• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

高いプロトン親和力を持つピリジル系有機顔料の黒色顔料への応用

Research Project

Project/Area Number 16655079
Research Category

Grant-in-Aid for Exploratory Research

Allocation TypeSingle-year Grants
Research Field Functional materials/Devices
Research InstitutionYokohama National University

Principal Investigator

水口 仁  横浜国立大学, 大学院・工学研究院, 教授 (90281005)

Co-Investigator(Kenkyū-buntansha) 千住 孝俊  横浜国立大学, 大学院・工学研究院, 助手 (70322097)
高橋 宏雄  東洋インキエンジニアリング(株)・エンジニアリング部
壹岐 成記  東洋インキエンジニアリング(株), エンジニアリング部, グループリーダー
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2004: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywords有機顔料 / 黒色顔料 / ピロロピロール / 結晶構造 / 電子構造
Research Abstract

初年度の後半で明らかになった事実として、ピリジル系の有機顔料が存在しなくとも、オートクレーブ(圧力反応器)内の反応でペンタンジオールと硝酸のみで黒色顔料が得られることが分かった。これは大変ショックな結果であり、単にペンタンジオールと硝酸をオートクレーブ内で加熱すると、150℃あたりから圧力が1.5MP程度にあがり、この後に黒色固体が生成するものである。しかし、面白いことに開放系では褐色の液状物質しか得られていない。本年度は各種の酸、各種有機溶剤を使って反応の一般化と黒色物生成の反応メカニズムを解明することに専念した。しかし、黒色固体は完全に不溶のためNMRの測定も行えず、質量分析においても試料にイオン衝撃を与えるだけで完全に小さなフラグメントになり、意味ある組成分析は行えなかった。現時点で明らかになっているのはCHNの分析結果と熱分析だけである。このように反応のメカニズムや生成物の詳細は不明であるが、本黒色顔料はあらゆる有機溶剤に不溶で、耐熱性、耐光性に優れていることが明らかになった。そこで、本研究では工学的な点に主眼を移し、電子写真の黒色トナーの帯電補助材として可能性を検討した。電子画像の分野では高解像度の要望が強く、それに応じて可視像化のために使われるトナーは7ミクロン程度の小粒子が要求される。このような小粒子になるとカーボンブラックを主成分とするトナーでは伝導性が高くなり、電子写真で必要な十分な摩擦帯電がえられない。これを補助するのが本黒色顔料である。その結果、他の顔料では得られない際立った帯電補助効果が認められた。これらの、研究成果を踏まえて、製法ならびに応用面についての広範な特許を申請した。また、実装テストとして国内の大手画像メーカー2社にサンプルを提供し、現在のところ良好な結果が得られている。黒色顔料以外の成果として、当初検討したピリジル系の有機顔料は水素ガスセンサー材料として有望であることが分かり、センサー特性ならび構造解析についても広範囲な検討を行った。

Report

(2 results)
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (52 results)

All 2006 2005 2004

All Journal Article (49 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Strikingly different electronic spectra of structurally similar perylene imide compounds2006

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Dyes and Pigments 70

      Pages: 126-135

    • NAID

      120000920854

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Polymorph of N,N'-di-n-butylperylene-3,4:9,10-bis(dicarboximide) and their electronic structure2006

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Dyes and Pigments 70

      Pages: 226-231

    • NAID

      120000920863

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Polymorph of dimethylacetamide-solvated crystals of 2,9-dichlorodithioketoquinacridone and their hydrogen bonding effect2006

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Dyes and Pigments 69

      Pages: 54-61

    • NAID

      120000920860

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 3,6-Di-3-pyridylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione2006

    • Author(s)
      T.Hirota
    • Journal Title

      Acta Cryst. E62

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 3,10-Dichloro-5,12-dihydroquino[2,3- b]acridine-7,14-dione2006

    • Author(s)
      T.Senju
    • Journal Title

      Acta Cryst. E62

    • NAID

      120000922684

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 3,6-Di-4-pyridylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920866

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 3,6-Di-2-pyridylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione2005

    • Author(s)
      T.Imoda
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] tert-Butyl 1,4-dioxo-3,6-diphenyl-1,2,4,5-tetrahydropyrrolo [3,4-c]-pyrrole-2-carboxylate2005

    • Author(s)
      Y.Imura
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Pigent Precursor Based on 1,4-dketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole and its Regeneration into the Pigment2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      J.Imag.Sci.Tech. 49

      Pages: 35-40

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Polymorph of 1,4-diketo-3,6-bis-(4'-dipyridyl) pyrrolo-[3,4-c]pyrrole and their hydrogen bond network : A material for H_2 gas sensor2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Dyes and Pigments 68

      Pages: 47-52

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Hydrogen gas sensor utilizing a high proton affinity of pyrrolopyrrole derivatives2005

    • Author(s)
      H.Takahashi
    • Journal Title

      J.Electrochem.Soc. 152

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Crystal structure of a latent pyrrolopyrrole-pigment and its regeneration process2005

    • Author(s)
      Y.Imura
    • Journal Title

      J.Imag.Sci.Jpn. 44

      Pages: 143-147

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 2,9-Dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dione2005

    • Author(s)
      T.Senju
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Crystal Structure of a quinacridone pigment-precursor and its regeneration process2005

    • Author(s)
      Y.Imura
    • Journal Title

      J.Imag.Sci.Jpn. 44

      Pages: 138-142

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 2,9-Dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dione(red phase)2005

    • Author(s)
      T.Senju
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 2,9-Dichloroquino[2,3-b]acridine-7,14(5H,12H)-dithione dimethylformamide disolvate2005

    • Author(s)
      T.Senju
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] The monoclinic form of 2,9-dihydroquino[2,3-b]acridine-7,14-dithione dimethylacetamide disolvate2005

    • Author(s)
      T.Hoki
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] The triclinic form of 2,9-dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dithione dimethylacetamide disolvate2005

    • Author(s)
      T.Senju
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N,N'-Di-3-pyridylperylene-3,4:9,10-bis(dicarboximide)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920885

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N,N'-Di-2-pyridylperylene-3,4:9,10-bis(dicarboximide)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920861

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N,N'-Di-4-pyridylperylene-3,4:9,10-bis(dicarboximide)2005

    • Author(s)
      K.Hino
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N,N'-Bis[2-(4-pyridyl)ethyl]perylene-3,4:9,10-bis (dicarboximide)phenol disolvate2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920888

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N,N'-Bis[2-(4-pyridyl)ethyl]perylene-3,4:9,10-bis (dicarboximide)m-cresol disolvate2005

    • Author(s)
      K.Hino
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Dibenzimidazo[2,1-a:2',1'-a']anthra[2,1,9-def:6,5,10-d'e'f]diisoquinoline-10,21-dione : trans form (I)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Dibenzimidazo[2,1-a:1',2'-b']anthra[2,1,9-def:6,5,10-d'e'f]diisoquinoline-6,11-dione : cis form (II)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Bis[3,5-di-tert-butyl-2-hydroxybenzoato-κO]-bis(dimethyl sulioxide-κO)zinc(II)2005

    • Author(s)
      T.Makino
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Diacetonitrileheptakis[μ-3,5-bis(1,1-dimethylethyl)-2-hydroxybenzoato-κ^2-O,O']trizinc(II)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] n-Propyl gallate-chloroform (3/0.5)2005

    • Author(s)
      S.Iwata
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] n-Propyl gallate-acetonitrile(2/1)2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920857

    • Related Report
      2005 Annual Research Report
  • [Journal Article] n-Propyl gallate-dichloromethane (3/0.5)2005

    • Author(s)
      A.Hitachi
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] ピロロピロール顔料を用いた高感度水素ガスセンサー - プロトン受容型センサー -2005

    • Author(s)
      高橋宏雄
    • Journal Title

      燃料電池 4

      Pages: 37-40

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 有機顔料を用いたプロトン受容型の水素ガスセンサー2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      JETI 53

      Pages: 1-3

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetra-benzo[b,g,l,q]porphin e toluene trisolvate2005

    • Author(s)
      S.Aramaki
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] (1RS,4SR,8SR,11RS:15SR,18RS,22RS,25SR)-1,4:8,11:15,18:22,25-Tetra ethano-29H,31H-tetrabenzo[b,g,l,q]porphine chloroform disolvate2005

    • Author(s)
      S.Aramaki
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Electronic Structure of Thiazine-Indigo Pigment on the Basis of the Crystal Structure2005

    • Author(s)
      T.Senju
    • Journal Title

      J.Phys.Chem.B 109

      Pages: 7649-7653

    • Related Report
      2005 Annual Research Report
  • [Journal Article] N N'-Bis(4-pyridyl)naphthalene-3,4:7,8-dicarboximide dimethylformamide disolvate2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Acta Cryst. E61

    • NAID

      120000920864

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Diaquabis(3,5-di- tert-butyl-2-hydroxybenzoato-kO^1)zinc(II) dimethylacetamide trisolvate2005

    • Author(s)
      T.Makino
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Triaquabis(3,5-di- tert-butyl-2-hydroxybenzoato- kO^1) zinc(II) dimethylacetamide trisolvate2005

    • Author(s)
      T.Makino
    • Journal Title

      Acta Cryst. E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 潜在顔料 -水素結合系顔料における可溶化技術と顔料再生化プロセス -2005

    • Author(s)
      水口 仁
    • Journal Title

      日本画像学会誌 44

      Pages: 347-355

    • NAID

      130004719700

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Generation of Charge-control Ability of Pararosaniline Due to Protonation and its Protonation Mechanism2005

    • Author(s)
      T.MAKINO
    • Journal Title

      日本画像学会誌 44

      Pages: 342-346

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 物質の色と構造について(I)-電子遷移-2005

    • Author(s)
      水口 仁
    • Journal Title

      日本画像学会誌 44

      Pages: 271-279

    • NAID

      130004483803

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 物質の色と構造について(II) -振動遷移と回転遷移-2005

    • Author(s)
      水口 仁
    • Journal Title

      日本画像学会誌 44

      Pages: 388-395

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 物質の色と構造について(III) -振動電子遷移-2005

    • Author(s)
      水口 仁
    • Journal Title

      日本画像学会誌 44

      Pages: 514-518

    • NAID

      130004719719

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Pigment Precursor Based on 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole and its Regeneration into the Pigment2005

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Journal of Imaging Science and Technology 49

      Pages: 35-40

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Strikingly different electronic spectra of structurally similar perylene imide compounds2005

    • Author(s)
      J.Mizuguchi, K.Hino, K.Tojo
    • Journal Title

      Chemistry of Materials (in press)

    • NAID

      120000920854

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Polymorph of N,N-di-n-butylperylene-3,4:9,10-bis(dicarboximide) and their electronic structure2005

    • Author(s)
      J.Mazuguchi
    • Journal Title

      Dyes and Pigments in press

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Electronic structure of the cis and trans isomers of benzimidazo perylene derivatives and their use as black pigments2005

    • Author(s)
      J.Mizuguchi, N.Shimo
    • Journal Title

      Journal of Imaging Science and Technology in press

    • NAID

      120000922702

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Spectral and crystallographic coincidence in a mixed crystal of two components and a crystal of their hybrid component in pyrrolopyrrole pigmens2004

    • Author(s)
      J.Mizuguchi, H.Shikamori
    • Journal Title

      Journal of Physical Chemistry B 108

      Pages: 2154-2161

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Crystal structure and electronic characterization of trans and cis perinone pigments2004

    • Author(s)
      J.Mizuguchi
    • Journal Title

      Journal of Physical Chemistry B 108

      Pages: 8926-8930

    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] プロトン受容型ガスセンサーの駆動方法、ガス検出方法、及びプロトン受容型ガスセンサー装置2005

    • Inventor(s)
      水口 仁, 高橋宏雄
    • Industrial Property Rights Holder
      国立大学法人横浜国立大学, 東洋インキエンジニアリング(株)
    • Industrial Property Number
      2005-221593
    • Filing Date
      2005-07-29
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] 黒色顔料及びその製造方法2005

    • Inventor(s)
      水口 仁
    • Industrial Property Rights Holder
      国立大学法人横浜国立大学
    • Industrial Property Number
      2005-154403
    • Filing Date
      2005-05-26
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] DP-DDP系黒色顔料及びその製法2004

    • Inventor(s)
      水口 仁
    • Industrial Property Rights Holder
      水口 仁
    • Industrial Property Number
      2004-104560
    • Filing Date
      2004-03-31
    • Related Report
      2004 Annual Research Report

URL: 

Published: 2004-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi