JP6291926B2 - 活性エネルギー線重合性樹脂組成物及び積層体 - Google Patents
活性エネルギー線重合性樹脂組成物及び積層体 Download PDFInfo
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- JP6291926B2 JP6291926B2 JP2014049673A JP2014049673A JP6291926B2 JP 6291926 B2 JP6291926 B2 JP 6291926B2 JP 2014049673 A JP2014049673 A JP 2014049673A JP 2014049673 A JP2014049673 A JP 2014049673A JP 6291926 B2 JP6291926 B2 JP 6291926B2
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- 229910052708 sodium Inorganic materials 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- XMRZNNGTCUALQE-UHFFFAOYSA-N tert-butyl 3-(4-ethenylphenoxy)propanoate Chemical compound CC(C)(C)OC(=O)CCOC1=CC=C(C=C)C=C1 XMRZNNGTCUALQE-UHFFFAOYSA-N 0.000 description 1
- YQPZJBVEKZISEF-UHFFFAOYSA-N tetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YQPZJBVEKZISEF-UHFFFAOYSA-N 0.000 description 1
- NPWJBNPQTPEEGC-UHFFFAOYSA-N tetradecyl 4-ethenylbenzoate Chemical compound C(CCCCCCCCCCCCC)OC(C1=CC=C(C=C1)C=C)=O NPWJBNPQTPEEGC-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- NELVVTIEGZVCKM-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CCCNC(=O)C=C.C[N+](C)(C)CCCNC(=O)C=C NELVVTIEGZVCKM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CIBGZAYGXFGOFK-UHFFFAOYSA-L zinc;2-phenylethenesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C=CC1=CC=CC=C1.[O-]S(=O)(=O)C=CC1=CC=CC=C1 CIBGZAYGXFGOFK-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polarising Elements (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
高温環境下では接着性が弱いとPVA系偏光子と保護フィルムの熱収縮率の違いにより、PVA系偏光子と保護フィルムとが剥がれる問題が発生することがあるが、前記カチオン重合性紫外線硬化型接着剤により形成した偏光板では過酷な環境下における耐久性を満足することはできていなかった。
活性エネルギー線カチオン重合開始剤(B)とを必須成分とする活性エネルギー重合性樹脂組成物であって、下記(1)〜(3)を特徴とする活性エネルギー重合性樹脂組成物に関する。
(1)化合物(A)が、化合物(A−1)〜(A−8)から選択される1以上の化合物を含有する。
化合物(A−1):分子内に1個以上の脂肪族へテロ環構造を有するα,β−不飽和二重結合基含有化合物
化合物(A−2):分子内に1個以上のビニル基を有するα,β−不飽和二重結合基含有化合物(ただし、ビニル基はα,β−不飽和二重結合基以外に有する官能基とし、アクリロイル骨格由来のビニル基は除く)
化合物(A−3):分子内に1個以上のケトン基を有するα,β−不飽和二重結合基含有化合物(ただし、アクリロイル基由来のカルボニル基を除く)
化合物(A−4):分子内に1個以上のカルボキシ基を有するα,β−不飽和二重結合基含有化合物
化合物(A−5):分子内に1個以上のヒドロキシ基を有するα,β−不飽和二重結合基含有化合物
化合物(A−6):分子内に1個以上のアミノ基を有するα,β−不飽和二重結合基含有化合物(ただし酸アミド由来のアミノ基を除く)
化合物(A−7):分子内に1個以上のアルキロールアミド基を有するα,β−不飽和二重結合基含有化合物
化合物(A−8):分子内に1個以上のアルコキシシリル基を有するα,β−不飽和二重結合基含有化合物
(2)化合物(A)100重量部に対して、活性エネルギー線カチオン重合開始剤(B)を1〜10重量部含む。
(3)活性エネルギー線ラジカル重合開始剤(ただしカチオン重合開始剤(B)である場合を除く)を含まない。
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−1)および化合物(A−2)の合計が10〜80重量部である上記活性エネルギー重合性樹脂組成物に関する。
化合物(A−5)および/または化合物(A−6)と、
化合物(A−4)とを含有する場合において、
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−5)と、化合物(A−6)と、化合物(A−4)との合計が10〜80重量部である上記活性エネルギー重合性樹脂組成物に関する。
化合物(A−3)と、
化合物(A−5)とを含有する場合において、
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−3)および化合物(A−5)の合計が10〜80重量部である上記活性エネルギー重合性樹脂組成物に関する。
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−7)が10〜80重量部である上記活性エネルギー重合性樹脂組成物に関する。
化合物(A−1)および/または化合物(A−2)と、
化合物(A−3)または化合物(A−4)と、
化合物(A−5)または化合物(A−6)とを含有することを特徴とする上記活性エネルギー重合性樹脂組成物に関する。
化合物(A−1)および/または化合物(A−2)と、
化合物(A−7)とを含有することを特徴とする上記活性エネルギー重合性樹脂組成物に関する。
130<(M)<500
の範囲であることを特徴とする上記活性エネルギー重合性樹脂組成物に関する。
該基材(G)の少なくとも一方の主面に設けられた上記活性エネルギー重合性樹脂組成物からなる樹脂層とを有する積層体に関する。
該光学フィルムの少なくとも一方の主面に設けられた上記樹脂組成物からなる樹脂層とを有する光学素子用積層体に関する。
<活性エネルギー線重合性樹脂組成物>
本発明の活性エネルギー線重合性組成物はα,β−不飽和二重結合基含有化合物(A)と、
活性エネルギー線カチオン重合開始剤(B)とを必須成分とする活性エネルギー重合性樹脂組成物であって、下記(1)〜(3)を特徴とする活性エネルギー重合性樹脂組成物である。
(1)化合物(A)が、化合物(A−1)〜(A−8)から選択される1以上の化合物を含有する。
化合物(A−1):分子内に1個以上のヘテロ環状構造を有するα,β−不飽和二重結合基含有化合物
化合物(A−2):分子内に1個以上のビニル基を有するα,β−不飽和二重結合基含有化合物(ただし、ビニル基はα,β−不飽和二重結合基以外に有する官能基とし、アクリロイル骨格由来のビニル基は除く)
化合物(A−3):分子内に1個以上のケトン基を有するα,β−不飽和二重結合基含有化合物(ただし、アクリロイル基由来のカルボニル基を除く)
化合物(A−4):分子内に1個以上のカルボキシ基を有するα,β−不飽和二重結合基含有化合物
化合物(A−5):分子内に1個以上のヒドロキシ基を有するα,β−不飽和二重結合基含有化合物
化合物(A−6):分子内に1個以上のアミノ基を有するα,β−不飽和二重結合基含有化合物(ただし酸アミド由来のアミノ基を除く)
化合物(A−7):分子内に1個以上のメチロールアミド基を有するα,β−不飽和二重結合基含有化合物
化合物(A−8):分子内に1個以上のアルコキシシリル基を有するα,β−不飽和二重結合基含有化合物
(2)化合物(A)100重量部に対して、活性エネルギー線カチオン重合開始剤(B)を1〜10重量部含む。
(3)は、光ラジカル重合開始剤を含まない。
α,β−エチレン性不飽和二重結合基含有化合物(A):
本発明に用いられるα,β−エチレン性不飽和二重結合基含有化合物(A)は、1個以上のα,β−不飽和二重結合基を含有する化合物であれば、特に制限なく使用できるが、活性エネルギー線カチオン重合開始剤により反応促進される官能基を有する(A−1)〜(A−8)を含有することが好ましい。
例えば、1−ビニル−2−イミダゾリン、1−ビニル−2−メチル−2−イミダゾリン、2−ビニル−2−イミダゾリン、N−ビニル−2−ピロリドン、N−ビニル−ε−カプロラクタム、1−(メタ)アリルピペラジン、2−ビニルピペラジン、4−ビニルピペラジン、1−ベンジル−2−ビニルピペラジン、1−ベンジル−3−ビニルピペラジン、1、4−ジメチル−3−ビニルピペラジン等の窒素原子含有の脂肪族ヘテロ環を有するビニル基含有化合物類;
例えば、4−アクリロイルモルホリン、N−[2−(1H−イミダゾール−5−イル)エチル] (メタ)アクリルアミド、N−(オキセタン−3−イルメトキシメチル)(メタ)アクリルアミド、N−(オキセタン−2−イルメトキシメチル)(メタ)アクリルアミド等の脂肪族ヘテロ環を有するアクリルアミド類;
例えば、コハク酸ビニルフェニルポリ(エチレンオキサイド)、ヘキサヒドロフタル酸ビニルフェニルメチルポリ(エチレンオキサイド)、テレフタル酸ビニルフェニルエチルポリ(エチレンオキサイド)、マレインアミドなどの不飽和ジカルボン酸誘導体類;
例えば、N−ヒドロキシエチル(メタ)アクリルアミド〔N−ヒドロキシエチルアクリルアミドとN−ヒドロキシエチルメタクリルアミドとを併せて「N−ヒドロキシエチル(メタ)アクリルアミド」と表記する。以下同様。〕、N−ヒドロキシプロピル(メタ)アクリルアミド、N−ヒドロキシブチル(メタ)アクリルアミド、N−ヒドロキシヘキシル(メタ)アクリルアミド、N−ヒドロキシオクチル(メタ)アクリルアミド等の水酸基含有の(メタ)アクリルアミド類;
例えば、3−ヒドロキシプロピルビニルエーテル、4−ヒドロキシブチルビニルエーテル、5−ヒドロキシペンチルビニルエーテル、6−ヒドロキシヘキシルビニルエーテルなどの脂肪族ビニルエーテル類;
例えば、(メタ)アクリル酸をポリエチレングリコールで脱水縮合して得られる(メタ)アクリル酸−ポリエチレングリコール類;
例えば、4−ビニル安息香酸メチルポリ(エチレンオキサイド)、4−ビニル安息香酸エチルポリ(エチレンオキサイド)、4−イソプロペニル安息香酸メチルポリ(プロピレンオキサイド)、4−イソプロペニル安息香酸エチルポリ(プロピレンオキサイド)などのポリアルキレンオキサイド部位を有するビニル安息香酸エステル系系単量体類等が挙げられるが、特にこれらに限定されるものではない。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
(1)化合物(A−1)
(2)化合物(A−2)
(3)化合物(A−1)と、化合物(A−2)との組合せ
(4)化合物(A−5)と、化合物(A−4)との組合せ
(5)化合物(A−6)と、化合物(A−4)との組合せ
(6)化合物(A−3)と、化合物(A−5)との組合せ
(7)化合物(A−7)
また、80重量部を超える場合、活性エネルギー線硬化樹脂組成物の架橋密度が高くなり過ぎてしまい、活性エネルギー線硬化樹脂組成物と基材(G)の密着性が乏しくなったり、塗膜の柔軟性が失われ、脆くなる場合がある。
(8)化合物(A−1)および/または化合物(A−2)と、(A−3)および/または化合物(A−4)と、(A−5)および/または化合物(A−6)との組合せ。
(9)化合物(A−1)および/または化合物(A−2)と、化合物(A−7)との組合せ。
ここで、エチレン性不飽和結合当量(二重結合当量とも言う)(M)は、エチレン性不飽和結合当量=(エチレン性不飽和結合を有する化合物の1分子の分子量)/(エチレン性不飽和結合を有する化合物1分子中に含まれるエチレン性二重結合の数)で定義される。
(M)≦130であると、ラジカル重合における硬化収縮が大きく、(M)≧500であると、ラジカル重合における硬化が不十分となる場合がある。
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
芳香脂肪族ポリイソシアネートとしては、ω,ω’−ジイソシアネート−1,3−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジエチルベンゼン、1,4−テトラメチルキシリレンジイソシアネート、1,3−テトラメチルキシリレンジイソシアネート等を挙げることができる。
フェニレンジアミン、キシリレンジアミン、2,4−トリレンジアミン、2,6−トリレンジアミン、ジエチルトルエンジアミン,3,3’−ジクロロ−4,4’−ジアミノジフェニルメタン、4,4’−ビス−(sec−ブチル)ジフェニルメタン等の芳香族ジアミン;
トリメチルシリルジメチルアミン等の単官能のシリルアミノ基を保有するシリルアミン類;
1,1,3,3−テトラメチルジシラザン等の2官能のシリルアミノ基を保有するシリルアミン類が使用できる。
本発明の樹脂組成物は、各種活性エネルギー線の照射によって重合反応が進行し、硬化可能である。そのため樹脂組成物には、活性エネルギー線重合開始剤を含む必要がある。活性エネルギー線重合開始剤を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましい。
本発明の樹脂組成物は、本発明による効果を損なわない範囲であれば、各種添加剤を適宜配合することも可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩、及び染顔料等の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、シランカップリング剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、酸化防止剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、及び消泡剤等の、独立した充填剤としてではなく、ポリマーブレンド又はポリマーアロイとして、樹脂組成物中に、溶解、半溶解又はミクロ分散させることも可能である。
(I)第1の透明フィルム(第1の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第1の重合性接着層を形成する。また、第2の透明フィルム(第2の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第2の重合性接着層を形成する。次いで、ポリビニルアルコール系偏光子の両主面に、上記第1の重合性接着層と第2の重合性接着層とを、同時に/又は順番に、重ね合わせる。次いで、得られた積層体に活性エネルギー線を照射し、第1及び第2の接着層を重合硬化させる。
<活性エネルギー線重合性樹脂組成物の調整>
[実施例1〜50][比較例1〜6]
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、表1〜2に示す比率(重量部)で仕込み、ディスパーにて十分に攪拌を行い、十分に脱泡を行った後、実施例に示す活性エネルギー線重合性樹脂組成物をそれぞれ得た。この活性エネルギー線重合性樹脂組成物をそれぞれ、以下の手法によって積層体を作成し評価した。評価結果も表1〜表2に示した。なお、表1〜2中の例示材料、フィルムについて表3、表4に具体的に示す。本明細書において実施例1〜9、14〜19、23〜25、29、33、34、39〜42、47〜50は、参考例である。
透明フィルム(1)、(2)として、表1〜2に示すフィルムを使用し、以下の方法で積層体Aを作成した。
透明フィルム(1)、(2)の表面に300W・min/m2 の放電量でコロナ処理を行い、表面処理後1時間以内に、表1〜表3に示す活性エネルギー線重合性接着剤をワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、活性エネルギー線重合性接着層を形成し、前記活性エネルギー線重合性接着層との間にポリビニルアルコール系偏光子を挟み、透明フィルム(1)/接着層/PVA系偏光子/接着層/透明フィルム(2)からなる積層体を得た。透明フィルム(1)がブリキ板に接するように、この積層体の四方をセロハンテープで固定し、ブリキ板に固定した。
得られた偏光板を、10mm×100mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを平らな台の上に置き、サンプルの片端をセロファンテープで台に固定し、逆端の台からの高さを計測した。サンプルを平らな台の上に、両端が浮き上がる向きに置き、サンプルの片端をセロファンテープで台に固定し、逆端の台からの浮き上がり高さを計測した。この高さを反りとして4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:反りが0(mm)以上〜5.0(mm)未満。
○:反りが5.0(mm)以上〜10.0(mm)未満。
△:反りが10.0(mm)以上〜20.0(mm)未満。
×:反りが20.0(mm)以上
接着力は、JIS K6 854−4 接着剤−剥離接着強さ試験方法−第4部:浮動ローラー法に準拠して測定した。
即ち、得られた偏光板を、25mm×150mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを両面粘着テープ(トーヨーケム社製DF8712S)を使用して、ラミネータを用いて金属板上に貼り付けて、偏光板と金属板との測定用の積層体を得た。測定用の積層体の偏光板には、保護フィルムと偏光子の間に予め剥離のキッカケを設けておき、この測定用の積層体を23℃、相対湿度50%の条件下で、300mm/分の速度で90°の角度で引き剥がし、剥離力とした。この際、ポリビニルアルコール系偏光子と保護フィルム(1)、及びポリビニルアルコール系偏光子と保護フィルム(2)との双方の剥離力を測定した。この剥離力を接着力として4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:剥離不可、あるいは偏光板破壊
○:剥離力が2.0(N/25mm)以上〜5.0(N/25mm)未満。
△:剥離力が1.0(N/25mm)以上〜2.0(N/25mm)未満。
×:剥離力が1.0(N/25mm)未満。
ダンベル社製の100mm×100mmの刃を用い、作製した偏光板を保護フィルム(1)側から打ち抜いた。
打ち抜いた偏光板の、周辺の剥離距離を定規で測定し、以下の4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0mm
○:1mm以下
△:1〜3mm
×:3mm以上
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、80℃−dry、及び100℃dryの条件下で、それぞれ1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:100℃−dryの条件下でも剥がれが全く無し。
○:80℃−dry条件下で剥がれが全く無し。
△:80℃−dry条件下で1mm未満の剥がれあり。
×:80℃−dry条件下で1mm以上の剥がれあり。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、60℃−90%RHの条件下、及び85℃−85%RHの条件下で1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:85℃−85%RHの条件下でも剥がれが全く無し。
○:60℃−90%RHの条件下で剥がれが全く無し。
△:60℃−90%RHの条件下で1mm未満の剥がれあり。
×:60℃−90%RHの条件下で1mm以上の剥がれあり。
表1、2に示した樹脂組成物を活性エネルギー線重合性コート剤として使用し、以下の方法で積層体Bを作成した。
光学フィルム表面を300W・min/m2の放電量でコロナ処理を行い、表面処理後1時間以内に、配合例に示す樹脂組成物を活性エネルギー線重合性コート剤として、ワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、コート剤層を形成した。光学フィルムがブリキ板に接するように、この積層体の四方をセロハンテープで、ブリキ板に固定した。
得られた偏光板を、10mm×100mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを平らな台の上に置き、サンプルの片端をセロファンテープで台に固定し、逆端の台からの高さを計測した。サンプルを平らな台の上に、両端が浮き上がる向きに置き、サンプルの片端をセロファンテープで台に固定し、逆端の台からの浮き上がり高さを計測した。この高さを反りとして4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:反りが0(mm)以上〜5.0(mm)未満。
○:反りが5.0(mm)以上〜10.0(mm)未満。
△:反りが10.0(mm)以上〜20.0(mm)未満。
:反りが20.0(mm)以上
JIS K5400に従い、碁盤目剥離試験を実施した。100マス中の剥離したマス数を4段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0マス
○:1〜10マス
△:11〜30マス
×:31マス以上
これに対して表2に示した比較例の接着剤としての評価では、比較例1〜4は、特に反りの評価が悪く、比較例5、6では、反りは良好であるが、接着性、打ち抜き加工性、耐熱性、耐湿熱性が悪いことがわかる。また、コート剤としての評価では、比較例1〜6の反りの評価が悪いことがわかる。
Claims (9)
- α,β−不飽和二重結合基含有化合物(A)と、
活性エネルギー線カチオン重合開始剤(B)とを必須成分とし、下記(1)〜(3)を特徴とする活性エネルギー重合性樹脂組成物。
(1)化合物(A)が、化合物(A−5)の化合物を必須として含有する。
化合物(A−5):(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸4−ヒドロキシブチル、およびシクロヘキサンジメタノールモノ(メタ)アクリル酸エステルからなる群より選択される1種以上の分子内に1個以上のヒドロキシ基を有するα,β−不飽和二重結合基含有化合物。
(2)化合物(A)100重量部に対して、活性エネルギー線カチオン重合開始剤(B)を1〜10重量部含む。
(3)活性エネルギー線ラジカル重合開始剤(ただし、カチオン重合開始剤(B)である場合を除く)を含まない。 - 化合物(A)が、
化合物(A−5)および化合物(A−6):分子内に1個以上のアミノ基を有するα,β−不飽和二重結合基含有化合物(ただし酸アミド由来のアミノ基を除く)と、
化合物(A−4):分子内に1個以上のカルボキシ基を有するα,β−不飽和二重結合基含有化合物とを含有する場合において、
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−5)と、化合物(A−6)と、化合物(A−4)との合計が10〜80重量部である請求項1記載の活性エネルギー重合性樹脂組成物。 - 化合物(A)が、
化合物(A−3):分子内に1個以上のケトン基を有するα,β−不飽和二重結合基含有化合物(ただし、アクリロイル基由来のカルボニル基を除く)と、
化合物(A−5)とを含有する場合において、
活性エネルギー重合性樹脂組成物100重量部中、化合物(A−3)および化合物(A−5)の合計が10〜80重量部である請求項1記載の活性エネルギー重合性樹脂組成物。 - 化合物(A)が、
化合物(A−1):分子内に1個以上の脂肪族へテロ環構造を有するα,β−不飽和二重結合基含有化合物および/または化合物(A−2):分子内に1個以上のビニル基を有するα,β−不飽和二重結合基含有化合物(ただし、ビニル基はα,β−不飽和二重結合基以外に有する官能基とし、アクリロイル骨格由来のビニル基は除く)と、
化合物(A−3):分子内に1個以上のケトン基を有するα,β−不飽和二重結合基含有化合物(ただし、アクリロイル基由来のカルボニル基を除く)または化合物(A−4):分子内に1個以上のカルボキシ基を有するα,β−不飽和二重結合基含有化合物と、
化合物(A−5)および化合物(A−6):分子内に1個以上のアミノ基を有するα,β−不飽和二重結合基含有化合物(ただし酸アミド由来のアミノ基を除く)とを含有することを特徴とする請求項1記載の活性エネルギー重合性樹脂組成物。 - 化合物(A)のエチレン性不飽和結合当量を(M)としたとき、
130<(M)<500の範囲であることを特徴とする請求項1〜4いずれか1項に記載の活性エネルギー重合性樹脂組成物。 - 基材(G)と、
該基材(G)の少なくとも一方の主面に設けられた請求項1〜5いずれか1項に記載の活性エネルギー重合性樹脂組成物からなる樹脂層とを有する積層体。 - 基材(G)が、透明フィルム(H)であることを特徴とする請求項6記載の積層体。
- 前記透明フィルム(H)が、ポリアセチルセルロース系フィルム、ポリノルボルネン系フィルム、ポリプロピレン系フィルム、ポリアクリル系フィルム、ポリカーボネート系フィルム、ポリエステル系フィルム、ポリビニルアルコール系フィルム及びポリイミド系フィルムからなる群から選択される少なくとも1種であることを特徴とする請求項7記載の積層体。
- 光学フィルムと、
該光学フィルムの少なくとも一方の主面に設けられた請求項1〜5いずれか記載の活性エネルギー重合性樹脂組成物からなる樹脂層とを有する光学素子用積層体。
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