルを加えて調製して接着剤を得、実施例1〜5と同様に各種評価を行った。結果を表1に示す。
合成例1で得られたポリエステルポリウレタン樹脂溶液と、芳香族ポリイソシアネート(トリレンジイソシアネートのトリメチロールプロパンアダクト)の酢酸エチル溶液(固形分75質量%)とを、イソアネート過剰率[当量比(NCO/OH)]が3.8となる割合で配合し、最終的に固形分30質量%になるように酢酸エチルを加えて調製して接着剤を得、実施例1〜5と同様に各種評価を行った。結果を表1に示す。
Claims (11)
- 脂肪族環状アミド化合物(A)とチタンキレート錯体(B)とを必須成分とすること特徴とするウレタン化触媒。
- 脂肪族環状アミド化合物(A)とチタンキレート錯体(B)との存在比率[(A)/(B)]が質量基準で1/9〜9/1となる割合である請求項1記載のウレタン化触媒。
- 脂肪族環状アミド化合物(A)とチタンキレート錯体(B)とポリオール(C)とを必須成分とすることを特徴とするポリオール混合物。
- 前記環状アミド化合物(A)が、δ-バレロラクタム、ε−カプロラクタム、ω-エナントールラクタム、η-カプリルラクタム、及びβ-プロピオラクタムからなる群から選ばれる1つ以上の化合物である請求項3記載のポリオール混合物。
- 前記ポリオール(C)が、ポリエーテルポリオール、ウレタン結合含有ポリエーテルポリオール、ポリエステルポリオール、ウレタン結合含有ポリエステルポリエーテルポリオール、ポリエステルポリオールとポリエーテルポリオールとの混合物、ポリエステルポリウレタンポリオール、及び水酸基含有エポキシ樹脂からなる群から選択されるものである請求項4記載のポリオール混合物。
- 前記ポリオール(C)100質量部あたり、前記脂肪族環状アミド化合物(A)を0.05〜5質量部の範囲、前記チタンキレート錯体(B)を0.05〜5質量部の範囲で含有する請求項3記載のポリオール混合物。
- ポリオール(C)と脂肪族環状アミド化合物(A)とチタンキレート錯体(B)とポリイソシアネート(D)とを必須成分とすることを特徴とする接着剤。
- 前記ポリオール(C)と前記脂肪族環状アミド化合物(A)と前記チタンキレート錯体(B)とを予め混合したポリオール混合物(X)と、前記ポリイソシアネート(D)とを用いる請求項7記載の接着剤。
- 前記ポリオール混合物(X)が請求項3〜6の何れか1つに記載のポリオール混合物である請求項8記載の接着剤。
- 前記ポリオール混合物(X)と、前記ポリイソシアネート(D)との使用割合が前記ポリオール混合物(X)中の水酸基と、前記ポリイソシアネート(D)中のイソシアネート基との当量比[イソシアネート基/水酸基]が1.0〜5.0となる割合である請求項8または9に記載の接着剤。
- 請求項7〜10のいずれかに記載の接着剤を第一のフィルム基材に塗布、次いで塗布面に第二のフィルム基材を積層し、該接着剤層を硬化させてなる積層フィルム。
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