JP2018527420A - 紫外線吸収基を含むコポリマー及びそれを含む組成物 - Google Patents
紫外線吸収基を含むコポリマー及びそれを含む組成物 Download PDFInfo
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- JP2018527420A JP2018527420A JP2017566759A JP2017566759A JP2018527420A JP 2018527420 A JP2018527420 A JP 2018527420A JP 2017566759 A JP2017566759 A JP 2017566759A JP 2017566759 A JP2017566759 A JP 2017566759A JP 2018527420 A JP2018527420 A JP 2018527420A
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Abstract
Description
本出願は、2015年6月25日に出願された米国特許仮出願第62/184,784号の優先権を主張するものであり、その全容が参照により本明細書に組み込まれる。
紫外線(UV)に曝露される材料中に、紫外線吸収剤(UVA)を組み込むことは、例えば紫外線による劣化から材料を保護する点において望ましい場合がある。いくつかのUVAは組成物に分散させることもできるが、場合によっては、蒸発や表面へのマイグレーションによってそれらが失われてしまうことがある。UVAを感圧接着剤(PSA)に共有結合的に組み込むことが提案されてきた(2012年10月4日発行の特開2012−188620号を参照)。PSA組成物に含有させるための、UV吸収基を有するモノマーから作製された特定のコポリマーが記述されてきた(2000年4月28日発行の特開2000−123621号を参照)。
「a」、「an」、及び「the」などの用語は、単数の実体のみを指すことを意図するものではなく、具体例を例示のために用いることができる一般部類を含む。用語「a」、「an」、及び「the」は、用語「少なくとも1つの」と互換的に使用される。
第1の実施形態において、本開示は、コポリマーであって、
ペンダント紫外線吸収基を含む第1の2価の単位、
式
式
各R1は、独立して、水素又はメチル基であり、
R2は、1〜20個の炭素原子を有する直鎖又は分枝鎖のアルキル基であり、
Vは、O又はNHであり、
Wは、1〜10個の炭素原子を有するアルキレン基であり、
各R’は、独立して、1〜6個の炭素原子を有するアルキル基である。]で表される第3の2価の単位、を含む、コポリマーを提供する。
R1は、独立して、水素又はメチル基であり、
Vは、O又はNHであり、
Xは結合、アルキレン基、又はアルキレンオキシ基であり、ここで、前記アルキレン基又はアルキレンオキシ基は、1〜10個の炭素原子を有し、任意に1個以上の−O−基が介在しており、任意にヒドロキシル基によって置換されており、
Rは、1〜4個の炭素原子を有するアルキル基であり、
nは、0又は1であり、
Zは、ベンゾイル基(任意にヒドロキシル基、アルキル基、ハロゲン、又はヒドロキシル基で置換されている。)、4,6−ビスフェニル[1,3,5]トリアジン−2−イル基(各フェニル基が任意に独立して1個以上のアルキル基又はアルコキシ基で置換されている。)、又は、2H−ベンゾトリアゾール−2−イル基(任意に1個以上のハロゲンで置換されている。)である。]で表される、第1又は第2の実施形態に記載のコポリマーを提供する。
第1の表面、及び第1の表面の反対側の第2の表面を有する、第1のポリマーフィルム基材、
第1のポリマーフィルムの第1の表面に配置されたバリアフィルム、
第1の表面、及び第1の表面の反対側の第2の表面を有する感圧接着剤層であって、感圧接着剤層の第1の表面が、第1のポリマーフィルム基材の反対側のバリアフィルム上に配置されており、感圧接着剤組成物が、第9〜16の実施形態のいずれか1つに記載の組成物を含む、感圧接着剤層、並びに
感圧接着剤層の第2の表面に配置された第2のポリマーフィルム基材、を含む、アセンブリを提供する。
別段の記載がない限り、実施例及び明細書の残りの部分における、全ての部分、パーセンテージ、比などは全て重量によるものであり、実施例で使用された全ての試薬は、例えば、Alfa Aesar(Ward Hill,Mass)のような一般的な化学物質供給元から入手した。
分子量の決定
下記のオリゴマーの実施例では、分子量は、ゲル浸透クロマトグラフィー(GPC)を使用して標準直鎖型ポリスチレンポリマーとの比較によって求めた。GPC測定は、Waters Reliant e2695システム(Waters Corporation(Milford,MA)より入手)において、300ミリメートル(mm)×7.5mmのリニアPL−Gel−2カラムを2本(3マイクロメートルMixed−E(最大30000ダルトンの公称MW範囲のもの)が1本、及び5マイクロメートルMixed−D(200〜400000ダルトンの公称MW範囲のもの)が1本)を使用して実施した。検出は、Waters Model 2414 蒸発光散乱検出器を用いて行った(ドリフトチューブ:70℃、窒素流は30psi、ネビュライザ温度は30℃)。50ミリグラム(mg)のオリゴマーのサンプルを10ミリリットル(mL)のテトラヒドロフラン(250ppmのBHTで安定化)に溶解し、0.45マイクロメートルのシリンジフィルターを通して濾過した。30マイクロリットルのサンプルをカラムに注入し、カラム温度は40℃であった。流量は1mL/分であり、移動相はテトラヒドロフランであった。分子量較正は、ピーク平均分子量が4.8×105g/mole〜580gram/moleの、分布の狭いポリスチレン標準を使用して行った。較正と分子量の算出は、好適なGPCソフトウェアを用い、分子量較正曲線に対して3次の多項式近似を用いて行った。各報告値は、2回の注入の平均である。
ヘイズ(曇り)測定は、ASTM D1003−13(2013年11月)に従って、BTK HAZE GUARD PLUSヘイズメーター(BYK−Gardner USA,Columbia,MD)を使用して実施した。
フィルムをASTM G155に規定されているように日光フィルターを使用して、連続的にキセノンアークの放射に曝した。放射照度は340nmにおいて1.3W/m2/nmとした。ブラックパネル温度を70℃に設定し、チャンバ温度は47℃に設定した。相対湿度は30%に設定した。水噴霧は使用しなかった。サンプルは、これらの加速耐侯試験条件に少しでも曝露される前と約662MJ/m2のUV総照射量において評価した。
2Lの三ツ口丸底フラスコに温度プローブ、冷却器、及び機械式攪拌機を取り付けた。このフラスコに、4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)ベンゼン−1,3−ジオール(400g(1.17モル))、エチレンカーボネート(115.5g(1.31モル))、テトラエチルアンモニウムブロマイド(16.7g(0.085モル))、及びジメチルホルムアミド(DMF)(440g)、を投入した。このバッチを150℃まで加熱し、この温度に5時間保った。バッチからCO2が発生するのが観察された。5時間後、追加のエチレンカーボネート(10g)を加えた。このバッチを150℃で3時間加熱し、更にエチレンカーボネート(15g)及びテトラエチルアンモニウムブロマイド(2g)を追加した。このバッチを150℃で更に3時間加熱した。この後には、出発原料は薄膜クロマトグラフィーで観察されなくなった。
2Lの三ツ口丸底フラスコに温度プローブ、冷却器を備えたディーン−スタークトラップ、及び機械式攪拌機を取り付けた。このフラスコに、パートAで調製した2−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−5−(2−ヒドロキシエトキシ)フェノール(150g(0.389モル))、トルエン(790g)、4−メトキシフェノール(MEHQ)開始剤(0.24g)、フェノチアジン阻害剤(0.38g)、p−トルエンスルホン酸(8.5g)、及びアクリル酸(30.8g(0.43モル))、を投入した。このバッチを、還流(約115℃)で中程度の攪拌をしながら6時間加熱し、共沸した水をディーン−スタークトラップで集めた。5時間後、追加のアクリル酸(5g)を添加し、このバッチを更に3時間加熱した。50/50のエチルアセテート/ヘキサンで展開する薄膜クロマトグラフィーを用いた分析を行ったところ、バッチ中には残存出発原料はないことが示された。
IOA(8g)を、0.5パイント(約240mL)の瓶中で、調製例1(1g)、BTZ−MA(1g)、VAZO67(0.05g)、及びEtOAc(30g)と混合した。瓶の内容物を窒素で1分間パージし、次に瓶をキャップとテープとで封止した。次いで、瓶をラウンダーオメーター内に入れて、65℃で20時間攪拌した。
IOE−1と同じ重合条件を用いて、下記表2に列挙された材料と量とに従って、IOA(70重量%)、調製例1(10重量%)、BTZ−MA(10重量%)、及び追加のモノマー(10重量%)のランダムコポリマーとして、実施例1及び例示的オリゴマー実施例2〜4を調製した。
「PSA中のUVA」サンプルを得るために、実施例1及びIOE−1〜IOE−4の溶液を各々、45重量%のイソオクチルアクリレート/アクリル酸(94:6)を含む溶剤系感圧接着剤(PSA)組成物中にブレンドした。この感圧接着剤組成物は、米国再発行特許第24906号に記載されているとおりに調製した。組成物中4%の活性UVAを目標とした。
追加のオリゴマー実施例を、実施例1と同様の重合手順を使用し、DEAEMAを追加のモノマーとして含む、下表4に示した材料と量とを使用して、調製した。
オリゴマー実施例3〜10のサンプルを、上記の実施例2の調製と同様の手法を用いてPSA中にブレンドし、これらの「PSA中のUVA」実施例11〜18を、目視で曇り、及び/又は濁りを検査した。これらの結果を表6にまとめた。組成物中、4%又は10%のいずれかの活性UVAを目標とした。実施例11では、16%の活性UVAを加えた。
追加の例示的オリゴマー実施例を、実施例1と同様の重合手順を使用し、DMAAを追加のモノマーとして含む、下表7に示した材料と量とを使用して、調製した。
いくつかの例示的実施例について、IOE−5〜IOE−9のサンプルを、上記の実施例2の調製と同様の手法を用いてPSA中にブレンドし、これらの「PSA中のUVA」例示的実施例について、目視で曇り、及び/又は濁りを検査した。これらの結果を表8にまとめた。組成物中4%の活性UVAを目標とした。
PSA中のUVAサンプルは以下のようにして調製した。UVA材料及び「TINUVIN123」をトルエンに溶解した後、透明なガラス瓶中の実施例2に記載したPSA組成物に加えた。この際、表9に記載した材料の相対重量%を使用した。混合物は100gのバッチとして作製され、40rpmで10分間、回転させて混ぜ合わせた。米国特許第6,777,079号(Zhouら)に記載されている種類のビスーアミド架橋剤(PSAと架橋剤の重量を基に0.2重量%)を、この混合物に添加し、混合物を40rpmで更に20分間回転させた。UVAの重量%は活性UVAの重量%である。
表9のサンプルの記述に従ってサンプルを調製した。ただし、実施例19及び20、並びに比較例Eの活性UVAの%を1%、比較例Fの活性UVAの%を2%に変更した。これらの重ね合わせたサンプルを、上記の加速紫外線曝露試験法に従って試験した。この耐侯試験中に定期的に吸収度測定を実施し、350nmでの吸収ピークをUV照射量に対して測定した。光照射量に対する350nmでの吸収率の関係から傾きを求め、その結果を表11にまとめた。
Claims (15)
- 前記ペンダント紫外線吸収基がトリアジン、ベンゾフェノン、又はベンゾトリアゾールを含む、請求項1に記載のコポリマー。
- 各第1の2価の単位が、独立して、式
Vは、O又はNHであり、
Xは結合、アルキレン基、又はアルキレンオキシ基であり(ここで、前記アルキレン基又はアルキレンオキシ基は、1〜10個の炭素原子を有し、任意に1個以上の−O−基が介在しており、任意にヒドロキシル基によって置換されている。)、
Rは、1〜4個の炭素原子を有するアルキル基であり、
nは、0又は1であり、
Zは、ベンゾイル基(ヒドロキシル基、アルキル基、ハロゲン、又はヒドロキシル基で任意に置換されている。)、4,6−ビスフェニル[1,3,5]トリアジン−2−イル基(各フェニル基が1個以上のアルキル基又はアルコキシ基で任意に独立して置換されている。)、又は、2H−ベンゾトリアゾール−2−イル基(1個以上のハロゲンで任意に置換されている。)である。]で表される、請求項2に記載のコポリマー。 - 前記コポリマー中の前記第1の2価の単位の少なくともいくつかが、異なるZ基を含む、請求項3に記載のコポリマー。
- 前記第3の2価の単位が、前記コポリマーの総重量に基づいて、少なくとも1重量%の量で前記コポリマー中に存在する、請求項1〜3のいずれか一項に記載のコポリマー。
- R2が、4〜20個の炭素原子を有する、直鎖又は分枝鎖のアルキル基である、請求項1〜5のいずれか一項に記載のコポリマー。
- 感圧接着剤と、請求項6に記載のコポリマーとの、ブレンドを含む組成物。
- 前記感圧接着剤が、前記第2の2価の単位を含むアクリル感圧接着剤である、請求項7に記載の組成物。
- 前記感圧接着剤が、ペンダントカルボン酸基を含む第4の2価の単位、を更に含む、請求項8に記載の組成物。
- 前記コポリマーの数平均分子量が、前記感圧接着剤の数平均分子量の半分以下である、請求項7〜9のいずれか一項に記載の組成物。
- 前記コポリマーが、前記組成物の総重量に基づいて、0.5重量%〜25重量%の範囲の量で前記組成物中に存在する、請求項7〜10のいずれか一項に記載の組成物。
- 前記組成物が、前記第1、第2、及び第3の2価の単位を前記ブレンド中に含む、第2の異なるコポリマーを含み、前記第1の2価の単位が、前記コポリマー中、及び前記第2の異なるコポリマー中に、異なるペンダント紫外線吸収基を含む、請求項7〜11のいずれか一項に記載の組成物。
- 請求項7〜12のいずれか一項に記載の組成物を含む物品であって、前記組成物が前記物品の少なくとも表面に配置されており、前記物品が、光起電力デバイス、車両用ラッピングフィルム、グラフィックスフィルム、落書き防止フィルム、建造物用フィルム、又は窓用フィルムである、物品。
- アセンブリであって、
第1の表面、及び前記第1の表面の反対側の第2の表面を有する、第1のポリマーフィルム基材、
前記第1のポリマーフィルム基材の前記第1の表面上に配置されたバリアフィルム、
第1の表面、及び前記第1の表面の反対側の第2の表面を有する感圧接着剤層であって、前記感圧接着剤層の前記第1の表面が、前記第1のポリマーフィルム基材の反対側の前記バリアフィルム上に配置されており、前記感圧接着剤組成物が、請求項7〜12のいずれか一項に記載の組成物を含む、感圧接着剤層、並びに
前記感圧接着剤層の前記第2の表面上に配置された第2のポリマーフィルム基材、
を含む、アセンブリ。 - 前記アセンブリが、光起電力電池上に配置されている、請求項14に記載のアセンブリ。
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EP3313906B1 (en) | 2020-08-05 |
JP6940418B2 (ja) | 2021-09-29 |
CN107709385B (zh) | 2020-06-12 |
KR20180021094A (ko) | 2018-02-28 |
EP3313906A4 (en) | 2019-03-13 |
CN107709385A (zh) | 2018-02-16 |
US10519350B2 (en) | 2019-12-31 |
WO2016210140A1 (en) | 2016-12-29 |
EP3313906A1 (en) | 2018-05-02 |
US20180187053A1 (en) | 2018-07-05 |
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