JP6244204B2 - ホログラフィック媒体を製造するためのフォトポリマー処方物 - Google Patents
ホログラフィック媒体を製造するためのフォトポリマー処方物 Download PDFInfo
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- JP6244204B2 JP6244204B2 JP2013537147A JP2013537147A JP6244204B2 JP 6244204 B2 JP6244204 B2 JP 6244204B2 JP 2013537147 A JP2013537147 A JP 2013537147A JP 2013537147 A JP2013537147 A JP 2013537147A JP 6244204 B2 JP6244204 B2 JP 6244204B2
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- photopolymer formulation
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- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
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Description
低屈折率の適当なマトリックスポリマーは、例えばポリオール成分とポリイソシアネート成分との反応により得られるポリウレタンである。
で示される化合物であり得る。
上記ジ−、トリ−またはポリイソシアネートの混合物を用いることも可能である。
適当なジ−、トリ−またはポリイソシアネートの例は、ブチレンジイソシアネート、ヘキサメチレンジイソシアネート(HDI)、イソホロンジイソシアネート(IPDI)、1,8−ジイソシアナト−4−(イソシアナトメチル)オクタン、2,2,4−および/または2,4,4−トリメチルヘキサメチレンジイソシアネート、異性体ビス(4,4’−イソシアナトシクロヘキシル)メタンおよびこれらの任意の所望の異性体含有量を有する混合物、イソシアナトメチル−1,8−オクタンジイソシアネート、1,4−シクロヘキシレンジイソシアネート、異性体シクロヘキサンジメチレンジイソシアネート、1,4−フェニレンジイソシアネート、2,4−および/または2,6−トルエンジイソシアネート、1,5−ナフチレンジイソシアネート、2,4’−または4,4’−ジフェニルメタンジイソシアネート、1,5−ナフチレンジイソシアネート、m−メチルチオフェニルイソシアネート、トリフェニルメタン−4,4’,4’’−トリイソシアネートおよびトリス(pイソシアナトフェニル)チオホスフェートまたはウレタン、ウレア、カルボジイミド、アシルウレア、イソシアヌレート、アロファネート、ビウレット、オキサジアジントリオン、ウレットジオンまたはイミノオキサジアジン構造を有するこれらの誘導体およびこれらの混合物である。芳香族または芳香脂肪族ジ−、トリ−またはポリイソシアネートが好ましい。
水吸収は、式(F−1):
W=(mf/mt−1)×100% (F−1)
〔式中、mfは、水飽和後の染料の質量であり、およびmtは、乾燥染料mtの質量である。mtは、例えば高温にて真空で、染料の特定の量を一定の質量へ乾燥することにより確認される。mfは、空気中で規定湿度にて放置した染料の特定の量を一定重量とすることにより決定する。〕
から明らかである。
RSnL3 (II)
〔式中、
Rは、任意にヘテロ原子、特に酸素で、鎖中においても置換された1〜30個の炭素原子の直鎖状または分枝状アルキル基であり、および
Lはそれぞれ、互いに独立して、−O2C−R3基
〔式中、R3は、炭素原子1〜30個の直鎖状またはアルキル基であり、これは、任意に、鎖中においても、ヘテロ原子、特に酸素、炭素原子2〜30個のアルケニル基または任意の所望の置換または非置換の任意にヘテロ原子を有するまたは有さない多環式芳香族環で置換されている〕
で示される化合物を含み得る。
Bi(III)M3 (III)、
または一般式(IV):
Sn(II)M2 (IV)
〔式中、Mは、互いに独立して、−O2C−R4〔式中、R4は、飽和または不飽和またはヘテロ原子置換C1−〜C19−アルキル基またはC2−〜C19アルケニル基、特にC6−〜C11−アルキル基、より好ましくはC7−〜C9−アルキル基であり、または任意に芳香族的にまたは酸素または窒素で任意の所望の形態で置換されたC1−〜C18−アルキル基であり、Mは、式(III)および(IV)において同じ意味を有する必要はない〕
で示される化合物である。
FeQ3 (V)
〔式中、Qは、互いに独立して、式(Va):
で示される有機アニオンである〕
で示される化合物である。
R8が、非置換または必要に応じてヘテロ原子、例えばフッ素等で置換された直鎖状、分枝状、環式または複素環式有機基であることは特に好ましい。〕
を有し得る。
10〜84.999重量%のポリオール成分a)、
2〜30重量%のポリイソシアネート成分b)、
10〜60重量%の書込モノマーB)、
0.001〜10重量%の光開始剤C)、
0.001〜4重量%の触媒c)、および任意に
0〜30重量%の可塑剤D)
を含み得る。ここで重量%トリオールは常に100重量%まで添加する。
25〜70重量%のポリオール成分a)、
5〜25重量%のポリイソシアネート成分b)、
25〜50重量%の書込モノマーB)、
0.01〜5重量%の光開始剤C)、
0.01〜2重量%の触媒c)、および任意に
0〜25重量%の可塑剤D)
を含み、ここで重量%トリオールは常に100重量%まで添加する。
(I)本発明のフォトポリマー処方物を全ての成分を混合することにより調製し、
(II)フォトポリマー処方物を、加工温度においてホログラフィック媒体のための所望の形態へ加工し、および
(III)所望の形態でウレタン形成により加工温度を超える架橋温度において硬化する、
ホログラフィック媒体の製造方法を提供する。
次のものを含むフォトポリマー処方物:
・ポリイソシアネート成分a)、および
イソシアネート反応性ポリオール成分b)
から前駆体として構成され、および
触媒c)を用いて3次元架橋された
3次元架橋有機マトリックスポリマーA)、
・放射線への暴露によりエチレン性不飽和化合物と重合により反応する基(放射線硬化性基)を有し、マトリックスポリマー中に溶解または分散状態で存在する書込モノマーB)
・光開始剤C)
・任意に可塑剤D)
・任意に溶媒d)、
任意にフリーラジカル安定剤、添加剤および他の助剤および/または添加剤E)。
OH価
記載のOH価は、DIN 53240−2に従って決定した。
記載のNCO値(イソシアネート含有量)は、DIN EN ISO 11909に従って決定した。
分子量は、ゲルパーミエーションクロマトグラフ法(GPC)を用いて決定した。
Mp1000000〜162の分子量を有するポリスチレン標準を校正に用いる。
分析のためのテトラヒドロフランを溶離剤として用いる。
以下のパラメーターを、繰り返し測定において維持する:
脱気:オンライン脱気装置
流速:
1ml/分
分析時間:
45分
検出器:屈折系およびUV検出器
射出体積:
100μL〜200μL
粘度を測定すべき成分または混合物は、特記のない限り、20℃にて、レオメーターのコーン−プレート測定系(Anton Paar PhysicaからのMCR 51)中で適用した。測定は、以下の条件下で行った:
・測定体:コーンCP25、d=25mm、角度=1度
・コーンおよびプレート間の距離としての測定ギャップ:0.047 mm
・測定時間:10秒
・250L/秒のせん断速度における粘度の決定
固形分は、IRはかりの取扱説明書に従って、約1gの物資を使い捨て可能なアルミニウム皿へ塗布し、140℃にて、30秒間一定重量となるまで加熱するか、または約1gの物質を特別な使い捨て可能なアルミニウム皿(最大溶媒含有量10重量%を有する系に適当である)へ塗布し、125℃にて60分間、乾燥棚において加熱することにより決定した。適当な曲げペーパークリップを用いて決定すべき物質を分配し、フィルムの均質な乾燥を確保した。ペーパークリップは、測定の間残し、初期重量において考慮される必要があった。
ゲルポイントGGelおよびtGelおよび活性化温度TAktを、光開始剤を有さない処方物について、光開始剤については測定の必要がなく、ゲルポイントGGelおよびtGelおよびTAktは、処方物中の光開始剤の存在により影響を受けないので決定した。
ゲルポイントGGelおよびtGelを決定するためのフォトポリマー処方物を、成分B)、任意にポリオール成分b)中に添加剤を溶解することにより調製した。乾燥棚中で60℃にて加熱することは、最大10分間に限定した。加熱することは、成分が既に液体である場合に不溶であった。次いでポリイソシアネート成分a)を1分間スピードミキサー中で混合しながら添加した。次いで、成分c)の溶液を、成分d)に、1分間スピードミキサー中で再び混合しながら添加した。成分c)の濃度は、成分d)中において5または10重量%であった。この溶液は、表1として記載の量に用いた。
・プレート間隔250μm
・10Hzの一定の角振動数および10%の調節変形振幅における振動モード
303Kまたは313Kまたは328Kまたは343Kまたは353Kにおける温度T0ニュートンに設定した垂直力調節
・測定時間tにわたる、少なくとも時間tGelにおけるゲル点の条件G’=G’’=GGelに達するまでの貯蔵弾性率G’および損失弾性率G’’の記録。
ゲル時間TAktは、マトリックスが硬化する高温では、触媒(成分c)はより活性であるので温度に依存する。従って、tGelを異なった温度Tにおいて1つおよび同じフォトポリマー処方物について決定した。次いで、tGelについて得た値を、1/Kで与えられる対応する絶対温度の逆数1/Tに対してプロットした。これについてy軸の対数スケールを選択し、線形依存性を得、これは、以下:
物理層厚みを、市販の白色光干渉計、Ingenieursbuero FuchsからのFTM−Lite NIR層厚み測定装置を用いて決定した。
用いたポリイソシアネート成分a)
イソシアネート成分1(成分a1)、Desmodur N 3900は、Bayer MaterialScience AG(レーバークーゼン、独国)からの生成物であり、ヘキサンジイソシアネートに基づくポリイソシアネート、イミノオキサジアジンジオンの割合少なくとも30%、NCO含量:23.5%である。
ポリオール1(成分b1)は、Bayer MaterialScience AG(レーバークーゼン、独国)からの生成物であり、その製法は、以下に記載する。
アクリレート1(成分B1)、[1072455−04−9]は、Bayer MaterialScience AG(レーバークーゼン、独国)からの生成物であり、その製法は、以下に記載する。
共開始剤1テトラブチルアンモニウムトリス(3−クロロ−4−メチルフェニル)(ヘキシル)ボレート、[1147315−11−4])は、BASF SE(バーゼル、スイス、2010年)から得られる生成物である。
非光重合性成分(成分D)は、Bayer MaterialScience AG(レーバークーゼン、独国)の生成物であり、その製法は、以下に記載する。
触媒1(成分c1):ウレタン化触媒Fomrez UL 28、ジメチルビス[(1−オキソネオデシル)オキシ]スタンナン、Momentive Performance Chemicals(ウィルトン、コネチカット州、米国)の市販生成物。
溶媒1(成分d1):N−エチルピロリドン
溶媒2(成分d2):酢酸ブチル
溶媒3(成分d3):酢酸エチル
BYK(登録商標)310:BYK−Chemie GmbH(ベーゼル、独国)からのシリコーン系表面添加剤(成分E1)(キシレン中25%濃度溶液)
ポリオール1(成分b1)の調製:
1Lフラスコ中に、まず、0.18gの錫オクトエート、374.8gのε−カプロラクトンおよび374.8gの二官能性ポリテトラヒドロフランポリエーテルポリオール(当量500g/モルOH)を投入し、120℃へ加熱し、120にて固形分(不揮発性物質の割合)が99.5重量%以上になるまで維持した。次いで、冷却して生成物をワックス状固体として得た。
2475gの2官能性ポリテトラヒドロフランポリエーテルポリオール(当量325g/モルOH)を、撹拌機を有する20リットル反応容器中へ投入し、452.6mgのDMC触媒を投入した。次いで温度を105℃まで約70rpmにて撹拌しながら昇温した。3回の真空を適用および窒素での放出により、空気を窒素に交換した。撹拌速度を300rpmへ上昇させた後、窒素を混合物へ57分間真空ポンプを動かしながら上方へ通過させ、圧力は約0.1バールの圧力であった。その後、0.5バールの圧力を窒素により確立し、100gのエチレンオキシド(EO)および150gのプロピレンオキシド(PO)連続的に導入して重合を開始した。圧力は2.07バールへ増加した。10分後、圧力を0.68バールへ再び低下させ、混合物として更なる5.116kgのEOおよび7.558kgのPOを1時間53分間にわたり2.34バールにて投入した。エポキシド計量の終了から31分後、完全な脱気のために、真空を2.16バールの残存圧にて適用した。生成物を、7.5gのIrganox1076の添加により安定化し、僅かに濁った粘性液体(OH価27.1mgKOH/g、25℃での粘度:1636mPas)を得た。
500m丸底フラスコ中に、まず、0.1gの2,6−ジ−tert−ブチル−4−メチルフェノール、0.05gのジブチル錫ジラウレート(Desmorapid(登録商標) Z、Bayer MaterialScience AG、レーベークーゼン、ドイツ)および213.07gの酢酸エチル中のトリス(p−イソシアナトフェニル)チオホスフェートの27%溶液(Desmodur(登録商標) RFE、Bayer MaterialScience AG、レーベークーゼン、ドイツからの生成物)を投入し、60℃へ加熱した。その後、42.37gの2−ヒドロキシエチルアクリレートを滴下し、混合物をイソシアネート含有量が0.1%未満に低下するまで更に60℃において維持した。次いで冷却し、酢酸エチルを減圧下で完全に除去して生成物を部分結晶性固体として得た。
まず、0.02gの2,6−ジ−tert−ブチル−4−メチルフェノール、0.01gのDesmorapid(登録商標)Z、11.7gの3−(メチルチオ)フェニルイソシアネートを100ml容丸底フラスコに投入し、60℃へ加熱した。続いて、8.2gの2−ヒドロキシエチルアクリレートを滴下し、混合物は、イソシアネート含有量が0.1%未満に低下するまで60℃にて更に保持した。次いで、冷却して生成物を淡黄色液体として得た。
暗い場所でまたは適当な照明の下で、0.10gの染料1、0.05gの染料2、0.05gの染料3、1.50gの共開始剤1を、3.50gのN−エチルピロリドンにビーカー中で溶解した。この溶液の適切な重量パーセントを、実施例媒体を製造するために用いた。
まず、0.02gのジブチルスズジラウレート(Desmorapid(登録商標)Z、Bayer MaterialScience AG、レーバークーゼン、独国)および3.6gの2,4,4−トリメチルヘキサン1,6−ジイソシアネート(TMDI)を50ml丸底フラスコに仕込み、60℃へ加熱した。続いて、11.9gの2,2,3,3,4,4,5,5,6,6,7,7−ドデカフルオロヘプチル)−1−オールを滴下し、混合物を、イソシアネート含有量が0.1%未満に低下するまで60℃で更に保持した。次いで冷却して生成物を無色油として得た。
表1は、その組成物についてのゲルポイントGGelおよびtGelおよび活性化温度TAktを決定するためのフォトポリマー処方物の研究例を記載する。これらのフォトポリマー処方物は、章「振動レオメーターを用いるフォトポリマーのゲルポイントGGelおよびtGelの測定」に記載の手順に従って調製した。
表2は、フォトポリマー処方物の活性化温度TAktの決定の結果を示す。
本発明のおよび本発明ではないフォトポリマー処方物からのフィルムの形態でのホログラフィック媒体の連続製造を記載する。
個々の部は、以下の参照記号を有する:
1 ストック用貯蔵容器
2 計量装置
3 真空脱気装置
4 フィルター
5 スタティックミキサー
6 コーティング装置
7 循環空気乾燥器
8 担体基材
9 カバー層
次いでこれらをフィルター4よりスタティックミキサー中へ通過させ、成分を混合してフォトポリマー処方物を形成する。次いで得られた液体を供給してコーティング装置6へ供給した。
上記の被覆装置によるフォトポリマー処方物からのホログラフィックフィルムの連続製造は、連続的な均質被覆物が得られる場合には、決定的に、第1に、フォトポリマー処方物のポットライフに依存し、第2に完全な架橋への反応時間に依存する。2つの態様を以下に説明する。
連続フィルムの製造における極めて重要な要因は、混合の開始から塗布の時点までのフォトポリマー処方物のポットライフである。適切な処理温度における極めて長いポットライフは、処方物のトラブルのない処理を確実とするので好ましい。
表2および3における結果は、活性化温度TAkt>8300Kを有する処方物は、室温にてコーティング装置中において長いポットライフを有する。これは、本発明のフォトポリマー処方物が、フィルムの形態でのホログラフィック媒体の効率的な大規模工業製造について極めて有用であることを意味する。
特定の条件、例えば特定の温度等における反応時間または滞留時間は、フォトポリマーの巻取性/非ブロック制、従って、このようなフォトポリマーフィルムの製造における製造速度について著しい影響を有する1つの重要な要因である。従って、架橋温度における短い反応時間が好ましい。
Claims (11)
- 10〜84.999重量%のポリオール成分、2〜30重量%のポリイソシアネート成分、10〜60重量%の書込モノマー、0.001〜10重量%の光開始剤および0.001〜4重量%触媒を含んでなり、活性化温度≧8300Kを有することを特徴とする、フォトポリマー処方物であって、
前記活性化温度は、ポリオール成分、ポリイソシアネート成分、書込モノマーおよび触媒を用いて混合物を調製し、混合物の貯蔵弾性率G’および損失弾性率G’’をいずれも測定時間tにわたり、少なくとも時間tGelにおけるゲル点の条件G’=G’’=GGelに達するまで決定し、温度T = 303K、313K、328K、343Kおよび353Kにてレオメーターのプレート−プレート測定系を、250μmのプレート間隔において振動モードにより10Hzの一定周波数fおよび10%の調節変形振幅において用い、tGel対tGelを決定した各絶対温度の逆数1/Tの対数プロットを行い、および線形回帰を用いて式:
前記ポリオール成分は、第1級OH基を有し;前記ポリイソシアネート成分は、第1級NCO基を有する脂肪族ポリイソシアネートまたはプレポリマーであり;前記書込モノマーは、少なくとも1つの単官能性および1つの多官能性ウレタン(メタ)アクリレートを含み、及び
前記触媒は、一般式(V):
FeQ 3 (V)
〔式中、Qは、互いに独立して、式(Va):
で示される有機アニオンである〕
を有する化合物から選択される、
該フォトポリマー処方物。 - 活性化温度は、≧8700Kであることを特徴とする、請求項1に記載のフォトポリマー処方物。
- ポリオール成分は、第1級OH基を有する2官能性ポリエーテル−またはポリエステルまたはポリエーテル−ポリエステルブロックコポリマーであることを特徴とする、請求項1または2に記載のフォトポリマー処方物。
- 光開始剤は、400〜800nmのスペクトル領域が吸収スペクトルにより少なくとも部分的に覆われている染料と、該染料へ適合した少なくとも1つの共開始剤との組み合わせを含むことを特徴とする、請求項1〜3のいずれかに記載のフォトポリマー処方物。
- ホログラフィック媒体の製造方法であって、
(I)請求項1〜4のいずれかに記載のフォトポリマー処方物を、全ての成分を混合することにより製造し、
(II)フォトポリマー処方物を、加工温度においてホログラフィック媒体のための所望の形態へ加工し、および
(III)所望の形態でウレタン形成により加工温度を超える架橋温度において硬化する、
製造方法。 - フォトポリマー処方物を、工程II)においてフィルムの形態へ処理することを特徴とする、請求項5に記載の方法。
- フォトポリマー処方物を、担体基材へ平坦に塗布することを特徴とする、請求項6に記載の方法。
- 処理温度は、≧15℃および≦40℃であることを特徴とする、請求項5〜7のいずれかに記載の方法。
- 架橋温度は、≧60℃および≦100℃であることを特徴とする、請求項5〜8のいずれかに記載の方法。
- 請求項1〜4のいずれかに記載のフォトポリマー処方物を含むホログラフィック媒体。
- インライン型ホログラム、二光束ホログラム、フルアパチャートランスファーホログラム、白色光透過型ホログラム、デニシュクホログラム、二光束反射ホログラムまたはエッジリットホログラムおよびホログラフィックステレオグラムから選択されるホログラムを製造するための、請求項10に記載のホログラフィック媒体の使用。
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US11226557B2 (en) | 2017-12-08 | 2022-01-18 | Lg Chem, Ltd. | Photopolymer composition |
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WO2012062658A1 (de) | 2012-05-18 |
US9098065B2 (en) | 2015-08-04 |
EP2638089B1 (de) | 2015-10-14 |
JP6329600B2 (ja) | 2018-05-23 |
JP2014503606A (ja) | 2014-02-13 |
CN103328526B (zh) | 2016-05-04 |
KR20130126908A (ko) | 2013-11-21 |
EP2450387A1 (de) | 2012-05-09 |
EP2638089A1 (de) | 2013-09-18 |
CN103328526A (zh) | 2013-09-25 |
KR101849811B1 (ko) | 2018-04-17 |
JP2017037315A (ja) | 2017-02-16 |
US20140038084A1 (en) | 2014-02-06 |
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