JP2022549168A - 積層成形用2k pu二重硬化接着剤 - Google Patents
積層成形用2k pu二重硬化接着剤 Download PDFInfo
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- JP2022549168A JP2022549168A JP2022517437A JP2022517437A JP2022549168A JP 2022549168 A JP2022549168 A JP 2022549168A JP 2022517437 A JP2022517437 A JP 2022517437A JP 2022517437 A JP2022517437 A JP 2022517437A JP 2022549168 A JP2022549168 A JP 2022549168A
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- polyol
- thermoplastic
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- acrylate
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Abstract
Description
実施例1
ポリオール1(OH値:540mg KOH/g、平均分子量:240g/mol、混合機能価:2.4、粘度:20℃で300cP)及びポリイソシアネート1(NCO含量:19.0~21.0%、粘度:23℃で2,400~3,600cP)を、1.5:1NCO対OHのNCO:OHモル比をもたらすように量り分けした。ポリイソシアネート及びポリオールを透明のガラス製バイアルに添加し、十分に混合し、続いて発泡が収まるまで約1時間真空脱気した。
NCO:OHモル比が2:1であることを除いて実施例1と同じ成分及び条件。得られた積層体は、剥離力が12~14N/インチであり、許容できる硬化接着性を有した。バルク硬化接着剤は透過性且つゴムのように硬質であった。
NCO:OHモル比が3:1であること以外は実施例1と同じ成分及び条件。得られたTAC/TPE/TAC積層体は、<10N/インチの剥離力を有し、手で剥離可能である。バルク硬化接着剤は透過的且つ軟質であった。1:1以下のNCO:OH比は、TAC及びTPEとの結合に必要な遊離NCO機能基を制限又は排除することが予想される。>3:1のNCO:OH比は、硬化して柔らかいバルク材料となり、過剰な未反応のNCOは経時的に変色し得る。試料が劣った硬化接着性を有し、手で容易に剥離することができ、すなわち一般に<10N/インチであると考えられる状態であったため、剥離強度は測定しなかった。
異なるポリイソシアネート(NCO含量が23.0%、粘度が23℃で2,500cPのポリイソシアネート2)を配合物に用いたことを除いて実施例1と同じ成分及び条件。接着剤のバルク硬化は透過的である。プライマーを積層体に塗布し、円板を打ち抜き、CR39中で注型した。硬化積層体は、積層剥離のない優れた手剥離接着性を示した。レンズ偏光性能は、平均偏光度(DP)=85で良好と格付けされた。
ポリイソシアネート3(NCO含量:21.8、粘度:25℃で2,500cP)を配合物に用いたことを除いて実施例1と同じ成分及び条件。硬化積層体の接着性は劣っており、手で容易にばらばらに剥離された。バルク硬化接着剤は不透明であった。
ポリイソシアネート4(NCO含量:11.9%、粘度:23℃で600cPの脂肪族ポリイソシアネート)を配合物に用いたことを除いて実施例1と同じ成分及び条件。硬化積層体の接着性は劣っており、積層体は手で容易にばらばらに剥離された。バルク硬化接着剤は濁っていた。
ポリイソシアネート5(NCO含量:17~17.6%の脂環式ポリイソシアネートAと、NCO含量:21.8%及び粘度:23℃で3,000cPの脂肪族ポリイソシアネートBと、のブレンド;合計NCO含量:21.0%)を用いたことを除いて実施例1と同じ成分及び条件。硬化積層体の接着性は劣っており、積層体は手で容易にばらばらに剥離された。バルク硬化接着剤は濁っていた。
ポリイソシアネート6(NCO含量:21.8%、粘度:23℃で3,000cP)を用いたことを除いて実施例1と同じ成分及び条件。剥離力は7.5N/インチであり、硬化積層体の接着性は劣っていた。バルク硬化接着剤は濁っていた。
積層成形がスケールアップされ、ロールツーロールラミネータ上を通したことを除いて、実施例4と同じ成分及び条件。ポリオール1(79g)とポリイソシアネート2(236g)とをガラスジャー内で混合してより大きな接着剤バッチを調製した。発泡が収まるまで全ての原料を約30分間真空脱気した。TAC膜(80μm)を45℃の18%腐食剤中で4分間処理し、脱イオン水で3回すすぎ、80℃のオーブンに0.8m/分で通して乾燥させた(約4分)。TPE膜を厚さ約40μmで約4:1に伸張した。
実施例10
ウレタンアクリレート1(ヒドロキシ機能性脂肪族ウレタントリアクリレート、0.50g)及びポリオール1(1.368g)を茶色のガラス製バイアル内に量り分けした。アクリレートモノマー1(ネオペンチルジグリコールジアクリレート、0.110g)及び光開始剤1(0.044g)を添加し、溶解するまで十分に混合した。ポリイソシアネート2(3.632g)を添加し、十分に混合した。発泡が収まるまで溶液を真空脱気した。2ローラーラミネータを用いて、伸張したフォトクロミック-ダイクロイックTPE膜を手動でTACに積層し、続いてFusion内で、各側約22フィート/分で紫外線(H+電球)に曝露した。接着剤を室温で5日間硬化させた。積層体の接着性は許容できるものであった。積層体は透明であり、縞模様の不良は見られず、DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート2(カルボキシ機能性ポリエステルアクリレート)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体の接着性は許容できるものであった。積層体は、いくつかの縞模様の不良が観察されたが透明であり、DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート3(ウレタンジアクリレートオリゴマー)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体の接着性は許容できるものであった。積層体は薄乳白色の濁りを有し、縞模様の不良が観察された。DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート4(脂肪族ウレタンジアクリレートオリゴマー)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体の接着性は許容できるものであった。積層体は乳白色の濁りを有し、縞模様の不良は観察されなかった。DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート5(脂肪族ポリエステル系ウレタンジアクリレートオリゴマー)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体の接着性は許容できるものであった。積層体は透明であり、縞模様の不良は見られなかった。DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート6(ウレタンジアクリレートオリゴマー)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体の接着性は許容できるものであった。積層体は透明であり、縞模様の不良は見られなかった。DPは良好であった。
ウレタンアクリレート1をウレタンアクリレート7(ウレタンジアクリレートオリゴマー)に置き換えたことを除いて実施例10と同じ成分及び条件。積層体は不透明であった。
アクリレートモノマー1の量を0.50gに減らし、光開始剤1の量を0.0165gに減らしたことを除いて実施例14と同じ成分及び条件。積層体の接着性は良好であり、縞模様の不良は観察されなかった。
二重硬化接着剤をロールツーロールラミネータ上で用いたことを除いて実施例10と同じ成分及び条件。アクリレートモノマー1(4g)、ポリオール1(46.4g)、ウレタンアクリレート1(20g)、及び光開始剤1(1.68g)を茶色のガラス瓶に量り分けし、溶解するまで混合した。ポリイソシアネート2(133.6g)を添加し、十分に混合した。発泡が収まるまで全ての原料を約30分間真空脱気した。
実施例10と同じ成分及び条件。ウレタンアクリレート1(0.50g)及びポリオール1(1.130g)を、茶色のガラスバイアル内に量り分けした。アクリレートモノマー1(0.10)及び光開始剤1(0.042g)を添加し、溶解するまで十分に混合した。ポリイソシアネート2(3.371)を添加し、十分に混合した。発泡が収まるまで溶液を真空脱気した。2ローラーラミネータを用いて、PhCh TPU膜を手動でTACに積層し、続いてFusion内で、各側約24フィート/分で、一側面あたり2回の曝露を紫外線(H+電球)に曝露した(2回実施)。接着剤を室温で5日間硬化させた。積層体は黄色であった。
光開始剤1を等モル量の光開始剤2(0.034g)に置き換えたことを除いて実施例19と同じ成分及び条件。積層体は、実施例19よりも淡い黄色を示した。
光開始剤1を等モル量の光開始剤3(0.016g)に置き換えたことを除いて実施例19と同じ成分及び条件。積層体は無色であった。
光開始剤1を等モル量の光開始剤4(0.026g)に置き換えたことを除いて実施例19と同じ成分及び条件。積層体は無色であった。
Claims (15)
- 機能化光学物品であって、
少なくとも1つの重合モノマー又は熱可塑性材料を備える光学レンズと、
機能性膜、前記機能性膜の一方の側に位置決めされた第1の熱可塑性膜、及び前記機能性膜の反対側に位置決めされた第2の熱可塑性膜を備える機能性多層積層体と、
前記機能性膜と前記第1及び第2の熱可塑性膜のそれぞれとの間に配設される積層用接着剤と、を備え、
前記接着剤が、硬化前に、
少なくとも1つのポリイソシアネート、
少なくとも1つのポリオール、及び
任意選択的に触媒からなる、機能化光学物品。 - 前記少なくとも1つのポリオールが少なくとも2の機能価を有する、請求項1に記載の光学物品。
- 前記少なくとも1つのポリオールが、ポリエステルポリオール、ポリエーテルポリオール、アミド基を含有するポリオール、ポリアクリレートポリオール、エポキシポリオール、ポリビニルポリオール、ウレタンポリオール、又は2つ以上のこうしたポリオールの混合物である、請求項1に記載の光学物品。
- 前記第1の熱可塑性膜及び前記第2の熱可塑性膜のそれぞれが、独立してセルローストリアセテート、ポリカーボネート、ポリメタクリレート、ポリアミド、及びポリスチレンからなる群から選択される材料を備える、請求項1に記載の光学物品。
- 前記機能性膜が、延伸熱可塑性エラストマー膜、非延伸熱可塑性エラストマー膜、延伸熱可塑性ウレタン膜、及び非延伸熱可塑性ウレタン膜からなる群から選択される、請求項1に記載の光学物品。
- 前記機能性膜が、フォトクロミック材料、ダイクロイック材料、フォトクロミック-ダイクロイック材料、又はこれらの組み合わせを更に備える、請求項1に記載の光学物品。
- 機能化光学物品であって、
少なくとも1つの重合モノマー又は熱可塑性材料を備える光学レンズと、
機能性膜、前記機能性膜の一方の側に位置決めされた第1の熱可塑性膜、及び前記機能性膜の反対側に位置決めされた第2の熱可塑性膜を備える機能性多層積層体と、
前記機能性膜と前記第1及び第2の熱可塑性膜のそれぞれとの間に配設される積層用接着剤と、を備え、
前記接着剤が、硬化前に、
少なくとも1つのポリイソシアネート、
少なくとも1つのポリオール、
少なくとも1つの重合開始剤、
少なくとも1つの脂肪族ウレタンアクリレート、及び
少なくとも1つのアクリレートモノマーを備え、
前記接着剤が任意選択的に触媒を備える、機能化光学物品。 - 前記脂肪族ウレタンアクリレートが少なくとも2の機能価を有する、請求項7に記載の光学物品。
- 前記脂肪族ウレタンアクリレートはヒドロキシ機能化アクリレートである、請求項7に記載の光学物品。
- 前記少なくとも1つのポリオールが少なくとも2の機能価を有する、請求項7に記載の光学物品。
- 前記少なくとも1つのポリオールが、ポリエステルポリオール、ポリエーテルポリオール、アミド基を含有するポリオール、ポリアクリレートポリオール、エポキシポリオール、ポリビニルポリオール、ウレタンポリオール、又は2つ以上のこうしたポリオールの混合物である、請求項7に記載の光学物品。
- 前記少なくとも1つのアクリレートモノマーが、2-フェノキシエチルアクリレート、ベンジルメタクリレート、イソボルニルアクリレート、ネオペンチルグリコールジアクリレート、及び1,3-ブチレングリコールジメタクリレートからなる群から選択される、請求項7に記載の光学物品。
- 前記第1の熱可塑性膜及び前記第2の熱可塑性膜のそれぞれが、独立してセルローストリアセテート、ポリカーボネート、ポリメタクリレート、ポリアミド、ナイロン、及びポリスチレンからなる群から選択される材料を備える、請求項7に記載の光学物品。
- 前記機能性膜が、延伸熱可塑性エラストマー膜、非延伸熱可塑性エラストマー膜、延伸熱可塑性ウレタン膜、及び非延伸熱可塑性ウレタン膜からなる群から選択される、請求項7に記載の光学物品。
- 前記機能性膜が、フォトクロミック材料、ダイクロイック材料、フォトクロミック-ダイクロイック材料、又はこれらの組み合わせを更に備える、請求項7に記載の光学物品。
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PCT/EP2020/076012 WO2021053089A1 (en) | 2019-09-19 | 2020-09-17 | 2k pu-dual cure adhesive for lamination |
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CA1235641A (en) * | 1983-02-17 | 1988-04-26 | Edward J. Sare | Laminated ophthalmic lens and method of preparing same |
US7465414B2 (en) * | 2002-11-14 | 2008-12-16 | Transitions Optical, Inc. | Photochromic article |
US7256921B2 (en) | 2003-07-01 | 2007-08-14 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
JP5034390B2 (ja) * | 2006-09-11 | 2012-09-26 | 大日本印刷株式会社 | Pva偏光板用接着剤 |
DE102008036685A1 (de) * | 2008-08-06 | 2010-02-11 | Basf Coatings Ag | Zweischicht-Beschichtungssysteme mit verbesserter Zwischenhaftung |
US9132594B2 (en) * | 2008-11-04 | 2015-09-15 | Essilor International (Compagnie Générale d'Optique) | Bi-layer adhesive for lens lamination |
JP5011444B2 (ja) * | 2010-09-03 | 2012-08-29 | 日東電工株式会社 | 粘着型光学フィルム、その製造方法および画像表示装置 |
EP2976370B1 (en) * | 2013-03-20 | 2021-03-10 | Essilor International | Polyurethane based adhesive for polarizing structure and polarized lens |
JP6346183B2 (ja) * | 2013-08-02 | 2018-06-20 | 株式会社トクヤマ | 光学物品用光硬化性プライマー組成物の硬化体を含むフォトクロミック積層体及び該積層体の製造方法 |
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