JPWO2012063964A1 - 近赤外線吸収シアニン色素とその用途 - Google Patents
近赤外線吸収シアニン色素とその用途 Download PDFInfo
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- JPWO2012063964A1 JPWO2012063964A1 JP2012542996A JP2012542996A JPWO2012063964A1 JP WO2012063964 A1 JPWO2012063964 A1 JP WO2012063964A1 JP 2012542996 A JP2012542996 A JP 2012542996A JP 2012542996 A JP2012542996 A JP 2012542996A JP WO2012063964 A1 JPWO2012063964 A1 JP WO2012063964A1
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- Prior art keywords
- cyanine dye
- group
- benzo
- general formula
- infrared
- Prior art date
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- GDIYMWAMJKRXRE-UHFFFAOYSA-N (2z)-2-[(2e)-2-[2-chloro-3-[(z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,3,3-trimethylindole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=C1C(Cl)=C(C=CC=2C(C3=CC=CC=C3[N+]=2C)(C)C)CCC1 GDIYMWAMJKRXRE-UHFFFAOYSA-N 0.000 claims abstract description 34
- HFJHUOIVZVHBBM-UHFFFAOYSA-N 1,2-dihydrobenzo[cd]indole Chemical compound C1=CC(CN2)=C3C2=CC=CC3=C1 HFJHUOIVZVHBBM-UHFFFAOYSA-N 0.000 claims abstract description 24
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
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- Materials Engineering (AREA)
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Abstract
Description
反応容器に化学式10で表される化合物10g、化学式11で表される化合物8.37g、及びイソプロピルアルコール50mlを仕込み、室温分散下、無水酢酸5.84ml、トリエチルアミン6.46mlを順次加え、70℃にて加熱攪拌を90分間行なった。反応終了後、水100mlを加え、冷却後、晶析した結晶を濾過し取り出した。得られた粗結晶11.7gとジメチルフォルムアミド110mlとを反応容器に仕込み、70℃にて過熱溶解させた後に、冷却、晶析させ、結晶を濾過し取り出した。取り出した結晶を乾燥させ化学式1で表されるベンゾ[cd]インドリウム系ヘプタメチンシアニン色素5.0gを得た。
本例の化学式1、2、4で表されるシアニン色素について、耐熱性に関する試験を下記のとおり行なった。耐熱性試験は、まず、実施例1記載の化学式1、2、4で表されるシアニン色素を、それぞれ溶剤に溶解した後、ガラス基板上に塗布し製膜した。シアニン色素を製膜した上記3種類のガラス基板について、吸収極大波長(約994nm)におけるシアニン色素の透過率(T0)を測定した後、180℃に熱したホットプレート(商品名『ホットプレート/スターラー PC−320』、コーニング社製造)上にそれぞれのシアニン色素を塗布した上記ガラス基板を150分間放置した。加熱後、直ちに、吸収極大波長における透過率(T)を再度測定し、斯くして得られた透過率T及びT0を下記数1へ代入して色素残存率を求めた。比較例として、従来公知の比較例化合物1乃至3について同様に耐熱試験を行なった。結果を表1に示す。
バインダー樹脂としてポリビニルピロリドン樹脂10g、実施例1で得られた化学式1で表されるベンゾ[cd]インドリウム系ヘプタメチンシアニン色素0.2gをメチルエチルケトン:メチルセルソルブ=4:6混合溶剤90gに溶解し、平均厚さ約5μmのポリエチレンテレフタラート(PET)フィルムにワイヤーバーにて乾燥後の膜厚が約5μmとなるように塗布して、近赤外線吸収剤のフィルム組成物を得た。Nd:YAGレーザー(波長1064nm)のレーザー光をレンズで集光し、上記フィルム組成物の表面でビーム経10μmとなるように配置した。表面に到達するレーザーのパワーを調製し、20μsのパルス幅で単一のパルスを近赤外線フィルム組成物に照射した。照射後、光学顕微鏡で観察したところ、表面に到達するレーザーパワーが50mW時、直径約10μmの貫通溝が確認された。
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