JP2015040278A - 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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- JP2015040278A JP2015040278A JP2013173290A JP2013173290A JP2015040278A JP 2015040278 A JP2015040278 A JP 2015040278A JP 2013173290 A JP2013173290 A JP 2013173290A JP 2013173290 A JP2013173290 A JP 2013173290A JP 2015040278 A JP2015040278 A JP 2015040278A
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- meth
- active energy
- acrylate
- dioxolan
- energy ray
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- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- YQPZJBVEKZISEF-UHFFFAOYSA-N tetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YQPZJBVEKZISEF-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- DPUZPWAFXJXHBN-UHFFFAOYSA-N tetrasodium dioxidoboranyloxy(dioxido)borane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]B([O-])OB([O-])[O-] DPUZPWAFXJXHBN-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003639 thymyl group Chemical group C1(=CC(C)=CC=C1C(C)C)* 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- LWLOKSXSAUHTJO-IMJSIDKUSA-N trans-2,3-butylene carbonate Chemical compound C[C@@H]1OC(=O)O[C@H]1C LWLOKSXSAUHTJO-IMJSIDKUSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 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
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- YSFRAAQCARVMFR-UHFFFAOYSA-N tris(2-methylbutan-2-yl) borate Chemical compound CCC(C)(C)OB(OC(C)(C)CC)OC(C)(C)CC YSFRAAQCARVMFR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-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
- 235000012711 vitamin K3 Nutrition 0.000 description 1
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- 229940041603 vitamin k 3 Drugs 0.000 description 1
- 239000002023 wood Substances 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
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Landscapes
- Polarising Elements (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
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。
更に近年、偏光子や保護フィルムの薄膜化が進んでおり、(メタ)アクリロイル基を有する化合物に係る硬化性成分を含有する活性エネルギー線硬化型接着剤により偏光板を形成した場合、接着剤の硬化収縮が大きいため偏光板にシワや凹凸が発生することがある。
α,β−エチレン性不飽和二重結合基含有化合物(M)9重量部〜99と、
カチオン重合性化合物(N) 0.5重量部〜90重量部と、
ホウ酸及び/又はホウ酸誘導体(N)0.1重量部〜10重量部とを含有することを特徴とする上記活性エネルギー線重合性組成物に関する。
本発明の活性エネルギー線重合性樹脂組成物のα,β−エチレン性不飽和二重結合基含有化合物(M)は、分子内にα,β−エチレン性不飽和二重結合を含有する全ての化合物が含まれる。α,β−エチレン性不飽和二重結合含有化合物(M)としては、活性エネルギー線による反応性の観点から、好ましくはα,β−エチレン性不飽和二重結合の総重量のうち、(メタ)アクリロイル基が50重量%〜100重量%を占めるように設計されるのが好ましい。
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;
化合物(X)としては、基材との密着性の面より、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸4−ヒドロキシブチル、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、ε−カプロラクトン1〜2mol付加(メタ)アクリル酸2−ヒドロキシエチル等の炭素数2〜18であるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
ノルボルネン及び/又はノルボルナン骨格を有するα,β−エチレン性不飽和二重結合基含化合物(c2)としては、ノルボルネン及び/又はノルボルナン骨格とエチレン性不飽和二重結合を1個以上有していればよく、例えばジシクロペンテニル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジメチロールジシクロペンタンジ(メタ)アクリレート、トリシクロデカンジメタノール(メタ)アクリレート、イソボニル(メタ)アクリレートなどが挙げられる。
例えば、(メタ)アクリル酸パーフルオロメチル、(メタ)アクリル酸パーフルオロエチル、(メタ)アクリル酸パーフルオロプロピル、(メタ)アクリル酸パーフルオロブチル、(メタ)アクリル酸パーフルオロオクチル、(メタ)アクリル酸トリフルオロメチルメチル、(メタ)アクリル酸2−トリフルオロメチルエチル、(メタ)アクリル酸ジパーフルオロメチルメチル、(メタ)アクリル酸2−パーフルオロエチルエチル、(メタ)アクリル酸2−パーフルオロメチル−2−パーフルオロエチルメチル、(メタ)アクリル酸トリパーフルオロメチルメチル、(メタ)アクリル酸2−パーフルオロエチル−2−パーフルオロブチルエチル、(メタ)アクリル酸2−パーフルオロヘキシルエチル、(メタ)アクリルプロペン酸2−パーフルオロデシルエチル、(メタ)アクリル酸2−パーフルオロヘキサデシルエチルなどの(メタ)アクリル酸パーフルオロアルキルエステル類;
例えば、ギ酸ビニル、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、カプリン酸ビニル、ラウリン酸ビニル、バーサチック酸ビニル、ピバリン酸ビニル、パルミチン酸ビニル、ステアリン酸ビニル等のカルボン酸のビニルエステル類;
例えば、エチルビニルエーテル、1−プロピルビニルエーテル、2−プロピルビニルエーテル、n−ブチルビニルエーテル、sec−ブチルビニルエーテル、iso−ブチルビニルエーテル、tert−ブチルビニルエーテル、n−アミルビニルエーテル、n−ヘキシル、2−エチルヘキシルビニルエーテル、n−オクチルビニルエーテル、iso−オクチルビニルエーテル、n−ノニルビニルエーテル、iso−ノニルビニルエーテル、デシルビニルエーテル、ドデシルビニルエーテル、オクタデシルビニルエーテル、ラウリルビニルエーテル、ステアリ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)アリルクロロシラン、(メタ)アリルトリメトキシシラン、(メタ)アリルトリエトキシシラン、(メタ)アリルアミノトリメチルシラン、ジエトキシエチルビニルシラン、トリクロロビニルシラン、トリメトキシビニルシラン、トリエトキシビニルシラン、トリプロポキシビニルシラン、ビニルトリス(2−メトキシエトキシ)シラン等のアルコキシシリル基含有α,β−不飽和二重結合基含有化合物類;
例えば、ビニルスルホン酸アンモニウム、ビニルスルホン酸ナトリウム、ビニルスルホン酸カリウム、ナトリウムビニルアルキルスルホサクシネート等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;
例えば、アレン、1,2−ブタジエン、1,3−ブタジエン、2−メチル−1,3−ブタジエン、2−クロロ−1,3−ブタジエンなどのジエン類;
例えば、cis−コハク酸ジアリル、2−メチリデンコハク酸ジアリル、(E)−ブタ−2−エン酸ビニル、(Z)−オクタデカ−9−エン酸ビニル、(9Z,12Z,15Z)−オクタデカ−9,12,15−トリエン酸ビニル等の多官能の不飽和結合を含有する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。
カチオン重合性化合物(B)はカチオンにより重合する化合物を全て含んでいる。カチオン重合性化合物(B)としては活性エネルギー線による反応性の観点から、環状ヘテロ化合物やビニルエーテル化合物が好ましく、3員環エーテルであるオキシラン化合物(b1)が特に好ましい。
オキシラン化合物(b1)としては、例えば、オキシラン、メチルオキシラン、フェニルオキシラン、1,2−ジフェニルオキシラン、メチリデンオキシラン、オキシラニルメチル、オキシラニルメタノール、オキシランカルボン酸、(クロロメチル)オキシラン、(ブロモメチル)オキシラン、オキシラニルアセトニトリル等の脂肪族系環状エーテル基;例えば、3,4−オキシランシクロヘキシルメチル 3,4−オキシランシクロヘキサンカルボキシレート、3,4−オキシラン−6−メチルシクロヘキシルメチル 3,4−オキシラン−6−メチルシクロヘキサンカルボキシレート、エチレンビス(3,4−オキシランシクロヘキサンカルボキシレート)、ビス(3,4−オキシランシクロヘキシルメチル)アジペート、ビス(3,4−オキシラン−6−メチルシクロヘキシルメチル) アジペート、ジエチレングリコールビス(3,4−オキシランシクロヘキシルメチルエーテル)、エチレングリコールビス(3,4−オキシランシクロヘキシルメチルエーテル)、2,3,14,15−ジオキシラン−7,11,18,21−テトラオキサトリスピロ−[5.2.2.5.2.2]ヘンイコサン(また、3,4−オキシランシクロヘキサンスピロ−2’,6’−ジオキサンスピロ−3’’,5’’−ジオキサンスピロ−3’’’,4’’’−オキシランシクロヘキサンとも命名できる化合物)、4−(3,4−オキシランシクロヘキシル)−2,6−ジオキサ−8,9−オキシランスピロ[5.5]ウンデカン、4−ビニルシクロヘキセンジオキサイド、ビス−2,3−オキシランシクロペンチルエーテル、及びジシクロペンタジエンジオキサイド等の脂環式環に結合した三員環状の環状エーテル基が挙げられる。これら三員環状の環状エーテル基含有化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合した化合物が、オキシラン化合物(b1)となりうる。
ここに例示したオキシラン化合物は、それぞれ単独で使用してもよいし、また複数のオキシラン化合物を混合して使用してもよい。
等の環状化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合し得る芳香環が挙げられる。
オキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−2−オン、7−[2−(2−オキソ−4−メチル−1,3−ジオキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−2−オン、5−(ベンジルオキシ)−1,3−ジオキソラン−2−オン、4−(イソブトキシメチル)−1,3−ジオキソラン−2−オン、4−(4−ノニルベンジルオキシメチル)−1,3−ジオキソラン−2−オン、4−(4−クロロフェニルチオメチル)−1,3−ジオキソラン−2−オン、4−[3−(クロロメチル)フェニル]−1,3−ジオキソラン−2−オン、4−[4−(クロロメチル)フェニル]−1,3−ジオキソラン−2−オン、4,4−ジプロピル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジペンチル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジイソプロピル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジフェネチル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ビス(2−シクロヘキシルエチル)−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4−[1−(フェニルチオ)シクロヘキシル]−1,3−ジオキソラン−2−オン、4−(3−メトキシ−4−エトキシフェニル)−5−(ヒドロキシメチル)−1,3−ジオキソラン−2−オン、4−(フェノキシカルボニルオキシメチル)−1,3−ジオキソラン−2−オン、4−ベンジリデン−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−[(2−ナフチル)メチレン]−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−(4−クロロベンジリデン)−5,5−ジメチル−1,3−ジオキソラン−2−オン、5−メチル−5−フェニル−4−(3−フェニルプロピリデン)−1,3−ジオキソラン−2−オン、5,5−ジメチル−4−(3−フェニルプロピリデン)−1,3−ジオキソラン−2−オン、4−[4−(クロロカルボニルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−クロロ−1,3−ジオキソラン−2−オン、4−クロロ−4,5−ジメチル−1,3−ジオキソラン−2−オン、4−(クロロカルボニルオキシメチル)−1,3−ジオキソラン−2−オン、4−(p−クロロフェノキシメチル)−1,3−ジオキソラン−2−オン、4−(クロロメチル)−1,3−ジオキソラン−2−オン、4,5−ジクロロ−1,3−ジオキソラン−2−オン、(4S,5R)−4,5−ジフェニル−1,3−ジオキソラン−2−オン、4α,5α−ジメチル−1,3−ジオキソラン−2−オン、(4R,5R)−4,5−ジメチル−1,3−ジオキソラン−2−オン、(4S,5S)−4,5−ジメチル−1,3−ジオキソラン−2−オン、(4S)−4β−メチル−1,3−ジオキソラン−2−オン、(R)−4−メチル−1,3−ジオキソラン−2−オン、(S)−5−エチル−1,3−ジオキソラン−2−オン、4−[(トリフェニルシリル)メチル]−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−[9−(3−チエニル)ノニル]−1,3−ジオキソラン−2−オン、4−(メチルアミノメチル)−1,3−ジオキソラン−2−オン、4−(4−クロロフェニルチオ)−1,3−ジオキソラン−2−オン、4−(フェニルチオ)−1,3−ジオキソラン−2−オン、4−(4−メトキシフェニルチオ)−1,3−ジオキソラン−2−オン、4−(4−ブロモフェニルチオ)−1,3−ジオキソラン−2−オン4−(フェニルチオメチル)−1,3−ジオキソラン−2−オン、4,4′−[スルホニルビス(p−フェニレンオキシメチレン)]ビス(1,3−ジオキソラン−2−オン)、4−(4−メチルフェニルチオ)−1,3−ジオキソラン−2−オン、4,4,5,5−テトラメチル−2−(フェニルスルホニルオキシイミノ)−1,3−ジオキソラン、2−(4−ニトロフェノキシ)−4−メチル−2−ホスファ(V)−1,3−ジオキソラン−2−オン、4−(グリシジルオキシメチル)−1,3−ジオキソラン−2−オン、グリシジルカルバミド酸(2−オキソ−1,3−ジオキソラン−4−イル)メチル、4−(ノルボルナ−5−エン−2−イル)−1,3−ジオキソラン−2−オン、4−[2−(2−ナフチル)エチル]−5−メトキシ−1,3−ジオキソラン−2−オン、4−[2−(1−ナフチル)エチル]−5−メトキシ−1,3−ジオキソラン−2−オン、4,4−ジメチル−5−(3−チエニルメチレン)−1,3−ジオキソラン−2−オン、4−[2−[ジメチル(トリメチルシリルオキシ)シリル]エチル]−1,3−ジオキソラン−2−オン、4−[2−[(メチル)ビス(トリメチルシリルオキシ)シリル]エチル]−1,3−ジオキソラン−2−オン、4−[2−(トリメチルシリル)エチル]−1,3−ジオキソラン−2−オン、4−[4−(グリシジルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−[4−(2−オキソ−1,3−ジオキソラン−4−イルメチルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−[4−(グリシジルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−(2−オキソ−1,3−ジオキソラン−4−イルメチルカルバモイルオキシメチル)−1,3−ジオキソラン−2−オンなどの5員環カーボネート類;
例えば、ホウ酸とアルコール又はフェノールとの反応により得られるもの、例えば、ホウ酸トリメチル、ホウ酸トリエチル、ホウ酸トリ−n−プロピル、ホウ酸トリ−n−ブチル、ホウ酸トリフェニル、ホウ酸トリイソプロピル、ホウ酸トリ−t−アミル、ホウ酸トリフェニル、トリメトキシボロキシン、ホウ酸トリ−2−シクロヘキシルシクロヘキシル、ホウ酸トリエタノールアミン、ホウ酸トリイソプロピルアミン、ホウ酸マンニトール、ホウ酸グリセロール、及びホウ酸トリイソプロパノールアミンなどのホウ酸エステル類が挙げられる。
また、本発明のホウ酸誘導体には、ボロン酸の誘導体も含まれる。例えば、メチルボロン酸、エチルボロン酸、ブチルボロン酸、シクロヘキシルボロン酸などの、アルキル又はアルケニルボロン酸;
例えば、フェニルボロン酸、ナフタレンボロン酸、アントラセンボロン酸などの、アリールボロン酸又はこれらのアリール基に任意の置換基を有する、置換型アリールボロン酸が挙げられる。
この目的に適切な重合体には、種々の活性水素含有重合体のいずれかを挙げられ得、これには、例えば、アクリル重合体、ポリエステル重合体、ポリウレタン重合体、ポリエーテル重合体の少なくとも1種から選択される。
α,β−エチレン性不飽和二重結合基含有化合物(M)9重量部〜99重量部、カチオン重合性化合物(B)0.5重量部〜90重量部、ホウ酸及び/又はホウ酸誘導体(N)0.1重量部〜10重量部である。
より好ましくはα,β−エチレン性不飽和二重結合基含有化合物(M)30重量部〜80重量部、カチオン重合性化合物(B)20重量部〜70重量部、ホウ酸及び/又はホウ酸誘導体(N)0.3重量部〜7重量部である。
α,β−エチレン性不飽和二重結合基含有化合物(M)が9重量部より少ないと、相対的にカチオン重合性化合物(B)が多くなり、基材中の水分や湿度により硬化不良をおこしやすい。α,β−エチレン性不飽和二重結合基含有化合物(M)が99重量部より多いと、硬化収縮が大きくなり薄膜基材を貼り合せた場合にシワが入り外観不良がおきやすい。ホウ酸及び/又はホウ酸誘導体(N)が0.1重量部未満であると所望の接着力発現に至らず、10重量%以上であると、時間の経過で析出してきたり、液としての粘度が上がりすぎてゲル化したりするなどの問題が生じる場合がある。
さらにホウ酸及び/又はホウ酸誘導体(N)を併用することで化合物(X)及び/又はカチオン重合性化合物(B)が重合して生成する水酸基と基材の水酸基と結合を形成して密着性を良くする
なお、電子線照射によってラジカル重合反応を進行させる場合には、重合開始剤を含む必要はない。
本発明における活性エネルギー線重合性樹脂組成物は、樹脂組成物層の膜厚が使用用途によって、0.1〜6μmの場合には、粘度は1〜1500mPa・sであることが重要であり、好ましくは10〜1300mPa・sであり、20〜1000mPa・sであることがより好ましい。粘度が1500mPa・sより高いと基材(F)に塗工した場合、0.1〜6μmの薄膜塗工ができず、透過率等の光学的特性が悪化してしまう。一方、粘度が1mPa・sより低いと樹脂組成物層の膜厚制御が困難になる。
常法にしたがって適当な方法で基材の片面、又は両面に活性エネルギー線重合性樹脂組成物を塗工して、さらに別の基材を活性エネルギー線重合性樹脂組成物の面に積層することで積層体を形成することができる。樹脂組成物層の要求膜厚は使用用途によって異なる。
本発明の活性エネルギー線重合性樹脂組成物を基材等に塗工する方法としては、特に制限は無く、マイヤーバー、アプリケーター、刷毛、スプレー、ローラー、グラビアコーター、ダイコーター、マイクログラビアコーター、リップコーター、コンマコーター、カーテンコーター、ナイフコーター、リバースコ−ター、スピンコーター等種々の塗工方法が挙げられるが、薄膜塗工や厚膜塗工等、用途により使用可能であり、特に制限はない。
本発明の活性エネルギー線重合性樹脂組成物が使用されは基材(F)としては、フィルム状基材、ガラス板、紙加工品等、特に制限無く使用できる。一方、二つ以上の基材(F)を貼り合わせる接着剤として使用する場合には、活性エネルギー線を照射して重合させるために、活性エネルギー線を透過し易い基材を使用する必要があり、特に透明フィルムや透明ガラス板を使用する事が好ましい。片方を活性エネルギー線が透過し難い基材、例えば、木材、金属板、プラスチック板、紙加工品等を使用した場合でも、もう片方を透明フィルムや透明ガラス板を使用し、透明フィルムや透明ガラス板側から照射し、重合硬化を行えば使用は可能である。
本発明の透明フィルムの積層体は、以下のようにして得ることができる。
本発明の透明フィルムは、ディスプレイやタッチパネル等の情報通信機器等の光学フィルムに使用する事ができる。
光学用積層体の基本的積層構成は、透明フィルム/樹脂層/透明フィルム、あるいは透明フィルム/樹脂層/透明フィルム/樹脂層/透明フィルムのようなシート状の両面活性エネルギー線重合性樹脂組成物積層体である。さらには、透明フィルム/樹脂層/透明フィルム/樹脂層/透明フィルム/樹脂層/透明フィルム、ガラス、あるいは光学成形体のような多層の光学フィルムを光学部材に固定化した光学素子用積層体として使用される。
透明フィルムの厚さは、適宜に決定しうるが、一般には強度や取扱性等の作業性、薄層性などの点より1〜500μm程度である。特に1〜300μmが好ましく、5〜200μmがより好ましい。透明フィルムは、5〜150μmの場合に特に好適である。
本発明における光学素子用積層体としては、上記の各種透明フィルムのうち、主に光学用途にて用いられる光学フィルムが好適に使用される。ここで、光学フィルムとは、上記透明フィルムに特殊な処理を施されたものであり、光学的機能(光透過、光拡散、集光、屈折、散乱、HAZE等の諸機能)を有するものが光学フィルムと称されている。これらの光学フィルムは単独又は数種を組み合わせて使用することができる。本発明の一実施形態では、上記光学フィルムの少なくとも一方の主面に、上記樹脂組成物からなる樹脂層を形成することによって、光学素子用積層体を構成することができる。
透明フィルムである第2の保護フィルムの一方の面に、活性エネルギー線重合性樹脂組成物を塗工し、第2の重合性樹脂層を形成し、
次いで、ポリビニルアルコール系偏光子の各面に、第1の重合性樹脂層及び第2の重合性樹脂層面を、同時に/又は順番に重ね合わせた後、活性エネルギー線を照射し、第1の活性エネルギー線重合性樹脂層層及び第2の活性エネルギー線重合性樹脂層を重合硬化することによって製造する方法。
また、「重量平均分子量」は、東ソー株式会社製ゲルパーミエイションクロマトグラフィー「HLC−8220GPC」を使用した測定した数値であり、分離カラム:東ソー株式会社製「TSK−GEL SUPER H5000」、「TSK−GEL SUPER H4000」、「TSK−GEL SUPER H3000」、及び「TSK−GEL SUPER H2000」を4本直列に繋ぎ、移動相に温度40℃のテトラヒドロフランを用いて、0.6ml/分の流速で測定したポリスチレン換算重量平均分子量である。
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、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及び2に示した。
4HBA:アクリル酸4−ヒドロキシブチル
HEA:アクリル酸2−ヒドロキシエチル
CHDMMA:シクロヘキサンジメタノールモノメタクリレート
DCPA:ジシクロペンタニルアクリレート
IBXA:イソボニルアクリレート
FA−511AS:ジシクロペンテニルアクリレート(日立化成社製 ファンクリル511A
S)
nBA:n−ブチルアクリレート
NPDA:ネオペンチルグリコールジアクリレート
PET3A:ペンタエリスリトールトリアクリレート
INATA:イソシアヌル酸EO変性トリアクリレート(東亞合成化学社製:アロニックスM
−315)
オリゴマー1:合成例1で得られたポリウレタンアクリレート Mw=4000
化合物1:
JER806:ビスフェノールFジグリシジルエーテル(三菱化学社製)
CEL2021P:3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート (ダイセル社製 セロキサイド2021P)
OXT−121:キシリレンビスオキセタン(東亞合成社製 アロンオキセタンOXT−121)
EC:エチレンカーボネート
CPI−110P:サンアプロ社製 トリアリールスルホニウム塩タイプの光酸発生剤
IRG250:4−イソブチルフェニル(4−メチルフェニル)ヨードニウム・ヘキサフルオロホスファート(BASF社製 イルガキュア250)
TPO:2,4,6−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイト゛ (BASF社製 ルシチンTPO)
DETX−S:日本化薬社製 チオキサントン系増感剤
撹拌機、還流冷却管、ガス導入管、温度計、滴下ロ−トを備えた5口セパラブルフラスコに、ポリテトラメチレングリコール(保土ヶ谷化学株式会社製:PTG850、水酸基価127.1mgKOH/g)を81.6部、イソホロンジイソシアネートを41.4部仕込み乾燥空気を導入しながら60℃に昇温した。ここへジブチル錫ジラウレートを0.05部添加し、1時間反応させた。別途、滴下ロートに4−ヒドロキシブチルアクリレートを27.0部、ハイドロキノンモノメチルエーテルを0.15部仕込み、1時間かけてセパラブルフラスコへ滴下した。滴下終了後、3時間80℃で攪拌を続けた後、赤外線吸収スペクトルにてイソシアナト基の吸収ピークがないことを確認し反応を終了しオリゴマー2を得た。生成物の重量平均分子量は4000であった。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
透明フィルム(1)として、富士フィルム社製の紫外線吸収剤含有ポリトリアセチルセルロース系フィルム:商品名「フジタック:80μm」を用い、透明フィルム(2)として、富士フィルムビジネスサプライ社製の紫外線吸収剤を含有しないポリトリアセチルセルロース系フィルム:商品名「TAC50μ」(厚み50μm)を使用し、それぞれその表面に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に示す活性エネルギー線重合性樹脂組成物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樹脂層を形成し、前記活性エネルギー線重合性樹脂層との間に上記のポリビニルアルコール系偏光子を挟み、透明フィルム(1)/樹脂層/PVA系偏光子/樹脂層/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。
透明フィルム(1)として、富士フィルム社製の紫外線吸収剤含有ポリトリアセチルセルロース系フィルム:商品名「フジタック:40μm」を用い、透明フィルム(2)として、日本ゼオン社製の紫外線吸収剤を含有しないポリシクロオレフィン系フィルム(厚み23μm)を使用し、それぞれその表面に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に示す活性エネルギー線重合性樹脂組成物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樹脂層を形成し、前記活性エネルギー線重合性樹脂層との間に上記のポリビニルアルコール系偏光子を挟み、透明フィルム(1)/樹脂層/PVA系偏光子/樹脂層/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。
厚み50μmのポリエチレンテレフタレート(以下PETと略す)フィルム上に、表1及び表2の活性エネルギー線重合性樹脂組成物をバーコーターにより8μmの厚みに塗布した。これに厚さ50μmのPETフィルムをニップロールにより貼りあわせた後、活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の紫外線を片側から照射して積層体Bを得た。
得られた積層体Aについて、剥離強度、打ち抜き加工性、耐熱性及び耐湿熱性、積層体外観を、積層体Bについて、積層体外観を以下の方法に従って求めた。また、積層体Cにおいて、耐湿熱試験後の透過率、着色を以下の方法に従って確認した。結果を同様に表1に示した。
接着力は、JIS K6 854−4 接着剤(重合性樹脂組成物)−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、得られた積層体A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、透明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透明フィルム(1)、及びポリビニルアルコール系偏光子と透明フィルム(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。
◎:剥離不可、あるいは偏光板破壊
○:剥離力が2.0(N/25mm)以上
△: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(実用性なし)
ダンベル社製の100mm×100mmの刃を用い、作製した偏光板を透明フィルム(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。
◎:0mm
○:1mm未満
△:1mm以上3mm未満
×:3mm以上(実用性なし)
各接着剤で貼りあわされた積層体A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。
◎: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(実用性なし)
各接着剤で貼りあわされた積層体Aを、50mm×40mmの大きさに裁断し、温度60℃−湿度90%の条件下、及び温度85℃−湿度85%の条件下で1000時間暴露した。暴露後積層体A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
◎: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(実用性なし)
○:積層体にシワや凹凸が全くない
△:積層体にシワや凹凸が若干ある
×:積層体にシワや凹凸が全面にある(実用性なし)
各接着剤で貼りあわされた積層体Bを、50mm×40mmの大きさに裁断し、温度85℃−湿度85%の条件下で1000時間暴露用い、積分球式分光透過率測定器(村上色材技術研究所社製DOT-3C)でΔYIを測定した。ここでΔYIは、耐熱試験後のラミネートフィルムのYI値と試験前のPETフィルムのYI値の差で示した。
◎:0.5未満
○:0.5以上1.0未満
△:1.0以上1.5未満
×:1.5以上(実用性なし)
Claims (10)
- α,β−エチレン性不飽和二重結合基含有化合物(M)と、カチオン重合性化合物(B)と、ホウ酸及び/又はホウ酸誘導体(N)とを必須成分とする活性エネルギー線重合性樹脂組成物。
- 活性エネルギー線重合組成物100重量部中
α,β−エチレン性不飽和二重結合基含有化合物(M)9重量部〜99重量部と、
カチオン重合性化合物(B) 0.5重量部〜90重量部と、
ホウ酸及び/又はホウ酸誘導体(N)0.1重量部〜10重量部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線重合性樹脂組成物。 - α,β−エチレン性不飽和二重結合基含有化合物(M)が、水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(X)を含むことを特徴とする請求項1又は2記載の活性エネルギー線重合性樹脂組成物。
- α,β−エチレン性不飽和二重結合基含有化合物(M)が、2個以上のシクロアルカン骨格及び/又はシクロアルケン骨格を有するα,β−エチレン性不飽和二重結合基含化合物(C)を含むことを特徴とする請求項1〜3いずれか記載の活性エネルギー線重合性樹脂組成物。
- カチオン重合性化合物(B)が、オキシラン化合物(b1)を含むことを特徴とする請求項1〜4いずれか記載の活性エネルギー線重合性樹脂組成物。
- オキシラン化合物(b1)が、芳香環を有するオキシラン化合物(b1−1)を含むことを特徴とする請求項5記載の活性エネルギー線重合性樹脂組成物。
- さらに活性エネルギー線重合開始剤(E)を含有してなる請求項1〜6いずれか記載の活性エネルギー線重合性樹脂組成物。
- 請求項1〜7いずれか記載の活性エネルギー線重合性樹脂組成物からなる層を、基材(F)の片面、又は両面に積層してなることを特徴とする積層体。
- 基材(F)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又はポリイミド系フィルムであることを特徴とする請求項8記載の積層体。
- 請求項8又は9記載の積層体を用いてなる光学素子用積層体。
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