JPWO2020013129A1 - ラミネート用接着剤 - Google Patents
ラミネート用接着剤 Download PDFInfo
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- JPWO2020013129A1 JPWO2020013129A1 JP2020530176A JP2020530176A JPWO2020013129A1 JP WO2020013129 A1 JPWO2020013129 A1 JP WO2020013129A1 JP 2020530176 A JP2020530176 A JP 2020530176A JP 2020530176 A JP2020530176 A JP 2020530176A JP WO2020013129 A1 JPWO2020013129 A1 JP WO2020013129A1
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- mass
- derivative
- polyol
- parts
- polyisocyanate
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- 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
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
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Landscapes
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Abstract
Description
1.ポリオールの調製
表1に示す配合処方に基づいて、ポリオールを調製した。
イソフタル酸665.7質量部、テレフタル酸166.4質量部、アジピン酸187.7質量部、エチレングリコール277.9質量部、ネオペンチルグリコール268.6質量部、1,6−ヘキサンジオール395.9質量部、ダイマー酸(クローダ社製、商品名プリポール1013、以下同様。)37.4質量部および酢酸亜鉛0.5質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、コーンプレート型粘度計によって測定される粘度が約6000mPa・s(150℃)のポリエステルポリオールを得た。これを150℃まで冷却した後、無水トリメリット酸9.25質量部を加え、1時間反応させた。この全量を酢酸エチル1500.0質量部に溶解させ、固形分濃度57%の溶液とし、ポリオールを得た。
イソフタル酸665.7質量部、テレフタル酸166.4質量部、アジピン酸187.7質量部、エチレングリコール277.9質量部、ネオペンチルグリコール268.6質量部、1,6−ヘキサンジオール395.9質量部、ダイマー酸37.4質量部および酢酸亜鉛0.5質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、コーンプレート型粘度計によって測定される粘度が約7000mPa・s(150℃)のポリエステルポリオールを得た。これを150℃まで冷却した後、無水トリメリット酸9.25質量部を加え、1時間反応させた。この全量を酢酸エチル1500.0質量部に溶解させ、固形分濃度56%の溶液とし、ポリオールを得た。
イソフタル酸678.4質量部、テレフタル酸169.6質量部、アジピン酸191.3質量部、エチレングリコール283.2質量部、ネオペンチルグリコール273.7質量部、1,6−ヘキサンジオール403.4質量部および酢酸亜鉛0.5質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、コーンプレート型粘度計によって測定される粘度が約6000mPa・s(150℃)のポリエステルポリオールを得た。これを150℃まで冷却した後、無水トリメリット酸9.25質量部を加え、1時間反応させた。この全量を酢酸エチル1500.0質量部に溶解させ、固形分濃度57%の溶液とし、ポリオールを得た。
イソフタル酸665.7質量部、テレフタル酸166.4質量部、アジピン酸187.7質量部、エチレングリコール277.9質量部、ネオペンチルグリコール268.6質量部、1,6−ヘキサンジオール395.9質量部、ダイマー酸37.4質量部および酢酸亜鉛0.5質量部、グリセリン10.0質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、コーンプレート型粘度計によって測定される粘度が約28000mPa・s(150℃)のポリエステルポリオールを得た。この全量を酢酸エチル1500.0質量部に溶解させ、固形分濃度56%の溶液とし、ポリオールを得た。
イソフタル酸157.2質量部、テレフタル酸39.3質量部、グリセリン40.8質量部、1,6−ヘキサンジオール188.7質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、酸価が約6.4の時点でダイマー酸271.6質量部を加えた。さらに、酸価が約4.6の時点でチタンテトラブトキシド0.1質量部を加え、酸価が約0.8のポリエステルポリオールを得た。これを150℃まで冷却した後、無水トリメリット酸67.5質量部を加え、1時間反応させた。この全量を酢酸エチル300.0質量部に溶解させ、固形分濃度70%の溶液とし、ポリオールを得た。
イソフタル酸488.3質量部、アジピン酸137.7質量部、エチレングリコール203.9質量部、ネオペンチルグリコール219.0質量部、1,6−ヘキサンジオール290.5質量部および酢酸亜鉛0.4質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、数平均分子量約5000のポリエステルポリオールを得た。この全量を酢酸エチル800.0質量部に溶解させ、固形分濃度60%の溶液とし、ポリオールを得た。
イソフタル酸488.3質量部、アジピン酸137.7質量部、エチレングリコール203.9質量部、ネオペンチルグリコール219.0質量部、1,6−ヘキサンジオール290.5質量部および酢酸亜鉛0.4質量部を窒素気流下180〜220℃でエステル化反応させ、所定量の水およびグリコールを留出させ、数平均分子量約5000のポリエステルポリオールを得た。これを150℃まで冷却した後、無水トリメリット酸7.85質量部を加え、2時間反応させた。この全量を酢酸エチル805.2質量部に溶解させ、固形分濃度60%の溶液とし、ポリオールを得た。
合成例6のポリオール805.8質量部に、窒素雰囲気下で3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネート16.54質量部、オクチル酸錫0.25質量部を加え、77〜80℃で4時間ウレタン化反応させ、イソシアネート基の消失を確認した後、酢酸エチル177.66質量部を加え、固形分濃度50%の溶液とし、ポリオール(ポリウレタンポリオール)を得た。
2.主剤(ポリオール成分)の調製
表2に示す配合処方に基づいて、主剤(ポリオール成分)を調製した。
合成例1のポリオール700.0質量部に、窒素雰囲気下でVestanat T1890/100(3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネートのイソシアヌレート誘導体、固形分濃度:100質量%、エボニック デグサジャパン社製)13.9質量部、オクチル酸錫0.12質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、リン酸(和光純薬工業製、以下同様。)0.21質量部、アミノシラン(信越化学工業社製、商品名KBM603、以下同様。)0.41質量部、エポキシシラン(信越化学工業社製、商品名KBM403、以下同様。)2.05質量部混合した。この全量に酢酸エチル117.7質量部を混合して、固形分濃度50%の溶液として、主剤を得た。
合成例2のポリオール729.9質量部に、窒素雰囲気下でVestanat T1890/100 14.2質量部、オクチル酸錫0.13質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、エポキシシラン2.12質量部混合した。この全量を酢酸エチル102.1質量部に溶解させ、固形分濃度50%の溶液として、主剤を得た。
合成例2のポリオール729.9質量部に、窒素雰囲気下でD−131N(タケネートD−131N、キシリレンジイソシアネートのイソシアヌレート誘導体、固形分濃度:75質量%、三井化学社製) 18.9質量部、オクチル酸錫0.13質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、エポキシシラン2.12質量部混合した。さらに、酢酸エチル102.1質量部を加えて混合し、固形分濃度50%の溶液として、主剤を得た。
合成例2のポリオール729.9質量部に、窒素雰囲気下でD−110N(タケネートD−110N、キシリレンジイソシアネートのトリメチロールプロパン誘導体(トリオール誘導体)、固形分濃度:75質量%、三井化学社製) 18.9質量部、オクチル酸錫0.13質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、エポキシシラン2.12質量部混合した。この全量を酢酸エチル102.1質量部に溶解させ、固形分濃度50%の溶液として、主剤を得た。
合成例2のポリオール729.9質量部に、窒素雰囲気下でD−140N(タケネートD−140N、3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネートのトリメチロールプロパン誘導体(トリオール誘導体)、固形分濃度:75質量%、三井化学社製) 18.9質量部、オクチル酸錫0.13質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、エポキシシラン2.12質量部混合した。この全量を酢酸エチル102.1質量部に溶解させ、固形分濃度50%の溶液として、主剤を得た。
合成例3のポリオール700.0質量部に、窒素雰囲気下でVestanat T1890/100 13.9質量部、オクチル酸錫0.12質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、リン酸0.21質量部、アミノシラン0.41質量部、エポキシシラン2.05質量部混合した。この全量に酢酸エチル117.7質量部を混合して、固形分濃度50%の溶液として、主剤を得た。
合成例2のポリオール729.9質量部に、窒素雰囲気下でD−170N(タケネートD−170N、ヘキサメチレンジイソシアネートのイソシアヌレート誘導体、固形分濃度:100質量%、三井化学社製)14.2質量部、オクチル酸錫0.13質量部を加え、77〜80℃でウレタン化反応させ、イソシアネート基の消失を確認した後、50℃に冷却し、エポキシシラン2.12質量部混合した。この全量を酢酸エチル102.1質量部に溶解させ、固形分濃度50%の溶液として、主剤を得た。
合成例4のポリオール844.8質量部、合成例5のポリオール39.0質量部、エポキシシラン2.5質量部、酢酸エチル113.64質量部混合し、固形分濃度50%の溶液として、主剤を得た。
合成例8のポリオール600.0質量部、合成例7のポリオール333.3質量部、リン酸0.15質量部、アミノシラン0.3質量部、エポキシシラン4.5質量部、酢酸エチル71.62質量部混合し、固形分濃度50%の溶液として、主剤を得た。
3.ラミネート用接着剤の製造
実施例1〜実施例11、および、比較例1〜比較例3
表3の記載に従って、ポリオール成分とポリイソシアネート成分とを配合し、ラミネート用接着剤を得た。
4.評価
(剥離強度)
各実施例および各比較例のラミネート用接着剤を用いて、ポリエチレンテレフタレートフィルム(厚み12μm)/ナイロンフィルム(厚み15μm:両面コロナ処理)/アルミニウム箔(厚み9μm)/未延伸ポリプロピレンフィルム(厚み60μm:両面コロナ処理)の4層からなる複合フィルムを作製した。
次いで、その2層複合フィルムのナイロンフィルムの一方面に、このラミネート用接着剤を塗布し、有機溶媒を揮散させた後、一方面(塗布面)をアルミニウム箔の他方面に貼り合わせ、3層複合フィルムを得た。次いで、その3層複合フィルムのアルミニウム箔の一方面に、このラミネート用接着剤を塗布し、溶剤を揮散させた後、一方面(塗布面)を未延伸ポリプロピレンフィルムの他方面に貼り合わせた。
上記で得られたラミネートフィルムを使用して、13×17.5cm(シール幅5〜10mm)の大きさの袋を作製し、内容物として食酢/サラダ油/ケチャップを体積比1/1/1で混合したものを130g充填した。
T1890:Vestanat T1890/100、3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネートのイソシアヌレート誘導体、固形分濃度:100質量%、エボニック デグサ ジャパン社製
D−131N:タケネートD−131N、キシリレンジイソシアネートのイソシアヌレート誘導体、固形分濃度:75質量%、三井化学社製
D−110N:タケネートD−110N、キシリレンジイソシアネートのトリメチロールプロパン誘導体(トリオール誘導体)、固形分濃度:75質量%、三井化学社製
D−140N:タケネートD−140N、3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネートのトリメチロールプロパン誘導体(トリオール誘導体)、固形分濃度:75質量%、三井化学社製
D−170N:タケネートD−170N、ヘキサメチレンジイソシアネートのイソシアヌレート誘導体、固形分濃度:100質量%、三井化学社製
AL:アルミニウム箔
NY:ナイロンフィルム
また、上記各試験において用いられたフィルムの詳細を下記する。
ポリエチレンテレフタレートフィルム:東洋紡社製 エステルフィルムE5102
ナイロンフィルム:ユニチカ社製 エンブレムONBC、両面コロナ処理
アルミニウム箔:東洋アルミニウム社製 アルミハクC
未延伸ポリプロピレンフィルム:東レフィルム加工社製 トレファンNO ZK207、両面コロナ処理
なお、上記発明は、本発明の例示の実施形態として提供したが、これは単なる例示にすぎず、限定的に解釈してはならない。当該技術分野の当業者によって明らかな本発明の変形例は、後記請求の範囲に含まれるものである。
Claims (7)
- ポリイソシアネート成分とポリオール成分とを含有し、
前記ポリオール成分は、ポリオールと平均官能基数が2を超過するポリイソシアネート誘導体との反応生成物であるポリウレタンポリオールを含み、
前記ポリイソシアネート誘導体は、芳香脂肪族ジイソシアネート誘導体および/または脂環族ジイソシアネート誘導体であることを特徴とする、ラミネート用接着剤。 - 前記ポリイソシアネート誘導体は、芳香脂肪族ジイソシアネートのイソシアヌレート誘導体および/または脂環族ジイソシアネートのイソシアヌレート誘導体であることを特徴とする、請求項1に記載のラミネート用接着剤。
- 前記ポリイソシアネート誘導体は、3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネートのイソシアヌレート誘導体であることを特徴とする、請求項1に記載のラミネート用接着剤。
- 前記ポリイソシアネート成分は、キシリレンジイソシアネートのイソシアヌレート誘導体および/またはキシリレンジイソシアネートのトリオール誘導体を含有することを特徴とする、請求項1に記載のラミネート用接着剤。
- 前記ポリイソシアネート成分は、キシリレンジイソシアネートのイソシアヌレート誘導体およびキシリレンジイソシアネートのトリオール誘導体を含有することを特徴とする、
請求項1に記載のラミネート用接着剤。 - キシリレンジイソシアネートのイソシアヌレート誘導体の含有割合に対する、キシリレンジイソシアネートのトリオール誘導体の含有割合の比が、1.5以上4以下であることを特徴とする、請求項5に記載のラミネート用接着剤。
- 前記ポリオールは、低分子量ポリオールと多塩基酸との反応生成物であり、
前記多塩基酸は、ダイマー酸を含むことを特徴とする、請求項1に記載のラミネート用接着剤。
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WO2016104510A1 (ja) * | 2014-12-24 | 2016-06-30 | 東洋インキScホールディングス株式会社 | 接着剤組成物および積層体 |
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WO2009072431A1 (ja) * | 2007-12-03 | 2009-06-11 | Mitsui Chemicals Polyurethanes, Inc. | ラミネート用接着剤 |
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JP2014019711A (ja) * | 2012-07-12 | 2014-02-03 | Mitsui Chemicals Inc | ラミネート接着剤 |
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