JP5893334B2 - 近赤外線吸収性合成樹脂組成物 - Google Patents
近赤外線吸収性合成樹脂組成物 Download PDFInfo
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- JP5893334B2 JP5893334B2 JP2011230412A JP2011230412A JP5893334B2 JP 5893334 B2 JP5893334 B2 JP 5893334B2 JP 2011230412 A JP2011230412 A JP 2011230412A JP 2011230412 A JP2011230412 A JP 2011230412A JP 5893334 B2 JP5893334 B2 JP 5893334B2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 4
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- 125000001544 thienyl group Chemical group 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
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- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 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
- 239000002245 particle Substances 0.000 description 1
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- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- MWFNQNPDUTULBC-UHFFFAOYSA-N phosphono dihydrogen phosphate;piperazine Chemical compound C1CNCCN1.OP(O)(=O)OP(O)(O)=O MWFNQNPDUTULBC-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
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- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 1
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- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
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- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- SPUXJWDKFVXXBI-UHFFFAOYSA-N tris(2-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)(C)C)OC1=CC=CC=C1C(C)(C)C SPUXJWDKFVXXBI-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
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- Compositions Of Macromolecular Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
しかしながら、これらの化合物の赤外線吸収能力は満足いくものではなく、また可視光線の領域に吸収波長を有するため、透明性が必要とされる用途や着色を嫌う用途には使用できなかった。特に、これらの近赤外線吸収色素を近赤外線吸収剤として使用する場合、熱可塑性樹脂等の合成樹脂と組み合わせて使用することが多く、その場合、樹脂との相溶性に問題があったり、可視光線の領域に吸収波長を有することに起因して樹脂の透明性を損なったり、着色の問題があったり、或いはその他にも樹脂の物性を損なったりする場合が多かった。このため、近赤外領域に最大吸収波長を有しながら、可視光領域の吸収が小さい化合物が必要とされていた。
まず、下記一般式(1)で表される近赤外線吸収剤について説明する。
このような5員環としては、シクロペンテン環、シクロペンタジエン環、イミダゾール環、チアゾール環、ピラゾール環、オキサゾール環、イソキサゾール環、チオフェン環、フラン環、ピロール環等が挙げられ、また6員環としては、シクロヘキサン環、シクロヘキセン環、シクロヘキサジエン環、ベンゼン環、ピリジン環、ピペラジン環、ピペリジン環、モルフォリン環、ピラジン環、ピロン環、ピロリジン環等が挙げられる。
はじめに、原料のインディゴ骨格を有する化合物から中間体を得る工程について説明する。本工程では、溶媒中、インディコ骨格を有する化合物と、アニリン骨格を有する化合物を、四塩化チタンと1,4−ジアザビシクロ[2.2.2]オクタン(DABCO)存在下で、反応させ中間体を得る。例えば、インディゴを原料とし、前記化合物No.1を合成するための中間体−1を合成する場合のスキームは、下記スキーム1のようになる。
また、使用するアニリン骨格を有する化合物の使用量は、インディゴ骨格を有する化合物1モルに対して、2モル以上必要であり、好ましくは3〜4モルである。
また、使用するDABCOの使用量は、インディゴ骨格を有する化合物1モルに対して、好ましくは8〜12モルである。
本工程では、前記の工程で得られた中間体を、溶媒中、合成しようとする金属のβ−ジケトナート錯体と反応させて、本発明の一般式(1)で表される近赤外線吸収剤を得る。
例えば、前記スキーム1で得られた中間体−1から、前記化合物No.1においてMがパラジウムである近赤外線吸収剤(化合物No.1−1)を得るためのスキームは下記スキーム2のようになる。
本発明の近赤外線吸収性合成樹脂組成物は、合成樹脂に、本発明の一般式(1)で表される近赤外線吸収剤を含有させたものである。
これらの合成樹脂は、分子量、重合度、密度、軟化点、溶媒への不溶分の割合、立体規則性の程度、触媒残渣の有無、原料となるモノマーの種類や配合比率、重合触媒の種類(例えば、チーグラー触媒、メタロセン触媒等)等に拘わらず使用することができる。
一般式(1)で表される近赤外線吸収剤の含有量が0.001質量部未満であると、十分な近赤外線吸収能が達成できなくなる可能性があり、逆に20質量部を超えると、使用量に見合う効果が得られず経済的でない上、可視領域での透明性が損なわれる可能性がある。
また各種溶媒中に前記一般式(1)で表される近赤外線吸収剤と前記合成樹脂を溶解又は分散して近赤外線吸収性合成樹脂組成物溶液を配合し使用してもよい。
前記フェノール系酸化防止剤は、合成樹脂100質量部に対して、好ましくは0.001〜10質量部、より好ましくは0.05〜5質量部が用いられる。
前記リン系酸化防止剤は、合成樹脂100質量部に対して、好ましくは0.001〜10質量部、より好ましくは0.05〜5質量部が用いられる。
前記チオエーテル系酸化防止剤は、合成樹脂100質量部に対して、好ましくは0.001〜10質量部、より好ましくは0.05〜5質量部が用いられる。
前記紫外線吸収剤は、合成樹脂100質量部に対して、好ましくは0.001〜30質量部、より好ましくは0.05〜10質量部が用いられる。
前記ヒンダードアミン系光安定剤は、合成樹脂100質量部に対して、好ましくは0.001〜30質量部、より好ましくは0.05〜10質量部が用いられる。
実施例1は、本発明の近赤外線吸収剤の合成例を示し、実施例2及び3は、本発明の近赤外線吸収剤を用いた近赤外線吸収性合成樹脂組成物及び近赤外線吸収材の製造例を示し、比較例1及び2は、比較の近赤外線吸収性合成樹脂組成物及び近赤外線吸収材の製造例を示し、評価例1は、実施例2及び3並びに比較例1及び2で得られた近赤外線吸収材の透明性の評価を示す。
100mlの四つ口フラスコに、アニリン0.6ml(6.6mmol)、ブロモベンゼン40ml、及びジアザビシクロオクタン2.1g(19mmol)を加え、アルゴン中で攪拌した。その後、四塩化チタンの1mol/lトルエン溶液4.8ml(4.8mmol)を滴下した。滴下終了後、インジゴ0.55g(2.1mmol)を加え10時間還流状態で反応させた。反応終了後、アセトンを加え、ろ過し、ろ液を濃縮し緑色粉末を得た。これをジクロロメタン及び水で油水分離を行い、有機相を濃縮することで、紺色粉末の下記構造の中間体−1を0.5g得た(収率58%)。
得られた濃緑色針状結晶について、FT−IR測定を行った。分析結果を下記に示す。下記結果により得られた粉末は、下記構造式の化合物No.1−1と同定された。
3200,1597,1578,1520,1489,1439,1373,1300,1196,1119
5mlメスフラスコに、ポリカーボネート(ユーピロンS−3000F(三菱エンジニアリングプラスチックス株式会社製))0.25g、実施例1で得られた化合物No.1−1の2.5mg、ジクロロメタンを入れ、十分溶解させた後、5mlまでメスアップし、近赤外線吸収性合成樹脂組成物溶液を得た。この溶液5mlをシャーレに取り、ゆっくりと乾燥させることにより、近赤外線吸収材である、厚さ40μmのポリカーボネート近赤外線吸収フィルムを得た。
得られたポリカーボネート近赤外線吸収フィルムの吸収スペクトルを〔図2〕に示す。得られたフィルムの最大吸収波長は917nm、化合物No.1−1に換算したモル吸光係数ε=1.7×104で、このフィルムは、近赤外線領域に良好な吸収を示した。
ポリカーボネートの替わりにポリメチルメタクリレート(PMMA)を使用し、フィルムの厚さを50μmとした以外は実施例2と同様にして、PMMA近赤外線吸収フィルムを得た。
得られたPMMA近赤外線吸収フィルムの吸収スペクトルを図3に示す。得られたフィルムの最大吸収波長は911nm、化合物No.1−1に換算したモル吸光係数ε=1.6×104で、このフィルムは、近赤外線領域に良好な吸収を示した。
化合物No.1−1を使用しなかった以外は実施例2と同様にして、比較のポリカーボネート近赤外線吸収フィルムを得た。
化合物No.1−1を使用しなかった以外は実施例3と同様にして、比較のPMMA近赤外線吸収フィルムを得た。
実施例2及び3並びに比較例1及び2で得られた近赤外線吸収フィルムのHaze値(透明性)を、JIS K7105に準拠して測定した。測定結果を〔表1〕に示す。
Claims (2)
- 合成樹脂100質量部に対し、下記一般式(1)で表される近赤外線吸収剤0.001〜5質量部を含有する近赤外線吸収性合成樹脂組成物。
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