JP6275842B2 - ラジカル硬化型接着剤組成物、これを含む偏光板および光学部材 - Google Patents
ラジカル硬化型接着剤組成物、これを含む偏光板および光学部材 Download PDFInfo
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- JP6275842B2 JP6275842B2 JP2016533261A JP2016533261A JP6275842B2 JP 6275842 B2 JP6275842 B2 JP 6275842B2 JP 2016533261 A JP2016533261 A JP 2016533261A JP 2016533261 A JP2016533261 A JP 2016533261A JP 6275842 B2 JP6275842 B2 JP 6275842B2
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Classifications
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Description
本発明者らは、研究を重ねた結果、親水性官能基を有する接着剤組成物に、分子内に3個の(メタ)アクリル基を有するホスフェート系化合物を混合して使用する場合、接着力に優れるだけでなく、耐水性および耐熱性に優れており、ひいては、低粘度の実現が可能であることを見出して、本発明を完成した。
まず、本発明にかかるラジカル硬化型接着剤組成物に含まれる前記(A)分子内に少なくとも1個の親水性官能基を有するラジカル重合性化合物は、接着剤の接着力を実現するための成分で、分子内に少なくとも1個の親水性官能基を有することにより、水素結合による接着力の実現が可能であり、また、ラジカル重合性化合物として、分子内に炭素間不飽和二重結合が存在することにより、ラジカル重合が可能なものであれば特別な制限なく使用が可能である。この時、前記親水性官能基は、ヒドロキシ基、カルボキシ基、ウレタン基、アミン基、アミド基など、水素結合が可能なものであれば特に制限されるものではないが、なかでも特にヒドロキシ基であることが、優れた接着力の実現のためにより好ましい。
次に、本発明にかかるラジカル硬化型接着剤組成物に含まれる前記(B)分子内に3個の(メタ)アクリル基を有するホスフェート系化合物は、接着剤の接着力をより向上させ、ひいては、優れた耐水性および耐熱性を確保するための成分で、分子内に3個の(メタ)アクリル基を含む多様なホスフェート系化合物を使用することができる。
次に、本発明にかかるラジカル硬化型接着剤組成物に含まれる前記(C)ラジカル開始剤は、ラジカル重合性を促進して硬化速度を向上させるためのものである。この時、前記ラジカル開始剤としては、当該技術分野で一般的に使用されるラジカル開始剤が制限なく使用可能であり、例えば、1−ヒドロキシ−シクロヘキシル−フェニル−ケトン(1−Hydroxy−cyclohexyl−phenyl−ketone)、2−ヒドロキシ−2−メチル−1−フェニル−1−プロパノン(2−Hydroxy−2−methyl−1−phenyl−1−propanone)、2−ヒドロキシ−1−[4−(2−ヒドロキシエトキシ)フェニル]−2−メチル−1−プロパノン(2−Hydroxy−1−[4−(2−hydroxyethoxy)phenyl]−2−methyl−1−propanone)、メチルベンゾイルホルメート(Methylbenzoylformate)、オキシ−フェニル−酢酸−2−[2−オキソ−2−フェニル−アセトキシ−エトキシ]−エチルエステル(oxy−phenyl−acetic acid−2−[2oxo−2phenyl−acetoxy−ethoxy]−ethyl ester)、オキシ−フェニル−酢酸−2−[2−ヒドロキシ−エトキシ]−エチルエステル(oxy−phenyl−acetic acid−2−[2−hydroxy−ethoxy]−ethyl ester)、アルファ−ジメトキシ−アルファ−フェニルアセトフェノン(alpha−dimethoxy−alpha−phenylacetophenone)、2−ベンジル−2−(ジメチルアミノ)1−[4−(4−モルホリニル)フェニル]−1−ブタノン(2−Benzyl−2−(dimethylamino)−1−[4−(4−morpholinyl)phenyl]−1−butanone)、2−メチル−1−[4−(メチルチオ)フェニル]−2−(4−モルホリニル)−1−プロパノン(2−Methyl−1−[4−(methylthio)phenyl]−2−(4−morpholinyl)−1−propanone)、ジフェニル(2,4,6−トリメチルベンゾイル)−ホスフィンオキサイド(Diphenyl(2,4,6−trimethylbenzoyl)−phosphine oxide)、フェニルビス(2,4,6−トリメチルベンゾイル)−ホスフィンオキサイド(phenylbis(2,4,6−trimethylbenzoyl)−phosphineoxide)からなるグループより選択された1種以上であってよい。特に、本発明において、フェニルビス(2,4,6−トリメチルベンゾイル)−ホスフィンオキサイド(phenylbis(2,4,6−trimethylbenzoyl)−phosphineoxide)であることが好ましい。
本発明にかかるラジカル硬化型接着剤組成物は、より優れた接着力および耐水性効果を得るために、(D)分子内に1個または2個の(メタ)アクリル基を有するホスフェート系化合物をさらに含むことができる。
本発明にかかるラジカル硬化型接着剤組成物は、より優れた接着力および耐水性効果を得るために、(E)多官能性(メタ)アクリル系化合物をさらに含むものであってもよい。
一方、前記のような本発明のラジカル硬化型接着剤組成物によって形成される接着層の厚さは、0超過10μm以下程度、好ましくは0.1〜10μm、または0.1〜5μm程度であるのが良い。接着層の厚さが0.1μm未満の場合には、接着剤層の均一度および接着力が低下することがあり、接着層の厚さが10μmを超える場合には、薄型化に困難があり、これを含む偏光板などの外観にシワが生じる問題が発生することがある。
まず、本発明にかかる偏光板について説明する。
まず、前記偏光子は特に制限されず、当該技術分野でよく知られている偏光子、例えば、ヨウ素または二色性染料を含むポリビニルアルコール(PVA)からなるフィルムを使用することができる。前記偏光子は、PVAフィルムにヨウ素または二色性染料を染着させて製造できるが、その製造方法は特に限定されない。本明細書において、偏光子は、保護フィルムを含まない状態を意味し、偏光板は、偏光子と保護フィルムとを含む状態を意味する。
次に、前記接着剤層は、上述の本発明にかかるラジカル硬化型接着剤組成物を用いて形成されたものであり、当該技術分野でよく知られている方法によって形成されてよい。例えば、偏光子または保護フィルムの一面に接着剤組成物を塗布して接着剤層を形成した後、偏光子と保護フィルムとを貼り合わせた後、硬化させる方法で行われてよい。この時、前記塗布は、当該技術分野でよく知られている塗布方法、例えば、スピンコーティング、バーコーティング、ロールコーティング、グラビアコーティング、ブレードコーティングなどの方法で行われてよい。
次に、前記保護フィルムは、偏光子を支持および保護するためのものであり、当該技術分野で一般的に知られている多様な材質の保護フィルム、例えば、セルロース系フィルム、ポリエチレンテレフタレート(PET、polyethylene terephthalate)フィルム、シクロオレフィンポリマー(COP、cycloolefin polymer)フィルム、アクリル系フィルムなどが制限なく使用できる。ながでも、光学特性、耐久性、経済性などを考慮する時、アクリル系フィルムを使用することが特に好ましい。
次に、本発明にかかる光学部材について説明する。
まず、本発明に適用できるディスプレイパネルは特に制限されず、例えば、液晶表示装置に使用される多様なモードの液晶パネルが本発明に適用可能である。この時、液晶パネルの具体的な構成は特に制限されず、例えば、上部透明基板/カラーフィルタ/保護膜/透明導電膜電極/配向膜/液晶/配向膜/薄膜トランジスタ/下部透明基板などであってよい。
次に、前記偏光子は、上述のように特に制限されず、当該技術分野でよく知られている偏光子、例えば、ヨウ素または二色性染料を含むポリビニルアルコール(PVA)からなるフィルムを使用することができる。また、上述のように、前記偏光子は、PVAフィルムにヨウ素または二色性染料を染着させて製造できるが、特にこれに限定されるものではない。
次に、前記接着剤層は、上述した本発明のラジカル硬化型接着剤組成物を用いて形成されたものであり、当該技術分野でよく知られているインライン(in−line)工程を通じて形成されてよい。具体的には、例えば、前記接着剤層の形成は、偏光子、または偏光子の一面に保護フィルムが付着した偏光板をロールから巻き出しながら、偏光子の表面に、当該技術分野でよく知られている塗布方法で本発明の前記ラジカル硬化型接着剤組成物を塗布した後、ディスプレイパネルにこれを合紙し、塗布された接着剤組成物層を硬化させる方法で行われてよい。この時、前記硬化は、上述のように光硬化によって行われてよい。本発明の接着剤層は、このようにインライン(in−line)工程を通じて形成できるので、連続的に生産が可能であるなど、生産性に優れる利点がある。
ポリ(N−シクロヘキシルマレイミド−co−メチルメタクリレート)、スチレン−無水マレイン酸共重合体樹脂、およびフェノキシ系樹脂を100:2.5:5の重量比で均一に混合した樹脂組成物を、原料ホッパー(hopper)から押出機までを窒素置換した24φの押出機に供給し、250℃で溶融して、原料ペレット(pellet)を製造した。
(1)接着剤組成物A
HEA(hydroxyethyl acrylate)66.7重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)16.6重量%、tri−(acryloyloxy ethyl)phosphate16.7重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Aを製造した。
HEA(hydroxyethyl acrylate)50重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)21.4重量%、tri−(acryloyloxy ethyl)phosphate14.3重量%、di−(methacryloyloxy ethyl)phosphate14.3重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Bを製造した。
HEA(hydroxyethyl acrylate)50重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)21.4重量%、tri−(acryloyloxy ethyl)phosphate21.4重量%、di−(methacryloyloxy ethyl)phosphate7.2重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Cを製造した。
HEA(hydroxyethyl acrylate)50重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)21.4重量%、tri−(acryloyloxy ethyl)phosphate14.3重量%、DCPDA(Dimethylol tricyclodecane diacrylate)14.3重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Dを製造した。
HEA(hydroxyethyl acrylate)16.7重量%、GLM(glyceryl methacrylate)50重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)16.6重量%、tri−(acryloyloxy ethyl)phosphate16.7重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Eを製造した。
HEA(hydroxyethyl acrylate)50重量%、1,4−cyclohexanedimethanol mono−acrylate16.7重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)16.6重量%、tri−(acryloyloxy ethyl)phosphate16.7重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Fを製造した。
HEA(hydroxyethyl acrylate)50重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)21.4重量%、2−(acrylamido)ethyl bis(2−(acryloyloxy)ethyl)phosphate14.3重量%、DCPDA(Dimethylol tricyclodecane diacrylate)14.3重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Gを製造した。
HEA(hydroxyethyl acrylate)30重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)70重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Hを製造した。
HEA(hydroxyethyl acrylate)66.7重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)16.6重量%、di−(methacryloyloxy ethyl)phosphate16.7重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Iを製造した。
HEA(hydroxyethyl acrylate)66.7重量%、BPA type epoxy di−acrylate(EB600、Cytec製品)16.6重量%、mono−(methacryloyloxy ethyl)phosphate16.7重量%を入れて製造した樹脂組成物100重量部に、ラジカル開始剤のirgacure−819(Ciba社)3重量部を添加して、偏光板用接着剤組成物Jを製造した。
製造例1により製造されたアクリルフィルム系保護フィルムのプライマー層にスポイトで接着剤組成物Aを塗布し、偏光子(PVA素子)の両面に積層した後、最終接着層の厚さが1〜2μmとなるように条件を設定した後、ラミネータ(5m/min)を通過させた。その後、前記アクリルフィルムが積層された面に、UV照射装置(Metal halide lamp)を用いて、1000mJ/cm2の紫外線を照射して、偏光板を製造した。一方、偏光板は、温度20℃、湿度50%の条件で製造した。
接着剤組成物としてBを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてCを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてDを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてEを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてFを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてGを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてHを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてIを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
接着剤組成物としてJを使用した点を除いては、実施例1と同様の方法で偏光板を製造した。
前記実施例および比較例で製造された偏光板の剥離力を測定して、下記の表1に示した。具体的には、前記実施例および比較例で製造された偏光板を、温度20℃、湿度70%の条件で4日放置した後、幅20mm、長さ100mmに裁断し、Texture Analyzer装備(Stable Micro Systems社のTA−XT Plus)で、速度300m/min、90度で、偏光子と保護フィルムの剥離力を測定した。この時、剥離力が2.5N/2cm以上を◎、1.5N/2cm以上2.5N/2cm未満を○、1.0N/2cm以上1.5N/2cm未満をX、1.0N/2cm未満の場合をXXと表示した。
前記実施例および比較例で製造された偏光板の耐水性を測定して、下記の表1に示した。具体的には、前記実施例および比較例の偏光板をガラス基板にラミネーション(glass lamination)した後に、60℃の恒温槽に浸漬させ、8時間経過後、偏光板端部の脱色の有無で耐水性を判断し、変形がない場合を優秀、一部脱色がある場合を良好、脱色が多く生じた場合を劣悪と表示した。
前記実施例および比較例で製造された偏光板の熱衝撃安定性を測定して、下記の表1に示した。具体的には、前記実施例および比較例の偏光板をガラス基板にラミネーション(glass lamination)し、これを−40℃で30分間放置した後、これを再度80℃で30分間放置することを100回繰り返し行った。その後、偏光板の外観に変形があるか否かを肉眼で評価した。偏光板の外観に変形がない場合を優秀、裁断部1mm未満のクラックが発生した場合を良好、1mm以上のクラックが発生した場合を劣悪と表示した。
前記実施例および比較例で使用された接着剤組成物の粘度を、25℃で、Viscometer TV−22(TOKI SANGYO)を用いて測定して、下記の表1に示した。
ガラス基板に接着剤組成物Aを塗布し、偏光子(PVA素子)および上部保護フィルムを積層した後、最終接着層の厚さが1〜2μmとなるように条件を設定した後、ラミネータ(5m/min)を通過させた。その後、前記偏光子および保護フィルムが積層された面に、UV照射装置(Metal halide lamp)を用いて、1000mJ/cm2の紫外線を照射して、ガラス基板に偏光子が付着している光学部材を製造した。一方、光学部材は、温度20℃、湿度50%の条件で製造した。
前記実施例8で製造された偏光板の剥離力を測定して、下記の表3に示した。具体的には、前記実施例8で製造された光学部材を、温度20℃、湿度70%の条件で4日放置した後、幅20mm、長さ100mmに裁断し、Texture Analyzer装備(Stable Micro Systems社のTA−XT Plus)で、速度300m/min、90度で、偏光子とガラス基板の剥離力を測定した。この時、剥離力が2.0N/2cm以上を優秀、1.0N/2cm以上2.0N/2cm未満を良好、1.0N/2cm未満の場合を劣悪と表示した。一方、下記の表2に追加的に記載した剥離力などの測定方法は、上記と同様である。
以上、本発明の実施例について詳細に説明したが、本発明の権利範囲は、これに限定されるものではなく、請求の範囲に記載された本発明の技術的思想を逸脱しない範囲内で多様な修正および変形が可能であることは当技術分野における通常の知識を有する者にとっては自明である。
Claims (14)
- (A)分子内に少なくとも1個の親水性官能基を有するラジカル重合性化合物;
(B)分子内に3個の(メタ)アクリル基を有するホスフェート系化合物;および
(C)ラジカル開始剤を含み、
前記(A)ラジカル重合性化合物は、
(a−1)分子内に少なくとも1個のヒドロキシ基、および少なくとも1個の(メタ)アクリル基を含むラジカル重合性の第1化合物;および
(a−2)分子内に少なくとも2個のヒドロキシ基、少なくとも1個のベンゼン環またはシクロヘキサン環、および少なくとも2個の(メタ)アクリル基を含むラジカル重合性の第2化合物の混合物であり、
前記(a−1)第1化合物は、下記の化学式1〜化学式21からなる群より選択される1種以上であり、
- ラジカル硬化型接着剤組成物100重量部において、(A)ラジカル重合性化合物40〜93重量部;(B)ホスフェート系化合物1〜40重量部;および(C)ラジカル開始剤0.5〜20重量部を含むことを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 前記ラジカル硬化型接着剤組成物は、(D)分子内に1個または2個の(メタ)アクリル基を有するホスフェート系化合物をさらに含むことを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 前記(D)ホスフェート系化合物は、ラジカル硬化型接着剤組成物100重量部において、5〜40重量部で含まれることを特徴とする、請求項4に記載のラジカル硬化型接着剤組成物。
- 前記(D)ホスフェート系化合物は、下記の化学式IIおよび化学式IIIで表される化合物からなる群より選択される1種以上であることを特徴とする、請求項4に記載のラジカル硬化型接着剤組成物。
- 前記ラジカル硬化型接着剤組成物は、化合物(A)、(B)及び(D)とは異なる(E)多官能性(メタ)アクリル系化合物をさらに含むことを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 前記(E)多官能性(メタ)アクリル系化合物は、ラジカル硬化型接着剤組成物100重量部において、5〜40重量部で含まれることを特徴とする、請求項7に記載のラジカル硬化型接着剤組成物。
- 前記(E)多官能性(メタ)アクリル系化合物は、下記の化学式IV〜化学式VIで表される化合物からなる群より選択された1種以上であることを特徴とする、請求項7に記載のラジカル硬化型接着剤組成物。
- 前記ラジカル接着剤組成物によって形成される接着層の厚さは、10μm以下であることを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 前記ラジカル硬化型接着剤組成物は、硬化後のガラス転移温度が50℃以上であることを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 前記ラジカル硬化型接着剤組成物は、粘度が70cP以下であることを特徴とする、請求項1に記載のラジカル硬化型接着剤組成物。
- 偏光子と、
前記偏光子の少なくとも一面に形成される接着剤層と、
前記接着剤層上に形成される偏光子保護フィルムとを含み、
前記接着剤層は、請求項1〜12のいずれか1項に記載のラジカル硬化型接着剤組成物を用いて形成されることを特徴とする、偏光板。 - ディスプレイパネルと、
前記ディスプレイパネルの最外面に接着剤層を介して付着する偏光子とを含み、
前記接着剤層は、請求項1〜12のいずれか1項に記載のラジカル硬化型接着剤組成物を用いて形成されることを特徴とする、光学部材。
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