JP2014081423A - 体積ホログラム記録層形成用感光性組成物 - Google Patents
体積ホログラム記録層形成用感光性組成物 Download PDFInfo
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- JP2014081423A JP2014081423A JP2012227784A JP2012227784A JP2014081423A JP 2014081423 A JP2014081423 A JP 2014081423A JP 2012227784 A JP2012227784 A JP 2012227784A JP 2012227784 A JP2012227784 A JP 2012227784A JP 2014081423 A JP2014081423 A JP 2014081423A
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Abstract
【解決手段】下記成分(A)、成分(B)、及び成分(C)を、成分(B)の活性プロトンを有する官能基と成分(A)中の式(1)で表される化合物の脂環エポキシ基のモル比(前者/後者)が0.01〜0.3となる割合で含む三次元架橋ポリマーマトリックス前駆体材料と、ラジカル重合性化合物及びラジカル重合開始剤を含有する。成分(A):下記式(1)で表される化合物を含むカチオン重合性化合物、成分(B):活性プロトンを有する官能基を有する化合物、成分(C):熱酸発生剤
【選択図】なし
Description
本発明の他の目的は、耐湿性、熱安定性に優れ、ホログラム記録時(ホログラム形成時)の硬化収縮が抑制され、且つ多重記録特性に優れた体積ホログラム記録層を備える体積ホログラム記録媒体を提供することにある。
成分(A):下記式(1)で表される化合物を含むカチオン重合性化合物
成分(B):活性プロトンを有する官能基を有する化合物
成分(C):熱酸発生剤
成分(D):ラジカル重合性化合物
成分(E):ラジカル重合開始剤
本発明の体積ホログラム記録層形成用感光性組成物は、下記成分(A)、成分(B)、及び成分(C)を、成分(B)の活性プロトンを有する官能基と成分(A)中の式(1)で表される化合物の脂環エポキシ基のモル比(前者/後者)が0.01〜0.3となる割合で含む三次元架橋ポリマーマトリックス前駆体材料と、成分(D)及び成分(E)を含有する。
成分(A):式(1)で表される化合物を含むカチオン重合性化合物
成分(B):活性プロトンを有する官能基を有する化合物
成分(C):熱酸発生剤
成分(D):ラジカル重合性化合物
成分(E):ラジカル重合開始剤
(a1)分子内に脂環(脂肪族炭素環)を有するエポキシ化合物(但し、芳香環を有する化合物を除く)
(a2)分子内に芳香環を有するエポキシ化合物
(a3)分子内に芳香環及び脂環を有しないエポキシ化合物
本発明の成分(B)は活性プロトンを有する官能基を有する化合物である。前記活性プロトンを有する官能基は、カチオン硬化性を飛躍的に高める官能基であり、例えば、水酸基、カルボキシル基、リン酸基、チオール基、アミノ基等をあげることができる。本発明においては、なかでも、カチオン重合反応を促進する点で活性プロトンを有する官能基として水酸基を有する化合物が好ましい。活性プロトンを有する官能基を有する化合物は、その活性プロトンを有する官能基がカチオン重合末端に結合する事によりカチオン重合を停止させ、別の連鎖反応に重合を転移させる連鎖移動反応を引き起こすと考えられ、それにより得られるポリマーを低分子量化し、且つカチオン硬化性を高めると考えられる。
本発明の成分(C)は熱酸発生剤である。熱酸発生剤としては、成分(A)(カチオン重合性化合物)の熱カチオン重合を活性化する(開始させる)化合物であればよく、特に限定されないが、例えば、商品名「サンエイドSI−60L」、「サンエイドSI−80L」、「サンエイドSI−100L」、「サンエイドSI−110L」、「サンエイドSI−150L」(以上、三新化学工業(株)製)等の芳香族スルホニウム塩を好ましく用いることができる。
本発明の成分(D)はラジカル重合性化合物であり、分子内にラジカル重合性基(ラジカル重合可能な炭素−炭素不飽和二重結合を有する基)を1個以上有する化合物である。ラジカル重合性化合物としては光ラジカル重合性化合物が好ましく、少なくとも1つの付加重合可能なエチレン性不飽和二重結合を有する化合物(例えば、ビニル化合物、(メタ)アクリレート等の不飽和カルボン酸、前記不飽和カルボン酸の塩、前記不飽和カルボン酸と脂肪族多価アルコールとのエステル化合物、前記不飽和カルボン酸と脂肪族多価アミン化合物とのアミド化合物等)が好ましく用いられる。
本発明の成分(E)はラジカル重合開始剤である。成分(D)として光ラジカル重合性化合物を使用する場合には、光ラジカル重合開始剤が好ましく用いられる。光ラジカル重合開始剤としては、成分(D)の光ラジカル重合を活性化する(開始させる)化合物であればよく、例えば、1,2−オクタンジオン,1−[4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)](商品名「IRGACURE OXE01」、BASF社製)、エタノン,1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−,1−(0−アセチルオキシム)(商品名「IRGACURE OXE02」、BASF社製)等のオキシムエステル類;3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン(商品名「BTTB」、日油(株)製)、3,3’−ジ(t−ブチルパーオキシカルボニル)−4,4’−ジ(メトキシカルボニル)ベンゾフェノン、3,3’−ジ(メトキシカルボニル)−4,4’−ジ(t−ブチルパーオキシカルボニル)ベンゾフェノン、3,4’−ジ(t−ブチルパーオキシカルボニル)−3’,4−ジ(メトキシカルボニル)ベンゾフェノンの位置異性体混合物、t−ブチルパーオキシベンゾエート(商品名:「パーブチルZ」、日油(株)製)等の過酸化エステル類;t−ブチルヒドロパーオキシド、ジ−t−ブチルパーオキシド等の過酸化物類;ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル等のベンゾインやベンゾインアルキルエーテル類;アセトフェノン、2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノ−プロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン等のアセトフェノン類;2−メチルアントラキノン、2−エチルアントラキノン、2−t−ブチルアントラキノン、1−クロロアントラキノン、2−アミルアントラキノン等のアントラキノン類;2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−イソプロピルチオキサントン等のチオキサントン類;アセトフェノンジメチルケタール、ベンジルジメチルケタール等のケタール類;ベンゾフェノン等のベンゾフェノン類;キサントン類;1,7−ビス(9−アクリジニル)ヘプタン;ビス(η5−2,4−シクロペンタジエン−1−イル)−ビス(2,6−ジフルオロ−3−(1H−ピロール−1−イル)−フェニル)チタニウム(商品名「IRGACURE 784」、BASF社製)等のチタノセン化合物;芳香族ヨードニウム塩、芳香族スルホニウム塩等が挙げられる。これらは1種を単独で又は2種以上を組み合わせて使用できる。
本発明の体積ホログラム記録層形成用感光性組成物は上記成分以外にも、必要に応じて他の成分(例えば、増感色素、可塑剤等)を含有していてもよい。本発明においては、なかでも増感色素を含有することが好ましい。
本発明の体積ホログラム記録媒体は、上記体積ホログラム記録層形成用感光性組成物を加熱処理して得られる、三次元架橋ポリマーマトリックスと、成分(D)のラジカル重合性化合物と、成分(E)のラジカル重合開始剤を含有する体積ホログラム記録層を備える。
図1は、回折効率及び収縮率の測定に用いた光学系の概略図である。光源として532nm半導体レーザーを用い、ミラー(M)、スペーシャルフィルター(OL及びPh)、平凸レンズ(PCL)、波長板(PP)を介し、ビームスプリッター(BS)で2つの光に分けた。BSで分けられた2つの光をミラーを介し、サンプルに対してそれぞれ30°、30°で入射、干渉させた。回折光及び透過光の強度はパワーメーター(PM:(株)エーディーシー製)にてそれぞれ検出した。
二光束干渉法で記録したホログラムの回折効率をパワーメーターを用いて測定した。口径5φの532nm半導体レーザーを30°の角度で入射し、透過光と回折光を検出した。体積ホログラム記録媒体を−5°〜5°の範囲で軸回転させ、回折光強度が最も高くなる位置で回折効率ηを、下記式(2)を用いて算出した。
η=L1/(L0+L1) (2)
(透過光強度:L0、回折光強度:L1)
体積ホログラム記録媒体を10°傾けて設置し、記録光と参照光の角度をそれぞれ20°と40°でホログラム記録を行った。その後、参照光を40°の角度で入射させ、最大回折効率を示す角度を検出した(θ1)。収縮がない場合には、その際に得られる最大回折効率の示す角度は40°であるが、収縮が起こることで40°からのずれが生じる。また、同様にして、記録光のみを20°の角度で入射させ、最大回折効率を示す角度(θ2)を検出した。これらの角度を用いて、下記式(3)、(4)より記録媒体の厚み方向のグレーティングベクトル(K1およびK2)を求め、下記式(5)より硬化収縮率を算出した。尚、記録光と参照光の光源としては、回折効率の測定と同様のものを使用した。
K1=(2π/λ){(n2−sin2θ1)1/2)−(n2−sin2θ2)1/2)} (3)
(λ:記録波長、n:記録層の屈折率、θ1,θ2:記録前の入射角:40°,20°)
K2=(2π/λ){(n2−sin2θ1’)1/2)−(n2−sin2θ2’)1/2)} (4)
(λ:記録波長、n:記録層の屈折率、θ1’,θ2’:回折効率が最大となる入射角)
硬化収縮率(%)=(K1−K2)/K1×100 (5)
(記録前:K1、記録後:K2)
カチオン重合性化合物として3,4,3’、4’−ジエポキシビシクロヘキシル48重量部、及び2−エチルヘキシルビニルエーテル24重量部、活性プロトンを有する官能基を有する化合物としてイソプロパノール5.9重量部、熱酸発生剤としてトリフェニルスルホニウム塩(商品名「サンエイドSI−60L」、三新化学工業(株)製)0.8重量部(溶液としての量:固形分濃度32.3重量%)、ラジカル重合性化合物としてヒドロキシエチル化o−フェニルフェノールアクリレート(商品名「A−LEN−10」、新中村化学工業(株)製)24重量部、光ラジカル重合開始剤として3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン2.4重量部(溶液としての量:固形分濃度40重量%)、及び、増感色素としてシアニン色素0.08重量部を、室温下で配合及び撹拌し、各成分を均一に溶解させて、体積ホログラム記録層形成用感光性組成物を調製した。
表1に示す処方(単位は重量部)及び加熱条件に変更した以外は実施例1と同様にして体積ホログラム記録層形成用感光性組成物を調製し、体積ホログラム記録媒体を作成して、ダイナミックレンジ(M/#:1mm換算)及び硬化収縮率を測定した。尚、表1における光ラジカル重合開始剤(3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン)の配合量は、溶液(固形分濃度40重量%)の配合量で示した。同様に、表1における熱酸発生剤の配合量は、溶液(固形分濃度32.3重量%)の配合量で示した。結果を下記表にまとめて示す。
[カチオン重合性化合物]
a−1:3,4,3’,4’−ジエポキシビシクロヘキシル
a−2:2−エチルヘキシルビニルエーテル
[活性プロトンを有する官能基を有する化合物]
b−1:イソプロパノール
b−2:1,3ブタンジオール
b−3:アリルアルコール
b−4:ポリエチレングリコール 200
b−5:ポリエチレングリコール 400
b−6:ポリエチレングリコール 600
b−7:ネオペンチルグリコール
[熱酸発生剤]
c−1:トリフェニルスルホニウム塩(商品名「サンエイドSI−60L」、三新化学工業(株)製)
[ラジカル重合性化合物]
d−1:ヒドロキシエチル化o−フェニルフェノールアクリレート(商品名「A−LEN−10」、新中村化学工業(株)製)
[光ラジカル重合開始剤]
e−1:3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン(商品名「BTTB」、日油(株)製)
[増感色素]
f−1:シアニン色素(3-Ethyl-2-[3-(3-ethyl-5-phenyl-2-benzoxazolinylidene)propenyl]-5-phenylbenzoxazolium bromide)
Claims (3)
- 下記成分(A)、成分(B)、及び成分(C)を、成分(B)の活性プロトンを有する官能基と成分(A)中の式(1)で表される化合物の脂環エポキシ基のモル比(前者/後者)が0.01〜0.3となる割合で含む三次元架橋ポリマーマトリックス前駆体材料と、成分(D)及び成分(E)を含有する体積ホログラム記録層形成用感光性組成物。
成分(A):下記式(1)で表される化合物を含むカチオン重合性化合物
成分(B):活性プロトンを有する官能基を有する化合物
成分(C):熱酸発生剤
成分(D):ラジカル重合性化合物
成分(E):ラジカル重合開始剤 - 成分(A)として、更に、式(1)で表される化合物以外のエポキシ化合物、オキセタン化合物、及びビニルエーテル化合物からなる群より選択される少なくとも一種のカチオン重合性化合物を含有する請求項1に記載の体積ホログラム記録層形成用感光性組成物。
- 請求項1又は2に記載の体積ホログラム記録層形成用感光性組成物を加熱処理して得られる、三次元架橋ポリマーマトリックスと、成分(D)のラジカル重合性化合物と成分(E)のラジカル重合開始剤を含有する体積ホログラム記録層を備える体積ホログラム記録媒体。
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US14/435,614 US20150268629A1 (en) | 2012-10-15 | 2013-10-10 | Photosensitive composition for forming volume hologram recording layer |
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US20150268629A1 (en) | 2015-09-24 |
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