JP2023502580A - 光硬化性シリコーン組成物及びその硬化物 - Google Patents
光硬化性シリコーン組成物及びその硬化物 Download PDFInfo
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- JP2023502580A JP2023502580A JP2022524239A JP2022524239A JP2023502580A JP 2023502580 A JP2023502580 A JP 2023502580A JP 2022524239 A JP2022524239 A JP 2022524239A JP 2022524239 A JP2022524239 A JP 2022524239A JP 2023502580 A JP2023502580 A JP 2023502580A
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08F220/306—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and polyethylene oxide chain in the alcohol moiety
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F222/10—Esters
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
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Abstract
Description
本出願は、2019年11月24日に出願された米国仮特許出願第62/939,640号の優先権及び全ての利点を主張するものであり、その内容が、参照により本明細書に組み込まれる。
特許文献1:国際公開第2017/155919(A1)号
本発明の目的は、光デバイス又は画像表示における硬化物の亀裂及び剥離を抑制する光硬化性シリコーン組成物を提供することである。
本発明の光硬化性シリコーン組成物は、
(A)分子中に炭素数6~12の少なくとも1つのアリール基及び炭素数2~12の少なくとも1つのアルケニル基を有するオルガノポリシロキサン100質量部と、
(B)分子中に少なくとも2つのエーテル結合及び少なくとも1つの脂肪族炭素-炭素二重結合を有する有機化合物1~50質量部と、
(C)チオール基含有有機化合物であって、
(C1)分子中に2つのチオール基を有する有機化合物、及び
(C2)分子中に少なくとも3つのチオール基を有する有機化合物を含む、チオール基含有有機化合物4~40質量部と、
(D)光ラジカル開始剤0.05~2質量部と、を含む。
R1 aR2 bSiO(4-a-b)/2
によって表されるオルガノポリシロキサンである。
本発明の光硬化性シリコーン組成物は、活性エネルギー線を照射することによって硬化して、光硬化性シリコーン組成物を2つの基板間に積層して硬化させた場合であっても、熱老化後の亀裂及び剥離を抑制する、硬化物を形成する。
成分(A)は、本組成物のベース化合物であり、分子中に炭素数6~12の少なくとも1つのアリール基及び炭素数2~12の少なくとも1つのアルケニル基を有するオルガノポリシロキサンである。
R1 aR2 bSiO(4-a-b)/2
によって表されるオルガノポリシロキサンである。
Vi0.03Me1.03Ph0.97SiO0.99:ViMe2SiO(MePhSiO)65SiMe2Vi
Vi0.10Me1.10Ph0.90SiO0.95:ViMe2SiO(MePhSiO)18.4SiMe2Vi
Vi0.09Me1.06Ph0.91SiO0.97:PhSi{O(PhMeSiO)10SiMe2Vi}3
Hex0.09Me1.07Ph0.89SiO0.98:Si{O(PhMeSiO)10SiMe2Hex}4
Hex0.12Me1.12Ph0.88SiO0.94:HexMe2SiO(PhMeSiO)15SiMe2Hex
Vi0.06Me1.38Phe0.63SiO0.97:ViMe2SiO(PheMeSiO)20(Me2SiO)10SiMe2Vi
Hex0.06Me1.38Php0.63SiO0.97:HexMe2SiO(PhpMeSiO)20(Me2SiO)10SiMe2Hex
ヘキサンジオールビスチオグリコレート、エチレングリコールビス(3-チオプロピオネート)、ブタンジオールビス(3-チオプロピオネート)、トリメチロールプロパントリス(3-チオプロピオネート)、ペンタエリスリトールテトラキス(3-チオプロピオネート)、トリヒドロキシエチルトリイソシアヌル酸トリス(3-チオプロピオネート)、及びメルカプト基で置換されたオルガノポリシロキサンが挙げられる。
分子中に少なくとも1つのケイ素原子結合ヒドロキシ基と、少なくとも1つのケイ素原子結合アルケニル基を有するシロキサン化合物との混合物;メチルポリシリケート、エチルポリシリケート、及びエポキシ基含有エチルポリシリケートが挙げられる。粘着付与剤の含有量は限定されないが、その含有量は、成分(A)100質量部当たり、好ましくは0.01~10質量部の範囲内である。
本発明の硬化物は、上記の光硬化性シリコーン組成物に光を照射することにより得られる。本組成物を硬化させるために使用される光の例としては、紫外線及び可視光が挙げられるが、250~500nmの範囲の波長を有する光が好ましい。これは、優れた硬化性が得られ、硬化物が光により分解されないためである。
光硬化性シリコーン組成物を、所定形状の凹部を有する成形型に充填し、累積放射線(cumulative radiation)が4000mJ/cm2となるように405nmのUV-LEDランプを用いて上部の液面から紫外線で照射した。硬化物の外観を、目視検査によって観察した。
光硬化性シリコーン組成物を、所定形状の凹部を有する成形型に充填し、累積放射線が4000mJ/cm2となるように405nmのUV-LEDランプを用いて上部の液面から紫外線で照射した。硬化物の針入度を、JIS K 2220に準拠した1/4コーンで規定された針入度を用いて測定した。
光硬化性シリコーン組成物を、長さ25mm×幅75mm×厚さ2mmの2つのガラス基板の間に注ぎ、長さ25mm×幅25mm×厚さ0.2mmの接着面積を作製し、累積放射線が4000mJ/cm2となるように405nmのUV-LEDランプを用いて上部のガラス表面から紫外線で照射した。硬化物の重ね剪断強度を、JIS K 6850に準拠して測定した。同時に、重ね剪断伸長を、破断点での変形量に対する硬化物の厚さのパーセントで表した。
光硬化性シリコーン組成物を、長さ165mm×幅105mm×厚さ2mmのガラス基板と、長さ210mm×幅160mm×厚さ1mmのPMMAコーティングPC基板との間に充填し、長さ165mm×幅85mm×厚さ0.13mmの硬化物を作製した。積層体を、累積放射線が4000mJ/cm2となるように405nmのUV-LEDランプを用いて上部のガラス表面から紫外線で照射した。硬化積層体を90℃で24時間熱老化させ、その外観を目視で確認した。
表1~5に示す組成(質量部)に従って以下の成分を均一に混合して、実施例1~5及び比較例1~8の光硬化性シリコーン組成物を調製した。式中、「Me」、「Vi」、「Ph」、及び「Ep」は、それぞれ、メチル基、ビニル基、フェニル基、及び3-グリシドキシプロピル基を表す。表1において、「(c1)/(c2)」は、光硬化性シリコーン組成物中の成分(c2)1モルに対する成分(c1)のモル数を表す。更に、表1において、「SH/C=C」は、光硬化性シリコーン組成物中の成分(A)及び(B)中の脂肪族飽和炭素-炭素二重結合1モル当りの成分(C)中のチオール基のモル数を表す。光硬化性シリコーン組成物及びその硬化物の特性を表1に示す。
(a1)2000mPa・sの粘度を有し、以下の平均式:
ViMe2SiO(MePhSiO)18.4SiMe2Vi
(平均組成式:Vi0.10Me1.10Ph0.90SiO0.95)で表されるオルガノポリシロキサン。
ViMe2SiO(MePhSiO)65SiMe2Vi
(平均組成式:Vi0.03Me1.03Ph0.97SiO0.99)で表されるオルガノポリシロキサン。
(b1):150mPa・sの粘度を有するノニルフェノキシオクタエチレングリコールアクリレート
(b2):100mPa・sの粘度を有するトリデカエチレングリコールジアクリレート
(c1):1,4-ビス(3-チオブチリルオキシ)ブタン
(c2):ペンタエリスリトールテトラキス(3-チオブチレート)
(d1):ジフェニル(2,4,6-トリメチルベンゾイル)ホスフィンオキシド
(e1):2,6-ジ-tert-ブチル-p-クレゾール
(f1):アルミニウム-N-ニトロソ-N-フェニルヒドロキシルアミン
(g1)以下の平均単位式:
(Me2ViSiO1/2)0.18(MeEpSiO2/2)0.28(PhSiO3/2)0.54で表されるオルガノポリシロキサン。
Claims (9)
- (A)分子中に炭素数6~12の少なくとも1つのアリール基及び炭素数2~12の少なくとも1つのアルケニル基を有するオルガノポリシロキサン100質量部と、
(B)分子中に少なくとも2つのエーテル結合及び少なくとも1つの脂肪族炭素-炭素二重結合を有する有機化合物1~50質量部と、
(C)チオール基含有有機化合物であって、
(C1)分子中に2つのチオール基を有する有機化合物、及び
(C2)分子中に少なくとも3つのチオール基を有する有機化合物
を含む、チオール基含有有機化合物4~40質量部と、
(D)光ラジカル開始剤0.05~2質量部と、
を含む、光硬化性シリコーン組成物。 - 成分(A)が平均組成式:
R1 aR2 bSiO(4-a-b)/2
(式中、R1が炭素数2~12のアルケニル基であり、R2が炭素数1~12のアルキル基、炭素数6~12のアリール基、又は炭素数7~12のアラルキル基であり、但し、R2の少なくとも30mol%が前記アリール基又は前記アラルキル基であり、「a」及び「b」が1≦a+b≦2.5及び0.001≦a/(a+b)≦0.2を満たす正の数である)によって表されるオルガノポリシロキサンである、請求項1に記載の光硬化性シリコーン組成物。 - 成分(B)が、分子中に、少なくとも2つのエーテル結合及び少なくとも1つのアクリロイル基又はメタクリロイル基を有する有機化合物である、請求項1に記載の光硬化性シリコーン組成物。
- 成分(C)中の成分(C1)の成分(C2)に対するモル比が、0.45~2.8の範囲である、請求項1に記載の光硬化性シリコーン組成物。
- 成分(D)が、リン原子を有する光ラジカル開始剤である、請求項1に記載の光硬化性シリコーン組成物。
- 成分(A)100質量部当たり0.001~1質量部の量の、(E)ヒンダードフェノール化合物を更に含む、請求項1に記載の光硬化性シリコーン組成物。
- 成分(A)100質量部当たり0.0001~1質量部の量の、(F)成分(E)以外のラジカル捕捉剤を更に含む、請求項1に記載の光硬化性シリコーン組成物。
- 成分(A)100質量部当たり10質量部以下の量の、(G)接着付与剤を更に含む、請求項1に記載の光硬化性シリコーン組成物。
- 請求項1、又は請求項2~8のいずれか一項に記載の光硬化性シリコーン組成物に光を照射することによって得られる、硬化物。
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