JPWO2016152370A1 - 無溶剤型ラミネート接着剤、その硬化物、ラミネート接着剤用ポリオール組成物、及び積層フィルム - Google Patents
無溶剤型ラミネート接着剤、その硬化物、ラミネート接着剤用ポリオール組成物、及び積層フィルム Download PDFInfo
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- JPWO2016152370A1 JPWO2016152370A1 JP2016563142A JP2016563142A JPWO2016152370A1 JP WO2016152370 A1 JPWO2016152370 A1 JP WO2016152370A1 JP 2016563142 A JP2016563142 A JP 2016563142A JP 2016563142 A JP2016563142 A JP 2016563142A JP WO2016152370 A1 JPWO2016152370 A1 JP WO2016152370A1
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- adhesive
- polyol
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- solventless
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Classifications
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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Abstract
Description
エチレンオキサイドの重合物であるポリエチレングリコール、プロピレンオキシドの重合物であるポリエチレングリコール、ブチレンオキサイドの重合物であるポリエチレングリコール等が挙げられる。これらのポリアルキレングリコールは、水又はアルコールを開始剤として各アルキレングリコールを重合させることによって製造することができる。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
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%、粘度は1500mPa.sであった。以下このポリイソシアネートを「A−1」と略記する。
撹拌機、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、アジピン酸の60.7部、エチレングリコールの28.2部、ジエチレングリコールの11.1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220℃に保持した。酸価が2.0mgKOH/g以下となったところでエステル化反応を終了しポリエステルポリオールを得た(得られたポリエステルポリオール「中間体PE」とする。)。
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30部、2, 4'-ジフェニルメタンジイソシアネート30部を反応容器内に仕込み、窒素ガス下で攪拌し、60℃まで加熱した。中間体PE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、14.0%、粘度は3000mPa.sであった。以下このポリイソシアネートを「A−2」と略記する。
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55部を反応容器内に仕込み、窒素ガス下で攪拌し、60℃まで加熱した。数平均分子量400のPPGを11部、数平均分子量1000のPPGを22部、数平均分子量2000のPPGを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13.6%、粘度は2000mPa.sであった。以下このポリイソシアネートを「A−3」と略記する。
撹拌機、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19.7部、アジピン酸38.7部、エチレングリコール19.8部、ジエチレングリコールの21.8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220℃に保持した。酸価が2.0mgKOH/g以下となったところでエステル化反応を終了しポリエステルポリオールを得た。水酸基価186(mgKOH/g)、数平均分子量約600。
撹拌機、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21.3部、アジピン酸41.9部、エチレングリコール16.8部、ジエチレングリコールの20.0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220℃に保持した。酸価が2.0mgKOH/g以下となったところでエステル化反応を終了しポリエステルポリオールを得た。水酸基価56(mgKOH/g)、数平均分子量約2000。
表1及び表2の配合に従い、主剤及び硬化剤を調整し、これらを配合して各種評価を行った。
(接着剤外観評価)
接着剤配合時の液の外観を下記基準にて評価した。
○:透明 △:微濁 ×:白濁
(ポットライフ)
主剤と硬化剤とを配合した後40℃、30分後の粘度を測定した。
○:6000mPa.s未満(40℃) ×:6000mPa.s以上(40℃)
(ラミネート外観評価)
主剤と硬化剤とを配合した後、白色白印刷インキ(DIC製「フィナート R794白」でベタ状にグラビア印刷されたポリエチレンテレフタレートフィルム(以下、「PETフィルム」と略記する。)に、塗布量が固形分1.8g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とアルミ蒸着無延伸ポリプロピレン(以下、「VMCPPフィルム」と略記する)とを貼合し、ラミネートフィルムを作製した。
この際、ラミネート速度を150m/分でラミネート加工したものと、150m/分でラミネート加工したものとを、エージング後巻き外10m部分の白インキ部分の外観を下記の基準にて評価した。
次に、白色白印刷インキ(DIC製「フィナート R794白」でベタ状にグラビア印刷された二軸延伸ポリプロピレンフィルム(以下、「OPPフィルム」と略記する。)に、接着剤を塗布量が固形分1.8g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面と無延伸ポリプロピレンフィルム(以下、「CPP」と略記する)とを貼合し、ラミネートフィルムを作製した。
この際、ラミネート速度を300m/分でラミネート加工したものと、350m/分でラミネート加工したものとを、エージング後巻き外10m部分の白インキ部分の外観を下記の基準にて評価した。
スケールルーペを使用して、1cm2スケール内の気泡の数で評価
◎:気泡数0個
○:気泡数1〜4個
△:気泡数5〜16個
×:気泡数:17個以上
無溶剤型ラミネート機を使用し、OPP/CPP構成のラミネート物を高速加工によって製造する際、塗工ロール付近の状態を目視でチェックした。
◎400m/分までミスト無し
○300m/分までミスト無し
△250m/分までミスト無し
×250m/分までにミスト発生
テストラミネーター(テスター産業製)を用いて、塗布量1.8g/m2となるように
白色白印刷インキ(DIC製「フィナート R794白」でベタ状にグラビア印刷された二軸延伸ナイロン(ユニチカ(株)製「エンブレム」15μm。以下、「ONy」と略記する。)フィルムに塗布し、直鎖状低密度ポリエチレン(東セロ(株)製「TUX−HC」60μm、以下、「LLDPEフィルム」と略記する。)とをラミネートし、ラミネート物を作製した。
次いで、このラミネート物を40℃×3日間のエージンングを行い、接着剤塗膜を硬化させ、ONyフィルム/接着剤組成物/LLDPEフィルムの2層の複合フィルムを得た。
エージング後のこの複合フィルムを用いて、120mm×120mmの大きさのパウチを作製し、内容物として、食酢、サラダ油、ミートソースを質量比で1:1:1に配合した疑似食品70gを充填した。作製したパウチについては98℃で60分間のボイル殺菌処理をした後、白インキ部の外観を目視で評価した。
×:デラミネーションあり
表1及び表2中の略号は以下の通りである。
PPG−400:数平均分子量400のポリプロピレングリコール
3官能 PPG−400:数平均分子量400の3官能ポリプロピレングリコール(開始剤:グリセリン)
PPG−1000:数平均分子量1,000のポリプロピレングリコール
PPG−2000:数平均分子量2,000のポリプロピレングリコール
PPG−3000:数平均分子量3,000のポリプロピレングリコール
PPG−4000:数平均分子量3,000のポリプロピレングリコール
PET/VMCPP:ポリエチレンテレフタレートフィルム及びアルミ蒸着未延伸ポリプロピレンフィルムのフィルム構成
OPP/CPP:二軸延伸ポリプロピレンフィルム及び未延伸ポリプロピレンフィルムのフィルム構成
Claims (7)
- ポリイソシアネート成分(A)とポリオール成分(B)とを必須成分とする無溶剤型ラミネート接着剤組成物であって、前記ポリオール成分(B)が、ひまし油又は水酸基含有ひまし油誘導体(b1)と、数平均分子量2,500〜7,000のポリアルキレングリコール(b2)とを含有するものであることを特徴とする無溶剤型ラミネート接着剤。
- 前記ポリオール成分(B)が、水酸基含有植物油と、数平均分子量3,000〜7,000のポリアルキレングリコールとを質量比[水酸基含有植物油/ポリアルキレングリコール]が90/10〜20/80となる割合で含むものである請求項1記載の無溶剤型ラミネート接着剤。
- 前記ポリイソシアネート成分(A)が、芳香族ポリイソシアネートと、ポリエーテルポリオール及び/又はポリエステルポリオールを反応させて得られるものである請求項1記載の無溶剤型ラミネート接着剤。
- 前記ポリイソシアネート成分(A)と、前記ポリオール成分(B)との使用割合が、前記ポリイソシアネート成分(A)中のイソシアネート基と、前記ポリオール成分(B)中の水酸基との当量比[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1記載の無溶剤型ラミネート接着剤。
- ひまし油又は水酸基含有ひまし油誘導体(b1)と、数平均分子量2,500〜7,000のポリアルキレングリコール(b2)とを含有するラミネート接着剤用ポリオール組成物。
- 請求項1、2、3、又は4記載の無溶剤型ラミネート接着剤を硬化させてなる硬化物。
- 請求項4記載の接着剤を第一のプラスチックフィルムに塗布、次いで塗布面に第二のプラスチックフィルムを積層し、該接着剤層を硬化させてなる積層フィルム。
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PCT/JP2016/055623 WO2016152370A1 (ja) | 2015-03-20 | 2016-02-25 | 無溶剤型ラミネート接着剤、その硬化物、ラミネート接着剤用ポリオール組成物、及び積層フィルム |
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EP3481885B1 (en) * | 2016-07-11 | 2023-09-13 | Dow Global Technologies Llc | High-solids content solvent-based adhesive compositions and methods of making same |
JP6797359B2 (ja) * | 2016-09-15 | 2020-12-09 | Dic株式会社 | 包装体 |
CN114921216A (zh) * | 2016-11-25 | 2022-08-19 | 汉高股份有限及两合公司 | 低粘度、快速固化的层合粘合剂组合物 |
WO2018101242A1 (ja) * | 2016-12-02 | 2018-06-07 | Dic株式会社 | 反応型接着剤、積層フィルム及び包装体 |
JP6946251B2 (ja) * | 2017-03-30 | 2021-10-06 | ロックペイント株式会社 | ラミネートフィルム及びこれを用いた包装体 |
JP6792499B2 (ja) * | 2017-03-30 | 2020-11-25 | ロックペイント株式会社 | 酸素吸収性付与ラミネート接着剤 |
WO2018181900A1 (ja) * | 2017-03-31 | 2018-10-04 | 大日本印刷株式会社 | ガスバリア積層体、及び該積層体からなるガスバリア包装材料とピロー包装袋 |
BR112019025351A2 (pt) * | 2017-05-30 | 2020-08-18 | Dow Global Technologies Llc | composições adesivas sem solvente de dois componentes |
US11732080B2 (en) | 2017-06-15 | 2023-08-22 | Ddp Specialty Electronics Materials Us, Inc. | Compositions containing hydrophobic modified isocyanate functional prepolymer containing adhesives |
WO2019049852A1 (ja) * | 2017-09-06 | 2019-03-14 | Dic株式会社 | ガスバリア性接着剤用樹脂組成物、接着剤、及び積層体 |
JP6620964B2 (ja) * | 2017-12-12 | 2019-12-18 | Dic株式会社 | 無溶剤型ラミネート接着剤、その硬化物、積層体及び包装体 |
JP6620963B2 (ja) * | 2017-12-13 | 2019-12-18 | Dic株式会社 | 反応型接着剤、積層フィルム及び包装体 |
JP6992503B2 (ja) * | 2017-12-27 | 2022-01-13 | 東洋インキScホールディングス株式会社 | 積層体 |
TWI711544B (zh) * | 2018-02-27 | 2020-12-01 | 日商迪愛生股份有限公司 | 軟包裝用薄膜之製造方法 |
JP6566286B1 (ja) * | 2018-02-27 | 2019-08-28 | Dic株式会社 | 軟包装用フィルムの製造方法 |
JP6733835B1 (ja) * | 2018-08-28 | 2020-08-05 | Dic株式会社 | 反応性接着剤、積層体、及び包装体 |
BR112021009455B1 (pt) * | 2018-11-16 | 2024-01-09 | Dow Global Technologies Llc | Processo, composição de adesivo sem solvente, e, produto laminado |
WO2020110882A1 (ja) * | 2018-11-28 | 2020-06-04 | Dic株式会社 | 反応性接着剤、積層体、及び包装体 |
CN113195224A (zh) * | 2018-12-21 | 2021-07-30 | Dic株式会社 | 粘接剂、层叠膜及层叠膜的制造方法 |
WO2021086541A1 (en) * | 2019-10-28 | 2021-05-06 | Dow Global Technologies Llc | Polyolefin-based laminating adhesive composition and recyclable laminate |
JP7502913B2 (ja) | 2020-06-23 | 2024-06-19 | ヘンケルジャパン株式会社 | ラミネート用接着剤 |
JP7148705B1 (ja) | 2021-12-21 | 2022-10-05 | 東洋インキScホールディングス株式会社 | 無溶剤型接着剤組成物、積層体、包装体及び積層体の製造方法 |
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EP1985679A4 (en) * | 2006-02-17 | 2012-06-06 | Mitsui Chemicals Inc | STRATIFICATION ADHESIVE |
JP4948507B2 (ja) * | 2007-12-19 | 2012-06-06 | ローム アンド ハース カンパニー | ラミネート接着剤 |
ATE523537T1 (de) * | 2008-12-02 | 2011-09-15 | Sika Technology Ag | Hydroxyaldimin enthaltende polyurethanzusammensetzung |
JP5604407B2 (ja) * | 2010-12-21 | 2014-10-08 | ローム アンド ハース カンパニー | 接着剤組成物 |
JP5909779B2 (ja) * | 2012-06-27 | 2016-04-27 | 東洋インキScホールディングス株式会社 | 積層体および積層体の製造方法 |
EP2708565A1 (de) * | 2012-09-14 | 2014-03-19 | Sika Technology AG | Zweikomponentige Polyurethanzusammensetzungen auf Basis nachwachsender Rohstoffe, insbesondere geeignet für den Einsatz als zähelastische Klebstoffe mit einstellbarer hydrolytischer Abbaubarkeit |
US9181460B2 (en) * | 2013-03-06 | 2015-11-10 | H.B. Fuller Company | Gas transmitting polyurethane adhesive |
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