JP6947172B2 - 湿気硬化型反応性ホットメルト接着剤組成物及びその製造方法 - Google Patents
湿気硬化型反応性ホットメルト接着剤組成物及びその製造方法 Download PDFInfo
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- JP6947172B2 JP6947172B2 JP2018514246A JP2018514246A JP6947172B2 JP 6947172 B2 JP6947172 B2 JP 6947172B2 JP 2018514246 A JP2018514246 A JP 2018514246A JP 2018514246 A JP2018514246 A JP 2018514246A JP 6947172 B2 JP6947172 B2 JP 6947172B2
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Classifications
-
- 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
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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Description
本明細書において、「〜」を用いて示された数値範囲は、「〜」の前後に記載される数値をそれぞれ最小値及び最大値として含む範囲を示す。本明細書に段階的に記載されている数値範囲において、ある段階の数値範囲の上限値又は下限値は、他の段階の数値範囲の上限値又は下限値に置き換えてもよい。本明細書に記載されている数値範囲において、その数値範囲の上限値又は下限値は、実施例に示されている値に置き換えてもよい。「A又はB」とは、A及びBのどちらか一方を含んでいればよく、両方とも含んでいてもよい。本明細書に例示する材料は、特に断らない限り、1種を単独で又は2種以上を組み合わせて用いることができる。本明細書において、組成物中の各成分の含有量は、組成物中に各成分に該当する物質が複数存在する場合、特に断らない限り、組成物中に存在する複数の物質の合計量を意味する。
本実施形態の湿気硬化型反応性ホットメルト接着剤組成物(以下、「接着剤組成物」と略す場合もある。)は、ポリエステルポリオール、ポリエーテルポリオール及びポリブタジエンポリオールを含有するポリオール成分とイソシアネート成分との反応物であるイソシアネート基を有するウレタンプレポリマーと、酸化防止剤とを含むことを特徴としている。なお、一般的に、湿気硬化型反応性ホットメルト接着剤組成物とは、空気中の水分又は被着体表面の水分と反応することにより高分子量化し、接着性等を発現するものである。
本実施形態に係るイソシアネート基を有するウレタンプレポリマー(以下、「反応性ウレタンプレポリマー」という場合もある。)は、ポリエステルポリオール、ポリエーテルポリオール及びポリブタジエンポリオールを必須とするポリオール成分を、イソシアネート成分と反応させてなり、ウレタンプレポリマーの末端にイソシアネート基を有している。これにより、湿気硬化後に優れた接着性と優れた耐衝撃性を発揮させることができる。
カラム:「Gelpack GLA130−S」、「Gelpack GLA150−S」及び「Gelpack GLA160−S」(日立化成株式会社製、HPLC用充填カラム)
溶離液:テトラヒドロフラン
流量:1.0mL/min
カラム温度:40℃
検出器:RI
本実施形態に係る接着剤組成物は、上記反応性ウレタンプレポリマーと酸化防止剤とを組み合わせて含むことにより、湿気硬化後に優れた接着性と優れた耐衝撃性とを有すると共に、高い信頼性を有することができる。
本実施形態に係る接着剤組成物には、必要に応じて、熱可塑性ポリマー、粘着付与樹脂、触媒、顔料、紫外線吸収剤、界面活性剤、難燃剤、充填剤等を適量配合してもよい。
本実施形態に係る接着剤組成物は、ポリエステルポリオール、ポリエーテルポリオール及びポリブタジエンポリオールを含有するポリオール成分とイソシアネート成分とを反応させて、イソシアネート基を有するウレタンプレポリマーを得る工程を備える方法により製造される。
ポリエステルポリオールとして、ポリエステルポリオールa(アジピン酸及び1,6−ヘキサンジオールを主成分として得られた結晶性ポリエステルポリオール、水酸基数:2、数平均分子量:5000)、ポリエステルポリオールb(アジピン酸及びエチレングリコールを主成分として得られた結晶性ポリエステルポリオール、水酸基数:2、数平均分子量:2000)、ポリエステルポリオールc(イソフタル酸及びネオペンチルグリコールを主成分として得られた非晶性ポリエステルポリオール、水酸基数:2、数平均分子量:2000)、及び、ポリエステルポリオールd(アゼライン酸及びエチレングリコールを主成分として得られた非晶性ポリエステルポリオール、水酸基数:2、数平均分子量:8000)を準備した。ポリエーテルポリオールとして、ポリプロピレングリコール(水酸基数:2、数平均分子量:2000)を準備した。ポリブタジエンポリオールとして、ポリブタジエンポリオールa(水酸基数:2、数平均分子量:1400、構造単位(I)が占める割合:85%、日本曹達株式会社製、商品名「G−1000」)、及び、ポリブタジエンポリオールb(水酸基数:2、数平均分子量:2800、構造単位(I)が占める割合:20%、出光興産株式会社製、商品名「R−45HT」)を準備した。
イソシアネート成分として、ジフェニルメタンジイソシアネート(イソシアネート基数:2)を準備した。
酸化防止剤として、ヒンダードフェノール系酸化防止剤である、SONGWON製の商品名「SONGNOX1076」を準備した。
予め真空乾燥機により脱水処理した、ポリエステルポリオールa10部、ポリエステルポリオールb45部、ポリエステルポリオールc8部、ポリエステルポリオールd3部、ポリプロピレングリコール24部及びポリブタジエンポリオールa10部と、酸化防止剤0.2部とを加えて均一に混合した後、ジフェニルメタンジイソシアネート24部を更に加えて均一に混合した。次いで、得られた混合物を110℃で1時間反応させ、更に110℃で1時間減圧脱泡攪拌し、イソシアネート基を有するウレタンプレポリマーを含む接着剤組成物を得た。
ポリオール成分として、ポリエステルポリオールa10部、ポリエステルポリオールb40部、ポリエステルポリオールc7部、ポリエステルポリオールd3部、ポリプロピレングリコール20部及びポリブタジエンポリオールb20部を用い、ジフェニルメタンジイソシアネートの配合量を22部に変更した以外は、実施例1と同様にして、接着剤組成物を得た。
ポリオール成分として、ポリエステルポリオールa8部、ポリエステルポリオールb33部、ポリエステルポリオールc6部、ポリエステルポリオールd2部、ポリプロピレングリコール16部及びポリブタジエンポリオールa35部を用い、ジフェニルメタンジイソシアネートの配合量を27部に変更した以外は実施例1と同様にして、接着剤組成物を得た。
ポリオール成分として、ポリエステルポリオールa10部、ポリエステルポリオールb40部、ポリエステルポリオールc7部、ポリエステルポリオールd3部、ポリプロピレングリコール20部及びポリブタジエンポリオールa20部を用い、酸化防止剤の配合量を0.1部に変更した以外は実施例1と同様にして、接着剤組成物を得た。
酸化防止剤の配合量を3部に変更した以外は実施例4と同様にして、接着剤組成物を得た。
酸化防止剤の配合量を5部に変更した以外は実施例4と同様にして、接着剤組成物を得た。
ポリオール成分として、ポリエステルポリオールa13部、ポリエステルポリオールb50部、ポリエステルポリオールc9部、ポリエステルポリオールd3部及びポリプロピレングリコール25部を用い、ジフェニルメタンジイソシアネートの配合量を22部に変更した以外は実施例1と同様にして、接着剤組成物を得た。
酸化防止剤を配合しなかった以外は実施例4と同様にして、接着剤組成物を得た。
ポリオール成分として、ポリプロピレングリコール70部及びポリブタジエンポリオールa30部を用い、ジフェニルメタンジイソシアネートの配合量を28部に変更した以外は実施例1と同様にして、接着剤組成物を得た。
ポリオール成分として、ポリエステルポリオールa13部、ポリエステルポリオールb50部、ポリエステルポリオールc9部、ポリエステルポリオールd3部及びポリブタジエンポリオールb25部を用い、ジフェニルメタンジイソシアネートの配合量を21部に変更した以外は実施例1と同様にして、接着剤組成物を得た。
BH−HH型少量回転粘度計(東機産業株式会社製)を用いて下記条件にて接着剤組成物の溶融粘度を測定した。
ローター :4号ローター
試料量 :15g
ローター回転数:50rpm
温度 :120℃
接着剤組成物を100℃に溶融し、温度23℃、湿度50%の環境下において、縦90mm×横75mm×厚さ2mmのポリカーボネート板上に、縦40mm×横25mm×厚さ100μmの接着剤層を形成した後、当該接着剤層の上に、縦250mm×横25mm×厚さ100μmのポリカーボネートフィルムを圧着して試験片を作製した。温度23℃、湿度50%の環境下において7日間静置した後、90°ピール試験(ピール速度:200mm/分)を行い、接着強度(N/25mm)を測定した。
接着剤組成物を100℃に溶融し、温度23℃、湿度50%の環境下で、縦90mm×横75mm×厚さ2mmのポリカーボネート板上に、縦40mm×横25mm×厚さ100μmの接着剤層を形成した後、当該接着剤層の上に、縦250mm×横25mm×厚さ100μmのポリカーボネートフィルムを圧着して試験片を作製した。試験片を温度23℃、湿度50%の環境下において7日間静置した後、温度85℃、湿度85%の高温高湿条件下に7日間静置した。次いで、90°ピール試験(ピール速度:200mm/分)を行い、接着強度(N/25mm)を測定した。
接着剤組成物を100℃に溶融し、縦15mm×横40mm×厚さ100μmの皮膜形状に成形した試験片を作製し、温度23℃、湿度50%の恒温恒湿槽に7日間放置し、その後、オートグラフAGS−X(株式会社島津製作所製)を用いて、接着剤層の引張弾性率(MPa)、破断強度(MPa)、破断伸び(%)をJIS K−7127に準拠して測定した。
接着剤組成物を100℃に溶融し、内径0.25mmの精密ノズル(武蔵エンジニアリング株式会社製、商品名「SHN−0.25N」)を取り付けたシリンジ容器(武蔵エンジニアリング株式会社製、商品名「PSY−30E」)に入れて、100℃に予め加熱されたディスペンサー(武蔵エンジニアリング株式会社製、商品名「SHOTMASTER 200DS」)を用いて溶融した接着剤組成物を吐出して、被着体A(ポリカーボネート板:幅100mm×長さ50mm×厚さ2mm、中心部に内径20mmの穴)上に穴を囲むように40mm×40mmの正方形を描き、被着体B(アクリル板:幅50mm×長さ50mm×厚さ4mm)を貼り合わせ、接着剤層の幅が0.3mm、厚みが0.1mmになるように調節し、被着体Aと接着剤層と被着体Bとがこの順に積層された積層体を作製した。温度23℃、湿度50%の環境下で3日間放置した後、温度23℃、湿度50%の環境下、積層体の被着体B側が下向きとなるように、積層体の被着体A側をデュポン衝撃機(テスター産業株式会社製、商品名「デュポン衝撃試験機」)に固定した。次いで、撃ち型(半径6.25mm)を、積層体の被着体Aの穴から被着体Bの接着剤を塗布した側の表面に上方から接触させるようにして配置した。
Claims (5)
- ポリエステルポリオール、ポリエーテルポリオール及びポリブタジエンポリオールを含有するポリオール成分とイソシアネート成分との反応物である、イソシアネート基を有するウレタンプレポリマーと、酸化防止剤と、を含み、
前記ポリエステルポリオールが、結晶性ポリエステルポリオールと、分子量3000以下の非晶性ポリエステルポリオールと、分子量5000以上の非晶性ポリエステルポリオールとを含む、湿気硬化型反応性ホットメルト接着剤組成物。 - 前記ポリブタジエンポリオールの含有量が、前記ポリオール成分の総量100質量部を基準として5〜45質量部である、請求項1又は2に記載の湿気硬化型反応性ホットメルト接着剤組成物。
- 前記イソシアネート基を有するウレタンプレポリマー100質量部に対して、前記酸化防止剤の含有量が0.05〜5質量部である、請求項1〜3のいずれか一項に記載の湿気硬化型反応性ホットメルト接着剤組成物。
- イソシアネート基を有するウレタンプレポリマーと、酸化防止剤とを含む湿気硬化型反応性ホットメルト接着剤組成物を製造する方法であって、
ポリエステルポリオール、ポリエーテルポリオール及びポリブタジエンポリオールを含有するポリオール成分と、イソシアネート成分とを反応させて、前記イソシアネート基を有するウレタンプレポリマーを得る工程を備え、
前記ポリエステルポリオールが、結晶性ポリエステルポリオールと、分子量3000以下の非晶性ポリエステルポリオールと、分子量5000以上の非晶性ポリエステルポリオールとを含む、方法。
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