JP2010111858A - 低架橋密度を有するフォトポリマー配合物 - Google Patents
低架橋密度を有するフォトポリマー配合物 Download PDFInfo
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- JP2010111858A JP2010111858A JP2009229372A JP2009229372A JP2010111858A JP 2010111858 A JP2010111858 A JP 2010111858A JP 2009229372 A JP2009229372 A JP 2009229372A JP 2009229372 A JP2009229372 A JP 2009229372A JP 2010111858 A JP2010111858 A JP 2010111858A
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- Prior art keywords
- photopolymer formulation
- photopolymer
- acrylate
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- Prior art date
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- 238000009472 formulation Methods 0.000 title claims abstract description 68
- 238000004132 cross linking Methods 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 239000011159 matrix material Substances 0.000 claims abstract description 34
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- 230000005855 radiation Effects 0.000 claims abstract description 20
- 229920000620 organic polymer Polymers 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 239000002243 precursor Substances 0.000 claims abstract description 11
- 239000006185 dispersion Substances 0.000 claims abstract description 4
- 150000003077 polyols Chemical class 0.000 claims description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 35
- 229920005862 polyol Polymers 0.000 claims description 33
- 239000012948 isocyanate Substances 0.000 claims description 25
- 150000002513 isocyanates Chemical class 0.000 claims description 25
- 230000003287 optical effect Effects 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 229920005906 polyester polyol Polymers 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 11
- 229920001400 block copolymer Polymers 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 9
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 9
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- 239000004417 polycarbonate Substances 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
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- 230000009471 action Effects 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 2
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 3
- -1 silver halide Chemical class 0.000 description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 14
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 11
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- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000005846 sugar alcohols Polymers 0.000 description 10
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000004814 polyurethane Substances 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000003118 aryl group Chemical class 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- 230000001588 bifunctional effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- 238000010538 cationic polymerization reaction Methods 0.000 description 4
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- SQHOAFZGYFNDQX-UHFFFAOYSA-N ethyl-[7-(ethylamino)-2,8-dimethylphenothiazin-3-ylidene]azanium;chloride Chemical compound [Cl-].S1C2=CC(=[NH+]CC)C(C)=CC2=NC2=C1C=C(NCC)C(C)=C2 SQHOAFZGYFNDQX-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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Abstract
【解決手段】マトリックスとして3次元架橋した有機ポリマー(A)またはその前駆体、該マトリックス中の溶液または分散液として存在し、化学線の作用下での重合によってエチレン性不飽和化合物と反応する基を含む化合物(B)、および(C)少なくとも1つの光開始剤を含んでなるフォトポリマー配合物であって、該3次元架橋した有機ポリマーのネットワーク密度が、2つのポリマー鎖を架橋するセグメントの平均分子量MCとして表して、少なくとも2685g/モルであるフォトポリマー配合物によって上記課題を解決する。
【選択図】なし
Description
[2つの平面波の重なりによって体積ホログラムを書込んだときに生じる屈折率コントラストΔnは、以下の屈折率変化:n(x)=n0+Δn・cos(K・x)によって得られる;ここで、Kは、x軸の方向に示す格子ベクトルの大きさを表し、n0は平均屈折率を表す。例えば、非特許文献5を参照。]
本発明の別の態様は、分子量MCと(B)の数平均分子量MMoとの比Qが3.30を超える上記フォトポリマー配合物である。
本発明の別の態様は、比Qが10.00を超える上記フォトポリマー配合物である。
本発明の別の態様は、3次元架橋した有機ポリマーが、イソシアネート成分(a)およびイソシアネート反応性成分(b)から構成される上記フォトポリマー配合物である。
本発明の別の態様は、(A)が、イソシアネート成分(a)およびイソシアネート反応性成分(b)を含んでなる上記フォトポリマー配合物である。
本発明の別の態様は、化合物(B)が、放射線硬化性基としてアクリレートおよび/またはメタクリレート基を含んでなる上記フォトポリマー配合物である。
本発明のさらに別の態様は、上記媒体から製造した光学素子、画像または提示である。
本発明のさらに別の態様は、化学線によって書込みモノマーを選択的に重合させることを含んでなる上記媒体の暴露方法である。
さらに本発明は、本発明のフォトポリマー配合物から得られるホログラフィック媒体に関する。
特に好ましい3次元架橋した有機ポリマーは、前駆体としてイソシアネート成分(a)およびイソシアネート反応性成分(b)から構成されるものである。
適するさらに高官能のアルコールは、ジトリメチロールプロパン、ペンタエリトリトール、ジペンタエリトリトールまたはソルビトールである。
イソシアヌレートおよび/またはイミノオキサジアジンジオン構造を有するHDIに基づくポリイソシアネートを使用するのが特に好ましい。
本発明におけるイソシアネート反応性基とは、好ましくはヒドロキシル、アミノまたはチオール基であり、ヒドロキシ化合物が特に好ましい。
適する有機カーボネートは、ジメチル、ジエチルおよびジフェニルカーボネートである。
適する環式エーテルは、例えば、スチレンオキシド、エチレンオキシド、プロピレンオキシド、テトラヒドロフラン、ブチレンオキシド、エピクロロヒドリンおよびこれらの任意の混合物である。
ポリエステルポリオールに関連して挙げたOH官能価>2を有する多価アルコールおよび第一または第二アミンおよびアミノアルコールを、開始剤として使用することができる。
適するさらに高官能のアルコールは、ジトリメチロールプロパン、ペンタエリトリトール、ジペンタエリトリトールまたはソルビトールである。
さらに、イソシアネート反応性成分(b)の官能基がイソシアネート成分(a)の官能基に対してモル過剰で存在する組合せも好ましい。
屈折率nD 20が1.54を超える、好ましくは1.55を超える、特に好ましくは1.58を超える上記した種類の化合物を、(B)において使用するのが好ましい。
分子量が1500g/モル未満、特に好ましくは1000g/モル未満である上記した種類の化合物を、(B)において使用するのが好ましい。
Rは、互いに独立して、それぞれ放射線硬化性基であり;そして
Xは、互いに独立してそれぞれ、RとC=Oの間の単結合、あるいは、ヘテロ原子を含有することもあり、そして/または官能基によって置換されていることもある直鎖、分岐鎖または環式の炭化水素基である]。
原則的に、R基の炭素結合した水素原子の1つまたはそれ以上を、C1〜C5アルキル基によって置換することもできるが、これは好ましくない。
好ましいポリオキシアルキレン基は、10個まで、好ましくは8個までの各オキシアルキレン基の反復単位を有する。
各X基中の反復単位は、完全にまたは部分的に、ブロックとしてまたはランダムに分布して存在することができる。
従って、本発明のフォトポリマー配合物は、ホログラフィック媒体およびホログラフィックフォトポリマーフィルムの製造に極めて適している。
従って、本発明は、本発明の媒体を暴露する方法であって、書込みモノマーを化学線によって選択的に重合させる方法にも関する。
本発明を具体化するある種の特定の構成を示しかつ説明したが、各部分の様々な修飾および再配列を、基礎となる本発明のコンセプトの思想および範囲から逸脱することなく為しうること、および本発明が本明細書中に示しかつ説明した特定の形態に限定されないことは、当業者には明らかであろう。
光重合可能モノマーの屈折率の測定
透過および反射スペクトルから、試料の波長の関数として屈折率nを得た。この目的のために、試料の約100〜300nm厚みのフィルムを、酢酸ブチル中の希溶液からスピンコーティングによって石英ガラス支持体に塗布した。この層パケットの透過および反射スペクトルを、分光計(STEAG ETA-Optikから、CD測定系ETA-RT)を用いて測定し、次いで、nのスペクトル曲線および層厚みを、測定した透過および反射スペクトルに適合させた。これは分光計の内部ソフトウエアを用いて行った(これには石英ガラス基材の屈折率データがさらに必要であり、これを予めブランク測定において測定した)。屈折率nMoは、ナトリウム灯の波長589nmに関連し、従ってnD 20に対応する。
屈折率nMaを測定するためのフォトポリマーマトリックスを製造するために、イソシアネート反応性成分(b)を60℃に加熱した(適切であれば)。次いで、イソシアネート成分(a)を加え、Speedmixer(Hauschildから)中で1分間混合した。次いで、成分(c)の溶液を加え、Speedmixer中で再び1分間混合した。成分(c)の溶液は、N-エチルピロリドン中で10重量%であった。溶液の対応する使用量は表1に見ることができる。なお液体である配合物を、ナイフ塗布によってガラスプレートに所望の厚みで塗布した。
「性能パラメーターEおよびΔnを測定するための、光開始剤を含むフォトポリマー配合物に基づくホログラフィック媒体の製造」の項に記載したようにして製造した媒体について、次いでそのホログラフィック特性を、図1に従う測定配置により、次のように試験した。
図1は、λ=633nm(He-Neレーザー)におけるHMTの幾何を示す:M=鏡、S=シャッター、SF=空間フィルター、CL=コリメーターレンズ、λ/2=λ/2プレート、PBS=偏光感受性のビームスプリッター、D=検出器、I=虹彩絞り、α=21.8°、β=41.8°[これらは、試料(媒体)の外側で測定した可干渉性ビームの入射角である]。
・暴露時間tの間、両シャッター(S)を開いた。
・次いで、シャッター(S)を閉じながら、媒体のなお未重合の書込みモノマーを5分間拡散させた。
プラトーモジュラスG0を測定するためのフォトポリマー配合物を製造するために、成分(B)および所望により添加剤を、所望により60℃でイソシアネート反応性成分(b)に溶解した。所望により、乾燥オーブン中で10分間までの60℃への加熱を行った。次いで、イソシアネート成分(a)を加え、Speedmixer中で1分間混合した。次いで、酢酸ブチル中の成分(c)の溶液を加え、Speedmixer中で再び1分間混合した。酢酸ブチル中の成分(c)の濃度は10重量%であった。この溶液を、表2に記載した量で使用した。
・プレート間隔250μm;
・一定の円振動数ω0 10rad/秒および調節した変形の大きさ1%における振動測定モード;
・温度50℃、標準の力調節 0ニュートン設定;
・少なくとも2時間の測定時間にわたって、またはG'の一定値Gmaxに到達するまで貯蔵モジュラスG'を記録する。
・円振動数範囲0.5rad/秒<ω<300rad/秒および調節した変形の大きさ1%における振動測定モード;
・温度50℃、標準の力調節 0ニュートン設定;
・円振動数ωにわたって貯蔵モジュラスG'を記録する。
図3は、マトリックスネットワーク硬化の曲線(左)およびプラトー挙動の試験(ωとは無関係のG')(右)を示す。
小さいプラトーモジュラスG0または2つのポリマー鎖を架橋するセグメントの大きい平均分子量MCは、低架橋密度を有するネットワークを特徴付ける。
DesmodurR XP 2410は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、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である;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%(成分a1)。
DesmodurR XP 2580は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、ヘキサンジイソシアネートに基づく脂肪族ポリイソシアネートである;NCO含量:約20%(成分a2)。
DesmodurR XP 2599は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、Acclaim 4200に基づくヘキサンジイソシアネートの全アロファネートである;NCO含量:5.6〜6.4%(成分a3)。
成分(4a)は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、ヘキサンジイソシアネートおよびAcclaim 4200のウレタンである;NCO含量:18.5%。
初めに、ヘキサメチレンジイソシアネート(HDI)(315.0g)を、丸底フラスコに撹拌しながらおよびN2を通気しながら導入し、二塩化イソフタロイル(0.016g)およびジブチルスズジラウレート(2滴、約0.040g)を加えた。この混合物を100℃に加熱し、Acclaim 4200(数平均分子量4000g/モルのポリプロピレンオキシド)(478.68g)を75分間で加えた。NCO値が18.5%に到達するまで撹拌を続けた。次いで、室温まで冷却することによって反応を停止させた。次いで、過剰のHDIを、140℃における薄膜蒸発器による蒸留によって分離した(HDIの残留<0.1%)。生成物が無色液体として得られた。これは、部分的にアロファネート構造を有し、平均官能価が約2.6である。
ポリオール(b1)の製造
ポリオール(b1)は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、TerathaneR 650とε-カプロラクトンのブロックコポリマーである。
初めに、亜鉛オクタノエート(0.25g)、ε-カプロラクトン(172.29g)および2官能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)(27.46g)を、1Lフラスコに導入し、150℃に加熱し、固体含量(非揮発性成分の割合)が99.5重量%またはそれ以上になるまで、該温度で維持した。次いで、冷却を行い、生成物を粘稠液体として得た。
ポリオール(b2)は、Bayer MaterialScience AG(Leverkusen、独国)の実験生成物であり、TerathaneR 1000とε-カプロラクトンのブロックコポリマーである。
初めに、亜鉛オクタノエート(0.18g)、ε-カプロラクトン(374.8g)および2官能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)(374.8g)を、1Lフラスコに導入し、120℃に加熱し、固体含量(非揮発性成分の割合)が99.5重量%またはそれ以上になるまで、該温度で維持した。次いで、冷却を行い、生成物をワックス状固体として得た。
ポリオール(b4)は、エチレンオキシドとプロピレンオキシドの2官能コポリエーテルであり、全体として50%割合のエチレンオキシドを含み、当量984.2g/モルを有する。
TerathaneR 1000(3.621kg)を、撹拌機を装備した20Lの反応タンクに計量導入し、DMC触媒(525mg)を加えた。次いで、約70rpmで撹拌しながら105℃に加熱した。3回にわたる真空の適用と窒素による真空の排除によって、空気を窒素に交換した。撹拌機の速度を300rpmに高めた後、真空ポンプを運転しながら約0.1バールの圧力で54分間にわたり、窒素を下部から混合物に通した。次いで、窒素により圧力を0.2バールにし、重合開始のためにプロピレンオキシド(PO)(363g)を導入した。これにより、圧力が2.42バールに上昇した。7分後に、圧力が再び0.34バールに低下し、さらにPO(11.379kg)を、2時間29分間にわたり2.9バールで計量導入した。PO導入の終了から47分後に、1.9バールの残留圧力において真空を適用し、完全な脱ガスを行った。生成物を、Irganox 1076(7.5g)の添加によって安定化し、無色の粘稠液体(OH価:27.6mgKOH/g、25℃での粘度:1498mPas)として得た。
出発物質であるDMC触媒は、欧州特許出願公開第700949号に記載される方法によって得られる、亜鉛ヘキサシアノコバルテート(III)に基づく2金属シアニド触媒である。
FomrezR UL28:ウレタン化触媒、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(Wilton、CT、米国)の市販製品(N-エチルピロリドン中の10%濃度溶液として使用)(成分c1)。
成分(B1):エトキシル化(3)ビスフェノールAジアクリレート
屈折率nD 20=nMoが1.543(製造元データシートの情報)。
屈折率nMoは1.603である。
屈折率nMoは1.579である。
屈折率nMoは1.576である。
系:ニューメチレンブルー+CGI(成分C1)の説明
ニューメチレンブルー(0.1g)、CGI 909(Ciba Inc.の実験生成物、Basel、スイス国)(1.00g)を、暗所でまたは適当な照明のもとで、ビーカー中のN-エチルピロリドン(3.50g)に溶解した。この溶液の対応する重量%(表3を参照)を、試料媒体の製造に使用した。
サフラニンO(0.1g)、CGI 909(Ciba Inc.の実験生成物、Basel、スイス国)(1.00g)を、暗所でまたは適当な照明のもとで、ビーカー中のN-エチルピロリドン(3.50g)に溶解した。この溶液の対応する重量%(表3を参照)を、試料媒体の製造に使用した。
表1は、正確な組成を記載するものである。
表1は、589nmにおいて屈折率nMaを測定するためのマトリックス成分(A)を示す。NCO:OHは、それぞれの成分(A)中の成分(a)および(b)の官能基の当量数の比を示す。
表2は、プラトーモジュラスG0を測定するためのフォトポリマー配合物の研究した例を挙げるものである(これらは、その組成に排他的な特徴を有さない)。これらのフォトポリマー配合物を、「振動レオメーターによるフォトポリマーnプラトーモジュラスG0の測定」の項に記載した方法に従って調製した。
フォトポリマー配合物をホログラフィック媒体(表3を参照)の製造に使用した。その際に、フォトポリマーを、それぞれ1mm厚みのガラスプレート間の層として製造した。この種のホログラフィック媒体は、その性能を「反射配置での2ビーム干渉によるホログラフィック媒体のホログラフィック特性DEおよびΔnの測定」の項に記載した方法によって測定するのに特に適するものであり、従って、特許請求の範囲の記載に関連して、使用したフォトポリマー配合物がプラトーモジュラスG0および/またはQ=MC/MMoの点で特許請求の範囲に記載した特性を満たしているなら、該ホログラフィック媒体への限定を意味するものではない。
ホログラフィック媒体を製造するために、成分(B)、成分(C)[これは成分(B)に予め溶解しておいてもよい]および所望により添加剤を、暗所において、所望により60℃でイソシアネート反応性成分(b)に溶解し、次いで、20μmのガラスビーズ(例えば、Whitehouse Scientific Ltdから、Waverton、Chester、CH3 7PB、英国)を加え、十分に混合した(Speedmixer)。所望により、乾燥オーブン中、60℃で10分間以下の加熱を行った。次いで、イソシアネート成分(a)を加え、Speedmixer中で再び1分間の混合を行った。次いで、成分(c)の溶液を加え、Speedmixer中で再び1分間の混合を行った。得られた混合物を、撹拌しながら<1mバールで30秒間以下の脱ガスにかけ、次いで、これを50×75mmのガラスプレート上に広げ、そのそれぞれを別のガラスプレートで覆った。PU配合物の硬化は、15kg重量下で数時間かかって起こった(通常は一晩)。一部の場合に、光の入らないパッケージ中、60℃でさらに2時間、媒体を後硬化させた。異なる初期粘度および異なる硬化速度のマトリックスを有する異なる配合物は、常に同じ層厚みdのフォトポリマー層を導く訳ではないので、各試料のために書込んだホログラムの特性とは独立してdを測定した。
用量E(mJ/cm2)において、G0(MPa)、MC(g/モル)、Q=MC/MMoおよびΔnに対して以下の測定値が得られた。これらを表4に示す。
表4は、選択した例の評価を示すものである。*を付した値は、λ=633nmを用いる代わりにλ=532nmを用いて測定した。
Claims (14)
- マトリックスとして3次元架橋した有機ポリマー(A)またはその前駆体、該マトリックス中の溶液または分散液として存在し、化学線の作用下での重合によってエチレン性不飽和化合物と反応する基を含む化合物(B)、および(C)少なくとも1つの光開始剤を含んでなるフォトポリマー配合物であって、該3次元架橋した有機ポリマーのネットワーク密度が、2つのポリマー鎖を架橋するセグメントの平均分子量MCとして表して、少なくとも2685g/モルであるフォトポリマー配合物。
- 3次元架橋した有機ポリマーのネットワーク密度が、7500〜55000g/モルの範囲内である請求項1に記載のフォトポリマー配合物。
- 分子量MCと(B)の数平均分子量MMoとの比Qが3.30を超える請求項1に記載のフォトポリマー配合物。
- 比Qが10.00を超える請求項3に記載のフォトポリマー配合物。
- 3次元架橋した有機ポリマーがウレタン基を含む請求項1に記載のフォトポリマー配合物。
- 3次元架橋した有機ポリマーが、イソシアネート成分(a)およびイソシアネート反応性成分(b)から構成される請求項1に記載のフォトポリマー配合物。
- (A)が、イソシアネート成分(a)およびイソシアネート反応性成分(b)を含んでなる請求項1に記載のフォトポリマー配合物。
- 成分(a)が、イソシアヌレートおよび/またはイミノオキサジアジンジオン構造を有するHDIに基づくポリイソシアネート、あるいは、HDIおよび/またはTMDIとポリエーテルポリオール、ポリエステルポリオールおよび/またはポリカーボネートポリオールとに基づくアロファネートおよび/またはウレタン構造を有するNCO官能価2〜5のプレポリマーを含んでなる請求項7に記載のフォトポリマー配合物。
- 成分(b)が、OH官能価が1.5〜6であり、数平均分子量が200〜18000g/モルである、ポリプロピレンオキシド、ポリエチレンオキシドおよび/またはこれらのランダムまたはブロックコポリマーの形態での組合せおよび/またはモノマー単位としてテトラヒドロフラン、ブチレンオキシドまたはε-カプロラクトンをさらに含む上記した種類のブロックコポリマーを含んでなる請求項7に記載のフォトポリマー配合物。
- 化合物(B)が、1.54を超える屈折率nD 20を有する請求項1に記載のフォトポリマー配合物。
- 化合物(B)が、放射線硬化性基としてアクリレートおよび/またはメタクリレート基を含んでなる請求項1に記載のフォトポリマー配合物。
- 請求項1に記載のフォトポリマー配合物から製造した視覚ホログラムの記録に適する媒体。
- 請求項12に記載の媒体から製造した光学素子、画像または提示。
- 化学線によって書込みモノマーを選択的に重合させることを含んでなる請求項12に記載の媒体の暴露方法。
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JP2013543149A (ja) * | 2010-11-08 | 2013-11-28 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 高架橋マトリックスポリマーを有する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 |
JP2017037315A (ja) * | 2010-11-08 | 2017-02-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 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 |
KR101804608B1 (ko) * | 2010-11-08 | 2017-12-04 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 고도로 가교된 매트릭스 중합체를 갖는 홀로그래픽 매체의 제조를 위한 광중합체 배합물 |
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Also Published As
Publication number | Publication date |
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RU2515991C2 (ru) | 2014-05-20 |
TWI477525B (zh) | 2015-03-21 |
ATE517139T1 (de) | 2011-08-15 |
US20100087564A1 (en) | 2010-04-08 |
BRPI0903847B1 (pt) | 2019-04-30 |
KR101680894B1 (ko) | 2016-11-29 |
RU2009136169A (ru) | 2011-04-10 |
JP5544136B2 (ja) | 2014-07-09 |
TW201033241A (en) | 2010-09-16 |
CN101713923A (zh) | 2010-05-26 |
SG160313A1 (en) | 2010-04-29 |
CA2680974A1 (en) | 2010-04-01 |
US9505873B2 (en) | 2016-11-29 |
EP2172504A1 (de) | 2010-04-07 |
EP2172504B1 (de) | 2011-07-20 |
BRPI0903847A2 (pt) | 2010-07-20 |
RU2515991C9 (ru) | 2015-02-20 |
KR20100037557A (ko) | 2010-04-09 |
IL200996A0 (en) | 2010-06-30 |
CN101713923B (zh) | 2014-05-07 |
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